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Information on EC 1.14.14.91 - trans-cinnamate 4-monooxygenase and Organism(s) Helianthus tuberosus and UniProt Accession Q04468

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IUBMB Comments
A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme is involved in flavonoid biosynthesis.
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This record set is specific for:
Helianthus tuberosus
UNIPROT: Q04468
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The taxonomic range for the selected organisms is: Helianthus tuberosus
The enzyme appears in selected viruses and cellular organisms
Synonyms
cinnamate 4-hydroxylase, cinnamic acid 4-hydroxylase, cinnamate-4-hydroxylase, cyp73a1, cyp73, trans-cinnamate 4-monooxygenase, cyp73a5, csc4h, trans-cinnamate 4-hydroxylase, trans-cinnamic acid 4-hydroxylase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
cinnamic acid 4-hydroxylase
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C4H
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-
-
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CA4H
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-
-
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CA4Hase
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-
-
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cinnamate 4-hydroxylase
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-
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cinnamate 4-monooxygenase
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-
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cinnamate hydroxylase
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-
-
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cinnamic 4-hydroxylase
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-
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cinnamic acid 4-hydroxylase
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-
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cinnamic acid 4-monooxygenase
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-
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cinnamic acid p-hydroxylase
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-
-
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CYP 73
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-
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Cytochrome P450 73
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cytochrome P450 cinnamate 4-hydroxylase
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hydroxylase, cinnamate 4-
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-
-
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oxygenase, cinnamate 4-mono-
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-
-
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P450C4H
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-
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t-cinnamic acid hydroxylase
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-
-
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trans-cinnamate 4-hydroxylase
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-
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trans-cinnamic acid 4-hydroxylase
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-
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
redox reaction
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-
-
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oxidation
-
-
-
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reduction
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-
-
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SYSTEMATIC NAME
IUBMB Comments
trans-cinnamate,[reduced NADPH-hemoprotein reductase]:oxygen oxidoreductase (4-hydroxylating)
A cytochrome P-450 (heme-thiolate) protein found in plants. The enzyme is involved in flavonoid biosynthesis.
CAS REGISTRY NUMBER
COMMENTARY hide
9077-75-2
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
trans-cinnamate + [reduced NADPH-hemoprotein reductase] + O2
4-hydroxycinnamate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
-
-
?
7-ethoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
-
demethylase
-
-
?
7-methoxycoumarin + [reduced NADPH-hemoprotein reductase] + O2
umbelliferone + ? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
demethylase
-
-
?
chlorotoluron + [reduced NADPH-hemoprotein reductase] + O2
?
show the reaction diagram
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methylhydroxylase activity
-
-
?
p-chloro-N-methylaniline + [reduced NADPH-hemoprotein reductase] + O2
p-chloroaniline + ? + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
N-demethylase activity
-
-
?
trans-cinnamate + [reduced NADPH-hemoprotein reductase] + O2
4-hydroxycinnamate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
trans-cinnamate + [reduced NADPH-hemoprotein reductase] + O2
4-hydroxycinnamate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome P450
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NADH
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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
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
8-methoxypsoralen
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1-aminobenzotriazole
2,4-dichloro-1-prop-2-ynyloxy-benzene
-
-
2-isopropyl-4-pentenamide
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NADP+
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competitive
phenoxy-1-propyne
-
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1
trans-cinnamate
pH 7.4
0.555
7-ethoxycoumarin
-
-
4
7-methoxycoumarin
-
-
0.013
NADPH
-
-
1.919
p-chloro-N-methylaniline
-
-
0.005
trans-cinnamate
-
-
additional information
additional information
-
-
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
129.1
trans-cinnamate
pH 7.4
0.0567
7-ethoxycoumarin
-
-
0.19
7-methoxycoumarin
-
-
0.000233
chlorotoluron
-
-
2.37
p-chloro-N-methylaniline
-
-
4.95
trans-cinnamate
-
-
additional information
additional information
-
-
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0048
8-methoxypsoralen
pH 7.4
0.0054
psoralen
pH 7.4
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
TCMO_HELTU
505
0
57920
Swiss-Prot
Secretory Pathway (Reliability: 2)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
57000
-
x * 57000, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
-
x * 57000, SDS-PAGE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expression in Saccharomyces cerevisiae
expression in Saccharomyces cerevisiae
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Beneviste, I.; Salaun, J.P.; Durst, F.
Wounding-induced cinnamic acid hydroxylase in Jerusalem artichoke tuber
Phytochemistry
16
69-73
1977
Helianthus tuberosus
-
Manually annotated by BRENDA team
Reichhart, D.; Simon, A.; Durst, F.
Autocatalytic inactivation of plant cytochrome P-450 enzymes: selective inactivation of cinnamic acid 4-hydroxylase from Helianthus tuberosus by 1-aminobenzotriazole
Arch. Biochem. Biophys.
216
522-529
1982
Helianthus tuberosus
Manually annotated by BRENDA team
Gabriac, B.; Werck-Reichhart, D.; Teutsch, H.; Durst, F.
Purification and immunocharacterization of a plant cytochrome P450: the cinnamic acid 4-hydroxylase
Arch. Biochem. Biophys.
288
302-309
1991
Helianthus tuberosus
Manually annotated by BRENDA team
Teutsch, H.G.; Hasenfratz, M.P.; Lesot, A.; Stoltz, C.; Garnier, J.M.; Jeltsch, J.M.; Durst, F.; Werck-Reichhart, D.
Isolation and sequence of a cDNA encoding the Jerusalem artichoke cinnamate 4-hydroxylase, a major plant cytochrome P450 involved in the general phenylpropanoid pathway
Proc. Natl. Acad. Sci. USA
90
4102-4106
1993
Helianthus tuberosus
Manually annotated by BRENDA team
Urban, P.; Werck-Reichhart, D.; Teutsch, H.G.; Durst, F.; Regnier, S.; Kazmaier, M.; Pompon, D.
Characterization of recombinant plant cinnamate 4-hydroxylase produced in yeast. Kinetic and spectral properties of the major plant P450 of the phenylpropanoid pathway
Eur. J. Biochem.
222
843-850
1994
Helianthus tuberosus
Manually annotated by BRENDA team
Pierrel, M.A.; Batard, Y.; Kazmaier, M.; Mignotte-Vieux, C.; Durst, F.; Werck-Reichhart, D.
Catalytic properties of the plant cytochrome P450 CYP73 expressed in yeast. Substrate specificity of a cinnamate hydroxylase
Eur. J. Biochem.
224
835-844
1994
Helianthus tuberosus
Manually annotated by BRENDA team
Gravot, A.; Larbat, R.; Hehn, A.; Lievre, K.; Gontier, E.; Goergen, J.L.; Bourgaud, F.
Cinnamic acid 4-hydroxylase mechanism-based inactivation by psoralen derivatives: cloning and characterization of a C4H from a psoralen producing plant-Ruta graveolens-exhibiting low sensitivity to psoralen inactivation
Arch. Biochem. Biophys.
422
71-80
2004
Helianthus tuberosus (Q04468), Petroselinum crispum (Q43033), Petroselinum crispum, Ruta graveolens (Q9AR74), Ruta graveolens
Manually annotated by BRENDA team