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1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanol + NADP+
i.e. mequindox, synthetic quinoxaline derivative, inhibitory to several Gram-positive and Gram-negative bacteria
-
-
?
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanone + NADPH + H+
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanol + NADP+
-
-
-
?
menadione + NADPH + H+
? + NADP+
-
-
-
?
1,4-benzoquinone + NADPH
? + NADP+
-
native and recombinant enzymes, low activity
-
-
?
1,4-naphthoquinone + NADPH + H+
? + NADP+
-
native and recombinant enzymes, low activity
-
-
?
1-butanal + NADPH
1-butanol + NADP+
-
-
-
-
?
1-heptanal + NADPH
1-heptanol + NADP+
-
-
-
-
?
1-hexanal + NADPH
1-hexanol + NADP+
-
-
-
-
?
1-indanone + NADPH
1-indanol + NADP+
-
-
-
-
?
1-nonanal + NADPH
1-nonanol + NADP+
-
-
-
-
?
1-pentanal + NADPH
1-pentanol + NADP+
-
-
-
-
?
1-phenyl-1,2-propanedione + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
1-phenylisatin + NADPH
? + NADP+
1-propanal + NADPH
1-propanol + NADP+
-
-
-
-
?
16-ketoestrone + NADPH
? + NADP+
-
recombinant enzyme
-
-
r
2,3-hexadione + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
2-benzoylpyridine + NADPH
(S)-alpha-phenyl-2-pyridylmethanol + NADP+
-
highly stereoselective reaction, native and recombinant enzymes, low activity
-
-
?
2-butanone + NADPH
2-butanol + NADP+
-
-
-
-
?
2-pentanone + NADPH
2-pentanol + NADP+
-
-
-
-
?
3-benzoylpyridine + NADPH
(S)-alpha-phenyl-3-pyridylmethanol + NADP+
3-benzoylpyridine + NADPH
?
-
-
-
-
?
3alpha-hydroxy-5beta-androstan-17-one + NADPH
?
-
-
-
-
?
4-benzoylpyridine + NADPH
?
-
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
4-benzoylpyridine + NADPH + H+
(S)-phenyl(pyridin-4-yl)methanol + NADP+
-
-
-
-
?
4-benzoylpyridine + NADPH + H+
phenyl-4-pyridylmethanol + NADP+
-
-
-
?
4-benzoylpyridine + NADPH + H+
S-(-)-phenylpyridin-4-yl-methynol + NADP+
-
stereoselective reduction
-
-
?
4-hexanoylpyridine + NADPH + H+
1-(pyridin-4-yloxy)hexan-1-ol + NADP+
4-nitroacetophenone + NADPH
1-(4-nitrophenyl)ethanol + NADP+
-
native and recombinant enzymes, low activity
-
-
?
4-nitroacetophenone + NADPH
?
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzyl alcohol + NADP+
-
-
-
-
?
4-nitrobenzaldehyde + NADPH
4-nitrobenzylalcohol + NADP+
-
native and recombinant enzymes
-
-
?
5alpha-androstan-17beta-ol-3-one + NADPH
?
-
-
-
-
?
5alpha-androstane-3,17-dione + NADPH
?
-
-
-
-
?
5beta-androstan-17beta-ol-3-one + NADPH
?
-
-
-
-
?
5beta-androstane-3,17-dione + NADPH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
?
-
-
-
-
?
9,10-phenanthrenequinone + NADPH
? + NADP+
-
best substrate, recombinant enzyme
-
-
r
9,10-phenanthroline + NADPH + H+
?
-
stereoselective reduction
-
-
?
9-cis-retinal + NADPH
9-cis-retinol + NADP+
-
recombinant enzyme
-
-
?
acetone + NADPH
propan-2-ol + NADP+
-
-
-
-
?
adrenochrome + NADPH + H+
?
-
stereoselective reduction
-
-
?
all-trans retinal + NADPH + H+
all-trans retinol + NADP+
-
-
-
-
?
all-trans-retinal + NADPH + H+
all-trans-retinol + NADP+
-
recombinant enzyme
-
-
?
benzaldehyde + NADPH
benzyl alcohol + NADP+
-
-
-
-
?
benzil + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
-
-
-
-
?
camphorquinone + NADPH + H+
camphorquinol + NADP+
-
-
-
-
?
cyclohexanone + NADPH
cyclohexanol + NADP+
-
-
-
-
?
decanal + NADPH
decanol + NADP+
-
-
-
-
?
diacetyl + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
ethyl benzoylformate + NADPH
? + NADP+
-
-
-
?
heptanophenone + NADPH
1-phenylheptan-1-ol + NADP+
hexanophenone + NADPH
1-phenylhexan-1-ol + NADP+
hexaphenone + NADPH
1-phenylhexan-1-ol + NADP+
-
native and recombinant enzymes
-
-
?
isatin + NADPH
? + NADP+
-
recombinant enzyme
-
-
r
menadione + NADPH
?
