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Information on EC 1.7.1.16 - nitrobenzene nitroreductase
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1.7.1.16 nitrobenzene nitroreductaseIUBMB Comments
Contains FMN. The enzyme, characterized from Pseudomonas species, catalyses two successive reductions of nitrobenzene, via a nitrosobenzene intermediate. It is also active on 1-chloro-4-nitrobenzene.
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Word Map
- 1.7.1.16
- pseudoalcaligenes
- flavin
- hydroxylaminobenzene
-
microbiol
- nitrofurazone
- fmn
- putida
- silica
- mutase
-
two-electron
- analysis
- mononucleotide
- degradation
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Reaction Schemes
+
2
+
=
+
2
+
2
Synonyms
nitrobenzene nitroreductase, oxygen-insensitive nad(p)h nitroreductase, 
more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
cnbA
NbzA
NTR
Oxygen-insensitive NAD(P)H nitroreductase
-
cnbA
-
-
gene name, ambiguous
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
N-phenylhydroxylamine + 2 NADP+ + H2O = nitrobenzene + 2 NADPH + 2 H+
overall reaction
-
-
-
N-phenylhydroxylamine + NADP+ = nitrosobenzene + NADPH + H+
(1a)
-
-
-
nitrosobenzene + NADP+ + H2O = nitrobenzene + NADPH + H+
(1b)
-
-
-
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PATHWAY SOURCE
PATHWAYS
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SYSTEMATIC NAME
IUBMB Comments
N-phenylhydroxylamine:NADP+ oxidoreductase
Contains FMN. The enzyme, characterized from Pseudomonas species, catalyses two successive reductions of nitrobenzene, via a nitrosobenzene intermediate. It is also active on 1-chloro-4-nitrobenzene.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
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+
1,3-dinitrobenzene + 2 NADPH + 2 H+
1-amino-3-nitrobenzene + 2 NADP+ + H2O
-
-
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
-
-
-
-
?
1-nitroso-3-nitrobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
-
only the amino product can be observed
-
?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
-
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
-
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
-
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+
-
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
-
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
-
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-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
-
-
?
(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
-
-
?
2,4-dinitrochlorobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
-
-
-
?
2,4-dinitrochlorobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
recombinant protein, 43% of the activity with 4-chloronitrobenzene
-
?
2,4-dinitrochlorobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
recombinant protein, 43% of the activity with 4-chloronitrobenzene
-
?
2,4-dinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
-
most abundant products are amino-nitrotoluene isomers, plus some hydroxylamino and diaminotoluene isomers
-
?
2,4-dinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
recombinant protein, 98% of the activity with 4-chloronitrobenzene
-
?
2,4-dinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
recombinant protein, 98% of the activity with 4-chloronitrobenzene
-
?
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
-
-
-
?
2-chloronitrobenzene + 2 NADPH + 2 H+
2-chloro-N-hydroxyaniline + 2 NADP+ + H2O
-
recombinant protein, 17% of the activity with 4-chloronitrobenzene
-
?
2-chloronitrobenzene + 2 NADPH + 2 H+
2-chloro-N-hydroxyaniline + 2 NADP+ + H2O
-
recombinant protein, 17% of the activity with 4-chloronitrobenzene
-
?
3-chloronitrobenzene + 2 NADPH + 2 H+
3-chloro-N-hydroxyaniline + 2 NADP+ + H2O
-
recombinant protein, 84% of the activity with 4-chloronitrobenzene
-
?
3-chloronitrobenzene + 2 NADPH + 2 H+
3-chloro-N-hydroxyaniline + 2 NADP+ + H2O
-
recombinant protein, 84% of the activity with 4-chloronitrobenzene
-
?
3-nitrotoluene + 2 NADPH + 2 H+
N-hydroxy-3-methylaniline + 2 NADP+ + H2O
-
-
-
?
3-nitrotoluene + 2 NADPH + 2 H+
N-hydroxy-3-methylaniline + 2 NADP+ + H2O
-
-
-
?
4-chloronitrobenzene + 2 NADPH + 2 H+
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
-
-
-
?
4-chloronitrobenzene + 2 NADPH + 2 H+
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
-
-
-
?
4-chloronitrobenzene + 2 NADPH + 2 H+
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
-
-
-
?
4-chloronitrobenzene + 2 NADPH + 2 H+
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
-
2.2 mol of NADPH is oxidized per mol of 4-chloronitrobenzene
-
?
