alpha-Ketoglutarate (PAMDB000466)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000466
Identification
Name: alpha-Ketoglutarate
Description:Alpha-ketoglutarate 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. Alpha-ketoglutarate is invovled in pentose and glucuronate interconversions, C5-Branched dibasic acid metabolism, Vitamin B6 metabolism, alanine, aspartate and glutamate metabolism, Butanoate metabolism, Glyoxylate and dicarboxylate metabolism, Carbon fixation pathways in prokaryotes, Lysine biosynthesis, Biosynthesis of terpenoids and steroids, and the Citrate cycle (TCA cycle). Alpha-Ketoglutaric acid is one of two ketone derivatives of glutaric acid. (The term ketoglutaric acid, when not further qualified, almost always refers to the alpha variant. Alpha-Ketoglutaric acid varies only by the position of the ketone functional group, and is much less common. Its anion, alpha-ketoglutarate (alpha-KG, also called oxo-glutarate) is an important biological compound. It is the keto acid produced by de-amination of glutamate, and is an intermediate in the Krebs cycle. (WikiPedia)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 2-Ketoglutarate
  • 2-Ketoglutaric acid
  • 2-OG
  • 2-Oxo-1,5-pentanedioate
  • 2-Oxo-1,5-pentanedioic acid
  • 2-Oxoglutarate
  • 2-Oxoglutarate(2-)
  • 2-Oxoglutaric acid
  • 2-Oxoglutaric acid(2-)
  • 2-Oxopentanedioate
  • 2-Oxopentanedioate, ion(2-)
  • 2-Oxopentanedioic acid
  • 2-Oxopentanedioic acid, ion(2-)
  • a-Ketoglutarate
  • a-Ketoglutaric acid
  • Alpha-Ketoglutarate
  • Alpha-Ketoglutaric acid
  • Oxoglutarate
  • Oxoglutaric acid
  • Pentanedioate, 2-oxo-, ion(2-)
  • Pentanedioic acid, 2-oxo-, ion(2-)
  • α-Ketoglutarate
  • α-Ketoglutaric acid
Chemical Formula: C5H4O5
Average Molecular Weight: 144.0823
Monoisotopic Molecular Weight: 144.005873238
InChI Key: KPGXRSRHYNQIFN-UHFFFAOYSA-L
InChI:InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/p-2
CAS number: Not Available
IUPAC Name:2-oxopentanedioate
Traditional IUPAC Name: α ketoglutarate
SMILES:[O-]C(=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
  • Fatty acid
  • Dicarboxylic acid or derivatives
  • Alpha-keto acid
  • Ketone
  • Carboxylic acid salt
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Organic anion
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
Physical Properties
State: Not Available
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility56.5 mg/mLALOGPS
logP-0.45ALOGPS
logP-0.11ChemAxon
logS-0.5ALOGPS
pKa (Strongest Acidic)2.66ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area97.33 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity50.56 m3·mol-1ChemAxon
Polarizability11.32 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
alpha-Ketoglutarate + Coenzyme A + NAD > Carbon dioxide + NADH + Succinyl-CoA
N-Acetylornithine + alpha-Ketoglutarate <> N-Acetyl-L-glutamate 5-semialdehyde + L-Glutamate
alpha-Ketoglutarate + L-Alanine <> L-Glutamate + Pyruvic acid
gamma-Aminobutyric acid + alpha-Ketoglutarate <> L-Glutamate + Succinic acid semialdehyde
Ketoleucine + L-Glutamate > alpha-Ketoglutarate + L-Leucine
alpha-Ketoglutarate + L-Phenylalanine <> L-Glutamate + Phenylpyruvic acid
alpha-Ketoglutarate + L-Tyrosine <> 4-Hydroxyphenylpyruvic acid + L-Glutamate
alpha-Ketoglutarate + Oxygen + Taurine <> Aminoacetaldehyde + Carbon dioxide + Hydrogen ion + Sulfite + Succinic acid
L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid <> alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine
Phosphohydroxypyruvic acid + L-Glutamate > alpha-Ketoglutarate + Phosphoserine
alpha-Ketoglutarate + L-Aspartic acid <> L-Glutamate + Oxalacetic acid
Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH
alpha-Ketoglutarate + N2-Succinyl-L-ornithine <> L-Glutamate + N2-Succinyl-L-glutamic acid 5-semialdehyde
L-Glutamate + Water + NADP <> alpha-Ketoglutarate + Hydrogen ion + NADPH + Ammonium
L-Glutamate + Imidazole acetol-phosphate <> alpha-Ketoglutarate + Histidinol phosphate
L-Glutamate + UDP-4-Keto-pyranose <> alpha-Ketoglutarate + Uridine 5''-diphospho-{beta}-4-deoxy-4-amino-L-arabinose
alpha-Ketoglutarate + Hydrogen ion + Isochorismate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide
alpha-Ketoglutarate + Putrescine > 4-Aminobutyraldehyde + L-Glutamate
alpha-Ketoglutarate + N-Succinyl-L,L-2,6-diaminopimelate <> L-Glutamate + N-Succinyl-2-amino-6-ketopimelate
alpha-Ketoglutarate + L-Isoleucine <> 3-Methyl-2-oxovaleric acid + L-Glutamate
alpha-Ketoglutarate + L-Valine <> alpha-Ketoisovaleric acid + L-Glutamate
4,6-Dideoxy-4-oxo-dTDP-D-glucose + L-Glutamate > alpha-Ketoglutarate + dTDP-D-Fucosamine
2 L-Glutamate + NAD <> L-Glutamine + alpha-Ketoglutarate + NADH + Hydrogen ion
2 L-Glutamate + NADP <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ion
L-Glutamate + NAD + Water <> alpha-Ketoglutarate + Ammonia + NADH + Hydrogen ion
L-Glutamate + NADP + Water <> alpha-Ketoglutarate + Ammonia + NADPH + Hydrogen ion
Isocitric acid + NADP <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion
Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide
beta-Alanine + alpha-Ketoglutarate <> Malonic semialdehyde + L-Glutamate
L-Leucine + alpha-Ketoglutarate <> 4-Methyl-2-oxopentanoate + L-Glutamate + Ketoleucine
Cysteic acid + alpha-Ketoglutarate <> 3-Sulfopyruvic acid + L-Glutamate
3-Sulfinoalanine + alpha-Ketoglutarate <> 3-Sulfinylpyruvic acid + L-Glutamate
(S)-b-aminoisobutyric acid + alpha-Ketoglutarate <> (S)-Methylmalonic acid semialdehyde + L-Glutamate
L-erythro-4-Hydroxyglutamate + alpha-Ketoglutarate <> D-4-Hydroxy-2-oxoglutarate + L-Glutamate
Taurine + alpha-Ketoglutarate + Oxygen <> Sulfite + Aminoacetaldehyde + Succinic acid + Carbon dioxide
2-Oxo-4-methylthiobutanoic acid + L-Glutamate <> L-Methionine + alpha-Ketoglutarate
Isochorismate + alpha-Ketoglutarate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide
alpha-Ketoglutarate <> [Dihydrolipoyllysine-residue succinyltransferase] S-succinyldihydrolipoyllysine + Carbon dioxide
Phosphoserine + alpha-Ketoglutarate + O-Phospho-4-hydroxy-L-threonine <> Phosphohydroxypyruvic acid + L-Glutamate + 2-Oxo-3-hydroxy-4-phosphobutanoic acid
Ethylenediamine + alpha-Ketoglutarate + 4-Aminobutyraldehyde <> 1-Pyrroline + L-Glutamate + Water
2 L-Glutamate + NADP + Ammonia + Water <> L-Glutamine + alpha-Ketoglutarate + NADPH + Hydrogen ion
Aromatic amino acid + alpha-Ketoglutarate <> Aromatic oxo acid + L-Glutamate
3-Phospho-D-glycerate + NAD + D-2-Hydroxyglutaric acid <> Phosphohydroxypyruvic acid + NADH + Hydrogen ion + alpha-Ketoglutarate
Isocitric acid + NADP + Oxalosuccinic acid <> alpha-Ketoglutarate + Carbon dioxide + NADPH + Hydrogen ion
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-0900000000-da0cb6c20458b87b3653View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-3900000000-422a5a72c9bb005a61caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0570-9200000000-a8a32be3a2643778852fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-c9bc4bf076ca25e8f08eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-5900000000-c6e0189e12012dfa6430View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9100000000-fcfd4e27706409ebc8e5View in MoNA
References
References:
  • 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
  • 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) Download (PDF)
External Links:
ResourceLink
CHEBI ID16810
HMDB IDHMDB00208
Pubchem Compound ID164533
Kegg IDC00026
ChemSpider ID144236
WikipediaOxoglutarate
BioCyc IDNot Available