-
-
-
-
?
menadione + NADPH
? + NADP+
n-butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
NADPH + H+ + oxidized 2,6-dichlorophenolindophenol
NADP+ + reduced 2,6-dichlorophenolindophenol
-
-
-
-
?
nonanophenone + NADPH
1-phenylnonan-1-ol + NADP+
-
recombinant enzyme
-
-
?
octanal + NADPH + H+
1-octanol + NADP+
-
-
-
-
?
phenylglyoxal + NADPH
?
-
-
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
prostaglandin E2 + NADPH + H+
prostaglandin F2alpha + NADP+
-
-
-
-
r
pyridine-3-aldehyde + NADPH
?
-
-
-
-
?
pyridine-3-aldehyde + NADPH
pyridin-3-ylbutanol + NADP+
-
native and recombinant enzymes, low activity
-
-
?
pyridine-4-aldehyde + NADPH
?
-
-
-
-
?
pyridine-4-aldehyde + NADPH + H+
pyridin-4-ylmethanol + NADP+
testosterone + NADPH + H+
?
-
-
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
additional information
?
-
1-phenylisatin + NADPH
? + NADP+
-
-
-
?
1-phenylisatin + NADPH
? + NADP+
-
high activity, recombinant enzyme
-
-
?
3-benzoylpyridine + NADPH
(S)-alpha-phenyl-3-pyridylmethanol + NADP+
-
recombinant enzyme
-
-
?
3-benzoylpyridine + NADPH
(S)-alpha-phenyl-3-pyridylmethanol + NADP+
-
highly stereoselective reaction, native and recombinant enzymes
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
-
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
recombinant enzyme
-
-
?
4-benzoylpyridine + NADPH + H+
(S)-alpha-phenyl-4-pyridylmethanol + NADP+
-
highly stereoselective reaction, native and recombinant enzymes
-
-
?
4-hexanoylpyridine + NADPH + H+
1-(pyridin-4-yloxy)hexan-1-ol + NADP+
-
recombinant enzyme
-
-
?
4-hexanoylpyridine + NADPH + H+
1-(pyridin-4-yloxy)hexan-1-ol + NADP+
-
native and recombinant enzymes
-
-
?
heptanophenone + NADPH
1-phenylheptan-1-ol + NADP+
-
-
-
-
?
heptanophenone + NADPH
1-phenylheptan-1-ol + NADP+
-
recombinant enzyme
-
-
?
hexanophenone + NADPH
1-phenylhexan-1-ol + NADP+
-
-
-
-
?
hexanophenone + NADPH
1-phenylhexan-1-ol + NADP+
-
recombinant enzyme
-
-
?
menadione + NADPH
? + NADP+
-
recombinant enzyme
-
-
?
menadione + NADPH
? + NADP+
-
native and recombinant enzymes, low activity
-
-
?
n-butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
-
recombinant enzyme
-
-
?
n-butyrophenone + NADPH
1-phenylbutan-1-ol + NADP+
-
native and recombinant enzymes, low activity
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
-
-
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
-
recombinant enzyme
-
-
?
propiophenone + NADPH
1-phenylpropan-1-ol + NADP+
-
native and recombinant enzymes, low activity
-
-
?
pyridine-4-aldehyde + NADPH + H+
pyridin-4-ylmethanol + NADP+
-
recombinant enzyme
-
-
?
pyridine-4-aldehyde + NADPH + H+
pyridin-4-ylmethanol + NADP+
-
native and recombinant enzymes
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
-
-
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
-
recombinant enzyme
-
-
?
valerophenone + NADPH
1-phenylpentan-1-ol + NADP+
-
native and recombinant enzymes
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
overview
-
-
?
additional information
?
-
-
substrate specificity, overview
-
-
?
additional information
?
-
-
NADH also acts as cofactor
-
-
?
additional information
?
-
-
catalyzes pro-S stereoselective hydrogen transfer from NADPH
-
-
?
additional information
?
-
-
substrate specificity, no activity with 3-nitroacetophenone and 4-acetylpyridine, catalytic activity of the recombinant enzyme is similar to the native enzyme
-
-
?
additional information
?
-
-
the enzyme plays a role in superoxide formation through redox cycling of 9,10-phenanthrenequinone and, to a lesser extent, of adrenochrome in pig heart
-
-
?
additional information
?
-
-
the enzyme catalyses the NADPH-linked reduction of a variety of carbonyl compounds to their secondary alcohols
-
-
?
