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Identification
YMDB IDYMDB00164
NameThiamine monophosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionThiamine monophosphate, also known as thiamin phosphoric acid or monophosphothiaminum, 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 monophosphate is a very strong basic compound (based on its pKa). Thiamine monophosphate exists in all eukaryotes, ranging from yeast to humans. Within yeast, thiamine monophosphate participates in a number of enzymatic reactions. In particular, thiamine monophosphate can be biosynthesized from 2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate and 4-methyl-5-(2-phosphonooxyethyl)thiazole; which is mediated by the enzyme thiamine biosynthetic bifunctional enzyme. In addition, thiamine monophosphate can be converted into thiamine through the action of the enzyme acid phosphatases. In yeast, thiamine monophosphate is involved in the metabolic pathway called the vitamin b1/thiamine metabolism pathway.
Structure
Thumb
Synonyms
  • Aneurin-monophosphorsaeureester
  • Aneurine monophosphate
  • Monofosfotiamina
  • Monophosphoric ester of thiamine
  • Monophosphothiamine
  • Monophosphothiaminum
  • Phosphothiaminum
  • Thiamin dihydrogenphosphate
  • thiamin monophosphate
  • Thiamin phosphate
  • Thiamine monophosphate
  • Thiamine monophosphate dihydrate
  • Thiamine monophosphic acid
  • thiamine phosphate
  • Tiamina monofosfato
  • TMP
  • tmp, thiamin phosphate
  • THIAMIN phosphoric acid
  • Thiamine monophosphoric acid
  • monoPhosphate, thiamine
  • Phosphoester, thiamine
  • Thiamine phosphoester
CAS number495-23-8
WeightAverage: 344.327
Monoisotopic: 344.070812254
InChI KeyHZSAJDVWZRBGIF-UHFFFAOYSA-N
InChIInChI=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)
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-[2-(hydrogen phosphonatooxy)ethyl]-4-methyl-1,3-thiazol-3-ium
Traditional IUPAC Namethiamin phosphate
Chemical FormulaC12H17N4O4PS
SMILES[H]OP([O-])(=O)OC([H])([H])C([H])([H])C1=C([N+](=C([H])S1)C([H])([H])C1=C([H])N=C(N=C1N([H])[H])C([H])([H])[H])C([H])([H])[H]
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
  • 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 zwitterion
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.089 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity83.15 m³·mol⁻¹ChemAxon
Polarizability32.05 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Organoleptic PropertiesNot Available
SMPDB Pathways
Vitamin B1/Thiamine metabolismPW002486 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Thiamine metabolismec00730 Map00730
SMPDB Reactions
4-amino-2-methyl-5-diphosphomethylpyrimidine + 2-((2R,5Z)-2-Carboxy-4-methylthiazol-5(2H)-ylidene)ethyl phosphate + hydronThiamine monophosphate + Carbon dioxide + diphosphate
Thiamine monophosphate + Adenosine triphosphateThiamine pyrophosphate + ADP
4-amino-2-methyl-5-diphosphomethylpyrimidine + hydron + 4-methyl-5-(2-phosphonooxyethyl)thiazole → Pyrophosphate + Thiamine monophosphate
Thiamine monophosphate + waterThiamine + phosphate
KEGG Reactions
Thiamine monophosphate + waterThiamine + phosphate
Thiamine monophosphate + water Thiamine + phosphate
4-Methyl-5-(2-phosphonooxyethyl)thiazole + hydron + 4-amino-2-methyl-5-diphosphomethylpyrimidinePyrophosphate + Thiamine monophosphate
Adenosine triphosphate + Thiamine monophosphatethiamine(1+) diphosphate(1-) + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Onozuka, M., Konno, H., Kawasaki, Y., Akaji, K., Nosaka, K. (2008). "Involvement of thiaminase II encoded by the THI20 gene in thiamin salvage of Saccharomyces cerevisiae." FEMS Yeast Res 8:266-275.18028398
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
Synthesis Reference:Leder, Irwin G. Enzymic synthesis of thiamine monophosphate. Journal of Biological Chemistry (1961), 236 3066-71.
External Links:
ResourceLink
CHEBI ID37574
HMDB IDHMDB02666
Pubchem Compound ID1131
Kegg IDC01081
ChemSpider ID2627905
FOODB IDFDB023043
WikipediaThiamine_monophosphate
BioCyc IDTHIAMINE-P

Enzymes

General function:
Involved in acid phosphatase activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
PHO11
Uniprot ID:
P35842
Molecular weight:
52757.39844
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
General function:
Involved in acid phosphatase activity
Specific function:
Partially mediates extracellular nucleotide derived phosphate hydrolysis along with NPP1 and NPP2
Gene Name:
PHO5
Uniprot ID:
P00635
Molecular weight:
52858.10156
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
General function:
Involved in catalytic activity
Specific function:
Essential for thiamine biosynthesis. The kinase activity is involved in the salvage synthesis of TH-P from the thiazole
Gene Name:
THI6
Uniprot ID:
P41835
Molecular weight:
58058.19922
Reactions
2-methyl-4-amino-5-hydroxymethylpyrimidine diphosphate + 4-methyl-5-(2-phosphono-oxyethyl)thiazole → diphosphate + thiamine phosphate.
ATP + 4-methyl-5-(2-hydroxyethyl)thiazole → ADP + 4-methyl-5-(2-phosphonooxyethyl)thiazole.
General function:
Involved in acid phosphatase activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
PHO3
Uniprot ID:
P24031
Molecular weight:
52776.10156
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.
General function:
Involved in acid phosphatase activity
Specific function:
A phosphate monoester + H(2)O = an alcohol + phosphate
Gene Name:
PHO12
Uniprot ID:
P38693
Molecular weight:
52699.30078
Reactions
A phosphate monoester + H(2)O → an alcohol + phosphate.