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Ligand Aminooxyacetate

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (1 result)

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Show Substrate (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

6.3.2.3

ATP + gamma-Glu-L-Cys + aminooxyacetate = ADP + phosphate + gamma-Glu-Cys-aminoxyacetate

1194

-

Activator in Enzyme-catalyzed Reactions (5 results)

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Show Activating Compound (5 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.6.1.44

for some enzyme mutants, sensitivity to trypsin can be ameliorated by addition of pyridoxal 5'-phosphate or aminooxyacetic acid

689026

1H0C, 3D-view

2.6.1.44

for some enzyme mutants, sensitivity to trypsin can be ameliorated by addition of pyridoxal 5'-phosphate or aminooxyacetic acid

689026

1J04, 3D-view

2.6.1.44

presence significantly stabilizes enzyme

687769

1H0C, 3D-view

2.6.1.44

presence significantly stabilizes enzyme

687769

1J04, 3D-view

2.6.1.44

4 entries

4.1.1.15

-

3989

-

Inhibitor in Enzyme-catalyzed Reactions (119 results)

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Show Inhibitors (119 entries)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

1.1.99.14

competitive to glycolate and glyoxylate

348288

-

1.4.1.3

5 mM, weak inhibition of isozymes 1-3

391622

-

1.4.3.1

-

742035

-

1.4.3.1

66.4% residual activity at 1 mM

742035

-

1.4.3.1

2 entries

1.4.4.2

-

655343

1WYV, 3D-view

1.7.1.1

-

392862

-

2.1.2.1

strong

441391

-

2.3.1.183

-

671406

-

2.3.1.29

-

486740

-

2.3.2.2

hydrolase reaction

487946

-

2.5.1.47

10 mM, 76% inhibition

706226

-

2.5.1.47

57% and 64% inhibition at 1 mM, isoenzymes 1 and 2, respectively

637360

-

2.5.1.47

2 entries

2.5.1.48

-

637448

-

2.6.1.113

-

739832

-

2.6.1.13

-

637137

-

2.6.1.13

almost complete inhibition at 0.2 mM

637137

-

2.6.1.13

fully reversed by addition of pyridoxal phosphate

637121

-

2.6.1.13

3 entries

2.6.1.14

-

637254

-

2.6.1.15

soluble fraction

639897

-

2.6.1.18

strong inhibition

657597

-

2.6.1.19

-

637032, 637034, 637056, 637059, 661084, 661189, 723611

-

2.6.1.19

80% inhibition at 2 mM

637079

-

2.6.1.19

99% inhibition at 1 mM

637043

-

2.6.1.19

kinetics

637041

-

2.6.1.2

0.0004 mM, 85% inhibition of mitochondrial alanine aminotransferase

636721

-

2.6.1.2

1 mM, 98% inhibition

636726

-

2.6.1.2

1 mM, complete inhibition

636723

-

2.6.1.2

2 mM, complete inhibition

636724

-

2.6.1.2

competitive to L-alanine, uncompetitive to 2-oxoglutarate

661515

-

2.6.1.2

complete inhibition, both isoforms

662840

-

2.6.1.2

2.5 mM, complete inhibition

672286

-

2.6.1.21

0.0001 mM, 50% inhibition

636737

-

2.6.1.21

0.01 mM, 90% inhibition

636742

-

2.6.1.19

4 entries

2.6.1.2

7 entries

2.6.1.21

2 entries

2.6.1.27

-

738172

-

2.6.1.33

complete inhibition by a mixture of hydroxylamine, (aminooxy)acetic acid, and gabaculine as inhibitors specific for pyridoxal 5'-phosphate-dependent enzymes

