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
1.14.13.11
-
RECOMMENDED NAME
GeneOntology No.
trans-cinnamate 4-monooxygenase
REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
trans-cinnamate + NADPH + H+ + O2 = 4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
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).
SYNONYMS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
C4H
-
-
-
-
CA4H
-
-
-
-
CA4Hase
-
-
-
-
cinnamate 4-hydroxylase
-
-
-
-
cinnamate 4-monooxygenase
-
-
-
-
cinnamate hydroxylase
-
-
-
-
cinnamic 4-hydroxylase
-
-
-
-
cinnamic acid 4-hydroxylase
-
-
-
-
cinnamic acid 4-monooxygenase
-
-
-
-
cinnamic acid p-hydroxylase
-
-
-
-
CYP 73
-
-
-
-
Cytochrome P450 73
-
-
-
-
cytochrome P450 cinnamate 4-hydroxylase
-
-
-
-
hydroxylase, cinnamate 4-
-
-
-
-
oxygenase, cinnamate 4-mono-
-
-
-
-
P450C4H
-
-
-
-
t-cinnamic acid hydroxylase
-
-
-
-
trans-cinnamate 4-hydroxylase
-
-
-
-
trans-cinnamic acid 4-hydroxylase
-
-
-
-
CAS REGISTRY NUMBER
COMMENTARY
9077-75-2
-
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
Angelica gigas Nakai
-
UniProt
Manually annotated by BRENDA team
; recombinant
-
-
Manually annotated by BRENDA team
L. cv. Galia
Uniprot
Manually annotated by BRENDA team
cv. Venlo Pickling
-
-
Manually annotated by BRENDA team
L. cv.Wisconsin SMR-58
Uniprot
Manually annotated by BRENDA team
expressed by an optimized yeast system
-
-
Manually annotated by BRENDA team
transgenic plants expressing epitope-tagged version of the enzyme
-
-
Manually annotated by BRENDA team
Petroselinum sp.
-
-
-
Manually annotated by BRENDA team
Petroselinum sp.
Petroselinum crispum
-
-
Manually annotated by BRENDA team
Petroselinum sp.
Petroselinum hortense
-
-
Manually annotated by BRENDA team
L. cv. immuna
-
-
Manually annotated by BRENDA team
Populus trichocarpa * Populus deltoides
-
-
Manually annotated by BRENDA team
isozyme C4H1-1
TrEMBL
Manually annotated by BRENDA team
isozyme C4H1-2
TrEMBL
Manually annotated by BRENDA team
isozyme C4H2-1
TrEMBL
Manually annotated by BRENDA team
isozyme C4H2-2
TrEMBL
Manually annotated by BRENDA team
cv. Goldrich
UniProt
Manually annotated by BRENDA team
Sorghum sp.
Sorghum-Sudangrass hybrid
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
-
defects in cinnamate 4-hydroxylase lead to perturbation in phenylpropanoid metabolism
metabolism
Q3HM04
phenylpropanoid pathway
metabolism
-
cinnamate 4-hydroxylase is a key enzyme in the early phenylpropanoid pathway
metabolism
-
cinnamate 4-hydroxylase is an important enzyme in the phenylpropanoid pathway and also in the accumulation of decursin and decursinol angelate, which are major secondary metabolites in Angelica gigas
metabolism
E3T9X1
the enzyme is involved in the phenylpropanoid biosynthesis pathway
metabolism
-
the enzyme is involved in the phenylpropanoid pathway
physiological function
-
C4H controls the carbon flux for many phytoalexins that are synthesized when plants are challenged by pathogens
physiological function
-
cinnamic acid 4-hydroxylases isoforms C4H1 and C4H2 and a p-coumaroyl ester 3-hydroxylase C3H3 interact, forming heterodimeric C4H1/C4H2, C4H1/C3H3, and C4H2/C3H3 and heterotrimeric PtrC4H1/C4H2/C3H3 membrane protein complexes. Enzyme kinetics demonstrates that the enzymatic efficiency for any of the complexes is 70-6500 times greater than that of the individual proteins
physiological function
-
hairy roots overexpressing the enzyme produce increased amounts of decursinol angelate
physiological function
Angelica gigas Nakai
-
C4H controls the carbon flux for many phytoalexins that are synthesized when plants are challenged by pathogens
-
metabolism
Angelica gigas Nakai
-
cinnamate 4-hydroxylase is an important enzyme in the phenylpropanoid pathway and also in the accumulation of decursin and decursinol angelate, which are major secondary metabolites in Angelica gigas
-
additional information
-
downregulation of cinnamate 4-hydroxylase reduces Klason lignin content by 30% with no significant change in syringyl to guaiacyl ratio, effect on the wood ultrastructure and mechanical behavior, overview
additional information
-
expression patterns of flavonoid pathway genes involved in lignification of peach fruits, overview
SUBSTRATE
PRODUCT                      
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
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
-
-
?
