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Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
Metabolic Modeling Tutorial
discounted EARLY registration ends Dec 31, 2014
BioCyc websites down
12/28 - 12/31
for maintenance.
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MetaCyc Compound: 2-oxoglutarate

Synonyms: 2-oxoglutarate, ketoglutarate, α-ketoglutarate, 2-oxoglutaric acid, α-ketoglutaric acid, α-oxoglutarate, 2-ketoglutaric acid, 2-ketoglutarate, 2-oxopentanedionic acid, 2-oxopentanedionate, a-ketoglutaric acid

Superclasses: an acid all carboxy acids a carboxylate a 2-oxo acid a 2-oxo carboxylate
an acid all carboxy acids a carboxylate a 2-oxo carboxylate

Chemical Formula: C5H4O5

Molecular Weight: 144.08 Daltons

Monoisotopic Molecular Weight: 146.0215233031 Daltons

SMILES: C(CC([O-])=O)C(=O)C([O-])=O

InChI: InChI=1S/C5H6O5/c6-3(5(9)10)1-2-4(7)8/h1-2H2,(H,7,8)(H,9,10)/p-2

InChIKey: InChIKey=KPGXRSRHYNQIFN-UHFFFAOYSA-L

Unification Links: CAS:328-50-7 , ChEBI:16810 , ChemSpider:144236 , HMDB:HMDB00208 , IAF1260:33565 , KEGG:C00026 , KNApSAcK:C00000769 , MetaboLights:MTBLC16810 , PubChem:164533

Standard Gibbs Free Energy of Change Formation (ΔfG in kcal/mol): -149.76376 Inferred by computational analysis [Latendresse13]

Reactions known to consume the compound:

(5R)-carbapenem carboxylate biosynthesis :
(3S,5S)-carbapenam-3-carboxylate + 2-oxoglutarate + oxygen → (5R)-carbapen-2-em-3-carboxylate + succinate + CO2 + H2O

1,4-dihydroxy-2-naphthoate biosynthesis I , 1,4-dihydroxy-2-naphthoate biosynthesis II (plants) :
isochorismate + 2-oxoglutarate + H+ → 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + CO2

2,4-dichlorophenoxyacetate degradation :
2,4-dichlorophenoxyacetate + 2-oxoglutarate + oxygen → 2,4-dichlorophenol + glyoxylate + succinate + CO2

2-aminoethylphosphonate degradation III :
(2-aminoethyl)phosphonate + 2-oxoglutarate + oxygen → (2-amino-1-hydroxyethyl)phosphonate + succinate + CO2

2-oxoglutarate decarboxylation to succinyl-CoA :
2-oxoglutarate + a [2-oxoglutarate dehydrogenase E2 protein] N6-lipoyl-L-lysine + H+ → a [2-oxoglutarate dehydrogenase E2 protein] N6-S-succinyldihydrolipoyl-L-lysine + CO2

4-chloro-2-methylphenoxyacetate degradation :
4-chloro-2-methylphenoxyacetate + 2-oxoglutarate + oxygen → 2-methyl-4-chlorophenol + glyoxylate + succinate + CO2

achromobactin biosynthesis :
diaminobutyryl-citryl-ethanolamino-α-ketoglutarate + ATP + 2-oxoglutarate → achromobactin + AMP + diphosphate + H+
α-ketoglutaryl-diaminobutyryl-citryl-ethanolamine + ATP + 2-oxoglutarate → achromobactin + AMP + diphosphate + H+
diaminobutyryl-citryl-ethanolamine + ATP + 2-oxoglutarate → diaminobutyryl-citryl-ethanolamino-α-ketoglutarate + AMP + diphosphate + H+
diaminobutyryl-citryl-ethanolamine + ATP + 2-oxoglutarate → α-ketoglutaryl-diaminobutyryl-citryl-ethanolamine + AMP + diphosphate + H+

ammonia assimilation cycle I , glutamate biosynthesis IV :
2 L-glutamate + NAD+ ← L-glutamine + 2-oxoglutarate + NADH + H+

ammonia assimilation cycle II , glutamate biosynthesis V , glutamine biosynthesis III :
2 L-glutamate + 2 an oxidized ferredoxin ← 2-oxoglutarate + L-glutamine + 2 a reduced ferredoxin + 2 H+

anthocyanin biosynthesis (cyanidin 3-O-glucoside) :
leucocyanidin + 2-oxoglutarate + oxygen → cyanidin + succinate + CO2 + H+ + 2 H2O
leucocyanidin + 2-oxoglutarate + oxygen → a dihydroquercetin + succinate + CO2 + H2O

anthocyanin biosynthesis (delphinidin 3-O-glucoside) :
leucodelphinidin + 2-oxoglutarate + oxygen → delphinidin + CO2 + succinate + H+ + 2 H2O

anthocyanin biosynthesis (pelargonidin 3-O-glucoside) :
leucopelargonidin + 2-oxoglutarate + oxygen → pelargonidin + succinate + CO2 + H+ + 2 H2O

apigeninidin 5-O-glucoside biosynthesis :
apiforol + 2-oxoglutarate + oxygen → apigeninidin + succinate + CO2 + 2 H2O

brassicicene C biosynthesis :
fusicocca-2,10(14)-diene-8β,16-diol + 2-oxoglutarate + oxygen → fusicocca-1,10(14)-diene-3,8β,16-triol + succinate + CO2

chrysin biosynthesis :
(2S)-pinocembrin + 2-oxoglutarate + oxygen → chrysin + succinate + CO2 + H2O

clavulanate biosynthesis :
proclavaminate + 2-oxoglutarate + oxygen → dihydroclavaminate + CO2 + succinate + H2O
dihydroclavaminate + 2-oxoglutarate + oxygen → clavaminate + CO2 + succinate + H2O
deoxyamidinoproclavaminate + 2-oxoglutarate + oxygen → amidinoproclavaminate + succinate + CO2

coumarins biosynthesis (engineered) :
4-coumaryl-CoA + 2-oxoglutarate + oxygen → 2,4-dihydroxycinnamoyl-CoA + succinate + CO2
feruloyl-CoA + 2-oxoglutarate + oxygen → 6'-hydroxyferuloyl-CoA + succinate + CO2

