Record Information
Version3.6
Creation Date2006-08-13 07:01:57 UTC
Update Date2013-02-09 00:12:49 UTC
HMDB IDHMDB03904
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-(a-Hydroxyethyl)thiamine diphosphate
Description2-Hydroxyethyl-ThPP is involved in Glycolysis, Gluconeogenesis, Alanine and aspartate matabolism, Valine, Leucine and isoleucine biosynthesis, Pyruvate metabolism, and Butanoate metabolism [Kegg: c05125].
Structure
Thumb
Synonyms
  1. 2-(alpha-Hydroxyethyl)thiamine diphosphate
  2. 2-Hydroxyethyl-ThPP
  3. 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-2-(1-hydroxyethyl)-4-methyl-5-(4,6,6-trihydroxy-3,5-dioxa-4,6-diphosphahex-1-yl)- P,P'-dioxide
  4. 3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-2-(1-hydroxyethyl)-5-(2-hydroxyethyl)-4-methyl- 5-(trihydrogen pyrophosphate) (8CI)
  5. Thiazolium
Chemical FormulaC14H23N4O8P2S
Average Molecular Weight469.367
Monoisotopic Molecular Weight469.071182446
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-2-(1-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium
Traditional IUPAC Name2-Hydroxyethyl-ThPP
CAS Registry Number10055-47-7
SMILES
CC(O)C1=[N+](CC2=CN=C(C)N=C2N)C(C)=C(CCOP(O)(=O)OP(O)(O)=O)S1
InChI Identifier
InChI=1S/C14H22N4O8P2S/c1-8-12(4-5-25-28(23,24)26-27(20,21)22)29-14(9(2)19)18(8)7-11-6-16-10(3)17-13(11)15/h6,9,19H,4-5,7H2,1-3H3,(H4-,15,16,17,20,21,22,23,24)/p+1
InChI KeyRRUVJGASJONMDY-UHFFFAOYSA-O
Chemical Taxonomy
KingdomOrganic Compounds
Super ClassAromatic Heteropolycyclic Compounds
ClassThiamines
Sub ClassThiamine Phosphates
Other Descriptors
  • 1,3-thiazolium cation(ChEBI)
  • Thiamines
  • thiamine phosphate(ChEBI)
Substituents
  • Aminopyrimidine
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Phosphoric Acid Ester
  • Pyrimidine
  • Secondary Alcohol
  • Thiazole
Direct ParentThiamine Phosphates
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.401Not Available
Predicted Properties
PropertyValueSource
water solubility0.09 g/LALOGPS
logP-0.67ALOGPS
logP-6.9ChemAxon
logS-3.8ALOGPS
pKa (strongest acidic)1.78ChemAxon
pKa (strongest basic)5.53ChemAxon
physiological charge-1ChemAxon
hydrogen acceptor count9ChemAxon
hydrogen donor count5ChemAxon
polar surface area189.2ChemAxon
rotatable bond count9ChemAxon
refractivity116.58ChemAxon
polarizability42.31ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Pyruvate MetabolismSMP00060map00620
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB023246
KNApSAcK IDNot Available
Chemspider ID389468
KEGG Compound IDC05125
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB03904
Metagene LinkHMDB03904
METLIN IDNot Available
PubChem Compound440568
PDB IDNot Available
ChEBI ID978
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Gene Name:
PDHB
Uniprot ID:
P11177
Reactions
Pyruvic acid + Thiamine pyrophosphate unknown 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxidedetails
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine unknown [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphatedetails
Gene Name:
PDHA1
Uniprot ID:
P08559
Reactions
Pyruvic acid + Thiamine pyrophosphate unknown 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxidedetails
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine unknown [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphatedetails
Gene Name:
PDHA2
Uniprot ID:
P29803
Reactions
Pyruvic acid + Thiamine pyrophosphate unknown 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxidedetails
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine unknown [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphatedetails
Gene Name:
ILVBL
Uniprot ID:
A1L0T0