Ligand 3-hydroxybenzoate

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Basic Ligand Information

Molecular Structure
Picture of 3-hydroxybenzoate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H6O3
3-hydroxybenzoate
IJFXRHURBJZNAO-UHFFFAOYSA-N
Synonyms:
3-Carboxyphenol, 3-Hydroxybenzoic acid, m-Hydroxybenzoate, m-hydroxybenzoic acid


Show all pahtways known for Show all BRENDA pathways known for 3-hydroxybenzoate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-hydroxybenzoate + electron donor + O2 = 2,3-dihydroxybenzoate + oxidized electron donor + H2O
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S-adenosyl-L-methionine + 3-hydroxybenzoate = S-adenosyl-L-homocysteine + methyl 3-hydroxybenzoate
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UDP-glucose + 3-hydroxybenzoate = UDP + 3-hydroxybenzoyl beta-D-glucoside
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3-hydroxybenzoate + pyruvate + H2O = chorismate
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ATP + 3-hydroxybenzoate + CoA = AMP + diphosphate + 3-hydroxybenzoyl-CoA
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In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
m-anisate + O2 + NADH = m-hydroxybenzoate + NAD+ + H2O + formaldehyde
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Substrate in Enzyme-catalyzed Reactions (38 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
m-hydroxybenzoate + NADH + O2 = 1,3-dihydroxybenzene + CO2 + NAD+ + H2O
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m-hydroxybenzoate + NADPH + O2 = protocatechuate + NADP+ + H2O
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3-hydroxybenzoic acid + NADPH + H+ + O2 = ? + NADP+ + H2O
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3-hydroxybenzoate + NADH + O2 = 3,4-dihydroxybenzoate + NAD+ + H2O
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3-hydroxybenzoate + electron donor + O2 = 2,3-dihydroxybenzoate + oxidized electron donor + H2O
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m-hydroxybenzoic acid + NADPH + ATP = m-hydroxybenzaldehyde + NADP+ + AMP + H2O
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3-Hydroxybenzoate + reduced carbamoyl methyl viologen = 3-Hydroxybenzaldehyde + carbamoyl methyl viologen
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ATP + 3-hydroxybenzoate = ?
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3-hydroxybenzoate + pyruvate + H2O = chorismate
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ATP + m-hydroxybenzoate + CoA = AMP + diphosphate + m-hydroxybenzoyl-CoA
show the reaction diagram
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ATP + 3-hydroxybenzoate + CoA = AMP + diphosphate + 3-hydroxybenzoyl-CoA
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ATP + 3-hydroxybenzoate + CoA = AMP + diphosphate + 3-hydroxybenzoyl-CoA
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ATP + 3-hydroxybenzoic acid + holo-[aryl-carrier protein] = AMP + diphosphate + 3-hydroxybenzoyl-[aryl-carrier protein]
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ATP + 3-hydroxybenzoate + phosphopantetheinylated EntB = arylated EntB + AMP + diphosphate
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Product in Enzyme-catalyzed Reactions (37 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
m-anisate + O2 + NADH = m-hydroxybenzoate + NAD+ + H2O + formaldehyde
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3-methoxybenzoic acid + [reduced NADPH-hemoprotein reductase] + O2 = 3-hydroxybenzoic acid + [oxidized NADPH-hemoprotein reductase] + H2O
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3-methoxybenzoate + NADH + O2 = 3-hydroxybenzoate + NAD+ + H2O + formaldehyde
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3-hydroxybenzaldehyde + H2O + O2 = 3-hydroxybenzoate + H2O2
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3-hydroxybenzaldehyde + NAD+ + H2O = 3-hydroxybenzoate + NADH + H+
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3-hydroxybenzaldehyde + NADP+ + H2O = 3-hydroxybenzoate + NADPH + H+
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3-hydroxybenzaldehyde + NAD+ + H2O = 3-hydroxybenzoate + NADH + 2 H+
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3-hydroxybenzaldehyde + NAD+ + H2O = 3-hydroxybenzoate + NADH + 2 H+
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3-hydroxybenzaldehyde + NAD+ + H2O = 3-hydroxybenzoate + NADH + H+
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3-hydroxybenzaldehyde + H2O + O2 = 3-hydroxybenzoate + H2O2
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3-hydroxybenzaldehyde + H2O + O2 = 3-hydroxybenzoate + ?
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m-hydroxybenzaldehyde + O2 + H2O = m-hydroxybenzoic acid + H2O2
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3-hydroxybenzaldehyde + H2O + 2,6-dichlorophenol-indophenol = 3-hydroxybenzoate + reduced 2,6-dichlorophenol-indophenol
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3-hydroxybenzoyl-CoA + H2O = CoA + 3-hydroxybenzoate
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3-carboxyphenyl sulfate + H2O = 3-carboxyphenol + sulfate
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4-Hydroxyphthalate = 3-Hydroxybenzoate
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
strongly stimulates activity

Inhibitor in Enzyme-catalyzed Reactions (26 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
biologically inactive, 28% inhibition at 0.2 mM
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47.6% inhibition at 0.015 mM, active site binding structure
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competitive inhibition
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competitive
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20 mM, 47% inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (5 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (11 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
4.5
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0.11
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at pH 6.5 and 26°C
1.8
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pH 8.0, 31°C, recombinant wild-type enzyme
15
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pH and temperature not specified in the publication
0.3
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pH 7.8, 25°C, recombinant EntE

KM Value (27 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.4644
-
-
0.229
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pH 8.0, 31°C, recombinant wild-type enzyme
0.07
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pH 7.8, 25°C, recombinant EntE

Ki Value (10 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
14.7
-
-
0.004
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3.3
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20
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value above
2.1
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0.4
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IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
1.1
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References & Links

Links to other databases for 3-hydroxybenzoate

ChEBI
PubChem
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PubChem