658427

-

2.6.1.37

1 mM, 100% inhibition

636706

-

2.6.1.4

-

636731

-

2.6.1.40

strong

644426

-

2.6.1.42

-

640019

-

2.6.1.42

residual activity 79%

738188

-

2.6.1.42

-

722998

-

2.6.1.42

1 mM, 20% residual activity

661957

-

2.6.1.42

mixed-type inhibition, acts also as growth inhibitor of organism

661400

-

2.6.1.42

5 entries

2.6.1.43

-

640045, 640048, 640050

-

2.6.1.44

-

640071, 640076, 640087

1H0C, 3D-view

2.6.1.44

-

640071, 640076, 640087

1J04, 3D-view

2.6.1.44

competitive inhibitor

640088

1H0C, 3D-view

2.6.1.44

competitive inhibitor

640088

1J04, 3D-view

2.6.1.44

-

701547

1H0C, 3D-view

2.6.1.44

-

701547

1J04, 3D-view

2.6.1.45

1 mM, complete inhibition

636689

-

2.6.1.45

competitive inhibition

636694

-

2.6.1.45

reacts with the carbonyl group of pyridoxal phosphate, 88% inhibition at 0.01 mM

684122

-

2.6.1.5

-

721359

-

2.6.1.5

1 mM, complete inhibition

657704

-

2.6.1.5

probably acts reacting with the cofactor

640113

-

2.6.1.44

6 entries

2.6.1.45

3 entries

2.6.1.5

3 entries

2.6.1.52

AOA, the transaminase inhibitor represses cell growth in a TAZ/YAP-dependent manner

759123

-

2.6.1.57

-

636654

-

2.6.1.59

-

658427

-

2.6.1.64

-

640183

-

2.6.1.64

AOA, the transaminase inhibitor represses cell growth in a TAZ/YAP-dependent manner

759123

-

2.6.1.7

-

760098

-

2.6.1.7

inhibitory in whole cells

660010

-

2.6.1.64

2 entries

2.6.1.7

2 entries

2.6.1.72

-

636992

-

2.6.1.75

1 mM, complete inhibition of the three isoenzymes

640196

-

2.6.1.88

complete inhibition at 1 mM

715336

-

2.6.1.88

mixed-type inhibition, about 7% residual activity at 1 mM

661400

-

2.6.1.96

effective inhibition at 250 microM

723611

-

2.6.1.96

80% inhibition at 2 mM

637079

-

2.6.1.88

2 entries

2.6.1.96

2 entries

2.7.1.35

0.002 mM, 50% inhibition

641404

-

3.5.4.4

-

209609

-

3.5.99.7

0.005-1 mM, enzymatic activity is progressively inhibited as the aminooxyacetic acid concentration is increased

694780

-

4.1.1.12

-

3961

-

4.1.1.15

-

3971

-

4.1.1.15

-

727569

-

4.1.1.15

after application (5 mM) for 4 days during germination, the GAD activity in germinating fava beans is inhibited by more than 90%. The GABA contents decrease by 43.9% and 81.5% in a 4 day-old cotyledon and embryo under hypoxia-NaCl stress

775749

-

4.1.1.15

-

727626

-

4.1.1.15

4 entries

4.1.1.20

-

4112

-

4.1.1.28

-

4218

-

4.1.1.86

PLP-dependent inhibitor, 42% inhibition at 0.5 mM, 65% inhibition at 1 mM

661801

-

4.1.1.86

PLP-dependent inhibitor, 42% inhibition at 0.5 mM, 78% inhibition at 1 mM

661472

-

4.2.1.22

complete inhibition at 0.05 mM

701750

-

4.2.1.22

-

5584, 5597

-

4.2.1.22

inhibitor binds CBS tighter than its respective substrates and forms a dead-end PLP-bound intermediate featuring an oxime bond. Serine, but not cysteine, replaces aminooxyacetic acid from CBS and forms an aminoacrylate reaction intermediate, which allows for the continuation of the catalytic cycle. Treatment with aminooxyacetic acid decreases H2S production and bioenergetics, while additional serine rescues CBS activity, H2S production and mitochondrial function

770220

-

4.1.1.86

2 entries

4.2.1.22

3 entries

4.3.1.18

-

680567

-

4.3.1.24

-

34364

-

4.3.1.24

-

688652, 705373, 706110

-

4.3.1.24

a reduction in PAL activity is observed in hairy roots, supplemented with 0.5-1 mM aminooxyacetic acid

705364

-

4.3.1.24

irreversible inhibition, treatment results in decrease in content of 2-hydroxy-4-methoxybenzaldehyde

