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(+)-acylfulvene + NADPH
?
-
-
-
-
?
(+)-hydroxymethylacylfulvene + NADPH
?
-
-
-
-
?
(-)-acylfulvene + NADPH
?
-
-
-
-
?
(-)-hydroxymethylacylfulvene + NADPH
?
-
-
-
-
?
(2E),(6Z)-nonadienal + NADPH
?
-
-
-
-
?
(2E)-4-hydroxynon-2-enal + NADPH + H+
4-hydroxynonanal + NADP+
-
-
-
-
?
(2E)-hexenal + NAD(P)H
n-hexanal + NAD(P)+
-
-
-
?
(2E)-nonenal + NAD(P)H
n-nonanal + NAD(P)+
-
-
-
-
?
(2E)-pentenal + NAD(P)H
n-pentanal + NAD(P)+
-
-
-
-
?
(S)-(+)-carvone + NADPH + H+
? + NADP+
-
-
-
?
1-cyclohexene-1-carboxaldehyde + NADPH + H+
cyclohexanecarboxaldehyde + NADP+
-
-
-
?
1-octen-3-one + NADPH + H+
octan-3-one + NADP+
-
-
-
?
1-penten-3-one + NADH
? + NAD+
1-penten-3-one + NADH
pentan-3-one + NAD+
-
-
-
?
1-penten-3-one + NADPH
? + NADP+
-
-
-
?
1-penten-3-one + NADPH
pentan-3-one + NADP+
13-oxo-(9E,11Z)-octadecadienoic acid + NADPH
?
-
-
-
-
?
15-deoxy-DELTA12,14-prostaglandin + NADPH
?
-
-
-
-
?
15-deoxy-DELTA12,14-prostaglandin J2 + NADPH + H+
12,13-dihydro-15-deoxy-DELTA12,14-prostaglandin J2 + NADP+
-
-
-
-
r
15-oxoprostaglandin E1 + NAD(P)H
? + NAD(P)+
-
-
-
-
?
2-[4-[(E)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid + NADPH
2-[4-[(2-oxocyclohexyl)methyl]phenyl]propanoic acid + NADP+
-
2-[4-[(E)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid is also known as CS-670
-
-
?
2E-hexenal + NADPH + H+
hexanal + NADP+
2E-nonenal + NADPH + H+
nonanal + NADP+
-
-
-
-
?
3-buten-2-one + NAD(P)H
2-butanone + NAD(P)+
-
-
-
-
?
3-buten-2-one + NADH
2-butanone + NAD+
3-buten-2-one + NADPH
2-butanone + NADP+
3-nonen-2-one + NADPH
nonan-2-one
-
-
-
-
?
3-penten-2-one + NAD(P)H
2-pentanone + NAD(P)+
-
-
-
-
?
3-penten-2-one + NADH
2-pentanone + NAD+
-
-
-
?
3-penten-2-one + NADPH
2-pentanone + NADP+
-
-
-
?
4-hexen-3-one + NADH
hexan-3-one + NAD+
4-hexen-3-one + NADPH
hexan-3-one + NADP+
4-hydroxy-(2E)-hexenal + NAD(P)H
4-hydroxyhexenal + NAD(P)+
-
-
-
-
?
4-hydroxy-(2E)-nonenal + NAD(P)H
4-hydroxynonylaldehyde + NAD(P)+
4-hydroxy-(2E)-nonenal + NADPH + H+
4-hydroxynonanal + NADP+
-
-
-
-
?
4-oxo-(2E)-nonenal + NADPH + H+
4-oxononanal + NADP+
-
-
-
-
?
9-oxo-(10E,12Z)-octadecadienoic acid + NADPH
?
-
-
-
-
?
artemisinic aldehyde + NADPH + H+
dihydroartemisinic aldehyde + NADP+
-
at 1.9% of the rate with 2E-nonenal
88% 11S- and 12% 11R-isomer
-
?
benzylidine acetone + NAD(P)H
? + NAD(P)+
-
reduction of alpha,beta-double bond
-
-
?
cinnamyl aldehyde + NADPH + H+
3-phenylpropanal + NADP+
-
-
-
?
crotonaldehyde + NADH
butanal + NAD+
crotonaldehyde + NADPH
butanal + NADP+
diamide + NAD(P)H
? + NAD(P)+
-
-
-
-
?
ethyl vinyl ketone + NAD(P)H
diethylketone + NAD(P)+
-
-
-
-
?
methyl vinyl ketone + NAD(P)H
dimethylketone + NAD(P)+
-
-
-
-
?
