1.7.1.16: nitrobenzene nitroreductase
This is an abbreviated version!
For detailed information about nitrobenzene nitroreductase, go to the full flat file.
Word Map on EC 1.7.1.16
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1.7.1.16
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pseudoalcaligenes
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flavin
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hydroxylaminobenzene
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microbiol
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nitrofurazone
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fmn
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putida
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silica
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mutase
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two-electron
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analysis
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mononucleotide
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degradation
- 1.7.1.16
- pseudoalcaligenes
- flavin
- hydroxylaminobenzene
-
microbiol
- nitrofurazone
- fmn
- putida
- silica
- mutase
-
two-electron
- analysis
- mononucleotide
- degradation
Reaction
+ 2 NADP+ + = + 2 NADPH + 2 H+
Synonyms
cnbA, NbzA, NfsB, NTR, Oxygen-insensitive NAD(P)H nitroreductase
ECTree
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Substrates Products
Substrates Products on EC 1.7.1.16 - nitrobenzene nitroreductase
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REACTION DIAGRAM
(2E)-2-[(5-nitrofuran-2-yl)methylidene]hydrazine-1-carboxamide + 2 NADPH + 2 H+
(2E)-2-[[5-(hydroxyamino)furan-2-yl]methylidene]hydrazine-1-carboxamide + 2 NADP+
1,3-dinitrobenzene + 2 NADPH + 2 H+
1-amino-3-nitrobenzene + 2 NADP+ + H2O
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about 90% 1-amino-3-nitrobenzene plus 10% 1-hydroxylamino-3-nitrobenzene
-
?
1-hydroxylamino-3-nitrobenzene + 2 NADPH + 2 H+
1-amino-3-nitrobenzene + 2 NADP+ + H2O
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-
-
-
?
1-nitroso-3-nitrobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
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-
only the amino product can be observed
-
?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
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-
products are hydroxylamino- and amino-dinitrotoluene isomersd
-
?
2,4-dichloro-1-nitrobenzene + 2 NADPH + 2 H+
2,4-dichloro-N-hydroxyaniline + 2 NADP+ + H2O
-
-
-
-
?
2-chloro-6-nitrotoluene + 3 NADPH + 3 H+
3-chloro-2-methylaniline + 3 NADP+ + 2 H2O
Psychrobacter sp. ANT206
-
-
-
-
?
3-bromo-4-nitrotoluene + 3 NADPH + 3 H+
2-bromo-4-methylaniline + 3 NADP+ + 2 H2O
Psychrobacter sp. ANT206
-
-
-
-
?
3-nitrophenol + 2 NADPH + 2 H+
3-(hydroxyamino)phenol + 2 NADP+ + H2O
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recombinant protein, 66% of the activity with 4-chloronitrobenzene
-
?
4-chloronitrobenzene + 2 NADH + 2 H+
4-chloro-N-hydroxyaniline + 2 NAD+ + H2O
-
-
-
?
4-chloronitrobenzene + 2 NADPH + 2 H+
2-amino-5-chlorophenol + 2 NADP+ + H2O
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reaction in presence of hydroxylaminobenzene mutase CnbB
-
?
4-nitrochlorobenzene + 3 NADPH + 3 H+
4-chloroaniline + 3 NADP+ + 2 H2O
Psychrobacter sp. ANT206
-
-
-
-
?
4-nitrotoluene + 2 NADPH + 2 H+
N-hydroxy-4-methylaniline + 2 NADP+ + H2O
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + 2 NADPH + 2 H+
? + 2 NADP+
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enzyme activates the dinitrobenzamide cancer prodrug CB1954, i.e. 5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
?
nitrobenzene + 2 NADPH + 2 H+
aniline + 2 NADP+ + H2O
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reduction of nitrobenzene to aniline occurs through the formation of nitrosobenzene and phenylhydroxylamine as intermediates. More than 99% overall conversion
-
?
nitrobenzene + 3 NADH + 3 H+
aniline + 3 NAD+ + 2 H2O
Psychrobacter sp. ANT206
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30% activity compared to 3 NADPH
-
-
?
[2-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-5-[(2-nitrophenyl)sulfanyl]-1H-pyrrolato-kappaN](difluorido)boron + 2 NADH + 2 H+
[2-([5-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-1H-pyrrol-2-yl-kappaN]sulfanyl)anilinato](difluorido)boron + 2 NAD+ + H2O
[2-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-5-[(3-nitrophenyl)sulfanyl]-1H-pyrrolato-kappaN](difluorido)boron + 2 NADH + 2 H+
?
[2-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-5-[(4-nitrophenyl)sulfanyl]-1H-pyrrolatokappa?N](difluorido)boron + 2 NADH + 2 H+
?
(2E)-2-[[5-(hydroxyamino)furan-2-yl]methylidene]hydrazine-1-carboxamide + 2 NADP+
i.e. anti-infective furacilin
-
-
?
(2E)-2-[(5-nitrofuran-2-yl)methylidene]hydrazine-1-carboxamide + 2 NADPH + 2 H+
(2E)-2-[[5-(hydroxyamino)furan-2-yl]methylidene]hydrazine-1-carboxamide + 2 NADP+
i.e. anti-infective furacilin
-
-
?
? + 2 NADP+ + H2O
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-
-
-
?
2,4-dinitrochlorobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
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recombinant protein, 43% of the activity with 4-chloronitrobenzene
-
?
2,4-dinitrochlorobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
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recombinant protein, 43% of the activity with 4-chloronitrobenzene
-
?
? + 2 NADP+ + H2O
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most abundant products are amino-nitrotoluene isomers, plus some hydroxylamino and diaminotoluene isomers
-
?
2,4-dinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
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recombinant protein, 98% of the activity with 4-chloronitrobenzene
-
?
2,4-dinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
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recombinant protein, 98% of the activity with 4-chloronitrobenzene
-
?
2-chloro-N-hydroxyaniline + 2 NADP+ + H2O
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-
-
?
2-chloronitrobenzene + 2 NADPH + 2 H+
2-chloro-N-hydroxyaniline + 2 NADP+ + H2O
-
-
-
?
2-chloronitrobenzene + 2 NADPH + 2 H+
2-chloro-N-hydroxyaniline + 2 NADP+ + H2O
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recombinant protein, 17% of the activity with 4-chloronitrobenzene
-
?
2-chloronitrobenzene + 2 NADPH + 2 H+
2-chloro-N-hydroxyaniline + 2 NADP+ + H2O
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recombinant protein, 17% of the activity with 4-chloronitrobenzene
-
?
3-chloro-N-hydroxyaniline + 2 NADP+ + H2O
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recombinant protein, 84% of the activity with 4-chloronitrobenzene
-
?
3-chloronitrobenzene + 2 NADPH + 2 H+
3-chloro-N-hydroxyaniline + 2 NADP+ + H2O
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recombinant protein, 84% of the activity with 4-chloronitrobenzene
-
?
N-hydroxy-3-methylaniline + 2 NADP+ + H2O
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-
-
?
3-nitrotoluene + 2 NADPH + 2 H+
N-hydroxy-3-methylaniline + 2 NADP+ + H2O
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-
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?
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
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?
4-chloronitrobenzene + 2 NADPH + 2 H+
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
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-
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?
4-chloronitrobenzene + 2 NADPH + 2 H+
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
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-
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?
4-chloronitrobenzene + 2 NADPH + 2 H+
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
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2.2 mol of NADPH is oxidized per mol of 4-chloronitrobenzene
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?
4-nitrophenol + 3 NADPH + 3 H+
4-aminophenol + 3 NADP+ + 2 H2O
Psychrobacter sp. ANT206
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the enzyme can degrade 4-nitrophenol in low temperature environment
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-
?
? + 2 NADP+ + H2O
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enzyme activates the dinitrobenzamide cancer prodrug CB1954, i.e. 5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
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enzyme activates the dinitrobenzamide cancer prodrug CB1954, i.e. 5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
?
