Ligand 4-coumaroyl-CoA

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Basic Ligand Information

Molecular Structure
Picture of 4-coumaroyl-CoA (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C30H42N7O18P3S
4-coumaroyl-CoA
DMZOKBALNZWDKI-AZKRPDILSA-N
Synonyms:
(E)-4-coumaroyl-CoA, 4-coumaroylCoA, 4-coumaryl-CoA, 4-hydroxycinnamoyl-CoA, coumaroyl-CoA, p-Coumaroyl-CoA, trans-4-coumaroyl-CoA
Pathway Source
Pathways
MetaCyc
4-coumarate degradation (aerobic), 4-coumarate degradation (anaerobic), 4-hydroxybenzoate biosynthesis I (eukaryotes), 4-hydroxybenzoate biosynthesis III (plants), 6-gingerol analog biosynthesis (engineered) more


Show all pahtways known for Show all BRENDA pathways known for 4-coumaroyl-CoA

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (34 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
trans-4-coumaroyl-CoA + 2-oxoglutarate + O2 = 2,4-dihydroxycinnamoyl-CoA + succinate + CO2
-
show the reaction diagram
trans-4-coumaroyl-CoA + NADPH + H+ = dihydro-4-coumaroyl-CoA + NADP+
-
show the reaction diagram
coumaroyl-CoA + anthranilate = CoA + N-(4-hydroxycinnamoyl)-anthranilate
-
show the reaction diagram
malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ = CoA + isoliquiritigenin + CO2 + NADP+ + H2O
-
show the reaction diagram
4-coumaroyl-CoA + a flavonol 3-O-[beta-D-glucosyl-(1->2)-beta-D-glucosyl-(1->2)-beta-D-glucoside] = CoA + a flavonol 3-O-[6-(4-coumaroyl)-beta-D-glucosyl-(1->2)-beta-D-glucosyl-(1->2)-beta-D-glucoside]
-
show the reaction diagram
4-coumaroyl-CoA + malonyl-CoA + H2O = 2 CoA + 4-hydroxybenzalacetone + 2 CO2
-
show the reaction diagram
4-coumaroyl-CoA + malonyl-CoA = (4-coumaroyl)acetyl-CoA + CO2 + CoA
-
show the reaction diagram
4-coumaroyl-CoA + S-adenosyl-L-methionine = CoA + S-methyl-5'-thioadenosine + N-(4-coumaroyl)-L-homoserine lactone
-
show the reaction diagram
4-coumaroyl-CoA = 4-hydroxybenzaldehyde + acetyl-CoA
-

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

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
ATP + 4-coumarate + CoA = AMP + diphosphate + 4-coumaroyl-CoA
-

