Identification
YMDB IDYMDB00153
NameOxoglutaric acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionOxoglutaric acid, also known as oxoglutarate or alpha-ketoglutarate, 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. Oxoglutaric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Oxoglutaric acid exists in all living species, ranging from bacteria to humans. Within yeast, oxoglutaric acid participates in a number of enzymatic reactions. In particular, ornithine and oxoglutaric acid can be converted into L-glutamic acid and L-glutamic γ-semialdehyde; which is mediated by the enzyme ornithine aminotransferase, mitochondrial. In addition, oxoglutaric acid and ammonium can be biosynthesized from L-glutamic acid through the action of the enzyme glutamate dehydrogenase, mitochondrial. In yeast, oxoglutaric acid is involved in the metabolic pathway called the glutamate metabolism pathway. Oxoglutaric acid is a potentially toxic compound.
Structure
Thumb
Synonyms
  • 2-Ketoglutarate
  • 2-Ketoglutaric acid
  • 2-Oxo-1,5-pentanedioate
  • 2-Oxo-1,5-pentanedioic acid
  • 2-Oxoglutarate
  • 2-Oxoglutaric acid
  • 2-Oxopentanedioate
  • 2-Oxopentanedioic acid
  • 2-oxopentanedioic acid, ion(2-)
  • alpha-ketoglutarate
  • Oxoglutarate
  • alpha-Ketoglutaric acid
  • a-Ketoglutarate
  • a-Ketoglutaric acid
  • Α-ketoglutarate
  • Α-ketoglutaric acid
  • alpha-Oxoglutarate
  • Oxogluric acid
  • 2 Oxoglutaric acid
  • Ketoglutaric acid
  • alpha Ketoglutaric acid
  • 2 Ketoglutaric acid
  • alpha Ketoglutarate
  • alpha Oxoglutarate
  • 2 Ketoglutarate
  • 2 Oxoglutarate
  • alpha-Oxoglutaric acid
  • alpha-Oxopentanedioic acid
  • alpha-Keto-glutaric acid
  • Α-oxoglutaric acid
  • Α-oxopentanedioic acid
  • Α-keto-glutaric acid
CAS number328-50-7
WeightAverage: 146.0981
Monoisotopic: 146.021523302
InChI KeyKPGXRSRHYNQIFN-UHFFFAOYSA-N
InChIInChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
IUPAC Name2-oxopentanedioic acid
Traditional IUPAC Nameoxoglutarate
Chemical FormulaC5H6O5
SMILES[H]OC(=O)C(=O)C([H])([H])C([H])([H])C(=O)O[H]
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
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Physical Properties
StateSolid
Charge0
Melting point115.5 °C
Experimental Properties
PropertyValueReference
Water Solubility541.5 mg/mL [Free acid, HMP experimental]PhysProp
LogPNot AvailablePhysProp
Predicted Properties
PropertyValueSource
Water Solubility53.1 g/LALOGPS
logP-0.6ALOGPS
logP-0.11ChemAxon
logS-0.44ALOGPS
pKa (Strongest Acidic)2.66ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area91.67 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.88 m³·mol⁻¹ChemAxon
Polarizability12.17 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Mitochondrion
  • Nucleus
  • Peroxisome
Organoleptic Properties
Flavour/OdourSource
OdorlessFDB003361
SMPDB Pathways
4-aminobutanoate degradationPW002382 ThumbThumb?image type=greyscaleThumb?image type=simple
Asparagine metabolismPW002274 ThumbThumb?image type=greyscaleThumb?image type=simple
Aspartate metabolismPW002375 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid CyclePW000952 ThumbThumb?image type=greyscaleThumb?image type=simple
Citric Acid Cycle 1434561204PW000970 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Taurine and hypotaurine metabolismec00430 Map00430
Tryptophan metabolismec00380 Map00380
Tyrosine metabolismec00350 Map00350
Vitamin B6 metabolismec00750 Map00750
SMPDB Reactions
Alpha-Ketoisovaleric acid + L-Glutamic acidOxoglutaric acid + L-Valine
3-Methylbutanoic acid + L-Glutamic acidOxoglutaric acid + L-Valine
L-Alanine + Oxoglutaric acidPyruvic acid + L-Glutamic acid
Ornithine + Oxoglutaric acidL-Glutamic acid + l-Glutamic-gamma-semialdehyde
L-Glutamic acid + water + NADOxoglutaric acid + Ammonium + NADH + hydron
KEGG Reactions
Phosphohydroxypyruvic acid + L-Glutamic acidO-Phospho-L-serine + Oxoglutaric acid
NAD + water + SaccharopineNADH + Oxoglutaric acid + hydron + L-Lysine
Oxoglutaric acid + Taurine + oxygenSulfite + Carbon dioxide + hydron + aminoacetaldehyde + Succinic acid
Oxoglutaric acid + L-TryptophanL-Glutamic acid + 3-(indol-3-yl)pyruvic acid
L-Glutamic acid + (4-hydroxyphenyl)pyruvic acidL-Tyrosine + Oxoglutaric acid
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
410 ± 195 µM Synthetic medium with 20 g/L glucoseaerobicBaker's yeastPMID: 12584756