n-alkanal + NAD(P)+
alk-2-enal + NAD(P)H
propenal + NAD(P)H
propanal + NAD(P)+
propenal + NADH
propanal + NAD+
propenal + NADPH
propanal + NADP+
trans,trans-2,4-alkadienal + NAD(P)H
? + NAD(P)+
-
-
-
-
?
trans-2-alkenal + NAD(P)H
alkanal + NAD(P)+
-
-
-
-
?
trans-2-nonenal + NAD(P)H
nonanal + NAD(P)+
-
-
-
-
?
trans-2-nonenal + NADPH + H+
nonanal + NADP+
-
-
-
?
trans-2-pentenal + NADPH
pentanal + NADP+
-
-
-
-
?
trans-3-nonen-2-one + NAD(P)H
2-nonanone + NAD(P)+
-
-
-
-
?
trans-4-hydroxy-2-alkenal + NAD(P)H
4-hydroxyalkanal + NAD(P)+
-
-
-
-
?
additional information
?
-
1-penten-3-one + NADH
? + NAD+
-
-
-
-
?
1-penten-3-one + NADH
? + NAD+
-
-
-
?
1-penten-3-one + NADPH
pentan-3-one + NADP+
-
-
-
-
?
1-penten-3-one + NADPH
pentan-3-one + NADP+
-
-
-
?
2E-hexenal + NADPH + H+
hexanal + NADP+
-
at 12% of the rate with 2E-nonenal
-
-
?
2E-hexenal + NADPH + H+
hexanal + NADP+
-
-
-
?
3-buten-2-one + NADH
2-butanone + NAD+
-
-
-
-
?
3-buten-2-one + NADH
2-butanone + NAD+
-
-
-
?
3-buten-2-one + NADPH
2-butanone + NADP+
-
-
-
-
?
3-buten-2-one + NADPH
2-butanone + NADP+
-
-
-
?
4-hexen-3-one + NADH
hexan-3-one + NAD+
-
-
-
-
?
4-hexen-3-one + NADH
hexan-3-one + NAD+
-
-
-
?
4-hexen-3-one + NADPH
hexan-3-one + NADP+
-
-
-
-
?
4-hexen-3-one + NADPH
hexan-3-one + NADP+
-
-
-
?
4-hydroxy-(2E)-nonenal + NAD(P)H
4-hydroxynonylaldehyde + NAD(P)+
-
-
-
?
4-hydroxy-(2E)-nonenal + NAD(P)H
4-hydroxynonylaldehyde + NAD(P)+
-
-
-
-
?
crotonaldehyde + NADH
butanal + NAD+
-
-
-
-
?
crotonaldehyde + NADH
butanal + NAD+
-
-
-
?
crotonaldehyde + NADPH
butanal + NADP+
-
-
-
-
?
crotonaldehyde + NADPH
butanal + NADP+
-
-
-
?
illudin M + NADPH
?
-
-
-
-
?
illudin M + NADPH
?
-
extremly cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
illudin S + NADPH
?
-
-
-
-
?
illudin S + NADPH
?
-
extremly cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
irofulven + NADPH
?
-
-
-
-
?
irofulven + NADPH
?
-
less cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
n-alkanal + NAD(P)+
alk-2-enal + NAD(P)H
-
carbon chain length C3-C9 serves as substrates
-
-
?
n-alkanal + NAD(P)+
alk-2-enal + NAD(P)H
-
role in detoxication
-
-
?
n-alkanal + NAD(P)+
alk-2-enal + NAD(P)H
-
-
-
-
?
n-alkanal + NAD(P)+
alk-2-enal + NAD(P)H
-
role in detoxication
-
-
?
propenal + NAD(P)H
propanal + NAD(P)+
-
synonym: acrolein
-
-
?
propenal + NAD(P)H
propanal + NAD(P)+
-
synonym: acrolein
-
-
?
propenal + NADH
propanal + NAD+
-
-
-
-
?
propenal + NADH
propanal + NAD+
-
-
-
?
propenal + NADPH
propanal + NADP+
-
-
-
-
?
propenal + NADPH
propanal + NADP+
-
-
-
?
additional information
?
-
-
catalyzes the hydrogenation of alpha,beta-unsaturated bonds, but not the reduction of the aldehyde moiety in 2-alkenal molecules
-
-
?
additional information
?
-
-
reduction of the alpha,beta-carbon-carbon double bond to a single bond, broad substrate specificity
-
-
?
additional information
?
-
-
phase2/antioxidative enzyme
-
-
?
additional information
?
-
-
reaction product identification by mass spectrometry
-
-
?
additional information
?