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4-hexanoylpyridine
-
competitive
9,10-phenanthroline
-
strong inhibition
butyrophenone
-
inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
genistein
-
50% inhibition at 0.028 mM
heptanophenone
-
inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
hexanophenone
-
competitive. Inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
kaempferol
-
50% inhibition at 0.015 mM
myristic acid
-
50% inhibition at 0.025 mM
propiophenone
-
inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
quercetin
-
50% inhibition at 0.016 mM
valerophenone
-
inhibitory potency in decreasing order: hexanophenone, valerophenone, heptanophenone, butyrophenone, propiophenone
additional information
-
adrenochrome is a poor inhibitor
-
additional information
-
the inhibitory potencies of alkyl 4-pyridyl ketones increases with an increase in the number up to five carbon atoms in the alkyl group, and 4-hexanoylpyridine is the most potent inhibitor of the enzyme activity. The inhibitory potencies of 4-heptanoylpyridine and 4-octanoylpyridine are lower than that of 4-hexanoylpyridine
-
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0.469
1-(3-methyl-1,4-dioxidoquinoxalin-2-yl)ethanone
pH 7.4, 37°C
0.116
1-(3-methyl-4-oxidoquinoxalin-2-yl)ethanone
pH 7.4, 37°C
0.0199
menadione
pH 7.4, 37°C
0.16
1,4-benzoquinone
-
pH 6.0, 25°C, recombinant enzyme
0.09
1,4-Naphthoquinone
-
pH 6.0, 25°C, recombinant enzyme
0.04
1-phenyl-1,2-propanedione
-
pH 6.0, recombinant enzyme
0.004
1-phenylisatin
-
pH 6.0, recombinant enzyme
0.086
16-ketoestrone
-
pH 6.0, recombinant enzyme
0.47
2,3-hexandione
-
pH 6.0, recombinant enzyme
0.93
2-benzoylpyridine
-
pH 6.0, 25°C, recombinant enzyme
0.09
4-hexanoylpyridine
-
pH 6.0, recombinant enzyme
1.2
4-Nitroacetophenone
-
pH 6.0, 25°C, recombinant enzyme
0.2 - 0.45
4-nitrobenzaldehyde
0.002
9,10-phenanthrenequinone
-
pH 6.0, recombinant enzyme
0.002
9,10-phenanthrenquinone
-
-
0.003
9,10-phenanthroline
-
pH 5.5, 37°C
0.083
Adrenochrome
-
pH 6.0, 37°C
0.13
benzil
-
pH 6.0, recombinant enzyme
0.084
butyrophenone
-
pH 6.0, 37°C
4.5
diacetyl
-
pH 6.0, recombinant enzyme
0.028 - 0.078
heptanophenone
0.021 - 0.037
hexanophenone
0.02
hexaphenone
-
pH 6.0, 25°C, recombinant enzyme
0.03
isatin
-
pH 6.0, recombinant enzyme
0.031
nonanophenone
-
pH 6.0, recombinant enzyme
0.249 - 0.89
propiophenone
0.16
prostaglandin E2
-
-
0.09
pyridin-4-yl hexanoate
-
pH 6.0, 25°C, recombinant enzyme
11.4
Pyridine-3-aldehyde
-
pH 6.0, 25°C, recombinant enzyme
0.048 - 0.052
valerophenone
additional information
additional information
-
0.76
3-benzoylpyridine
-
pH 6.0, 25°C, recombinant enzyme
0.76
3-benzoylpyridine
-
pH 6.0, recombinant enzyme
0.29
4-benzoylpyridine
-
pH 6.0, 25°C, recombinant enzyme
0.29
4-benzoylpyridine
-
pH 6.0, recombinant enzyme
0.2
4-nitrobenzaldehyde
-
pH 6.0, 25°C, recombinant enzyme
0.45
4-nitrobenzaldehyde
-
-
0.028
heptanophenone
-
pH 6.0, recombinant enzyme
0.078
heptanophenone
-
pH 6.0, 37°C
0.021
hexanophenone
-
pH 6.0, recombinant enzyme
0.037
hexanophenone
-
pH 6.0, 37°C
0.29
menadione
-
pH 6.0, 25°C, recombinant enzyme
0.29
menadione
-
pH 6.0, recombinant enzyme
0.17
n-butyrophenone
-
pH 6.0, 25°C, recombinant enzyme
0.17
n-butyrophenone
-
pH 6.0, recombinant enzyme
0.249
propiophenone
-
pH 6.0, 37°C
0.89
propiophenone
-
pH 6.0, 25°C, recombinant enzyme
0.89
propiophenone
-
pH 6.0, recombinant enzyme
1.4
Pyridine-4-aldehyde
-
pH 6.0, 25°C, recombinant enzyme
1.4
Pyridine-4-aldehyde
-
pH 6.0, recombinant enzyme
0.048
valerophenone
-
pH 6.0, 37°C
0.05
valerophenone
-
pH 6.0, 25°C, recombinant enzyme
0.052
valerophenone
-
pH 6.0, recombinant enzyme
additional information
additional information
-
-
-
additional information
additional information
-
kinetics
-
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Oritani, H.; Deyashiki, Y.; Nakayama, T.; Hara, A.; Sawada, H.; Matsuura, K.; Bunai, Y.; Ohya, I.