5500 ± 500 µM Minimal medium supplemented with ammonia salts and glucoseaerobic;resting cellsBaker's yeastPMID: 4578278
1300 ± 0 µM Minimal medium supplemented with ammonia salts and glucoseanaerobic;resting cellsBaker's yeastPMID: 4578278
10 ± 0 µM Minimal medium supplemented with ammonia salts and galactoseaerobic;growing cellsBaker's yeastPMID: 4578278
2500 ± 2300 µM Minimal medium supplemented with ammonia salts and glucoseaerobic;growing cellsBaker's yeastPMID: 4578278
5000 ± 200 µM Synthetic medium with 2% glucoseaerobic;growing cellsBaker's yeastPMID: 6229402
210 ± 10 µM Synthetic medium with 2% glucoseaerobic;resting cellsBaker's yeastPMID: 6229402
1500 ± 400 µM Synthetic medium with 2% glucoseanaerobic;resting cellsBaker's yeastPMID: 6229402
3700 ± 700 µM Synthetic medium with 2% galactoseaerobic;resting cellsBaker's yeastPMID: 6229402
Conversion Details Here
Extracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
80 ± 24 µM Synthetic medium with 20 g/L glucoseaerobicBaker's yeastPMID: 12584756
Conversion Details Here
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-000b-3910000000-4097b7eb52c2910a4277JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-0002-1910000000-3277227b9c4da4baa1f7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)splash10-00di-9300000000-974bce546caa4fbe6b0fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-000i-9710000000-d0aea11e947b042571f9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-052s-4920000000-bf7ed92c68fd4c8dbb6bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000b-3910000000-4097b7eb52c2910a4277JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-1910000000-3277227b9c4da4baa1f7JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9300000000-974bce546caa4fbe6b0fJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9710000000-d0aea11e947b042571f9JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-052s-4920000000-bf7ed92c68fd4c8dbb6bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000b-2900000000-e514f7afea2490bbe9edJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kfx-9200000000-0ee77a39e9862659f8a7JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00di-9730000000-5e17bd8cfd944963c79fJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, PositiveNot AvailableJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-6900000000-7fc343a243ce5d2a4f39JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9200000000-1a7af9946604baa8b3d2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4l-9800000000-30495b2afdd3526854e7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0925200000-af33449c9638276466c2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-6e43f767847790112b65JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4cacc41705b7b385e91eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-1367eeeb6ad64c67a0aaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000t-0915051100-91cda631ee54800322b8JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-4f842c3673925d29c402JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-5e751351656f6eb62de3JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-7729faa24733fbad77b7JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-c3c62f83bff99f44f7abJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0zfr-6900000000-b6d8379db3e3f1480b14JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-4fde39bb93cde5a27f23JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00i0-9000000000-4343832f3a55842423a9JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a65JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9t-8900000000-b2d3fa8d7ab01a220d9aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9100000000-554bfbd6839bc376cba0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0cJSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0fba-9200000000-4e367c66e94c51eb1a1bJSpectraViewer | MoNA
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
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
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
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  • Roon, R. J., Even, H. L., Larimore, F. (1974). "Glutamate synthase: properties of the reduced nicotinamide adenine dinucleotide-dependent enzyme from Saccharomyces cerevisiae." J Bacteriol 118:89-95.4362465
