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Identification
YMDB IDYMDB00722
Name4-hydroxy-2-oxoglutaric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Hydroxy-2-oxoglutaric acid, also known as 4-hydroxy-2-ketoglutarate or 2-hydroxy-4-oxopentanedioate, belongs to the class of organic compounds 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 an extremely weak basic (essentially neutral) compound (based on its pKa). 4-Hydroxy-2-oxoglutaric acid exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • (+/-)-2-hydroxy-4-oxopentanedioate
  • (+/-)-2-hydroxy-4-oxopentanedioic acid
  • 2-hydroxy-4-oxoglutarate
  • 2-hydroxy-4-oxopentanedioate
  • 2-hydroxy-4-oxopentanedioic acid
  • 2-keto-4-hydroxyglutarate
  • 2-Oxo-4-hydroxyglutarate
  • 4-hydroxy-2-ketoglutarate
  • 4-hydroxy-2-oxoglutarate
  • 4-Hydroxy-2-oxoglutaric acid
  • D-4-hydroxy-2-keto-glutarate
  • D-4-hydroxy-2-ketoglutarate
  • d-4-hydroxy-2-oxoglutarate
  • 2-Keto-4-hydroxyglutarate, (+-)-isomer
CAS number1187-99-1
WeightAverage: 162.0975
Monoisotopic: 162.016437924
InChI KeyWXSKVKPSMAHCSG-UHFFFAOYSA-N
InChIInChI=1S/C5H6O6/c6-2(4(8)9)1-3(7)5(10)11/h2,6H,1H2,(H,8,9)(H,10,11)
IUPAC Name2-hydroxy-4-oxopentanedioic acid
Traditional IUPAC Name4-hydroxy-2-oxoglutaric acid
Chemical FormulaC5H6O6
SMILESOC(CC(=O)C(O)=O)C(O)=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as gamma-keto acids and derivatives. These are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassGamma-keto 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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility69.8 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity30.22 m³·mol⁻¹ChemAxon
Polarizability12.76 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • mitochondrion
  • peroxisome
  • cytoplasm
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Glyoxylate and dicarboxylate metabolismec00630 Map00630
SMPDB ReactionsNot Available
KEGG Reactions
Oxoglutaric acid + erythro-4-hydroxy-L-glutamic acid4-hydroxy-2-oxoglutaric acid + L-Glutamic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
References
References:
  • 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
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID30923
HMDB IDHMDB02070
Pubchem Compound ID599
Kegg IDC01127
ChemSpider ID579
FOODB IDFDB022830
Wikipedia IDNot Available
BioCyc IDD-4-HYDROXY-2-KETO-GLUTARATE

Enzymes

General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol
Gene Name:
AAT1
Uniprot ID:
Q01802
Molecular weight:
51795.10156
Reactions
L-aspartate + 2-oxoglutarate → oxaloacetate + L-glutamate.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Plays a key role in amino acid metabolism
Gene Name:
AAT2
Uniprot ID:
P23542
Molecular weight:
46057.30078
Reactions
L-aspartate + 2-oxoglutarate → oxaloacetate + L-glutamate.