Ligand 2,4-Dihydroxybenzoate

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Basic Ligand Information

Molecular Structure
Picture of 2,4-Dihydroxybenzoate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H6O4
2,4-Dihydroxybenzoate
RZRNAYUHWVFMIP-KTKRTIGZSA-N
Synonyms:
2,4-dihydroxybenzoic acid, 4-hydroxysalicylate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,4-dihydroxybenzoate + NAD(P)H + H+ + O2 = benzene-1,2,4-triol + NAD(P)+ + H2O + CO2
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,4-dihydroxybenzoate + O2 = ?
show the reaction diagram
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2,4-dihydroxybenzoate + NADH + H+ + O2 = ?
show the reaction diagram
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2,4-dihydroxybenzoate = ?
show the reaction diagram
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2,4-dihydroxybenzoate + 2 NADPH + 2 bromide + 2 O2 + 2 H+ = 2,4-dibromo-6-hydroxyphenol + 4-bromo-2-hydroxyphenol + 2 NADP+ + CO2 + 4 H2O
show the reaction diagram
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S-adenosyl-L-methionine + 2,4-dihydroxybenzoic acid = S-adenosyl-L-homocysteine + 2-methoxy-4-hydroxybenzoic acid
show the reaction diagram
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ATP + 2,4-dihydroxybenzoic acid = diphosphate + (2,4-dihydroxybenzoyl)adenylate
show the reaction diagram
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2,4-dihydroxybenzoate = 3-hydroxyphenol + CO2
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2,4-dihydroxybenzoate = 1,3-dihydroxybenzene + CO2
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2-hydroxybenzoate + [reduced NADPH-hemoprotein reductase] + O2 = 2,4-dihydroxybenzoate + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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2,4-dihydroxybenzaldehyde + NAD+ + H2O = 2,4-dihydroxybenzoate + NADH + H+
show the reaction diagram
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methyl 2,4-dihydroxybenzoate + H2O = methanol + 2,4-dihydroxybenzoate
show the reaction diagram
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2,4-dihydroxybenzoyl-CoA + H2O = CoA + 2,4-dihydroxybenzoate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
increases the rate of NADP oxidation by 4-hydroxybenzoate, no hydroxylation during subsequent reoxidation by O2

Inhibitor in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
4.2 mM, 50% inhibition, noncompetitive
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competitive inhibition
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49.9% inhibition at 0.015 mM, active site binding structure
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competitive with respect to 2-oxoglutarate and ascorbate, noncompetitive with respect to Fe2+
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competitive with 4-hydroxybenzoate
over 70% inhibition at 10 mM
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strong
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (4 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
19.8
-
-
3.23
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pH 9.0, 37°C

KM Value (6 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.007
-
-
0.242
-
pH 9.0, 37°C

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.53
-
-
0.31
-
-
1.9
-
-
0.0012
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pH 7.8, 37°C

References & Links

Links to other databases for 2,4-Dihydroxybenzoate

ChEBI
PubChem
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PubChem