Ligand vanillic acid

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Basic Ligand Information

Molecular Structure
Picture of vanillic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H8O4
vanillic acid
WKOLLVMJNQIZCI-UHFFFAOYSA-N
Synonyms:
3-methoxy-4-hydroxybenzoate, 3-methoxy-4-hydroxybenzoic acid, 4-hydroxy-3-methoxy-benzoate, 4-hydroxy-3-methoxybenzoate, 4-hydroxy-3-methoxybenzoic acid, 4-hydroxy-3-methoxy benzoic acid, vanillate, vanillinic 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
vanillate + NADPH + H+ + ATP = vanillin + NADP+ + AMP + diphosphate
show the reaction diagram
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UDP-glucose + vanillate = UDP + vanilloyl beta-D-glucoside
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
veratric acid + NAD(P)H + H+ + O2 = vanillic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
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-
vanillin + NAD+ = vanillinic acid + NADH + H+
show the reaction diagram
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1-O-vanilloyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = vanillate + cyanidin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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1-O-vanilloyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = vanillate + cyanidin 3,7-di-O-beta-D-glucoside
show the reaction diagram
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methyl vanillate + H2O = vanillate + methanol
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (38 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
vanillic acid + H2O2 = ?
show the reaction diagram
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vanillic acid + O2 = ?
show the reaction diagram
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vanillic acid + O2 = ?
show the reaction diagram
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4-Hydroxy-3-methoxybenzoate + NADH + O2 = ?
show the reaction diagram
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S-adenosyl-L-methionine + 4-hydroxy-3-methoxybenzoic acid = S-adenosyl-L-homocysteine + 3,4-dimethoxybenzoic acid
show the reaction diagram
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S-adenosyl-L-methionine + vanillate = methyl vanillate + S-adenosyl-L-homocysteine
show the reaction diagram
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S-adenosyl-L-methionine + vanillate = methyl vanillate + S-adenosyl-L-homocysteine
show the reaction diagram
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UDP-glucose + vanillic acid = UDP + 4-O-glucosylvanillic acid
show the reaction diagram
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UDP-glucose + vanillic acid = UDP + vanillic acid-4-O-beta-D-glucopyranoside
show the reaction diagram
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UDP-alpha-D-glucose + vanillic acid = UDP + 1-O-vanilloyl-beta-D-glucose
show the reaction diagram
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UDP-glucose + vanillic acid = ?
show the reaction diagram
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UDP-glucose + vanillic acid = UDP + 4-(beta-D-glucopyranosyloxy)-3-methoxybenzoic acid
show the reaction diagram
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UDP-glucose + vanillic acid = UDP + ?
show the reaction diagram
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UDP-glucose + vanillic acid = UDP + vanillic acid beta-D-glucoside
show the reaction diagram
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rutin + vanillic acid = quercetin + vanillic acid 4'-O-rutinoside
show the reaction diagram
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3-methoxy-4-hydroxybenzoate = 2-methoxyphenol + CO2
show the reaction diagram
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ATP + 4-hydroxy-3-methoxybenzoate + CoA = AMP + diphosphate + 4-hydroxy-3-methoxybenzoyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (48 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
vanillin aldehyde + acceptor + H2O = vanillic acid + reduced acceptor
show the reaction diagram
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veratric acid + NAD(P)H + H+ + O2 = vanillic acid + NAD(P)+ + H2O + formaldehyde
show the reaction diagram
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3-methoxybenzoate + [reduced NADPH-hemoprotein reductase] + O2 = 3-methoxy-4-hydroxybenzoate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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3,4-dimethoxybenzoate + NADH + O2 = 4-hydroxy-3-methoxybenzoate + NAD+ + H2O + formaldehyde
show the reaction diagram
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4-hydroxy-3-methoxybenzaldehyde + H2O + O2 = 4-hydroxy-3-methoxybenzoate + H2O2
show the reaction diagram
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3-methoxy-4-hydroxybenzaldehyde + NAD+ + H2O = 3-methoxy-4-hydroxybenzoate + NADH + H+
show the reaction diagram
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4-hydroxy-3-methoxybenzaldehyde + NAD+ + H2O = 4-hydroxy-3-methoxybenzoate + NADH + H+
show the reaction diagram
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3-methoxy-4-hydroxybenzaldehyde + H2O + O2 = 3-methoxy-4-hydroxybenzoate + ?
show the reaction diagram
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vanillin + O2 + H2O = vanillic acid + H2O2
show the reaction diagram
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4-Hydroxy-3-methoxy-benzaldehyde + carbamoyl methyl viologen = 4-Hydroxy-3-methoxy-benzoate + reduced carbamoyl methyl viologen
show the reaction diagram
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methyl vanillate + H2O = methanol + vanillate
show the reaction diagram
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vanillic acid 4-sulfate + H2O = vanillic acid + sulfate
show the reaction diagram
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N-vanilloyl-1-glycine + H2O = 4-hydroxy-3-methoxybenzoate + glycine
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
enhances NADH-peroxidase activity in the presence of Mn2+
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125.1% activity at 2.5 mM with cellobioside as substrate
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Inhibitor in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
45.4% inhibition at 0.015 mM, active site binding structure
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0.2 mM, 86% inhibition; 0.2 mM, 86% inhibition
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competitive inhibition
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inhibition of P-PST and M-PST
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inhibitory in micromolar concentrations
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good alpha-glucosidase inhibitory activity
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87.6% residual activity at 2.5 mM with 4-nitrophenyl beta-D-glucopyranoside as substrate
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3D Structure of Enzyme-Ligand-Complex (PDB) (18 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (8 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
102
-
pH 4.5, 55°C
11.8
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KM Value (17 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.054
-
-
0.125
-
-

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.003
-
-
1.3
-
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0.00232
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pH 8.5, 37°C
0.26
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pH 7.5, wild-type enzyme

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
3.89
-
pH not specified in the publication, temperature not specified in the publication, MAO-A
0.091
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0.00245
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pH 8.5, 37°C
0.18
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in 50 mM Tris-HCl buffer, pH 7.4, 10 mM MgCl2, 50 mM NaCl, 10 mM KCl, at 37°C
0.069
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References & Links

Links to other databases for vanillic acid

ChEBI
PubChem
ChEBI
PubChem