D-cycloserine biosynthesis :
L-arginine + 2-oxoglutarate + oxygen → Nω-hydroxy-L-arginine + succinate + CO2

deacetylcephalosporin C biosynthesis :
deacetoxycephalosporin C + 2-oxoglutarate + oxygen → deacetylcephalosporin-C + succinate + CO2
2-oxoglutarate + penicillin N + oxygen → CO2 + succinate + deacetoxycephalosporin C + H2O

dehydrophos biosynthesis :
2-hydroxyethylphosphonate + 2-oxoglutarate + oxygen → 1,2-dihydroxyethylphosphonate + succinate + CO2

DIMBOA-glucoside biosynthesis :
DIBOA-β-D-glucoside + 2-oxoglutarate + oxygen → TRIBOA-β-D-glucoside + succinate + CO2

ethylene biosynthesis II (microbes) :
L-arginine + 2-oxoglutarate + oxygen → (3S)-3-hydroxy-L-arginine + succinate + CO2
2-oxoglutarate + oxygen + 2 H+ → ethylene + 3 CO2 + H2O

ethylene biosynthesis IV :
2-oxoglutarate + L-arginine + oxygen → succinate + CO2 + guanidinium + (S)-1-pyrroline-5-carboxylate + H2O + H+
2-oxoglutarate + oxygen + 2 H+ → ethylene + 3 CO2 + H2O

ethylene biosynthesis V (engineered) :
2-oxoglutarate + oxygen + 2 H+ → ethylene + 3 CO2 + H2O

fatty acid α-oxidation II :
a 3-methyl-branched 2,3,4-saturated fatty acyl-CoA + 2-oxoglutarate + oxygen → a 2-hydroxy-3-methyl-branched 2,3,4-saturated fatty acyl-CoA + succinate + CO2

flavonoid biosynthesis :
(2R)-naringenin + 2-oxoglutarate + oxygen → (-)-dihydrokaempferol + succinate + CO2
(2S)-naringenin + 2-oxoglutarate + oxygen → (+)-dihydrokaempferol + succinate + CO2

flavonoid biosynthesis (in equisetum) :
(2S)-naringenin + 2-oxoglutarate + oxygen → apigenin + succinate + CO2 + H2O + H+
eriodictyol + 2-oxoglutarate + oxygen → luteolin + succinate + CO2 + H2O
(2S)-naringenin + 2-oxoglutarate + oxygen → (+)-dihydrokaempferol + succinate + CO2
(+)-taxifolin + 2-oxoglutarate + oxygen → quercetin + succinate + CO2 + H2O
(+)-dihydrokaempferol + 2-oxoglutarate + oxygen → kaempferol + succinate + CO2 + H2O + H+
eriodictyol + 2-oxoglutarate + oxygen → (+)-taxifolin + succinate + CO2

flavonol biosynthesis :
dihydromyricetin + 2-oxoglutarate + oxygen → myricetin + succinate + CO2 + H2O
(+)-taxifolin + 2-oxoglutarate + oxygen → quercetin + succinate + CO2 + H2O
(+)-dihydrokaempferol + 2-oxoglutarate + oxygen → kaempferol + succinate + CO2 + H2O + H+

FR-900098 and FR-33289 antibiotics biosynthesis :
FR-900098 + 2-oxoglutarate + oxygen → FR-33289 + succinate + CO2

fumitremorgin A biosynthesis :
fumitremorgin B + 2-oxoglutarate + a reduced electron acceptor + 2 oxygen → verruculogen + succinate + CO2 + an oxidized electron acceptor + H2O

fusicoccin A biosynthesis :
fusicocca-2,10(14)-diene-8β,16-diol + 2-oxoglutarate + oxygen → 8β-hydroxyfusicocca-1,10(14)-diene-16-al + succinate + CO2 + H2O

γ-butyrobetaine degradation :
γ-butyrobetaine + 2-oxoglutarate + oxygen → L-carnitine + succinate + CO2

gibberellin biosynthesis I (non C-3, non C-13 hydroxylation) :
gibberellin A24 + 2-oxoglutarate + oxygen → gibberellin A9 + 2 CO2 + succinate + H+
gibberellin A12 + 2-oxoglutarate + oxygen → gibberellin A15 (open lactone form) + CO2 + succinate
gibberellin A24 + 2-oxoglutarate + oxygen → gibberellin A25 + CO2 + succinate + H+
gibberellin A15 (open lactone form) + 2-oxoglutarate + oxygen → gibberellin A24 + succinate + CO2 + H2O
gibberellin A25 + 2-oxoglutarate + oxygen → gibberellin A13 + succinate + CO2
gibberellin A9 + 2-oxoglutarate + oxygen → gibberellin A4 + succinate + CO2
gibberellin A24 + 2-oxoglutarate + oxygen → gibberellin A36 + succinate + CO2

gibberellin biosynthesis II (early C-3 hydroxylation) :
gibberellin A36 + 2-oxoglutarate + oxygen → gibberellin A4 + succinate + 2 CO2 + H+
gibberellin A14 + 2-oxoglutarate + oxygen → gibberellin A37 + CO2 + succinate
gibberellin A37 + 2-oxoglutarate + oxygen → gibberellin A36 + succinate + CO2 + H2O
gibberellin A12 + 2-oxoglutarate + oxygen → gibberellin A14 + succinate + CO2
gibberellin A15 (open lactone form) + 2-oxoglutarate + oxygen → gibberellin A37 + succinate + CO2

gibberellin biosynthesis III (early C-13 hydroxylation) :
gibberellin44 (open lactone form) + 2-oxoglutarate + oxygen → gibberellin A19 + succinate + CO2 + H2O
gibberellin44 (open lactone form) + 2-oxoglutarate + H+ + oxygen → gibberellin A38 + succinate + CO2 + H2O
gibberellin A19 + 2-oxoglutarate + oxygen → gibberellin A17 + succinate + CO2 + H+
gibberellin A19 + 2-oxoglutarate + oxygen → gibberellin A20 + 2 CO2 + succinate + H+
gibberellin A53 + 2-oxoglutarate + oxygen → gibberellin44 (open lactone form) + CO2 + succinate
gibberellin A20 + 2-oxoglutarate + oxygen → gibberellin A1 + succinate + CO2