681619

-

4.3.1.24

4 entries

4.3.1.25

-

34339

-

4.4.1.1

-

34494

-

4.4.1.1

-

729511

-

4.4.1.1

chronical treatment of rats with CGL inhibitor (DL)-propargylglycine or cystathionine beta-synthase inhibitor aminooxyacetic acid or a combination of both. Only the rats with combination therapy show a decrease in urinary sulfate excretion rate, which is associated with an increase in mean arterial pressure. Urine flow and sodium excretion are also increased in combination group as consequent to the increase in mean arterial pressure. Glomerular filtration rate does not alter due to these treatments, renal blood flow is lowered only in the combination group compared to the control group

713713

-

4.4.1.1

-

34509

-

4.4.1.13

-

34557, 34558, 34559, 34563, 672202

-

4.4.1.13

mitochondrial enzyme more sensitive than cytosolic

34545

-

4.4.1.13

irreversible

34689

-

4.4.1.14

-

34567, 34572, 34577, 34578, 694633

-

4.4.1.14

competitive inhibition with respect to S-adenosyl-L-methionine

768881

-

4.4.1.15

at 10 microM, IC50 value is 0.0305 mM

664881

-

4.4.1.15

-

648734, 648737

-

4.4.1.15

0.005-1 mM, enzymatic activity is progressively inhibited as the aminooxyacetic acid concentration is increased

694780

-

4.4.1.1

4 entries

4.4.1.13

3 entries

4.4.1.14

2 entries

4.4.1.15

3 entries

4.4.1.35

0.5 mM, 2% residual activity; 0.5 mM, complete inhibition

741128

-

4.4.1.4

-

34610

-

4.4.1.9

-

34721, 34723

-

5.1.1.1

1 mM, complete inhibition, both directions

655267

-

5.1.1.1

-

673766

-

5.1.1.1

1 mM, complete inhibition

650876

-

5.1.1.1

3 entries

5.1.1.10

complete inhibition at 0.002 mM

715591

-

5.1.1.13

complete inhibition

650892

-

5.1.1.13

-

706558

-

5.1.1.18

-

663264

-

5.1.1.18

complete inhibition

663263

-

5.1.1.18

non-selective inhibitor

714348

-

5.4.3.8

-

3436

-

5.4.3.8

20 mM, 57% inhibition

3419

-

5.1.1.13

2 entries

5.1.1.18

3 entries

5.4.3.8

2 entries

6.3.2.11

-

989

-

7.2.2.7

the addition of ethylene inhibitors decreases AtIRT1 expression, ethylene could be involved in the regulation of AtIRT1 transcription

688070

-

7.2.2.7

the addition of ethylene inhibitors decreases LeIRT1 expression, ethylene could be involved in the regulation of LeIRT1 transcription

688070

-

7.2.2.7

2 entries

3D Structure of Enzyme-Ligand-Complex (PDB) (53 results)

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Show 3D Structure of Enzyme-Ligand-Complex (PDB) (53 entries)

EC NUMBER

ENZYME 3D STRUCTURE

1.4.4.2

1WYV, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.44

1H0C, 3D-view

2.6.1.44

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.51

1H0C, 3D-view

2.6.1.51

1J04, 3D-view

2.6.1.44

26 entries

2.6.1.51

26 entries

Enzyme Kinetic Parameters

K_i Value (17 results)

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Show KI Value (17 entries)

EC NUMBER

KI VALUE [MM]

