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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:52 UTC
HMDB IDHMDB01512
Secondary Accession NumbersNone
Metabolite Identification
Common NameThiamine triphosphate
DescriptionThiamine triphosphate is the triphosphate ester of thiamine. Thiamine triphosphate (ThTP) was previously considered to be a specific neuroactive form of thiamine. However, it was recently shown that ThTP exists in bacteria, fungi, plants and animals suggesting a much more general cellular role. In particular, it seems to play a role in response to amino acid starvation. In mammals, ThTP is hydrolyzed by a specific thiamine triphosphatase. In Leigh's disease, this compound is present in decreased amounts in the brain due to a metabolic block in its formation.
Structure
Thumb
Synonyms
ValueSource
Thiamin triphosphateChEBI
Thiamine triphosphateChEBI
Thiamin triphosphoric acidGenerator
THTPHMDB
Chemical FormulaC12H20N4O10P3S
Average Molecular Weight505.294
Monoisotopic Molecular Weight505.011298106
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy({[hydroxy(phosphonooxy)phosphoryl]oxy})phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
Traditional Namethiamin triphosphate
CAS Registry Number3475-65-8
SMILES
CC1=C(CCOP(O)(=O)OP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=C(N)N=C(C)N=C1
InChI Identifier
InChI=1S/C12H19N4O10P3S/c1-8-11(30-7-16(8)6-10-5-14-9(2)15-12(10)13)3-4-24-28(20,21)26-29(22,23)25-27(17,18)19/h5,7H,3-4,6H2,1-2H3,(H5-,13,14,15,17,18,19,20,21,22,23)/p+1
InChI KeyInChIKey=IWLROWZYZPNOFC-UHFFFAOYSA-O
Chemical Taxonomy
DescriptionThis compound 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
  • 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
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Thiamine metabolism
ApplicationNot Available
Cellular locations
  • Extracellular
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.37 mg/mLALOGPS
logP-0.49ALOGPS
logP-6.8ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)0.9ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count10ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area215.5 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity106.02 m3·mol-1ChemAxon
Polarizability41.52 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Thiamine MetabolismSMP00076map00730
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 IDFDB022666
KNApSAcK IDNot Available
Chemspider ID496
KEGG Compound IDC03028
BioCyc IDCPD-611
BiGG ID41046
Wikipedia LinkThiamine triphosphate
NuGOwiki LinkHMDB01512
Metagene LinkHMDB01512
METLIN ID3586
PubChem Compound511
PDB IDNot Available
ChEBI ID9534
References
Synthesis ReferenceGrandfils C; Bettendorff L; de Rycker C; Schoffeniels E Synthesis of [gamma-32P]thiamine triphosphate. Analytical biochemistry (1988), 169(2), 274-8.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Kimura M, Itokawa Y: Determination of thiamine and its phosphate esters in human and rat blood by high-performance liquid chromatography with post-column derivatization. J Chromatogr. 1985 Sep 20;332:181-8. [4055941 ]

Enzymes

General function:
Involved in thiamin diphosphokinase activity
Specific function:
Catalyzes the phosphorylation of thiamine to thiamine pyrophosphate. Can also catalyze the phosphorylation of pyrithiamine to pyrithiamine pyrophosphate.
Gene Name:
TPK1
Uniprot ID:
Q9H3S4
Molecular weight:
27265.05
Reactions
Adenosine triphosphate + Thiamine pyrophosphate → ADP + Thiamine triphosphatedetails
General function:
Involved in adenylate cyclase activity
Specific function:
Hydrolase highly specific for thiamine triphosphate (ThTP).
Gene Name:
THTPA
Uniprot ID:
Q9BU02
Molecular weight:
25565.685
Reactions
Thiamine triphosphate + Water → Thiamine pyrophosphate + Phosphoric aciddetails