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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

Reaction

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

Synonyms

cnbA, NbzA, NfsB, NTR, Oxygen-insensitive NAD(P)H nitroreductase

ECTree

     1 Oxidoreductases
         1.7 Acting on other nitrogenous compounds as donors
             1.7.1 With NAD+ or NADP+ as acceptor
                1.7.1.16 nitrobenzene nitroreductase

Substrates Products

Substrates Products on EC 1.7.1.16 - nitrobenzene nitroreductase

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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(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+
show the reaction diagram
1,3-dinitrobenzene + 2 NADPH + 2 H+
1-amino-3-nitrobenzene + 2 NADP+ + H2O
show the reaction diagram
-
-
about 90% 1-amino-3-nitrobenzene plus 10% 1-hydroxylamino-3-nitrobenzene
-
?
1,3-dinitrobenzene + 2 NADPH + 2 H+
? + 2 NADP+
show the reaction diagram
1-hydroxylamino-3-nitrobenzene + 2 NADPH + 2 H+
1-amino-3-nitrobenzene + 2 NADP+ + H2O
show the reaction diagram
-
-
-
-
?
1-nitroso-3-nitrobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
show the reaction diagram
-
-
only the amino product can be observed
-
?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
show the reaction diagram
-
-
products are hydroxylamino- and amino-dinitrotoluene isomersd
-
?
2,4-dichloro-1-nitrobenzene + 2 NADPH + 2 H+
2,4-dichloro-N-hydroxyaniline + 2 NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2,4-dinitrochlorobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
show the reaction diagram
2,4-dinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
show the reaction diagram
2-chloro-6-nitrotoluene + 3 NADPH + 3 H+
3-chloro-2-methylaniline + 3 NADP+ + 2 H2O
show the reaction diagram
-
-
-
-
?
2-chloronitrobenzene + 2 NADPH + 2 H+
2-chloro-N-hydroxyaniline + 2 NADP+ + H2O
show the reaction diagram
2-nitrotoluene + 3 NADPH + 3 H+
2-toluidine + 3 NADP+ + 2 H2O
show the reaction diagram
-
-
-
-
?
3-bromo-4-nitrotoluene + 3 NADPH + 3 H+
2-bromo-4-methylaniline + 3 NADP+ + 2 H2O
show the reaction diagram
-
-
-
-
?
3-chloronitrobenzene + 2 NADPH + 2 H+
3-chloro-N-hydroxyaniline + 2 NADP+ + H2O
show the reaction diagram
3-nitrophenol + 2 NADPH + 2 H+
3-(hydroxyamino)phenol + 2 NADP+ + H2O
show the reaction diagram
-
recombinant protein, 66% of the activity with 4-chloronitrobenzene
-
?
3-nitrotoluene + 2 NADPH + 2 H+
N-hydroxy-3-methylaniline + 2 NADP+ + H2O
show the reaction diagram
4-chloronitrobenzene + 2 NADH + 2 H+
4-chloro-N-hydroxyaniline + 2 NAD+ + H2O
show the reaction diagram
-
-
-
?
4-chloronitrobenzene + 2 NADPH + 2 H+
2-amino-5-chlorophenol + 2 NADP+ + H2O
show the reaction diagram
-
reaction in presence of hydroxylaminobenzene mutase CnbB
-
?
4-chloronitrobenzene + 2 NADPH + 2 H+
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
show the reaction diagram
4-nitrochlorobenzene + 3 NADPH + 3 H+
4-chloroaniline + 3 NADP+ + 2 H2O
show the reaction diagram
-
-
-
-
?
4-nitrophenol + 3 NADPH + 3 H+
4-aminophenol + 3 NADP+ + 2 H2O
show the reaction diagram
4-nitrotoluene + 2 NADPH + 2 H+
N-hydroxy-4-methylaniline + 2 NADP+ + H2O
show the reaction diagram
-
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + 2 NADPH + 2 H+
? + 2 NADP+
show the reaction diagram
-
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
show the reaction diagram
nitrobenzene + 2 NADPH + 2 H+
aniline + 2 NADP+ + H2O
show the reaction diagram
-
reduction of nitrobenzene to aniline occurs through the formation of nitrosobenzene and phenylhydroxylamine as intermediates. More than 99% overall conversion
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
show the reaction diagram
nitrobenzene + 2 NADPH + 2 H+
N-phenylhydroxylamine + 2 NADP+ + H2O
show the reaction diagram
nitrobenzene + 3 NADH + 3 H+
aniline + 3 NAD+ + 2 H2O
show the reaction diagram
-
30% activity compared to 3 NADPH
-
-
?
nitrobenzene + 3 NADPH + 3 H+
aniline + 3 NADP+ + 2 H2O
show the reaction diagram
nitrobenzene + FMN
aniline + ?
show the reaction diagram
-
80% activity compared to 3 NADPH
-
-
?
nitrobenzene + menadione
N-hydroxyaniline + menadiol + H2O
show the reaction diagram
nitrofurazone + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
show the reaction diagram
nitrosobenzene + NADPH + H+
N-hydroxyaniline + NADP+ + H2O
show the reaction diagram
[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
show the reaction diagram
[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+
?
show the reaction diagram
[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+
?
show the reaction diagram
additional information
?
-