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:
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 (36 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-4-coumaroyl-CoA + 2-oxoglutarate + O2 = 2,4-dihydroxycinnamoyl-CoA + succinate + CO2
show the reaction diagram
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trans-4-coumaroyl-CoA + NADPH + H+ = dihydro-4-coumaroyl-CoA + NADP+
show the reaction diagram
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coumaroyl-CoA + anthranilate = CoA + N-(4-hydroxycinnamoyl)-anthranilate
show the reaction diagram
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malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ = CoA + isoliquiritigenin + CO2 + NADP+ + H2O
show the reaction diagram
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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]
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2 4-coumaroyl-CoA + malonyl-CoA + H2O = 3 CoA + bisdemethoxycurcumin + 2 CO2
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4-coumaroyl-CoA + malonyl-CoA + H2O = 2 CoA + 4-hydroxybenzalacetone + 2 CO2
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4-coumaroyl-CoA + malonyl-CoA = (4-coumaroyl)acetyl-CoA + CO2 + CoA
show the reaction diagram
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4-coumaroyl-CoA + S-adenosyl-L-methionine = CoA + S-methyl-5'-thioadenosine + N-(4-coumaroyl)-L-homoserine lactone
show the reaction diagram
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2 4-coumaroyl-CoA + spermidine = 2 CoA + N1,N8-bis(4-coumaroyl)-spermidine
show the reaction diagram
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4-coumaroyl-CoA = 4-hydroxybenzaldehyde + acetyl-CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ATP + 4-coumarate + CoA = AMP + diphosphate + 4-coumaroyl-CoA
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (115 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
trans-4-coumaroyl-CoA + 2-oxoglutarate + O2 = 2,4-dihydroxycinnamoyl-CoA + succinate + CO2
show the reaction diagram
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trans-4-coumaroyl-CoA + 2-oxoglutarate + O2 = 2,4-dihydroxycinnamoyl-CoA + succinate + CO2
show the reaction diagram
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4-coumaroyl-CoA + 2 NADH + 2 oxidized ferredoxin iron-sulfur cluster = ? + 2 NAD+ + 2 reduced ferredoxin iron-sulfur cluster
show the reaction diagram
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trans-4-coumaroyl-CoA + NADPH + H+ = dihydro-4-coumaroyl-CoA + NADP+
show the reaction diagram
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4-coumaroyl-CoA + NADPH + CO2 + H+ = (2S)2-carboxy-3-(4-hydroxyphenyl)propionyl-CoA + NADP+
show the reaction diagram
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p-coumaroyl-CoA + tartronic acid = CoA + p-coumaroyltartronic acid
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p-coumaroyl-CoA + galactarate = CoA + O-p-coumaroylgalactarate
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p-coumaroyl-CoA + glucarate = CoA + p-coumaroylglucarate
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p-coumaroyl-CoA + glucarolactone = CoA + O-p-coumaroylglucarolactone
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coumaroyl-CoA + putrescine = CoA + N-coumaroylputrescine
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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
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malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ = CoA + isoliquiritigenin + CO2 + NADP+ + H2O
show the reaction diagram
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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
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p-coumaroyl-CoA + 16-hydroxypalmitic acid = CoA + (E)-16-(3-(4-hydroxyphenyl)acryloyloxy)hexadecanoic acid
show the reaction diagram
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4-coumaroyl-CoA + malonyl-CoA = (4-coumaroyl)acetyl-CoA + CO2 + CoA
show the reaction diagram
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4-coumaroyl-CoA + S-adenosyl-L-methionine = CoA + S-methyl-5'-thioadenosine + N-(4-coumaroyl)-L-homoserine lactone
show the reaction diagram
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2 4-coumaroyl-CoA + spermidine = 2 CoA + N1,N8-bis(4-coumaroyl)-spermidine
show the reaction diagram
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p-coumaroyl-CoA + H2O = p-coumaric acid + CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3,4-dihydroxyphenylpropanoyl-CoA + 4-coumarate = 3,4-dihydroxyphenylpropanoate + 4-coumaroyl-CoA
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ATP + 4-coumarate + CoA = AMP + diphosphate + 4-coumaroyl-CoA
show the reaction diagram
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ATP + trans-4-coumaric acid + CoA = AMP + diphosphate + trans-4-coumaroyl-CoA
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
severe substrate inhibition of 4-coumaroyl-CoA with 3-(4-hydroxyphenyl)lactate as acceptor and less with 3-(3,4-dihydroxyphenyl)lactate
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the presence of this substrate inhibits the enzyme reaction with feruloyl-CoA
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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) (36 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.0019
-
pH 50, 35°C
0.13
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pH 6.5, 30°C
3.4
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pH 7.3, 30°C, recombinant His6-tagged enzyme
2.3
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at 30°C

KM Value (115 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.097
-
pH 50, 35°C
0.055
-
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0.19
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with delphinidin 3,5-diglucoside as cosubstrate
0.0012
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pH 6.5, 30°C
0.0106
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pH 7.3, 30°C, recombinant His6-tagged enzyme
5.2
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References & Links

Links to other databases for 4-Coumaroyl-CoA

ChEBI
PubChem
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PubChem