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Information on EC 1.3.1.27 - 2-hexadecenal reductase
for references in articles please use BRENDA:EC1.3.1.27
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EC Tree 1 Oxidoreductases
1.3 Acting on the CH-CH group of donors
1.3.1 With NAD+ or NADP+ as acceptor
1.3.1.27 2-hexadecenal reductase
IUBMB Comments
Specific for long chain 2-trans- and 2-cis-alkenals, with chain length optimum around 14 to 16 carbon atoms.
The enzyme appears in viruses and cellular organisms
showSynonyms
2-alkenal reductase, zmaer, nadph-dependent 2-alkenal reductase, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
2-alkenal reductase
-
-
-
-
hexadecanal: NADP+ oxidoreductase
-
-
-
-
reductase, 2-alkenal
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
hexadecanal + NADP+ = 2-trans-hexadecenal + NADPH + H+
-
-
-
-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
BRENDA
MetaCyc
sphingosine and sphingosine-1-phosphate metabolism
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SYSTEMATIC NAME
IUBMB Comments
hexadecanal:NADP+ DELTA2-oxidoreductase
Specific for long chain 2-trans- and 2-cis-alkenals, with chain length optimum around 14 to 16 carbon atoms.
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CAS REGISTRY NUMBER
COMMENTARY
52227-95-9
-
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
2-cis-hexadecenal + NADPH + H+
hexadecanal + NADP+
-
Substrates: -
Products: -
Products: -
r
2-trans,4-trans-hexadienal + NAD(P)H
4-trans-hexenal + NAD(P)+
-
Substrates: i.e. sorbaldehyde, low reaction rate
Products: -
Products: -
?
2-trans-octadecenal + NADPH
octdecanal + NADP+
-
Substrates: -
Products: -
Products: -
r
2-trans-tetradecenal + NADPH
tetradecanal + NADP+
-
Substrates: -
Products: -
Products: -
r
3-buten-2-one + NADPH + H+
butan-2-one + NADP+
Substrates: -
Products: -
Products: -
?
4-hydroxy-2-hexenal + NADPH + H+
4-hydroxyhexadecanal + NADP+
Substrates: -
Products: -
Products: -
?
4-hydroxy-2-nonenal + NADPH + H+
4-hydroxynonanal + NADP+
Substrates: -
Products: -
Products: -
?
cis-2-heptenal + NAD(P)H
heptanal + NAD(P)+
-
Substrates: -
Products: -
Products: -
?
cis-2-octenal + NAD(P)H
octanal + NAD(P)+
-
Substrates: best substrate
Products: -
Products: -
?
trans-2-butenal + NAD(P)H
butanal + NAD(P)+
-
Substrates: very low reaction rate
Products: -
Products: -
?
trans-2-cinnamaldehyde + NAD(P)H
cinnamaldehyde + NAD(P)+
-
Substrates: low reaction rate
Products: -
Products: -
?
trans-2-dodecenal + NAD(P)H
dodecanal + NAD(P)+
-
Substrates: low reaction rate
Products: -
Products: -
?
trans-2-heptenal + NAD(P)H
heptanal + NAD(P)+
-
Substrates: low reaction rate
Products: -
Products: -
?
trans-2-hexenal + NAD(P)H
hexanal + NAD(P)+
-
Substrates: low reaction rate
Products: -
Products: -
?
trans-2-nonenal + NAD(P)H + H+
nonanal + NAD(P)+
-
Substrates: low reaction rate
Products: -
Products: -
?
traumatin + NADPH + H+
12-oxododecanoic acid + NADP+
-
Substrates: i.e. (10E)-12-oxododec-10-enoic acid
Products: -
Products: -
?
additional information
?
-
Substrates: enzyme additionally catalyzes the reduction of quinones, reaction of EC 1.6.5.5. The enzyme shows a low level of activity with cinnamaldehyde and no activity with 2-cyclohexen-1-one and 15-ketoprostaglandin E2. No activity is detected with nonanal and 2-nonene
Products: -
Products: -
?
