Information on EC 1.14.13.11 - trans-cinnamate 4-monooxygenase

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The expected taxonomic range for this enzyme is: Embryophyta

EC NUMBER
COMMENTARY hide
1.14.13.11
-
RECOMMENDED NAME
GeneOntology No.
trans-cinnamate 4-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
trans-cinnamate + NADPH + H+ + O2 = 4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
-
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of secondary metabolites
-
-
Flavonoid biosynthesis
-
-
Metabolic pathways
-
-
Phenylalanine metabolism
-
-
phenylpropanoid biosynthesis
-
-
Phenylpropanoid biosynthesis
-
-
phenylpropanoid biosynthesis, initial reactions
-
-
Stilbenoid, diarylheptanoid and gingerol biosynthesis
-
-
suberin monomers biosynthesis
-
-
Ubiquinone and other terpenoid-quinone biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
trans-cinnamate,NADPH:oxygen oxidoreductase (4-hydroxylating)
NADH also acts, more slowly. Involves a heme-thiolate protein (P-450).
CAS REGISTRY NUMBER
COMMENTARY hide
9077-75-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
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Uniprot
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
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SwissProt
Manually annotated by BRENDA team
-
SwissProt
Manually annotated by BRENDA team
L. cv. Galia
Uniprot
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
Petroselinum sp.
cv. Goldrich
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
Uniprot
Manually annotated by BRENDA team
gene SbC4H
UniProt
Manually annotated by BRENDA team
Sorghum sp.
Sorghum-Sudangrass hybrid
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
-
defects in cinnamate 4-hydroxylase lead to perturbation in phenylpropanoid metabolism
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
(2E)-3-(2,3-dimethoxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-2,3-dimethoxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-chlorophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(2-chloro-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-ethoxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(2-ethoxy-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-fluorophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(2-fluoro-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(2,4-dihydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-methoxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-2-methoxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-methylphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-2-methylphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(2-nitrophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-2-nitrophenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-chlorophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(3-chloro-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-fluorophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(3-fluoro-4-hydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-hydroxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-methoxyphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-methylphenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-3-methylphenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
(2E)-3-(3-nitrophenyl)prop-2-enoic acid + NADPH + H+ + O2
(2E)-3-(4-hydroxy-3-nitrophenyl)prop-2-enoic acid + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-chlorocinnamic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
2-fluorocinnamic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
3-hydroxycinnamic acid + NADPH + H+ + O2
? + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
7-ethoxycoumarin + O2 + NADPH
umbelliferone + ?
show the reaction diagram
-
demethylase
-
-
?
7-methoxycoumarin + O2 + NADPH
umbelliferone + ?
show the reaction diagram
-
demethylase
-
-
?
chlorotoluron + O2 + NADPH
?
show the reaction diagram
-
methylhydroxylase activity
-
-
-
p-chloro-N-methylaniline + O2 + NADPH
p-chloroaniline + ?
show the reaction diagram
-
N-demethylase activity
-
-
?
trans-cinnamate + NADH + H+ + O2
4-hydroxycinnamate + NAD+ + H2O
show the reaction diagram
-
reaction with NADH shows 50% of the activity with NADPH
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-coumaric acid + NADP+ + H2O
show the reaction diagram
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
trans-cinnamic acid + NADPH
?
show the reaction diagram
-
assay at 37C, pH 7.5, reaction stopped with HCl
-
-
?
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
trans-cinnamate + NADPH + H+ + O2
4-coumaric acid + NADP+ + H2O
show the reaction diagram
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
KCN
-
1 mM, increase to 125% of the activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,4-Naphthoquinone
Sorghum sp.
