Information on EC 1.3.1.74 - 2-alkenal reductase [NAD(P)+]

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.3.1.74
-
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RECOMMENDED NAME
GeneOntology No.
2-alkenal reductase [NAD(P)+]
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a n-alkanal + NAD(P)+ = an alk-2-enal + NAD(P)H + H+
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
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 hide
137367-20-5
-
52227-95-9
-
57406-74-3
-
9032-20-6
-
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
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
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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
(+)-acylfulvene + NADPH
?
show the reaction diagram
-
-
-
-
?
(+)-hydroxymethylacylfulvene + NADPH
?
show the reaction diagram
-
-
-
-
?
(-)-acylfulvene + NADPH
?
show the reaction diagram
-
-
-
-
?
(-)-hydroxymethylacylfulvene + NADPH
?
show the reaction diagram
-
-
-
-
?
(2E),(6Z)-nonadienal + NADPH
?
show the reaction diagram
-
-
-
-
?
(2E)-4-hydroxynon-2-enal + NADPH + H+
4-hydroxynonanal + NADP+
show the reaction diagram
-
-
-
-
?
(2E)-hexenal + NAD(P)H
n-hexanal + NAD(P)+
show the reaction diagram
-
-
-
?
(2E)-nonenal + NAD(P)H
n-nonanal + NAD(P)+
show the reaction diagram
-
-
-
-
?
(2E)-pentenal + NAD(P)H
n-pentanal + NAD(P)+
show the reaction diagram
-
-
-
-
?
1-penten-3-one + NADH
? + NAD+
show the reaction diagram
1-penten-3-one + NADH
pentan-3-one + NAD+
show the reaction diagram
-
-
-
?
1-penten-3-one + NADPH
? + NADP+
show the reaction diagram
-
-
-
?
1-penten-3-one + NADPH
pentan-3-one + NADP+
show the reaction diagram
13-oxo-(9E,11Z)-octadecadienoic acid + NADPH
?
show the reaction diagram
-
-
-
-
?
15-deoxy-DELTA12,14-prostaglandin + NADPH
?
show the reaction diagram
-
-
-
-
?
15-oxoprostaglandin E1 + NAD(P)H
? + NAD(P)+
show the reaction diagram
-
-
-
-
?
2-[4-[(E)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid + NADPH
2-[4-[(2-oxocyclohexyl)methyl]phenyl]propanoic acid + NADP+
show the reaction diagram
-
2-[4-[(E)-(2-oxocyclohexylidene)methyl]phenyl]propanoic acid is also known as CS-670
-
-
?
2E-hexenal + NADPH + H+
hexanal + NADP+
show the reaction diagram
-
at 12% of the rate with 2E-nonenal
-
-
?
2E-nonenal + NADPH + H+
nonanal + NADP+
show the reaction diagram
-
-
-
-
?
3-buten-2-one + NAD(P)H
2-butanone + NAD(P)+
show the reaction diagram
-
-
-
-
?
3-buten-2-one + NADH
2-butanone + NAD+
show the reaction diagram
3-buten-2-one + NADPH
2-butanone + NADP+
show the reaction diagram
3-nonen-2-one + NADPH
nonan-2-one
show the reaction diagram
-
-
-
-
?
3-penten-2-one + NAD(P)H
2-pentanone + NAD(P)+
show the reaction diagram
-
-
-
-
?
3-penten-2-one + NADH
2-pentanone + NAD+
show the reaction diagram
-
-
-
?
3-penten-2-one + NADPH
2-pentanone + NADP+
show the reaction diagram
-
-
-
?
4-hexen-3-one + NADH
hexan-3-one + NAD+
show the reaction diagram
4-hexen-3-one + NADPH
hexan-3-one + NADP+
show the reaction diagram
4-hydroxy-(2E)-hexenal + NAD(P)H
4-hydroxyhexenal + NAD(P)+
show the reaction diagram
-
-
-
-
?
4-hydroxy-(2E)-nonenal + NAD(P)H
4-hydroxynonylaldehyde + NAD(P)+
show the reaction diagram
4-hydroxy-(2E)-nonenal + NADPH + H+
4-hydroxynonanal + NADP+
show the reaction diagram
-
-
-
-
?