gibberellin biosynthesis V :
gibberellin A5 + 2-oxoglutarate + oxygen → gibberellin A6 + succinate + CO2
gibberellin A5 + 2-oxoglutarate + oxygen → gibberellin A3 + succinate + CO2

gibberellin inactivation I (2β-hydroxylation) :
gibberellin A53 + 2-oxoglutarate + oxygen → gibberellin A97 + succinate + CO2
gibberellin A12 + 2-oxoglutarate + oxygen → gibberellin A110 + succinate + CO2
gibberellin A44 (closed lactone form) + 2-oxoglutarate + 2 H+ + oxygen → gibberellin A98 + succinate + CO2
gibberellin A34 + 2-oxoglutarate + oxygen → gibberellin A34-catabolite + succinate + CO2 + H+ + H2O
gibberellin A51 + 2-oxoglutarate + oxygen → gibberellin A51-catabolite + succinate + CO2 + H+ + H2O
gibberellin A9 + 2-oxoglutarate + oxygen → gibberellin A51 + succinate + CO2
gibberellin A8 + 2-oxoglutarate + oxygen → gibberellin A8-catabolite + succinate + CO2 + H+ + H2O
gibberellin A1 + 2-oxoglutarate + oxygen → gibberellin A8 + succinate + CO2
gibberellin A29 + 2-oxoglutarate + oxygen → gibberellin A29-catabolite + succinate + CO2 + H+ + H2O
gibberellin A20 + 2-oxoglutarate + oxygen → gibberellin A29 + succinate + CO2
gibberellin A4 + 2-oxoglutarate + oxygen → gibberellin A34 + succinate + CO2

glutamate biosynthesis I , glutamine degradation II :
2 L-glutamate + NADP+ ← L-glutamine + 2-oxoglutarate + NADPH + H+

hydroxylated mugineic acid phytosiderophore biosynthesis :
2'-deoxymugineate + 2-oxoglutarate + oxygen → 3-epihydroxy-2'-deoxymugineate + succinate + CO2 + H+
mugineate + 2-oxoglutarate + oxygen → 3-epihydroxymugineate + succinate + CO2
2'-deoxymugineate + 2-oxoglutarate + oxygen → mugineate + succinate + CO2 + H+

hyoscyamine and scopolamine biosynthesis :
(6S)-hydroxyhyoscyamine + 2-oxoglutarate + oxygen → scopolamine + succinate + CO2 + H+ + H2O
L-hyoscyamine + 2-oxoglutarate + oxygen → (6S)-hydroxyhyoscyamine + succinate + CO2

isoflavonoid biosynthesis II :
(2S)-naringenin + 2-oxoglutarate + oxygen → apigenin + succinate + CO2 + H2O + H+

isoleucine biosynthesis III :
(2S, 3S)-3-methylaspartate + 2-oxoglutarate → L-glutamate + methyloxaloacetate

kanamycin biosynthesis :
kanamycin B + 2-oxoglutarate + oxygen → 2'-dehydrokanamycin A + succinate + ammonium + CO2

L-carnitine biosynthesis :
γ-butyrobetaine + 2-oxoglutarate + oxygen → L-carnitine + succinate + CO2
N6,N6,N6-trimethyl-L-lysine + 2-oxoglutarate + oxygen → 3-hydroxy-N6,N6,N6-trimethyl-L-lysine + succinate + CO2

leucine degradation II :
(3R)-β-leucine + 2-oxoglutarate → L-glutamate + β-ketoisocaproate

leucodelphinidin biosynthesis :
(2S)-dihydrotricetin + 2-oxoglutarate + oxygen → dihydromyricetin + succinate + CO2

leucopelargonidin and leucocyanidin biosynthesis :
eriodictyol + 2-oxoglutarate + oxygen → (+)-taxifolin + succinate + CO2

luteolin biosynthesis :
(2S)-naringenin + 2-oxoglutarate + oxygen → apigenin + succinate + CO2 + H2O + H+
eriodictyol + 2-oxoglutarate + oxygen → luteolin + succinate + CO2 + H2O

luteolinidin 5-O-glucoside biosynthesis :
luteoforol + 2-oxoglutarate + oxygen + H+ → luteolinidin + succinate + CO2 + 2 H2O

lysine degradation II (mammalian) :
L-saccharopine + NADP+ + H2O ← L-lysine + 2-oxoglutarate + NADPH + H+

lysine degradation II (pipecolate pathway) :
L-lysine + 2-oxoglutarate → 2-keto-6-aminocaproate + L-glutamate

methanofuran biosynthesis :
trans-homoaconitate + coenzyme A + H+2-oxoglutarate + acetyl-CoA

Reactions known to produce the compound:

5-hydroxymethylfurfural degradation , furfural degradation :
2-oxoglutaryl-CoA + H2O → 2-oxoglutarate + coenzyme A + H+

bactoprenyl-diphospho-acetamido-4-amino-6-deoxygalactopyranose biosynthesis :
UDP-2-acetamido-2,6-dideoxy-α-D-xylo-hex4-ulose + L-glutamate → UDP-acetamido-4-amino-6-deoxygalactopyranose + 2-oxoglutarate

D-arabinose degradation III , D-galactarate degradation II , D-glucarate degradation II , trans-4-hydroxy-L-proline degradation II , xylose degradation III :
2,5-dioxopentanoate + NADP+ + H2O → 2-oxoglutarate + NADPH + 2 H+