  • Takada, Y., Noguchi, T. (1985). "Characteristics of alanine: glyoxylate aminotransferase from Saccharomyces cerevisiae, a regulatory enzyme in the glyoxylate pathway of glycine and serine biosynthesis from tricarboxylic acid-cycle intermediates." Biochem J 231:157-163.3933486
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  • Moreira dos Santos, M., Thygesen, G., Kotter, P., Olsson, L., Nielsen, J. (2003). "Aerobic physiology of redox-engineered Saccharomyces cerevisiae strains modified in the ammonium assimilation for increased NADPH availability." FEMS Yeast Res 4:59-68.14554197
  • Hogan, D. A., Auchtung, T. A., Hausinger, R. P. (1999). "Cloning and characterization of a sulfonate/alpha-ketoglutarate dioxygenase from Saccharomyces cerevisiae." J Bacteriol 181:5876-5879.10482536
  • Bhattacharjee, J. K. (1985). "alpha-Aminoadipate pathway for the biosynthesis of lysine in lower eukaryotes." Crit Rev Microbiol 12:131-151.3928261
  • Cupp, J. R., McAlister-Henn, L. (1992). "Cloning and characterization of the gene encoding the IDH1 subunit of NAD(+)-dependent isocitrate dehydrogenase from Saccharomyces cerevisiae." J Biol Chem 267:16417-16423.1644826
  • Verleur, N., Elgersma, Y., Van Roermund, C. W., Tabak, H. F., Wanders, R. J. (1997). "Cytosolic aspartate aminotransferase encoded by the AAT2 gene is targeted to the peroxisomes in oleate-grown Saccharomyces cerevisiae." Eur J Biochem 247:972-980.9288922
  • Dickinson, J. R., Harrison, S. J., Hewlins, M. J. (1998). "An investigation of the metabolism of valine to isobutyl alcohol in Saccharomyces cerevisiae." J Biol Chem 273:25751-25756.9748245
  • Belhumeur, P., Fortin, N., Clark, M. W. (1994). "A gene from Saccharomyces cerevisiae which codes for a protein with significant homology to the bacterial 3-phosphoserine aminotransferase." Yeast 10:385-389.8017107
  • Minard, K. I., Jennings, G. T., Loftus, T. M., Xuan, D., McAlister-Henn, L. (1998). "Sources of NADPH and expression of mammalian NADP+-specific isocitrate dehydrogenases in Saccharomyces cerevisiae." J Biol Chem 273:31486-31493.9813062
  • Przybyla-Zawislak, B., Gadde, D. M., Ducharme, K., McCammon, M. T. (1999). "Genetic and biochemical interactions involving tricarboxylic acid cycle (TCA) function using a collection of mutants defective in all TCA cycle genes." Genetics 152:153-166.10224250
  • Valenzuela, L., Ballario, P., Aranda, C., Filetici, P., Gonzalez, A. (1998). "Regulation of expression of GLT1, the gene encoding glutamate synthase in Saccharomyces cerevisiae." J Bacteriol 180:3533-3540.9657994
  • Iraqui, I., Vissers, S., Cartiaux, M., Urrestarazu, A. (1998). "Characterisation of Saccharomyces cerevisiae ARO8 and ARO9 genes encoding aromatic aminotransferases I and II reveals a new aminotransferase subfamily." Mol Gen Genet 257:238-248.9491083
  • Kispal, G., Steiner, H., Court, D. A., Rolinski, B., Lill, R. (1996). "Mitochondrial and cytosolic branched-chain amino acid transaminases from yeast, homologs of the myc oncogene-regulated Eca39 protein." J Biol Chem 271:24458-24464.8798704
  • Boer, V. M., Crutchfield, C. A., Bradley, P. H., Botstein, D., Rabinowitz, J. D. (2010). "Growth-limiting intracellular metabolites in yeast growing under diverse nutrient limitations." Mol Biol Cell 21:198-211.19889834
  • Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
  • Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Tanaka, Katsunobu; kimura, Kazu; Yamaguchi, Ken. Fermentative production of a-oxoglutaric acid. U.S. (1973), 4 pp.
External Links:
ResourceLink
CHEBI ID30915
HMDB IDHMDB00208
Pubchem Compound ID51
Kegg IDC00026
ChemSpider ID50
FOODB IDFDB003361
WikipediaAlpha-Ketoglutaric_acid
BioCyc ID2-KETOGLUTARATE

Enzymes

General function:
Involved in catalytic activity
Specific function:
Forms L-glutamate from L-glutamine and 2-oxoglutarate. Represents an alternative pathway to L-glutamate dehydrogenase for the biosynthesis of L-glutamate. Participates with glutamine synthetase in ammonia assimilation processes. The enzyme is specific for NADH, L-glutamine and 2-oxoglutarate
Gene Name:
GLT1
Uniprot ID:
Q12680
Molecular weight:
238100.0
Reactions
2 L-glutamate + NAD(+) → L-glutamine + 2-oxoglutarate + NADH.
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L- tryptophan metabolite L-kynurenine to form kynurenic acid (KA)
Gene Name:
BNA3
Uniprot ID:
P47039
Molecular weight:
50081.89844
Reactions
L-kynurenine + 2-oxoglutarate → 4-(2-aminophenyl)-2,4-dioxobutanoate + L-glutamate.