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-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Q43033
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Q04468
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Q9AR74
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Q0Q5Z4, Q0Q5Z5, Q0Q5Z6, Q0Q5Z7
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
colocalization of L-phenylalanine ammonia-lyase and cinnamate 4-hydroxylase for metabolic channeling in phenylpropanoid biosynthesis
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme is involved in lignification
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme is involved in the biosynthesis of rosmarinic acid
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
first step in the formation of coumarin derivatives
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Q43033
key step in biosynthesis of phenylpropanoic compounds
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-coumaric acid + NADP+ + H2O
show the reaction diagram
E3T9X1
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-coumaric acid + NADP+ + H2O
show the reaction diagram
Angelica gigas, Angelica gigas Nakai
F4YRL2
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Sorghum sp.
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Petroselinum sp.
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Petroselinum sp.
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Petroselinum sp.
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
tetrahydrofolate required for reaction
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme of the phenylpropanoid pathway
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
the enzyme is regulated by the NADPH/NADP+ ratio
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
blue-light treatment of etiolated seedlings mediates a transient and concurrent increase in activity of cotyledons but not of hypocotyl
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme is stimulated by light
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Petroselinum sp.
-
enzyme catalyzes an important step in the biosynthesis of flavonoids, lignin and other plant phenolics
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
second enzyme of the phenylpropanoid pathway
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
second enzyme of the phenylpropanoid pathway
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme may function in lignification
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
the enzyme plays a central role in phenylpropanoid metabolism and lignin biosynthesis and possibly anchors a phenylpropanoid enzyme complex to the endoplasmic reticulum
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme catalyzes the first oxidative step of the phenylpropanoid pathway
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme is involved in the biosynthesis of lignin precursors
-
-
?
trans-cinnamic acid + NADPH
?
show the reaction diagram
-
assay at 37C, pH 7.5, reaction stopped with HCl
-
-
?
chlorotoluron + O2 + NADPH
?
show the reaction diagram
-
methylhydroxylase activity
-
-
-
additional information
?
-
A3FIN3
signaling components of defense/stress pathways, such as methyl jasmonate, abscisic acid, and ultraviolet-B radiation, up-regulate the SmC4H transcript levels over the control. Calcium chloride and hydrogen peroxide, have no significant effect on SmC4H expression
-
-
-
additional information
?
-
Q6DV44
the enzyme plays a critical role in catechins biosynthesis and a crosstalk between phenylpropanoid and flavonoid pathways
-
-
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
LITERATURE
(Substrate)
COMMENTARY
(Product)
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
colocalization of L-phenylalanine ammonia-lyase and cinnamate 4-hydroxylase for metabolic channeling in phenylpropanoid biosynthesis
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme is involved in lignification
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme is involved in the biosynthesis of rosmarinic acid
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
first step in the formation of coumarin derivatives
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Q43033
key step in biosynthesis of phenylpropanoic compounds
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-coumaric acid + NADP+ + H2O
show the reaction diagram
E3T9X1
-
-
-
?
trans-cinnamate + NADPH + H+ + O2
4-coumaric acid + NADP+ + H2O
show the reaction diagram
Angelica gigas, Angelica gigas Nakai
F4YRL2
-
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme of the phenylpropanoid pathway
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
the enzyme is regulated by the NADPH/NADP+ ratio
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
blue-light treatment of etiolated seedlings mediates a transient and concurrent increase in activity of cotyledons but not of hypocotyl
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme is stimulated by light
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
Petroselinum sp.
-
enzyme catalyzes an important step in the biosynthesis of flavonoids, lignin and other plant phenolics
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
second enzyme of the phenylpropanoid pathway
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
second enzyme of the phenylpropanoid pathway
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme may function in lignification
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
the enzyme plays a central role in phenylpropanoid metabolism and lignin biosynthesis and possibly anchors a phenylpropanoid enzyme complex to the endoplasmic reticulum
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme catalyzes the first oxidative step of the phenylpropanoid pathway
-
-
?
trans-cinnamate + NADPH + O2
4-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
enzyme is involved in the biosynthesis of lignin precursors
-
-
?
additional information
?
