Showing metabocard for Thiamine pyrophosphate (BMDB0001372)
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| Version | 1.0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Creation Date | 2016-09-30 22:44:54 UTC | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Update Date | 2020-05-21 16:28:44 UTC | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BMDB ID | BMDB0001372 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Secondary Accession Numbers |
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| Metabolite Identification | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Common Name | Thiamine pyrophosphate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | Thiamine pyrophosphate, also known as thiamine pyrophosphate or thiamine pyrophosphate, belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. Thiamine pyrophosphate is possibly soluble (in water) and a very strong basic compound (based on its pKa). Thiamine pyrophosphate exists in all living species, ranging from bacteria to humans. Thiamine pyrophosphate participates in a number of enzymatic reactions, within cattle. In particular, S-(2-Methylbutanoyl)-dihydrolipoamide and thiamine pyrophosphate can be biosynthesized from lipoamide and 2-methyl-1-hydroxypropyl-THPP; which is mediated by the enzymes 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial and 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial. In addition, Ketoleucine and thiamine pyrophosphate can be converted into 3-methyl-1-hydroxybutyl-THPP; which is mediated by the enzyme 2-oxoisovalerate dehydrogenase. In cattle, thiamine pyrophosphate is involved in the metabolic pathway called the valine, leucine, and isoleucine degradation pathway. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Structure | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synonyms |
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| Chemical Formula | C12H19N4O7P2S | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Average Molecular Weight | 425.314 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Monoisotopic Molecular Weight | 425.044967696 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| IUPAC Name | 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Traditional Name | thiamin pyrophosphate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| CAS Registry Number | 154-87-0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| SMILES | CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Identifier | InChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| InChI Key | AYEKOFBPNLCAJY-UHFFFAOYSA-O | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemical Taxonomy | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Description | belongs to the class of organic compounds known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Kingdom | Organic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Super Class | Organoheterocyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Class | Diazines | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Sub Class | Pyrimidines and pyrimidine derivatives | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Direct Parent | Thiamine phosphates | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Alternative Parents | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Substituents |
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| Molecular Framework | Aromatic heteromonocyclic compounds | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Descriptors |
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| Ontology | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Status | Expected but not Quantified | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Origin |
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| Biofunction | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Application | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular locations |
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| Physical Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| State | Solid | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Experimental Properties |
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| Predicted Properties |
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| Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Spectra | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Biological Properties | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Cellular Locations |
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| Biospecimen Locations |
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| Pathways | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Normal Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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| Abnormal Concentrations | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| External Links | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| HMDB ID | HMDB0001372 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| DrugBank ID | DB01987 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Phenol Explorer Compound ID | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| FooDB ID | FDB022584 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KNApSAcK ID | C00019627 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Chemspider ID | 1100 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| KEGG Compound ID | C00068 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BioCyc ID | THIAMINE-PYROPHOSPHATE | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| BiGG ID | 33732 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Wikipedia Link | Thiamine pyrophosphate | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| METLIN ID | 2832 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PubChem Compound | 1132 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| PDB ID | TDP | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| ChEBI ID | 9532 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| References | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Synthesis Reference | Zabrodskaya, S. V.; Oparin, D. A.; Ostrovskii, Yu. M. Selective synthesis of thiamine diphosphate. Zhurnal Obshchei Khimii (1989), 59(1), 226-7. | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| Material Safety Data Sheet (MSDS) | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| General References | Not Available | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Enzymes
- General function:
- Nucleotide transport and metabolism
- Specific function:
- Has nucleotide phosphatase activity towards ATP, GTP, CTP, TTP and UTP. Hydrolyzes nucleoside diphosphates with lower efficiency (By similarity).
- Gene Name:
- NTPCR
- Uniprot ID:
- Q1LZ78
- Molecular weight:
- 20682.0
Reactions
| Thiamine pyrophosphate + Water → Thiamine monophosphate + Hydrogen phosphate | details |
- General function:
- Amino acid transport and metabolism
- Specific function:
- Endoplasmic reticulum 2-OH acyl-CoA lyase involved in the cleavage (C1 removal) reaction in the fatty acid alpha-oxydation in a thiamine pyrophosphate (TPP)-dependent manner. Involved in the phytosphingosine degradation pathway.
- Gene Name:
- ILVBL
- Uniprot ID:
- A6QQT9
- Molecular weight:
- 68110.0
- General function:
- Energy production and conversion
- Specific function:
- Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
- Gene Name:
- TKTL1
- Uniprot ID:
- Q2NL26
- Molecular weight:
- 64966.0
- General function:
- Energy production and conversion
- Specific function:
- Plays an essential role in total transketolase activity and cell proliferation in cancer cells; after transfection with anti-TKTL1 siRNA, total transketolase activity dramatically decreases and proliferation was significantly inhibited in cancer cells. Plays a pivotal role in carcinogenesis (By similarity).