Substrate in Enzyme-catalyzed Reactions (128 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
trans-4-coumaroyl-CoA + 2-oxoglutarate + O2 = 2,4-dihydroxycinnamoyl-CoA + succinate + CO2
-
show the reaction diagram
trans-4-coumaroyl-CoA + 2-oxoglutarate + O2 = 2,4-dihydroxycinnamoyl-CoA + succinate + CO2
-
show the reaction diagram
4-coumaroyl-CoA + 2 NADH + 2 oxidized ferredoxin iron-sulfur cluster = ? + 2 NAD+ + 2 reduced ferredoxin iron-sulfur cluster
-
show the reaction diagram
trans-4-coumaroyl-CoA + NADPH + H+ = dihydro-4-coumaroyl-CoA + NADP+
-
show the reaction diagram
4-coumaroyl-CoA + NADPH + CO2 + H+ = (2S)2-carboxy-3-(4-hydroxyphenyl)propionyl-CoA + NADP+
-
show the reaction diagram
S-adenosyl-L-methionine + 4-coumaroyl-CoA = S-adenosyl-L-homocysteine + ?
-
show the reaction diagram
p-coumaroyl-CoA + tartronic acid = CoA + p-coumaroyltartronic acid
-
show the reaction diagram
4-coumaroyl-CoA + isocitrate = CoA + 4-coumaroylisocitrate
-
show the reaction diagram
p-coumaroyl-CoA + galactarate = CoA + O-p-coumaroylgalactarate
-
show the reaction diagram
p-coumaroyl-CoA + glucarate = CoA + p-coumaroylglucarate
-
show the reaction diagram
p-coumaroyl-CoA + glucarolactone = CoA + O-p-coumaroylglucarolactone
-
show the reaction diagram
2 malonyl-CoA + 4-coumaroyl-CoA = 3 CoA + 4-hydroxy-6-[(E)-2-(4-hydroxyphenyl)ethenyl]-2H-pyran-2-one + 2 CO2
-
show the reaction diagram
malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ = CoA + isoliquiritigenin + CO2 + NADP+ + H2O
-
show the reaction diagram
4-coumaroyl-CoA + a flavonol 3-O-[beta-D-glucosyl-(1->2)-beta-D-glucosyl-(1->2)-beta-D-glucoside] = CoA + a flavonol 3-O-[6-(4-coumaroyl)-beta-D-glucosyl-(1->2)-beta-D-glucosyl-(1->2)-beta-D-glucoside]
-
show the reaction diagram
p-coumaroyl-CoA + 16-hydroxypalmitic acid = CoA + (E)-16-(3-(4-hydroxyphenyl)acryloyloxy)hexadecanoic acid
-
show the reaction diagram
4-coumaroyl-CoA + malonyl-CoA = (4-coumaroyl)acetyl-CoA + CO2 + CoA
-
show the reaction diagram
4-coumaroyl-CoA + S-adenosyl-L-methionine = CoA + S-methyl-5'-thioadenosine + N-(4-coumaroyl)-L-homoserine lactone
-
show the reaction diagram
p-coumaroyl-CoA + H2O = p-coumaric acid + CoA
-

Product in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
3,4-dihydroxyphenylpropanoyl-CoA + 4-coumarate = 3,4-dihydroxyphenylpropanoate + 4-coumaroyl-CoA
-
-
show the reaction diagram
(R)-3-(4-hydroxyphenyl)lactoyl-CoA = (E)-4-coumaroyl-CoA + H2O
-
show the reaction diagram
ATP + 4-coumarate + CoA = AMP + diphosphate + 4-coumaroyl-CoA
-
-
show the reaction diagram
ATP + trans-4-coumaric acid + CoA = AMP + diphosphate + trans-4-coumaroyl-CoA
-