-
-
regio- and stereochemistry of hydride transfer, overview
-
-
?
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0.465
(+)-acylfulvene
-
pH 7.2, 37°C
0.243
(+)-hydroxymethylacylfulvene
-
pH 7.2, 37°C
0.538
(-)-acylfulvene
-
pH 7.2, 37°C
0.213
(-)-hydroxymethylacylfulvene
-
pH 7.2, 37°C
0.232
(2E)-hexenal
-
pH 6
0.005
(2E)-nonenal
-
pH 6
1.42
(2E)-pentenal
-
pH 6
0.0113
(2E,6Z)-nonadienal
-
pH 6.0
0.29 - 0.58
1-penten-3-one
0.00392
13-oxo-(9E,11Z)-octadecadienoic acid
-
pH 6.0
0.0096
15-deoxy-DELTA12,14-prostaglandin J2
-
pH 7.2
0.001
15-oxoprostaglandin E1
-
30°C
0.02
2-[4-[(E)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid
-
at 30°C
0.0064
2E-nonenal
-
pH 7.0, 30°C
0.055 - 2.88
3-buten-2-one
0.000673
3-nonen-2-one
-
pH 6.0
0.0052 - 0.63
3-penten-2-one
0.023 - 0.12
4-hexen-3-one
0.145
4-hydroxy-(2E)-hexenal
-
pH 6
0.0134
4-hydroxy-(2E)-nonenal
0.12
4-hydroxy-2-nonenal
-
30°C
0.00124
4-oxo-(2E)-nonenal
-
pH 6.0
0.01
9-oxo-(10E,12Z)-octadecadienoic acid
-
pH 6.0
0.071
artemisinic aldehyde
-
pH 7.0, 30°C
1.8 - 29.8
crotonaldehyde
0.11
ethyl vinyl ketone
-
30°C
0.109
illudin M
-
recombinant enzyme, pH 7.4, 37°C
0.308
illudin S
-
recombinant enzyme, pH 7.4, 37°C
0.145
irofulven
-
recombinant enzyme, pH 7.4, 37°C
0.078
trans-2-nonenal
-
recombinant enzyme, pH 7.2, 25°C
0.24
trans-2-pentenal
-
pH 7.2
0.028
trans-3-nonen-2-one
-
recombinant enzyme, pH 7.2, 25°C
additional information
additional information
-
ordered Theorell-Chance kinetic mechanism, steady-state kinetics, detailed analysis, kinetic isotopic effects
-
0.29
1-penten-3-one
-
pH 7.0, 25°C
0.58
1-penten-3-one
pH 7.0, 25°C
0.055
3-buten-2-one
-
pH 6
0.13
3-buten-2-one
-
pH 7.0, 25°C
2.88
3-buten-2-one
pH 7.0, 25°C
0.0052
3-penten-2-one
-
pH 6
0.63
3-penten-2-one
pH 7.0, 25°C
0.023
4-hexen-3-one
pH 7.0, 25°C
0.12
4-hexen-3-one
-
pH 7.0, 25°C
0.0134
4-hydroxy-(2E)-nonenal
-
pH 6.0
0.0134
4-hydroxy-(2E)-nonenal
-
pH 6
1.8
crotonaldehyde
-
pH 7.0, 25°C
29.8
crotonaldehyde
pH 7.0, 25°C
0.053
NADH
-
pH 7.0, 25°C
0.004
NADPH
-
recombinant enzyme, pH 7.2, 25°C, with substrate trans-2-nonenal
0.01
NADPH
-
pH 7.0, 25°C
0.032
NADPH
-
recombinant enzyme, pH 7.2, 25°C, with substrate trans-3-nonen-2-one
3.5
propenal
-
pH 7.0, 25°C
13.6
propenal
pH 7.0, 25°C
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Stoffel, W.; Drr, W.
Purification and characterization of 2-alkenal reductase
Hoppe-Seyler's Z. Physiol. Chem.
356
385-390
1975
Rattus norvegicus
brenda
Dick, R.A.; Kwak, M.K.; Sutter, T.R.; Kensler, T.W.
Antioxidative function and substrate specificity of NAD(P)H-dependent alkenal/one oxidoreductase. A new role for leukotriene B4 12-hydroxydehydrogenase/15-oxoprostaglandin 13-reductase
J. Biol. Chem.
276
40803-40810
2001
Rattus norvegicus
brenda
Mano, J.i.; Torii, Y.; Hayashi, S.i.; Takimoto, K.; Matsui, K.; Nakamura, K.; Inze, D.; Babiychuk, E.; Kushnir, S.; Asada, K.
