Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000462
Identification
Name: Thiamine monophosphate
Description:Thiamine dihydrogen phosphate ester. The monophosphate ester of thiamine. Synonyms: monophosphothiamine; vitamin B1 monophosphate. -- Pubchem
Structure
Thumb
Synonyms:
  • Aneurin-monophosphorsaeureester
  • Aneurine monophosphate
  • Aneurine monophosphoric acid
  • Monofosfotiamina
  • Monophosphoric ester of thiamine
  • Monophosphothiamine
  • Monophosphothiaminum
  • Phosphothiaminum
  • Thiamin dihydrogenphosphate
  • Thiamin dihydrogenphosphoric acid
  • Thiamin monophosphate
  • Thiamin monophosphoric acid
  • Thiamin phosphate
  • Thiamin phosphoric acid
  • Thiamin-P
  • Thiamine monophosphate
  • Thiamine monophosphate dihydrate
  • Thiamine monophosphoric acid
  • Thiamine monophosphoric acid dihydric acid
  • Thiamine phosphate
  • Thiamine phosphoric acid
  • Thiamine-phosphate
  • Thiamine-phosphoric acid
  • Thiamine-Pi
  • ThiamineP
  • ThP
  • Tiamina monofosfato
  • TMP
Chemical Formula: C12H17N4O4PS
Average Molecular Weight: 344.327
Monoisotopic Molecular Weight: 344.070812254
InChI Key: HZSAJDVWZRBGIF-UHFFFAOYSA-N
InChI:InChI=1S/C12H17N4O4PS/c1-8-11(3-4-20-21(17,18)19)22-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H3-,13,14,15,17,18,19)
CAS number: 495-23-8
IUPAC Name:3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-5-[2-(phosphonooxy)ethyl]-1,3-thiazol-3-ium
Traditional IUPAC Name: thiamin monophosphate
SMILES:CC1=C(CCO[P@](O)([O-])=O)SC=[N+]1CC1=CN=C(C)N=C1N
Chemical Taxonomy
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.
Kingdom Organic compounds
Super ClassOrganoheterocyclic compounds
Class Diazines
Sub ClassPyrimidines and pyrimidine derivatives
Direct Parent Thiamine phosphates
Alternative Parents
Substituents
  • Thiamine-phosphate
  • Monoalkyl phosphate
  • Aminopyrimidine
  • 4,5-disubstituted 1,3-thiazole
  • Imidolactam
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Hydropyrimidine
  • Heteroaromatic compound
  • Thiazole
  • Azole
  • Azacycle
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.0456 mg/mLALOGPS
logP-1.6ALOGPS
logP-5.7ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)1.66ChemAxon
pKa (Strongest Basic)5.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area122.44 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.27 m3·mol-1ChemAxon
Polarizability32.87 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0109000000-eaecb343c9ff0c6f060fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-9148000000-58b0f8616c541d910c2aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-3900000000-cbb443e2c206edc550d7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-4109000000-1d9d048d26c541eac8d6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002b-9001000000-3b5f50e234444b8876e6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-8a23656944b47d54a23aView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
Synthesis Reference: Leder, Irwin G. Enzymic synthesis of thiamine monophosphate. Journal of Biological Chemistry (1961), 236 3066-71.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID9533
HMDB IDHMDB02666
Pubchem Compound ID1131
Kegg IDC01081
ChemSpider ID2627905
WikipediaThiamine monophosphate
BioCyc IDTHIAMINE-P
EcoCyc IDTHIAMINE-P
Ligand ExpoTPS