1.7.1.B2: aromatic nitroreductase [NAD(P)H]
This is an abbreviated version!
For detailed information about aromatic nitroreductase [NAD(P)H], go to the full flat file.
Reaction
Synonyms
NfnB, NfsB, NfsB_Ec, NfsB_Pa, NprA, oxygen-insensitive nitroreductase (NAD(P)H), YfkO
ECTree
1.7.1.B2 aromatic nitroreductase [NAD(P)H]Advanced search results
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Substrates Products on EC 1.7.1.B2 - aromatic nitroreductase [NAD(P)H]
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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
2,4,6-trinitrotoluene + NADH + H+
4-hydroxyamino-2,6-dinitrotoluene + NAD+ + H2O
-
-
-
?
2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide + NADPH + H+
?
the wild type enzyme is largely inactive with 2-(2-methyl-5-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)acetamide (SN33623) as a substrate
-
-
?
2-(2-nitro-1H-imidazol-1-yl)-N-(2,2,3,3,3-pentafluoropropyl)-acetamide + NADPH + H+
?
-
-
-
?
2-amino-4,6-dinitrotoluene + NADH + H+
4-hydroxyamino-2-aminotoluene + NAD+ + H2O
-
-
-
?
2-[(2-bromoethyl)(2-[(2-hydroxyethyl)carbamoyl]-4,6-dinitrophenyl)amino]ethyl methanesulfonate + NADPH + H+
?
-
-
-
?
4-amino-2,6-dinitrotoluene + NADH + H+
2-hydroxyamino-4-aminotoluene + NAD+ + H2O
-
-
-
?
methyl (6-nitro-4-oxoquinolin-1(4H)-yl)acetate + NADPH + H+
?
-
-
-
?
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxyamino-2,6-dinitrotoluene + NADP+ + H2O
-
-
-
?
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxyamino-2,6-dinitrotoluene + NADP+ + H2O
-
-
-
-
?
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxyamino-2,6-dinitrotoluene + NADP+ + H2O
i.e. TNT, NfsB reduces TNT to the para isomer 4-hydroxyamino-2,6-dinitrotoluene more easily than the ortho isomer 2-hydroxyamino-4,6-dinitrotoluene
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H + H+
? + NAD(P)+
i.e. CB1954, an aziridinyl dinitrobenzamide prodrug
-
-
?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NAD(P)H + H+
? + NAD(P)+
i.e. CB1954, an aziridinyl dinitrobenzamide prodrug, low activity
-
-
?
nitro-CBI-5-[(dimethylamino)ethoxy]indole + NAD(P)H + H+
? + NAD(P)+
a nitro-CBI prodrug, low activity
-
-
?
nitro-CBI-5-[(dimethylamino)ethoxy]indole + NAD(P)H + H+
? + NAD(P)+
a nitro-CBI prodrug, high activity
-
-
?
additional information
?
-
Escherichia coli nitroreductase NfsB can reduce nitrochloromethylbenzindolines, i.e. nitro-CBIs, in an oxygen-independent fashion, generating highly cytotoxic metabolites that alkylate the N3 of adenine in the minor groove of DNA
-
-
?
additional information
?
-
an intrinsically oxygen-insensitive nature of the two-electron reduction mechanism
-
-
?
additional information
?
-
no activity with 2,4-diamino-6-nitrotoluene and 2,6-diamino-4-nitrotoluene
-
-
?
additional information
?
-
Pseudomonas aeruginosa nitroreductase NfsB can reduce nitrochloromethylbenzindolines, i.e. nitro-CBIs, in an oxygen-independent fashion, generating highly cytotoxic metabolites that alkylate the N3 of adenine in the minor groove of DNA
-
-
?
additional information
?
-
an intrinsically oxygen-insensitive nature of the two-electron reduction mechanism
-
-
?
