Ligand 4-hydroxybenzaldehyde

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Basic Ligand Information

Molecular Structure
Picture of 4-hydroxybenzaldehyde (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H6O2
4-hydroxybenzaldehyde
RGHHSNMVTDWUBI-UHFFFAOYSA-N
Synonyms:
4-Hydroxy-benzaldehyde, 4-hydroxybenzyl aldehyde, L-4-hydroxybenzaldehyde, p-Hydroxybenzaldehyde

Show all pahtways known for Show all pathways known for 4-hydroxybenzaldehyde

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoate + NADPH + H+
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(S)-2-hydroxy-2-(4-hydroxyphenyl)acetate + O2 = 4-hydroxybenzaldehyde + CO2 + H2O2
show the reaction diagram
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4-hydroxybenzyl alcohol + O2 = 4-hydroxybenzaldehyde + H2O2
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(S)-4-Hydroxymandelonitrile = Cyanide + 4-hydroxybenzaldehyde
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4-coumaroyl-CoA = 4-hydroxybenzaldehyde + acetyl-CoA
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Substrate in Enzyme-catalyzed Reactions (60 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxybenzaldehyde + NADPH + H+ = 4-hydroxybenzyl alcohol + NADP+
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4-hydroxybenzaldehyde + H2O2 = ?
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4-hydroxybenzaldehyde + NAD+ + H2O = 4-hydroxybenzoate + NADH + H+
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4-hydroxybenzaldehyde + H2O + O2 = 4-hydroxybenzoate + H2O2
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4-hydroxybenzaldehyde + NAD+ + H2O = 4-hydroxybenzoate + NADH + H+
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4-hydroxybenzaldehyde + NAD+ + H2O = 4-hydroxybenzoic acid + NADH + H+
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4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoate + NADPH + H+
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p-hydroxybenzaldehyde + NADP+ + H2O = p-hydroxybenzoic acid + NADPH + H+
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4-hydroxybenzaldehyde + NAD+ + H2O = 4-hydroxybenzoate + NADH + 2 H+
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4-hydroxybenzaldehyde + H2O + O2 = 4-hydroxybenzoate + ?
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p-hydroxybenzaldehyde + O2 + H2O = p-hydroxybenzoic acid + H2O2
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4-Hydroxybenzaldehyde + carbamoyl methyl viologen = 4-Hydroxybenzoate + reduced carbamoyl methyl viologen
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4-hydroxybenzaldehyde + pyruvate = ? + CO2
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4-hydroxybenzaldehyde + 2-oxoglutarate = (5R)-5-hydroxy-5-(4-hydroxyphenyl)-4-oxopentanoic acid + CO2
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UDP-glucose + 4-hydroxybenzaldehyde = UDP + 4-formylphenyl beta-D-glucopyranoside
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4-hydroxybenzaldehyde + glycine = D-4-hydroxyphenylserine
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4-hydroxybenzaldehyde + pyruvate = (3E)-4-(4-hydroxyphenyl)-2-oxobut-3-enoate + H2O
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cyanide + 4-hydroxybenzaldehyde = (2S)-(4-hydroxyphenyl)(hydroxy)ethanenitrile
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4-hydroxybenzaldehyde + HCN + H2O = ? + H2O
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Product in Enzyme-catalyzed Reactions (32 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxybenzyl alcohol + NAD+ = 4-hydroxybenzaldehyde + NADH
show the reaction diagram
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salicyl alcohol + NADP+ = p-hydroxybenzaldehyde + NADPH
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4-hydroxybenzyl alcohol + NADP+ = 4-hydroxybenzaldehyde + NADPH
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(S)-2-hydroxy-2-(4-hydroxyphenyl)acetate + O2 = 4-hydroxybenzaldehyde + CO2 + H2O2
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1-(4-hydroxybenzyl)imidazole + ascorbate + O2 = 4-hydroxybenzaldehyde + dehydroascorbate + H2O + ?
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4-methoxybenzaldehyde + AH2 + O2 = 4-hydroxybenzaldehyde + formaldehyde + A + H2O
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p-hydroxybenzoic acid + NADPH + ATP = p-hydroxybenzaldehyde + NADP+ + AMP + H2O
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p-hydroxybenzoic acid + ? = p-hydroxybenzaldehyde + ?
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4-Hydroxybenzoate + reduced carbamoyl methyl viologen = 4-Hydroxybenzaldehyde + carbamoyl methyl viologen
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4-acetoxybenzaldehyde + H2O = 4-hydroxybenzaldehyde + acetate
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4-diethyl phosphate benzaldehyde + H2O = 4-hydroxybenzaldehyde + diethyl phosphate
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(R)-4-hydroxymandelonitrile = cyanide + 4-hydroxybenzaldehyde
show the reaction diagram
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(S)-4-Hydroxymandelonitrile = Cyanide + 4-hydroxybenzaldehyde
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
50% inhibition above 10 mM, noncompetitive
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strong inhibition at 5 mM
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potent inhibitor, 1 mg/ml bovine serum albumin protects
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2.5 mM, 11% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (10 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.19
-
pH and temperature not specified in the publication
20
-
-
4
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apparent Kcat

KM Value (17 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
21.8
-
pH 6.5, 30°C
0.09
-
-
0.17
-
-
0.018
-
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0.0548
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apparent Km-value, pH 7.5 and 35°C
0.006
-
apparent KM
12
-
with carbamoyl methyl viologen as cosubstrate
6
-
pH 5.0, 25°C
5.9
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pH 5.0, 25°C

Ki Value (6 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.9
-
at pH 7.0 and 55°C
1.9
-
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2.3
-
-
0.33
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pH 7.5, wild-type enzyme

IC50 Value (6 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

Links to other databases for 4-hydroxybenzaldehyde

ChEBI
PubChem
ChEBI
PubChem