GDP-L-colitose biosynthesis :
GDP-4-dehydro-α-D-rhamnose + L-glutamate → GDP-(2S,3S,6R)-3-hydroxy-5-amino-6-methyl-3,6-dihydro-2H-pyran + 2-oxoglutarate + H2O + H+

gentamicin biosynthesis :
gentamicin X2 + L-glutamate + oxygen → JI-20A + hydrogen peroxide + 2-oxoglutarate
G-418 + L-glutamate + oxygen → JI-20B + hydrogen peroxide + 2-oxoglutarate
gentamicin A2 + S-adenosyl-L-methionine + L-glutamate + oxygen → gentamicin A + S-adenosyl-L-homocysteine + hydrogen peroxide + 2-oxoglutarate + H+

glutamine biosynthesis III , TCA cycle II (plants and fungi) , TCA cycle III (animals) :
D-threo-isocitrate[mitochondrial lumen] + NAD+[mitochondrial lumen]2-oxoglutarate[mitochondrial lumen] + CO2[mitochondrial lumen] + NADH[mitochondrial lumen]

histidine biosynthesis :
imidazole acetol-phosphate + L-glutamate → L-histidinol-phosphate + 2-oxoglutarate

histidine degradation VI :
4-oxoglutaramate + H2O → 2-oxoglutarate + ammonium

hopanoid biosynthesis (bacteria) :
formyl hopane + L-glutamate → aminobacteriohopanetriol + 2-oxoglutarate

L-arabinose degradation III , L-lyxonate degradation :
2,5-dioxopentanoate + NAD(P)+ + H2O → 2-oxoglutarate + NAD(P)H + 2 H+

lysine biosynthesis II :
L-2-acetamido-6-oxoheptanedioate + L-glutamate → N-acetyl-L,L-2,6-diaminopimelate + 2-oxoglutarate

lysine biosynthesis IV :
L-saccharopine + NAD+ + H2O → 2-oxoglutarate + L-lysine + NADH + H+

mannojirimycin biosynthesis :
D-fructose 6-phosphate + L-glutamate → 2-amino-2-deoxy-mannitol-6-phosphate + 2-oxoglutarate

nicotine degradation I , S-methyl-5-thio-α-D-ribose 1-phosphate degradation :
2-oxoglutaramate + H2O → 2-oxoglutarate + ammonium

nopaline degradation :
D-nopaline + an oxidized electron acceptor + H2O → 2-oxoglutarate + L-arginine + a reduced electron acceptor

Not in pathways:
(S)-2-hydroxyglutarate + oxygen → 2-oxoglutarate + hydrogen peroxide
oxalosuccinate + H+2-oxoglutarate + CO2
D-glutamate + oxygen + H2O → ammonium + hydrogen peroxide + 2-oxoglutarate
L-glutamate + oxygen + H2O → ammonium + hydrogen peroxide + 2-oxoglutarate

methanofuran biosynthesis :
2-furaldehyde phosphate + a standard α amino acid → 2-methylamine-furan phosphate + a 2-oxo carboxylate

rhizocticin A and B biosynthesis :
2-keto-4-hydroxy-5-phosphonopentanoate + an L-amino acid → 2-amino-4-hydroxy-5-phosphonopentanoate + a 2-oxo carboxylate
2-keto-5-phosphono-3-cis-pentenoate + an L-amino acid → L-2-amino-5-phosphono-3-cis-pentenoate + a 2-oxo carboxylate


an (S)-2-hydroxyacid + oxygen → hydrogen peroxide + a 2-oxo carboxylate
a D-amino acid + oxygen + H2O → ammonium + hydrogen peroxide + a 2-oxo carboxylate
a standard α amino acid + oxygen + H2O → ammonium + hydrogen peroxide + a 2-oxo carboxylate
a D-amino acid[in] + an electron-transfer-related quinone[CCO-OUT-CCO-IN] + H2O[in]a 2-oxo carboxylate[in] + ammonium[in] + an electron-transfer-related quinol[CCO-OUT-CCO-IN]

prodigiosin biosynthesis :
(S)-3-acetyloctanal + an L-amino acid → 2-methyl-3-n-amyl-dihydropyrrole + a 2-oxo acid + H2O

3,3'-thiodipropionate degradation :
3-sulfinopropionate + an acyl-CoA → 3-sulfinopropanoyl-CoA + a carboxylate

dimethylsulfoniopropionate degradation II (cleavage) :
dimethylsulfoniopropanoate + an acyl-CoA → dimethylsulfoniopropioyl-CoA + a carboxylate

NAD/NADP-NADH/NADPH mitochondrial interconversion (yeast) :
an aldehyde + NADP+ + H2O → a carboxylate + NADPH + 2 H+
an aldehyde + NAD+ + H2O → a carboxylate + NADH + 2 H+

phosphatidylcholine resynthesis via glycerophosphocholine :
a phosphatidylcholine + 2 H2O → sn-glycero-3-phosphocholine + 2 a carboxylate + 2 H+


an acyl-CoA + H2O → a carboxylate + coenzyme A + H+
an L-1-phosphatidyl-inositol + H2O → 1-acyl-sn-glycero-3-phospho-D-myo-inositol + a carboxylate + H+
a carboxylic ester + H2O → an alcohol + a carboxylate + H+
an aldehyde + oxygen + H2O → a carboxylate + hydrogen peroxide + H+
a 1-lysophosphatidylcholine[periplasmic space] + H2O[periplasmic space]a carboxylate[periplasmic space] + sn-glycero-3-phosphocholine[periplasmic space] + H+[periplasmic space]
an aldehyde + FMNH2 + oxygen → hν + a carboxylate + FMN + H2O + 2 H+
an acylcholine + H2O → choline + a carboxylate + H+
a 1,2-diacyl-3-β-D-galactosyl-sn-glycerol + 2 H2O → 2 a carboxylate + 3-β-D-galactosyl-sn-glycerol + 2 H+
an acyl phosphate + H2O → a carboxylate + phosphate + H+
an S-acylglutathione + H2O → a carboxylate + glutathione
an N-acyl-L-aspartate + H2O → L-aspartate + a carboxylate

Reactions known to both consume and produce the compound:

(R)-cysteate degradation , coenzyme M biosynthesis II , sulfolactate degradation III :
L-cysteate + 2-oxoglutarate ↔ 3-sulfopyruvate + L-glutamate

