Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000623
Identification
Name: Oxoglutaric acid
Description:Alpha-ketoglutaric acid is an important biological compound and is a key intermediate in the Krebs cycle. Alpha-ketoglutaric acid occurs naturally within cells. One of its functions is to combine with ammonia to form glutamic acid and then glutamine. Another function is to combine with nitrogen released in the cell, therefore preventing nitrogen overload. (wikipedia)
Structure
Thumb
Synonyms:
  • α-ketoglutarate
  • α-ketoglutaric acid
  • α-oxoglutarate
  • α-oxoglutaric acid
  • 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-Oxopentanedionate
  • 2-Oxopentanedionic acid
  • A-Ketoglutarate
  • A-Ketoglutaric acid
  • a-Oxoglutarate
  • a-Oxoglutaric acid
  • Alpha-Ketoglutarate
  • Alpha-Ketoglutaric acid
  • Alpha-Oxoglutarate
  • Alpha-Oxoglutaric acid
  • Ketoglutarate
  • Ketoglutaric acid
  • Oxoglutarate
  • α-Ketoglutarate
  • α-Ketoglutaric acid
  • α-Oxoglutarate
  • α-Oxoglutaric acid
Chemical Formula: C5H6O5
Average Molecular Weight: 146.0981
Monoisotopic Molecular Weight: 146.021523302
InChI Key: KPGXRSRHYNQIFN-UHFFFAOYSA-N
InChI:InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)
CAS number: 328-50-7
IUPAC Name:2-oxopentanedioic acid
Traditional IUPAC Name: oxoglutarate
SMILES:OC(=O)CCC(=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound 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.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Keto acids and derivatives
Sub ClassGamma-keto acids and derivatives
Direct Parent Gamma-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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: 115.5 °C
Experimental Properties:
PropertyValueSource
Water Solubility:541.5 mg/mL [Free acid, HMP experimental]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility53.1 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity28.88 m3·mol-1ChemAxon
Polarizability12.17 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Oxoglutaric acid + Coenzyme A + NAD > Succinyl-CoA + Carbon dioxide + NADH
Hydrogen ion + Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide
Oxoglutaric acid + kynurenine L-Glutamate + 4-(2-aminophenyl)-2,4-dioxobutanoate
N-Acetylornithine + Oxoglutaric acid < N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
Oxoglutaric acid + L-Alanine <> L-Glutamate + Pyruvic acid
L-Aspartic acid + Oxoglutaric acid <> Oxalacetic acid + L-Glutamate
L-Isoleucine + Oxoglutaric acid <> 3-Methyl-2-oxovaleric acid + L-Glutamate
L-Leucine + Oxoglutaric acid <> Ketoleucine + L-Glutamate
L-Valine + Oxoglutaric acid <> alpha-Ketoisovaleric acid + L-Glutamate
Oxoglutaric acid + L-Cysteine > L-Glutamate + 3-Mercaptopyruvic acid
an aliphatic &alpha;,&omega;-diamine + Oxoglutaric acid <> an aliphatic &omega;-aminoaldehyde + L-Glutamate
Oxoglutaric acid + gamma-Aminobutyric acid <> L-Glutamate + Succinic acid semialdehyde
L-Glutamate + NADP < Hydrogen ion + L-Glutamine + Oxoglutaric acid + NADPH
L-Glutamate + Water + NADP <> Hydrogen ion + Oxoglutaric acid + Ammonia + NADPH
Imidazole acetol-phosphate + L-Glutamate <> Histidinol phosphate + Oxoglutaric acid
Isocitric acid + NADP > NADPH + Oxoglutaric acid + Carbon dioxide
Phenylpyruvic acid + L-Glutamate <> L-Phenylalanine + Oxoglutaric acid
Phosphoserine + Oxoglutaric acid <> Phosphohydroxypyruvic acid + L-Glutamate
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
Putrescine + Oxoglutaric acid <> 4-Aminobutyraldehyde + L-Glutamate
Pyridoxamine 5'-phosphate + Oxoglutaric acid <> Pyridoxal 5'-phosphate + D-Glutamic acid
4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate <> dTDP-D-Fucosamine + Oxoglutaric acid
