print visible entries

print all entries

Ligand 2-aminoadipic acid

Basic Ligand Information

Molecular Structure

Pathway Source

Pathways

MetaCyc

isopenicillin N biosynthesis, L-lysine biosynthesis IV, L-lysine biosynthesis V, L-lysine degradation II (L-pipecolate pathway), L-lysine degradation V, L-lysine degradation VI, L-lysine degradation XI, penicillin G and penicillin V biosynthesis, penicillin K biosynthesis more

close all tables

open all tables

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

top print hide

Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.6.1.57

alpha-aminoadipate + 2-oxoglutarate = 2-oxoadipate + L-glutamate

759287

-

6.3.2.26

alpha-aminoadipic acid + L-valine + L-lysine + ? = L-delta-alpha-aminoadipyl-L-cysteinyl-D-valine + ?

700004

-

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

top print hide

Show Natural Product (1 entry)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.2.1.3

alpha-aminoadipate semialdehyde + NAD+ + H2O = alpha-aminoadipate + NADH + H+

0

-

Substrate in Enzyme-catalyzed Reactions (8 results)

top print hide

Show Substrate (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

2.6.1.1

2-aminohexanedioic acid + 2-oxoglutarate = 2-oxohexanedioic acid + L-glutamate

639829

-

2.6.1.39

2-aminoadipate + pyruvate = 2-oxoadipate + L-alanine

689965, 639979

-

2.6.1.39

phenylpyruvate + 2-aminoadipate = L-phenylalanine + 2-oxoglutarate

659885, 689965

-

2.6.1.39

2 entries

2.6.1.42

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

639995

-

2.6.1.57

alpha-aminoadipate + 2-oxoglutarate = 2-oxoadipate + L-glutamate

759250, 759287

-

2.6.1.57

alpha-aminoadipate + L-glutamate = 2-oxoglutarate + ?

759250

-

2.6.1.57

2 entries

6.3.2.2

ATP + DL-alpha-aminoadipate + L-cysteine = ADP + phosphate + DL-aminoadipyl-L-cysteine

662339

-

6.3.2.26

alpha-aminoadipic acid + L-valine + L-lysine + ? = L-delta-alpha-aminoadipyl-L-cysteinyl-D-valine + ?

700004

-

Product in Enzyme-catalyzed Reactions (25 results)

top print hide

Show Product (25 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.2.1.3

alpha-aminoadipate semialdehyde + NAD+ + H2O = alpha-aminoadipate + NADH + H+

0

-

1.2.1.3

alpha-aminoadipate semialdehyde + NAD+ + H2O = alpha-aminoadipic acid + NADH + H+

0

-

1.2.1.31

alpha-aminoadipate semialdehyde + NAD+ + H2O = alpha-aminoadipate + NADH + H+

0

-

1.2.1.31

alpha-aminoadipate semialdehyde + NADP+ + H2O = alpha-aminoadipate + NADPH + H+

0

-

1.2.1.31

alpha-aminoadipic semialdehyde + NAD+ + H2O = alpha-aminoadipic acid + NADH + H+

0

-

1.2.1.3

2 entries

1.2.1.31

3 entries

1.2.1.88

2-aminoadipic semialdehyde + NAD+ + H2O = 2-aminoadipate + NADH + H+

0

-

2.6.1.11

N2-acetyl-L-ornithine + 2-oxohexanedioic acid = N-acetyl-L-glutamate 5-semialdehyde + 2-aminohexanedioic acid

