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Identification
YMDB IDYMDB00381
NameThiamine pyrophosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionThiamine pyrophosphate, also known as thiamin diphosphoric acid or thiamin-ppi, 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 pyrophosphate is a very strong basic compound (based on its pKa). Thiamine pyrophosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • Thaimine pyrophosphate
  • thiamin diphosphate
  • thiamin pyrophosphate
  • thiamin-PPi
  • thiamine diphosphate
  • Thiamine pyrophosphate
  • Thiamine pyrophosphic acid
  • thiamine-PPi
  • thiamine-pyrophosphate
  • ThPP
  • TPP
  • Thiamin diphosphoric acid
  • Thiamin pyrophosphoric acid
  • Thiamine diphosphoric acid
  • Thiamine pyrophosphoric acid
  • Cocarboxylase
  • Berolase
  • Pyrophosphate, thiamine
CAS number154-87-0
WeightAverage: 425.314
Monoisotopic: 425.044967696
InChI KeyAYEKOFBPNLCAJY-UHFFFAOYSA-O
InChIInChI=1S/C12H18N4O7P2S/c1-8-11(3-4-22-25(20,21)23-24(17,18)19)26-7-16(8)6-10-5-14-9(2)15-12(10)13/h5,7H,3-4,6H2,1-2H3,(H4-,13,14,15,17,18,19,20,21)/p+1
IUPAC Name3-[(4-amino-2-methylpyrimidin-5-yl)methyl]-5-(2-{[hydroxy(phosphonooxy)phosphoryl]oxy}ethyl)-4-methyl-1,3-thiazol-3-ium
Traditional IUPAC Namethiamin pyrophosphate
Chemical FormulaC12H19N4O7P2S
SMILES[H]OP(=O)(O[H])O[P@](=O)(O[H])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
  • Organic pyrophosphate
  • 4,5-disubstituted 1,3-thiazole
  • Monoalkyl phosphate
  • Hydropyrimidine
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Alkyl phosphate
  • Imidolactam
  • Thiazole
  • Azole
  • Heteroaromatic compound
  • Azacycle
  • Organic oxide
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic cation
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge1
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.15 g/LALOGPS
logP-1.2ALOGPS
logP-5.8ChemAxon
logS-3.5ALOGPS
pKa (Strongest Acidic)1.78ChemAxon
pKa (Strongest Basic)5.53ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area168.97 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity95.15 m³·mol⁻¹ChemAxon
Polarizability36.96 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
Pyruvate metabolismPW002447 ThumbThumb?image type=greyscaleThumb?image type=simple
TCA CyclePW002377 ThumbThumb?image type=greyscaleThumb?image type=simple
Vitamin B1/Thiamine metabolismPW002486 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Butanoate metabolismec00650 Map00650
Citrate cycle (TCA cycle)ec00020 Map00020
Glycolysis / Gluconeogenesisec00010 Map00010
Pyruvate metabolismec00620 Map00620
Thiamine metabolismec00730 Map00730
SMPDB Reactions
Pyruvic acid + Thiamine pyrophosphateCarbon dioxide + 2-(a-Hydroxyethyl)thiamine diphosphate
2-(a-Hydroxyethyl)thiamine diphosphate + Lipoamide-E ↔ Thiamine pyrophosphate + S-Acetyldihydrolipoamide-E
Thiamine monophosphate + Adenosine triphosphateThiamine pyrophosphate + ADP
Thiamine + Adenosine triphosphatehydron + Adenosine monophosphate + Thiamine pyrophosphate
KEGG ReactionsNot Available
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
  • 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
  • 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
Synthesis Reference:Zabrodskaya, S. V.; Oparin, D. A.; Ostrovskii, Yu. M. Selective synthesis of thiamine diphosphate. Zhurnal Obshchei Khimii (1989), 59(1), 226-7.
External Links:
ResourceLink
CHEBI ID9532
HMDB IDHMDB01372
Pubchem Compound ID1132
Kegg IDC00068
ChemSpider ID73580
FOODB IDFDB022584
WikipediaThiamine_pyrophosphate
BioCyc ID2-(alpha-lactyl)-thpp

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Maintains high levels of reduced glutathione in the cytosol
Gene Name:
GLR1
Uniprot ID:
P41921
Molecular weight:
53440.60156
Reactions
2 glutathione + NADP(+) → glutathione disulfide + NADPH.
General function:
Involved in thiamine diphosphokinase activity
Specific function:
Essential protein, it is the only enzyme in yeast capable of synthesizing thiamine pyrophosphate (TPP)
Gene Name:
THI80
Uniprot ID:
P35202
Molecular weight:
36615.69922
Reactions
ATP + thiamine → AMP + thiamine diphosphate.
General function:
Involved in catalytic activity
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2)
Gene Name:
PDB1
Uniprot ID:
P32473
Molecular weight:
40053.19922
Reactions
Pyruvate + [dihydrolipoyllysine-residue acetyltransferase] lipoyllysine → [dihydrolipoyllysine-residue acetyltransferase] S-acetyldihydrolipoyllysine + CO(2).
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.

Transporters

General function:
Involved in binding
Specific function:
Mitochondrial transporter that mediates uptake of thiamine pyrophosphate (ThPP) into mitochondria
Gene Name:
TPC1
Uniprot ID:
P53257
Molecular weight:
35136.5