a methylated nucleobase within DNA + Oxygen + Oxoglutaric acid Hydrogen ion + a nucleobase within DNA + Carbon dioxide + Formaldehyde + Succinic acid
Oxalosuccinic acid + Hydrogen ion > Oxoglutaric acid + Carbon dioxide
2-hydroxyglutarate + NAD <> Hydrogen ion + Oxoglutaric acid + NADH
Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose + Oxoglutaric acid <> UDP-4-Keto-pyranose + L-Glutamate
Taurine + Oxoglutaric acid + Oxygen > Hydrogen ion + Aminoacetaldehyde + Sulfite + Succinic acid + Carbon dioxide
L-2-Hydroxyglutaric acid + Oxygen > Oxoglutaric acid + Hydrogen peroxide
N1-Methyladenine + Oxygen + Oxoglutaric acid > Hydrogen ion + Adenine + Carbon dioxide + Formaldehyde + Succinic acid
N3-Methylcytosine + Oxygen + Oxoglutaric acid > Hydrogen ion + Cytosine + Carbon dioxide + Formaldehyde + Succinic acid
1-Ethyladenine + Oxygen + Oxoglutaric acid > Adenine + Carbon dioxide + Acetaldehyde + Succinic acid
Oxoglutaric acid + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate
N2-Succinyl-L-ornithine + Oxoglutaric acid > N2-Succinyl-L-glutamic acid 5-semialdehyde + L-Glutamate
L-Tyrosine + Oxoglutaric acid <> 4-Hydroxyphenylpyruvic acid + L-Glutamate
DNA-base-CH(3) + Oxoglutaric acid + Oxygen > DNA-base + Formaldehyde + Succinic acid + Carbon dioxide
L-Glutamate + Water + NADP > Oxoglutaric acid + Ammonia + NADPH
(S)-b-aminoisobutyric acid + Oxoglutaric acid > 2-Methyl-3-oxopropanoate + L-Glutamate
2 L-Glutamate + NADP > L-Glutamine + Oxoglutaric acid + NADPH
L-Valine + Oxoglutaric acid > a-Ketoisovaleric acid + L-Glutamate
Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide
Oxoglutaric acid + [dihydrolipoyllysine-residue succinyltransferase] lipoyllysine > [dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine + Carbon dioxide
Putrescine + Oxoglutaric acid > L-Glutamate + 1-Pyrroline + Water
D-2-Hydroxyglutaric acid + NAD > Oxoglutaric acid + NADH
Taurine + Oxoglutaric acid + Oxygen > Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide
An aromatic amino acid + Oxoglutaric acid > an aromatic oxo acid + L-Glutamate
Ammonia + L-Glutamic acid + Adenosine triphosphate + Oxoglutaric acid + L-Glutamate <> Phosphate + L-Glutamine + Adenosine diphosphate + ADP
Oxoglutaric acid + NADPH + Ammonium + Hydrogen ion + NADPH > L-Glutamic acid + Water + NADP + L-Glutamate
2 L-Glutamic acid + NADP + 2 L-Glutamate > L-Glutamine + NADPH + Hydrogen ion + Oxoglutaric acid + NADPH
N-Succinyl-2-amino-6-ketopimelate + L-Glutamic acid + L-Glutamate > N-Succinyl-L,L-2,6-diaminopimelate + Oxoglutaric acid
Taurine + Oxoglutaric acid + Oxygen > Sulfite + Succinic acid + Aminoacetaldehyde + Carbon dioxide + Sulfite
Taurine + Oxoglutaric acid + Oxygen > Sulfite + Succinic acid + Carbon dioxide + Hydrogen ion + Aminoacetaldehyde + Sulfite
Isocitric acid + NAD + Isocitric acid > Oxoglutaric acid + Carbon dioxide + NADH + Hydrogen ion
D-threo-Isocitric acid + NADP > Carbon dioxide + NADPH + Oxoglutaric acid + NADPH
Oxoglutaric acid + NAD + Coenzyme A > Succinyl-CoA + NADH + Hydrogen ion + Carbon dioxide + Succinyl-CoA
L-Alanine + Oxoglutaric acid + L-Alanine <> L-Glutamic acid + Pyruvic acid + L-Glutamate
Oxoglutaric acid + NAD + Coenzyme A > NADH + Carbon dioxide + Succinyl-CoA + Succinyl-CoA
L-Aspartic acid + Oxoglutaric acid + L-Aspartic acid > Oxalacetic acid + L-Glutamic acid + L-Glutamate
a-Ketoisovaleric acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Valine + L-Valine
Isovaleric acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Valine + L-Valine
3-Methyl-2-oxovaleric acid + L-Glutamic acid + 3-Methyl-2-oxovaleric acid + L-Glutamate > Oxoglutaric acid + L-Valine + L-Valine
N-acetyl-L-glutamate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-Acetylornithine
