Thiamine triphosphate (CHEM035251)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 05:36:28 UTC
Update Date2016-11-09 01:21:16 UTC
Accession NumberCHEM035251
Identification
Common NameThiamine triphosphate
ClassSmall Molecule
DescriptionA thiamine phosphate that is thiamine(1+) in which the hydroxy group is replaced by a triphosphate group. It is found in low amounts in most vertebrate tissues and can phosphorylate certain proteins.
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical 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 Mass505.294 g/mol
Monoisotopic Mass505.011 g/mol
CAS Registry Number3475-65-8
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
SMILESCC1=C(CCOP(O)(=O)OP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=C(N)N=C(C)N=C1
InChI IdentifierInChI=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
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot 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
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0300190000-c9dd820f036fb97ca251Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-0588940000-745fc053a6eb56c314d7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0910000000-2071dd01d569c75d980fSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0001512
FooDB IDFDB022666
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG ID41046
BioCyc IDNot Available
METLIN ID3586
PDB IDNot Available
Wikipedia LinkThiamine triphosphate
Chemspider ID496
ChEBI ID9534
PubChem Compound ID511
Kegg Compound IDC03028
YMDB IDYMDB00775
ECMDB IDM2MDB005722
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12379473
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=12943234
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1294713
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=1297771
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=14769791
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=1506715
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=18215312
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=19490098
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=19906644
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23323214
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=24590690
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=26221030
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=29223015
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=3010036
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=3039089
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=31941143
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=32885135
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=6329572
19.
20. Grandfils C; Bettendorff L; de Rycker C; Schoffeniels E Synthesis of [gamma-32P]thiamine triphosphate. Analytical biochemistry (1988), 169(2), 274-8.
21. 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.