Information on EC 1.1.1.195 - cinnamyl-alcohol dehydrogenase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.1.1.195
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RECOMMENDED NAME
GeneOntology No.
cinnamyl-alcohol dehydrogenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cinnamyl alcohol + NADP+ = cinnamaldehyde + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
phenylpropanoid biosynthesis
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Phenylpropanoid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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phenylpropanoid biosynthesis
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capsiconiate biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
cinnamyl-alcohol:NADP+ oxidoreductase
Acts on coniferyl alcohol, sinapyl alcohol, 4-coumaryl alcohol and cinnamyl alcohol (cf. EC 1.1.1.194 coniferyl-alcohol dehydrogenase).
CAS REGISTRY NUMBER
COMMENTARY hide
55467-36-2
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Abies nobilis
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Manually annotated by BRENDA team
A3 and A6
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Manually annotated by BRENDA team
M20 and M22
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Corylus sp.
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Eucalyptus sp.
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Manually annotated by BRENDA team
gene Fxcad1; cv. Chandler, octaploid cultivar, gene Fxcad1 and Fxcad2
SwissProt
Manually annotated by BRENDA team
var. Mandarin
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
gene Gold-hull-and-internode2, i.e. gene GH2
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Japanese black pine
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Pteris wimsetti
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Sphagnum sp.
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
strain PCC 6803
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
neoformed calli induced by Agrobacterium rhizogenes on Phaseolus mungo hypocotyl
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Manually annotated by BRENDA team
cv. Canary Bird
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Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
2,4-dimethylcinnamyl alcohol + NADP+
2,4-dimethylcinnamaldehyde + NADPH
show the reaction diagram
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2-propanol + NADP+
? + NADPH + H+
show the reaction diagram
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2-propanol can be also used in the cofactor recycling catalytic system as co-solvent like ethanol, but at the same time cinnamaldehyde conversion is lower (85%) and cinnamyl alcohol production is accordingly lower
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3,4-dimethoxycinnamyl alcohol + NADP+
3,4-dimethoxycinnamaldehyde + NADPH
show the reaction diagram
3,4-methylenedioxycinnamyl alcohol + NADP+
3,4-methylenedioxycinnamaldehyde + NADPH
show the reaction diagram
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-
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3-methoxybenzylalcohol + NADP+
3-methoxybenzaldehyde + NADPH
show the reaction diagram
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3-phenyl-1-propanol + NAD+
3-phenylpropanal + NADH + H+
show the reaction diagram
4-bromocinnamyl alcohol + NADP+
4-bromocinnamaldehyde + NADPH
show the reaction diagram
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4-chlorocinnamyl alcohol + NADP+
4-chlorocinnamaldehyde + NADPH
show the reaction diagram
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4-coumaraldehyde + NADPH + H+
4-coumaryl alcohol + NADP+
show the reaction diagram
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?
4-coumarylaldehyde + NADPH + H+
4-coumaryl alcohol + NADP+
show the reaction diagram
4-methoxybenzylalcohol + NADP+
4-methoxybenzaldehyde + NADPH
show the reaction diagram
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4-methoxycinnamyl alcohol + NADP+
4-methoxycinnamaldehyde + NADPH
show the reaction diagram
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4-methylcinnamyl alcohol + NADP+
4-methylcinnamaldehyde + NADPH
show the reaction diagram
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5-hydroxyconiferyl aldehyde + NADP+
5-hydroxyconiferyl alcohol + NADPH + H+
show the reaction diagram
very low activity
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?
5-hydroxyconiferyl aldehyde + NADPH
5-hydroxyconiferyl alcohol + NADP+
show the reaction diagram
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r
5-hydroxyconiferyl aldehyde + NADPH + H+
5-hydroxyconiferyl alcohol + NADP+
show the reaction diagram
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r
5-hydroxyconiferylaldehyde + NADP+
5-hydroxyconiferyl alcohol + NADPH + H+
show the reaction diagram
very low activity
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?