N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + N-Acetylornithine
N2-Succinyl-L-ornithine + Oxoglutaric acid > L-Glutamic acid + N2-Succinyl-L-glutamic acid 5-semialdehyde + L-Glutamate
Putrescine + Oxoglutaric acid > L-Glutamic acid + 4-Aminobutyraldehyde + L-Glutamate
gamma-Aminobutyric acid + Oxoglutaric acid > Succinic acid semialdehyde + L-Glutamic acid + L-Glutamate
Phosphohydroxypyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + DL-O-Phosphoserine
4-hydroxyphenylpyruvate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Tyrosine + L-Tyrosine
Ketoleucine + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Leucine
Phenylpyruvic acid + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-Phenylalanine + L-Phenylalanine
L-Glutamic acid + L-Glutamate <> Oxoglutaric acid + O-Phospho-4-hydroxy-L-threonine
2-Oxo-3-hydroxy-4-phosphobutanoic acid + L-Glutamic acid + L-Glutamate <> O-Phospho-4-hydroxy-L-threonine + Oxoglutaric acid
Imidazole acetol-phosphate + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + L-histidinol-phosphate
3-Methyl-2-oxovaleric acid + L-Glutamic acid + 3-Methyl-2-oxovaleric acid + L-Glutamate > Oxoglutaric acid + L-Isoleucine + L-Isoleucine
UDP-β-L-threo-pentapyranos-4-ulose + L-Glutamic acid + L-Glutamate > Oxoglutaric acid + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose
L-Phenylalanine + Oxygen + L-Phenylalanine <> Oxoglutaric acid + Phenylpyruvic acid
L-Glutamic acid + dTDP-4-dehydro-6-deoxy-D-glucose + L-Glutamate > Oxoglutaric acid + dTDP-thomosamine
isochorismate + Oxoglutaric acid + Hydrogen ion + Isochorismate > Carbon dioxide + 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate
Putrescine + Oxoglutaric acid <> L-Glutamic acid + 1-Pyrroline + Water + L-Glutamate
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS)splash10-000b-3910000000-4097b7eb52c2910a4277View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)splash10-0002-1910000000-3277227b9c4da4baa1f7View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (2 TMS; 1 MEOX)splash10-00di-9300000000-974bce546caa4fbe6b0fView in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-000i-9710000000-d0aea11e947b042571f9View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 2 TMS)splash10-052s-4920000000-bf7ed92c68fd4c8dbb6bView in MoNA
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0zfr-6900000000-7fc343a243ce5d2a4f39View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0a4i-9200000000-1a7af9946604baa8b3d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0a4l-9800000000-30495b2afdd3526854e7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0002-0925200000-af33449c9638276466c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-6e43f767847790112b65View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-03di-0900000000-4cacc41705b7b385e91eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-1367eeeb6ad64c67a0aaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-000t-0915051100-91cda631ee54800322b8View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0a4i-9000000000-4f842c3673925d29c402View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-0udi-0900000000-5e751351656f6eb62de3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT (LTQ Orbitrap XL, Thermo