Ligand 3,4-dihydroxybenzoic acid

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Basic Ligand Information

Molecular Structure
Picture of 3,4-dihydroxybenzoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H6O4
3,4-dihydroxybenzoic acid
YQUVCSBJEUQKSH-UHFFFAOYSA-N
Synonyms:
3,4-dihydroxybenzoate, protocatechuate, protocatechuic acid


Show all pahtways known for Show all BRENDA pathways known for 3,4-dihydroxybenzoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (30 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
protocatechuate + O2 = 4-carboxy-2-hydroxymuconate semialdehyde
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (23 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
p-hydroxybenzoate + O2 = protocatechuic acid + H2O
show the reaction diagram
-
-
4-sulfobenzoate + NADH + O2 = 3,4-dihydroxybenzoate + sulfite + NAD+
show the reaction diagram
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4,5-Dihydroxyphthalate = 3,4-Dihydroxybenzoate + CO2
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (100 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
protocatechuate + NADP+ + H2O = 2-pyrone-4,6-dicarboxylic acid + NADPH + H+
show the reaction diagram
-
protocatechuic acid + O2 = ?
show the reaction diagram
-
3,4-dihydroxybenzoic acid + O2 = 2-hydroxy-5-carboxymuconate semialdehyde
show the reaction diagram
-
protocatechuate + O2 = ?
show the reaction diagram
-
protocatechuate + O2 = ?
show the reaction diagram
-
protocatechuate + O2 = 4-carboxy-2-hydroxymuconate semialdehyde
show the reaction diagram
protocatechuic acid + NAD(P)H + O2 + H2O = ?
show the reaction diagram
-
3,4-dihydroxybenzoate + ? = ?
show the reaction diagram
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3,4-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 + 3,4-dihydroxybenzoic acid = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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4-coumaroyl-CoA + 3,4-dihydroxybenzoate = CoA + 3-O-(4-coumaroyl)oxy-4-hydroxybenzoate
show the reaction diagram
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UDP-glucose + protocatechuic acid = UDP + ?
show the reaction diagram
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UDPglucose + protocatechuate = UDP + protocatechuyl-beta-D-glucose
show the reaction diagram
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3,4-Dihydroxybenzoate = Catechol + CO2
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (69 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
p-hydroxybenzoate + O2 = protocatechuic acid + H2O
show the reaction diagram
-
-
4-sulfobenzoate + NADH + O2 = 3,4-dihydroxybenzoate + sulfite + NAD+
show the reaction diagram
-
4-hydroxybenzoate + ? = 3,4-dihydroxybenzoate + ?
show the reaction diagram
-
4-hydroxybenzoic acid + O2 + AH2 = 3,4-dihydroxybenzoic acid + H2O + A
show the reaction diagram
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3,4-dihydroxybenzaldehyde + NAD+ + H2O = 3,4-dihydroxybenzoate + NADH + H+
show the reaction diagram
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-
3,4-dihydroxybenzaldehyde + H2O + O2 = 3,4-dihydroxybenzoate + H2O2
show the reaction diagram
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-
3,4-dihydroxybenzaldehyde + NAD+ + H2O = 3,4-dihydroxybenzoate + NADH + H+
show the reaction diagram
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3,4-dihydroxybenzaldehyde + NAD+ + H2O = 3,4-dihydroxybenzoic acid + NADH + H+
show the reaction diagram
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3,4-dihydroxybenzaldehyde + NAD+ + H2O = 3,4-dihydroxybenzoate + NADH + H+
show the reaction diagram
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-
protocatechualdehyde + O2 + H2O = protocatechuic acid + H2O2
show the reaction diagram
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ethyl 3,4-dihydroxybenzoate + H2O = ethanol + 3,4-dihydroxybenzoate
show the reaction diagram
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3,4-dihydroxybenzoyl-CoA + H2O = CoA + 3,4-dihydroxybenzoate
show the reaction diagram
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3,4-dihydroxybenzoyl-CoA + H2O = CoA + 3,4-dihydroxybenzoate
show the reaction diagram
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4,5-Dihydroxyphthalate = 3,4-Dihydroxybenzoate + CO2
show the reaction diagram
-
Catechol + CO2 = 3,4-Dihydroxybenzoate
show the reaction diagram
-
3,4-dihydroxyphthalate = 3,4-dihydroxybenzoate + CO2
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activates
-
enhances enzyme activity
-

Inhibitor in Enzyme-catalyzed Reactions (71 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
12.6% inhibition at 0.002 mM
-
0.24 mM, 50% inhibition, noncompetitive
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51.6% inhibition at 0.015 mM, active site binding structure; 73.3% inhibition at 0.015 mM, active site binding structure
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0.0005 mM, 20% inhibition
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0.2 mM, 94% inhibition; 0.2 mM, 94% inhibition
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20% inhibition at 0.05 mM
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substrate inhibition
competitive inhibitor with respect to 2-oxoglutarate
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above 50% inhibition at 2 mM
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competitive inhibition of urate and superoxide anion formation
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0.8 mM, about 40% inhibition
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50% inhibition of overall enzyme reaction at 9.0 mM, 50% inhibition of ketoacyl reduction reaction at 30 mM
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inhibition of P-PST and M-PST
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competitive
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weak
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a scaffold hit from library screening
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3D Structure of Enzyme-Ligand-Complex (PDB) (16 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (51 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.04
-
in 50 mM Tris/HCl, pH 7.2, 25°C
16.8
-
-
0.013
-
pH 7.5, 37°C, in presence of 0.1 mM Co2+
44
-
pH 6.2, 40°C
18.3
-
-
90
-
-

KM Value (66 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.31
-
in 50 mM Tris/HCl, pH 7.2, 25°C
0.009
-
-
0.039
-
pH 7.5, 37°C, in presence of 0.1 mM Co2+
1.48
-
pH 7.5, 30°C
3.2
-
pH 6.2, 40°C
0.59
-
-

Ki Value (24 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2.3
-
-
0.0006
-
-
0.01
-
pH 7.8, 37°C, Ki-value is determined using soluble extracts of cells expressing enzyme-FLAGHis
0.55
-
-
0.09
-
pH 7.8, 30°C
0.137
-
presence of MnCl2, overnight (15 h) pre-incubation of compound and enzyme before initiation of the reaction with GDP-fucose
0.00129
-
pH 8.5, 37°C

IC50 Value (9 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
2.8
-
-
0.032
-
pH 7.5, 35°C
0.042
-
the effect of the formosan apple constituents on hydroxyl radical-scavenging activity
0.00134
-
pH 8.5, 37°C
0.047
-
pH 6.5, 37°C

References & Links

Links to other databases for 3,4-dihydroxybenzoic acid

ChEBI
PubChem
ChEBI
PubChem