0

-

2.6.1.57

2-oxoadipate + L-glutamate = alpha-aminoadipate + 2-oxoglutarate

0

-

2.6.1.7

L-kynurenine + 2-oxoadipate = kynurenic acid + 2-aminoadipate + H2O

636633, 636638, 636625

-

2.6.1.7

L-kynurenine + 2-oxohexanedioate = kynurenic acid + 2-aminohexanedioate + H2O

636608, 636623, 636614

-

2.6.1.74

D-Ala-D-Ala + 2-oxoadipate = ? + 2-aminoadipate

0

-

2.6.1.74

D-alanine + 2-oxoadipate = pyruvate + 2-aminoadipate

0

-

2.6.1.74

D-aspartate + 2-oxoadipate = oxaloacetate + 2-aminoadipate

0

-

2.6.1.74

D-cystine + 2-oxoadipate = ? + 2-aminoadipate

0

-

2.6.1.74

D-glutamate + 2-oxoadipate = 2-oxoglutarate + 2-aminoadipate

0

-

2.6.1.74

D-leucine + 2-oxoadipate = 4-methyl-2-oxopentanoate + 2-aminoadipate

0

-

2.6.1.74

D-methionine + 2-oxoadipate = 4-methylsulfanyl-2-oxobutanoate + 2-aminoadipate

0

-

2.6.1.74

D-serine + 2-oxoadipate = 3-hydroxy-2-oxopropanoate + 2-aminoadipate

0

-

2.6.1.74

D-tryptophan + 2-oxoadipate = 3-indole-2-oxopropanoate + 2-aminoadipate

0

-

2.6.1.74

D-valine + 2-oxoadipate = 3-methyl-2-oxobutanoate + 2-aminoadipate

0

-

2.6.1.7

2 entries

2.6.1.74

10 entries

2.6.1.9

L-histidinol phosphate + 2-oxoadipate = 3-(imidazol-4-yl)-2-oxopropyl phosphate + 2-aminoadipate

0

-

3.5.1.93

cephalosporin C + H2O = (7R)-7-aminocephalosporanate + 2-aminoadipate

0

-

3.5.2.9

2-piperidone-6-carboxylate + ATP + H2O = 2-aminoadipate + phosphate + ADP

0, 209381

-

7.4.2.1

ATP + H2O + alpha-aminoadipic acid-[polar amino acid-binding protein][side 1] = ADP + phosphate + alpha-aminoadipic acid[side 2] + [polar amino acid-binding protein][side 1]

0

-

7.4.2.2

ATP + H2O + alpha-aminoadipic acid-[polar amino acid-binding protein][side 1] = ADP + phosphate + alpha-aminoadipic acid[side 2] + [polar amino acid-binding protein][side 1]

0

-

Inhibitor in Enzyme-catalyzed Reactions (13 results)

top print hide

Show Inhibitors (13 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.2.1.11

-

724553

-

1.2.1.31

-

288195

-

1.2.1.95

inhibitory effect can be reversed by adding methionine

695274

-

1.5.1.9

strong inhibition at 5 mM

392370

-

2.3.3.14

-

288192

-

2.6.1.1

IC50: 1.5 mM

675514

-

2.6.1.39

competitive inhibition against kynurenine or 3-hydroxykynurenine

636623

-

2.6.1.7

-

636608, 636623

-

2.6.1.7

strong inhibition of KAT II

636632

-

2.6.1.7

5 mM decreases KAT II activity

703133

-

2.6.1.7

less than 35% inhibition at 5 mM

702779

-

2.6.1.7

4 entries

4.1.1.15

-

3980

-

6.3.2.2

weak

1132

-

3D Structure of Enzyme-Ligand-Complex (PDB) (17 results)

top print hide

Show 3D Structure of Enzyme-Ligand-Complex (PDB) (17 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.2.1.3

4zul, 3D-view

1.2.1.3

6o4f, 3D-view

1.2.1.3

6o4g, 3D-view

1.2.1.3

6o4i, 3D-view

1.2.1.31

4zul, 3D-view

1.2.1.31

6o4f, 3D-view

1.2.1.31

6o4g, 3D-view

1.2.1.31

6o4i, 3D-view

1.2.1.3

4 entries

1.2.1.31

4 entries

1.2.1.38

5ein, 3D-view

1.2.1.8

4zul, 3D-view

1.2.1.8

6o4f, 3D-view

1.2.1.8

6o4g, 3D-view

1.2.1.8

6o4i, 3D-view

1.2.1.8

4 entries

1.21.3.1

7p3l, 3D-view

3.2.1.14

1h0g, 3D-view

3.2.1.14

1w9u, 3D-view

3.2.1.14

1waw, 3D-view

3.2.1.14

3 entries

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (2 results)

