Information on EC 1.2.1.44 - cinnamoyl-CoA reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.2.1.44
-
RECOMMENDED NAME
GeneOntology No.
cinnamoyl-CoA reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
cinnamaldehyde + CoA + NADP+ = cinnamoyl-CoA + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
-
-
-
-
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
capsiconiate biosynthesis
-
-
phenylpropanoid biosynthesis
suberin monomers biosynthesis
-
-
Phenylpropanoid biosynthesis
-
-
Metabolic pathways
-
-
Biosynthesis of secondary metabolites
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-
SYSTEMATIC NAME
IUBMB Comments
cinnamaldehyde:NADP+ oxidoreductase (CoA-cinnamoylating)
Acts also on a number of substituted cinnamoyl esters of coenzyme A.
CAS REGISTRY NUMBER
COMMENTARY hide
59929-39-4
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
peanut
-
-
Manually annotated by BRENDA team
Betula platyphylla x Betula pendula
-
UniProt
Manually annotated by BRENDA team
swede root
-
-
Manually annotated by BRENDA team
Eucalyptus sp.
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Fragaria chiloensis x Fragaria virginiana, cv. Elsanta
UniProt
Manually annotated by BRENDA team
L. var. Mandarin, soybean
-
-
Manually annotated by BRENDA team
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Swissprot
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
Swissprot
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
cultivar Trichobel
UniProt
Manually annotated by BRENDA team
poplar
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
Swissprot
Manually annotated by BRENDA team
cv. Bluecrop
UniProt
Manually annotated by BRENDA team
L. cv. La Victoire, infected with Agrobacterium rhizogenes
-
-
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
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
show the reaction diagram
4-coumaroyl-CoA + NADPH + H+
4-coumaric aldehyde + CoA + NADP+
show the reaction diagram
-
-
-
?
4-coumaroyl-CoA + NADPH + H+
4-coumaroylaldehyde + CoA + NADP+
show the reaction diagram
5-hydroxyferuloyl-CoA + NADPH
5-hydroxyferulic aldehyde + CoA + NADP+
show the reaction diagram
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyconiferaldehyde + CoA + NADP+
show the reaction diagram
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyferulic aldehyde + CoA + NADP+
show the reaction diagram
A8DNN6
-
-
-
?
5-hydroxyferuloyl-CoA + NADPH + H+
? + CoA + NADP+
show the reaction diagram
-
-
-
r
caffeoyl-CoA + NADPH
caffeic aldehyde + CoA + NADP+
show the reaction diagram
caffeoyl-CoA + NADPH + H+
caffealdehyde + CoA + NADP+
show the reaction diagram
caffeoyl-CoA + NADPH + H+
caffeolylaldehyde + CoA + NADP+
show the reaction diagram
cinnamaldehyde + CoA + NADP+
cinnamoyl-CoA + NADPH + H+
show the reaction diagram
cinnamoyl-CoA + NADPH
cinnamaldehyde + CoA + NADP+
show the reaction diagram
cinnamoyl-CoA + NADPH + H+
cinnamaldehyde + CoA + NADP+
show the reaction diagram
coniferaldehyde + CoA + NADP+
feruloyl-CoA + NADPH + H+
show the reaction diagram
-
-
-
-
r
coumaroyl-CoA + NADPH + H+
coumaraldehyde + CoA + NADP+
show the reaction diagram
activity assay
-
-
?
coumaroyl-CoA + NADPH + H+
coumaric aldehyde + CoA + NADP+
show the reaction diagram
feruloyl-CoA + NADPH
ferulic aldehyde + CoA + NADP+
show the reaction diagram
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
show the reaction diagram
feruloyl-CoA + NADPH + H+
ferulic aldehyde + CoA + NADP+
show the reaction diagram
p-coumaroyl-CoA + NADPH
p-coumaric aldehyde + CoA + NADP+
show the reaction diagram
p-coumaroyl-CoA + NADPH + H+
p-coumaraldehyde + CoA + NADP+
show the reaction diagram
sinapaldehyde + CoA + NADP+
sinapoyl-CoA + NADPH + H+
show the reaction diagram
-
-
-
-
r
sinapoyl-CoA + NADPH
sinapic aldehyde + CoA + NADP+
show the reaction diagram
sinapoyl-CoA + NADPH + H+
sinapaldehyde + CoA + NADP+
show the reaction diagram
additional information
?
-
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
4-coumaroyl-CoA + NADPH + H+
4-coumaraldehyde + CoA + NADP+
show the reaction diagram
4-coumaroyl-CoA + NADPH + H+
4-coumaric aldehyde + CoA + NADP+
show the reaction diagram
Q08GL0
-
-
-
?
