<?xml version="1.0" encoding="UTF-8"?>
<metabolite>
  <version>1.0</version>
  <creation_date>2016-09-30 22:29:08 UTC</creation_date>
  <update_date>2020-04-22 15:03:06 UTC</update_date>
  <accession>BMDB0000352</accession>
  <secondary_accessions>
    <accession>BMDB00352</accession>
  </secondary_accessions>
  <name>16a-Hydroxydehydroisoandrosterone</name>
  <description/>
  <synonyms>
    <synonym>16alpha-Hydroxydehydroisoandrosterone</synonym>
    <synonym>3beta,16alpha-Dihydroxy-androst-5-en-17-one</synonym>
    <synonym>5-Androstene-3beta,16alpha-diol-17-one</synonym>
    <synonym>16Α-hydroxydehydroisoandrosterone</synonym>
    <synonym>3b,16a-Dihydroxy-androst-5-en-17-one</synonym>
    <synonym>3Β,16α-dihydroxy-androst-5-en-17-one</synonym>
    <synonym>5-Androstene-3b,16a-diol-17-one</synonym>
    <synonym>5-Androstene-3β,16α-diol-17-one</synonym>
    <synonym>16 alpha-Hydroxy-dehydroepiandrosterone</synonym>
    <synonym>16-Hydroxydehydroandrosterone</synonym>
    <synonym>16-Hydroxydehydroepiandrosterone</synonym>
    <synonym>16a-Hydroxy-dhea</synonym>
    <synonym>16a-Hydroxydehydroandrosterone</synonym>
    <synonym>16a-Hydroxydehydroepiandrosterone</synonym>
    <synonym>3b,16a-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>Androst-5-ene-3b-16a-diol-17-one</synonym>
    <synonym>16alpha-Hydroxy-dehydroepiandrosterone</synonym>
    <synonym>3beta,16alpha-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>16 alpha-Hydroxydehydroisoandrosterone</synonym>
    <synonym>3,16-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>3 beta,16 beta-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>16 beta-Hydroxydehydroepiandrosterone</synonym>
    <synonym>3 beta,16 alpha-Dihydroxyandrost-5-en-17-one</synonym>
    <synonym>16-Hydroxydehydroepiandrosterone, (16beta)-isomer</synonym>
    <synonym>16-Hydroxydehydroepiandrosterone, (3alpha,16alpha)-isomer</synonym>
    <synonym>16Α-hydroxydehydroepiandrosterone</synonym>
    <synonym>16a-Hydroxydehydroisoandrosterone</synonym>
  </synonyms>
  <chemical_formula>C19H28O3</chemical_formula>
  <average_molecular_weight>304.4238</average_molecular_weight>
  <monisotopic_moleculate_weight>304.203844762</monisotopic_moleculate_weight>
  <iupac_name>(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one</iupac_name>
  <traditional_iupac>16a-Hydroxy-DHEA</traditional_iupac>
  <cas_registry_number>1232-73-1</cas_registry_number>
  <smiles>[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</smiles>
  <inchi>InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1</inchi>
  <inchikey>QQIVKFZWLZJXJT-DNKQKWOHSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.</description>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Steroids and steroid derivatives</class>
    <sub_class>Androstane steroids</sub_class>
    <direct_parent>Androgens and derivatives</direct_parent>
    <alternative_parents>
      <alternative_parent>16-alpha-hydroxysteroids</alternative_parent>
      <alternative_parent>17-oxosteroids</alternative_parent>
      <alternative_parent>3-beta-hydroxy delta-5-steroids</alternative_parent>
      <alternative_parent>3-beta-hydroxysteroids</alternative_parent>
      <alternative_parent>Cyclic alcohols and derivatives</alternative_parent>
      <alternative_parent>Delta-5-steroids</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Ketones</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Secondary alcohols</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>16-alpha-hydroxysteroid</substituent>
      <substituent>16-hydroxysteroid</substituent>
      <substituent>17-oxosteroid</substituent>
      <substituent>3-beta-hydroxy-delta-5-steroid</substituent>
      <substituent>3-beta-hydroxysteroid</substituent>
      <substituent>3-hydroxy-delta-5-steroid</substituent>
      <substituent>3-hydroxysteroid</substituent>
      <substituent>Alcohol</substituent>
      <substituent>Aliphatic homopolycyclic compound</substituent>
      <substituent>Androgen-skeleton</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Cyclic alcohol</substituent>
      <substituent>Delta-5-steroid</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Hydroxysteroid</substituent>
      <substituent>Ketone</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Oxosteroid</substituent>
      <substituent>Secondary alcohol</substituent>
    </substituents>
    <molecular_framework>Aliphatic homopolycyclic compounds</molecular_framework>
    <external_descriptors>
      <external_descriptor>16alpha-hydroxy steroid</external_descriptor>
      <external_descriptor>17-oxo steroid</external_descriptor>
      <external_descriptor>3beta-hydroxy steroid</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>C19 steroids (androgens) and derivatives</external_descriptor>
      <external_descriptor>androstanoid</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <experimental_properties>
    <state>Solid</state>
