Ligand vanillin

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Basic Ligand Information

Molecular Structure
Picture of vanillin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C8H8O3
vanillin
MWOOGOJBHIARFG-UHFFFAOYSA-N
Synonyms:
3-Methoxy-4-hydroxybenzaldehyde, 4-Hydroxy-3-methoxy-benzaldehyde, 4-hydroxy-3-methoxybenzaldehyde, p-hydroxy-m-methoxy-benzaldehyde, vanillaldehyde, vanillic aldehyde, vanillin aldehyde, vanillyl aldehyde

Show all pahtways known for Show all pathways known for vanillin

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxy-3-methoxybenzaldehyde + NAD+ + H2O = 4-hydroxy-3-methoxybenzoate + NADH + H+
show the reaction diagram
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3'-phosphoadenylyl sulfate + vanillin = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
vanillyl alcohol + NAD+ = vanillyl aldehyde + NADH + H+
show the reaction diagram
-
-
vanillyl alcohol + O2 = vanillin + H2O2
show the reaction diagram
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4-hydroxy-3-methoxybenzyl alcohol + O2 = 4-hydroxy-3-methoxybenzaldehyde + H2O2
show the reaction diagram
-
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S-adenosyl-L-methionine + 3,4-dihydroxybenzaldehyde = S-adenosyl-L-homocysteine + vanillin
show the reaction diagram
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glucovanillin + H2O = vanillin + beta-D-glucose
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (37 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
vanillin + NADPH = 4-hydroxy-3-methoxybenzyl alcohol + NADP+
show the reaction diagram
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vanillin + NADH + H+ = vanillin alcohol + NAD+
show the reaction diagram
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vanillin aldehyde + acceptor + H2O = vanillic acid + reduced acceptor
show the reaction diagram
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vanillin + O2 + AH2 = 3,4-dihydroxy-5-methoxybenzaldehyde + H2O + A
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-methoxybenzoic acid + 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
-
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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UDP-glucose + vanillin = UDP + vanillin-4-O-beta-D-glucopyranoside
show the reaction diagram
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vanillin + UDP-glucuronate = UDP + vanillin O-glucuronide
show the reaction diagram
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UDP-glucose + vanillin = ?
show the reaction diagram
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UDPglucose + vanillin = UDP + 4-beta-D-glucopyranosyloxy 3-methoxybenzaldehyde
show the reaction diagram
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UDP-glucose + vanillin = UDP + vanillin beta-D-glucoside
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
vanillyl alcohol + NAD+ = vanillin + NADH
show the reaction diagram
-
-
4-hydroxy-3-methoxybenzyl alcohol + NADP+ = 4-hydroxy-3-methoxybenzaldehyde + NADPH
show the reaction diagram
-
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vanillyl alcohol + NAD+ = vanillin + NADH + H+
show the reaction diagram
-
-
4-hydroxy-3-methoxybenzyl alcohol + O2 = 4-hydroxy-3-methoxybenzaldehyde + H2O2
show the reaction diagram
-
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4-hydroxy-3-methoxybenzyl alcohol + O2 = 4-hydroxy-3-methoxybenzaldehyde + H2O2
show the reaction diagram
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1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)propane-1,3-diol + H2O2 = vanillin + hydroxyacetaldehyde + guaiacol
show the reaction diagram
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vanillyl alcohol + H2O2 = vanillaldehyde + H2O
show the reaction diagram
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1,2-bis(4'-hydroxy-3'-methoxyphenyl)ethylene + O2 = vanillin
show the reaction diagram
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2-methoxy-4-methylphenol + acceptor + H2O = 3-methoxy-4-hydroxybenzaldehyde + reduced acceptor
show the reaction diagram
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vanillylamine + H2O + O2 = vanillic aldehyde + NH3 + H2O2
show the reaction diagram
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glucovanillin + H2O = vanillin + beta-D-glucose
show the reaction diagram
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vanillin cyanohydrin = cyanide + vanillin
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
2 mM
-

Inhibitor in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
mixed type of inhibition
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mixed inhibition type
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decreases Plk1 expression
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8.5% inhibition at 1 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (3 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
3.33
-
pH 6.1, 30°C
18
-
apparent Kcat

KM Value (19 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.4
-
pH 6.1, 30°C
0.12
-
-
0.155
-
recombinant ALDH3A1
0.044
-
apparent KM
3
-
4-methylbenzoate, with reduced carbamoyl methyl viologen as cosubstrate; with carbamoyl methyl viologen as cosubstrate
0.64
-
-

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0079
-
at 37°C in 0.1 M Na-K phosphate buffer (pH 7.4)
0.1
-
pH 7.0, 45°C
5.1
-
pH 6.1, 30°C
0.16
-
pH 6.5, temperature not specified in the publication

References & Links

Links to other databases for vanillin

ChEBI
PubChem
ChEBI
PubChem