General function:
Involved in oxidoreductase activity
Specific function:
Lipoamide dehydrogenase is a component of the alpha- ketoacid dehydrogenase complexes. This includes the pyruvate dehydrogenase complex, which catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2). Acts also as component of the glycine cleavage system (glycine decarboxylase complex), which catalyzes the degradation of glycine
Gene Name:
LPD1
Uniprot ID:
P09624
Molecular weight:
54009.69922
Reactions
Protein N(6)-(dihydrolipoyl)lysine + NAD(+) → protein N(6)-(lipoyl)lysine + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the NAD(+)-dependent cleavage of saccharopine to L-lysine and 2-oxoglutarate
Gene Name:
LYS1
Uniprot ID:
P38998
Molecular weight:
41464.39844
Reactions
N(6)-(L-1,3-dicarboxypropyl)-L-lysine + NAD(+) + H(2)O → L-lysine + 2-oxoglutarate + NADH.
General function:
Involved in magnesium ion binding
Specific function:
Performs an essential role in the oxidative function of the citric acid cycle. Also binds RNA; specifically to the 5'- untranslated leaders of mitochondrial mRNAs
Gene Name:
IDH1
Uniprot ID:
P28834
Molecular weight:
39323.69922
Reactions
Isocitrate + NAD(+) → 2-oxoglutarate + CO(2) + NADH.
General function:
Involved in magnesium ion binding
Specific function:
Performs an essential role in the oxidative function of the citric acid cycle. Also binds RNA; specifically to the 5'- untranslated leaders of mitochondrial mRNAs
Gene Name:
IDH2
Uniprot ID:
P28241
Molecular weight:
39739.0
Reactions
Isocitrate + NAD(+) → 2-oxoglutarate + CO(2) + NADH.
General function:
Involved in magnesium ion binding
Specific function:
May function in the production of NADPH for fatty acid and sterol synthesis
Gene Name:
IDP3
Uniprot ID:
P53982
Molecular weight:
47856.0
Reactions
Isocitrate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
Oxalosuccinate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
General function:
Involved in magnesium ion binding
Specific function:
Mitochondrial IDP1 may regulate flux through the tricarboxylic acid cycle and respiration. Its probably critical function is the production of NADPH
Gene Name:
IDP1
Uniprot ID:
P21954
Molecular weight:
48189.89844
Reactions
Isocitrate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
Oxalosuccinate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
General function:
Involved in magnesium ion binding
Specific function:
May function in the production of NADPH for fatty acid and sterol synthesis
Gene Name:
IDP2
Uniprot ID:
P41939
Molecular weight:
46561.89844
Reactions
Isocitrate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
Oxalosuccinate + NADP(+) → 2-oxoglutarate + CO(2) + NADPH.
General function:
Involved in transaminase activity
Specific function:
N(2)-acetyl-L-ornithine + 2-oxoglutarate = N- acetyl-L-glutamate 5-semialdehyde + L-glutamate
Gene Name:
ARG8
Uniprot ID:
P18544
Molecular weight:
46681.10156
Reactions
N(2)-acetyl-L-ornithine + 2-oxoglutarate → N-acetyl-L-glutamate 5-semialdehyde + L-glutamate.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. Involved in cell cycle regulation
Gene Name:
BAT2
Uniprot ID:
P47176
Molecular weight:
41624.39844
Reactions
L-leucine + 2-oxoglutarate → 4-methyl-2-oxopentanoate + L-glutamate.
2-oxoglutaric acid + L-isoleucine → (S)-3-methyl-2-oxopentanoic acid + L-glutamic acid.
2-oxoglutaric acid + L-valine → 3-methyl-2-oxobutanoic acid + L-glutamic acid.
General function:
Involved in catalytic activity
Specific function:
Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. Appears to be involved in the regulation of the transition from G1 to S phase in the cell cycle. High copy suppressor of a temperature-sensitive mutation in the ABC transporter, ATM1
Gene Name:
BAT1
Uniprot ID:
P38891
Molecular weight:
43595.69922
Reactions
L-leucine + 2-oxoglutarate → 4-methyl-2-oxopentanoate + L-glutamate.
