Ligand ferulic acid

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Basic Ligand Information

Molecular Structure
Picture of ferulic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H10O4
ferulic acid
KSEBMYQBYZTDHS-HWKANZROSA-N
Synonyms:
(2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid, 3-methoxy-4-hydroxy-trans-cinnamate, 3-methoxy-4-hydroxycinnamic acid, 3-O-methylcaffeic acid, 4-hydroxy-3-methoxy-trans-cinnamic acid, 4-hydroxy-3-methoxycinnamate, 4-hydroxy-3-methoxy cinnamic acid, 4-hydroxy-3-methoxycinnamic acid, coniferic acid, coniferylic acid, ferrulic acid, ferulate, feruloate, trans-ferulate, trans-ferulic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ferulate = 4-vinylguaiacol + CO2
show the reaction diagram
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ferulic acid + CoASH + ATP = trans-feruloyl-CoA + products of ATP breakdown
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (160 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
coniferyl aldehyde + H2O + NAD+ = ferulate + NADH
show the reaction diagram
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S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ferulic acid
show the reaction diagram
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S-adenosyl-L-methionine + 3,4-dihydroxy-trans-cinnamate = S-adenosyl-L-homocysteine + 3-methoxy-4-hydroxy-trans-cinnamate
show the reaction diagram
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N-feruloylglycine + H2O = ferulate + glycine
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (81 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ferulic acid + O2 = ?
show the reaction diagram
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ferulic acid + FADH2 + O2 = 5-hydroxyferulic acid + FAD + H2O
show the reaction diagram
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ferulate + [reduced NADPH-hemoprotein reductase] + O2 = 5-hydroxyferulate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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UDP-glucose + ferulic acid = ?
show the reaction diagram
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UDP-glucose + ferulic acid = UDP + 4-O-glucosylferulic acid
show the reaction diagram
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UDP-glucose + ferulic acid = UDP + ferulic acid-4-O-beta-D-glucopyranoside
show the reaction diagram
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UDPglucose + ferulic acid = UDP + feruloyl-beta-1-D-glucose
show the reaction diagram
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UDPglucose + ferulic acid = UDP + feruloyl-beta-D-glucose + 4-O-glucosyl-ferulic acid
show the reaction diagram
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UDPglucose + ferulate = UDP + 1-O-feruloyl-beta-D-glucose
show the reaction diagram
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UDP-glucose + ferulic acid = UDP + 1-O-feruloyl-beta-D-glucose
show the reaction diagram
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UDPglucose + ferulic acid = UDP + 4-O-beta-D-glucopyranosyl-3-methoxycinnamic acid
show the reaction diagram
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3,4-dihydroxyphenylpropanoyl-CoA + ferulate = 3,4-dihydroxyphenylpropanoate + feruloyl-CoA
show the reaction diagram
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triolein + ferulic acid = monoferuloyl oleoyl glycerol + monoferuloyl dioleoyl glycerol
show the reaction diagram
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ferulate = 4-vinylguaiacol + CO2
show the reaction diagram
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ferulic acid = vanillin + acetyl-CoA
show the reaction diagram
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3-methoxy-4-hydroxy-trans-cinnamate + NH3 = 3-methoxy-4-hydroxy-L-phenylalanine
show the reaction diagram
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ferulic acid + CoASH + ATP = trans-feruloyl-CoA + products of ATP breakdown
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (541 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(2E)-3-(3-methoxyphenyl)prop-2-enoic acid + [reduced NADPH-hemoprotein reductase] + O2 = (2E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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ferulic acid + NADPH + ATP = ferulic acid + coniferyl aldehyde + coniferyl alcohol + NADP+ + AMP + phosphate
show the reaction diagram
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S-adenosyl-L-methionine + caffeic acid = S-adenosyl-L-homocysteine + ferulic acid
show the reaction diagram
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1-O-feruloyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = ferulate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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feruloylcholine + H2O = ferulic acid + choline
show the reaction diagram
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[5-O-feruloyl-alpha-L-arabinofuranosyl]-(1->3)-beta-D-xylopyranosyl-(1->4)-D-xylopyranose + H2O = ferulic acid + alpha-L-arabinofuranosyl-(1->3)-O-beta-D-xylopyranosyl-(1->4)-D-xylopyranose
show the reaction diagram
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feruloylated oligosaccharide + H2O = ferulic acid + ?
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
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enhances NADH-peroxidase activity in the presence of Mn2+
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enhances total turnover number compared to reaction without antioxidant
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activation of M-PST
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Inhibitor in Enzyme-catalyzed Reactions (45 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
24.5% inhibition at 0.1 mM
-
noncompetitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
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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
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inhibition of isozyme GST M1-1
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IC50 is above 5.0 mM
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80% residual activity at 0.5 mM
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enzyme activitiy of pectin lyase decreases significantly when 0.1 mg/l of ferulic acid is added
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15% inhibition at 0.01 mM, 58% inhibition at 0.05 mM
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inhibits enzyme form CM3
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3D Structure of Enzyme-Ligand-Complex (PDB) (13 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (32 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
5.2
-
pH 5.2, 45C

KM Value (85 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1
-
pH 7.8, 30C
1.7
-
-
0.0014
-
-
0.3585
-
-

Ki Value (7 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
10.7
-
-
1.17
-
-

IC50 Value (14 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.021
-
pH 7.0, 37C
0.0939
-
pH 8.0, 37C, versus xanthine
0.0049
-
25C, pH 7.4, cell lysate
5
-
IC50 is above 5.0 mM
0.034
-
pH 6.5, 37C

References & Links

Links to other databases for ferulic acid

ChEBI
PubChem
ChEBI
PubChem