Phosphohydroxypyruvic acid (PAMDB000229)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000229
Identification
Name: Phosphohydroxypyruvic acid
Description:Phosphohydroxypyruvic acid is a prduct of both enzyme phosphoglycerate dehydrogenase [EC 1.1.1.95] and phosphoserine transaminase [EC 2.6.1.52] in glycine, serine and threonine metabolism pathway (KEGG).
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Oxo-3-(phosphonooxy)-Propanoate
  • 2-Oxo-3-(phosphonooxy)-Propanoic acid
  • 3-p-Hydroxy-pyr
  • 3-P-Hydroxypyruvate
  • 3-P-Hydroxypyruvic acid
  • 3-p-OH-pyr
  • 3-p-OH-pyruvate
  • 3-p-OH-pyruvic acid
  • 3-Phosphohydroxy-pyr
  • 3-Phosphohydroxypyruvate
  • 3-Phosphohydroxypyruvic acid
  • 3-Phosphonooxypyruvate
  • 3-Phosphonooxypyruvic acid
  • 3PHPA
  • Phosphohydroxypyruate
  • Phosphohydroxypyruic acid
  • Phosphohydroxypyruvate
  • Phosphohydroxypyruvic acid
Chemical Formula: C3H5O7P
Average Molecular Weight: 184.0414
Monoisotopic Molecular Weight: 183.977289026
InChI Key: LFLUCDOSQPJJBE-UHFFFAOYSA-N
InChI:InChI=1S/C3H5O7P/c4-2(3(5)6)1-10-11(7,8)9/h1H2,(H,5,6)(H2,7,8,9)
CAS number: 3913-50-6
IUPAC Name:2-oxo-3-(phosphonooxy)propanoic acid
Traditional IUPAC Name: phosphohydroxypyruvate
SMILES:OC(=O)C(=O)COP(O)(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbonyl compounds
Sub ClassKetones
Direct Parent Glycerone phosphates
Alternative Parents
Substituents
  • Glycerone phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Monosaccharide
  • Keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-3
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility13.4 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.56 m3·mol-1ChemAxon
Polarizability12.69 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Phosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + Phosphoserine
3-Phosphoglycerate + NAD > Phosphohydroxypyruvic acid + Hydrogen ion + NADH
3-Phospho-D-glycerate + NAD <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion
Phosphohydroxypyruvic acid + Water > Hydroxypyruvic acid + Phosphate
Phosphoserine + Oxoglutaric acid <> Phosphohydroxypyruvic acid + L-Glutamate
3-Phospho-D-glycerate + NAD > Phosphohydroxypyruvic acid + NADH
Phosphoserine + alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine <> Phosphohydroxypyruvic acid + L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
3-Phospho-D-glycerate + NAD + D-2-Hydroxyglutaric acid <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion + alpha-Ketoglutarate
3-Phosphoglyceric acid + NAD + 3-Phosphoglycerate > NADH + Hydrogen ion + Phosphohydroxypyruvic acid
Phosphohydroxypyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + DL-O-Phosphoserine
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0900000000-4411ba8f6713e6b68f94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00s9-0900000000-457227604cff5cdecb73View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05g0-6900000000-5ced177e050ba3272f0fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-003r-3900000000-22820af5ec79da81207bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9300000000-0127ef53c9426c592779View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-4ba77bd112070310c576View in MoNA
References
References:
  • Achouri Y, Rider MH, Schaftingen EV, Robbi M: Cloning, sequencing and expression of rat liver 3-phosphoglycerate dehydrogenase. Biochem J. 1997 Apr 15;323 ( Pt 2):365-70. Pubmed: 9163325
  • 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
  • Thiele I, Swainston N, Fleming RM, Hoppe A, Sahoo S, Aurich MK, Haraldsdottir H, Mo ML, Rolfsson O, Stobbe MD, Thorleifsson SG, Agren R, Bolling C, Bordel S, Chavali AK, Dobson P, Dunn WB, Endler L, Hala D, Hucka M, Hull D, Jameson D, Jamshidi N, Jonsson JJ, Juty N, Keating S, Nookaew I, Le Novere N, Malys N, Mazein A, Papin JA, Price ND, Selkov E Sr, Sigurdsson MI, Simeonidis E, Sonnenschein N, Smallbone K, Sorokin A, van Beek JH, Weichart D, Goryanin I, Nielsen J, Westerhoff HV, Kell DB, Mendes P, Palsson BO: A community-driven global reconstruction of human metabolism. Nat Biotechnol. 2013 Mar 3. doi: 10.1038/nbt.2488. Pubmed: 23455439
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
  • Zhao G, Winkler ME: A novel alpha-ketoglutarate reductase activity of the serA-encoded 3-phosphoglycerate dehydrogenase of Escherichia coli K-12 and its possible implications for human 2-hydroxyglutaric aciduria. J Bacteriol. 1996 Jan;178(1):232-9. Pubmed: 8550422
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID30933
HMDB IDHMDB01024
Pubchem Compound ID105
Kegg IDC03232
ChemSpider ID103
WikipediaPhosphohydroxypyruvic acid
BioCyc ID3-P-HYDROXYPYRUVATE
EcoCyc ID3-P-HYDROXYPYRUVATE
Ligand ExpoHPV

Enzymes

Protein Details
• D-3-phosphoglycerate dehydrogenase
General function:
Involved in amino acid binding
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
serA
Locus Tag:
PA0316
Molecular weight:
44.2 kDa
Reactions
3-phospho-D-glycerate + NAD(+) = 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) = 2-oxoglutarate + NADH.
Protein Details
• Phosphoserine aminotransferase
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. Is involved in both pyridoxine and serine biosynthesis
Gene Name:
serC
Locus Tag:
PA3167
Molecular weight:
39.9 kDa
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.