  </experimental_properties>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>2.42</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-3.41</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logp</kind>
      <value>2.49</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_acidic</kind>
      <value>13.38</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>pka_strongest_basic</kind>
      <value>-1.4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>iupac</kind>
      <value>(1S,2R,5S,10R,11S,13R,15S)-5,13-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-14-one</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>average_mass</kind>
      <value>304.4238</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mono_mass</kind>
      <value>304.203844762</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>smiles</kind>
      <value>[H][C@@]12C[C@@H](O)C(=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC=C2C[C@@H](O)CC[C@]12C</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formula</kind>
      <value>C19H28O3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchi</kind>
      <value>InChI=1S/C19H28O3/c1-18-7-5-12(20)9-11(18)3-4-13-14(18)6-8-19(2)15(13)10-16(21)17(19)22/h3,12-16,20-21H,4-10H2,1-2H3/t12-,13+,14-,15-,16+,18-,19-/m0/s1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>inchikey</kind>
      <value>QQIVKFZWLZJXJT-DNKQKWOHSA-N</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polar_surface_area</kind>
      <value>57.53</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>refractivity</kind>
      <value>86.15</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>polarizability</kind>
      <value>34.85</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rotatable_bond_count</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>acceptor_count</kind>
      <value>3</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>donor_count</kind>
      <value>2</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>physiological_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>formal_charge</kind>
      <value>0</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>number_of_rings</kind>
      <value>4</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>bioavailability</kind>
      <value>1</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>rule_of_five</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>ghose_filter</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>veber_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
    <property>
      <kind>mddr_like_rule</kind>
      <value>Yes</value>
      <source>ChemAxon</source>
    </property>
  </predicted_properties>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94671</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94672</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>94673</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158742</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158743</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>158744</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2308065</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2308066</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2308067</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2653703</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2653704</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2653705</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>23410</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>37456</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>137138</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>144872</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059299</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059301</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059303</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059305</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059307</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059308</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059311</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059313</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059315</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059317</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>1059319</spectrum_id>
    </spectrum>
  </spectra>
  <normal_concentrations>
  </normal_concentrations>
  <foodb_id>FDB021975</foodb_id>
  <chemspider_id>92168</chemspider_id>
  <chebi_id>27771</chebi_id>
  <pubchem_compound_id>102030</pubchem_compound_id>
  <kegg_id>C05139</kegg_id>
  <drugbank_id/>
  <phenol_explorer_compound_id/>
  <knapsack_id/>
  <bigg_id/>
  <wikipedia_id/>
  <metlin_id>5341</metlin_id>
  <meta_cyc_id/>
  <pdbe_id/>
  <synthesis_reference>Siiter, Pentti K.; MacDonald, Paul C.  Placental estrogen biosynthesis during human pregnancy.    Journal of Clinical Endocrinology and Metabolism  (1966),  26(7),  751-61.</synthesis_reference>
  <general_references>
  </general_references>
  <protein_associations>
  </protein_associations>
</metabolite>
