1.7.1.6: azobenzene reductase

This is an abbreviated version!
For detailed information about azobenzene reductase, go to the full flat file.

Word Map on EC 1.7.1.6

Reaction

N,N-dimethyl-1,4-phenylenediamine
+
aniline
+ 2 NADP+ =
4-(dimethylamino)azobenzene
+ 2 NADPH + 2 H+

Synonyms

acpD, aerobic azoreductase, Azo 1, azo dye reductase, azo reductase, azo-dye reductase, AzoA, AzoB, AzoC, AzoEF1, AzoI, AzoII, AzoR, AzoR1, azoreductase, azoreductase 1, azoreductase B, azoreductase C, AZR, AzrA, AzrB, AzrC, AzrG, AzrS, bsAzoR, BTI1, class 1 azoreductase, class 2 azoreductase, dibromopropylaminophenylazobenzoic azoreductase, dimethylaminobenzene reductase, EC 1.6.6.7, ecAzoR, EF0404, efAzoR, EF_0404, flavin mononucleotide-containing azoreductase, flavin-dependent azoreductase, FMN-dependent NAD(P)H azoreductase, FMN-dependent NAD(P)H nitroreductase, FMN-dependent NADH-azo compound oxidoreductase, FMN-dependent NADH-azoreductase, methyl red azoreductase, N,N-dimethyl-4-phenylazoaniline azoreductase, NAD(P)H:1-(4'-sulfophenylazo)-2-naphthol oxidoreductase, NADH driven FMN dependent azoreductase, NADH-azoreductase, NADPH-dependent azoreductase Azr, NADPH-flavin azoreductase, NADPH2-dependent azoreductase, NC-reductase, new Coccine (NC)-reductase, nicotinamide adenine dinucleotide (phosphate) azoreductase, Orange I azoreductase, Orange II azoreductase, oxygen insensitive intracellular azoreductase, p-aminoazobenzene reductase, p-dimethylaminoazobenzene azoreductase, paAzoR1, PAMD_1, PpAzoR, reductase, azobenzene, rsAzoR, SO 4396

ECTree

     1 Oxidoreductases
         1.7 Acting on other nitrogenous compounds as donors
             1.7.1 With NAD+ or NADP+ as acceptor
                1.7.1.6 azobenzene reductase