2-trans-hexadecenal + NADPH
hexadecanal + NADP+
-
Substrates: optimum chain length C14-C15
Products: -
Products: -
r
2-trans-hexadecenal + NADPH
hexadecanal + NADP+
-
Substrates: -
Products: -
Products: -
?
trans-2-decenal + NAD(P)H
decanal + NAD(P)+
-
Substrates: low reaction rate
Products: -
Products: -
?
trans-2-octenal + NAD(P)H
octanal + NAD(P)+
-
Substrates: -
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
flavin
-
enzyme is assumed to be a flavoprotein, prosthetic group may be FAD or FMN
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.48
2-nonenal
wild-type, pH 7.5, temperature not specified in the publication
0.035
3-buten-2-one
wild-type, pH 7.5, temperature not specified in the publication
0.55
4-hydroxy-2-nonenal
wild-type, pH 7.5, temperature not specified in the publication
0.13
4-hydroxy-2-hexenal
wild-type, pH 7.5, temperature not specified in the publication
1.26
4-hydroxy-2-hexenal
mutant Y59F, pH 7.5, temperature not specified in the publication
3.67
4-hydroxy-2-hexenal
mutant Y53F, pH 7.5, temperature not specified in the publication
0.005
NADPH
wild-type, pH 7.5, temperature not specified in the publication
0.015
NADPH
mutant Y59F, pH 7.5, temperature not specified in the publication
0.06
NADPH
mutant Y53F, pH 7.5, temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.113
2-nonenal
wild-type, pH 7.5, temperature not specified in the publication
0.167
3-buten-2-one
wild-type, pH 7.5, temperature not specified in the publication
1.33
4-hydroxy-2-hexenal
wild-type, pH 7.5, temperature not specified in the publication
1.15
4-hydroxy-2-nonenal
wild-type, pH 7.5, temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.23
2-nonenal
wild-type, pH 7.5, temperature not specified in the publication
4.8
3-buten-2-one
wild-type, pH 7.5, temperature not specified in the publication
2.1
4-hydroxy-2-nonenal
wild-type, pH 7.5, temperature not specified in the publication
0.02
4-hydroxy-2-hexenal
mutant Y53F, pH 7.5, temperature not specified in the publication
1.67
4-hydroxy-2-hexenal
mutant Y59F, pH 7.5, temperature not specified in the publication
10.2
4-hydroxy-2-hexenal
wild-type, pH 7.5, temperature not specified in the publication
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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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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
the enzyme significantly increases the tolerance of transgenic plants (OX-AER) to low nitrogen stress. Up-regulated ZmAER expression enhances the tolerance of maize to low nitrogen stress by alleviating oxidative stress and improving nutrient use efficiency
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). A0A2G9GE54_9LAMI
367
0
39910
TrEMBL
Mitochondrion (Reliability: 1)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
monomer
monomer
-
1 * 45000, predominant form, gel filtration after denaturation and reduction
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CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
to 1.85 A resolution. The overall structure displays the typical medium-chain dehydrogenase fold with two domains: the catalytic domain, residues 1-128 and 271-329, and the coenzyme-binding domain, residues 129-270, which are separated by a deep cleft that binds the cofactor NADP+ and the substrate
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Y53F
substrate-pocket residue, large increase in Km values for all substrates and the cofactor, but mainly towards 3-buten-2-one and propenal with a 30fold increase
Y59F
substrate-pocket residue, almost the same kinetic parameter values as the wild-type enzyme for 2-alkenals
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pH STABILITY
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
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APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
food industry
-
use of enzyme to improve beer quality by conversion of trans-2-nonenal, the major contributor to the cardboard-like taste of aged beer
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Miyamaura, N.; Matsui, H.; Tahara, S.; Mizutani, J.; Chiba, S.
Purification and some properties of 2-alkenal reductase of Muco griseo-cyanus AHU6044
Agric. Biol. Chem.
48
185-192
1984
Mucor circinelloides
-
brenda
Stoffel, W.; Därr, W.
Purification and characterization of 2-alkenal reductase
Hoppe-Seyler's Z. Physiol. Chem.
356
385-390
1975
Rattus norvegicus
brenda
Stoffel, W.; Därr, W.
2-alkenal reductase isolation, properties and specificities
Hoppe-Seyler's Z. Physiol. Chem.
355
54-60
1974
Rattus norvegicus
brenda
Stoffel, W.; Bauer, E.; Stahl, J.
The metabolism of sphingosine bases in Tetrahymena pyriformis. Sphingosine kinase and sphingosine-1-phosphate lyase
Hoppe-Seyler's Z. Physiol. Chem.
355
61-74
1974
Tetrahymena pyriformis
brenda
Hambraeus, G.; Nyberg, N.
Enzymatic hydrogenation of trans-2-nonenal in barley
J. Agric. Food Chem.
53
8714-8721
2005
Hordeum vulgare
brenda
Porte, S.; Moeini, A.; Reche, I.; Shafqat, N.; Oppermann, U.; Farres, J.; Pares, X.
Kinetic and structural evidence of the alkenal/one reductase specificity of human zeta-crystallin
Cell. Mol. Life Sci.
68
1065-1077
2011
Homo sapiens (Q08257)
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), Zea mays
brenda
EXTERNAL LINKS (specific for EC-Number 1.3.1.27)
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Release 2023.1 (January 2023)
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