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Ligand 3-oxoadipic acid

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

BRENDA

3-chlorocatechol degradation, 4-hydroxymandelate degradation, aerobic toluene degradation, resorcinol degradation

KEGG

Benzoate degradation, Degradation of aromatic compounds, Microbial metabolism in diverse environments

MetaCyc

1,4-dichlorobenzene degradation, 2,4,5-trichlorophenoxyacetate degradation, 2,4,6-trichlorophenol degradation, 3,4,6-trichlorocatechol degradation, 3,5-dichlorocatechol degradation, 3-chlorocatechol degradation I (ortho), 3-chlorocatechol degradation II (ortho), 3-oxoadipate degradation, 4,5-dichlorocatechol degradation, 4-aminophenol degradation, 4-chlorocatechol degradation, 4-hydroxyacetophenone degradation, 4-nitrophenol degradation I, 4-nitrophenol degradation II, 4-sulfocatechol degradation, catechol degradation to beta-ketoadipate, chlorosalicylate degradation, gamma-hexachlorocyclohexane degradation, gamma-resorcylate degradation I, gamma-resorcylate degradation II, pentachlorophenol degradation, pinoresinol degradation, protocatechuate degradation II (ortho-cleavage pathway), resorcinol degradation more

Show all BRENDA pathways known for 3-oxoadipic acid

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Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Natural Substrate (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.8.3.6

3-oxoadipate + succinyl-CoA = 3-oxoadipyl-CoA + succinate

671471

-

2.8.3.6

succinyl-CoA + 3-oxoadipate = ?

646000, 646001, 645997, 645998

-

2.8.3.6

succinyl-CoA + 3-oxoadipate = succinate + 3-oxoadipyl-CoA

738724, 739654, 704325

-

2.8.3.6

3 entries

In Vivo Product in Enzyme-catalyzed Reactions (7 results)

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Show Natural Product (7 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.32

2-maleylacetate + NAD(P)H + H+ = 3-oxoadipate + NAD(P)+

0

-

1.3.1.32

2-maleylacetate + NAD(P)H = 3-oxoadipate + NAD(P)+

0

-

1.3.1.32

2-maleylacetate + NADH + H+ = 3-oxoadipate + NAD+

0

-

1.3.1.32

2-maleylacetate + NADPH + H+ = 3-oxoadipate + NADP+

0

-

1.3.1.32

2-maleylacetate + NADPH = 3-oxoadipate + NADP+

0

-

1.3.1.32

maleylacetate + NADH = 3-oxoadipate + NAD+

0

-

1.3.1.32

6 entries

3.1.1.24

3-oxoadipate enol-lactone + H2O = 3-oxoadipate

0

-

Substrate in Enzyme-catalyzed Reactions (3 results)

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Show Substrate (3 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.8.3.6

3-oxoadipate + succinyl-CoA = 3-oxoadipyl-CoA + succinate

671471

-

2.8.3.6

succinyl-CoA + 3-oxoadipate = ?

646000, 646001, 645997, 645998

-

2.8.3.6

succinyl-CoA + 3-oxoadipate = succinate + 3-oxoadipyl-CoA

645996, 94277, 645997, 645998, 646000, 738724, 739654, 646002, 704325

-

2.8.3.6

3 entries

Product in Enzyme-catalyzed Reactions (12 results)

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Show Product (12 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.3.1.32

2-fluoromaleylacetate + NADH = 3-oxoadipate + NAD+ + F-

390701

-

1.3.1.32

2-maleylacetate + NAD(P)H + H+ = 3-oxoadipate + NAD(P)+

0

-

1.3.1.32

2-maleylacetate + NAD(P)H = 3-oxoadipate + NAD(P)+

0

-

1.3.1.32

2-maleylacetate + NADH + H+ = 3-oxoadipate + NAD+

0

-

1.3.1.32

2-maleylacetate + NADH = 3-oxoadipate + NAD+

0

-

1.3.1.32

2-maleylacetate + NADPH + H+ = 3-oxoadipate + NADP+

0

-

1.3.1.32

2-maleylacetate + NADPH = 3-oxoadipate + NADP+

0

-

1.3.1.32

maleylacetate + NADH = 3-oxoadipate + NAD+

0

-

1.3.1.32

8 entries

2.6.1.42

DL-2-aminoadipate + 2-oxoglutarate = 3-oxohexanedioic acid + L-glutamate

0

-

3.1.1.24

(5-oxo-4,5-dihydrofuran-2-yl)acetic acid + H2O = 3-oxoadipate

0

-

3.1.1.24

3-oxoadipate enol-lactone + H2O = 3-oxoadipate

0

-

3.1.1.24

3-oxoadipate-enol-lactone + H2O = 3-oxoadipate

0

-

3.1.1.24

3 entries

Inhibitor in Enzyme-catalyzed Reactions (6 results)

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Show Inhibitors (6 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.11.3

50% inhibition at 2.5 mM

439174

-

1.14.20.1

0.1 mM, 56% inhibition

440378

-

1.3.1.32

competitive inhibition

390700

-

2.6.1.31

inhibition at pH 7.0 is higher than at pH 8.5, 3.33 mM in presence of equimolar concentrations of oxaloacetate

639962

-

3.1.1.24

10% inhibition at a concentration of 1 mM; 50% inhibition at a concentration of 10 mM; i.e. beta-ketoadipate

