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Identification
YMDB IDYMDB00393
NamePhosphohydroxypyruvic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionPhosphohydroxypyruvic acid, also known as 3-phosphooxypyruvate or hydroxypyruvic acid phosphate, belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position. Phosphohydroxypyruvic acid is a moderately acidic compound (based on its pKa). Phosphohydroxypyruvic acid exists in all living species, ranging from bacteria to humans. Within yeast, phosphohydroxypyruvic acid participates in a number of enzymatic reactions. In particular, phosphohydroxypyruvic acid can be biosynthesized from 3-phosphoglyceric acid; which is mediated by the enzyme 3-phosphoglycerate dehydrogenase. In addition, phosphohydroxypyruvic acid and L-glutamic acid can be converted into oxoglutaric acid and DL-O-phosphoserine; which is catalyzed by the enzyme phosphoserine transaminase. In yeast, phosphohydroxypyruvic acid is involved in the metabolic pathway called the serine metabolism pathway.
Structure
Thumb
Synonyms
  • 2-oxo-3-(phosphonooxy)-Propanoate
  • 2-oxo-3-(phosphonooxy)-Propanoic acid
  • 3-Phosphohydroxypyruvate
  • 3-Phosphohydroxypyruvic acid
  • 3-Phosphonooxypyruvate
  • 3-Phosphonooxypyruvic acid
  • Phosphohydroxypyruvate
  • phosphohydroxypyruvic acid
  • Hydroxypyruvic acid phosphate
  • 3-Phosphooxypyruvate
  • Hydroxypyruvate phosphate
  • Hydroxypyruvic acid phosphoric acid
  • 3-Phosphooxypyruvic acid
  • 3-Phosphonatooxypyruvate
CAS number3913-50-6
WeightAverage: 184.0414
Monoisotopic: 183.977289026
InChI KeyLFLUCDOSQPJJBE-UHFFFAOYSA-N
InChIInChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)
IUPAC Name2-oxo-3-(phosphonooxy)propanoic acid
Traditional IUPAC Namephosphohydroxypyruvate
Chemical FormulaC3H5O7P
SMILES[H]OC(=O)C(=O)C([H])([H])OP(=O)(O[H])O[H]
Chemical Taxonomy
Description belongs to the class of organic compounds known as glycerone phosphates. These are organic compounds containing a glycerone moiety that carries a phosphate group at the O-1 or O-2 position.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentGlycerone phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Monosaccharide
  • Keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxide
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility13.4 g/LALOGPS
logP-1.8ALOGPS
logP-0.87ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.02ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area121.13 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.56 m³·mol⁻¹ChemAxon
Polarizability12.69 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB Pathways
glycine metabolismPW002398 ThumbThumb?image type=greyscaleThumb?image type=simple
serine metabolismPW002402 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Glycine, serine and threonine metabolismec00260 Map00260
Methane metabolismec00680 Map00680
SMPDB Reactions
3-Phosphoglyceric acid + NADNADH + hydron + Phosphohydroxypyruvic acid
Phosphohydroxypyruvic acid + L-Glutamic acidOxoglutaric acid + DL-O-Phosphoserine
KEGG Reactions
NAD + 3-phospho-D-glyceric acidNADH + Phosphohydroxypyruvic acid + hydron
Phosphohydroxypyruvic acid + L-Glutamic acidO-Phospho-L-serine + Oxoglutaric acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9300000000-33ff06735f8214248ea3JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00xr-9510000000-f67b2feb11cbb37fdf47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-4411ba8f6713e6b68f94JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00s9-0900000000-457227604cff5cdecb73JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g0-6900000000-5ced177e050ba3272f0fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-3900000000-22820af5ec79da81207bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-0127ef53c9426c592779JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4ba77bd112070310c576JSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • 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
  • Takada, Y., Noguchi, T. (1985). "Characteristics of alanine: glyoxylate aminotransferase from Saccharomyces cerevisiae, a regulatory enzyme in the glyoxylate pathway of glycine and serine biosynthesis from tricarboxylic acid-cycle intermediates." Biochem J 231:157-163.3933486
  • Belhumeur, P., Fortin, N., Clark, M. W. (1994). "A gene from Saccharomyces cerevisiae which codes for a protein with significant homology to the bacterial 3-phosphoserine aminotransferase." Yeast 10:385-389.8017107
  • Albers, E., Laize, V., Blomberg, A., Hohmann, S., Gustafsson, L. (2003). "Ser3p (Yer081wp) and Ser33p (Yil074cp) are phosphoglycerate dehydrogenases in Saccharomyces cerevisiae." J Biol Chem 278:10264-10272.12525494
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID30933
HMDB IDHMDB01024
Pubchem Compound ID105
Kegg IDC03232
ChemSpider ID103
FOODB IDFDB022377
WikipediaPhosphohydroxypyruvic_acid
BioCyc ID3-P-HYDROXYPYRUVATE

Enzymes

General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
SER33
Uniprot ID:
P40510
Molecular weight:
51187.80078
Reactions
3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.
General function:
Involved in metabolic process
Specific function:
Catalyzes the reversible conversion of 3- phosphohydroxypyruvate to phosphoserine and of 3-hydroxy-2-oxo-4- phosphonooxybutanoate to phosphohydroxythreonine
Gene Name:
SER1
Uniprot ID:
P33330
Molecular weight:
43415.19922
Reactions
O-phospho-L-serine + 2-oxoglutarate → 3-phosphonooxypyruvate + L-glutamate.
4-phosphonooxy-L-threonine + 2-oxoglutarate → (3R)-3-hydroxy-2-oxo-4-phosphonooxybutanoate + L-glutamate.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
SER3
Uniprot ID:
P40054
Molecular weight:
51192.80078
Reactions
3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.