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Ligand adipic acid

Basic Ligand Information

Molecular Structure

Related pathways

Show all BRENDA pathways known for adipic acid

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Roles as Enzyme Ligand

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

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Show Natural Product (3 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.2.1.63

6-oxohexanoate + NADP+ + H2O = adipate + NADPH

7430, 246371, 288310

-

3.5.1.93

adipyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + adipate

-

-

3.5.5.1

adiponitrile + 2 H2O = adipic acid + NH3

-

-

Substrate in Enzyme-catalyzed Reactions (16 results)

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Show Substrate (16 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.2.1.95

adipate + NADPH + H+ + ATP = adipate semialdehyde + NADP+ + AMP + diphosphate

288201

-

2.8.3.12

glutaconyl-CoA + adipate = glutaconate + adipyl-CoA

645952

-

2.8.3.13

3-hydroxy-3-methylglutaryl-CoA + adipate = 3-hydroxy-3-methylglutarate + adipyl-CoA

643834

-

2.8.3.13

glutaryl-CoA + adipate = glutarate + adipyl-CoA

643834

-

2.8.3.13

malonyl-CoA + adipate = malonate + adipyl-CoA

643834

-

2.8.3.13

methylmalonyl-CoA + adipate = methylmalonate + adipyl-CoA

643834

-

2.8.3.13

succinyl-CoA + adipate = succinate + adipyl-CoA

643834

-

2.8.3.13

5 entries

3.1.1.3

glycerol + 1,8-octanediol + adipic acid = ?

691189

-

3.1.1.74

1,4-butanediol + adipic acid = ?

681736

-

3.1.1.74

1,4-cyclohexanedimethanol + adipic acid = ?

681736

-

3.1.1.74

1,8-octanediol + adipic acid = ?

681736

-

6.2.1.14

ATP + adipate + CoA = AMP + diphosphate + adipyl-CoA

745844

-

6.2.1.14

ATP + hexanedioate + CoA = AMP + diphosphate + hexanedioyl-CoA

649669

-

3.1.1.74

3 entries

6.2.1.14

2 entries

6.2.1.23

ATP + hexanedioic acid + CoA = AMP + diphosphate + hexanedioyl-CoA

701

-

6.2.1.5

ATP + adipate + CoA = ADP + phosphate + adipyl-CoA

674857

-

6.3.1.2

ATP + adipate + NH4+ = ADP + phosphate + ?

743570

-

Product in Enzyme-catalyzed Reactions (29 results)

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Show Product (29 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.2.1.63

6-oxohexanoate + NADP+ + H2O = adipate + NADPH

7430, 246371, 288310

-

1.3.1.31

2-hexenedioic acid + NADH + H+ = adipic acid + NAD+

-

-

2.6.1.36

L-lysine + 2-oxoadipate = 2-aminoadipate 6-semialdehyde + L-homoglutarate

-

-

2.8.3.13

adipyl-CoA + 3-hydroxy-3-methylglutarate = adipate + 3-hydroxy-3-methylglutaryl-CoA

643834

-

2.8.3.13

adipyl-CoA + glutarate = adipate + glutaryl-CoA

643834

-

2.8.3.13

adipyl-CoA + malonate = adipate + malonyl-CoA

643834

-

2.8.3.13

adipyl-CoA + methylmalonate = adipate + methylmalonyl-CoA

643834

-

2.8.3.13

adipyl-CoA + succinate = adipate + succinyl-CoA

643834

-

2.8.3.13

5 entries

3.1.1.74

ethyl adipate + H2O = ethanol + adipate

-

-

3.1.1.8

adipyldicholine + H2O = adipic acid + choline

-

-

3.5.1.13

adipic acid bishexylamide + H2O = adipic acid + dihexylamine

-

-

3.5.1.4

5-[(5-carboxypentanoyl)amino]-2-nitrobenzoic acid + H2O = 2-nitrobenzoate + adipate

