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Record Information
Version5.0
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 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 exists in all living species, ranging from bacteria to plants to humans. In humans, thiamine triphosphate is involved in the metabolic disorder called the thiamine metabolism pathway. Thiamine triphosphate has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make thiamine triphosphate a potential biomarker for the consumption of these foods. Thiamine triphosphate is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Thiamine triphosphate.
Structure
Data?1582752207
Synonyms
ValueSource
3-[(4-Amino-2-methyl-5-pyrimidinyl)methyl]-4-methyl-5-(4,6,8,8-trihydroxy-4,6,8-trioxido-3,5,7-trioxa-4,6,8-triphosphaoct-1-yl)-thiazoliumChEBI
3-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-5-{2-[(hydroxy{[hydroxy(phosphonooxy)phosphoryl]oxy}phosphoryl)oxy]ethyl}-4-methyl-1,3-thiazol-3-iumChEBI
Thiamin triphosphateChEBI
Thiamine triphosphoric acid esterChEBI
THTPChEBI
TTPChEBI
Thiamin triphosphoric acidGenerator
Thiamine triphosphate esterGenerator
Thiamine triphosphoric acidGenerator
Triphosphate, thiaminMeSH, HMDB
Triphosphate, thiamineMeSH, HMDB
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 Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular 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
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available209.56131661259
DarkChem[M-H]-PredictedNot Available199.67231661259
AllCCS[M+H]+PredictedNot Available201.67232859911
AllCCS[M-H]-PredictedNot Available193.6732859911

Retention Indices

Underivatized

Not Available

Derivatized

Not Available
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bb-9674400000-b85f96fa15a79b807f572017-09-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1100090000-be999be10fb2a29960f42016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-3231970000-d7309409890edb94fbbd2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9820100000-7518cd452597a739fd3d2016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-7ac188b5e05c4f14c6562016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000120000-50842bfa40a49ea4ede52016-09-12View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9320000000-6249c4331931f95b126c2016-09-12View Spectrum
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
MarkerDB IDNot Available
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