alpha-Ketoglutarate (PAMDB000466)
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Version | 1.0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Update Date | 1/22/2018 12:54:54 PM | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Metabolite ID | PAMDB000466 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Synonyms: |
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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 Description | This 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 Class | Organic acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Class | Keto acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Sub Class | Gamma-keto acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Direct Parent | Gamma-keto acids and derivatives | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Alternative Parents | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Substituents |
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Molecular Framework | Aliphatic acyclic compounds | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
External Descriptors |
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Physical Properties | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
State: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Charge: | -2 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Melting point: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Experimental Properties: |
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Predicted Properties |
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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 More...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 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Pathways: |
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Spectra | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Spectra: |
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References | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
References: |
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Synthesis Reference: | Not Available | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
Material Safety Data Sheet (MSDS) | Download (PDF) | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
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External Links: |
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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 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 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