FComEx: Thiamine pyrophosphate (PC000648)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:46 UTC

Update date

2017-01-19 02:36:31 UTC

FoodComEx ID

PC000648

FoodDB Record

FDB022584

Chemical Information

Name

Thiamine pyrophosphate

Description

Thiamine pyrophosphate, also known as thiamin diphosphoric acid or THPP, 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. A 1,3-thiazolium cation that is the conjugate acid of thiamine(1+) diphosphate(1). Thiamine pyrophosphate is a very strong basic compound (based on its pKa). Thiamine pyrophosphate exists in all living species, ranging from bacteria to humans. Within humans, thiamine pyrophosphate participates in a number of enzymatic reactions. In particular, S-(2-methylbutanoyl)-dihydrolipoamide and thiamine pyrophosphate can be biosynthesized from lipoamide and 2-methyl-1-hydroxypropyl-THPP through the action of 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 catalyzed by the enzyme 2-oxoisovalerate dehydrogenase. In humans, thiamine pyrophosphate is involved in the metabolic disorder called the 2-methyl-3-hydroxybutyryl-coa dehydrogenase deficiency pathway.

CAS Number

154-87-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
Thaimine pyroate	HMDB
Thaimine pyrophosphate	hmdb
Thiamin diate	ChEBI
Thiamin diic acid	Generator
thiamin diphosphate	hmdb
Thiamin pyroate	ChEBI
Thiamin pyroic acid	Generator
thiamin pyrophosphate	hmdb
thiamin-PPi	hmdb
Thiamine diate	ChEBI
Thiamine diic acid	Generator
thiamine diphosphate	hmdb
Thiamine pyroate	HMDB
Thiamine pyrophosphate	hmdb
Thiamine pyrophosphic acid	hmdb
thiamine-PPi	hmdb
Thiamine-pyroate	HMDB
thiamine-pyrophosphate	hmdb
ThPP	hmdb
TPP	hmdb

Chemical Formula

C12H19N4O7P2S

IUPAC name

3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium

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

Isomeric SMILES

CC1=C(CCO[P@](O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N

Average Molecular Weight

425.314

Monoisotopic Molecular Weight

425.044967696

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