Scientfic) , Negativesplash10-001i-0910000000-7729faa24733fbad77b7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0002-0900000000-c3c62f83bff99f44f7abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0zfr-6900000000-b6d8379db3e3f1480b14View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0a4i-9300000000-4fde39bb93cde5a27f23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-00i0-9000000000-4343832f3a55842423a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-2900000000-5aa3d6d620db1d733a65View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0m30-7900000000-fc77f69ad43f915bf23eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-9000000000-c597f1f5e416037aa82dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0f9t-8900000000-b2d3fa8d7ab01a220d9aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-053r-9100000000-554bfbd6839bc376cba0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-1900000000-f2b463076a150a514f0cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0fba-9200000000-4e367c66e94c51eb1a1bView in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Bales JR, Higham DP, Howe I, Nicholson JK, Sadler PJ: Use of high-resolution proton nuclear magnetic resonance spectroscopy for rapid multi-component analysis of urine. Clin Chem. 1984 Mar;30(3):426-32. Pubmed: 6321058
  • Barbas C, Garcia A, de Miguel L, Simo C: Evaluation of filter paper collection of urine samples for detection and measurement of organic acidurias by capillary electrophoresis. J Chromatogr B Analyt Technol Biomed Life Sci. 2002 Nov 15;780(1):73-82. Pubmed: 12383482
  • Bennett, B. D., Kimball, E. H., Gao, M., Osterhout, R., Van Dien, S. J., Rabinowitz, J. D. (2009). "Absolute metabolite concentrations and implied enzyme active site occupancy in Escherichia coli." Nat Chem Biol 5:593-599. Pubmed: 19561621
  • Garcia A, Barbas C, Aguilar R, Castro M: Capillary electrophoresis for rapid profiling of organic acidurias. Clin Chem. 1998 Sep;44(9):1905-11. Pubmed: 9732975
  • Guneral F, Bachmann C: Age-related reference values for urinary organic acids in a healthy Turkish pediatric population. Clin Chem. 1994 Jun;40(6):862-6. Pubmed: 8087979
  • 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
  • Kelley RI: Octenylsuccinic aciduria in children fed protein-hydrolysate formulas containing modified cornstarch. Pediatr Res. 1991 Dec;30(6):564-9. Pubmed: 1805153
  • 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
  • Kitaura J, Miki Y, Kato H, Sakakihara Y, Yanagisawa M: Hyperinsulinaemic hypoglycaemia associated with persistent hyperammonaemia. Eur J Pediatr. 1999 May;158(5):410-3. Pubmed: 10333126
  • Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. Pubmed: 9869358
  • Nicholson JK, Foxall PJ, Spraul M, Farrant RD, Lindon JC: 750 MHz 1H and 1H-13C NMR spectroscopy of human blood plasma. Anal Chem. 1995 Mar 1;67(5):793-811. Pubmed: 7762816
  • Ohdoi C, Nyhan WL, Kuhara T: Chemical diagnosis of Lesch-Nyhan syndrome using gas chromatography-mass spectrometry detection. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jul 15;792(1):123-30. Pubmed: 12829005
  • Rocchiccioli F, Leroux JP, Cartier PH: Microdetermination of 2-ketoglutaric acid in plasma and cerebrospinal fluid by capillary gas chromatography mass spectrometry; application to pediatrics. Biomed Mass Spectrom. 1984 Jan;11(1):24-8. Pubmed: 6704500
  • Stromme JH, Borud O, Moe PJ: Fatal lactic acidosis in a newborn attributable to a congenital defect of pyruvate dehydrogenase. Pediatr Res. 1976 Jan;10(1):62-6. Pubmed: 813176
  • Sweatman BC, Farrant RD, Holmes E, Ghauri FY, Nicholson JK, Lindon JC: 600 MHz 1H-NMR spectroscopy of human cerebrospinal fluid: effects of sample manipulation and assignment of resonances. J Pharm Biomed Anal. 1993 Aug;11(8):651-64. Pubmed: 8257730
  • 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
  • Zupke C, Sinskey AJ, Stephanopoulos G: Intracellular flux analysis applied to the effect of dissolved oxygen on hybridomas. Appl Microbiol Biotechnol. 1995 Dec;44(1-2):27-36. Pubmed: 8579834
Synthesis Reference: Tanaka, Katsunobu; kimura, Kazu; Yamaguchi, Ken. Fermentative production of a-oxoglutaric acid. U.S. (1973), 4 pp.