5-hydroxyconiferylaldehyde + NADPH + H+
5-hydroxyconiferyl alcohol + NADP+
show the reaction diagram
lowest catalytic efficiency
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?
allyl alcohol + NAD+
prop-2-enal + NADH + H+
show the reaction diagram
benzaldehyde + NADP+
benzoic acid + NADPH
show the reaction diagram
-
the enzyme also shows dismutase activity
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?
benzyl alcohol + NADP+
benzaldehyde + NADPH
show the reaction diagram
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r
benzyl alcohol + NADP+
benzaldehyde + NADPH + H+
show the reaction diagram
CAD4 displays slight activity for benzoyl alcohol
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?
benzyl alcohol + NADP+
benzylaldehyde + NADPH + H+
show the reaction diagram
slight activity
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r
benzylalcohol + NADP+
benzaldehyde + NADPH
show the reaction diagram
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butanol + NADP+
butyraldehyde + NADPH
show the reaction diagram
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r
caffeoyl aldehyde + NADPH + H+
caffeoyl alcohol + NADP+
show the reaction diagram
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r
caffeyl aldehyde + NADPH
caffeyl alcohol + NADP+
show the reaction diagram
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r
caffeylaldehyde + NADP+
caffeyl alcohol + NADPH + H+
show the reaction diagram
low activity
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?
caffeylaldehyde + NADPH + H+
caffeyl alcohol + NADP+
show the reaction diagram
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?
cinnamaldehyde + NADH + H+
cinnamyl alcohol + NAD+
show the reaction diagram
cinnamaldehyde + NADPH
cinnamyl alcohol + NADP+
show the reaction diagram
cinnamaldehyde + NADPH + H+
cinnamyl alcohol + NADP+
show the reaction diagram
cinnamyl alcohol + NAD+
cinnamaldehyde + NADH + H+
show the reaction diagram
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r
cinnamyl alcohol + NADP+
cinnamaldehyde + NADPH
show the reaction diagram
cinnamyl alcohol + NADP+
cinnamaldehyde + NADPH + H+
show the reaction diagram
cinnamyl alcohol + NADP+
cinnamyl aldehyde + NADPH
show the reaction diagram
cinnamyl alcohol + NADP+
cinnamyl aldehyde + NADPH + H+
show the reaction diagram
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?
cinnamyl aldehyde + NADPH
cinnamyl alcohol + NADP+
show the reaction diagram
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r
coniferaldehyde + NADPH + H+
coniferyl alcohol + NADP+
show the reaction diagram
coniferol + NADP+
coniferyl aldehyde + NADPH
show the reaction diagram
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?
coniferyl alcohol + NADP+
coniferyl aldehyde + NADPH + H+
show the reaction diagram
coniferyl alcohol and NADP+
coniferyl aldehyde + NADPH + H+
show the reaction diagram
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?
coniferyl aldehyde + NADPH
coniferol + NADP+
show the reaction diagram
coniferyl aldehyde + NADPH
coniferyl alcohol + NADP+
show the reaction diagram
coniferyl aldehyde + NADPH + H+
coniferyl alcohol + NADP+
show the reaction diagram
coumaryl alcohol + NADP+
coumaraldehyde + NADPH + H+
show the reaction diagram
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?
coumaryl alcohol + NADP+
coumaryl aldehyde + NADPH + H+
show the reaction diagram
coumaryl aldehyde + NADPH + H+
coumaryl alcohol + NADP+
show the reaction diagram
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r
ethanol + NADP+
acetaldehyde + NADPH + H+
show the reaction diagram
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r
p-coumaryl alcohol + NADP+
p-coumaraldehyde + NADPH
show the reaction diagram
p-coumaryl alcohol + NADP+
p-coumaryl aldehyde + NADPH + H+
show the reaction diagram
p-coumaryl aldehyde + NADPH + H+
p-coumaryl alcohol + NADP+
show the reaction diagram
p-coumarylaldehyde + NADPH + H+
p-coumaryl alcohol + NADP+
show the reaction diagram
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?
