Ligand 2-oxoadipic acid

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Basic Ligand Information

Molecular Structure
Picture of 2-oxoadipic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C6H8O5
2-oxoadipic acid
FGSBNBBHOZHUBO-UHFFFAOYSA-N
Synonyms:
2-ketoadipate, 2-oxoadipate, 2-oxoadipinate, 2-oxohexane-1,6-dioate, 2-oxohexanedioate, 2-oxohexanedioic acid, alpha-ketoadipate


Show all pahtways known for Show all BRENDA pathways known for 2-oxoadipic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxoadipate + NADH = 2-hydroxyadipate + NAD+
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-alpha-aminoadipate + H2O + O2 = 2-oxoadipate + NH3 + H2O2
show the reaction diagram
-
-
L-2-aminoadipate + 2-oxoglutarate = 2-oxoadipate + L-glutamate
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (33 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-oxoadipate + NADH = 2-hydroxyadipate + NAD+
show the reaction diagram
-
taurine + alpha-ketoadipate + O2 = sulfite + aminoacetaldehyde + pentan-1,5-dioic acid + CO2
show the reaction diagram
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xanthine + 2-oxoadipate + O2 = ?
show the reaction diagram
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naringenin + 2-oxoadipate + O2 = dihydrokaempferol + pentanedioate + CO2
show the reaction diagram
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2-oxoadipate + CoA + 2 methyl viologen = ?
show the reaction diagram
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2-oxoadipate + CoA + 2 methyl viologen = glutaryl-CoA + CO2 + 2 reduced methyl viologen + 2 H+
show the reaction diagram
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2-oxoadipate + NADPH + NH3 = L-2-aminoadipate + NADP+ + H2O
show the reaction diagram
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L-lysine + alpha-ketoadipate + NADH = ?
show the reaction diagram
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acetyl-CoA + H2O + 2-oxoadipate = 2-hydroxyhexane-1,2,6-tricarboxylate
show the reaction diagram
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N2-acetyl-L-ornithine + 2-oxohexanedioic acid = N-acetyl-L-glutamate 5-semialdehyde + 2-aminohexanedioic acid
show the reaction diagram
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L-lysine + 2-oxoadipate = 2-aminoadipate 6-semialdehyde + L-homoglutarate
show the reaction diagram
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2-oxoadipate + L-glutamate = L-2-aminoadipate + 2-oxoglutarate
show the reaction diagram
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L-glutamine + 2-oxoadipate = 2-oxoglutaramate + L-2-amino-1,6-hexandioate
show the reaction diagram
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L-phenylalanine + 2-oxoadipate = phenylpyruvate + L-2-aminoadipate
show the reaction diagram
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L-histidinol phosphate + 2-oxoadipate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + 2-aminoadipate
show the reaction diagram
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succinyl-CoA + 2-oxoadipate = succinate + 2-oxoadipyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (23 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-alpha-aminoadipic acid + H2O + O2 = 2-oxoadipic acid + NH3 + H2O2
show the reaction diagram
-
-
D-alpha-aminoadipate + H2O + O2 = 2-oxoadipate + NH3 + H2O2
show the reaction diagram
-
-
glyoxylate + butyryl-CoA + H2O = 2-oxohexanedioic acid + CoA
show the reaction diagram
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2-aminohexanedioic acid + 2-oxoglutarate = 2-oxohexanedioic acid + L-glutamate
show the reaction diagram
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L-2-aminohexane-1,6-dioate + 2-oxoglutarate = 2-oxohexane-1,6-dioate + L-glutamate
show the reaction diagram
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3-(imidazol-4-yl)-2-oxopropyl phosphate + L-2-aminoadipate = L-histidinol phosphate + 2-oxoadipate
show the reaction diagram
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alpha-ketoadipinyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + alpha-ketoadipate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
required for reductive carboxylation
-

Inhibitor in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
38% inhibition at 2.5 mM
-
38% inhibition at 2.5 mM, 58% inhibition at 5 mM
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competitive with respect to DL-4-carboxy-4-hydroxy-2-oxoadipate
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maximal inhibition of 40% (highest inhibition achieved relative to that in absence of inhibitor by varying the concentration of the inhibitor at a given concentration of other substrates pyruvate 0.5 mM and 0.4 mM L-aspartate-4-semialdehyde), in a coupled assay with recombinant dihydrodipicolinate reductase
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3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (5 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
7.6
-
25°C, pH 7.4, recombinant enzyme isolated from Escherichia coli
22.3
-
pH 7.5, 45°C
4.84
-
in 100 mM potassium phosphate buffer (pH 7.4), at 37°C

KM Value (20 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2.6
-
-
1.5
-
-
0.14
-
as cosubstrate
0.16
-
25°C, pH 7.4, recombinant enzyme isolated from Escherichia coli
1.4
-
-
5.3
-
at pH 7.0
1.24
-
-
0.1
-
pH 7.0, 22°C
25
-
pH 8.0, 25°C

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1
-
competitive inhibition with respect to 2-oxoglutarate and noncompetitive with respect to Fe2+ and the peptide substrate
5.3
-
at pH 7.0

References & Links

Links to other databases for 2-oxoadipic acid

ChEBI
PubChem
ChEBI
PubChem