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID16810
HMDB IDHMDB00208
Pubchem Compound ID51
Kegg IDC00026
ChemSpider ID50
WikipediaOxoglutarate
BioCyc ID2-KETOGLUTARATE
EcoCyc ID2-KETOGLUTARATE
Ligand ExpoAKG

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
L-glutamate + H(2)O + NADP(+) = 2-oxoglutarate + NH(3) + NADPH
Gene Name:
gdhA
Locus Tag:
PA4588
Molecular weight:
48.9 kDa
Reactions
L-glutamate + H(2)O + NADP(+) = 2-oxoglutarate + NH(3) + NADPH.
General function:
Involved in transferase activity
Specific function:
An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate
Gene Name:
tyrB
Locus Tag:
PA3139
Molecular weight:
43.3 kDa
Reactions
An aromatic amino acid + 2-oxoglutarate = an aromatic oxo acid + L-glutamate.
General function:
Involved in magnesium ion binding
Specific function:
Isocitrate + NADP(+) = 2-oxoglutarate + CO(2) + NADPH
Gene Name:
icd
Locus Tag:
PA2623
Molecular weight:
45.6 kDa
Reactions
Isocitrate + NADP(+) = 2-oxoglutarate + CO(2) + NADPH.
General function:
Involved in catalytic activity
Specific function:
2 L-glutamate + NADP(+) = L-glutamine + 2- oxoglutarate + NADPH
Gene Name:
gltB
Locus Tag:
PA5036
Molecular weight:
161.6 kDa
Reactions
2 L-glutamate + NADP(+) = L-glutamine + 2-oxoglutarate + NADPH.
General function:
Involved in iron-sulfur cluster binding
Specific function:
2 L-glutamate + NADP(+) = L-glutamine + 2- oxoglutarate + NADPH
Gene Name:
gltD
Locus Tag:
PA5035
Molecular weight:
52.6 kDa
Reactions
2 L-glutamate + NADP(+) = L-glutamine + 2-oxoglutarate + NADPH.
General function:
Involved in glutamate-ammonia ligase activity
Specific function:
ATP + L-glutamate + NH(3) = ADP + phosphate + L-glutamine
Gene Name:
glnA
Locus Tag:
PA5119
Molecular weight:
51.9 kDa
Reactions
ATP + L-glutamate + NH(3) = ADP + phosphate + L-glutamine.
General function:
Involved in amino acid binding
Specific function:
3-phospho-D-glycerate + NAD(+) = 3- phosphonooxypyruvate + NADH
Gene Name:
serA
Locus Tag:
PA0316
Molecular weight:
44.2 kDa
Reactions
3-phospho-D-glycerate + NAD(+) = 3-phosphonooxypyruvate + NADH.
2-hydroxyglutarate + NAD(+) = 2-oxoglutarate + NADH.
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:
sucA
Locus Tag:
PA1585
Molecular weight:
105.9 kDa
Reactions
2-oxoglutarate + [dihydrolipoyllysine-residue succinyltransferase] lipoyllysine = [dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine + CO(2).
General function:
Involved in transferase activity, transferring acyl groups
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:
sucB
Locus Tag:
PA1586
Molecular weight:
42.9 kDa
Reactions
Succinyl-CoA + enzyme N(6)-(dihydrolipoyl)lysine = CoA + enzyme N(6)-(S-succinyldihydrolipoyl)lysine.