Purification and characterization of pig lung carbonyl reductase
Arch. Biochem. Biophys.
292
539-547
1992
Sus scrofa
brenda
Naganuma, H.; Kondo, J.I.; Kawahara, Y.
Enantiospecific assay for mammalian carbonyl reductase by liquid chromatography with fluorescence detection
J. Chromatogr.
532
65-74
1990
Oryctolagus cuniculus, Rattus norvegicus, Sus scrofa
brenda
Hara, A.; Oritani, H.; Deyashiki, Y.; Nakayama, T.; Sawada, H.
Activation of carbonyl reductase from pig lung by fatty acids
Arch. Biochem. Biophys.
292
548-554
1992
Sus scrofa
brenda
Ghosh, D.; Sawicki, M.; Pletnev, V.; Erman, M.; Ohno, S.; Nakajin, S.; Duax, W.L.
Porcine carbonyl reductase: structural basis for a functional monomer in short chain dehydrogenases/reductases
J. Biol. Chem.
276
18457-18463
2001
Sus scrofa
brenda
Forrest, G.L.; Gonzalez, B.
Carbonyl reductase
Chem. Biol. Interact.
129
21-40
2000
Cavia porcellus, Homo sapiens, Mus musculus, Rattus norvegicus, Sus scrofa
brenda
Schieber, A.; Frank, R.W.; Ghisla, S.
Purification and properties of prostaglandin 9-ketoreductase from pig and human kidney. Identity with human carbonyl reductase
Eur. J. Biochem.
206
491-502
1992
Homo sapiens, Sus scrofa
brenda
Usami, N.; Ishikura, S.; Abe, H.; Nagano, M.; Uebuchi, M.; Kuniyasu, A.; Otagiri, M.; Nakayama, H.; Imamura, Y.; Hara, A.
Cloning, expression and tissue distribution of a tetrameric form of pig carbonyl reductase
Chem. Biol. Interact.
143-144
353-361
2003
Sus scrofa
brenda
Shimada, H.; Fujiki, S.; Oginuma, M.; Asakawa, M.; Okawara, T.; Kato, K.; Yamamura, S.; Akita, H.; Hara, A.; Imamura, Y.
Stereoselective reduction of 4-benzoylpyridine by recombinant pig heart carbonyl reductase
J. Mol. Catal. B
23
29-35
2003
Sus scrofa
-
brenda
Aoki, K.; Tanaka, N.; Ishikura, S.; Araki, N.; Imamura, Y.; Hara, A.; Nakamura, K.T.
Crystallization and preliminary X-ray crystallographic studies of pig heart carbonyl reductase
Acta Crystallogr. Sect. F
62
1037-1040
2006
Sus scrofa
brenda
Oginuma, M.; Shimada, H.; Imamura, Y.
Involvement of carbonyl reductase in superoxide formation through redox cycling of adrenochrome and 9,10-phenanthrenequinone in pig heart
Chem. Biol. Interact.
155
148-154
2005
Sus scrofa
brenda
Imamura, Y.; Narumi, R.; Shimada, H.
Inhibition of carbonyl reductase activity in pig heart by alkyl phenyl ketones
J. Enzyme Inhib. Med. Chem.
22
105-109
2007
Sus scrofa
brenda
Tanaka, N.; Aoki, K.; Ishikura, S.; Nagano, M.; Imamura, Y.; Hara, A.; Nakamura, K.T.
Molecular basis for peroxisomal localization of tetrameric carbonyl reductase
Structure
16
388-397
2008
Sus scrofa (Q8WNV7), Sus scrofa
brenda
Tang, X.; Mu, P.; Wu, J.; Jiang, J.; Zhang, C.; Zheng, M.; Deng, Y.
Carbonyl reduction of mequindox by chicken and porcine cytosol and cloned carbonyl reductase 1
Drug Metab. Dispos.
40
788-795
2012
Gallus gallus (F1N8Y3), Gallus gallus, Sus scrofa (Q28960), Sus scrofa
brenda
Shimada, H.; Tanigawa, T.; Matayoshi, K.; Katakura, K.; Babazono, K.; Takayama, H.; Murahashi, T.; Akita, H.; Higuchi, T.; Eto, M.; Imamura, Y.
Comparative inhibition of tetrameric carbonyl reductase activity in pig heart cytosol by alkyl 4-pyridyl ketones
J. Enzyme Inhib. Med. Chem.
29
397-400
2014
Sus scrofa
brenda