N-hydroxyaniline + 2 NADP+ + H2O
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-
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?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
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-
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
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-
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?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
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N-hydroxyaniline is the only product detected
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
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-
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?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
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N-hydroxyaniline is the only product detected
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?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
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recombinant protein, 61% of the activity with 4-chloronitrobenzene
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
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recombinant protein, 61% of the activity with 4-chloronitrobenzene
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?
N-phenylhydroxylamine + 2 NADP+ + H2O
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overall reaction
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?
nitrobenzene + 2 NADPH + 2 H+
N-phenylhydroxylamine + 2 NADP+ + H2O
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-
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?
nitrobenzene + 2 NADPH + 2 H+
N-phenylhydroxylamine + 2 NADP+ + H2O
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overall reaction
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?
nitrobenzene + 3 NADPH + 3 H+
aniline + 3 NADP+ + 2 H2O
Psychrobacter sp. ANT206
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100% activity with 3 NADPH
-
-
?
nitrobenzene + 3 NADPH + 3 H+
aniline + 3 NADP+ + 2 H2O
Psychrobacter sp. ANT206
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the enzyme can degrade 4-nitrophenol in low temperature environment
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-
?
N-hydroxyaniline + menadiol + H2O
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?
nitrobenzene + menadione
N-hydroxyaniline + menadiol + H2O
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?
? + 2 NADP+ + H2O
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enzyme activates the proantibiotic nitrofurazone
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?
nitrofurazone + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
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enzyme activates the proantibiotic nitrofurazone
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?
nitrofurazone + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
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-
-
?
N-hydroxyaniline + NADP+ + H2O
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nitrosobenzene is not detected as an intermediate of nitrobenzene reduction, but nitrosobenzene is a substrate for the enzyme
-
?
nitrosobenzene + NADPH + H+
N-hydroxyaniline + NADP+ + H2O
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nitrosobenzene is not detected as an intermediate of nitrobenzene reduction, but nitrosobenzene is a substrate for the enzyme
-
?
[2-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-5-[(2-nitrophenyl)sulfanyl]-1H-pyrrolato-kappaN](difluorido)boron + 2 NADH + 2 H+
[2-([5-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-1H-pyrrol-2-yl-kappaN]sulfanyl)anilinato](difluorido)boron + 2 NAD+ + H2O
-
-
-
?
[2-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-5-[(2-nitrophenyl)sulfanyl]-1H-pyrrolato-kappaN](difluorido)boron + 2 NADH + 2 H+
[2-([5-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-1H-pyrrol-2-yl-kappaN]sulfanyl)anilinato](difluorido)boron + 2 NAD+ + H2O
-
-
-
?
[2-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-5-[(3-nitrophenyl)sulfanyl]-1H-pyrrolato-kappaN](difluorido)boron + 2 NADH + 2 H+
?
-
-
-
?
[2-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-5-[(3-nitrophenyl)sulfanyl]-1H-pyrrolato-kappaN](difluorido)boron + 2 NADH + 2 H+
?
-
-
-
?
[2-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-5-[(4-nitrophenyl)sulfanyl]-1H-pyrrolatokappa?N](difluorido)boron + 2 NADH + 2 H+
?
-
-
-
?
[2-[(4-ethyl-3,5-dimethyl-2H-pyrrol-2-ylidene-?N)(phenyl)methyl]-5-[(4-nitrophenyl)sulfanyl]-1H-pyrrolatokappa?N](difluorido)boron + 2 NADH + 2 H+
?
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-
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?
?
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1.8 mol of NADPH is oxidized per mol of nitrobenzene converted to product
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?
additional information
?
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1.8 mol of NADPH is oxidized per mol of nitrobenzene converted to product
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?
additional information
?
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enzyme additionally catalyzes reduction of 2,4,6-trinitrotoluene
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?
additional information
?
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enzyme shows broad substrate acceptance for various nitro compounds such as 1-nitrocyclohexene and aliphatic nitroalkenes (alkene reductase activity), as well as nitrobenzene (nitroreductase activity), with substrate conversion efficiency of >95%
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-
?