2-oxoglutaric acid + L-isoleucine → (S)-3-methyl-2-oxopentanoic acid + L-glutamic acid.
2-oxoglutaric acid + L-valine → 3-methyl-2-oxobutanoic acid + L-glutamic acid.
General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Acetyl-CoA + H(2)O + 2-oxoglutarate = (R)-2- hydroxybutane-1,2,4-tricarboxylate + CoA
Gene Name:
LYS21
Uniprot ID:
Q12122
Molecular weight:
48593.80078
Reactions
Acetyl-CoA + H(2)O + 2-oxoglutarate → (R)-2-hydroxybutane-1,2,4-tricarboxylate + CoA.
General function:
Involved in transferase activity, transferring acyl groups, acyl groups converted into alkyl on transfer
Specific function:
Acetyl-CoA + H(2)O + 2-oxoglutarate = (R)-2- hydroxybutane-1,2,4-tricarboxylate + CoA
Gene Name:
LYS20
Uniprot ID:
P48570
Molecular weight:
47098.39844
Reactions
Acetyl-CoA + H(2)O + 2-oxoglutarate → (R)-2-hydroxybutane-1,2,4-tricarboxylate + CoA.
General function:
Involved in acyltransferase activity
Specific function:
The pyruvate dehydrogenase complex catalyzes the overall conversion of pyruvate to acetyl-CoA and CO(2)
Gene Name:
PDA2
Uniprot ID:
P12695
Molecular weight:
51817.5
Reactions
Acetyl-CoA + enzyme N(6)-(dihydrolipoyl)lysine → CoA + enzyme N(6)-(S-acetyldihydrolipoyl)lysine.
General function:
Involved in oxidoreductase activity
Specific function:
Maintains high levels of reduced glutathione in the cytosol
Gene Name:
GLR1
Uniprot ID:
P41921
Molecular weight:
53440.60156
Reactions
2 glutathione + NADP(+) → glutathione disulfide + NADPH.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
SER33
Uniprot ID:
P40510
Molecular weight:
51187.80078
Reactions
3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.
General function:
Involved in transferase activity
Specific function:
L-histidinol phosphate + 2-oxoglutarate = 3- (imidazol-4-yl)-2-oxopropyl phosphate + L-glutamate
Gene Name:
HIS5
Uniprot ID:
P07172
Molecular weight:
42645.69922
Reactions
L-histidinol phosphate + 2-oxoglutarate → 3-(imidazol-4-yl)-2-oxopropyl phosphate + L-glutamate.
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
Gene Name:
SER1
Uniprot ID:
P33330
Molecular weight:
43415.19922
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.
General function:
Involved in oxidoreductase activity
Specific function:
L-glutamate + H(2)O + NAD(+) = 2-oxoglutarate + NH(3) + NADH
Gene Name:
GDH2
Uniprot ID:
P33327
Molecular weight:
124331.0
Reactions
L-glutamate + H(2)O + NAD(+) → 2-oxoglutarate + NH(3) + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
L-glutamate + H(2)O + NADP(+) = 2-oxoglutarate + NH(3) + NADPH
Gene Name:
GDH3
Uniprot ID:
P39708
Molecular weight:
49626.80078
Reactions
L-glutamate + H(2)O + NADP(+) → 2-oxoglutarate + NH(3) + NADPH.
General function:
Involved in oxidoreductase activity
Specific function:
L-glutamate + H(2)O + NADP(+) = 2-oxoglutarate + NH(3) + NADPH
Gene Name:
GDH1
Uniprot ID:
P07262
Molecular weight:
49569.60156
Reactions
L-glutamate + H(2)O + NADP(+) → 2-oxoglutarate + NH(3) + NADPH.
General function:
Involved in magnesium ion binding
Specific function:
Catalyzes the NAD(+)-dependent conversion of homoisocitrate to alpha-ketoadipate
Gene Name:
LYS12
Uniprot ID:
P40495
Molecular weight:
40068.60156
Reactions
(1R,2S)-1-hydroxybutane-1,2,4-tricarboxylate + NAD(+) → 2-oxoadipate + CO(2) + NADH.
