Human Metabolome Database Version 3.5

Showing metabocard for 2-(a-Hydroxyethyl)thiamine diphosphate (HMDB03904)

Record Information
Version 3.5
Creation Date 2006-08-13 01:01:57 -0600
Update Date 2013-02-08 17:12:49 -0700
HMDB ID HMDB03904
Secondary Accession Numbers None
Metabolite Identification
Common Name 2-(a-Hydroxyethyl)thiamine diphosphate
Description 2-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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C14H23N4O8P2S
Average Molecular Weight 469.367
Monoisotopic Molecular Weight 469.071182446
IUPAC Name 3-[(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 Name 2-Hydroxyethyl-ThPP
CAS Registry Number 10055-47-7
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 Key RRUVJGASJONMDY-UHFFFAOYSA-O
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Thiamines
Sub Class Thiamine 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 Parent Thiamine Phosphates
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations Not Available
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP 0.401 Not Available
Predicted Properties
Property Value Source
Water Solubility 0.09 g/L ALOGPS
LogP -0.67 ALOGPS
LogP -6.9 ChemAxon
LogS -3.75 ALOGPS
pKa (strongest acidic) 1.78 ChemAxon
pKa (strongest basic) 5.53 ChemAxon
Hydrogen Acceptor Count 9 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 189.2 A2 ChemAxon
Rotatable Bond Count 9 ChemAxon
Refractivity 116.58 ChemAxon
Polarizability 42.31 ChemAxon
Formal Charge 1 ChemAxon
Physiological Charge -1 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations Not Available
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Pyruvate Metabolism SMP00060 map00620 Link_out
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB023246
KNApSAcK ID Not Available
Chemspider ID 389468 Link_out
KEGG Compound ID C05125 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB03904 Link_out
Metagene Link HMDB03904 Link_out
METLIN ID Not Available
PubChem Compound 440568 Link_out
PDB ID Not Available
ChEBI ID 978 Link_out
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available

Enzymes
Name: Pyruvate dehydrogenase E1 component subunit beta, mitochondrial
Reactions:
Pyruvic acid + Thiamine pyrophosphate unknown 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxide details
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine unknown [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphate details
Gene Name: PDHB
Uniprot ID: P11177 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyruvate dehydrogenase E1 component subunit alpha, somatic form, mitochondrial
Reactions:
Pyruvic acid + Thiamine pyrophosphate unknown 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxide details
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine unknown [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphate details
Gene Name: PDHA1
Uniprot ID: P08559 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Pyruvate dehydrogenase E1 component subunit alpha, testis-specific form, mitochondrial
Reactions:
Pyruvic acid + Thiamine pyrophosphate unknown 2-(a-Hydroxyethyl)thiamine diphosphate + Carbon dioxide details
2-(a-Hydroxyethyl)thiamine diphosphate + Enzyme N6-(lipoyl)lysine unknown [Dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + Thiamine pyrophosphate details
Gene Name: PDHA2
Uniprot ID: P29803 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: 2-oxoglutarate dehydrogenase, mitochondrial
Reactions: Not Available
Gene Name: OGDH
Uniprot ID: Q02218 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Acetolactate synthase-like protein
Reactions: Not Available
Gene Name: ILVBL
Uniprot ID: A1L0T0 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA