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Ligand (E)-indol-3-ylacetaldehyde oxime

Basic Ligand Information

Molecular Structure

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Roles as Enzyme Ligand

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

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Show Natural Substrate (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.45

(E)-indol-3-ylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2 = S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O

741195

-

1.14.14.45

indole-3-acetaldoxime + [reduced NADPH-hemoprotein reductase] + O2 = 1-aci-nitro-2-indolyl-ethane + [oxidized NADPH-hemoprotein reductase] + 2 H2O

741148

-

1.14.14.45

2 entries

Substrate in Enzyme-catalyzed Reactions (8 results)

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Show Substrate (8 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.43

indole-3-acetaldoxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase] = 1-aci-nitro-2-indolyl-ethane + H2O + [oxidized NADPH-hemoprotein reductase]

741196, 741195

-

1.14.14.44

indole-3-acetaldoxime + [reduced NADPH-hemoprotein reductase] + O2 = hydroxy(1H-indol-3-yl)acetonitrile + [oxidized NADPH-hemoprotein reductase] + 2 H2O

741183

-

1.14.14.45

(E)-indol-3-ylacetaldehyde oxime + [reduced NADPH-hemoprotein reductase] + glutathione + O2 = S-[(E)-N-hydroxy(indol-3-yl)acetimidoyl]-L-glutathione + [oxidized NADPH-hemoprotein reductase] + 2 H2O

741195, 741196

-

1.14.14.45

indole-3-acetaldoxime + O2 + glutathione + [reduced NADPH-hemoprotein reductase] = 1-aci-nitro-2-indolyl-ethane + H2O + [oxidized NADPH-hemoprotein reductase]

743440, 743483

-

1.14.14.45

indole-3-acetaldoxime + [reduced NADPH-hemoprotein reductase] + O2 = 1-aci-nitro-2-indolyl-ethane + [oxidized NADPH-hemoprotein reductase] + 2 H2O

741148

-

4.8.1.3

(E,Z)-indolyl-3-acetaldoxime = (E,Z)-indolyl-3-acetonitrile

716456

-

4.8.1.3

3-Indoleacetaldoxime = 3-Indoleacetonitrile

648795, 648794, 648796, 648797

-

1.14.14.45

3 entries

4.8.1.3

2 entries

4.8.1.4

(E/Z)-indole-3-acetaldoxime = indole-3-acetonitrile + H2O

747946

-

Product in Enzyme-catalyzed Reactions (1 result)

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Show Product (1 entry)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.14.14.156

L-tryptophan + 2 [reduced NADPH-hemoprotein reductase] + 2 O2 = (E)-indol-3-ylacetaldoxime + 2 [oxidized NADPH-hemoprotein reductase] + CO2 + 3 H2O

0

-

Enzyme Kinetic Parameters

k_cat Value (Turnover Number) (7 results)

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Show Turnover Number (7 entries)

EC NUMBER

TURNOVER NUMBER [1/S]

TURNOVER NUMBER MAXIMUM [1/S]

COMMENTARY

LITERATURE

1.14.14.43

2.33

-

pH 8.1, 29°C

741196

1.14.14.44

0.028

-

pH 7.6, 30°C

741183

1.14.14.45

0.43

-

pH 8.1, 29°C

741195

1.14.14.45

0.87

-

pH 8.1, 29°C

741196

1.14.14.45

0.88

-

pH 7.6, 28°C

741148

1.14.14.45

53

-

pH 7.6, 28°C

743440

1.14.14.45

4 entries

4.8.1.3

10

-

in 25 mM Tris-HCl buffer pH 7.5, at 23°C

716456

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

1.14.14.43

0.15

-

pH 8.1, 29°C

741196

1.14.14.43

0.15

-

pH not specified in the publication, temperature not specified in the publication

