Information on EC 1.7.1.16 - nitrobenzene nitroreductase

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The expected taxonomic range for this enzyme is: Bacteria, Eukaryota

EC NUMBER
COMMENTARY hide
1.7.1.16
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RECOMMENDED NAME
GeneOntology No.
nitrobenzene nitroreductase
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
N-phenylhydroxylamine + 2 NADP+ + H2O = nitrobenzene + 2 NADPH + 2 H+
show the reaction diagram
overall reaction
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N-phenylhydroxylamine + NADP+ = nitrosobenzene + NADPH + H+
show the reaction diagram
(1a)
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nitrosobenzene + NADP+ + H2O = nitrobenzene + NADPH + H+
show the reaction diagram
(1b)
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Aminobenzoate degradation
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Microbial metabolism in diverse environments
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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.
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
isolated from activated sludge of a wastewater treatment system
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Manually annotated by BRENDA team
isolated from activated sludge of a wastewater treatment system
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
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
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about 90% 1-amino-3-nitrobenzene plus 10% 1-hydroxylamino-3-nitrobenzene
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?
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
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-
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-
?
1-nitroso-3-nitrobenzene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
show the reaction diagram
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only the amino product can be observed
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?
2,4,6-trinitrotoluene + 2 NADPH + 2 H+
? + 2 NADP+ + H2O
show the reaction diagram
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products are hydroxylamino- and amino-dinitrotoluene isomersd
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?
2,4-dichloro-1-nitrobenzene + 2 NADPH + 2 H+
2,4-dichloro-N-hydroxyaniline + 2 NADP+ + H2O
show the reaction diagram
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-
-
-
?
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-chloronitrobenzene + 2 NADPH + 2 H+
2-chloro-N-hydroxyaniline + 2 NADP+ + 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
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recombinant protein, 66% of the activity with 4-chloronitrobenzene
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?
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
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-
?
4-chloronitrobenzene + 2 NADPH + 2 H+
2-amino-5-chlorophenol + 2 NADP+ + H2O
show the reaction diagram
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reaction in presence of hydroxylaminobenzene mutase CnbB
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?
4-chloronitrobenzene + 2 NADPH + 2 H+
4-chloro-N-hydroxyaniline + 2 NADP+ + H2O
show the reaction diagram
4-nitrotoluene + 2 NADPH + 2 H+
N-hydroxy-4-methylaniline + 2 NADP+ + H2O
show the reaction diagram
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?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + 2 NADPH + 2 H+
? + 2 NADP+
show the reaction diagram
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enzyme activates the dinitrobenzamide cancer prodrug CB1954, i.e. 5-(aziridin-1-yl)-2,4-dinitrobenzamide
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?
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
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 + 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
additional information
?
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
nitrobenzene + 2 NADPH + 2 H+
N-hydroxyaniline + 2 NADP+ + H2O
show the reaction diagram
nitrosobenzene + NADPH + H+
N-hydroxyaniline + NADP+ + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADH
NADPH is preferred over NADH
NADPH
additional information
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no cofactor: NADH
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-Naphthylamine
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1 mM, 31% residual activity
2-mercaptoethanol
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Ag+
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about 70% inhibition
Cd2+
1 mM, no residual activity
Cu2+
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about 70% inhibition
CuSO4
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0.5 mM, 78% residual activity
cysteine
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1 mM, 87% residual activity
dicumarol
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0.01 mM, 40% residual activity
glutathione
1 mM, 41% residual activity
Hg2+
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about 70% inhibition
menadione
1 mM, 61% residual activity
N-ethylmaleimide
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1 mM, 77% residual activity
neocuproin
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1 mM, 39% residual activity
nitrite
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1 mM, 77% residual activity
p-hydroxymercuribenzoate
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1 mM, 46% residual activity
potassium cyanate
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0.5 mM, 75% residual activity
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salicyl hydroxamate
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1 mM, 6% residual activity
Sodium azide
Triton X-100
1% w/v, 84% residual activity
Tween 20
1% w/v, 64% residual activity
ZnSO4
1 mM, no residual activity
additional information
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not inhibitory: Fe2+
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
hydroxylamine
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1 mM, 108% of initial activity
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.016
(2E)-2-[(5-nitrofuran-2-yl)methylidene]hydrazine-1-carboxamide
pH 8.0, 37C
0.128
1,3-dinitrobenzene
pH 8.0, 37C
0.468
2-chloronitrobenzene
pH 8.0, 37C
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0.264
3-nitrotoluene
pH 8.0, 37C
0.309
4-chloronitrobenzene
pH 8.0, 37C
0.282
4-nitrotoluene
pH 8.0, 37C
0.0117 - 0.054
5-(aziridin-1-yl)-2,4-dinitrobenzamide
0.009
menadione
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temperature not specified in the publication, pH 8.0
0.153 - 0.183
NADPH
0.002 - 0.545
nitrobenzene
1.763 - 5.123
nitrofurazone
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1
(2E)-2-[(5-nitrofuran-2-yl)methylidene]hydrazine-1-carboxamide
pH 8.0, 37C
0.24
1,3-dinitrobenzene
pH 8.0, 37C
0.15
2-chloronitrobenzene
pH 8.0, 37C
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0.18
3-nitrotoluene
pH 8.0, 37C
0.12
4-chloronitrobenzene
pH 8.0, 37C
0.13
4-nitrotoluene
pH 8.0, 37C
1.06
5-(aziridin-1-yl)-2,4-dinitrobenzamide
pH 8.0, 37C
1.05
NADPH
pH 8.0, 37C
0.18
nitrobenzene
pH 8.0, 37C
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
60
(2E)-2-[(5-nitrofuran-2-yl)methylidene]hydrazine-1-carboxamide
pH 8.0, 37C
1.9
1,3-dinitrobenzene
pH 8.0, 37C
0.32
2-chloronitrobenzene
pH 8.0, 37C
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0.7
3-nitrotoluene
pH 8.0, 37C
0.39
4-chloronitrobenzene
pH 8.0, 37C
0.46
4-nitrotoluene
pH 8.0, 37C
20
5-(aziridin-1-yl)-2,4-dinitrobenzamide
pH 8.0, 37C
6.9
NADPH
pH 8.0, 37C
0.33
nitrobenzene
pH 8.0, 37C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.01
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pH 7.0, 30C
8.1
substrate nitrofurazone, pH 7.2, 20C
13.6
substrate nitrofurazone, pH 7.5, 45C
245
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temperature not specified in the publication, pH 8.0
1900
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cosubstrate NADH, pH 7.0, 47C
3600
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cosubstrate NADPH, pH 7.0, 47C
11000
substrate nitrobenzene, pH 8.0, 37C
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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main localization
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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membrane-associated
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30000
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gel fitration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 27000, SDS-PAGE
monomer
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
molecular dynamics simulation of free enzyme in oxidized form, fully reduced enzyme with benzoate inhibitor and fully reduced enzyme with nitrobenzene. The complexed nitroreductase becomes more flexible overall upon complexation, particularly helix H6, in the vicinity of the binding site. Five regions which are highly conserved within the flavin mononucleotide (FMN) binding site are identified
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
membrane-associated enzyme, can be solubilized using Triton X-100
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
degradation