4-nitrophenol + 3 NADPH + 3 H+
4-aminophenol + 3 NADP+ + 2 H2O
Psychrobacter sp. ANT206
-
the enzyme can degrade 4-nitrophenol in low temperature environment
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
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
-
enzyme activates the dinitrobenzamide cancer prodrug CB1954, i.e. 5-(aziridin-1-yl)-2,4-dinitrobenzamide
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
-
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
-
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
-
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
N-hydroxyaniline is the only product detected
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
-
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
N-hydroxyaniline is the only product detected
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
recombinant protein, 61% of the activity with 4-chloronitrobenzene
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
recombinant protein, 61% of the activity with 4-chloronitrobenzene
-
?
nitrobenzene + 2 NADPH + 2 H+
N-phenylhydroxylamine + 2 NADP+ + H2O
-
-
overall reaction
-
?
nitrobenzene + 2 NADPH + 2 H+
N-phenylhydroxylamine + 2 NADP+ + H2O
-
-
-
-
?
nitrobenzene + 2 NADPH + 2 H+
N-phenylhydroxylamine + 2 NADP+ + H2O
-
-
overall reaction
-
?
nitrobenzene + 3 NADPH + 3 H+
aniline + 3 NADP+ + 2 H2O
Psychrobacter sp. ANT206
-
100% activity with 3 NADPH
-
-
?
nitrobenzene + 3 NADPH + 3 H+
aniline + 3 NADP+ + 2 H2O
Psychrobacter sp. ANT206
-
the enzyme can degrade 4-nitrophenol in low temperature environment
-
-
?
nitrobenzene + menadione
N-hydroxyaniline + menadiol + H2O
-
-
-
?
nitrobenzene + menadione
N-hydroxyaniline + menadiol + H2O
-
-
-
?
nitrofurazone + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
enzyme activates the proantibiotic nitrofurazone
-
?
nitrofurazone + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
enzyme activates the proantibiotic nitrofurazone
-
?
nitrofurazone + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
-
-
-
?
nitrosobenzene + NADPH + H+
N-hydroxyaniline + NADP+ + H2O
-
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
-
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+
?
-
-
-
?
additional information
?
-
1.8 mol of NADPH is oxidized per mol of nitrobenzene converted to product
-
-
?
additional information
?
-
1.8 mol of NADPH is oxidized per mol of nitrobenzene converted to product
-
-
?
additional information
?
-
-
enzyme additionally catalyzes reduction of 2,4,6-trinitrotoluene
-
-
?
additional information
?
-
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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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
N-hydroxyaniline is the only product detected
-
?
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
-
N-hydroxyaniline is the only product detected
-
?
nitrosobenzene + NADPH + H+
N-hydroxyaniline + NADP+ + H2O
-
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
-
nitrosobenzene is not detected as an intermediate of nitrobenzene reduction, but nitrosobenzene is a substrate for the enzyme
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
FMN
tightly bound flavin mononucleotide cofactor in a ratio of 2 mol of flavin per mol of protein
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Neoplasms
Application of a microfluidic reactor for screening cancer prodrug activation using silica-immobilized nitrobenzene nitroreductase.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.016
(2E)-2-[(5-nitrofuran-2-yl)methylidene]hydrazine-1-carboxamide
pH 8.0, 37°C
0.009
menadione
temperature not specified in the publication, pH 8.0
0.0117
5-(aziridin-1-yl)-2,4-dinitrobenzamide
25°C, pH not specified in the publication
0.0337
5-(aziridin-1-yl)-2,4-dinitrobenzamide
imobilized enzyme, 25°C, pH not specified in the publication
0.183
NADPH
temperature not specified in the publication, pH 8.0
0.002
nitrobenzene
imobilized enzyme, 25°C, pH not specified in the publication
0.005
nitrobenzene
temperature not specified in the publication, pH 8.0
5.123
nitrofurazone
imobilized enzyme, 25°C, pH not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.1
(2E)-2-[(5-nitrofuran-2-yl)methylidene]hydrazine-1-carboxamide
pH 8.0, 37°C
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
60
(2E)-2-[(5-nitrofuran-2-yl)methylidene]hydrazine-1-carboxamide
pH 8.0, 37°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
13.6
substrate nitrofurazone, pH 7.5, 45°C
8.1
substrate nitrofurazone, pH 7.2, 20°C
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE