Ligand 2,5-dihydroxybenzoic acid

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Basic Ligand Information

Molecular Structure
Picture of 2,5-dihydroxybenzoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H6O4
2,5-dihydroxybenzoic acid
WXTMDXOMEHJXQO-UHFFFAOYSA-N
Synonyms:
2,5-Dihydroxybenzoate, gentisate, gentisic acid


Show all pahtways known for Show all BRENDA pathways known for 2,5-dihydroxybenzoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

In Vivo Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE

Substrate in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2,5-dihydroxybenzoate + O2 = ?
show the reaction diagram
-
gentisate + O2 = maleylpyruvate
show the reaction diagram
-
2,5-dihydroxybenzoate + NADPH + O2 = ? + NADP+ + H2O
show the reaction diagram
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4-coumaroyl-CoA + gentisate = CoA + 5-O-(4-coumaroyl)gentisate
show the reaction diagram
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ATP + 2,5-dihydroxybenzoic acid = diphosphate + (2,5-dihydroxybenzoyl)adenylate
show the reaction diagram
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2,5-dihydroxybenzoate = 4-hydroxyphenol + CO2
show the reaction diagram
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2,5-Dihydroxybenzoate = Hydroquinone + CO2
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
gentisaldehyde + NAD+ = gentisic acid + NADH
show the reaction diagram
-
2,5-dihydroxybenzaldehyde + NADP+ + H2O = 2,5-dihydroxybenzoate + NADPH + H+
show the reaction diagram
-
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2,5-dihydroxybenzaldehyde + H2O + 2,6-dichlorophenol-indophenol = 2,5-dihydroxybenzoate + reduced 2,6-dichlorophenol-indophenol
show the reaction diagram
-
-
methyl gentisate + H2O = methanol + gentisate
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
i.e. gentisate, strongly stimulates the NADH oxidase activity of the enzyme
-
activation of P-PST and M-PST
-

Inhibitor in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
2.6 mM, 50% inhibition, noncompetitive
-
21.2% inhibition at 0.015 mM, active site binding structure
-
competitive with respect to 2-oxoglutarate and ascorbate, noncompetitive with respect to Fe2+
-
over 70% inhibition at 10 mM
-
competitive
-
weak
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3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (11 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
7
-
in 50 mM Tris-SO4 (pH 8.0), at 25°C
3.15
-
pH 9.0, 37°C

KM Value (28 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.823
-
pH 8.0, 25°C, wild-type enzyme
0.5
-
cosubstrate NADPH
0.14
-
in 50 mM Tris-SO4 (pH 8.0), at 25°C
0.552
-
pH 9.0, 37°C

Ki Value (4 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.29
-
-
1.4
-
-
0.35
-
-
0.115
-
presence of MnCl2, overnight (15 h) pre-incubation of compound and enzyme before initiation of the reaction with GDP-fucose

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.059
-
pH 6.5, 37°C

References & Links

Links to other databases for 2,5-dihydroxybenzoic acid

ChEBI
PubChem
ChEBI
PubChem