4-oxo-(2E)-nonenal + NADPH + H+
4-oxononanal + NADPH
show the reaction diagram
-
-
-
-
?
9-oxo-(10E,12Z)-octadecadienoic acid + NADPH
?
show the reaction diagram
-
-
-
-
?
artemisinic aldehyde + NADPH + H+
dihydroartemisinic aldehyde + NADP+
show the reaction diagram
-
at 1.9% of the rate with 2E-nonenal
88% 11S- and 12% 11R-isomer
-
?
benzylidine acetone + NAD(P)H
? + NAD(P)+
show the reaction diagram
-
reduction of alpha,beta-double bond
-
-
?
crotonaldehyde + NADH
butanal + NAD+
show the reaction diagram
crotonaldehyde + NADPH
butanal + NADP+
show the reaction diagram
diamide + NAD(P)H
? + NAD(P)+
show the reaction diagram
-
-
-
-
?
ethyl vinyl ketone + NAD(P)H
diethylketone + NAD(P)+
show the reaction diagram
-
-
-
-
?
illudin M + NADPH
?
show the reaction diagram
illudin S + NADPH
?
show the reaction diagram
irofulven + NADPH
?
show the reaction diagram
methyl vinyl ketone + NAD(P)H
dimethylketone + NAD(P)+
show the reaction diagram
-
-
-
-
?
n-alkanal + NAD(P)+
alk-2-enal + NAD(P)H
show the reaction diagram
propenal + NAD(P)H
propanal + NAD(P)+
show the reaction diagram
propenal + NADH
propanal + NAD+
show the reaction diagram
propenal + NADPH
propanal + NADP+
show the reaction diagram
trans,trans-2,4-alkadienal + NAD(P)H
? + NAD(P)+
show the reaction diagram
-
-
-
-
?
trans-2-alkenal + NAD(P)H
alkanal + NAD(P)+
show the reaction diagram
-
-
-
-
?
trans-2-nonenal + NAD(P)H
nonanal + NAD(P)+
show the reaction diagram
-
-
-
-
?
trans-2-pentenal + NADPH
pentanal + NADP+
show the reaction diagram
-
-
-
-
?
trans-3-nonen-2-one + NAD(P)H
2-nonanone + NAD(P)+
show the reaction diagram
-
-
-
-
?
trans-4-hydroxy-2-alkenal + NAD(P)H
4-hydroxyalkanal + NAD(P)+
show the reaction diagram
-
-
-
-
?
additional information
?
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
illudin M + NADPH
?
show the reaction diagram
-
extremly cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
illudin S + NADPH
?
show the reaction diagram
-
extremly cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
irofulven + NADPH
?
show the reaction diagram
-
less cytotoxic chemotherapeutic agent in cancer therapy, rapid metabolization by the enzyme
-
-
?
n-alkanal + NAD(P)+
alk-2-enal + NAD(P)H
show the reaction diagram
additional information
?
