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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:23:27 UTC
HMDB IDHMDB0001512
Secondary Accession Numbers
  • HMDB01512
Metabolite Identification
Common NameThiamine triphosphate
DescriptionThiamine triphosphate, also known as triphosphate, thiamin or THTP, 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. Thiamine triphosphate is a very strong basic compound (based on its pKa). Thiamine triphosphate exists in all living species, ranging from bacteria to humans. Within humans, thiamine triphosphate participates in a number of enzymatic reactions. In particular, thiamine triphosphate can be biosynthesized from thiamine pyrophosphate; which is catalyzed by the enzyme thiamin pyrophosphokinase. In addition, thiamine triphosphate can be converted into thiamine pyrophosphate; which is catalyzed by the enzyme thiamine-triphosphatase. 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 humans, thiamine triphosphate is involved in the metabolic disorder called the thiamine metabolism pathway. In Leigh's disease, this compound is present in decreased amounts in the brain due to a metabolic block in its formation.
Structure
Data?1582752207
Synonyms
ValueSource
Thiamin triphosphateChEBI
Thiamin triphosphoric acidGenerator
Thiamine triphosphoric acidGenerator
THTPHMDB
Triphosphate, thiaminHMDB
Triphosphate, thiamineHMDB
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 KeyIWLROWZYZPNOFC-UHFFFAOYSA-O
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
  • 4,5-disubstituted 1,3-thiazole
  • Aminopyrimidine
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Imidolactam
  • Azole
  • Thiazole
  • Heteroaromatic compound
  • Azacycle
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count10ChemAxon
Refractivity106.02 m³·mol⁻¹ChemAxon
Polarizability41.52 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bb-9674400000-b85f96fa15a79b807f57Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1100090000-be999be10fb2a29960f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-3231970000-d7309409890edb94fbbdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9820100000-7518cd452597a739fd3dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-7ac188b5e05c4f14c656Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000120000-50842bfa40a49ea4ede5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9320000000-6249c4331931f95b126cSpectrum
Biological Properties
Cellular Locations
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022666
KNApSAcK IDNot Available
Chemspider ID496
KEGG Compound IDC03028
BioCyc IDNot Available
BiGG ID41046
Wikipedia LinkThiamine triphosphate
METLIN ID3586
PubChem Compound511
PDB IDNot Available
ChEBI ID9534
Food Biomarker OntologyNot Available
VMH IDTHMTP
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. [PubMed: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 + Phosphatedetails