Ligand 4-hydroxybenzoic acid

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Basic Ligand Information

Molecular Structure
Picture of 4-hydroxybenzoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H6O3
4-hydroxybenzoic acid
FJKROLUGYXJWQN-UHFFFAOYSA-N
Synonyms:
4-carboxyphenol, 4-hydroxybenzoate, 4-hydroxy benzoic acid, p-hydroxybenzoate, p-hydroxybenzoic acid, p-hydroxy benzoic acid
Pathway Source
Pathways


Show all pahtways known for Show all BRENDA pathways known for 4-hydroxybenzoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (82 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
p-hydroxybenzoate + O2 = protocatechuic acid + H2O
show the reaction diagram
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4-hydroxybenzoate + NADPH + H+ + O2 = 3,4-dihydroxybenzoate + NADP+ + H2O
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S-adenosyl-L-methionine + 4-hydroxybenzoate = S-adenosyl-L-homocysteine + methyl 4-hydroxybenzoate
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geranyl diphosphate + 4-hydroxybenzoate = 3-geranyl-4-hydroxybenzoate + diphosphate
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ATP + 4-hydroxybenzoate + CoA = AMP + diphosphate + 4-hydroxybenzoyl-CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (24 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoate + NADPH + H+
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4-Hydroxybenzoyl-CoA + H2O = 4-Hydroxybenzoate + CoA
show the reaction diagram
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4-chlorobenzoate + H2O = 4-hydroxybenzoate + Cl-
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (207 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
p-hydroxybenzoate + O2 = protocatechuic acid + H2O
show the reaction diagram
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4-hydroxybenzoic acid + H2O2 + H+ = ?
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4-hydroxybenzoic acid + O2 = ?
show the reaction diagram
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4-hydroxybenzoate + O2 = ?
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4-hydroxybenzoate + NADH + H+ + O2 = hydroquinone + NAD+ + H2O + CO2
show the reaction diagram
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4-hydroxybenzoate + NADPH + H+ + O2 = 3,4-dihydroxybenzoate + NADP+ + H2O
show the reaction diagram
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4-hydroxybenzoate + NAD(P)H + O2 = quinol + NAD(P)+ + H2O2 + CO2
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4-hydroxybenzoic acid + NADPH + H+ + O2 = ? + NADP+ + H2O
show the reaction diagram
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4-hydroxybenzoate + ? = 3,4-dihydroxybenzoate + ?
show the reaction diagram
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4-hydroxybenzoate + NADH + O2 = 3,4-dihydroxybenzoate + NAD+ + H2O
show the reaction diagram
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p-hydroxybenzoic acid + NADPH + ATP = p-hydroxybenzaldehyde + NADP+ + AMP + H2O
show the reaction diagram
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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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S-adenosyl-L-methionine + 4-hydroxybenzoate = S-adenosyl-L-homocysteine + methyl 4-hydroxybenzoate
show the reaction diagram
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UDP-alpha-D-glucose + 4-hydroxybenzoic acid = UDP + 1-O-(4-hydroxybenzoyl)-beta-D-glucose
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UDP-alpha-D-glucose + 4-hydroxybenzoate = UDP + 1-O-(4-hydroxybenzoyl)-beta-D-glucopyranose
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p-hydroxybenzoic acid + UDP-glucose = UDP + 4-hydroxybenzoyl-beta-D-glucoside
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UDPglucose + 4-hydroxybenzoate = UDP + 4-(beta-D-glucosyloxy)benzoate
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UDPglucose + 4-hydroxybenzoic acid = UDP + glucosyl-4-hydroxybenzoate
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5-phospho-alpha-D-ribose 1-diphosphate + 4-hydroxybenzoate = 4-(beta-D-ribofuranosyl)hydroxybenzene 5'-phosphate + CO2 + diphosphate
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geranyl diphosphate + 4-hydroxybenzoate = 4-[[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy]benzoic acid
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geranyl diphosphate + 4-hydroxybenzoate = 3-geranyl-4-hydroxybenzoate + diphosphate
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4-Hydroxybenzoate = Phenol + CO2
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ATP + 4-hydroxybenzoate + CoA = AMP + diphosphate + 4-hydroxybenzoyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (102 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-hydroxybenzaldehyde + NADPH + H+ + O2 = 4-hydroxybenzoate + NADP+ + H2O
show the reaction diagram
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benzoic acid + [reduced NADPH-hemoprotein reductase] + O2 = 4-hydroxybenzoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
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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+
show the reaction diagram
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4-hydroxybenzaldehyde + NAD+ + H2O = 4-hydroxybenzoic acid + NADH + H+
show the reaction diagram
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4-hydroxybenzaldehyde + NADP+ + H2O = 4-hydroxybenzoate + NADPH + H+
show the reaction diagram
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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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1-O-4-hydroxybenzoyl-beta-D-glucose + cyanidin 3-O-beta-D-glucoside = 4-hydroxybenzoate + cyanidin 3,5-di-O-beta-D-glucoside
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4-carboxyphenyl acetate + H2O = 4-carboxyphenol + acetate
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4-acetoxybenzoate + H2O = 4-hydroxybenzoate + acetate
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p-hydroxybenzoyl-Ala + H2O = p-hydroxybenzoate + Ala
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N-4-hydroxybenzoylglycine + H2O = 4-hydroxybenzoate + glycine
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4-hydroxybenzonitrile + H2O = 4-hydroxybenzoic acid + NH3
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4-chlorobenzoate + H2O = 4-hydroxybenzoate + chloride
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Phenol + CO2 = 4-Hydroxybenzoate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activation of P-PST and M-PST
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109.7% activity at 2.5 mM with cellobioside as substrate
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Inhibitor in Enzyme-catalyzed Reactions (142 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
47.0% inhibition at 0.015 mM, active site binding structure
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38% inhibition at 4.5 mM
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0.1 mM, 79% inhibition
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21.4% residual activity at 0.1 mM
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5 mM, 88% loss of activity
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2.5 mM, 28% inhibition
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competitive
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isolated from seeds of Syagrus romanzoffiana
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97.5% 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) (38 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (27 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
311.7
-
native enzyme, at 30°C
0.002
-
in 100 mM Na-TAPS (pH 8.5), at 30°C
55
-
-
0.93
-
pH 8.0, 31°C, recombinant wild-type enzyme

KM Value (66 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
18.76
-
native enzyme, at 30°C
0.15
-
pH 7.0, 30°C
0.035
-
-
6.33
-
-
3.45
-
-
0.6424
-
-
5.6
-
in 100 mM Na-TAPS (pH 8.5), at 30°C
0.158
-
pH 8.0, 31°C, recombinant wild-type enzyme

Ki Value (17 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.014
-
pH 7.0, 25°C
2.3
-
-
0.07
-
pH 4.8, 50°C, Ki(slope)
0.00932
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at pH 7.5 and 20°C

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
1.3
-
-
0.062
-
-
0.0564
-
pH 6.5, 37°C

References & Links

Links to other databases for 4-hydroxybenzoic acid

ChEBI
PubChem
ChEBI
PubChem