-
A3FIN3
signaling components of defense/stress pathways, such as methyl jasmonate, abscisic acid, and ultraviolet-B radiation, up-regulate the SmC4H transcript levels over the control. Calcium chloride and hydrogen peroxide, have no significant effect on SmC4H expression
-
-
-
additional information
?
-
Q6DV44
the enzyme plays a critical role in catechins biosynthesis and a crosstalk between phenylpropanoid and flavonoid pathways
-
-
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
cytochrome P450
Sorghum sp.
-
required
-
cytochrome P450
-
activity is dependent on NADPH:cytochrome P-450 reductase
-
cytochrome P450
-
involved in hydroxylation
-
cytochrome P450
-
electrons are transferred from NADPH, the preferential electron donor of the system, to cytochrome P-450 via NADPH-cytochrome P-450 reductase
-
cytochrome P450
-
-
-
cytochrome P450
-
-
-
cytochrome P450
-
cytochrome P450-dependent monooxygenase
-
cytochrome P450
-
-
-
cytochrome P450
-
-
-
NADH
-
NADH has a synergistic effect on NADPH-supported hydroxylation, at both nonsaturating, 0.1 mM, and near-saturating, 1 mM, concentrations of NADPH
NADH
-
NADH alone can not supply the enzyme with electrons. NADH, 0.5 mM, results in 51% stimulation when NADPH is present at a saturating level, 0.5 mM
NADH
-
50% of the activity with NADPH
NADPH
-
no activity with NADH
NADPH
Sorghum sp.
-
-
NADPH
-
-
NADPH
-
-
NADPH
-
NADH has a synergistic effect on NADPH-supported hydroxylation, at both nonsaturating, 0.1 mM, and near-saturating, 1 mM, concentrations of NADPH
NADPH
-
NADH alone can not supply the enzyme with electrons. NADH, 0.5 mM, results in 51% stimulation when NADPH is present at a saturating level, 0.5 mM
NADPH
-
-
NADPH
-
-
NADPH
-
-
NADPH
Petroselinum sp.
-
-
NADPH
Q43033
-
NADPH
Q9AR74
-
NADPH
-
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
KCN
-
1 mM, increase to 125% of the activity
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
1,4-Naphthoquinone
Sorghum sp.
-
-
1-aminobenzotriazole
-
autocatalytic inactivation
1-aminobenzotriazole
-
-
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
Q04468
-
8-methoxypsoralen
Q43033
-
8-methoxypsoralen
Q9AR74
-
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
Sorghum sp.
-
-
menadione
-
0.1 mM, 92% loss of activity
NADP+
-
competitive
phenoxy-1-propyne
-
-
psoralen
Q04468
-
psoralen
Q43033
-
psoralen
Q9AR74
irreversibly bound to the apoprotein. Inactivation is dependent on the presence of NADPH, time of pre-incubation, and inhibitor concentration
psoralen
-
-
Sodium azide
-
10 mM, 64% loss of activity
MnCl2
-
1 mM, 27% loss of activity
additional information
-
no inhibition by p-coumaric acid
-
additional information
-
a specific and reversible macromolecular inhibitor from dark-grown hypocotyl of Cucumis sativus
-
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
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
LITERATURE
IMAGE
0.0131
(2E)-3-(2-ethoxyphenyl)prop-2-enoic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0131
(2E)-3-(2-methoxyphenyl)prop-2-enoic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0131
(2E)-3-(2-methylphenyl)prop-2-enoic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
0.0131
(2E)-3-(2-nitrophenyl)prop-2-enoic acid
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C
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
-
-
0.013
NADPH
-
-
0.06
NADPH
-
-
0.021
O2
Sorghum sp.
-
-
1.919
p-chloro-N-methylaniline
-
-
0.0005
trans-Cinnamate
-
0.0005-0.04 mM substrate and 1 mM NADPH, at 30C; 30C
0.0023
trans-Cinnamate
Sorghum sp.
