4-hydroxy-2-oxoglutaric acid (YMDB00722)

Identification
YMDB IDYMDB00722
Name4-hydroxy-2-oxoglutaric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description4-Hydroxy-2-oxoglutaric acid, also known as 2-keto-4-hydroxyglutarate, 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 exists in all living species, ranging from bacteria to plants to humans. Based on a literature review very few articles have been published on 4-Hydroxy-2-oxoglutaric acid.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
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 acid → 4-hydroxy-2-oxoglutaric acid + L-Glutamic acid
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9100000000-86646efd7b91f9c2b26eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-03ki-5194000000-f0675d41da8301324b83JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-2900000000-fd2a634c0c83321df9f8JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-6900000000-13f2fbc268a7b1bfe885JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-05i4-9100000000-ca03fcf215517c709245JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-2900000000-7b0bd810c920b58daa79JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00xs-9600000000-6734be382dda3c66592aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dm-9000000000-ff1b08ca89e9629f0912JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kb-6900000000-661f455fd4b6e8da0c82JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dm-9100000000-b9bce861b26dd8001332JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-a0587223ecf12202531fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014j-5900000000-30fe0301167b3cea2c0bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006t-9000000000-5bbf6f8b15e9a3af889bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-e7768f77ba36e7e3743bJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
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

Protein Details
1. Aspartate aminotransferase, mitochondrial
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.
Protein Details
2. Aspartate aminotransferase, cytoplasmic
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.