General function:
Involved in transaminase activity
Specific function:
Involved in both the arginine and lysine biosynthetic pathways
Gene Name:
argD
Locus Tag:
PA0895
Molecular weight:
43.7 kDa
Reactions
N(2)-acetyl-L-ornithine + 2-oxoglutarate = N-acetyl-L-glutamate 5-semialdehyde + L-glutamate.
N-succinyl-L-2,6-diaminoheptanedioate + 2-oxoglutarate = N-succinyl-2-L-amino-6-oxoheptanedioate + L-glutamate.
General function:
Involved in 4-aminobutyrate transaminase activity
Specific function:
4-aminobutanoate + 2-oxoglutarate = succinate semialdehyde + L-glutamate
Gene Name:
gabT
Locus Tag:
PA0266
Molecular weight:
45.2 kDa
Reactions
4-aminobutanoate + 2-oxoglutarate = succinate semialdehyde + L-glutamate.
(S)-3-amino-2-methylpropanoate + 2-oxoglutarate = 2-methyl-3-oxopropanoate + 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. Is involved in both pyridoxine and serine biosynthesis
Gene Name:
serC
Locus Tag:
PA3167
Molecular weight:
39.9 kDa
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 zinc ion binding
Specific function:
Displays a broad specificity and can also deacylate substrates such as acetylarginine, acetylhistidine or acetylglutamate semialdehyde
Gene Name:
argE
Locus Tag:
PA5206
Molecular weight:
42.2 kDa
Reactions
N(2)-acetyl-L-ornithine + H(2)O = acetate + L-ornithine.
General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the conversion of taurine and alpha ketoglutarate to sulfite, aminoacetaldehyde and succinate. Required for the utilization of taurine (2-aminoethanesulfonic acid) as an alternative sulfur source. Pentane-sulfonic acid, 3- (N-morpholino)propanesulfonic acid and 1,3-dioxo-2- isoindolineethanesulfonic acid are also substrates for this enzyme
Gene Name:
tauD
Locus Tag:
PA3935
Molecular weight:
31 kDa
Reactions
Taurine + 2-oxoglutarate + O(2) = sulfite + aminoacetaldehyde + succinate + CO(2).
General function:
Involved in transaminase activity
Specific function:
Catalyzes the conversion of UDP-4-keto-arabinose (UDP- Ara4O) to UDP-4-amino-4-deoxy-L-arabinose (UDP-L-Ara4N). The modified arabinose is attached to lipid A and is required for resistance to polymyxin and cationic antimicrobial peptides
Gene Name:
arnB
Locus Tag:
PA3552
Molecular weight:
41.9 kDa
Reactions
UDP-4-amino-4-deoxy-beta-L-arabinose + 2-oxoglutarate = UDP-beta-L-threo-pentapyranos-4-ulose + glutamate.
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Specific function unknown
Gene Name:
yfbQ
Locus Tag:
PA2828
Molecular weight:
44.8 kDa
Reactions
L-alanine + 2-oxoglutarate = pyruvate + L-glutamate.
General function:
Involved in catalytic activity
Specific function:
Acts on leucine, isoleucine and valine
Gene Name:
ilvE
Locus Tag:
PA5013
Molecular weight:
34.1 kDa
Reactions
L-leucine + 2-oxoglutarate = 4-methyl-2-oxopentanoate + L-glutamate.
L-isoleucine + 2-oxoglutarate = (S)-3-methyl-2-oxopentanoate + L-glutamate.
L-valine + 2-oxoglutarate = 3-methyl-2-oxobutanoate + L-glutamate.
General function:
Amino acid transport and metabolism
Specific function:
Specific function unknown
Gene Name:
yfdZ
Locus Tag:
PA4715
Molecular weight:
46.1 kDa
Reactions
L-alanine + 2-oxoglutarate = pyruvate + L-glutamate.

Transporters

General function:
Involved in transporter activity
Specific function:
Uptake of alpha-ketoglutarate across the boundary membrane with the concomitant import of a cation (symport system)
Gene Name:
kgtP
Locus Tag:
PA0229
Molecular weight:
47.2 kDa