-
-
phase2/antioxidative enzyme
-
-
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
additional information
-
no cofactor: NADH
-
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Ca2+
-
stimulates activity
K+
-
stimulates activity
Li+
-
stimulates activity
Mg2+
-
stimulates activity
Mn2+
-
stimulates activity
Na+
-
stimulates activity
additional information
-
enzyme contains no Zn2+
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
15-keto prostaglandin F2alpha
-
43.06% residual activity at 0.1 mM
2-nonanone
-
product inhibition, competitive versus trans-3-nonen-2-one
benzylidene acetophenone
-
21.09% residual activity at 0.5 mM
cyclovalone
-
-
dicoumarol
-
11.45% residual activity at 0.1 mM
illudin M
-
-
illudin S
-
-
indomethacin
-
14.22% residual activity at 0.1 mM
irofulven
-
recombinant human 293 cells show 100fold increased sensitivity compared to the wild-type human 293 cells
NADP+
-
product inhibition, competitive versus NADPH
progesterone
-
-
quercetin
-
-
quercitrin
-
13.14% residual activity at 0.1 mM
additional information
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ammonium sulfate
-
stimulates activity
CH3COO- NH4+
-
stimulates activity
CH3COONa
-
stimulates activity
estradiol
-
the transcription of 2AER is estradiol-induced and correlates with conditional salt tolerance
Na2S2O5
-
stimulates activity
Na2SO4
-
stimulates activity
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
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
0.15
acrolein
-
30°C
0.071
artemisinic aldehyde
-
pH 7.0, 30°C
1.8 - 29.8
crotonaldehyde
0.128
Diamide
-
pH 6
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
0.053 - 4.64
NADH
0.004 - 0.185
NADPH
3.5 - 13.6
propenal
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
-
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1.05
(2E)-hexenal
-
pH 6
0.85
(2E)-nonenal
-
pH 6
-
0.583
(2E)-pentenal
-
pH 6
33.9
(2E,6Z)-nonadienal
-
pH 6.0
4 - 61
1-penten-3-one
1.1
13-oxo-(9E,11Z)-octadecadienoic acid
-
pH 6.0
0.308
15-deoxy-DELTA12,14-prostaglandin J2
-
pH 7.2
40
15-oxoprostaglandin E1
-
30°C
1.38 - 74
3-buten-2-one
18.9
3-nonen-2-one
-
pH 6.0
1.72 - 22
3-penten-2-one
3.3 - 68
4-hexen-3-one
0.7
4-hydroxy-(2E)-hexenal
-
pH 6
1.47 - 88.1
4-hydroxy-(2E)-nonenal
66.7
4-hydroxy-2-nonenal
-
30°C
20.1
4-oxo-(2E)-nonenal
-
pH 6.0
0.94
9-oxo-(10E,12Z)-octadecadienoic acid
-
pH 6.0
3.67
acrolein
-
30°C
1.3 - 42
crotonaldehyde
1.58
Diamide
-
pH 6
160
ethyl vinyl ketone
-
30°C
23 - 75
NADH
23 - 75
NADPH
0.667 - 63
propenal
0.97 - 16.83
trans-2-pentenal
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
13.8 - 105
1-penten-3-one
25.7 - 26.9
3-buten-2-one
34.9
3-penten-2-one
pH 7.0, 25°C; pH 7.0, 25°C
27.5 - 2960
4-hexen-3-one
16.2 - 434
NADH
406 - 2300
NADPH
4.63 - 6.28
propenal
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
-
product inhibition kinetics
-
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0054
-
cytosol extract
0.275
-
purified recombinant enzyme, substrate irofulven
0.803
-
after 150fold purification
44.1
-
purified recombinant enzyme, substrate illudin M
115.9
-
purified recombinant enzyme, substrate illudin S
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.2
-
assay at
7.4
-
assay at
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pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.3 - 6.6
-
50% activity at pH 5.3 and pH 6.6
additional information
-
pH-profile
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
assay at
30
-
assay at
37
-
assay at
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
developed silique
Manually annotated by BRENDA team
additional information
-
Dbr1 expression is readily detectable in aerial parts of the plant, but not in the roots
Manually annotated by BRENDA team
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
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
Manually annotated by BRENDA team
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
35000
-
SDS-PAGE
38500
-
x * 38500, calculated
45000
-
2 * 45000, SDS-PAGE, enzyme can form dimeric and trimeric aggretates; 3 * 45000, SDS-PAGE, enzyme can form dimeric and trimeric aggretates
90000
-
dimeric form, gel filtration
135000
-
trimeric form, gel filtration
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 38500, calculated
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
-80°C, no loss of activity for 8 months
-
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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
recombinant
-
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
expressed in Escherichia coli Top10 cells
-
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
-
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
-
in transgenic tobaccos that overexpress the AER gene
-
overexpressed in Escherichia coli as a GST-fusion protein
-
overexpressed in Escherichia coli as a GST-fusion protein; 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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Show AA Sequence (1813 entries)
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LINKS TO OTHER DATABASES (specific for EC-Number 1.3.1.74)
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KEGG
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NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
InterPro (database of protein families, domains and functional sites)