Showing metabocard for Thiamin triphosphate (BMDB0001512)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:01 UTC
Update Date2020-05-21 16:28:35 UTC
BMDB IDBMDB0001512
Secondary Accession Numbers
  • BMDB01512
Metabolite Identification
Common NameThiamin triphosphate
DescriptionThiamine triphosphate, also known as thiamine triphosphate 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 possibly soluble (in water) and a very strong basic compound (based on its pKa). Thiamine triphosphate exists in all living species, ranging from bacteria to humans. Thiamine triphosphate participates in a number of enzymatic reactions, within cattle. In particular, Thiamine triphosphate can be biosynthesized from thiamine pyrophosphate through its interaction with the enzyme thiamin pyrophosphokinase. In addition, Thiamine triphosphate can be converted into thiamine pyrophosphate through the action of the enzyme thiamine-triphosphatase. In cattle, thiamine triphosphate is involved in the metabolic pathway called the thiamine metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 NumberNot Available
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
StatusExpected but not Quantified
OriginNot Available
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
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-05bb-9674400000-b85f96fa15a79b807f57View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1100090000-be999be10fb2a29960f4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0k9i-3231970000-d7309409890edb94fbbdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052b-9820100000-7518cd452597a739fd3dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0000090000-7ac188b5e05c4f14c656View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-9000120000-50842bfa40a49ea4ede5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9320000000-6249c4331931f95b126cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0300190000-c9dd820f036fb97ca251View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-0588940000-745fc053a6eb56c314d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0910000000-2071dd01d569c75d980fView in MoNA
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001512
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
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 ReferencesNot Available

Enzymes

Enzyme Details
1. Thiamin pyrophosphokinase 1
General function:
Coenzyme transport and metabolism
Specific function:
Catalyzes the phosphorylation of thiamine to thiamine pyrophosphate. Can also catalyze the phosphorylation of pyrithiamine to pyrithiamine pyrophosphate (By similarity).
Gene Name:
TPK1
Uniprot ID:
Q5E9T4
Molecular weight:
27028.0
Reactions
Adenosine triphosphate + Thiamine pyrophosphate → ADP + Thiamin triphosphatedetails
Enzyme Details
2. Thiamine-triphosphatase
General function:
Involved in adenylate cyclase activity
Specific function:
Hydrolase highly specific for thiamine triphosphate (ThTP).
Gene Name:
THTPA
Uniprot ID:
Q8MKF1
Molecular weight:
23983.0
Reactions
Thiamin triphosphate + Water → Thiamine pyrophosphate + Hydrogen phosphatedetails