94277

-

3.1.1.24

50% inhibition at a concentration of 17 mM; i.e. beta-ketoadipate

94277

-

3.1.1.24

2 entries

Enzyme Kinetic Parameters

K_M Value (1 result)

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Show KM Value (1 entry)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.8.3.6

0.4

-

pH 8, 25°C

646002

K_i Value (3 results)

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Show KI Value (3 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.3.1.32

1.8

-

-

390700

3.1.1.24

10

-

-

94277

3.1.1.24

17

-

-

94277

3.1.1.24

2 entries

References & Links

Literature References (16)

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Show Reference (16 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

94277

6591865

p-Chloromercuribenzoate specifically modifies thiols associated with the active sites of beta-ketoadipate enol-lactone hydrolase and succinyl CoA: beta-ketoadipate CoA transferase

1984

Yeh, W.K.; Ornston, L.N.

Arch. Microbiol.

138

102-105

390700

8226615

Purification and characterization of maleylacetate reductase from Alcaligenes eutrophus JMP134(pJP4)

1993

Seibert, V.; Stadler-Fritzsche, K.; Schloemann, M.

J. Bacteriol.

175

6745-6754

390701

7814320

Maleylacetate reductase of Pseudomonas sp. strain B13: specificity of substrate conversion and halide elimination

1995

Kaschabek, S.R.; Reineke, W.

J. Bacteriol.

177

320-325

439174

4265566

Thymidine 2-hydroxylation in Neurospora crassa

1972

Bankel, L.; Lindstedt, G.; Lindstedt, S.

J. Biol. Chem.

247

6128-6134

440378

3446748

Purification and characterization of a 2-oxoglutarate-linked ATP-independent deacetoxycephalosporin C synthase of Streptomyces lactamdurans

1987

Cortes, J.; Martin, J.F.; Castro, J.M.; Laiz, L.; Liras, P.

J. Gen. Microbiol.

133

3165-3174

639962

14189882

Pyridoxamine-oxaloacetic transaminase of rat kidney

1964

Wu, H.L.C.; Mason, M.

J. Biol. Chem.

239

1492-1497

645996

13428776

Enzymatic degradation of beta-ketoadipic acid

1957

Katagiri, M.; Hayaishi, O.

J. Biol. Chem.

226

439-448

645997

6780551

Evolutionarily homologous alpha 2 beta 2 oligomeric structures in beta-ketoadipate succinyl-CoA transferases from Acinetobacter calcoaceticus and Pseudomonas putida

1981

Yeh, W.K.; Ornston, L.N.

J. Biol. Chem.

256

1565-1569

645998

6172419

Similar structures in gamma-carboxymuconolactone decarboxylase and beta-ketoadipate succinyl coenzyme A transferase

1982

Yeh, W.K.; Ornston, L.N.

J. Bacteriol.

149

374-377

646000

1624453

Characterization of the genes encoding beta-ketoadipate: succinyl-coenzyme A transferase in Pseudomonas putida

1992

Parales, R.E.; Harwood, C.S.

J. Bacteriol.

174

4657-4666

646001

11741863

Degradation of aromatics and chloroaromatics by Pseudomonas sp. strain B13: cloning, characterization, and analysis of sequences encoding 3-oxoadipate:succinyl-coenzyme A (CoA) transferase and 3-oxoadipyl-CoA thiolase

2002

Gobel, M.; Kassel-Cati, K.; Schmidt, E.; Reineke, W.

J. Bacteriol.

184

216-223

646002

11741862

Degradation of aromatics and chloroaromatics by Pseudomonas sp. strain B13: purification and characterization of 3-oxoadipate:succinyl-coenzyme A (CoA) transferase and 3-oxoadipyl-CoA thiolase

2002

Kaschabek, S.R.; Kuhn, B.; Muller, D.; Schmidt, E.; Reineke, W.

J. Bacteriol.

184

207-215

671471

16885292

Characterization of the beta-ketoadipate pathway in Sinorhizobium meliloti

2006

MacLean, A.M.; MacPherson, G.; Aneja, P.; Finan, T.M.

Appl. Environ. Microbiol.

72

5403-5413

704325

20061479

Modified 3-oxoadipate pathway for the biodegradation of methylaromatics in Pseudomonas reinekei MT1

2010

Marin, M.; Perez-Pantoja, D.; Donoso, R.; Wray, V.; Gonzalez, B.; Pieper, D.H.

J. Bacteriol.

192

1543-1552

738724

26723258

Beta-ketoadipic acid and muconolactone production from a lignin-related aromatic compound through the protocatechuate 3,4-metabolic pathway

2016

Okamura-Abe, Y.; Abe, T.; Nishimura, K.; Kawata, Y.; Sato-Izawa, K.; Otsuka, Y.; Nakamura, M.; Kajita, S.; Masai, E.; Sonoki, T.; Katayama, Y.

J. Biosci. Bioeng.

121

652-658

739654

26672484

A functional 4-hydroxybenzoate degradation pathway in the phytopathogen Xanthomonas campestris is required for full pathogenicity

2015

Wang, J.; Zhou, L.; Chen, B.; Sun, S.; Zhang, W.; Li, M.; Tang, H.; Jiang, B.; Tang, J.; He, Y.

Sci. Rep.

5

18456

Links to other databases for 3-oxoadipic acid

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Show Links (1 entry)

ChEBI

PubChem