741195

1.14.14.43

2 entries

1.14.14.44

0.0082

-

pH 7.6, 30°C

741183

1.14.14.45

0.003

-

pH 7.6, 28°C

741148, 743440

1.14.14.45

0.0031

-

pH 8.1, 29°C

741195, 741196

4.8.1.3

0.17

-

-

648796

4.8.1.3

0.29

-

in 25 mM Tris-HCl buffer pH 7.5, at 23°C

716456

1.14.14.45

2 entries

4.8.1.3

2 entries

References & Links

Literature References (12)

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Show Reference (12 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

648794

14099566

3-Indoleacetaldoxime hydro-lyase: a pyridoxal-5'-phosphate activated enzyme

1963

Kumar, S.A.; Mahadevan, S.

Arch. Biochem. Biophys.

103

516-518

648795

-

Conversion of 3-indoleacetaldoxime to 3-indoleacetonitrile by plants

1963

Mahadevan, S.

Arch. Biochem. Biophys.

100

557-558

648796

5671050

Indoleacetaldoxime hydro-lyase. II. Purification and properties

1968

Shulka, P.S.; Mahadevan, S.

Arch. Biochem. Biophys.

125

873-883

648797

5435053

Indoleacetaldoxime hydro-lyase (4.2.1.29). III. Further studies on the nature and mode of action of the enzyme

1970

Shulka, P.S.; Mahadevan, S.

Arch. Biochem. Biophys.

137

166-174

716456

21036375

Indolyl-3-acetaldoxime dehydratase from the phytopathogenic fungus Sclerotinia sclerotiorum: purification, characterization, and substrate specificity

2010

Pedras, M.S.; Minic, Z.; Thongbam, P.D.; Bhaskar, V.; Montaut, S.

Phytochemistry

71

1952-1962

741148

11158532

CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis

2001

Bak, S.; Tax, F.E.; Feldmann, K.A.; Galbraith, D.W.; Feyereisen, R.

Plant Cell

13

101-111

741183

25015725

Identification and characterization of CYP79D16 and CYP71AN24 catalyzing the first and second steps in L-phenylalanine-derived cyanogenic glycoside biosynthesis in the Japanese apricot, Prunus mume Sieb. et Zucc

2014

Yamaguchi, T.; Yamamoto, K.; Asano, Y.

Plant Mol. Biol.

86

215-223

741195

11553739

The involvement of two p450 enzymes, CYP83B1 and CYP83A1, in auxin homeostasis and glucosinolate biosynthesis

2001

Bak, S.; Feyereisen, R.

Plant Physiol.

127

108-118

741196

12970475

CYP83A1 and CYP83B1, two nonredundant cytochrome P450 enzymes metabolizing oximes in the biosynthesis of glucosinolates in Arabidopsis

2003

Naur, P.; Petersen, B.L.; Mikkelsen, M.D.; Bak, S.; Rasmussen, H.; Olsen, C.E.; Halkier, B.A.

Plant Physiol.

133

63-72

743440

11158532

CYP83B1, a cytochrome P450 at the metabolic branch point in auxin and indole glucosinolate biosynthesis in Arabidopsis

2001

Bak, S.; Tax, F.; Feldmann, K.; Galbraith, D.; Feyereisen, R.

Plant Cell

13

101-111

743483

11553739

The involvement of two p450 enzymes, CYP83B1 and CYP83A1, in auxin homeostasis and glucosinolate biosynthesis

2001

Bak, S.; Feyereisen, R.

Plant Physiol.

127

108-118

747946

29698761

Overproduction and characterization of the first enzyme of a new aldoxime dehydratase family in Bradyrhizobium sp.

2018

Raedisch, R.; Chmatal, M.; Rucka, L.; Novotny, P.; Petraskova, L.; Halada, P.; Kotik, M.; Patek, M.; Martinkova, L.

Int. J. Biol. Macromol.

115

746-753

Links to other databases for (E)-indol-3-ylacetaldehyde oxime

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ChEBI

PubChem