(S)-reticuline biosynthesis I , 4-hydroxybenzoate biosynthesis I (eukaryotes) , 4-hydroxyphenylpyruvate biosynthesis , atromentin biosynthesis , rosmarinic acid biosynthesis I , tyrosine biosynthesis I , tyrosine degradation I , tyrosine degradation II , tyrosine degradation III , tyrosine degradation IV (to 4-methylphenol) :
L-tyrosine + 2-oxoglutarate ↔ 4-hydroxyphenylpyruvate + L-glutamate

(S)-reticuline biosynthesis II , rosmarinic acid biosynthesis II :
L-dopa + 2-oxoglutarate ↔ 3,4-dihydroxyphenylpyruvate + L-glutamate

2'-deoxymugineic acid phytosiderophore biosynthesis :
nicotianamine + 2-oxoglutarate ↔ L-glutamate + 3''-deamino-3''-oxonicotianamine

4-aminobutyrate degradation , 4-aminobutyrate degradation II , 4-aminobutyrate degradation III , glutamate degradation IV , nicotine degradation I :
4-aminobutanoate + 2-oxoglutarate ↔ succinate semialdehyde + L-glutamate

4-aminobutyrate degradation V :
L-glutamate + NAD+ + H2O ↔ 2-oxoglutarate + ammonium + NADH + H+
4-aminobutanoate + 2-oxoglutarate ↔ succinate semialdehyde + L-glutamate

alanine biosynthesis I , valine biosynthesis , valine degradation II :
L-valine + 2-oxoglutarate ↔ L-glutamate + 3-methyl-2-oxobutanoate

alanine biosynthesis II , alanine degradation III :
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate

alanine degradation II (to D-lactate) :
L-glutamate + NAD+ + H2O ↔ 2-oxoglutarate + ammonium + NADH + H+
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate

anaerobic energy metabolism (invertebrates, cytosol) :
L-aspartate + 2-oxoglutarate ↔ L-glutamate + oxaloacetate
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate

arginine biosynthesis II (acetyl cycle) , arginine biosynthesis III (via N-acetyl-L-citrulline) , ornithine biosynthesis :
N-acetyl-L-ornithine + 2-oxoglutarate ↔ L-glutamate + N-acetyl-L-glutamate 5-semialdehyde

arginine biosynthesis IV (archaebacteria) :
an [L-2-aminoadipate carrier protein]-L-ornithine + 2-oxoglutarate ↔ L-glutamate + an [L-2-aminoadipate carrier protein]-L-glutamate 5-semialdehyde

arginine degradation I (arginase pathway) , arginine degradation VI (arginase 2 pathway) , citrulline biosynthesis , L-Nδ-acetylornithine biosynthesis , ornithine degradation II (Stickland reaction) , proline biosynthesis II (from arginine) , proline biosynthesis III :
L-ornithine + 2-oxoglutarate ↔ L-glutamate + L-glutamate-5-semialdehyde

arginine degradation II (AST pathway) :
N2-succinyl-L-ornithine + 2-oxoglutarate ↔ L-glutamate + N2-succinyl-L-glutamate 5-semialdehyde

arginine degradation XI :
L-arginine + 2-oxoglutarate ↔ L-glutamate + 2-ketoarginine

asparagine degradation III (mammalian) , aspartate biosynthesis , aspartate degradation I , aspartate degradation II , glutamate degradation II :
L-aspartate + 2-oxoglutarate ↔ L-glutamate + oxaloacetate

β-alanine degradation I :
β-alanine + 2-oxoglutarate ↔ malonate semialdehyde + L-glutamate

C4 photosynthetic carbon assimilation cycle, NAD-ME type :
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate
L-aspartate + 2-oxoglutarate ↔ L-glutamate + oxaloacetate
L-aspartate + 2-oxoglutarate ↔ L-glutamate + oxaloacetate
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate

C4 photosynthetic carbon assimilation cycle, PEPCK type :
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate
L-aspartate + 2-oxoglutarate ↔ L-glutamate + oxaloacetate
L-aspartate + 2-oxoglutarate ↔ L-glutamate + oxaloacetate
2-oxoglutarate + L-alanine ↔ L-glutamate + pyruvate

CMP-legionaminate biosynthesis I :
GDP-2-acetamido-2,6-dideoxy-α-D-xylo-hexos-4-ulose + L-glutamate ↔ GDP-4-amino-4,6-dideoxy-α-D-N-acetylglucosamine + 2-oxoglutarate

CMP-pseudaminate biosynthesis :
UDP-4-amino-4,6-dideoxy-N-acetyl-β-L-altrosamine + 2-oxoglutarate ↔ UDP-2-acetamido-2,6-dideoxy-β-L-arabino-hexul-4-ose + L-glutamate

coenzyme B biosynthesis :
2-oxoglutarate + acetyl-CoA + H2O ↔ (2R)-homocitrate + coenzyme A + H+

dehydrophos biosynthesis :
1-amino-2-phosphorylethylphosphonate + 2-oxoglutarate ↔ 1-oxo-2-phosphorylethylphosphonate + L-glutamate

dTDP-3-acetamido-3,6-dideoxy-α-D-galactose biosynthesis :
dTDP-3-amino-3,6-dideoxy-α-D-galactopyranose + 2-oxoglutarate ↔ dTDP-3-dehydro-6-deoxy-α-D-galactopyranose + L-glutamate

dTDP-3-acetamido-3,6-dideoxy-α-D-glucose biosynthesis , dTDP-α-D-mycaminose biosynthesis :
dTDP-3-amino-3,6-dideoxy-α-D-glucopyranose + 2-oxoglutarate ↔ dTDP-3-dehydro-6-deoxy-α-D-glucopyranose + L-glutamate

dTDP-β-L-4-epi-vancosamine biosynthesis , dTDP-L-megosamine biosynthesis :
dTDP-3-amino-4-dehydro-2,3,6-trideoxy-α-D-glucose + 2-oxoglutarate ↔ dTDP-3,4-didehydro-2,6-dideoxy-α-D-glucose + L-glutamate

