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Ligand N-hydroxyaniline

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

2.3.1.118

acetyl-CoA + an N-hydroxyarylamine = CoA + an N-acetoxyarylamine

486156, 487133, 486155

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2.3.1.5

acetyl-CoA + an N-hydroxyarylamine = CoA + an N-acetoxyarylamine

687848

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

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Show Natural Product (2 entries)

EC NUMBER

PROVEN IN VIVO REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.7.1.16

nitrobenzene + 2 NADPH + 2 H+ = N-hydroxyaniline + 2 NADP+ + H2O

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-

1.7.1.16

nitrosobenzene + NADPH + H+ = N-hydroxyaniline + NADP+ + H2O

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-

1.7.1.16

2 entries

Substrate in Enzyme-catalyzed Reactions (7 results)

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Show Substrate (7 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.7.1.10

N-hydroxy-aniline + NADH = aniline + NAD+ + H2O

394443

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1.7.1.10

phenylhydroxylamine + NADH = phenylamine + NAD+ + H2O

394436, 394435

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1.7.1.10

2 entries

2.3.1.118

acetyl-CoA + an N-hydroxyarylamine = CoA + an N-acetoxyarylamine

486156, 487133, 486155

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2.3.1.5

acetyl-CoA + an N-hydroxyarylamine = CoA + an N-acetoxyarylamine

687848

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2.8.2.9

3'-phosphoadenylylsulfate + N-hydroxyaniline = adenosine 3',5'-bisphosphate + ?

644832

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5.4.4.1

(hydroxyamino)benzene = 2-aminophenol

639029, 639027, 639028

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5.4.4.3

hydroxylaminobenzene = 2-aminophenol + 4-aminophenol

648845

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Product in Enzyme-catalyzed Reactions (6 results)

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Show Product (6 entries)

EC NUMBER

REACTION

REACTION DIAGRAM

LITERATURE

ENZYME 3D STRUCTURE

1.11.2.3

aniline + cumene hydroperoxide = N-phenylhydroxylamine + H2O

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-

1.7.1.16

nitrobenzene + 2 NADPH + 2 H+ = N-hydroxyaniline + 2 NADP+ + H2O

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-

1.7.1.16

nitrobenzene + menadione = N-hydroxyaniline + menadiol + H2O

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-

1.7.1.16

nitrosobenzene + NADPH + H+ = N-hydroxyaniline + NADP+ + H2O

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1.7.1.16

nitrobenzene + 2 NADPH + 2 H+ = N-phenylhydroxylamine + 2 NADP+ + H2O

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-

1.7.1.16

4 entries

3.5.1.13

hydroxyacetanilide + H2O = hydroxyaniline + acetate

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-

Inhibitor in Enzyme-catalyzed Reactions (1 result)

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Show Inhibitors (1 entry)

EC NUMBER

COMMENTARY

LITERATURE

ENZYME 3D STRUCTURE

2.8.2.9

causes inhibition under reaction conditions where oxidative degradation occurs, activity rapidly decreases to less than 10% of the initial activity

644832

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Enzyme Kinetic Parameters

K_M Value (2 results)

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Show KM Value (2 entries)

EC NUMBER

KM VALUE [MM]

KM VALUE MAXIMUM [MM]

COMMENTARY

LITERATURE

2.8.2.9

0.23

-

pH 7, 37°C

644832

5.4.4.1

0.15

-

at pH 7.0

639029

References & Links

Literature References (12)

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Show Reference (12 entries)

BRENDA REFERENCE ID

PUBMED ID

TITLE

YEAR

AUTHORS

JOURNAL

VOLUME

PAGES

394435

4147171

Reduced pyridine nucleotide-dependent N-hydroxy amine oxidase and reductase activities of hepatic microsomes

1973

Kadlubar, F.F.; Mckee, E.M.; Ziegler, D.M.

Arch. Biochem. Biophys.

156

46-57

394436

5069709

The reduction of hydroxylamine and some aryl hydroxamates by liver mitochondria from mammals and birds

1972

Bernheim, M.L.C.

Enzymologia

43

167-176

394443

10503898

Detoxification of carcinogenic aromatic and heterocyclic amines by enzymatic reduction of the N-hydroxy derivative

1999

King, R.S.; Teitel, C.H.; Shaddock, J.G.; Casciano, D.A.; Kadlubar, F.F.

Cancer Lett.

143

167-171

486155

3745141

N-Hydroxyarylamine O-acetyltransferase in hamster liver: identity with arylhydroxamic acid N,O-acetyltransferase and arylamine N-acetyltransferase

1986

Saito, K.; Shinohara, A.; Kamataki, T.; Kato, R.

J. Biochem.

99

1689-1697

486156

3890753

Metabolic activation of mutagenic N-hydroxyarylamines by O-acetyltransferase in Salmonella typhimurium TA98

1985

Saito, K.; Shinohara, A.; Kamataki, T.; Kato, R.

Arch. Biochem. Biophys.

239

286-295

487133

3293663

Acetylator genotype and arylamine-induced carcinogenesis

1988

Hein, D.W.

Biochim. Biophys. Acta

948

37-66

639027

-

Production of 2-amino-5-phenoxyphenol from 4-nitrobiphenyl ether using nitrobenzene nitroreductase and hydroxylaminobenzene mutase from Pseudomonas pseudoalcaligenes JS45

2000

Nadeau, L.J.; He, Z.; Spain, J.C.

J. Ind. Microbiol. Biotechnol.

24

301-305

639028

10877793

Sequence analysis and initial characterization of two isozymes of hydroxylaminobenzene mutase from Pseudomonas pseudoalcaligenes JS45

2000

Davis, J.K.; Paoli, G.C.; He, Z.; Nadeau, L.J.; Somerville, C.C.; Spain, J.C.

Appl. Environ. Microbiol.

66

2965-2971

639029

10672020

Characterization of hydroxylaminobenzene mutase from pNBZ139 cloned from Pseudomonas pseudoalcaligenes JS45: a highly associated SDS-stable enzyme catalyzing an intramolecular transfer of hydroxy groups

2000

He, Z.; Nadeau, L.J.; Spain, J.C.

Eur. J. Biochem.

267

1110-1116

644832

9111223

Oxidation-dependent inactivation of aryl sulfotransferase IV by primary N-hydroxy arylamines during in vitro assays

1997

King, R.S.; Duffel, M.W.

Carcinogenesis

18

843-849

648845

10049374

3-Hydroxylaminophenol mutase from Ralstonia eutropha JMP134 catalyzes a Bamberger rearrangement

1999

Schenzle, A.; Lenke, H.; Spain, J.C.; Knackmuss, H.J.

J. Bacteriol.

181

1444-1450

687848

17368397

Bacillus cereus strain 10-L-2 produces two arylamine N-acetyltransferases that transform 4-phenylenediamine into 4-aminoacetanilide

2007

Mulyono, R.; Takenaka, S.; Sasano, Y.; Murakami, S.; Aoki, K.

J. Biosci. Bioeng.

103

147-154

Links to other databases for N-hydroxyaniline

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Show Links (1 entry)

ChEBI

PubChem

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