Substrates Products

Substrates Products on EC 1.7.1.6 - azobenzene reductase

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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
1,2-dimethyl-4(p-carboxyphenylazo)-5-hydroxybenzene + NADPH
1,2-dimethyl-4-amino-5-hydroxybenzene + p-carboxyphenylamine + NADP+
show the reaction diagram
1-(2'-methyl-4'-sulfophenylazo)2-naphthol + NAD(P)H
4-amino-2-methyl-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
show the reaction diagram
-
-
-
?
1-(2-pyridylazo)-2-naphthol + NADH + H+
?
show the reaction diagram
C0STY0, C0STY1
-
-
-
?
1-(2-pyridylazo)-2-naphthol + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
ir
1-(3'-carboxyphenylazo)-2-naphthol + NAD(P)H
3-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
show the reaction diagram
-
-
-
?
1-(3'-phosphophenylazo)-2-naphthol + NAD(P)H
3-amino-1-benzenephosphate + NAD(P)+ + 1-amino-2-hydroxynaphthalene
show the reaction diagram
-
-
-
?
1-(3'-sulfophenylazo)-2-naphthol + NAD(P)H
3-amino-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
show the reaction diagram
-
-
-
?
1-(4'-carboxyphenylazo)-2-hydroxy-6-sulfonaphthalene + NAD(P)H
4-carboxyphenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
show the reaction diagram
-
-
-
?
1-(4'-carboxyphenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
show the reaction diagram
1-(4'-carboxyphenylazo)-2-naphthol + NADH
4-amino-1-benzoic acid + NAD+ + 1-amino-2-hydroxynaphthalene
show the reaction diagram
-
substrate is carboxy-Orange II
-
-
?
1-(4'-carboxyphenylazo)-4-naphthol + NAD(P)H
4-amino-1-benzoic acid + NAD(P)+ + 1-amino-4-hydroxynaphthalene
show the reaction diagram
1-(4'-nitrophenylazo)-2-hydroxy-6-sulfonaphthalene + NAD(P)H
4-nitrophenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
show the reaction diagram
-
-
-
?
1-(4'-phosphophenylazo)-2-naphthol + NAD(P)H
4-amino-1-benzenephosphate + NAD(P)+ + 1-amino-2-hydroxynaphthalene
show the reaction diagram
1-(4'-sulfonaminophenylazo-)2-naphthol + NAD(P)H
4-amino-1-benzenesulfonamine + NAD(P)+ + 1-amino-2-hydroxynaphthalene
show the reaction diagram
1-(4'-sulfophenylazo)-2-hydroxy-6-carboxynaphthalene + NAD(P)H
4-sulfophenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-carboxynaphthalene
show the reaction diagram
-
-
-
?
1-(4'-sulfophenylazo)-2-hydroxy-6-sulfonaphthalene + NAD(P)H
4-sulfophenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
show the reaction diagram
-
-
-
?
1-(4-sulfo-1-naphthylazo)-2-naphthol-3,6-disulfonic acid + NADPH
alpha-naphthylamine-4-sulfonic acid + beta-naphthol-3,6-disulfonic acid + NADP+
show the reaction diagram
1-methyl-1-([1-[(Z)-(methyl[4-[(E)-2-[6'-[(E)-[4-[methyl([4-[(1-methylpyrrolidinium-1-yl)methyl]-1H-1,2,3-triazol-1-yl]methyl)amino]phenyl]diazenyl]-3-oxo-3H-spiro[2-benzofuran-1,9'-xanthen]-3'-yl]ethenyl]phenyl]iminio)methyl]-1H-1,2,3-triazol-4-yl]methyl)pyrrolidinium + FMN + NADH + H+
? + NAD+
show the reaction diagram
-
pro-fluorophore, based on fluorescent rhodamine 110. Upon reduction of the two diazo bonds, substrate shows a green fluorescence suitable for the detection of azoreductases
-
-
?
1-phenylazo-2-hydroxy-6-carboxynaphthalene + NAD(P)H
phenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-carboxynaphthalene
show the reaction diagram
-
-
-
?
1-phenylazo-2-hydroxy-6-sulfonaphthalene + NAD(P)H
phenylamine + NAD(P)+ + 1-amino-2-hydroxy-6-sulfonaphthalene
show the reaction diagram
-
-
-
?
2 ferricyanide + NADPH
2 ferrocyanide + NADP+ + H+
show the reaction diagram
-
-
-
?
2'-carboxy-4-N,N-dimethylazobenzene + NAD(P)H
2-carboxy-1-phenylamine + N,N-dimethyl-1,4-phenylenediamine + NADP+
show the reaction diagram
-
trivial name methyl red
-
?
2,2'-(1,8-dihydroxy-3,6-disulfonaphthalene-2,7-bis-azo)-bis(benzenearsonic acid) + NAD(P)H
?
show the reaction diagram
-
reduced to an anion free radical by an outer membrane azoreductase
-
-