dTDP-D-desosamine biosynthesis :
dTDP-3-amino-3,4,6-trideoxy-α-D-glucopyranose + 2-oxoglutarate ↔ dTDP-3-dehydro-4,6-deoxy-α-D-glucose + L-glutamate
2-oxoglutarate + dTDP-viosamine ↔ L-glutamate + dTDP-4-dehydro-6-deoxy-α-D-glucopyranose

dTDP-D-forosamine biosynthesis :
dTDP-4-oxo-2,3,6-trideoxy-D-glucose + L-glutamate ↔ dTDP-4-amino-2,3,4,6-tetradeoxy-D-glucose + 2-oxoglutarate

dTDP-N-acetylthomosamine biosynthesis :
dTDP-thomosamine + 2-oxoglutarate ↔ dTDP-4-dehydro-6-deoxy-α-D-glucopyranose + L-glutamate

dTDP-N-acetylviosamine biosynthesis :
2-oxoglutarate + dTDP-viosamine ↔ L-glutamate + dTDP-4-dehydro-6-deoxy-α-D-glucopyranose

ectoine biosynthesis , norspermidine biosynthesis , pyoverdine I biosynthesis , rhizobactin 1021 biosynthesis :
L-2,4-diaminobutanoate + 2-oxoglutarate ↔ L-aspartate-semialdehyde + L-glutamate

ethylene biosynthesis IV , glutamate degradation I :
L-glutamate + NAD+ + H2O ↔ 2-oxoglutarate + ammonium + NADH + H+

ethylene biosynthesis V (engineered) , glutamine biosynthesis III , mixed acid fermentation , NAD/NADP-NADH/NADPH cytosolic interconversion (yeast) , TCA cycle I (prokaryotic) , TCA cycle IV (2-oxoglutarate decarboxylase) , TCA cycle VII (acetate-producers) :
D-threo-isocitrate + NADP+2-oxoglutarate + CO2 + NADPH

GABA shunt :
L-glutamate + NAD(P)+ + H2O ↔ 2-oxoglutarate + ammonium + NAD(P)H + H+
4-aminobutanoate + 2-oxoglutarate ↔ succinate semialdehyde + L-glutamate

GDP-D-perosamine biosynthesis :
GDP-α-D-perosamine + 2-oxoglutarate ↔ GDP-4-dehydro-α-D-rhamnose + L-glutamate

glutamate biosynthesis II , glutamate degradation X :
L-glutamate + NAD(P)+ + H2O ↔ 2-oxoglutarate + ammonium + NAD(P)H + H+

glutamate biosynthesis III , nitrate reduction V (assimilatory) , nitrate reduction VI (assimilatory) :
L-glutamate + NADP+ + H2O ↔ ammonium + 2-oxoglutarate + NADPH + H+

glutamate degradation V (via hydroxyglutarate) :
(R)-2-hydroxyglutarate + NAD+2-oxoglutarate + NADH + H+
L-glutamate + NAD+ + H2O ↔ 2-oxoglutarate + ammonium + NADH + H+

histidine degradation IV , imidazole-lactate degradation :
L-histidine + 2-oxoglutarate ↔ L-glutamate + imidazole-pyruvate

homotaurine degradation :
homotaurine + 2-oxoglutarate ↔ 3-sulfopropanal + L-glutamate

hydrogen sulfide biosynthesis I , L-cysteine degradation III :
2-oxoglutarate + L-cysteine ↔ L-glutamate + 3-mercaptopyruvate

incomplete reductive TCA cycle , reductive TCA cycle II :
2-oxoglutarate + 2 an oxidized ferredoxin + coenzyme A ↔ succinyl-CoA + CO2 + 2 a reduced ferredoxin + H+

indole-3-acetate biosynthesis II , tryptophan degradation IV (via indole-3-lactate) , tryptophan degradation VII (via indole-3-pyruvate) , tryptophan degradation VIII (to tryptophol) :
2-oxoglutarate + L-tryptophan ↔ L-glutamate + indole-3-pyruvate

isoleucine biosynthesis I (from threonine) , isoleucine biosynthesis II , isoleucine biosynthesis III , isoleucine biosynthesis IV , isoleucine biosynthesis V , isoleucine degradation I , isoleucine degradation II :
L-isoleucine + 2-oxoglutarate ↔ L-glutamate + (S)-3-methyl-2-oxopentanoate

kanamycin biosynthesis :
2'-deamino-2'-hydroxy-6'-dehydroparomamine + L-glutamate ↔ 2'-deamino-2'-hydroxyneamine + 2-oxoglutarate
neamine + 2-oxoglutarate ↔ 6'-dehydroparomamine + L-glutamate

kanosamine biosynthesis II :
D-kanosamine 6-phosphate + 2-oxoglutarate ↔ 3-dehydro-D-glucose 6-phosphate + L-glutamate

L-cysteine degradation I :
3-sulfinoalanine + 2-oxoglutarate ↔ L-glutamate + 3-sulfinopyruvate

L-dopa degradation :
3-O-methyldopa + 2-oxoglutarate + H+ ↔ 3-methoxy-4-hydroxyphenylpyruvate + L-glutamate

leucine biosynthesis , leucine degradation I , leucine degradation III :
L-leucine + 2-oxoglutarate ↔ L-glutamate + 4-methyl-2-oxopentanoate

lysine biosynthesis I :
2-oxoglutarate + N-succinyl-L,L-2,6-diaminopimelate ↔ L-glutamate + N-succinyl-2-amino-6-ketopimelate

lysine biosynthesis IV :
2-oxoglutarate + acetyl-CoA + H2O ↔ (2R)-homocitrate + coenzyme A + H+
L-2-aminoadipate + 2-oxoglutarate ↔ L-glutamate + 2-oxoadipate

lysine biosynthesis V :
a [LysW]-C-terminal-L-glutamyl-γ-L-lysine + 2-oxoglutarate ↔ a [LysW]-C-terminal-L-glutamyl-γ-L-2-aminoadipate semialdehyde + L-glutamate
2-oxoglutarate + acetyl-CoA + H2O ↔ (2R)-homocitrate + coenzyme A + H+
L-2-aminoadipate + 2-oxoglutarate ↔ L-glutamate + 2-oxoadipate

