Record Information
Version1.0
Creation date2015-10-09 22:31:46 UTC
Update date2017-01-19 02:36:31 UTC
FoodComEx IDPC000648
FoodDB RecordFDB022584
Chemical Information
NameThiamine pyrophosphate
DescriptionThiamine 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 Number154-87-0
Structure
Thumb
Synonyms
SynonymSource
Thaimine pyroateHMDB
Thaimine pyrophosphatehmdb
Thiamin diateChEBI
Thiamin diic acidGenerator
thiamin diphosphatehmdb
Thiamin pyroateChEBI
Thiamin pyroic acidGenerator
thiamin pyrophosphatehmdb
thiamin-PPihmdb
Thiamine diateChEBI
Thiamine diic acidGenerator
thiamine diphosphatehmdb
Thiamine pyroateHMDB
Thiamine pyrophosphatehmdb
Thiamine pyrophosphic acidhmdb
thiamine-PPihmdb
Thiamine-pyroateHMDB
thiamine-pyrophosphatehmdb
ThPPhmdb
TPPhmdb
Chemical FormulaNot Available
IUPAC nameNot Available
InChI IdentifierInChI=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 KeyAYEKOFBPNLCAJY-UHFFFAOYSA-O
Isomeric SMILESCC1=C(CCO[P@](O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N
Average Molecular Weight425.314
Monoisotopic Molecular Weight425.044967696
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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct ParentThiamine phosphates
Alternative Parents
Substituents
  • Thiamine-phosphate
  • Organic pyrophosphate
  • 4,5-disubstituted 1,3-thiazole
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Imidolactam
  • Thiazole
  • Azole
  • Heteroaromatic compound
  • Azacycle
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
PropertyValueReference
Experimental logPNot Available
Experimental Water SolubilityNot Available
Melting PointNot Available
Foods of Origin
FoodContent Range AverageReference
FoodReference
Production Data
Production Methodcommercial
Production Method ReferenceNot Available
Production Method Reference FileNot Available
Quantity AvailableProduction upon request, up to 100 mg
Delivery TimeNot Available
Storage Formsolid
Storage Conditions-80°C
StabilityNot Available
PurityNot Available
Spectra
Spectral Data Upon RequestNot Available
Provider Information
Contact NameContact InstitutionContact Email
Rosa Vazquez Fresnovazquezf@ualberta.ca
Commercial Vendors
AKSci M204
Cayman Chemical 20254
Glentham GV8106
MetaSci HMDB0001372
Sigma-Aldrich HMDB0001372
Toronto Research Chemicals T344070