Inhibitor in Enzyme-catalyzed Reactions (6 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
50% inhibition at 0.5 mM
-
severe substrate inhibition of 4-coumaroyl-CoA with 3-(4-hydroxyphenyl)lactate as acceptor and less with 3-(3,4-dihydroxyphenyl)lactate
-
the presence of this substrate inhibits the enzyme reaction with feruloyl-CoA
-
above 0.01 mM
-
substrate inhibition above 0.03 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (47 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
-
1.63
-
recombinant isozyme CCR1, pH 6.0, 25°C
1.2
-
100 mM sodium/potassium phosphate buffer pH 6.3, 250 mM NADPH
pH 6.5, 30°C, wild-type enzyme
0.05
-
pH 6.5, 30°C, mutant Y154Y
8.42
-
pH 6.5, 30°C, mutant T154A
0.02
-
CCR1
0.43
-
pH 6.0, 40°C, recombinant His-tagged mutant F155Y
0.0142
-
in 100 mM phosphate buffer pH 6.5, at 30°C
105
-
pH 6.0, 40°C, recombinant His-tagged enzyme
0.0183
-
pH 6.0, 25°C, recombinant GST-tagged enzyme
0.0000265
-
pH 50, 35°C
0.0019
-
mutant enzyme V350A, pH and temperature not specified in the publication
0.0735
-
mutant enzyme V350G, pH and temperature not specified in the publication
0.109
-
pH 7.0, 30°C
pH 9.5, 35°C
0.01
-
pH 8.0, 30°C, recombinant wild-type enzyme
0.0298
-
at pH 9.5 and 50°C
0.011
-
pH 6.5, 30°C
0.13
-
pH 7.5, 37°C, CURS2
pH 8.0, 37°C, with cinnamoyl-diketide-N-acetylcysteaminyl-CoA
3.15
-
pH 7.3, 30°C, recombinant His6-tagged enzyme
3.4
-
pH 8.0, 30°C
0.0167
-
pH 9.5, 35°C
0.045
-
pH 7.0, 35°C, wild-type enzyme
0.042
-
pH 7.0, 37°C
wild type enzyme, at pH 8.0, temperature not specified in the publication
0.11
-
pH 7.0, 35°C, mutant enzyme L263M/F265Y/S338G
0.007
-
mutant enzyme R105Q, at pH 8.0, temperature not specified in the publication
0.178
-
mutant enzyme Q82P/C198F, at pH 8.0, temperature not specified in the publication
0.085
-
mutant enzyme Q82P, at pH 8.0, temperature not specified in the publication
0.05
-
in the presence of 0.001 mM chalcone isomerase-like protein CHIL, at pH 7.5 and 30°C
0.087
-
in the absence of chalcone isomerase-like protein CHIL, at pH 7.5 and 30°C
1.27
-
at pH 7.5 and 40°C
0.045
-
-
0.021
-
pH 4.0, 30°C, recombinant STS
-
0.02
-
cosubstrate quinate, pH not specified in the publication, 30°C
1.88
-
at 30°C
2.3
-