top print hide

Show Turnover Number (2 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

2.6.1.57

2.5

-

pH 7.4, 25°C, recombinant enzyme, with cosubstrate L-glutamate

759250

2.6.1.57

13.2

-

pH 7.4, 25°C, recombinant enzyme, with cosubstrate 2-oxoglutarate

759250

2.6.1.57

2 entries

K_M Value (7 results)

top print hide

Show KM Value (7 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.2.1.31

0.2

-

-

288192

1.2.1.31

0.2

-

NAD+

288193

1.2.1.31

0.78

-

-

288185

2.6.1.57

0.016

-

pH and temperature not specified in the publication, with 2-oxoglutarate

759287

2.6.1.57

0.14

-

pH 7.4, 25°C, recombinant enzyme, with cosubstrate L-glutamate

759250

2.6.1.57

3.3

-

pH 7.4, 25°C, recombinant enzyme, with cosubstrate 2-oxoglutarate

759250

2.6.1.57

4.28

-

pH and temperature not specified in the publication

759287

1.2.1.31

3 entries

2.6.1.57

4 entries

K_i Value (1 result)

top print hide

Show KI Value (1 entry)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.3.3.14

5.1

-

-

288192

IC₅₀ Value (1 result)

top print hide

Show IC50 Value (1 entry)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.6.1.1

1.5

-

IC50: 1.5 mM

675514

References & Links

Literature References (29)

top print hide

Show Reference (29 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

1132

15992

gamma-Glutamylcysteine synthetase. Further purification, half of the sites" reactivity, subunits, and specificity

1977

Sekura, R.; Meister, A.

J. Biol. Chem.

252

2599-2605

3980

658037

Purification and some properties of L-glutamate decarboxylase from human brain

1978

Blindermann, J.M.; Maitre, M.; Ossola, L.; Mandel, P.

Eur. J. Biochem.

86

143-152

209381

239948

5-Oxo-L-prolinase (L-pyroglutamate hydrolase) purification and catalytic properties

1975

Van Der Werf, P.; Griffith, O.W.; Meister, A.

J. Biol. Chem.

250

6686-6692

288185

1975789

Inhibition of alpha-aminoadipate-semialdehyde dehydrogenase from Trichosporon adeninovorans by lysine and lysine analogues

1990

Schmidt, H.; Bode, R.; Birnbaum D.

FEMS Microbiol. Lett.

70

41-44

288192

-

Lysine biosynthesis in the yeast Candida maltosa: properties of some enzymes and regulation of the biosynthetic pathway

1985

Schmidt, H.; Bode, R.; Lindner, M.; Birnbaum, D.

J. Basic Microbiol.

25

675-681

288193

4369906

Degradation of O-phosphohydroxylysine in rat liver. Purification and properties of 2-aminoadipic semialdehyde dehydrogenase

1974

Tsai, C.H.; Henderson, L.M.

J. Biol. Chem.

249

5790-5792

288195

4285660

Metabolism of pipecolic acid in a Pseudomonas species. 3. L-alpha-aminoadipate delta-semialdehyde:nicotinamide adenine dinucleotide oxidoreductase

1966

Calvert, A.F.; Rodwell, V.W.

J. Biol. Chem.

241

409-414

392370

9249048

The enzymology of lysine catabolism in rice seeds. Isolation, characterization, and regulatory properties of a lysine 2-oxoglutarate reductase/saccharopine dehydrogenase bifunctional polypeptide

1997

Gaziola, S.A.; Teixeira, C.M.; Lugli, J.; Sodek, L.; Azevedo, R.A.

Eur. J. Biochem.

247

364-371

636608

3037259

Kynurenine-oxoglutarate aminotransferase from rat kidney

1987

Tobes, M.C.

Methods Enzymol.

142

217-224

636614

3003516

L-Kynurenine transaminase from Hansenula schneggii

1985

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

Methods Enzymol.

113

90-95

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

636625

7493966

Cloning and functional expression of a soluble form of kynurenine/alpha-aminoadipate aminotransferase from rat kidney

1995

Buchli, R.; Alberati-Giani, D.; Malherbe, P.; Kohler, C.; Broger, C.; Cesura, A.M.