propanol + NADP+
propionaldehyde + NADPH
show the reaction diagram
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r
sinapaldehyde + NADPH + H+
sinapyl alcohol + NADP+
show the reaction diagram
sinapyl alcohol + NADP+
sinapaldehyde + NADPH
show the reaction diagram
sinapyl alcohol + NADP+
sinapyl aldehyde + NADPH + H+
show the reaction diagram
sinapyl aldehyde + NADPH + H+
sinapyl alcohol + NADP+
show the reaction diagram
sinapylaldehyde + NADPH + H+
sinapyl alcohol + NADP+
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
cinnamaldehyde + NADH + H+
cinnamyl alcohol + NAD+
show the reaction diagram
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r
cinnamaldehyde + NADPH
cinnamyl alcohol + NADP+
show the reaction diagram
cinnamaldehyde + NADPH + H+
cinnamyl alcohol + NADP+
show the reaction diagram
cinnamyl alcohol + NAD+
cinnamaldehyde + NADH + H+
show the reaction diagram
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r
cinnamyl alcohol + NADP+
cinnamaldehyde + NADPH + H+
show the reaction diagram
cinnamyl alcohol + NADP+
cinnamyl aldehyde + NADPH
show the reaction diagram
cinnamyl aldehyde + NADPH
cinnamyl alcohol + NADP+
show the reaction diagram
O49482, P48523
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r
coniferaldehyde + NADPH + H+
coniferyl alcohol + NADP+
show the reaction diagram
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isoform CAD3 has a higher binding preference with coniferaldehyde over sinapaldehyde, followed by isoforms CAD4, CAD2, and CAD1, respectively
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?
coniferol + NADP+
coniferyl aldehyde + NADPH
show the reaction diagram
Q02971
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?
coniferyl alcohol + NADP+
coniferyl aldehyde + NADPH + H+
show the reaction diagram
coniferyl aldehyde + NADPH
coniferyl alcohol + NADP+
show the reaction diagram
coniferyl aldehyde + NADPH + H+
coniferyl alcohol + NADP+
show the reaction diagram
p-coumaryl alcohol + NADP+
p-coumaryl aldehyde + NADPH + H+
show the reaction diagram
sinapaldehyde + NADPH + H+
sinapyl alcohol + NADP+
show the reaction diagram
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?
sinapyl alcohol + NADP+
sinapyl aldehyde + NADPH + H+
show the reaction diagram
sinapyl aldehyde + NADPH + H+
sinapyl alcohol + NADP+
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cu2+
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activates the enzyme activity in vivo by 45% after a 40 days treatment of roots with over 0.05 mM Cu2+
EDTA
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activates at 2.0 mM, Zn2+ treatment leads to the formation of a bigger oligomer of CAD which is catalytically inactive. EDTA treatment prevents the formation of the bigger CAD oligomer and hence increases the CAD activity
Mg2+
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30% activating at 2.0 mM
NaCl
activates 15% at 100 mM
additional information
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
inhibits 90% at 10 mM
adenosine 2',5'-diphosphate
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adenosine 5'-monophosphate
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IC50: 1.58 mM with NADP+ and 0.74 mM with NAD+
benzyl alcohol
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competitive mechanism, substrate inhibition
caffeic acid
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cinnamaldehyde
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substrate inhibition mediated by cinnamaldehyde concentrations far from the Km value of 0.46 mM, which does not allow for excessively increasing the starting cinnamaldehyde concentration, since the process yield may be greatly affected
cinnamyl alcohol
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competitive mechanism, substrate inhibition
coniferin
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with coniferyl alcohol as substrates, noncompetitive inhibition
coniferyl alcohol
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competitive mechanism, substrate inhibition
coniferyl aldehyde
competitve, a stronger inhibitor than sinapyl aldehyde; competitve, a stronger inhibtior than sinapyl aldehyde; competitve, a stronger inhibtior than sinapyl aldehyde
CTAB
inhibits 92% at 10 mM
diethyldicarbonate
60% inhibition at 1 mM
EDTA
inhibits 92% at 10 mM
Fe3+
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1 mM, 74% residual activity
ferulic acid
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flavones
Eucalyptus sp.