-
-
1-aminobenzotriazole
11-dodecynoic acid
-
slight
2,4-dichloro-1-prop-2-ynyloxy-benzene
-
-
2,4-Dinitrophenol
-
0.1 mM, 83% loss of activity
2-isopropyl-4-pentenamide
-
-
2-mercaptoethanol
-
2.0 mM
3-(2,4-dichlorophenoxy)-1-propyne
-
mechanism-based inhibitor
3-phenoxy-1-propyne
-
mechanism-based inhibitor
4-amino-5-(2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.005 mM
4-amino-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.0039 mM
4-amino-5-(3-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.036 mM
4-amino-5-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-(4-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-furan-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
4-amino-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.00032 mM
4-amino-5-pyridin-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.045 mM
4-amino-5-pyridin-3-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.051 mM
4-amino-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.013 mM
4-amino-5-thiophen-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.045 mM
8-methoxypsoralen
antimycin A
-
0.005 mM, 16% loss of activity
ascorbic acid
-
2.0 mM
benzoquinone
Sorghum sp.
-
-
chlorogenic acid
-
0.1 mM, 9% loss of activity
cis-cinnamate
Petroselinum sp.
-
competitive
CuSO4
-
1 mM, complete loss of activity
cytochrome c
-
hydroxylase activity with NADPH is strongly inhibited, activity with NADH is less susceptible
dithiothreitol
-
2.0 mM
EDTA
-
1 mM, 18% loss of activity
FAD
-
1 mM, 73% loss of activity
FMN
-
1 mM, 75% loss of activity
gallic acid
-
0.1 mM, 20% loss of activity
KCl
-
200 mM, 39% loss of activity. 500 mM, 69% loss of activity
KCN
-
10 mM, 21% loss of activity
menadione
MnCl2
-
1 mM, 27% loss of activity
NADP+
-
competitive
phenoxy-1-propyne
-
-
psoralen
Sodium azide
-
10 mM, 64% loss of activity
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
2-mercaptoethanol
-
0.1 mM, stimulates
ascorbic acid
-
0.1 mM, stimulates
dithiothreitol
-
0.1 mM, stimulates
glutathione
-
0.1 mM, stimulates
Lipid
Petroselinum sp.
-
lipid component required
S-methyl 1,2,3-benzothiadiazole-7-carbothioate
-
treatment of fruits
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0131
(2E)-3-(2-ethoxyphenyl)prop-2-enoic acid
0.0022
2-chlorocinnamic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0023
2-fluorocinnamic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0131
3-hydroxycinnamic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.555
7-ethoxycoumarin
-
-
4
7-methoxycoumarin
-
-
0.013 - 0.06
NADPH
0.021
O2
Sorghum sp.
-
-
1.919
p-chloro-N-methylaniline
-
-
0.0005 - 1
trans-cinnamate
additional information
additional information
-
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0567
7-ethoxycoumarin
Helianthus tuberosus
-
-
0.19
7-methoxycoumarin
Helianthus tuberosus
-
-
0.000233
chlorotoluron
Helianthus tuberosus
-
-
2.37
p-chloro-N-methylaniline
Helianthus tuberosus
-
-
1.72 - 161.8
trans-cinnamate
additional information
additional information
Helianthus tuberosus
-
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0048 - 0.0326
8-methoxypsoralen
0.34
cis-cinnamate
Petroselinum sp.