KI VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

1.1.99.14

1.2

-

-

348288

1.4.3.1

1.416

-

at pH 8.3 and 37°C

742035

1.4.3.1

1.492

-

at pH 8.3 and 37°C

742035

1.4.3.1

1.915

-

at pH 8.3 and 37°C

742035

1.4.3.1

3 entries

2.1.2.1

0.014

-

-

441391

2.6.1.19

0.24

-

-

661189

2.6.1.19

0.62

-

wild-type, pH 7.8, 25°C

661189

2.6.1.19

1.13

-

mutant V241A, pH 7.8, 25°C

661189

2.6.1.2

0.00034

-

pH 7.4, 25°C

661515

2.6.1.2

0.00064

-

pH 7.4, 25°C

661515

2.6.1.42

0.01424

-

uncompetitive component of mixed-type inhibition, pH 7.4, 37°C

661400

2.6.1.42

0.0209

-

competitive component of mixed-type inhibition, pH 7.4, 37°C

661400

2.6.1.19

3 entries

2.6.1.2

2 entries

2.6.1.42

2 entries

2.6.1.45

0.00012

-

-

636694

2.6.1.88

0.02097

-

competitive inhibition, at pH 7.4, 37°C

661400

2.6.1.88

0.1424

-

uncompetitive inhibition, at pH 7.4, 37°C

661400

2.6.1.88

2 entries

4.4.1.14

0.0008

-

at pH 8.5 and 30°C

768881

4.4.1.15

0.0033

-

value bases on non-linear regression

694780

IC₅₀ Value (7 results)

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Show IC50 Value (7 entries)

EC NUMBER

IC50 VALUE

IC50 VALUE MAXIMUM

COMMENTARY

LITERATURE

2.6.1.27

0.8

-

pH 8.0, 42°C

738172

2.6.1.7

0.0131

-

at pH 8.0 and 45°C

760098

4.1.1.15

0.0004

-

pH 8.0, 37°C, recombinant enzyme

727626

4.1.1.15

0.0005

-

pH 8.0, 37°C, recombinant enzyme

727626

4.1.1.15

0.001

-

pH 8.0, 37°C, recombinant enzyme

727626

4.1.1.15

3 entries

4.4.1.1

0.0011

-

pH 8.2, 37°C

729511

4.4.1.15

0.0305

-

at 10 microM, IC50 value is 0.0305 mM

664881

References & Links

Literature References (137)

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Show Reference (137 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

989

6808276

Carnosine-synthetase inhibition by beta-alanine analogues

1982

Seely, J.E.; Marshall, F.D.

Life Sci.

30

1763-1768

1194

447639

Glutathione synthetase. Purification from rat kidney and mapping of the substrate binding sites

1979

Oppenheimer, L.; Wellner, V.P.; Griffith, O.W.; Meister.A.

J. Biol. Chem.

254

5184-5190

3419

-

Biosynthesis of DELTA-aminolevulinate in greening barley leaves: glutamate 1-semialdehyde aminotransferase

1978

Kannangara, C.G.; Gough, S.P.

Carlsberg Res. Commun.

43

185-194

3436

1985889

Purification and functional characterization of glutamate-1-semialdehyde aminotransferase from Chlamydomonas reinhardtii

1991

Jahn, D.; Chen, M.W.; Söll, D.

J. Biol. Chem.

266

161-167

3961

20492933

Rat brain aspartate beta-decarboxylase. A comparative study with the liver enzyme

1985

Wong, P.T.H.

Neurochem. Int.

7

351-355

3971

3468504

Brain L-glutamate decarboxylase: purification and subunit structure

1987

Denner, L.A.; Wei, S.C.; Lin, H.S.; Lin, C.T.; Wu, J.Y.

Proc. Natl. Acad. Sci. USA

84

668-672

3989

8125937

Purification and characterization of a novel form of brain L-glutamate decarboxylase. A Ca2+-dependent peripheral membrane protein

1994

Nathan, B.; Hsu, C.C.; Bao, J.; Wu, R.; Wu, J.Y.

J. Biol. Chem.

269

7249-7254

4112

1269753

A chloroplast-localized diaminopimelate decarboxylase in higher plants

1976

Mazelis, M.N.; Miflin, B.J.; Prati, H.M.

FEBS Lett.

64

197-200

4218

3600369

Aromatic-L-amino acid decarboxylase from pig kidney

1987

Voltattorni, C.B.; Giartosio, A.; Turano, C.

Methods Enzymol.

142

179-187

5584

6364702

The beta-replacement-specific pyridoxal-P-dependent lyases

1984

Braunstein, A.E.; Goryachenkova, E.V.

Adv. Enzymol. Relat. Areas Mol. Biol.

56

1-89

5597

1740180

Biochemical characterization of the enzyme responsible for activated L-serine sulphydrase" activity in nematodes

1992

Walker, J.; Barrett, J.

Exp. Parasitol.