lysine biosynthesis VI :
L,L-diaminopimelate + 2-oxoglutarate ↔ (S)-2,3,4,5-tetrahydrodipicolinate + L-glutamate + H2O + H+

lysine degradation II (mammalian) , lysine degradation II (pipecolate pathway) , lysine degradation V :
L-2-aminoadipate + 2-oxoglutarate ↔ L-glutamate + 2-oxoadipate

lysine degradation III :
5-aminopentanoate + 2-oxoglutarate ↔ L-glutamate + glutarate semialdehyde
N6-acetyl-L-lysine + 2-oxoglutarate ↔ L-glutamate + 2-keto-6-acetamidocaproate

lysine degradation IV , lysine degradation X :
5-aminopentanoate + 2-oxoglutarate ↔ L-glutamate + glutarate semialdehyde

lysine degradation VI :
2-oxoglutarate + L-lysine ↔ L-glutamate + (S)-2-amino-6-oxohexanoate

methylaspartate cycle :
D-threo-isocitrate + NADP+2-oxoglutarate + CO2 + NADPH
L-glutamate + NAD+ + H2O ↔ 2-oxoglutarate + ammonium + NADH + H+

neomycin biosynthesis :
neomycin C + 2-oxoglutarate ↔ 6'''-deamino-6'''-oxoneomycin C + L-glutamate

nylon-6 oligomer degradation :
6-aminohexanoate + 2-oxoglutarate ↔ 6-oxohexanoate + L-glutamate

ornithine de novo biosynthesis :
L-glutamate + NAD(P)+ + H2O ↔ 2-oxoglutarate + ammonium + NAD(P)H + H+
L-ornithine + 2-oxoglutarate ↔ L-glutamate + L-glutamate-5-semialdehyde

paromomycin biosynthesis :
paromomycin + 2-oxoglutarate ↔ 6'''-oxoparomomycin + L-glutamate

phenylalanine biosynthesis (cytosolic, plants) , phenylalanine biosynthesis I , phenylalanine degradation II (anaerobic) , phenylalanine degradation III :
2-oxo-3-phenylpropanoate + L-glutamate ↔ L-phenylalanine + 2-oxoglutarate

phenylalanine biosynthesis II , tyrosine biosynthesis II , tyrosine biosynthesis III :
L-arogenate + 2-oxoglutarate ↔ prephenate + L-glutamate

phenylalanine degradation IV (mammalian, via side chain) :
L-phenylalanine + 2-oxoglutarate ↔ 2-oxo-3-phenylpropanoate + L-glutamate

photorespiration :
2-oxoglutarate + glycine ↔ L-glutamate + glyoxylate

polymyxin resistance :
UDP-4-amino-4-deoxy-β-L-arabinopyranose + 2-oxoglutarate ↔ UDP-β-L-threo-pentapyranos-4-ulose + L-glutamate

proline biosynthesis IV :
L-ornithine + 2-oxoglutarate ↔ L-glutamate + 2-keto-ornithine

pyridoxal 5'-phosphate biosynthesis I :
2-oxo-3-hydroxy-4-phosphobutanoate + L-glutamate ↔ 4-phospho-hydroxy-L-threonine + 2-oxoglutarate

reductive TCA cycle I :
D-threo-isocitrate + NADP+2-oxoglutarate + CO2 + NADPH
2-oxoglutarate + 2 an oxidized ferredoxin + coenzyme A ↔ succinyl-CoA + CO2 + 2 a reduced ferredoxin + H+

ribostamycin biosynthesis :
neamine + 2-oxoglutarate ↔ 6'-dehydroparomamine + L-glutamate

serine biosynthesis :
3-phospho-L-serine + 2-oxoglutarate ↔ L-glutamate + 3-phospho-hydroxypyruvate

taurine degradation III :
taurine + 2-oxoglutarate ↔ L-glutamate + sulfoacetaldehyde

TCA cycle V (2-oxoglutarate:ferredoxin oxidoreductase) :
D-threo-isocitrate + NADP+2-oxoglutarate + CO2 + NADPH
2-oxoglutarate + 2 an oxidized ferredoxin + coenzyme A ↔ succinyl-CoA + CO2 + 2 a reduced ferredoxin + H+
2-oxoglutarate + an aminated amino group acceptor ↔ L-glutamate + a deaminated amino group acceptor

TCA cycle VI (obligate autotrophs) :
D-threo-isocitrate + NADP+2-oxoglutarate + CO2 + NADPH
L-glutamate + NADP+ + H2O ↔ ammonium + 2-oxoglutarate + NADPH + H+
L-aspartate + 2-oxoglutarate ↔ L-glutamate + oxaloacetate

TCA cycle VIII (helicobacter) :
D-threo-isocitrate + NADP+2-oxoglutarate + CO2 + NADPH
2-oxoglutarate + 2 an oxidized ferredoxin + coenzyme A ↔ succinyl-CoA + CO2 + 2 a reduced ferredoxin + H+

In Reactions of unknown directionality:

Not in pathways:
N-methyl-2-oxoglutaramate + H2O = methylamine + 2-oxoglutarate
D-threo-isocitrate + NAD+ = 2-oxoglutarate + CO2 + NADH
(S)-2-hydroxyglutarate + an oxidized electron acceptor = 2-oxoglutarate + a reduced electron acceptor
2-hydroxyglutarate + FAD + H+ = 2-oxoglutarate + FADH2
L-glutamate + 2 an oxidized ferredoxin + H2O = ammonium + 2-oxoglutarate + 2 a reduced ferredoxin + 2 H+
(R)-2-hydroxyglutarate + an oxidized electron acceptor = 2-oxoglutarate + a reduced electron acceptor
xanthine + 2-oxoglutarate + oxygen = urate + succinate + CO2
(S)-3-hydroxybutanoate + 2-oxoglutarate = (R)-2-hydroxyglutarate + acetoacetate
a [protein] N6,N6-dimethyl-L-lysine + 2-oxoglutarate + oxygen = a [protein] N6-methyl-L-lysine + succinate + formaldehyde + CO2
2-oxoglutarate + coenzyme A + NADP+ = succinyl-CoA + CO2 + NADPH
2-oxoglutarate + glyoxylate + H+ = 2-hydroxy-3-oxoadipate + CO2
lauroyl-CoA + 2-oxoglutarate + H2O = 3-hydroxytetradecane-1,3,4-tricarboxylate + coenzyme A + H+
L-serine + 2-oxoglutarate = L-glutamate + hydroxypyruvate