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IC50: 0.07-0.055 mM
Hg2+
strong inhibition
iodoacetic acid
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1 mM, 56% residual activity
Li+
strong inhibition
N-bromosuccimide
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1 mM, 56% residual activity
Ni
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CAD activity is not affected by concentrations up to 0.12 mM, phenolic metabolism is not substantially affected by Ni excess
Ni2+
strong inhibition
RNAi
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RNAi-mediated transient gene silencing in the epidermis leads to a higher penetration efficiency of Blumeria graminis f. sp. tritici (64%) than in the controls. Gene silencing also compromises penetration resistance to varying degrees with different genes against an inappropriate pathogen, Blumeria graminis f. sp. hordei. Co-silencing of CAD and other genes involved in monolignol biosynthesis leads to greater penetration of Blumeria graminis f. sp. tritici or Blumeria graminis f. sp. hordei than when the genes are silenced separately. Gene silencing hamperes host autofluorescence response at fungal contact sites
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SDS
inhibits 95% at 1%
sinapyl aldehyde
competitve, a weaker inhibitor than coniferyl aldehyde; competitve, a weaker inhibtior than coniferyl aldehyde; competitve, a weaker inhibtior than coniferyl aldehyde
Sucrose
10% inhibition at 20%
[[(2-hydroxyphenyl) amino]sulphinyl] acetic acid, 1.1 dimethyl ester
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
CO2
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high CO2 stimulates progressively the enzyme, as well as of other enzymes involved in metabolism of phenolic compounds, overview
DTT
activates 25% at 1 mM
jasmonate
accumulation of CAD mRNA in response to jasmonate application and mechanical wounding
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.036
3,4-dimethoxy-cinnamyl alcohol
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0.0069 - 0.043
3,4-dimethoxycinnamaldehyde
0.022
3,4-dimethoxycinnamyl alcohol
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0.106
3-Methoxybenzaldehyde
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-
0.96
3-Phenyl-1-propanol
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pH 8.0, 30°C
0.013 - 0.117
4-coumaraldehyde
0.0382 - 0.1122
4-coumarylaldehyde
-
0.13
4-methoxybenzaldehyde
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0.034
4-methoxycinnamyl alcohol
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0.0244
5-hydroxyconiferyl aldehyde
pH not specified in the publication, temperature not specified in the publication
0.09318 - 0.152
5-hydroxyconiferylaldehyde
-
0.04
acetaldehyde
-
pH 7.5, 37°C, recombinant enzyme
0.5
allyl alcohol
-
pH 8.0, 30°C
0.03 - 31
benzaldehyde
0.41 - 2.6
benzyl alcohol
9
butanol
-
pH 7.5, 37°C, recombinant enzyme
0.0891
caffeoyl aldehyde
pH not specified in the publication, temperature not specified in the publication
0.06592 - 0.09463
caffeylaldehyde
-
0.0015 - 0.92
cinnamaldehyde
0.0038 - 0.27
cinnamyl alcohol
0.005
cinnamyl aldehyde
-
pH 7.5, 37°C, recombinant enzyme
0.00077 - 0.1136
coniferaldehyde
0.00098 - 0.677
coniferyl alcohol
0.0018 - 0.146
coniferyl aldehyde
0.0042
coumaryl alcohol
pH not specified in the publication, temperature not specified in the publication
46
ethanol
-
pH 7.5, 37°C, recombinant enzyme
0.052 - 1.23
NAD+
0.016 - 0.071
NADH
0.0038 - 0.06
NADP+
0.0015 - 0.15
NADPH
0.0012 - 0.03
p-coumaraldehyde
0.034 - 0.283
p-coumaryl alcohol
0.0035 - 0.0272
p-coumaryl aldehyde
13
Propanol
-
pH 7.5, 37°C, recombinant enzyme
0.0043 - 0.2082
sinapaldehyde
0.0062 - 0.56
sinapyl alcohol
0.0028 - 1.969
sinapyl aldehyde
additional information
additional information
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