?
2-hydroxy-1,4-naphthoquinone + NADH + H+
?
show the reaction diagram
-
-
-
?
2-hydroxy-1,4-naphthoquinone + NADPH + H+
?
show the reaction diagram
-
lawsone, quinone reductase activity
-
-
?
2-methyl-1,4-benzoquinone + NADH + H+
?
show the reaction diagram
-
-
-
?
2-methyl-1,4-naphthoquinone + NADH + H+
?
show the reaction diagram
-
menadione, vitamin K3
-
-
?
2-methyl-1,4-naphthoquinone + NADPH + H+
?
show the reaction diagram
-
menadione, quinone reductase activity
-
-
?
2-[4-(dimethylamino)phenylazo]benzoic acid + NADH
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
show the reaction diagram
2-[4-(dimethylamino)phenylazo]benzoic acid + NADPH
N,N-dimethyl-p-phenylenediamine + 2-aminobenzoic acid + NADP+
show the reaction diagram
-
-
-
-
?
3-methyl-4-(2-chlorophenylhydrazone)-isoxazol-5-one + NAD(P)H
o-chloroaniline + ?
show the reaction diagram
-
fungicide, trivial name drazoxolon, 90-80% activity with NADH
-
?
4'-diethylaminoazobenzene-2-carboxylic acid + NADH + H+
?
show the reaction diagram
-
ethyl red
-
-
?
4'-dimethylaminoazobenzene-2-carboxylic acid + NADH + H+
2-aminobenzoic acid + N,N'-dimethyl-p-phenylenediamine + NAD+
show the reaction diagram
-
methyl red
-
-
?
4-(4-aminophenylazo)benzenesulfonic acid + NADPH + H+
?
show the reaction diagram
about 25% specific activity compared to balsalazide
-
-
?
4-(4-nitrophenylazo)-1-naphthol + NAD(P)H
?
show the reaction diagram
4-(dimethylamino)azobenzene + 2 NADPH
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+ + 2 H+
show the reaction diagram
4-(dimethylamino)azobenzene + NADPH + H+
N,N-dimethyl-1,4-phenylenediamine + aniline + NADP+
show the reaction diagram
4-([4-(dimethylamino)phenyl]diazenyl)benzene-1-sulfonate + NADPH + H+
? + NADP+
show the reaction diagram
4-dimethylaminoazobenzene-2'-carboxylic acid + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
show the reaction diagram
4-dimethylaminoazobenzene-2'-carboxylic acid + NADPH + H+
anthranilate + N,N'-dimethylamino-aniline + NAD+
show the reaction diagram
i.e. methyl red
-
-
?
4-[(2-hydroxy-1-naphthalenyl)azo]benzene sulfonic acid + NAD(P)H
4-amino-1-benzenesulfonic acid + NAD(P)+ + 1-amino-2-hydroxynaphthalene
show the reaction diagram
4-[(4-hydroxy-1-naphthalenyl)azo]benzene sulfonic acid + NAD(P)H
4-amino-benzenesulfonic acid + 1-amino-4-hydroxynaphthalene + NADP+
show the reaction diagram
Acid orange 5 + NADH
?
show the reaction diagram
acid Orange 7 + NAD(P)H
?
show the reaction diagram
-
reduces also Acid Orange 6, 8 and 12, Acid Red 88 and 151, NADH is more effective
-
-
?
acid red 119 + NADH + H+
? + NAD+
show the reaction diagram
acid red 88 + NAD(P)H + H+
?
show the reaction diagram
-
-
-
?
acid red 88 + NADH + H+
?
show the reaction diagram
C0STY0, C0STY1
-
-
-
?
acid red 88 + NADH + H+
? + NAD+
show the reaction diagram
acid red 88 + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
Acid red G + NADH
?
show the reaction diagram
acid yellow 19 + NADPH + H+
? + NADP+
show the reaction diagram
-
low activity
-
-
?
amaranth + ?
?
show the reaction diagram
Amaranth + NADH
?
show the reaction diagram
Amaranth + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
Amido black + NADH
?
show the reaction diagram
-
-
-
-
?
anthraquinone-2,6-disulfonate + NADH + H+
?
show the reaction diagram
-
-
-
?
anthraquinone-2,6-disulfonate + NADPH + H+
?
show the reaction diagram
-
quinone reductase activity
-
-
?
anthraquinone-2-sulfonate + NADH + H+
?
show the reaction diagram
-
-
-
?
anthraquinone-2-sulfonate + NADPH + H+
?
show the reaction diagram
-
quinone reductase activity
-
-
?
Atul acid black + NADH
?
show the reaction diagram
-
-
-
-
?
balsalazide + NADPH + H+
?
show the reaction diagram
100% specific activity
-
-
?
balsalazide + NADPH + H+
? + NADP+
show the reaction diagram
-
tautomeric forms of balsalazide occur in solution, reaction mechanism, overview
-
-
?
