Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000351
Identification
Name: Hydroxypyruvic acid
Description:Hydroxypyruvic acid is an intermediate in the metabolism of Glycine, serine and threonine. It is a substrate for Serine--pyruvate aminotransferase and Glyoxylate reductase/hydroxypyruvate reductase.
Structure
Thumb
Synonyms:
  • β-hydroxypyruvate
  • β-hydroxypyruvic acid
  • 3-Hydroxy-2-oxopropanoate
  • 3-Hydroxy-2-oxopropanoic acid
  • 3-Hydroxypyruvate
  • 3-Hydroxypyruvic acid
  • b-Hydroxypyruvate
  • b-Hydroxypyruvic acid
  • Beta-Hydroxypyruvate
  • Beta-Hydroxypyruvic acid
  • Hydroxypyruvate
  • OH-pyr
  • OH-pyruvate
  • OH-pyruvic acid
  • β-Hydroxypyruvate
  • β-Hydroxypyruvic acid
Chemical Formula: C3H4O4
Average Molecular Weight: 104.0615
Monoisotopic Molecular Weight: 104.010958616
InChI Key: HHDDCCUIIUWNGJ-UHFFFAOYSA-N
InChI:InChI=1S/C3H4O4/c4-1-2(5)3(6)7/h4H,1H2,(H,6,7)
CAS number: 1113-60-6
IUPAC Name:3-hydroxy-2-oxopropanoic acid
Traditional IUPAC Name: hydroxypyruvic acid
SMILES:OCC(=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as beta hydroxy acids and derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Hydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct Parent Beta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Monosaccharide
  • Keto acid
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-1
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility209.0 mg/mLALOGPS
logP-1.4ALOGPS
logP-0.75ChemAxon
logS0.3ALOGPS
pKa (Strongest Acidic)2.57ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity19.69 m3·mol-1ChemAxon
Polarizability8.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-0iki-3910000000-c702dadd4b10b9c2e21cView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-03ei-8930000000-6f1615bef5d93f87b361View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-9600000000-12ab714e9a2767f1b0b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-9100000000-c1a1da67ff71584bbd6aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-cafdd074d8a05bebf155View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-7900000000-f2aeab79489832ab6fcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0pc0-9200000000-f62ce4a7bd46da93fc09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-1f52435889596b02dbf5View in MoNA
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
  • Kolvraa S, Rasmussen K, Brandt NJ: D-glyceric acidemia: biohcemical studies of a new syndrome. Pediatr Res. 1976 Oct;10(10):825-30. Pubmed: 972784
  • 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
  • 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
Synthesis Reference: Behal, Francis J. Hydroxypyruvic acid formation in Aspergillus niger. Archives of Biochemistry and Biophysics (1960), 88 110-12.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID30841
HMDB IDHMDB01352
Pubchem Compound ID964
Kegg IDC00168
ChemSpider ID939
Wikipedia IDHydroxypyruvic acid
BioCyc IDOH-PYR
EcoCyc IDOH-PYR
Ligand Expo3PY