-

-

3.5.1.4

adipoamide + H2O = adipic acid + NH3

-

-

3.5.1.93

adipyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanate + adipate

-

-

3.5.1.93

adipyl-7-aminocephalosporanic acid + H2O = 7-aminocephalosporanic acid + adipate

-

-

3.5.1.93

adipyl-7-aminocephalosporanic acid + H2O = adipate + 7-aminocephalosporanate

-

-

3.5.1.93

adipyl-7-aminodeacetoxycephalosporanic acid + H2O = adipate + 7-aminodeacetoxycephalosporanic acid

-

-

3.5.1.93

adipyl-7-aminodesacetoxycephalosporanic acid + H2O = adipate + 7-aminodesacetoxycephalosporanate

-

-

3.5.1.93

adipyl-7-aminodesacetoxycephalosporanic acid + H2O = deacetoxycephalosporanic acid + adipate

-

-

3.5.1.93

adipyl-aminopenicillanic acid + H2O = adipate + aminopenicillanic acid

-

-

3.5.5.1

adiponitrile + 2 H2O = adipic acid + 2 NH3

-

-

3.5.5.1

adiponitrile + 2 H2O = adipic acid + NH3

-

-

3.5.5.1

adiponitrile + H2O = adipic acid + NH3

32507, 209747, -

-

3.5.5.1

1,4-dicyanobutane + H2O = hexanedioic acid + NH3

-

-

3.5.5.5

1,4-dicyanobutane + H2O = adipic acid + NH3

-

-

3.5.5.5

adiponitrile + H2O = adipic acid + NH3

-

-

3.5.5.7

adiponitrile + H2O = adipate + NH3

-

-

3.5.5.7

adiponitrile + 4 H2O = adipic acid + 2 NH3

-

-

3.5.5.7

adiponitrile + H2O = adipic acid + NH3

-

-

3.5.1.4

2 entries

3.5.1.93

7 entries

3.5.5.1

4 entries

3.5.5.5

2 entries

3.5.5.7

3 entries

Activator in Enzyme-catalyzed Reactions (1 result)

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Show Activating Compound (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

4.1.2.4

activates

5168

-

Inhibitor in Enzyme-catalyzed Reactions (23 results)

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Show Inhibitors (23 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.14.11.2

competitive inhibitor with respect to 2-oxoglutarate, noncompetitive with respect to Fe2+

439193

-

1.14.11.7

-

349014

-

1.4.1.2

-

727059

-

1.4.3.1

at 6.67 mM 15% inhibition

391727

-

1.5.1.7

-

685171

-

2.6.1.1

moderately

639860

-

2.6.1.1

no inhibition

639814

-

2.6.1.1

2 entries

2.6.1.19

-

637035

-

2.6.1.31

not at pH 7.0, weak at pH 8.0

639962

-

2.6.1.39

6 mM, 48% inhibition

639979

-

2.6.1.39

6 mM, 60% inhibition

639979

-

2.6.1.39

competitive inhibition with respect to L-kynurenine, but not to 2-oxoglutarate

639975

-

2.6.1.39

3 entries

2.6.1.6

-

640167

-

2.6.1.7

-

636608, 636621

-

2.6.1.7

10 mM, 39% inhibition

636613

-

2.6.1.7

strong inhibition

636623

-

2.6.1.7

3 entries

2.8.3.6

inhibits the enzyme at concentration above 10 mM, activates at 2 mM

671471

-

3.4.11.14

-

647030

-

4.1.1.20

-

653897

-

4.2.1.3

-

33790

-

4.2.1.84

-

648435

-

4.2.1.84

not inhibitory

648447

-

4.2.1.84

2 entries

5.5.1.5

-

3718

-

3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (3 entries)

EC NUMBER

ENZYME 3D STRUCTURE

3.1.1.29

4DHW, 3D-view

3.4.25.1

4JT0, 3D-view

4.1.1.77

5D2J, 3D-view

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

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Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.2.1.95

0.0045

-

pH 8.8, 37°C

288201

6.2.1.14

0.0066

-

pH and temperature not specified in the publication

745844

K_M Value (7 results)

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Show KM Value (7 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.2.1.95