balsalzide + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
-
?
BHQ-10 + NADPH + H+
? + NADP+
show the reaction diagram
congo red + NAD(P)H + H+
?
show the reaction diagram
-
-
-
?
Congo red + NADH + H+
? + NAD+
show the reaction diagram
di-sodium-(R)-benzyl-azo-2,7-dihydroxy-3,6-disulfonyl-naphthaline + NADH
?
show the reaction diagram
direct blue 14 + ?
o-tolidine + ?
show the reaction diagram
direct blue 15 + ?
?
show the reaction diagram
direct blue 15 + FAD + NADH + H+
? + NAD+
show the reaction diagram
-
highest activity in presence of both NADH and FAD
-
-
?
direct blue 15 + NAD(P)H
3,3'-dimethoxybenzidine + 1-hydroxy-2,8-diamino-3,6-naphthalenedisulfonic acid + NAD(P)+
show the reaction diagram
direct blue 15 + NAD(P)H + H+
?
show the reaction diagram
-
-
-
?
direct blue 15 + NADH + H+
? + NAD+
show the reaction diagram
Direct blue 71 + NADH
?
show the reaction diagram
direct red 28 + NADH + H+
benzidine + 4-aminobiphenyl + NAD+
show the reaction diagram
direct red 81 + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
disperse orange 3 + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
Disperse yellow + NADH
?
show the reaction diagram
-
85% of the activity with Methyl red
-
-
?
Eriochrome blue black + NADH
?
show the reaction diagram
-
-
-
-
?
ethyl red + NADH + H+
?
show the reaction diagram
C0STY0, C0STY1
-
-
-
?
ethyl red + NADH + H+
? + NAD+
show the reaction diagram
best substrate, 182% of the activity with methyl red at 30°C
-
-
ir
fast yellow + ?
?
show the reaction diagram
flame orange + NADPH + H+
? + NADP+
show the reaction diagram
golden yellow + NADH + H+
?
show the reaction diagram
Janus green B + NADPH + H+
? + NADP+
show the reaction diagram
methyl orange + ?
?
show the reaction diagram
Methyl orange + NADH
?
show the reaction diagram
methyl orange + NADH + H+
?
show the reaction diagram
C0STY0, C0STY1
-
-
-
?
methyl orange + NADH + H+
? + NAD+
show the reaction diagram
methyl orange + NADPH + H+
? + NADP+
show the reaction diagram
methyl red + ?
?
show the reaction diagram
-
-
-
-
?
methyl red + NAD(P)H + H+
?
show the reaction diagram
methyl red + NADH
2-aminobenzoic acid + N,N-dimethyl-1,4-phenylenediamine + NAD+
show the reaction diagram
-
-
-
-
?
methyl red + NADH + H+
?
show the reaction diagram
methyl red + NADH + H+
? + NAD+
show the reaction diagram
methyl red + NADH + H+
anthranilate + N,N'-dimethylaminoaniline + NAD+
show the reaction diagram
methyl red + NADH + H+
N,N-dimethyl-p-phenylenediamine and 2-aminobenzoic acid + NAD+
show the reaction diagram
F0PC48
-
-
-
?
methyl red + NADH + H+
o-aminobenzoic acid + N,N'-dimethyl-p-phenylenediamine + NAD+
show the reaction diagram
-
-
-
ir
methyl red + NADPH + H+
?
show the reaction diagram
methyl red + NADPH + H+
? + NADP+
show the reaction diagram
Mordant black 9 + NADH
?
show the reaction diagram
-
38% of activity
-
-
?
mordant blue 13 + NADH + H+
? + NAD+
show the reaction diagram
Mordant brown 96 + NADH
?
show the reaction diagram
-
28% of activity
-
-
?
N,N-dimethyl-1,4-phenylenediamine + aniline + 2 NADP+
4-(dimethylamino)azobenzene + 2 NADPH + 2 H+
show the reaction diagram
NADPH + 9,10-phenanthrenequinone
NADP+ + 9,10-phenanthrenequinol
show the reaction diagram
-
-
-
?
NADPH + H+ + 1,4-benzoquinone
NADP+ + 1,4-benzoquinol
show the reaction diagram
-
-
-
?
NADPH + H+ + 1,4-naphthoquinone
NADP+ + 1,4-naphthoquinol
show the reaction diagram
-
-
-
?
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
show the reaction diagram
-
-
-
?
NADPH + oxidized cytochrome c
NADP+ + reduced cytochrome c
show the reaction diagram
-
in the presence of menadione as electron carrier
-
?
naphthalene fast orange 2G + ?
?
show the reaction diagram
naphthol blue black + NADH + H+
? + NAD+
show the reaction diagram
-
78% conversion, analysis by UV-visible and FITR spectroscopy, HPLC, and GC-MS
-
-
?
Navitan fast blue S5R + NADH
