Record Information
Version2.0
Creation Date2012-05-31 13:56:55 -0600
Update Date2015-09-17 15:41:16 -0600
Secondary Accession Numbers
  • ECMDB02666
Identification
Name:Thiamine monophosphate
DescriptionThiamine 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
Weight:Average: 344.327
Monoisotopic: 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
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
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Imidolactam
  • Azole
  • Thiazole
  • Heteroaromatic compound
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organooxygen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
State:Solid
Charge:-1
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility0.046 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity84.27 m³·mol⁻¹ChemAxon
Polarizability32.59 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Adenosine triphosphate + Thiamine monophosphate <> ADP + Thiamine pyrophosphate
Adenosine triphosphate + Thiamine <> ADP + Hydrogen ion + Thiamine monophosphate
Water + Thiamine pyrophosphate > Hydrogen ion + Phosphate + Thiamine monophosphate
2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphate
Adenosine triphosphate + Thiamine <> ADP + Thiamine monophosphate
2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole <> Pyrophosphate + Thiamine monophosphate
2-[(2<i>R</i>,5<i>Z</i>)-(2-carboxy-4-methylthiazol-5(2<i>H</i>)-ylidene]ethyl phosphate + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + Hydrogen ion > Thiamine monophosphate + Carbon dioxide + Pyrophosphate
Thiamine monophosphate + Adenosine triphosphate > Thiamine pyrophosphate + ADP
Hydrogen ion + 4-Methyl-5-(2-phosphoethyl)-thiazole + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate > Thiamine monophosphate + Pyrophosphate
Thiamine + Adenosine triphosphate > Hydrogen ion + Thiamine monophosphate + ADP
2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-Methyl-5-(2-phosphoethyl)-thiazole > Pyrophosphate + Thiamine monophosphate
Adenosine triphosphate + Thiamine > ADP + Thiamine monophosphate
4-amino-2-methyl-5-diphosphomethylpyrimidine + 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + 2 Hydrogen ion + 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate > Thiamine monophosphate + Carbon dioxide + diphosphate + Thiamine monophosphate + Pyrophosphate
Thiamine monophosphate + Adenosine triphosphate + Thiamine monophosphate > Thiamine pyrophosphate + Adenosine diphosphate + ADP
2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + Hydrogen ion > Carbon dioxide + Pyrophosphate + Thiamine monophosphate
2 2-Methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4 4-Methyl-5-(2-phosphoethyl)-thiazole + Hydrogen ion <> Pyrophosphate + Thiamine monophosphate
Adenosine triphosphate + Thiamine monophosphate <> ADP + Thiamine pyrophosphate
SMPDB Pathways:
Thiamin diphosphate biosynthesisPW002028 ThumbThumb?image type=greyscaleThumb?image type=simple
Vitamin B1/ThiaminePW000892 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
  • thiamin diphosphate biosynthesis I (E. coli) PWY-6894
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-00di-0900000000-113c390c4d19be64bd0dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-00ec-9600000000-7ac71f27ba3ca0e2fe91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-00di-0900000000-3cf7f44d89518227c630View in MoNA
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-00di-1900000000-135b9e1aef14efaa6b3eView in MoNA
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-006t-0519000000-8f42bf528fe96c321951View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0930000000-7ae879f5468ac7078781View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0900000000-b2954ab23477c3f8bdbcView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
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

Enzymes

General function:
Involved in hydrolase activity
Specific function:
Catalyzes the hydrolysis of 4-amino-2-methyl-5- hydroxymethylpyrimidine pyrophosphate (HMP-PP) to 4-amino-2- methyl-5-hydroxymethylpyrimidine phosphate (HMP-P), and hydrolysis of thiamine pyrophosphate (TPP) to thiamine monophosphate (TMP). Can hydrolyze other substrates such as MeO-HMP-PP, CF(3)-HMP-PP and MeO-TPP. Is also a non-specific nucleoside tri- and diphosphatase that releases inorganic orthophosphate
Gene Name:
nudJ
Uniprot ID:
P0AEI6
Molecular weight:
17433
General function:
Involved in catalytic activity
Specific function:
ATP + thiamine phosphate = ADP + thiamine diphosphate
Gene Name:
thiL
Uniprot ID:
P0AGG0
Molecular weight:
35070
Reactions
ATP + thiamine phosphate = ADP + thiamine diphosphate.
General function:
Involved in catalytic activity
Specific function:
Condenses 4-methyl-5-(beta-hydroxyethyl)thiazole monophosphate (THZ-P) and 2-methyl-4-amino-5-hydroxymethyl pyrimidine pyrophosphate (HMP-PP) to form thiamine monophosphate (TMP)
Gene Name:
thiE
Uniprot ID:
P30137
Molecular weight:
23015
Reactions
2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-methyl-5-(2-phosphono-oxyethyl)thiazole = diphosphate + thiamine phosphate.
General function:
Involved in transferase activity, transferring phosphorus-containing groups
Specific function:
Catalyzes the phosphorylation of thiamine to thiamine phosphate
Gene Name:
thiK
Uniprot ID:
P75948
Molecular weight:
32397
Reactions
ATP + thiamine = ADP + thiamine phosphate.