Enzymes

Protein Details
• NADP-specific glutamate dehydrogenase
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.
Protein Details
• Aromatic-amino-acid aminotransferase
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.
Protein Details
• Isocitrate dehydrogenase [NADP]
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.
Protein Details
• Glutamate synthase [NADPH] large chain
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.
Protein Details
• Glutamate synthase [NADPH] small chain
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.
Protein Details
• 2-oxoglutarate dehydrogenase E1 component
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).
Protein Details
• Dihydrolipoyllysine-residue succinyltransferase component of 2-oxoglutarate dehydrogenase complex
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.
Protein Details
• Acetylornithine/succinyldiaminopimelate aminotransferase
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.
Protein Details
• 4-aminobutyrate aminotransferase
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.
Protein Details
• Phosphoserine aminotransferase
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.
Protein Details
• Alpha-ketoglutarate-dependent taurine dioxygenase
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).
Protein Details
• UDP-4-amino-4-deoxy-L-arabinose--oxoglutarate aminotransferase
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.
Protein Details
• Uncharacterized aminotransferase yfbQ
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.
Protein Details
• Branched-chain-amino-acid aminotransferase
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.
Protein Details
• Uncharacterized aminotransferase yfdZ
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

Protein Details
• Alpha-ketoglutarate permease
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