-
-
0.0054 - 0.00812
psoralen
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.1
4-amino-5-(2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: above 0.1 mM
0.005
4-amino-5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.005 mM
0.0039
4-amino-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.0039 mM
0.036
4-amino-5-(3-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.036 mM
0.1
4-amino-5-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
0.00032
4-amino-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.00032 mM
0.045
4-amino-5-pyridin-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.045 mM
0.051
4-amino-5-pyridin-3-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.051 mM
0.013
4-amino-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.013 mM
0.045
4-amino-5-thiophen-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
Populus sieboldii x Populus grandidentata
-
IC50: 0.045 mM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5 - 7
-
-
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.5 - 8.8
-
about 50% of maximal activity at pH 5.5 and at pH 8.8
6.3 - 8.2
-
50% of maximal activity at pH 6.3 and pH 8.2
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0 - 40
-
0C: 45% of maximal activity, 40C: 60% of maximal activity
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
BnC4H-1 and BvC4H-2 are co-dominantly expressed; BnC4H-1 and BvC4H-2 are co-dominantly expressed
Manually annotated by BRENDA team
relatively low expression level compared to roots
Manually annotated by BRENDA team
-
activity increases during aging of disks from very low initial values
Manually annotated by BRENDA team
-
specific to
Manually annotated by BRENDA team
BnC4H-1 and BvC4H-2 are co-dominantly expressed; BnC4H-1 and BvC4H-2 are co-dominantly expressed
Manually annotated by BRENDA team
BnC4H-1 is dominant over BnC4H-2; BnC4H-1 is dominant over BnC4H-2
Manually annotated by BRENDA team
BnC4H-1 and BvC4H-2 are co-dominantly expressed in young and middle-stage seed. In old seed, BnC4H-2 is dominant over BnC4H-1; BnC4H-1 and BvC4H-2 are co-dominantly expressed in young and middle-stage seed. In old seed, BnC4H-2 is dominant over BnC4H-1
Manually annotated by BRENDA team
additional information
-
lignifying tissue specific expression analysis, overview
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
endomembrane-bound, colocalization with L-Phe ammonia lyase
Manually annotated by BRENDA team
-
less than 5% of the activity
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
phosphoprotein
;
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20C or 4C, 0.1 M phosphate buffer, homogenate loses 2/3 of its activity in 24 h
-
1C, during first 8 days decrease of enzyme activity, with prolonged stroage time increase of enzyme activity
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
analysis of sequence variants (single nucleotide polymorphism)
cinnamate 4-hydroxylase and cinnamate 4-hydroxylase fused to the FLAG epitope expressed in yeast. A chimeric cinnamate 4-hydroxylase/green fluorescent protein gene is engineered and stable expressed in Arabidopsis
-
expressed in Escherichia coli
-
expressed in Saccharomyces cerevisiae
-
expressed in Saccharomyces cerevisiae strain WAT11
-
expressed in Saccharomyces strain INVSC2(CPR)
-
expressed in Saccharomyces strain INVSC2(CPR); expressed in Saccharomyces strain INVSC2(CPR); expressed in Saccharomyces strain INVSC2(CPR); expressed in Saccharomyces strain INVSC2(CPR)
expression in hairy roots using Agrobacterium rhizogenes-mediated transformation system
-
expression in microsomes of yeast strain INVSc1
-
expression in Saccharomyces cerevisiae
gene C4H, DNA and amino acid sequence determination and analysis, expression analysis by quantitative real-time PCR after elicitor treatment
-
gene SbC4H, DNA and amino acid sequence determination and analysis, quantitative transcription analysis by RT-PCR, sequence comparisons and phylogenetic tree
generation of transgenic tobacco lines with altered activity levels of cinnamic acid 4-hydroxylase by sense or antisense expression of an alfalafa cDNA
-
quantitative PCR C4H expression analysis in stone fruits and other lignifying tissues, and analysis of involved transcription factors, expression analysis, overview
-
quantitative real-time PCR expression analysis, sequence comparison and phylogenic tree
successful expression requires removal of the intron, yeast does not process the intron at all
-
the binary vector, renamed pBE:100F/101R, containing the coding region of tomato CYP73A24 in the sense orientation under the control of the CaMV35s promoter and nos terminator is transformed into tomato lines Moneymaker, a wild type line, and Old Gold Crimson, a natural high pigment line
-
transformation of Nicotiana tabacum with a truncated enzyme from Phaseolus vulgaris
-
translational fusion with P450 reductase in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
after methyl jasmonate treatment
-
expression is induced in early time points after wounding, i.e. 3-6 h. Upon salinity stress, enzyme is highly expressed for the periods of 3-6 h after treatment
methyl jasmonate induces the enzyme highest at 0.3 mM after 12 h treatment
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
A306T
-
naturally occuring mutation, characterization of a ref3 mutant: the mutant allele contains a single G-A transition, which results in a mis-sense mutation
G99E
-
naturally occuring mutation, characterization of a ref3 mutant: the mutant allele contains a single G-A transition, which results in a mis-sense mutation
R249K
-
naturally occuring mutation, characterization of a ref3 mutant: the mutant allele contains a single G-A transition, which results in a mis-sense mutation
additional information
-
C4H downregulation using RNAi, phenotype, overview