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Enzyme Nomenclature
Information on EC 1.3.1.16 - beta-nitroacrylate reductase
for references in articles please use BRENDA:EC1.3.1.16
Word Map on EC 1.3.1.16
- 1.3.1.16
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nitroalkenes
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electrophilic
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michael
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spectrometry-based
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nitro-fatty
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nitro-oleic
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beta-oxidation
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myocardial
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in-gel
- beta-mercaptoethanol
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bias
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unbiased
- 4-hydroxynonenal
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ischemia-reoxygenation
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amenable
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acid-protein
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.3.1.16
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RECOMMENDED NAME
GeneOntology No.
beta-nitroacrylate reductase
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
3-nitropropanoate + NADP+ = 3-nitroacrylate + NADPH + H+
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
oxidation
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redox reaction
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reduction
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SYSTEMATIC NAME
IUBMB Comments
3-nitropropanoate:NADP+ oxidoreductase
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CAS REGISTRY NUMBER
COMMENTARY
37255-28-0
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
physiological function
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overexpression of prostaglandin reductase-1 in HEK-293T cells promotes nitroalkene metabolism to inactive nitroalkanes, an effect that abrogates the Nrf2-dependent induction of heme oxygenase-1 expression by nitro-oleic acid
physiological function
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overexpression of prostaglandin reductase-1 in HEK-293T cells promotes nitroalkene metabolism to inactive nitroalkanes, an effect that abrogates the Nrf2-dependent induction of heme oxygenase-1 expression by nitro-oleic acid
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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
(Z)-3-phenyl-2-nitro-2-butene + NADPH
(2R,3R)-3-phenyl-2-nitrobutane + (2S,3R)-3-phenyl-2-nitrobutane + NADP+
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excellent enantioselectivity, moderate diastereoselectivity, mechanism
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-
?
10-nitrooctadec-9-enoic acid + NADPH + H+
10-nitrostearic acid + NADP+
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-
-
-
?
10-nitrooctadec-9-enoic acid + NADPH + H+
10-nitrostearic acid + NADP+
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-
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-
?
3-nitroacrylate + NADPH
3-nitropropanoate + NADP+
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highly specific
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-
?
3-nitroacrylate + NADPH
3-nitropropanoate + NADP+
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biosynthesis of beta-nitropropionic acid
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-
?
9-nitrooctandec-9-enoic acid + NADPH + H+
9-nitrostearic acid + NADP+
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?
additional information
?
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enzyme is specific for the reduction of the nitroalkene moiety, yielding saturated non-electrophilic products
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additional information
?
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no substrates are acrylic acid, crotonic acid, fumaric acid, cinnamic acid, 2-hydroxy-3-nitropropionic acid, shikimic acid, aconitic acid, itaconic acid, pyruvic acid, phosphoenolpyruvate, cytochrome c
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additional information
?
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enzyme is specific for the reduction of the nitroalkene moiety, yielding saturated non-electrophilic products
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NATURAL SUBSTRATES
NATURAL PRODUCTS
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
3-nitroacrylate + NADPH
3-nitropropanoate + NADP+
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biosynthesis of beta-nitropropionic acid
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?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
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enzyme is inhibited by sulfhydryl compounds, e.g. cysteine at concentrations equivalent to 3-nitroacrylic acid, inhibition probably due to the reaction of the sulfhydryl compounds with 3-nitroacrylic acid rather than an inhibition of the enzyme itself
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000085
(9E)-9-nitrooctadec-9-enoic acid
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pH 7.0, temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
81
(9E)-9-nitrooctadec-9-enoic acid
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pH 7.0, 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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pH RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
3 - 7
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at pH 3 about 35% of activity maximum, at pH 7 about 60% of activity maximum
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expression in HEK-293T cell
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LINKS TO OTHER DATABASES (specific for EC-Number 1.3.1.16)
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