-
-
0.0025
trans-Cinnamate
-
-
0.0036
trans-Cinnamate
-
isoforms C4H1/C4H2/p-coumaroyl ester 3-hydroxylase C3H3 complex, pH 7.0, 20C
0.0037
trans-Cinnamate
-
isoforms C4H1/C4H2 complex, pH 7.0, 20C
0.0048
trans-Cinnamate
-
isoform C4H1/p-coumaroyl ester 3-hydroxylase C3H3 complex, pH 7.0, 20C
0.005
trans-Cinnamate
-
-
0.005
trans-Cinnamate
-
-
0.0059
trans-Cinnamate
-
isoform C4H2/p-coumaroyl ester 3-hydroxylase C3H3 complex, pH 7.0, 20C
0.007
trans-Cinnamate
-
isoform C4H1, pH 7.0, 20C
0.0089
trans-Cinnamate
-
-
0.04
trans-Cinnamate
-
isoform C4H2, pH 7.0, 20C
1
trans-Cinnamate
Q04468
pH 7.4
1
trans-Cinnamate
Q9AR74
pH 7.4
4
7-methoxycoumarin
-
-
additional information
additional information
-
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0567
7-ethoxycoumarin
-
-
0.19
7-methoxycoumarin
-
-
2.37
p-chloro-N-methylaniline
-
-
1.72
trans-Cinnamate
-
30C
4.95
trans-Cinnamate
-
-
129.1
trans-Cinnamate
Q04468
pH 7.4
161.8
trans-Cinnamate
Q9AR74
pH 7.4
0.000233
chlorotoluron
-
-
additional information
additional information
-
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.0048
8-methoxypsoralen
Q04468
pH 7.4
0.0142
8-methoxypsoralen
Q43033
pH 7.4
0.0326
8-methoxypsoralen
Q9AR74
pH 7.4
0.34
cis-cinnamate
Petroselinum sp.
-
-
0.0054
psoralen
Q04468
pH 7.4
0.0077
psoralen
Q9AR74
pH 7.4
0.00812
psoralen
Q43033
pH 7.4
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.1
4-amino-5-(2-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
0.005
4-amino-5-(3-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.005 mM
0.0039
4-amino-5-(3-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.0039 mM
0.036
4-amino-5-(3-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.036 mM
0.1
4-amino-5-(4-chlorophenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
0.1
4-amino-5-(4-hydroxyphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
0.1
4-amino-5-(4-methylphenyl)-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
0.1
4-amino-5-furan-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: above 0.1 mM
0.00032
4-amino-5-phenyl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.00032 mM
0.045
4-amino-5-pyridin-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.045 mM
0.051
4-amino-5-pyridin-3-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.051 mM
0.013
4-amino-5-pyridin-4-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.013 mM
0.045
4-amino-5-thiophen-2-yl-2,4-dihydro-3H-1,2,4-triazole-3-thione
-
IC50: 0.045 mM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
-
additional information
-
simple and sensitive assay method, based on the migration of tritium during the enzyme-catalyzed hydroxylation
additional information
-
55 U/mg protein, value about, 1 unit is defined as the amount of enzyme causing an increase in absorption, without any treatment, storage at 1C for 10 days; 70 U/mg protein, value about, 1 unit is defined as the amount of enzyme causing an increase in absorption, after treatment of fruits with benzo-thiadiaziole-7-carbothioic acid S-methyl ester, storage at 1C for 10 days
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
6.5 - 7
-
-
7.5
-
assay at
pH RANGE
ORGANISM
UNIPROT
COMMENTARY
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
LITERATURE
37
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0 - 40
-
0C: 45% of maximal activity, 40C: 60% of maximal activity
pI VALUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
9.1
A5GZU5, A5GZU7
calculated from sequence; calculated from sequence
9.1
F6K263
calculated
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
-
BnC4H-1 and BvC4H-2 are co-dominantly expressed
Manually annotated by BRENDA team
E3T9X1
relatively low expression level compared to roots
Manually annotated by BRENDA team
Petroselinum sp.
-
-
Manually annotated by BRENDA team
Angelica gigas Nakai
-
-
-
Manually annotated by BRENDA team
-
BnC4H-1 and BvC4H-2 are co-dominantly expressed
Manually annotated by BRENDA team
-
activity increases during aging of disks from very low initial values
Manually annotated by BRENDA team
-
highest expression level
Manually annotated by BRENDA team
Angelica gigas Nakai
-
highest expression level
-
Manually annotated by BRENDA team
-
BnC4H-1 and BvC4H-2 are co-dominantly expressed
Manually annotated by BRENDA team
-
gene expression is first detected in green fruit and is then remarkably reduced in yellow fruit, followed by an increase in red and black fruit. C4H gene in Korean black raspberry plays a role during color development at the late stages of fruit ripening, whereas the expression of C4H gene during the early stages may be related to the accumulation of flavanols
Manually annotated by BRENDA team
-
stone, spatial/temporal expression during fruit development, induction after day 43, overview
Manually annotated by BRENDA team
-
BnC4H-1 and BvC4H-2 are co-dominantly expressed
Manually annotated by BRENDA team
-
BnC4H-1 is dominant over BnC4H-2
Manually annotated by BRENDA team
A3FIN3
expression of SmC4H in the root or stem is much higher than in the leaf
Manually annotated by BRENDA team
Q17UC0
viral infections induce cinnamic acid 4-hydroxylase mRNA expression
Manually annotated by BRENDA team
-
BnC4H-1 is dominant over BnC4H-2
Manually annotated by BRENDA team
E3T9X1
highest expression level
Manually annotated by BRENDA team
-
BnC4H-2 is dominant over BnC4H-1
Manually annotated by BRENDA team
A3FIN3
expression of SmC4H in the root or stem is much higher than in the leaf
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
Manually annotated by BRENDA team
Sorghum sp.
