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Information on EC 1.3.1.74 - 2-alkenal reductase [NAD(P)+]
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1.3.1.74 2-alkenal reductase [NAD(P)+]IUBMB Comments
Highly specific for 4-hydroxynon-2-enal and non-2-enal. Alk-2-enals of shorter chain have lower affinities. Exhibits high activities also for alk-2-enones such as but-3-en-2-one and pent-3-en-2-one. Inactive with cyclohex-2-en-1-one and 12-oxophytodienoic acid. Involved in the detoxication of alpha,beta-unsaturated aldehydes and ketones [cf. EC 1.3.1.102, 2-alkenal reductase (NADP+)].
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Word Map
- 1.3.1.74
- dicumarol
-
alpha,beta-unsaturated
- quercitrin
-
2-alkenals
-
15-ketoprostaglandins
-
13-reductase
- acylfulvenes
- dihydrochalcone
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Synonyms
2-alkenal reductase, 2AER, AER, alkenal/one oxidoreductase, alkenal/one reductase, AOR, At-AER, At5g16970, AtAOR, bifunctional LTB4 12-hydroxydehydrogenase/15-oxo-prostaglandin 13-reductase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
alkenal/one oxidoreductase
AOR
bifunctional LTB4 12-hydroxydehydrogenase/15-oxo-prostaglandin 13-reductase
-
a beta-NADPH-dependent alkenal/one oxidoreductase which has a role for leukotriene B4 12-hydroxydehydrogenase/15-ketoprostaglandinDELTA13-reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a n-alkanal + NAD(P)+ = an alk-2-enal + NAD(P)H + H+
-
-
-
-
a n-alkanal + NAD(P)+ = an alk-2-enal + NAD(P)H + H+
catalytic and kinetic mechanism
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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SYSTEMATIC NAME
IUBMB Comments
n-alkanal:NAD(P)+ 2-oxidoreductase
Highly specific for 4-hydroxynon-2-enal and non-2-enal. Alk-2-enals of shorter chain have lower affinities. Exhibits high activities also for alk-2-enones such as but-3-en-2-one and pent-3-en-2-one. Inactive with cyclohex-2-en-1-one and 12-oxophytodienoic acid. Involved in the detoxication of alpha,beta-unsaturated aldehydes and ketones [cf. EC 1.3.1.102, 2-alkenal reductase (NADP+)].
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CAS REGISTRY NUMBER
COMMENTARY
137367-20-5
-
52227-95-9
-
57406-74-3
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9032-20-6
-
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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
15-deoxy-DELTA12,14-prostaglandin J2 + NADPH + H+
12,13-dihydro-15-deoxy-DELTA12,14-prostaglandin J2 + NADP+
-
-
-
-
r
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+
-
at 12% of the rate with 2E-nonenal
-
-
?
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
-
-
?
4-hydroxy-(2E)-nonenal + NAD(P)H
4-hydroxynonylaldehyde + NAD(P)+
-
-
-
?
4-hydroxy-(2E)-nonenal + NAD(P)H
4-hydroxynonylaldehyde + NAD(P)+
-
-
-
-
?
illudin M + NADPH
?
-
extremly cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
illudin S + NADPH
?
-
extremly cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
irofulven + NADPH
?
-
less cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
n-alkanal + NAD(P)+
alk-2-enal + NAD(P)H
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carbon chain length C3-C9 serves as substrates
-
-
?
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
?
-
-
reaction product identification by mass spectrometry
-
-
?
additional information
?
-
-
regio- and stereochemistry of hydride transfer, overview
-
-
?
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NATURAL SUBSTRATE
NATURAL 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
illudin M + NADPH
?
-
extremly cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
illudin S + NADPH
?
-
extremly cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
irofulven + NADPH
?