10

-

pH 8.8, 37°C

288201

2.8.3.12

8

-

cosubstrate glutaconyl-CoA

645952

2.8.3.13

0.39

-

pH 7.8, 30°C, cosubstrate 3-hydroxy-3-methylglutaryl-CoA , reverse reaction

643834

2.8.3.13

0.72

-

pH 7.8, 30°C, cosubstrate glutaryl-CoA

643834

2.8.3.13

0.83

-

pH 7.8, 30°C, cosubstrate malonylCoA

643834

2.8.3.13

1.32

-

pH 7.8, 30°C, cosubstrate succinylCoA

643834

2.8.3.13

1.51

-

pH 7.8, 30°C, cosubstrate methylmalonyl-CoA

643834

2.8.3.13

5 entries

K_i Value (8 results)

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Show KI Value (8 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.14.11.2

15

-

value above

439193

1.14.11.7

6

-

-

349014

1.4.1.2

35

-

pH 8.0, 40°C, Ki(slope), at 2.5 mM NAD+

727059

1.5.1.7

50

-

at pH 7.0

685171

2.6.1.7

13

-

-

636613

4.1.1.20

0.13

-

-

653897

4.2.1.84

35

-

R312 strain

648435

4.2.1.84

220

-

ACV2 mutant

648435

4.2.1.84

2 entries

References & Links

Literature References (41)

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Show Reference (41 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

701

4062873

The microsomal dicarboxylyl-CoA synthetase

1985

Vamecq, J.; de Hoffmann, E.; van Hoof, F.

Biochem. J.

230

683-693

3718

240704

Metabolism of aromatic compounds by fungi. Kinetic properties and mechanism of 3-carboxy-cis,cis-muconate cyclase from Aspergillus niger

1975

Thatcher, D.R.; Cain, R.B.

Eur. J. Biochem.

56

193-204

5168

6016328

Deoxyribose 5-phosphate aldolase. II. Purification and properties of the rat liver enzyme

1967

Groth, D.P.

J. Biol. Chem.

242

155-159

7430

856571

The metabolism of trans-cyclohexan-1,2-diol by an Acinetobacter species

1977

Davey, J.F.; Trudgill, P.W.

Eur. J. Biochem.

74

115-127

32507

7642130

Aliphatic nitrilase from a soil-isolated Comamonas testosteroni sp.: gene cloning and overexpression, purification and primary structure

1995

Levy-Schil, S.; Soubrier, F.; Crutz-Le Coq, A.M.; Faucher, D.; Crouzet, J.; Petre, D.

Gene

161

15-20

33790

-

Etude de quelques proprietes de l'aconitase de la levure Saccharomycopsis lipolytica

1978

Treton, B.; Heslot, H.

Agric. Biol. Chem.

42

1201-1206

209747

-

Transformation of aliphatic and aromatic nitriles by a nitrilase from Pseudomonas sp.

1999

Dhillon, J.; Chhatre, S.; Shanker, R.; Shivaraman, N.

Can. J. Microbiol.

45

811-815

246371

1261

The metabolism of cyclohexanol by Acinetobacter NCIB 9871

1975

Donoghue, N.A.; Trudgill, P.W.

Eur. J. Biochem.

60

1-7

288201

10320345

Lysine biosynthesis in Saccharomyces cerevisiae: mechanism of alpha-aminoadipate reductase (Lys2) involves posttranslational phosphopantetheinylation by Lys5

1999

Ehmann, D.E.; Gehring, A.M.; Walsh, C.T.

Biochemistry

38

6171-6177

288310

10543838

Identification of a transcriptional activator (ChnR) and a 6-oxohexanoate dehydrogenase (ChnE) in the cyclohexanol catabolic pathway in Acinetobacter sp. strain NCIMB 9871 and localization of the genes that encode them

1999

Iwaki, H.; Hasegawa, Y.; Teraoka, M.; Tokuyama, T.; Bergeron, H.; Lau, P.C.K.

Appl. Environ. Microbiol.

65

5158-5162

349014

2994628

Differences between collagen hydroxylases and 2-oxoglutarate dehydrogenase in their inhibition by structural analogues of 2-oxoglutarate

1985

Majamaa, K.; Turpeenniemi-Hujanen, T.M.; Latipää, P.; Gunzler, V.; Hanauske-Abel, H.M.; Hassinen, I.E.; Kivirikko, K.I.

