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Information on EC 1.3.1.74 - 2-alkenal reductase [NAD(P)+]
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EC Tree
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
- quercitrin
-
alpha,beta-unsaturated
- dicumarol
-
2-alkenals
-
15-ketoprostaglandins
-
13-reductase
- dihydrochalcone
- acylfulvenes
The expected taxonomic range for this enzyme is: Eukaryota, Bacteria, Archaea
Synonyms
double bond reductase, alkenal/one oxidoreductase, nadph-dependent alkenal/one oxidoreductase, at5g16970, alkenal/one reductase, ataor, at-aer, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
alkenal/one oxidoreductase
alkenal/one reductase
AOR
At5g16970
bifunctional LTB4 12-hydroxydehydrogenase/15-oxo-prostaglandin 13-reductase
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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
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-
-
-
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
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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
1-cyclohexene-1-carboxaldehyde + NADPH + H+
cyclohexanecarboxaldehyde + NADP+
-
-
-
?
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+
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2-[4-[(E)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid is also known as CS-670
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-
?
artemisinic aldehyde + NADPH + H+
dihydroartemisinic aldehyde + NADP+
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at 1.9% of the rate with 2E-nonenal
88% 11S- and 12% 11R-isomer
-
?
benzylidine acetone + NAD(P)H
? + NAD(P)+
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reduction of alpha,beta-double bond
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-
?
2E-hexenal + NADPH + H+
hexanal + NADP+
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at 12% of the rate with 2E-nonenal
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-
?
4-hydroxy-(2E)-nonenal + NAD(P)H
4-hydroxynonylaldehyde + NAD(P)+
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-
-
?
4-hydroxy-(2E)-nonenal + NAD(P)H
4-hydroxynonylaldehyde + NAD(P)+
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-
-
-
?
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
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-
?
irofulven + NADPH
?
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less cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
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-
?
n-alkanal + NAD(P)+
alk-2-enal + NAD(P)H
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carbon chain length C3-C9 serves as substrates
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-
?
additional information
?
-
-
catalyzes the hydrogenation of alpha,beta-unsaturated bonds, but not the reduction of the aldehyde moiety in 2-alkenal molecules
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-
?
additional information
?
-
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reduction of the alpha,beta-carbon-carbon double bond to a single bond, broad substrate specificity
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-
?
additional information
?
-
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reaction product identification by mass spectrometry
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-
?
additional information
?
-
-
regio- and stereochemistry of hydride transfer, overview
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-
?
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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
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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
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ordered Theorell-Chance kinetic mechanism, steady-state kinetics, detailed analysis, kinetic isotopic effects
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0.004
NADPH
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recombinant enzyme, pH 7.2, 25°C, with substrate trans-2-nonenal
0.032
NADPH
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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