General function:
Involved in oxidoreductase activity
Specific function:
Acts as a alpha-ketoglutarate-dependent dioxygenase active on sulfonates. Although taurine is a poor substrate, a variety of other sulfonates are utilized, with the best natural substrates being isethionate and taurocholate
Gene Name:
JLP1
Uniprot ID:
Q12358
Molecular weight:
46982.30078
Reactions
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity and kynurenine aminotransferase activity
Gene Name:
ARO9
Uniprot ID:
P38840
Molecular weight:
58527.0
Reactions
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Has aromatic amino acid transaminase activity. Also active with methionine, alpha-aminoadipate and leucine when phenylpyruvate is the amino acceptor
Gene Name:
ARO8
Uniprot ID:
P53090
Molecular weight:
56177.30078
Reactions
An aromatic amino acid + 2-oxoglutarate → an aromatic oxo acid + L-glutamate.
L-2-aminoadipate + 2-oxoglutarate → 2-oxoadipate + L-glutamate
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 oxoglutarate dehydrogenase (succinyl-transferring) activity
Specific function:
The 2-oxoglutarate dehydrogenase complex catalyzes the overall conversion of 2-oxoglutarate to succinyl-CoA and CO(2). It contains multiple copies of three enzymatic components:2- oxoglutarate dehydrogenase (E1), dihydrolipoamide succinyltransferase (E2) and lipoamide dehydrogenase (E3)
Gene Name:
KGD1
Uniprot ID:
P20967
Molecular weight:
114416.0
Reactions
2-oxoglutarate + [dihydrolipoyllysine-residue succinyltransferase] lipoyllysine → [dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine + CO(2).
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.
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
L-alanine + 2-oxoglutarate = pyruvate + L- glutamate
Gene Name:
ALT2
Uniprot ID:
P52892
Molecular weight:
56769.30078
Reactions
L-alanine + 2-oxoglutarate → pyruvate + L-glutamate.
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
Required for the degradation of gamma-aminobutyric acid (GABA), which is important for utilization of GABA as nitrogen source and for oxidative stress tolerance. Deaminates GABA to succinate semialdehyde, which in turn is converted to succinate by the succinate-semialdehyde dehydrogenase UGA2. Cannot transaminate beta-alanine (BAL)
Gene Name:
UGA1
Uniprot ID:
P17649
Molecular weight:
52945.69922
Reactions
4-aminobutanoate + 2-oxoglutarate → succinate semialdehyde + L-glutamate.
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
L-alanine + 2-oxoglutarate = pyruvate + L- glutamate
Gene Name:
ALT1
Uniprot ID:
P52893
Molecular weight:
66421.10156
Reactions
L-alanine + 2-oxoglutarate → pyruvate + L-glutamate.
General function:
Involved in transaminase activity
Specific function:
L-ornithine + a 2-oxo acid = L-glutamate 5- semialdehyde + an L-amino acid
Gene Name:
CAR2
Uniprot ID:
P07991
Molecular weight:
46085.60156
Reactions
L-ornithine + a 2-oxo acid → L-glutamate 5-semialdehyde + an L-amino acid.
General function:
Involved in oxidoreductase activity, acting on the CH-OH group of donors, NAD or NADP as acceptor
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
SER3
Uniprot ID:
P40054
Molecular weight:
51192.80078
Reactions
3-phospho-D-glycerate + NAD(+) → 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) → 2-oxoglutarate + NADH.

Transporters

General function:
Involved in transporter activity
Specific function:
Transports C5-C7 oxodicarboxylates across the inner membranes of mitochondria. Can transport 2-oxoadipate, 2- oxoglutarate, adipate, glutarate, 2-oxopimelate, oxaloacetate, citrate and malate. The main physiological role is probably to supply 2-oxoadipate and 2-oxoglutarate from the mitochondrial matrix to the cytosol where they are used in the biosynthesis of lysine and glutamate, respectively, and in lysine catabolism
Gene Name:
ODC2
Uniprot ID:
Q99297
Molecular weight:
34006.69922
General function:
Involved in transporter activity
Specific function:
Transports C5-C7 oxodicarboxylates across the inner membranes of mitochondria. Can transport 2-oxoadipate, 2- oxoglutarate, adipate, glutarate, 2-oxopimelate, oxaloacetate, citrate and malate. The main physiological role is probably to supply 2-oxoadipate and 2-oxoglutarate from the mitochondrial matrix to the cytosol where they are used in the biosynthesis of lysine and glutamate, respectively, and in lysine catabolism
Gene Name:
ODC1
Uniprot ID:
Q03028
Molecular weight:
34206.0