J. Biol. Chem.

270

29330-29335

636632

9364331

Characterization of rat brain kynurenine aminotransferases I and II

1997

Guidetti, P.; Okuno, E.; Schwarcz, R.

J. Neurosci. Res.

50

457-465

636633

9078543

Kynurenic acid and kynurenine aminotransferase in heart

1997

Baran, H.; Amann, G.; Lubec, B.; Lubec, G.

Pediatr. Res.

41

404-410

636638

12110301

Isolation, characterization, and functional expression of kynurenine aminotransferase cDNA from the yellow fever mosquito, Aedes aegypti(1)

2002

Fang, J.; Han, Q.; Li, J.

Insect Biochem. Mol. Biol.

32

943-950

639829

7426616

Cysteine sulfinate aminotransferase and aspartate aminotransferase isoenzymes of rat brain. Purification, characterization, and further evidence for identity

1980

Recasens, M.; Benezra, R.; Mandel, P.

Biochemistry

19

4583-4589

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

639995

5922965

Leucine aminotransferase. II. Purification and characterization

1966

Taylor, R.T.; Jenkins, W.T.

J. Biol. Chem.

241

4396-4405

659885

15256574

alpha-Aminoadipate aminotransferase from an extremely thermophilic bacterium, Thermus thermophilus

2004

Miyazaki, T.; Miyazaki, J.; Yamane, H.; Nishiyama, M.

Microbiology

150

2327-2334

662339

15642737

Glutathione synthesis in Streptococcus agalactiae. One protein accounts for gamma-glutamylcysteine synthetase and glutathione synthetase activities

2005

Janowiak, B.E.; Griffith, O.W.

J. Biol. Chem.

280

11829-11839

675514

17442055

Mitochondrial aspartate aminotransferase: a third kynurenate-producing enzyme in the mammalian brain

2007

Guidetti, P.; Amori, L.; Sapko, M.T.; Okuno, E.; Schwarcz, R.

J. Neurochem.

102

103-111

689965

18831049

Mechanism for multiple-substrates recognition of alpha-aminoadipate aminotransferase from Thermus thermophilus

2008

Tomita, T.; Miyagawa, T.; Miyazaki, T.; Fushinobu, S.; Kuzuyama, T.; Nishiyama, M.

Proteins

75

348-359

695274

17351909

Cloning, sequencing and characterization of the alpha-aminoadipate reductase gene (LYS2) from Saccharomycopsis fibuligera

2007

Yan, H.; He, P.; Cheng, H.R.; Shen, A.; Jiang, N.

Yeast

24

189-199

700004

19374992

Enzymology of beta-lactam compounds with cephem structure produced by actinomycete

2009

Liras, P.; Demain, A.L.

Methods Enzymol.

458

401-429

702779

18620547

Substrate specificity and structure of human aminoadipate aminotransferase/kynurenine aminotransferase II

2008

Han, Q.; Cai, T.; Tagle, D.A.; Robinson, H.; Li, J.

Biosci. Rep.

28

205-215

703133

19826765

Structure, expression, and function of kynurenine aminotransferases in human and rodent brains

2010

Han, Q.; Cai, T.; Tagle, D.A.; Li, J.

Cell. Mol. Life Sci.

67

353-368

724553

22464683

Molecular docking and enzymatic evaluation to identify selective inhibitors of aspartate semialdehyde dehydrogenase

2012

Luniwal, A.; Wang, L.; Pavlovsky, A.; Erhardt, P.W.; Viola, R.E.

Bioorg. Med. Chem.

20

2950-2956

759250

30547035

Biochemical characterization of Aspergillus fumigatus AroH, a putative aromatic amino acid aminotransferase

2018

Dindo, M.; Costanzi, E.; Pieroni, M.; Costantini, C.; Annunziato, G.; Bruno, A.; Keller, N.P.; Romani, L.; Zelante, T.; Cellini, B.

Front. Mol. Biosci.

5

104

759287

29199101

Versatility of putative aromatic aminotransferases from Candida albicans

2018

Rzad, K.; Milewski, S.; Gabriel, I.

Fungal Genet. Biol.

110

26-37

Links to other databases for 2-aminoadipic acid

top print hide

Show Links (1 entry)

ChEBI

PubChem