The NADPH:quinone oxidoreductase P1-x-crystallin in Arabidopsis catalyzes the alpha,beta-hydrogenation of 2-alkenals: Detoxication of the lipid peroxide-derived reactive aldehydes
Plant Cell Physiol.
43
1445-1455
2002
Arabidopsis thaliana
brenda
Dick, R.A.; Yu, X.; Kensler, T.W.
NADPH alkenal/one oxidoreductase activity determines sensitivity of cancer cells to the chemotherapeutic alkylating agent irofulven
Clin. Cancer Res.
10
1492-1499
2004
Rattus norvegicus
brenda
Dick, R.A.; Kensler, T.W.
The catalytic and kinetic mechanisms of NADPH-dependent alkenal/one oxidoreductase
J. Biol. Chem.
279
17269-17277
2004
Rattus norvegicus
brenda
Yu, X.; Egner, P.A.; Wakabayashi, J.; Wakabayashi, N.; Yamamoto, M.; Kensler, T.W.
Nrf2-mediated induction of cytoprotective enzymes by 15-deoxy-DELTA12,14-prostaglandin J2 is attenuated by alkenal/one oxidoreductase
J. Biol. Chem.
281
26245-26252
2006
Rattus norvegicus
brenda
Gong, J.; Neels, J.F.; Yu, X.; Kensler, T.W.; Peterson, L.A.; Sturla, S.J.
Investigating the role of stereochemistry in the activity of anticancer acylfulvenes: synthesis, reductase-mediated bioactivation, and cellular toxicity
J. Med. Chem.
49
2593-2599
2006
Homo sapiens
brenda
Mano, J.; Belles-Boix, E.; Babiychuk, E.; Inze, D.; Torii, Y.; Hiraoka, E.; Takimoto, K.; Slooten, L.; Asada, K.; Kushnir, S.
Protection against photooxidative injury of tobacco leaves by 2-alkenal reductase. Detoxication of lipid peroxide-derived reactive carbonyls
Plant Physiol.
139
1773-1783
2005
Arabidopsis thaliana
brenda
Papdi, C.; Abraham, E.; Joseph, M.P.; Popescu, C.; Koncz, C.; Szabados, L.
Functional identification of Arabidopsis stress regulatory genes using the controlled cDNA overexpression system
Plant Physiol.
147
528-542
2008
Arabidopsis thaliana
brenda
Itoh, K.; Yamamoto, K.; Adachi, M.; Kosaka, T.; Tanaka, Y.
Leukotriene B4 12-hydroxydehydrogenase/15-ketoprostaglandin DELTA13-reductase (LTB4 12-HD/PGR) responsible for the reduction of a double-bond of the alpha,beta-unsaturated ketone of an aryl propionic acid non-steroidal anti-inflammatory agent CS-670
Xenobiotica
38
249-263
2008
Rattus norvegicus
brenda
Zhang, Y.; Teoh, K.; Reed, D.; Covello, P.
Molecular cloning and characterization of Dbr1, a 2-alkenal reductase from Artemisia annua
Botany
87
643-649
2009
Artemisia annua
-
brenda
Yamauchi, Y.; Hasegawa, A.; Taninaka, A.; Mizutani, M.; Sugimoto, Y.
NADPH-dependent reductases involved in the detoxification of reactive carbonyls in plants
J. Biol. Chem.
286
6999-7009
2011
Arabidopsis thaliana, Cucumis sativus (E2S0A5), Cucumis sativus (E2S0A6), Cucumis sativus
brenda
Mano, J.; Tokushige, K.; Mizoguchi, H.; Fujii, H.; Khorobrykh, S.
Accumulation of lipid peroxide-derived, toxic alpha, beta-unsaturated aldehydes (E)-2-pentenal, acrolein and (E)-2-hexenal in leaves under photoinhibitory illumination
Plant Biotechnol.
27
193-197
2010
Arabidopsis thaliana
-
brenda
Mas Y Mas, S.; Curien, G.; Giustini, C.; Rolland, N.; Ferrer, J.L.; Cobessi, D.
Crystal structure of the chloroplastic oxoene reductase ceQORH from Arabidopsis thaliana
Front. Plant Sci.
8
329
2017
Arabidopsis thaliana (Q39172), Arabidopsis thaliana
brenda
Wang, Y.; Zhao, Y.; Wang, S.; Liu, J.; Wang, X.; Han, Y.; Liu, F.
Up-regulated 2-alkenal reductase expression improves low-nitrogen tolerance in maize by alleviating oxidative stress
Plant Cell Environ.
44
559-573
2021
Zea mays (K7TK74)
brenda