Biochem. J.

229

127-133

391727

6060479

D-aspartate oxidase of kidney

1967

Dixon, M.; Kenworthy, P.

Biochim. Biophys. Acta

146

54-76

439193

6321169

The 2-oxoglutarate binding site of prolyl 4-hydroxylase. Identification of distinct subsites and evidence for 2-oxoglutarate decarboxylation in a ligand reaction at the enzyme-bound ferrous ion

1984

Majamaa, K.; Hanauske-Abel, H.M.; Gunzler, V.; Kivirikko, K.I.

Eur. J. Biochem.

138

239-245

636608

3037259

Kynurenine-oxoglutarate aminotransferase from rat kidney

1987

Tobes, M.C.

Methods Enzymol.

142

217-224

636613

3086302

Purification and characterization of yeast L-kynurenine aminotransferase with broad substrate specificity

1986

Asada, Y.; Sawa, Y.; Tanizawa, K.; Soda, K.

J. Biochem.

99

1101-1110

636621

-

Purification and properties of kynurenine aminotransferase from rat kidney

1991

Mawal, M.R.; Mukhopadhyay, A.; Deshmukh, D.R.

Biochem. J.

279

595-599

636623

6830814

Purification, characterization and identification of rat liver mitochondrial kynurenine aminotransferase with alpha-aminoadipate aminotransferase

1983

Takeuchi, F.; Otsuka, H.; Shibata, Y.

Biochim. Biophys. Acta

743

323-330

637035

4156051

Subunit structure and kinetic properties of 4-aminobutyrate-2-ketoglutarate transaminase purified from mouse brain

1974

Schousboe, A.; Wu, J.Y.; Roberts, E.

J. Neurochem.

23

1189-1195

639814

3879173

Aspartate: 2-oxoglutarate aminotransferase from trichomonas vaginalis. Identity of aspartate aminotransferase and aromatic amino acid aminotransferase

1985

Lowe, P.N.; Rowe, A.F.

Biochem. J.

232

689-695

639860

-

Purification and some properties of aspartate aminotransferase of Methanobacterium thermoformicicum SF-4

1990

Tanaka, T.; Tokuda, T.; Tachibana, A.; Taniguchi, M.; Oi, S.

Agric. Biol. Chem.

54

625-631

639962

14189882

Pyridoxamine-oxaloacetic transaminase of rat kidney

1964

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

J. Biol. Chem.

239

1492-1497

639975

1111529

L-kynurenine aminotransferase and L-alpha-aminoadipate aminotransferase. I. Evidence for identity

1975

Tobes, M.C.; Mason, M.

Biochem. Biophys. Res. Commun.

62

390-397

639979

2803240

Purification and properties of 2-aminoadipate: 2-oxoglutarate aminotransferase from bovine kidney

1989

Deshmukh, D.R.; Mungre, S.M.

Biochem. J.

261

761-768

640167

-

Purification and properties of leucine aminotransferase from soybean seedlings

1987

Pathre, U.; Singh, A.K.; Viswanathan, P.N.; Sane, P.V.

Phytochemistry

26

2913-2917

643834

1610380

Substrate specificity of a dicarboxyl-CoA: dicarboxylic acid coenzyme A transferase from rat liver mitochondria

1992

Deana, R.

Biochem. Int.

26

767-773

645952

6945182

Glutaconate CoA-transferase from Acidaminococcus fermentans

1981

Buckel, W.; Dorn, U.; Semmler, R.

Eur. J. Biochem.

118

315-321

647030

900951

Hydrophobic binding sites of human liver alanine aminopeptidase

1977

Garner, C.W.; Behal, F.J.

Arch. Biochem. Biophys.

182

667-673

648435

-

Purification and characterization of nitrile hydratase of a mutant strain of Brevibacterium sp.

1993

Moreau, J.L.; Azza, S.; Arnaud, A.; Galzy, P.