-
less cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NADH
-
enzyme operates 30times faster in the presence of NADPH than in the presence of NADH
NADH
enzyme operates 30times faster in the presence of NADPH than in the presence of NADH
NADPH
-
enzyme operates 30times faster in the presence of NADPH than in the presence of NADH
NADPH
enzyme operates 30times faster in the presence of NADPH than in the presence of NADH
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
irofulven
-
recombinant human 293 cells show 100fold increased sensitivity compared to the wild-type human 293 cells
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
estradiol
-
the transcription of 2AER is estradiol-induced and correlates with conditional salt tolerance
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Neoplasms
Increased expression of prostaglandin reductase 1 in hepatocellular carcinomas from clinical cases and experimental tumors in rats.
Neoplasms
NADPH alkenal/one oxidoreductase activity determines sensitivity of cancer cells to the chemotherapeutic alkylating agent irofulven.
Neoplasms
Nrf2-mediated induction of cytoprotective enzymes by 15-deoxy-Delta12,14-prostaglandin J2 is attenuated by alkenal/one oxidoreductase.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.02
2-[4-[(E)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid
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at 30°C
additional information
additional information
-
ordered Theorell-Chance kinetic mechanism, steady-state kinetics, detailed analysis, kinetic isotopic effects
-
0.004
NADPH
-
recombinant enzyme, pH 7.2, 25°C, with substrate trans-2-nonenal
0.032
NADPH
-
recombinant enzyme, pH 7.2, 25°C, with substrate trans-3-nonen-2-one
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
-
product inhibition kinetics
-
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
-
Dbr1 expression is readily detectable in aerial parts of the plant, but not in the roots
brenda
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
-
At-AER protein fused with the Aequorea victoria green fluorescent protein localizes in cytosol and the nucleus in Bright-Yellow 2 cells of tabacco
brenda
-
At-AER protein fused with the Aequorea victoria green fluorescent protein localizes in cytosol and the nucleus in Bright-Yellow 2 cells of tobacco
brenda
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
leaf aldehyde compositions in the AER-overproducing tobaccos and wild type leaves are analyzed. In wild-tpye leaves, 2-alkenals such as (E)-2-pentenal, acrolein, and (E)-2-hexenal are increased by 70-290% after 30 min-illumination. In the leaves of AER-tobaccos, light-dependent increase of these 2-alkenals is lower
Show AA Sequence and Transmembrane Helices (3132 entries)
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Please use the AA Sequence and Transmembrane Helices Search for a specific query.
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PDB
SCOP
CATH
UNIPROT
ORGANISM
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
42000
45000
45000
-
2 * 45000, SDS-PAGE, enzyme can form dimeric and trimeric aggretates
45000
-
3 * 45000, SDS-PAGE, enzyme can form dimeric and trimeric aggretates
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
dimer
-
2 * 45000, SDS-PAGE, enzyme can form dimeric and trimeric aggretates
monomer
trimer
-
3 * 45000, SDS-PAGE, enzyme can form dimeric and trimeric aggretates
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
2',5'-ADP Sepharose 4B column chromatography, Resource Q column chromatography, and HiLoad Superdex gel filtration
-
homogeneity
using anion exchange chromatography, hydroxyapatite, phenyl-Sepharose, and gel filtration
using anion exchange chromatography, hydroxyapatite, phenyl-Sepharose, and gel filtration
-
using anion exchange chromatography, hydroxyapatite, phenyl-Sepharose, and gel filtration
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Escherichia coli
heterologous expression of At-AER in tobacco suppresses the damages of leaf tissue by the exogenously added reactive carbonyl 4-hydroxy-(2E)-nonenal. The leaves of At-AER overproducing tobaccos suffer less damage caused by photooxidative stress due to MV/light or to intense light only
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human embryonic kidney cells (293 cell line) are transiently transfected either with an episomal rAOR overexpression vector (pCEP4-rAOR) or control vector (pCEP4). AOR transfected cells produce a 7-8fold higher expression of AOR than control cells
-
overexpressed in Escherichia coli as a GST-fusion protein
overexpression in human 293 cells increases their sensitivity to irofulven by 100fold compared to control human 293 cells
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Stoffel, W.; Därr, 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
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