- Gene Name:
- TKTL2
- Uniprot ID:
- Q2NKZ4
- Molecular weight:
- 67501.0
- General function:
- Energy production and conversion
- Specific function:
- Catalyzes the transfer of a two-carbon ketol group from a ketose donor to an aldose acceptor, via a covalent intermediate with the cofactor thiamine pyrophosphate.
- Gene Name:
- TKT
- Uniprot ID:
- Q6B855
- Molecular weight:
- 67906.0
- General function:
- Energy production and conversion
- Specific function:
- The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
- Gene Name:
- BCKDHA
- Uniprot ID:
- P11178
- Molecular weight:
- 51678.0
Reactions
| 3-Methyl-1-hydroxybutyl-ThPP + 2-Methyl-1-hydroxypropyl-ThPP → Thiamine pyrophosphate | details |
| Ketoleucine + Thiamine pyrophosphate → 3-Methyl-1-hydroxybutyl-ThPP + Carbon dioxide | details |
| Alpha-ketoisovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxide | details |
| 3-Methyl-2-oxovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxide | details |
- General function:
- Energy production and conversion
- Specific function:
- The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
- Gene Name:
- BCKDHB
- Uniprot ID:
- P21839
- Molecular weight:
- 42935.0
Reactions
| 3-Methyl-1-hydroxybutyl-ThPP + 2-Methyl-1-hydroxypropyl-ThPP → Thiamine pyrophosphate | details |
| Ketoleucine + Thiamine pyrophosphate → 3-Methyl-1-hydroxybutyl-ThPP + Carbon dioxide | details |
| Alpha-ketoisovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxide | details |
| 3-Methyl-2-oxovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxide | details |
- General function:
- Energy production and conversion
- Specific function:
- 2-oxoglutarate dehydrogenase (E1) component of the 2-oxoglutarate dehydrogenase complex, which mediates the decarboxylation of alpha-ketoglutarate. The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). The 2-oxoglutarate dehydrogenase complex is mainly active in the mitochondrion. A fraction of the 2-oxoglutarate dehydrogenase complex also localizes in the nucleus and is required for lysine succinylation of histones: associates with KAT2A on chromatin and provides succinyl-CoA to histone succinyltransferase KAT2A.
- Gene Name:
- OGDH
- Uniprot ID:
- Q148N0
- Molecular weight:
- 115808.0
- General function:
- Energy production and conversion
- Specific function:
- The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
- Gene Name:
- PDHA1
- Uniprot ID:
- A7MB35
- Molecular weight:
- 43388.0
- General function:
- Coenzyme transport and metabolism
- Specific function:
- Catalyzes the phosphorylation of thiamine to thiamine pyrophosphate. Can also catalyze the phosphorylation of pyrithiamine to pyrithiamine pyrophosphate (By similarity).
- Gene Name:
- TPK1
- Uniprot ID:
- Q5E9T4
- Molecular weight:
- 27028.0
Reactions
| Adenosine triphosphate + Thiamine → Adenosine monophosphate + Thiamine pyrophosphate | details |
| Adenosine triphosphate + Thiamine pyrophosphate → ADP + Thiamin triphosphate | details |
- General function:
- Energy production and conversion
- Specific function:
- The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2), and thereby links the glycolytic pathway to the tricarboxylic cycle.
- Gene Name:
- PDHB
- Uniprot ID:
- P11966
- Molecular weight:
- 39126.0
- General function:
- Involved in binding
- Specific function:
- Mitochondrial transporter mediating uptake of thiamine pyrophosphate (ThPP) into mitochondria.
- Gene Name:
- SLC25A19
- Uniprot ID:
- Q29RM1
- Molecular weight:
- 35112.0
- General function:
- Amino acid transport and metabolism
- Specific function:
- Not Available
- Gene Name:
- HACL1
- Uniprot ID:
- A5PJL6
- Molecular weight:
- 63591.0
- General function:
- Energy production and conversion
- Specific function:
- Not Available
- Gene Name:
- OGDH
- Uniprot ID:
- A8KC82
- Molecular weight:
- 48383.0
- General function:
- Amino acid transport and metabolism
- Specific function:
- Not Available
- Gene Name:
- ILVBL
- Uniprot ID:
- B0JYQ9
- Molecular weight:
- 68223.0