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BRENDA support

Ligand coumaric acid

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Basic Ligand Information

Molecular Structure
Picture of coumaric acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
Molfile
C9H8O3
coumaric acid
PMOWTIHVNWZYFI-AATRIKPKSA-N
Synonyms:
(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid, (E)-2-hydroxycinnamic acid, (E)-o-hydroxycinnamate, 2-coumarate, 2-coumaric acid, 2-hydroxy-trans-cinnamate, 2-hydroxycinnamate, 2-hydroxycinnamic acid, 2-hydroxy cinnamic acid, cumaric acid, o-coumarate, o-coumaric acid, o-cumaric acid, o-hydroxy-trans-cinnamic acid, o-hydroxycinnamic acid, trans-2-hydroxycinnamate

Related pathways


Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-coumarate + NADH = melilotate + NAD+
show the reaction diagram
-
UDP-glucose + 2-hydroxycinnamate = UDP + (2E)-3-[2-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoic acid
show the reaction diagram
-
UDP-glucose + 2-coumarate = UDP + 2-coumaroyl beta-D-glucoside
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-cinnamate + NADPH + O2 = 2-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
o-coumaric acid + H2O2 = ?
show the reaction diagram
-
(2E)-3-(2-hydroxyphenyl)prop-2-enoic acid + [reduced NADPH-hemoprotein reductase] + O2 = (2E)-3-(2,4-dihydroxyphenyl)prop-2-enoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
o-coumaric acid + NADPH + ATP = 3-(2-hydroxyphenyl)-2-propen-1-al + NADP+ + AMP + H2O
show the reaction diagram
-
2-coumarate + NADH = melilotate + NAD+
show the reaction diagram
-
(E)-o-hydroxycinnamate + NADH = 3-(2-hydroxyphenyl)propionate + NAD+
show the reaction diagram
-
N6-(2-isopentenyl)adenine + o-coumaric acid = adenine + 3-methylbut-2-enal + ?
show the reaction diagram
-
UDP-glucose + 2-hydroxycinnamate = UDP + (2E)-3-[2-(beta-D-glucopyranosyloxy)phenyl]prop-2-enoic acid
show the reaction diagram
-
UDPglucose + o-hydroxycinnamic acid = UDP + o-hydroxycinnamoyl-beta-1-D-glucose
show the reaction diagram
-
UDP-glucose + 2-coumaric acid = UDP + ?
show the reaction diagram
-
UDP-glucose + 2-coumaric acid = UDP + 1-O-[2-coumaroyl]-beta-D-glucopyranose
show the reaction diagram
-
2-hydroxy-trans-cinnamate + NH3 = 2-hydroxy-L-phenylalanine
show the reaction diagram
-
2-hydroxy-trans-cinnamate + NH3 = 2-hydroxy-L-phenylalanine
show the reaction diagram
-
ATP + 2-coumarate + CoA = AMP + diphosphate + 2-coumaroyl-CoA
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-cinnamate + NADPH + O2 = 2-hydroxycinnamate + NADP+ + H2O
show the reaction diagram
-
4-coumaroylcholine + H2O = coumaric acid + choline
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activation of P-PST
-

Inhibitor in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
2 mM, 30% inhibition
-
competitively inhibits the enzyme by binding to the active site, have a protective effect against reactive oxygen species in cells, structure-function relationship, computational molecular docking, overview
-
enzyme activitiy of pectin lyase decreases significantly when 0.1 mg/l of coumaric acid is added
-
IC50 ketonase reaction 87.8 microM, pH 6.5, room temperatur, IC50 enolase reaction 175.7 microM, pH 6.2, room temperatur
-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.3
-
pH 6.5, recombinant enzyme

KM Value (4 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0173
-
-
0.8
-
pH 7.0, 30°C

Ki Value (6 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.2
-
-
0.7
-
-
0.032
-
pH 8.5, 55°C

IC50 Value (3 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
3.61
-
recombinant enzyme, pH 6.5, 50°C

References & Links

Links to other databases for coumaric acid

EXTERNAL LINKS