1.7.1.B3: aromatic nitroreductase [NADPH]
This is an abbreviated version!
For detailed information about aromatic nitroreductase [NADPH], go to the full flat file.
Word Map on EC 1.7.1.B3
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1.7.1.B3
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hypoplasia
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dermal
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x-linked
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goltz
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ectodermal
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malformation
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ocular
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porcupine
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mesoderm
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blaschko
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skew
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x-chromosome
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postzygotic
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teeth
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goltz-gorlin
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multisystemic
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herniation
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diaphragmatic
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x-inactivation
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angioma
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papillomas
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hernia
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wingless
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cutis
-
nail
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o-acyltransferase
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aplasia
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patchy
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environmental protection
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medicine
- 1.7.1.B3
-
hypoplasia
-
dermal
-
x-linked
-
goltz
-
ectodermal
-
malformation
-
ocular
-
porcupine
-
mesoderm
-
blaschko
-
skew
-
x-chromosome
-
postzygotic
-
teeth
-
goltz-gorlin
-
multisystemic
-
herniation
-
diaphragmatic
-
x-inactivation
-
angioma
-
papillomas
-
hernia
-
wingless
-
cutis
-
nail
-
o-acyltransferase
-
aplasia
-
patchy
- environmental protection
- medicine
Reaction
Synonyms
ipa-43d, More, NADPH-FMN reductase, NADPH-nitrofurazone reductase, NfrA1, NfsA, nitro/flavin reductase, nitrofurazone reductase, nitroreductase A, non-luminescent-bacterial NfsA/Frp-type enzyme, NR-A, ORF 17150, oxygen-insensitive NAD(P)H:nitroreductases, oxygen-insensitive nitroreductase (NADPH)
ECTree
1.7.1.B3 aromatic nitroreductase [NADPH]Advanced search results
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Substrates Products
Substrates Products on EC 1.7.1.B3 - aromatic nitroreductase [NADPH]
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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
nitro-CBI-5-[(dimethylamino)ethoxy]indole + NAD(P)H + H+
? + NAD(P)+
a nitro-CBI prodrug, low activity
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?
nitrofurazone + NADPH + H+
5-(hydroxyamino)furan-2-carbaldehyde semicarbazone + NADP+ + H2O
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxylamino-2,6-dinitrotoluene + NADP+ + H2O
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?
2,4,6-trinitrotoluene + NADPH + H+
4-hydroxylamino-2,6-dinitrotoluene + NADP+ + H2O
i.e. TNT, NfsA reduces TNT to the para isomer 4-hydroxylamino-2,6-dinitrotoluene more easily than the ortho isomer 2-hydroxylamino-4,6-dinitrotoluene
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?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NADPH + H+
? + NADP+
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i.e. CB1954, an aziridinyl dinitrobenzamide prodrug
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?
5-(aziridin-1-yl)-2,4-dinitrobenzamide + NADPH + H+
? + NADP+
i.e. CB1954, an aziridinyl dinitrobenzamide prodrug
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?
7-nitrocoumarin + 3 NADPH + 3 H+
7-aminocoumarin + 3 NADP+
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?
7-nitrocoumarin + 3 NADPH + 3 H+
7-aminocoumarin + 3 NADP+
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?
nitrofurazone + NADPH + H+
5-(hydroxyamino)furan-2-carbaldehyde semicarbazone + NADP+ + H2O
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?
nitrofurazone + NADPH + H+
5-(hydroxyamino)furan-2-carbaldehyde semicarbazone + NADP+ + H2O
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?
additional information
?
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the enzyme reduces both nitrofurazone and FMN effectively, see for EC 1.5.1.38, it is bifunctional as flavin reductase and nitroreductase. Two different FMN molecules are involved in the FMN reduction process: FMN tightly associated to the enzyme as prosthetic group and FMN as a substrate. The enzyme is also active with FAD, riboflavin, and lumiflavin, the two latter give the highest activity
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?
additional information
?
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an intrinsically oxygen-insensitive nature of the two-electron reduction mechanism
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?
additional information
?
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NADPH-dependent reduction of quinones, cf. EC 1.6.5.5, and nitroaromatic compounds by NfsA, overview. The reactivity of nitroaromatic compounds (log kcat/Km) follows a linear dependence on their single-electron reduction potential, indicating a limited role for compound structure or active site flexibility in their reactivity. The reactivity of quinones is lower than that of nitroaromatics having similar single-electron reduction potential values, except for the significantly enhanced reactivity of 2-OH-1,4-naphthoquinones. The reduction of quinones by NfsA is most consistent with a single-step (H-) hydride transfer mechanism, quantitative analysis of two-electron reduction of quinones and nitroaromatics, overview
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?
additional information
?
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NfsA has a broad substrate spectrum. Various nitroaromatic substrates, including 5-(aziridin-1-yl)-2,4-dinitrobenzamide (CB1954), 2,4,6-trinitrotoluene (TNT), and 2,4-dinitrotoluene (2,4-DNT), can serve as substrates
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?
additional information
?
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no activity with 2,4-diamino-6-nitrotoluene and 2,6-diamino-4-nitrotoluene
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?
additional information
?
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coenzyme Q and tetracycline may be used as electron acceptors, but with much lower specific activities than menadione, cf EC 1.6.5.5. Nitro compounds dinitrotoluene, 7-nitrocoumarin, and metronidazole can be used as electron acceptors
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additional information
?
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coenzyme Q and tetracycline may be used as electron acceptors, but with much lower specific activities than menadione, cf EC 1.6.5.5. Nitro compounds dinitrotoluene, 7-nitrocoumarin, and metronidazole can be used as electron acceptors
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