4-coumaroyl-CoA + NADPH + H+
4-coumaroylaldehyde + CoA + NADP+
show the reaction diagram
5-hydroxyferuloyl-CoA + NADPH + H+
5-hydroxyconiferaldehyde + CoA + NADP+
show the reaction diagram
5-hydroxyferuloyl-CoA + NADPH + H+
? + CoA + NADP+
show the reaction diagram
D2IX40, D2IX45
-
-
-
r
caffeoyl-CoA + NADPH + H+
caffealdehyde + CoA + NADP+
show the reaction diagram
caffeoyl-CoA + NADPH + H+
caffeolylaldehyde + CoA + NADP+
show the reaction diagram
cinnamaldehyde + CoA + NADP+
cinnamoyl-CoA + NADPH + H+
show the reaction diagram
cinnamoyl-CoA + NADPH + H+
cinnamaldehyde + CoA + NADP+
show the reaction diagram
coniferaldehyde + CoA + NADP+
feruloyl-CoA + NADPH + H+
show the reaction diagram
-
-
-
-
r
coumaroyl-CoA + NADPH + H+
coumaric aldehyde + CoA + NADP+
show the reaction diagram
feruloyl-CoA + NADPH + H+
coniferaldehyde + CoA + NADP+
show the reaction diagram
feruloyl-CoA + NADPH + H+
ferulic aldehyde + CoA + NADP+
show the reaction diagram
sinapaldehyde + CoA + NADP+
sinapoyl-CoA + NADPH + H+
show the reaction diagram
-
-
-
-
r
sinapoyl-CoA + NADPH + H+
sinapaldehyde + CoA + NADP+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
addition of Mg2+, Mn2+, Zn2+, Fe2+ has no effect
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,10-phenanthroline
-
-
4-chloromercuribenzoate
5-Hydroxyferuloyl-CoA
Ca2+
-
86% residual activity at 2 mM
caffeoyl-CoA
competitive inhibitor
citraconic anhydride
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31% residual activity at 1.5 mM with feruloyl-CoA as substrate
Co2+
-
42% residual activity at 2 mM
CoASH
-
product inhibition
Cs2+
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83% residual activity at 2 mM
Cu2+
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49% residual activity at 2 mM
Diethylpyrocarbonate
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44% residual activity at 3 mM with feruloyl-CoA as substrate
Fe2+
-
92% residual activity at 2 mM
Feruloyl-CoA
Hg2+
-
complete inhibition at 2 mM
iodoacetamide
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1 mM, 50% inhibition
Mg2+
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74% residual activity at 2 mM
Mn2+
-
21% residual activity at 2 mM
N-acetyl imidazole
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50% residual activity at 3 mM with feruloyl-CoA as substrate
N-ethylmaleimide
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-
NADP+
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product inhibition
Ni2+
-
25% residual activity at 2 mM
Phenylglyoxal
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47% residual activity at 1 mM with feruloyl-CoA as substrate
phenylmethylsulfonyl fluoride
-
60% residual activity at 1 mM with feruloyl-CoA as substrate
S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(3,4-dimethoxyphenyl)ethenyl]phosphonothioate
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S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]phosphonothioate
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S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phosphonothioate
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S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(4-hydroxyphenyl)ethenyl]phosphonothioate
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S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(4-methoxyphenyl)ethenyl]phosphonothioate
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SDS
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6% residual activity at 1% (v/v)
Sinapoyl-CoA
competitive inhibitor
Woodward's reagent K
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54% residual activity at 0.02 mM with feruloyl-CoA as substrate
Zn2+
-
45% residual activity at 2 mM
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
-
-
bovine serum albumin
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twofold increase of enzyme activity
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dithiothreitol
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OsRac1
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interaction with OsRac1, one of the Rac/Rop family of small GTPases, lead to the enzymatic activation of OsCCR1 in vitro
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sphingolipid elicitor
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induction of expression
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Triton X-100
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106% activity at 1% (v/v)
Tween 20
-
113% activity at 1% (v/v)
additional information
A8DNN6