-
-
Manually annotated by BRENDA team
-
BnC4H-1 and BvC4H-2 are co-dominantly expressed
Manually annotated by BRENDA team
A3FIN3
expression of SmC4H in the root or stem is much higher than in the leaf
Manually annotated by BRENDA team
-
developing, low expression level
Manually annotated by BRENDA team
-
highest level of activity
Manually annotated by BRENDA team
-
cell undergoing lignification
Manually annotated by BRENDA team
Q17UB9
viral infections induce cinnamic acid 4-hydroxylase mRNA expression
Manually annotated by BRENDA team
additional information
-
lignifying tissue specific expression analysis, overview
Manually annotated by BRENDA team
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
?
-
x * 57000, SDS-PAGE
?
-
x * 57000, SDS-PAGE
?
-
x * 58000, SDS-PAGE
?
-
x * 57730, calculated from sequence
?
F6K263
x * 57800, calculated
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
phosphoprotein
-
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
1C, during first 8 days decrease of enzyme activity, with prolonged stroage time increase of enzyme activity
-
-20C or 4C, 0.1 M phosphate buffer, homogenate loses 2/3 of its activity in 24 h
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
analysis of sequence variants (single nucleotide polymorphism)
-
quantitative real-time PCR expression analysis, sequence comparison and phylogenic tree
E3T9X1
expression in microsomes of yeast strain INVSc1
-
expression in hairy roots using Agrobacterium rhizogenes-mediated transformation system
-
gene C4H, DNA and amino acid sequence determination and analysis, expression analysis by quantitative real-time PCR after elicitor treatment
-
expressed in Escherichia coli
-
expressed in Saccharomyces cerevisiae strain WAT11
-
;
A5GZU5, A5GZU7
translational fusion with P450 reductase in Escherichia coli
-
expression in Saccharomyces cerevisiae
-
generation of transgenic tobacco lines with altered activity levels of cinnamic acid 4-hydroxylase by sense or antisense expression of an alfalafa cDNA
-
expression in Saccharomyces cerevisiae
Q43033
expression in Saccharomyces cerevisiae
Petroselinum sp.
-
successful expression requires removal of the intron, yeast does not process the intron at all
-
transformation of Nicotiana tabacum with a truncated enzyme from Phaseolus vulgaris
-
expressed in Saccharomyces cerevisiae
-
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 Saccharomyces strain INVSC2(CPR); expressed in Saccharomyces strain INVSC2(CPR); expressed in Saccharomyces strain INVSC2(CPR); expressed in Saccharomyces strain INVSC2(CPR)
Q0Q5Z4, Q0Q5Z5, Q0Q5Z6, Q0Q5Z7
expressed in Saccharomyces strain INVSC2(CPR)
-
quantitative PCR C4H expression analysis in stone fruits and other lignifying tissues, and analysis of involved transcription factors, expression analysis, overview
-
expression in Saccharomyces cerevisiae
Q9AR74
gene SbC4H, DNA and amino acid sequence determination and analysis, quantitative transcription analysis by RT-PCR, sequence comparisons and phylogenetic tree
E2F4D8
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
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
methyl jasmonate induces the enzyme highest at 0.3 mM after 12 h treatment
-
methyl jasmonate induces the enzyme highest at 0.3 mM after 12 h treatment
Angelica gigas Nakai
-
-
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
I3RMR5
after methyl jasmonate treatment
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
up
-
the enzyme is induced by pathogens, quantitative real-time PCR expression analysis after elicitor treatment, overview
up
Angelica gigas Nakai
-
the enzyme is induced by pathogens, quantitative real-time PCR expression analysis after elicitor treatment, overview
-
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