Record Information
Version2.0
Creation Date2012-05-31 13:55:25 -0600
Update Date2015-06-03 15:54:14 -0600
Secondary Accession Numbers
  • ECMDB02070
Identification
Name:4-Hydroxy-2-oxoglutaric acid
Description:4-hydroxy-2-oxoglutaric acid is a member of the chemical class known as Gamma Keto-Acids and Derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. 4-hydroxy-2-oxoglutaric acid is invovled in Glyoxylate and dicarboxylate metabolism. 2-Keto-4-hydroxyglutarate aldolase also plays a role in respiratory metabolic pathways, which suggests a mechanism for respiration resumption during the termination of the SOS response. (PMID 8524853)
Structure
Thumb
Synonyms:
  • (+/-)-2-hydroxy-4-oxopentanedioate
  • (+/-)-2-hydroxy-4-oxopentanedioic acid
  • 2-Hydroxy-4-oxopentanedioate
  • 2-Hydroxy-4-oxopentanedioic acid
  • 2-k-4-OH-glutarate
  • 2-k-4-OH-glutaric acid
  • 2-Keto-4-hydroxyglutarate
  • 2-Keto-4-hydroxyglutaric acid
  • 2-Oxo-4-hydroxyglutarate
  • 2-Oxo-4-hydroxyglutaric acid
  • 4-Hydroxy-2-ketoglutarate
  • 4-Hydroxy-2-ketoglutaric acid
  • 4-Hydroxy-2-oxoglutarate
  • 4-Hydroxy-2-oxoglutaric acid
  • D-4-HYDROXY-2-KETO-GLUTARATE
  • D-4-HYDROXY-2-keto-glutaric acid
  • D-4-Hydroxy-2-ketoglutarate
  • D-4-Hydroxy-2-ketoglutaric acid
Chemical Formula:C5H6O6
Weight:Average: 162.0975
Monoisotopic: 162.016437924
InChI Key:WXSKVKPSMAHCSG-UHFFFAOYSA-N
InChI:InChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11)
CAS number:Not Available
IUPAC Name:2-hydroxy-4-oxopentanedioic acid
Traditional IUPAC Name:4-hydroxy-2-oxoglutaric acid
SMILES:OC(CC(=O)C(O)=O)C(O)=O
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassKeto acids and derivatives
Direct ParentGamma-keto acids and derivatives
Alternative Parents
Substituents
  • Gamma-keto acid
  • Short-chain keto acid
  • Alpha-hydroxy acid
  • Alpha-keto acid
  • Beta-hydroxy ketone
  • Dicarboxylic acid or derivatives
  • Hydroxy acid
  • Alpha-hydroxy ketone
  • Secondary alcohol
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organooxygen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Organic oxygen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
LogP:-1.249PhysProp
Predicted Properties
PropertyValueSource
Water Solubility69.8 mg/mLALOGPS
logP-1.1ALOGPS
logP-0.82ChemAxon
logS-0.37ALOGPS
pKa (Strongest Acidic)2.45ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area111.9 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.22 m3·mol-1ChemAxon
Polarizability12.76 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:Not Available
KEGG Pathways:
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSsplash10-006x-9100000000-86646efd7b91f9c2b26eView in MoNA
GC-MSGC-MS Spectrum - GC-MS (3 TMS)splash10-03ki-5194000000-f0675d41da8301324b83View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2900000000-fd2a634c0c83321df9f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-6900000000-13f2fbc268a7b1bfe885View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i4-9100000000-ca03fcf215517c709245View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-7b0bd810c920b58daa79View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-9600000000-6734be382dda3c66592aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dm-9000000000-ff1b08ca89e9629f0912View in MoNA
References
References:
  • Cayrol, C., Petit, C., Raynaud, B., Capdevielle, J., Guillemot, J. C., Defais, M. (1995). "Recovery of respiration following the SOS response of Escherichia coli requires RecA-mediated induction of 2-keto-4-hydroxyglutarate aldolase." Proc Natl Acad Sci U S A 92:11806-11809. Pubmed: 8524853
  • 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
  • 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
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID30923
HMDB IDHMDB02070
Pubchem Compound ID599
Kegg IDC01127
ChemSpider ID579
Wikipedia IDNot Available
BioCyc IDD-4-HYDROXY-2-KETO-GLUTARATE
EcoCyc IDD-4-HYDROXY-2-KETO-GLUTARATE

Enzymes

General function:
Involved in catalytic activity
Specific function:
4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate
Gene Name:
eda
Uniprot ID:
P0A955
Molecular weight:
22284
Reactions
4-hydroxy-2-oxoglutarate = pyruvate + glyoxylate.
2-dehydro-3-deoxy-D-gluconate 6-phosphate = pyruvate + D-glyceraldehyde 3-phosphate.