CCR enzyme activity is increased progressively along with lignin biosynthesis and stem maturity. During stem development, CCR1 mRNA levels remain high at elongation, heading, and milky stages in the wheat H4564 cultivar. High CCR1 mRNA levels and high CCR enzyme activity in wheat stem are correlated with a higher Klason lignin content and greater stem mechanical strength in the H4564 cultivar. Escherichia coli BL21(DE3) and BL21(DE3)pLysS strains produce a much higher amount of CCR1 protein compared with the RIL and RP strains
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0028 - 0.377
4-Coumaroyl-CoA
0.0346 - 0.1824
5-Hydroxyferuloyl-CoA
0.00516 - 0.617
caffeoyl-CoA
0.9
cinnamoyl-CoA
-
-
0.031 - 0.05
coniferaldehyde
0.06
coumaroyl-CoA
-
in 100 mM phosphate buffer pH 6.5, at 30°C
0.00042 - 0.323
Feruloyl-CoA
0.0116 - 0.29
NADPH
0.00227 - 0.1
p-Coumaroyl-CoA
0.039 - 0.067
sinapaldehyde
0.00055 - 0.4
Sinapoyl-CoA
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0000265 - 8.42
4-Coumaroyl-CoA
4.9
5-Hydroxyferuloyl-CoA
-
0.0000293 - 113
caffeoyl-CoA
94 - 236
coniferaldehyde
0.43 - 105
coumaroyl-CoA
0.00234 - 164
Feruloyl-CoA
1.63
p-Coumaroyl-CoA
-
-
81 - 210
sinapaldehyde
0.013 - 131
Sinapoyl-CoA
kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00107 - 74.5
4-Coumaroyl-CoA
0.00115 - 2400
caffeoyl-CoA
1900 - 7500
coniferaldehyde
1700
coumaroyl-CoA
-
in 100 mM phosphate buffer pH 6.5, at 30°C
0.145 - 4600
Feruloyl-CoA
1200 - 5300
sinapaldehyde
1.56 - 2300
Sinapoyl-CoA
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0157
5-Hydroxyferuloyl-CoA
competitive inhibition of 5-hydroxyferuloyl-CoA on the feruloyl-CoA reaction
0.0153
caffeoyl-CoA
competitive inhibition of caffeoyl-CoA on the feruloyl-CoA reaction
0.0063 - 0.0083
Feruloyl-CoA
0.031 - 0.156
S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(3,4-dimethoxyphenyl)ethenyl]phosphonothioate
0.0071 - 0.055
S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(4-hydroxy-3,5-dimethoxyphenyl)ethenyl]phosphonothioate
0.0044 - 0.057
S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(4-hydroxy-3-methoxyphenyl)ethenyl]phosphonothioate
0.212 - 0.422
S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(4-hydroxyphenyl)ethenyl]phosphonothioate
0.068 - 0.29
S-[2-(acetylamino)ethyl] O-ethyl [(E)-2-(4-methoxyphenyl)ethenyl]phosphonothioate
0.02
Sinapoyl-CoA
competitive inhibition of sinapoyl-CoA on the feruloyl-CoA reaction
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.01
feruloyl-CoA as a substrate at pH 7.0
0.02
feruloyl-CoA as a substrate at pH 6.5
0.1
feruloyl-CoA as a substrate at pH 5.0
0.12
feruloyl-CoA as a substrate at pH 5.5
0.14
feruloyl-CoA as a substrate at pH 6.0
1.78
-
with feruloyl-CoA as substrate
16.2
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-
17.15
-
-
84.07
-
-
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.3 - 6.5
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-
6 - 6.2
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6.2
activity assay; activity assay
6.5
-
assay at
7.4 - 7.8
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-
7.5
-
forward reaction
7.8
-
reverse reaction
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
4 - 9
activity range, profile overview
5 - 8
activity range, profile overview
5 - 6.5
when the pH is above 6.5, the activity becomes negligible, feruloyl-CoA as substrate
5.4 - 8
-
pH 5.4: about 10% of activity maximum, pH 8.0: about 15% of activity maximum
5.5 - 6.9
activity range, inactive above pH 7.0, profile overview
additional information
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-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
10 - 60
activity range, profile overview, the enzyme is active even below 10°C
20 - 60
activity range, profile overview
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.47
sequence calculation
6.04
sequence calculation
6.1
calculated from amino acid sequence
6.27
sequence calculation
6.5
sequence calculation
8.22
sequence calculation
8.79
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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cambium sap, mainly from cambial and young xylem cells
Manually annotated by BRENDA team
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active lignifying tissue
Manually annotated by BRENDA team
low enzyme expression
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
33000
-
gel filtration
35700
x * 35700, calculated from amino acid sequence
36600
-
AtCCR2, predicted from gene sequence
36800
predicted molecular mass for CCR1 and CCR2; predicted molecular mass for CCR1 and CCR2
37000
-
determined by SDS-PAGE
37400
x * 37400, deduced from gene sequence
38700
-
1 * 38700, SDS-PAGE
39420
calculated molecular mass
40000
-
gel filtration
43000
A8DNN6
x * 43000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
additional information
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
lipoprotein
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