74

205-215

34339

-

Purification and properties of phenylalanine ammonia-lyase from sunflower (Helianthus annuus L.) hypocotyls

1988

Jorrin, J.; Lopez-Valbuena, R.; Tena, M.

Biochim. Biophys. Acta

964

73-82

34364

8043606

Phenylalanine ammonia-lyase from cotton (Gossypium hirsutum) hypocotyls: properties of the enzyme induced by a Verticillium dahliae phytotoxin

1994

Dubery, I.A.; Smit, F.

Biochim. Biophys. Acta

1207

24-30

34494

8458

Reactivity of the phosphopyridoxal groups of cystathionase

1976

Beeler, T.; Churchich, J.E.

J. Biol. Chem.

251

5267-5271

34509

16535512

Purification and characterization of cystathionine gamma-lyase from Lactococcus lactis subsp. cremonis SK11: possible role in flavor compound formation during cheese maturation

1997

Bruinenberg, P.G.; de Roo, G.; Limsowtin, G.K.Y.

Appl. Environ. Microbiol.

63

561-566

34545

3700378

Renal cysteine conjugate beta-lyase. Bioactivation of nephrotoxic cysteine S-conjugates in mitochondrial outer membrane

1986

Lash, L.H.; Elfarra, A.A.; Anders, M.W.

J. Biol. Chem.

261

5930-5935

34557

2467759

Inhibition of rat kidney mitochondrial DNA, RNA and protein synthesis by halogenated cysteine S-conjugates

1989

Banki, K.; Anders, M.W.

Carcinogenesis

10

767-772

34558

7814371

Isolation from rat kidney of a cytosolic high molecular weight cysteine-S-conjugate beta-lyase with activity toward leukotriene E4

1995

Abraham, D.G.; Patel, P.P.; Cooper, A.J.L.

J. Biol. Chem.

270

180-188

34559

2568912

Quantitation of multiple pathways for the metabolism of nephrotoxic cysteine conjugates using selective inhibitors of L-alpha-hydroxy acid oxidase (L-amino acid oxidase) and cysteine conjugate beta-lyase

1989

Stevens, J.L.; Hatzinger, P.B.; Hayden, P.J.

Drug Metab. Dispos.

17

297-303

34563

8526486

Bioactivation of cysteine conjugates of 1-nitropyrene oxides by cysteine conjugate beta-lyase purified from Peptostreptococcus magnus

1995

Kataoka, K.; Kinouchi, T.; Akimoto, S.; Ohnishi, Y.

Appl. Environ. Microbiol.

61

3781-3787

34567

-

1-Aminocyclopropane-1-carboxylate synthase

1987

Adams, D.O.; Yang, S.F.

Methods Enzymol.

143

426-429

34572

-

Purification and properties of 1-aminocyclopropane-1-carboxylate synthase of mesocarp of Cucurbita maxima Duch. fruits

1986

Nakajima, N.; Imaseki, H.

Plant Cell Physiol.

27

969-980

34577

507845

1-Aminocyclopropanecarboxylate synthase, a key enzyme in ethylene biosynthesis

1979

Yu, Y.B.; Adams, D.O.; Yang, S.F.

Arch. Biochem. Biophys.

198

280-286

34578

24317737

Assay for an enzymatic formation of an ethylene precursor, 1-aminocyclopropane-1-carboxylic acid

1979

Boller, T.; Herner, R.C.; Kende, H.

Planta

145

293-303

34610

-

The C-S lyases of higher plants. Purification and characterization of homogeneous alliin lyase of leek (Allium porrum)

1989

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Extremophiles

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Rapid purification and characterization of cystine lyase b from broccoli inflorescence

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742035

25747990

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Characterization of the enzymatic and structural properties of human D-aspartate oxidase and comparison with those of the rat and mouse enzymes

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759123

29661856

Glutamine-utilizing transaminases are a metabolic vulnerability of TAZ/YAP-activated cancer cells

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760098

28097769

High resolution crystal structures of human kynurenine aminotransferase-I bound to PLP cofactor, and in complex with aminooxyacetate

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High resolution crystal structures of human kynurenine aminotransferase-I bound to PLP cofactor, and in complex with aminooxyacetate

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742035

2 entries

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2 entries

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Links to other databases for Aminooxyacetate

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