KM Value (128 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
100 mM sodium/potassium phosphate buffer pH 6.3, 250 mM NADPH
in 100 mM phosphate buffer pH 6.5, at 30°C
0.06
-
pH 6.0, 25°C, recombinant GST-tagged enzyme
0.0248
-
pH 6.0, 40°C, recombinant His-tagged mutant F155Y
0.01973
-
pH 6.0, 40°C, recombinant His-tagged wild-type enzyme
0.01595
-
pH 6.25, 37°C, recombinant His-tagged enzyme
0.377
-
pH 6.5, 30°C, mutant T154A
0.07
-
pH 6.5, 30°C, mutant Y154Y
0.113
-
pH 6.5, 30°C, wild-type enzyme
0.1
-
pH and temperature not specified in the publication
0.0028
-
recombinant isozyme CCR1, pH 6.0, 25°C
0.2086
-
pH 50, 35°C
0.097
-
mutant enzyme V350A, pH and temperature not specified in the publication
0.14
-
mutant enzyme V350G, pH and temperature not specified in the publication
0.2
-
+ tyramine
0.0067
-
30°C, pH 8.5, recombinant enzyme
0.02
-
pH 8.5, 30°C
0.0233
-
with phenethylamine, pH 7.5, 30°C, recombinant AAT1
0.3
-
with tryptamine, pH 7.5, 30°C, recombinant AAT1
0.157
-
with tyramine as acceptor
0.0037
-
with tyramine, pH 7.5, 30°C, recombinant AAT1
0.057
-
pH 6.5, 30°C
pH 7.0, 30°C, with 2,3-dihydroxybenzoate
0.0031
-
pH 7.0, 30°C, with 3-aminobenzoate
0.0185
-
pH 7.0, 30°C, with 3-hydroxyanthranilate
0.022
-
pH 7.0, 30°C, with 3-hydroxybenzoate
0.0015
-
pH 7.0, 30°C, with shikimate
0.0043
-
pH 7.5, 37°C, with glycerol
0.0601
-
pH 8.0, 37°C, recombinant GST-tagged enzyme, with quinate
0.00964
-
pH 8.0, 37°C, recombinant GST-tagged enzyme, with shikimate
0.00813
-
with quinate, pH 8.0, 37°C
9.64
-
with shikimate, pH 8.0, 37°C
8.13
-
-
0.02
-
pH 7.0, 30°C, with 3-(3,4-dihydroxyphenyl)lactate, native RAS
0.0013
-
pH 7.0, 30°C, with 3-(3,4-dihydroxyphenyl)lactate, recombinant RAS
0.0018
-
pH 7.0, 30°C, with 3-(4-hydroxyphenyl)lactate, native RAS
0.0047
-
pH 7.0, 30°C, with 3-(4-hydroxyphenyl)lactate, recombinant RAS
0.0092
-
pH 7.0, 30°C, with D-phenyllactate, recombinant RAS
0.0107
-
pH 7.0, 30°C, with D-tyrosine, recombinant RAS
0.0817
-
with 3-(3,4-dihydroxyphenyl)lactate, pH 7.0, 30°C, crude recombinant His-tagged enzyme
0.0032
-
with 3-(3,4-dihydroxyphenyl)lactate, pH 7.0, 30°C, native crude enzyme
0.0073
-
with 3-(4-hydroxyphenyl)lactate, pH 7.0, 30°C, crude recombinant His-tagged enzyme
0.0094
-
with 3-(4-hydroxyphenyl)lactate, pH 7.0, 30°C, native crude enzyme
0.0048
-
with 3-(4-hydroxyphenyl)lactate, pH 7.5, 30°C, recombinant AAT1
0.014
-
with shikimate, pH 7.5, 30°C, recombinant AAT1
0.083
-
isozyme PDSTS2
0.0053
-
isozyme PDSTS3
0.0009
-
with delphinidin 3,5-diglucoside as cosubstrate
0.19
-
pH 7.0, 30°C
at pH 9.5 and 50°C
0.01289
-
pH 7.5, 35°C
0.013
-
pH 8.0, 30°C
0.003
-
pH 8.0, 30°C, recombinant wild-type enzyme
0.01
-
pH 6.5, 30°C
0.0012
-
pH 7.5, 37°C, CURS2
pH 8.0, 37°C, with cinnamoyl-diketide-N-acetylcysteaminyl-CoA
0.085
-
pH 7.3, 30°C, recombinant His6-tagged enzyme
0.0106
-
pH 7, temperature not specified in the publication
0.16
-
isoenzyme 1
0.001
-
isoenzyme 2
0.0021
-
isoenzyme 3
0.0016
-
recombinant enzyme
0.0021
-
37°C, pH 7.2
0.048
-
at pH 7.5 and 40°C
0.01642
-
C169S/Q100E/K180Q triple mutant
0.0023
-
in the absence of chalcone isomerase-like protein CHIL, at pH 7.5 and 30°C
0.0497
-
in the presence of 0.001 mM chalcone isomerase-like protein CHIL, at pH 7.5 and 30°C
0.00473
-
isozyme AI
0.0008
-
isozyme AII
0.001
-
mutant enzyme Q82P, at pH 8.0, temperature not specified in the publication
0.0213
-
mutant enzyme Q82P/C198F, at pH 8.0, temperature not specified in the publication
0.0198
-
mutant enzyme R105Q, at pH 8.0, temperature not specified in the publication
0.0142
-
pH 7.0, 35°C, mutant enzyme L263M/F265Y/S338G
0.0078
-
pH 7.0, 35°C, wild-type enzyme
0.0049
-
pH 7.0, 37°C
0.0179
-
pH 7.5, 35°C
0.01642
-
pH 8.0, 30°C
0.00517
-
wild type enzyme, at pH 8.0, temperature not specified in the publication
0.0136
-
wild-type enzyme
0.0025
-
P375G mutant enzyme
0.016
-
pH 4.0, 30°C, recombinant STS
cosubstrate quinate, pH not specified in the publication, 30°C
0.519
-
pH 6.5, 30°C
pH 6.6, 30°C, cosubstrate: quinate
0.15
-
pH 6.6, 30°C, cosubstrate: shikimate
0.6
-
-
5.2
-

References & Links

Links to other databases for 4-coumaroyl-CoA

ChEBI
PubChem
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PubChem