S-ureidoglycine + a 2-oxo carboxylate = oxalurate + an L-amino acid
a 2-oxo carboxylate + H+ = an aldehyde + CO2
a 2-oxo carboxylate + 2 an oxidized ferredoxin + coenzyme A = an acyl-CoA + CO2 + 2 a reduced ferredoxin + H+
a (2S)-2-hydroxycarboxylate + NAD(P)+ = a 2-oxo carboxylate + NAD(P)H + H+
an L-amino acid + NAD+ + H2O = a 2-oxo carboxylate + ammonium + NADH + H+
an (R)-2-hydroxycarboxylate + NAD+ = a 2-oxo carboxylate + NADH + H+
a (2R)-hydroxy-carboxylate + an oxidized electron acceptor = a 2-oxo carboxylate + a reduced electron acceptor
a (2S)-2-hydroxycarboxylate + NAD+ = a 2-oxo carboxylate + NADH + H+
an (R)-2-hydroxycarboxylate + NADP+ = a 2-oxo carboxylate + NADPH + H+
2-oxoaldehyde + NAD+ + H2O = a 2-oxo carboxylate + NADH + 2 H+
2-oxoaldehyde + NADP+ + H2O = a 2-oxo carboxylate + NADPH + 2 H+


an (R)-2-hydroxyacid + an electron-transfer-related quinone = a 2-oxo acid + an electron-transfer-related quinol


eugenol + a carboxylate + NADP+ = a coniferyl ester + NADPH
a penicillin + H2O = 6-aminopenicillanate + a carboxylate
an aldehyde[periplasmic space] + FAD[periplasmic space] + H2O[periplasmic space] = a carboxylate[periplasmic space] + FADH2[periplasmic space]
an aldehyde + pyrroloquinoline quinone + H2O = a carboxylate + pyrroloquinoline quinol + H+
a nitrile + 2 H2O = a carboxylate + ammonium
an aliphatic nitrile + 2 H2O = a carboxylate + ammonium
an N-acyl-L-homoserine lactone + H2O = L-homoserine lactone + a carboxylate
an aldehyde + an oxidized electron acceptor + H2O = a carboxylate + a reduced electron acceptor + H+
an N-acylated aromatic-L-amino acid + H2O = a carboxylate + an aromatic L-amino acid
an N-acylated-D-amino acid + H2O = a D-amino acid + a carboxylate
an N-acylated aliphatic-L-amino acid + H2O = a carboxylate + an aliphatic L-amino acid
a D-hexose + an acyl phosphate = a D-hexose-phosphate + a carboxylate
an aldehyde + 2 an oxidized ferredoxin + H2O = a carboxylate + 2 a reduced ferredoxin + 3 H+
an aldehyde + NAD(P)+ + H2O = a carboxylate + NAD(P)H + 2 H+
an N-acyl-D-glutamate + H2O = a carboxylate + D-glutamate
an anilide + H2O = aniline + a carboxylate + H+
a 5'-acylphosphoadenosine + H2O = a carboxylate + AMP + 2 H+
a 3-acylpyruvate + H2O = a carboxylate + pyruvate + H+
an N6acyl-L-lysine + H2O = a carboxylate + L-lysine
an N-acyl-D-aspartate + H2O = a carboxylate + D-aspartate

In Transport reactions:
2-oxoglutarate[periplasmic space] + H+[periplasmic space]2-oxoglutarate[cytosol] + H+[cytosol]

In Redox half-reactions:
a 2-oxo carboxylate[in] + ammonium[in] + 2 H+[in] + 2 e- → a D-amino acid[in] + H2O[in]

Enzymes activated by 2-oxoglutarate, sorted by the type of activation, are:

Activator (Allosteric) of: [protein-PII] uridylyltransferase

Activator (Mechanism unknown) of: isocitrate dehydrogenase phosphatase [Nimmo84] , glutamine synthetase deadenylase [Shapiro69, Shapiro68]

Enzymes inhibited by 2-oxoglutarate, sorted by the type of inhibition, are:

Inhibitor (Competitive) of: citrate synthase , α-ketoglutarate reductase [Zhao96, Comment 1] , NADP-dependent isocitrate dehydrogenase [ContrerasShanno05] , indolepyruvate decarboxylase [Koga92]

Inhibitor (Mechanism unknown) of: N-succinyldiaminopimelate aminotransferase [Peterkofsky61] , isocitrate lyase , phosphoenolpyruvate synthetase [Chulavatnatol73] , isocitrate dehydrogenase kinase [Nimmo84] , glutamine synthetase adenylyltransferase [Ebner70, Ebner70a, Helmward89, Comment 2] , arginine kinase [Yao09] , methylglutamate dehydrogenase [Bamforth77] , pyruvate carboxylase [Mukhopadhyay98] , 3,4-dihydroxyphenylalanine oxidative deaminase [Ranjith08] , pyruvate kinase [Plaxton02] , glutamate dehydrogenase (NAD-dependent) [Bonete96]

This compound has been characterized as a cofactor or prosthetic group of the following enzymes: deacetoxycephalosporin C hydroxylase , deacetoxycephalosporin C synthase , deacetoxycephalosporin C hydroxylase , deacetoxycephalosporin C synthase


References

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Ebner70a: Ebner E, Gancedo C, Holzer H "ATP:Glutamine synthetase adenylyltransferase (Escherichia coli B)." Methods in Enzymology 1970; 17A:922-927.

Helmward89: Helmward Z "Handbook of Enzyme Inhibitors. 2nd, revised and enlarged edition." Weinheim, Federal Republic of Germany ; New York, NY, USA , 1989.

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Please cite the following article in publications resulting from the use of MetaCyc: Caspi et al, Nucleic Acids Research 42:D459-D471 2014
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