J. Basic Microbiol.

33

323-329

648447

8797859

Key role of alkanoic acids on the spectral properties, activity, and active-site stability of iron-containing nitrile hydratase from Brevibacterium R312

1996

Kopf, M-A.; Bonnet, D.; Artaud, I.; Pétré, D.; Mansuy, D.

Eur. J. Biochem.

240

239-244

649669

-

Purification, characterization, DNA sequence and cloning of a pimeloyl-CoA synthetase from Pseudomonas mendocina 35

1999

Binieda, A.; Fuhrmann, M.; Lehner, B.; Rey-Berthod, C.; Frutiger-Hughes, S.; Hughes, G.; Shaw, N.M.

Biochem. J.

340

793-801

653897

12429091

Cocrystal structures of diaminopimelate decarboxylase: mechanism, evolution, and inhibition of an antibiotic resistance accessory factor

2002

Ray, S.S.; Bonanno, J.B.; Rajashankar, K.R.; Pinho, M.G.; He, G.; De Lencastre, H.; Tomasz, A.; Burley, S.K.

Structure

10

1499-1508

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

674857

17640871

A novel ADP-forming succinyl-CoA synthetase in Thermococcus kodakaraensis structurally related to the archaeal nucleoside diphosphate-forming acetyl-CoA synthetases

2007

Shikata, K.; Fukui, T.; Atomi, H.; Imanaka, T.

J. Biol. Chem.

282

26963-26970

681736

-

A cutinase with polyester synthesis activity

2007

Hunsen, M.; Azim, A.; Mang, H.; Wallner, S.R.; Ronkvist, A.; Xie, W.; Gross, R.A.

Macromolecules

40

148-150

685171

17542618

Determinants of substrate specificity for saccharopine dehydrogenase from Saccharomyces cerevisiae

2007

Xu, H.; West, A.H.; Cook, P.F.

Biochemistry

46

7625-7636

691189

18197630

Candida antarctica lipase B chemically immobilized on epoxy-activated micro- and nanobeads: catalysts for polyester synthesis

2008

Chen, B.; Hu, J.; Miller, E.M.; Xie, W.; Cai, M.; Gross, R.A.

Biomacromolecules

9

463-471

727059

8605224

NAD-glutamate dehydrogenase from Halobacterium halobium: inhibition and activation by TCA intermediates and amino acids

1996

Bonete, M.J.; Perez-Pomares, F.; Ferrer, J.; Camacho, M.L.

Biochim. Biophys. Acta

1289

14-24

743570

29320490

The glutamine synthetase of Trypanosoma cruzi is required for its resistance to ammonium accumulation and evasion of the parasitophorous vacuole during host-cell infection

2018

Crispim, M.; Damasceno, F.S.; Hernandez, A.; Barison, M.J.; Pretto Sauter, I.; Souza Pavani, R.; Santos Moura, A.; Pral, E.M.F.; Cortez, M.; Elias , M.C.; Silber, A.M.

PLOS Negl. Trop. Dis.

10

e0006170

743570

29320490

The glutamine synthetase of Trypanosoma cruzi is required for its resistance to ammonium accumulation and evasion of the parasitophorous vacuole during host-cell infection

2018

Crispim, M.; Damasceno, F.S.; Hernandez, A.; Barison, M.J.; Pretto Sauter, I.; Souza Pavani, R.; Santos Moura, A.; Pral, E.M.F.; Cortez, M.; Elias , M.C.; Silber, A.M.

PLOS Negl. Trop. Dis.

10

e0006170

745844

28414710

Using the pimeloyl-CoA synthetase adenylation fold to synthesize fatty acid thioesters

2017

Wang, M.; Moynie, L.; Harrison, P.J.; Kelly, V.; Piper, A.; Naismith, J.H.; Campopiano, D.J.

Nat. Chem. Biol.

13

660-667

745844

28414710

Using the pimeloyl-CoA synthetase adenylation fold to synthesize fatty acid thioesters

2017

Wang, M.; Moynie, L.; Harrison, P.J.; Kelly, V.; Piper, A.; Naismith, J.H.; Campopiano, D.J.

Nat. Chem. Biol.

13

660-667

743570

2 entries

745844

2 entries

Links to other databases for adipic acid

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Show Links (1 entry)