thiamin phosphate (PAMDB110813)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB110813
Identification
Name: thiamin phosphate
Description:Thiamine monophosphate is a thiamine derivative. It is a monophosphate ester of thiamine. Thiamine monophosphate (ThMP) is one of the five known natural thiamine phosphate derivatives. Thiamine (vitamin B1) is the transport form of the vitamin, while the phosphorylated derivatives are the active forms. There is no known physiological role of thiamine monophosphate.
Structure
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🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • TMP
  • thiamin monophosphate
  • thiamine-phosphate
  • thiamin-P
  • thiamine-Pi
  • ThP
  • thiamine monophosphate
Chemical Formula: C12H16N4O4PS
Average Molecular Weight: 343.32
Monoisotopic Molecular Weight: 345.078637287
InChI Key: HZSAJDVWZRBGIF-UHFFFAOYSA-M
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)/p-1
CAS number: 495-23-8
IUPAC Name:2-{3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-4-methyl-1,3-thiazol-3-ium-5-yl}ethyl phosphate
Traditional IUPAC Name: thiamin phosphate
SMILES:CC1([N+](=CSC(CCOP([O-])(=O)[O-])=1)CC2(C=NC(C)=NC(N)=2))
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as thiamine phosphates. These are thiamine derivatives in which the hydroxyl group of the ethanol moiety is substituted by a phosphate group.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organoheterocyclic compounds
Sub ClassDiazines
Direct Parent Thiamine phosphates
Alternative Parents
Substituents
  • Thiamine-phosphate
  • 4,5-disubstituted 1,3-thiazole
  • Aminopyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Primary aromatic amine
  • Alkyl phosphate
  • Imidolactam
  • Thiazole
  • Azole
  • Heteroaromatic compound
  • Azacycle
  • Organic zwitterion
  • Organopnictogen compound
  • Organic oxygen compound
  • Primary amine
  • Amine
  • Organooxygen compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteromonocyclic compound
Molecular Framework Aromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.089 mg/mLALOGPS
logP-1.7ALOGPS
logP-5.7ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.66ChemAxon
pKa (Strongest Basic)5.51ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area125.27 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.15 m3·mol-1ChemAxon
Polarizability32.05 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Not Available
Reactions:
thiamin + ATP → Hydrogen ion + thiamin phosphate + ADP
2-(2-carboxy-4-methylthiazol-5-yl)ethyl phosphate + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + Hydrogen ion → thiamin phosphate + Carbon dioxide + diphosphate
thiamin phosphate + Water → thiamin + phosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
References:
  • Tallaksen CM, Sande A, Bohmer T, Bell H, Karlsen J: Kinetics of thiamin and thiamin phosphate esters in human blood, plasma and urine after 50 mg intravenously or orally. Eur J Clin Pharmacol. 1993;44(1):73-8. [8436160 ]
  • 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. [4055941 ]
  • Lu W, Kimball E, Rabinowitz JD: A high-performance liquid chromatography-tandem mass spectrometry method for quantitation of nitrogen-containing intracellular metabolites. J Am Soc Mass Spectrom. 2006 Jan;17(1):37-50. Epub 2005 Dec 15. [16352439 ]
  • Tallaksen CM, Bohmer T, Bell H, Karlsen J: Concomitant determination of thiamin and its phosphate esters in human blood and serum by high-performance liquid chromatography. J Chromatogr. 1991 Mar 8;564(1):127-36. [1860908 ]
  • Tallaksen CM, Bell H, Bohmer T: Thiamin and thiamin phosphate ester deficiency assessed by high performance liquid chromatography in four clinical cases of Wernicke encephalopathy. Alcohol Clin Exp Res. 1993 Jun;17(3):712-6. [8333605 ]
  • Tallaksen CM, Bohmer T, Bell H: Concentrations of the water-soluble vitamins thiamin, ascorbic acid, and folic acid in serum and cerebrospinal fluid of healthy individuals. Am J Clin Nutr. 1992 Sep;56(3):559-64. [1503069 ]
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
CAS532-40-1
ChEBI37575
ChemSpider13085545
HMDBHMDB02666
IAF126036768
KEGGC01081
MetaboLightsMTBLC37575
PubChem15942892