CID 1132
PubChem CID: 1132
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| Compound Synonyms | thiamine diphosphate, 136-08-3, ThPP, thiamin diphosphate, thiamin pyrophosphate, ThDP, CHEBI:9532, thiamine-pyrophosphate, Cocarboxylase [INN], 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate, thiamine(1+) diphosphate, thiamine-PPi, thiamin-PPi, Pyrophosphoric ester of thiamine, COCARBOXYLASE [MART.], COCARBOXYLASE [WHO-DD], DTXSID2048404, 3-((4-Amino-2-methylpyrimidin-5-yl)methyl)-5-(2-((hydroxy(phosphonooxy)phosphoryl)oxy)ethyl)-4-methylthiazol-3-ium, 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-[4,6,6-trihydroxy-4,6-dioxo-3,5-dioxa-4,6-diph, NCGC00160617-01, Q57971654Y, 1ols, 1olu, 1olx, Thaimine pyrophosphate, 1v1m, starbld0000845, 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(diphosphooxy)ethyl]-4-methyl-1,3-thiazol-3-ium, THIAZOLIUM, 3-((4-AMINO-2-METHYL-5-PYRIMIDINYL)METHYL)-4-METHYL-5-(4,6,6-TRIHYDROXY-4,6-DIOXIDO-3,5-DIOXA-4,6-DIPHOSPHAHEX-1-YL)-, Thiazolium, 3-((4-amino-2-methyl-5-pyrimidinyl)methyl)-4-methyl-5-(4,6,6-trihydroxy-4,6-dioxido-3,5-dioxa-4,6-diphosphahex-1-yl)-, inner salt, SCHEMBL80028, CHEMBL1236376, BDBM92962, 1v11, 1v16, AYEKOFBPNLCAJY-UHFFFAOYSA-O, AKOS015961391, NCGC00160617-02, NCGC00160617-03, AC-13726, NS00070401, C00068, Q415003, BRD-A09994331-003-02-4, 3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[(S)-hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium |
|---|---|
| Topological Polar Surface Area | 197.0 |
| Hydrogen Bond Donor Count | 4.0 |
| Heavy Atom Count | 26.0 |
| Pathway Kegg Map Id | map00730, map00280 |
| Description | Thiamine pyrophosphate is the active form of thiamine, and it serves as a cofactor for several enzymes involved primarily in carbohydrate catabolism. The enzymes are important in the biosynthesis of a number of cell constituents, including neurotransmitters, and for the production of reducing equivalents used in oxidant stress defenses and in biosyntheses and for synthesis of pentoses used as nucleic acid precursors. The chemical structure of TPP is that of an aromatic methylaminopyrimidine ring, linked via a methylene bridge to a methylthiazolium ring with a pyrophosphate group attached to a hydroxyethyl side chain. In non-enzymatic model studies it has been demonstrated that the thiazolium ring can catalyse reactions which are similar to those of TPP-dependent enzymes but several orders of magnitude slower. Using infrared and NMR spectrophotometry it has been shown that the dissociation of the proton from C2 of the thiazolium ring is necessary for catalysis, the abstraction of the proton leads to the formation of a carbanion (ylid) with the potential for a nucleophilic attack on the carbonyl group of the substrate. In all TPP-dependent enzymes the abstraction of the proton from the C2 atom is the first step in catalysis, which is followed by a nucleophilic attack of this carbanion on the substrate. Subsequent cleavage of a C-C bond releases the first product with formation of a second carbanion (2-greek small letter alpha-carbanion or enamine). The formation of this 2-greek small letter alpha-carbanion is the second feature of TPP catalysis common to all TPP-dependent enzymes. Depending on the enzyme and the substrate(s), the reaction intermediates and products differ. Methyl-branched fatty acids, as phytanic acid, undergo peroxisomal beta-oxidation in which they are shortened by 1 carbon atom. This process includes four steps: activation, 2-hydroxylation, thiamine pyrophosphate dependent cleavage and aldehyde dehydrogenation. In the third step, 2-hydroxy-3-methylacyl-CoA is cleaved in the peroxisomal matrix by 2-hydroxyphytanoyl-CoA lyase (2-HPCL), which uses thiamine pyrophosphate (TPP) as cofactor. The thiamine pyrophosphate dependence of the third step is unique in peroxisomal mammalian enzymology. Human pathology due to a deficient alpha-oxidation is mostly linked to mutations in the gene coding for the second enzyme of the sequence, phytanoyl-CoA hydroxylase (EC 1.14.11.18). (PMID: 12694175, 11899071, 9924800) [HMDB] |
| Isotope Atom Count | 0.0 |
| Molecular Complexity | 568.0 |
| Database Name | cmaup_ingredients;fooddb_chem_all;hmdb_chem_all;pubchem |
| Defined Atom Stereocenter Count | 0.0 |
| Enzyme Uniprot Id | P11177, P08559, P29803, P21953, Q02218, Q9H3S4, Q9BU02, Q96HY7, Q9ULD0, Q9BSD7 |
| Uniprot Id | P11177, P08559, P29803, P21953, P12694, Q02218, Q9H3S4, P51854, P29401, O75356, Q9BU02, Q9H0I9, A1L0T0, Q9UJ83, Q96HY7, Q9ULD0, Q9BSD7 |
| Iupac Name | 2-[3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl]ethyl phosphono hydrogen phosphate |
| Prediction Hob | 0.0 |
| Class | Diazines |
| Target Id | NPT483 |
| Xlogp | -1.2 |
| Superclass | Organoheterocyclic compounds |
| Subclass | Pyrimidines and pyrimidine derivatives |
| Molecular Formula | C12H19N4O7P2S+ |
| Prediction Swissadme | 0.0 |
| Inchi Key | AYEKOFBPNLCAJY-UHFFFAOYSA-O |
| Fcsp3 | 0.4166666666666667 |
| Logs | -1.3 |
| Rotatable Bond Count | 8.0 |
| State | Solid |
| Logd | -0.718 |
| Synonyms | Thaimine pyroate, Thaimine pyrophosphate, Thiamin diate, Thiamin diic acid, thiamin diphosphate, Thiamin pyroate, Thiamin pyroic acid, thiamin pyrophosphate, thiamin-PPi, Thiamine diate, Thiamine diic acid, thiamine diphosphate, Thiamine pyroate, Thiamine pyrophosphate, Thiamine pyrophosphic acid, thiamine-PPi, Thiamine-pyroate, thiamine-pyrophosphate, ThPP, TPP, Thiamin diphosphate, Thiamin pyrophosphate, Thiamine diphosphate, THPP, Thiamin diphosphoric acid, Thiamin pyrophosphoric acid, Thiamine diphosphoric acid, Thiamine pyrophosphoric acid, Thiamin-ppi, Thiamine-ppi, Thiamine-pyrophosphate, Cocarboxylase, Berolase, Pyrophosphate, thiamine |
| Substituent Name | Thiamine-phosphate, Organic pyrophosphate, Monoalkyl phosphate, Aminopyrimidine, 4,5-disubstituted 1,3-thiazole, Imidolactam, Alkyl phosphate, Primary aromatic amine, Phosphoric acid ester, Organic phosphoric acid derivative, Organic phosphate, Heteroaromatic compound, Thiazole, Azole, Azacycle, Hydrocarbon derivative, Primary amine, Organooxygen compound, Organonitrogen compound, Amine, Organic cation, Aromatic heteromonocyclic compound |
| Compound Name | CID 1132 |
| Kingdom | Organic compounds |
| Prediction Hob Swissadme | 0.0 |
| Exact Mass | 425.045 |
| Formal Charge | 1.0 |
| Monoisotopic Mass | 425.045 |
| Hydrogen Bond Acceptor Count | 11.0 |
| Molecular Weight | 425.32 |
| Covalent Unit Count | 1.0 |
| Total Atom Stereocenter Count | 0.0 |
| Total Bond Stereocenter Count | 0.0 |
| Molecular Framework | Aromatic heteromonocyclic compounds |
| Esol | -2.2494609230769234 |
| Inchi | 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 |
| Smiles | CC1=C(SC=[N+]1CC2=CN=C(N=C2N)C)CCOP(=O)(O)OP(=O)(O)O |
| Nring | 2.0 |
| Defined Bond Stereocenter Count | 0.0 |
| Taxonomy Direct Parent | Thiamine phosphates |
- 1. Outgoing r'ship
FOUND_INto/from Arabidopsis Thaliana (Plant) Rel Props:Source_db:cmaup_ingredients