metanilic acid + 1,4-diamino naphtalene + peri acid + NAD+
show the reaction diagram
-
-
-
-
?
neoprontosil + ?
?
show the reaction diagram
new coccine + NADPH
?
show the reaction diagram
new cossin + NADH + H+
?
show the reaction diagram
C0STY0, C0STY1
-
-
-
?
nitrofurazone + NAD(P)H + H+
?
show the reaction diagram
-
-
-
-
?
o-methyl red + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
olsalazine + NADPH + H+
?
show the reaction diagram
less than 10% specific activity compared to balsalazide
-
-
?
olsalazine + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
Orange G + NADH
?
show the reaction diagram
Orange I + NADH
?
show the reaction diagram
orange I + NADH + H+
?
show the reaction diagram
C0STY0, C0STY1
-
-
-
?
orange I + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
ir
Orange I + NADPH
?
show the reaction diagram
Orange I + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
orange II + ?
?
show the reaction diagram
orange II + NAD(P)H + H+
?
show the reaction diagram
-
-
-
?
orange II + NADH + H+
?
show the reaction diagram
C0STY0, C0STY1
-
-
-
?
orange II + NADH + H+
? + NAD+
show the reaction diagram
orange II + NADH + H+
sulfanilic acid + 1-amino-2-naphthol + NAD+
show the reaction diagram
-
-
-
-
?
Orange II + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
oxidized methyl red + NADH + H+
reduced methyl red + NAD+
show the reaction diagram
p-aminoazobenzene + ?
aniline + p-phenylenediamine + ?
show the reaction diagram
-
-
-
-
?
p-methyl red + NADH + H+
?
show the reaction diagram
-
-
-
-
?
Ponceau BS + NAD(P)H + H+
?
show the reaction diagram
-
-
-
?
Ponceau BS + NADH
?
show the reaction diagram
-
-
-
-
?
ponceau BS + NADH + H+
? + NAD+
show the reaction diagram
Ponceau BS + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
Ponceau S + NADH
?
show the reaction diagram
-
-
-
-
?
Ponceau S + NADPH
? + NADP+
show the reaction diagram
-
-
-
-
?
ponceau SX + NAD(P)H
?
show the reaction diagram
Ponceaux SX + NAD(P)H
?
show the reaction diagram
-
-
-
-
?
reactive black 5 + NADPH + H+
? + NADP+
show the reaction diagram
reactive black B5 + NADH + H+
? + NAD+
show the reaction diagram
reactive blue 222 + NADH + H+
? + NAD+
show the reaction diagram
reactive blue 3R + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
-
?
reactive orange 122 + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
-
?
reactive red 195 + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
-
?
reactive violet 5 + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
?
reactive violet 5 + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
?
reactive violet 5R + NADH + H+
? + NAD+
show the reaction diagram
-
-
-
-
?
reactive yellow 186 + NADH + H+
? + NAD+
show the reaction diagram
-
low activity
-
-
?
Red dye I + NADH
?
show the reaction diagram
Red dye II + NADH
?
show the reaction diagram
-
-
-
?
Red dye III + NADH
?
show the reaction diagram
-
-
-
?
red RB + NADH + H+
?
show the reaction diagram
remazol orange + NADH + H+
?
show the reaction diagram
remazol red + NADH + H+
?
show the reaction diagram
remazol yellow + NADH + H+
?
show the reaction diagram
Rocceline + NADPH
?
show the reaction diagram
-
-
-
-
?
Solar Orange + NADPH
?
show the reaction diagram
sulfasalazine + NADPH + H+
?
show the reaction diagram
about 20% specific activity compared to balsalazide
-
-
?
sulfasalazine + NADPH + H+
? + NADP+
show the reaction diagram
-
-
-
-
?
Sumifix Black B + NADPH
?
show the reaction diagram
-
-
-
-
?
sunset yellow + ?
?
show the reaction diagram
sunset yellow FCF + NADH + H+
?
show the reaction diagram
C0STY0, C0STY1
-
-
-
?
tartrazine + ?
?
show the reaction diagram
tartrazine + NAD(P)H
?
show the reaction diagram
-
-
-
-
?
Tropaeolin + NADH
?
show the reaction diagram
-
-
-
-
?
Trypan blue + NADH
?
show the reaction diagram
-
50% of the activity with Methyl red
-
-
?
additional information
?
-