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BRENDA support

Ligand gallic acid

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Basic Ligand Information

Molecular Structure
Picture of gallic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C7H6O5
gallic acid
LNTHITQWFMADLM-UHFFFAOYSA-N
Synonyms:
3,4,5-Trihydroxybenzoate, 3,4,5-trihydroxybenzoic, 3,4,5-Trihydroxybenzoic acid, gallate
Pathway Source
Pathways
BRENDA
gallate degradation
KEGG
Aminobenzoate degradation, Biosynthesis of phenylpropanoids, Biosynthesis of various plant secondary metabolites, Microbial metabolism in diverse environments
MetaCyc
gallate biosynthesis, gallate degradation I, gallate degradation II, gallate degradation III (anaerobic), galloylated catechin biosynthesis more


Show all pahtways known for Show all BRENDA pathways known for gallic acid

Roles as Enzyme Ligand

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

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
gallic acid + O2 = 2-pyrone-4,6-dicarboxylic acid + H2O
show the reaction diagram
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UDP-glucose + gallate = UDP + galloyl beta-D-glucoside
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (16 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-dehydroshikimate + NADP+ = gallate + NADPH + H+
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (42 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
gallic acid + H2O2 = ?
show the reaction diagram
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gallic acid + H2O2 + H+ = oxidized gallic acid + H2O
show the reaction diagram
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gallic acid + H2O2 = ? + H2O
show the reaction diagram
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gallate + O2 = ?
show the reaction diagram
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Kraft pulp + gallate + O2 = ? + H2O
show the reaction diagram
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Kraft pulp + gallate + O2 = ? + H2O
show the reaction diagram
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S-adenosyl-L-methionine + gallic acid = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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UDP-glucose + gallate = UDP + galloyl beta-D-glucoside
show the reaction diagram
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3'-phosphoadenylylsulfate + gallic acid = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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gallic acid + H2O = ?
show the reaction diagram
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gallic acid + H2O = ?
show the reaction diagram
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3,4,5-Trihydroxybenzoate = Pyrogallol + CO2
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (60 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3-dehydroshikimate + NADP+ = gallate + NADPH + H+
show the reaction diagram
-
syringate + NADH + H+ + O2 = 3,4-dihydroxy-5-methoxybenzoate + gallate + NAD+ + H2O + formaldehyde
show the reaction diagram
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3-O-methylgallate + tetrahydrofolate = gallate + 5-methyltetrahydrofolate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (6 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activation of P-PST and M-PST
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Inhibitor in Enzyme-catalyzed Reactions (67 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
is a non-competitive inhibitor with respect to UDP-glucose and NAD+. It decreases specific activities of UGDH, but does not affect UGDH protein expression, thus UGDH activity is inhibited by polyphenols at the post-translational level. Gallic acid exerts strong antiproliferative activity in breast cancer cells. Heat inactivation of UGDH is accelerated to a greater degree by quercetin than by gallic acid. In the presence of gallic acid, the activity remaining after 30 min is 55% that of control
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0.001 mM, 50% inhibition, reduction of androst-4-en-3,17-dione
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competetive inhibition of 3,3',5,5'-tetramethylbenzidine oxidation
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competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
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0.1 mM, 20% loss of activity
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50% inhibition of urate formation above 0.2 mM, 50% inhibition of superoxide anion generation at 0.0026 mM
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inhibition of enzyme activity and induction of dose-dependent apoptosis and attenuated progression from G0/G1 to S phase of cells cycle. Highly synergistic effects of simultaneous treatment of cells with gallic acid and enzyme inhibitor N',3,4,5-tetrahydroxybenzenecarboximidamide
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tested at 1.0 mM and under N2, 24% inhibition
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slightly
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5.3% inhibition at 0.1 mM
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50% inhibition of overall enzyme reaction at 21 mM, 50% inhibition of ketoacyl reduction reaction at 26 mM
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competitive inhibition
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80-90% inhibition at 4-5 mM, mixed-type inhibition in vitro
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gallic acid, time-dependent, irreversible
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inhibitory in micromolar concentrations
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48.8% inhibition at 1 mM
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8% inhibition at 5mM
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0.1 mg/ml, 9% inhibition
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91.1% and 75.3% residual activity at 2.5 mM with 4-nitrophenyl beta-D-glucopyranoside and cellobioside as substrate, respectively
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noncompetitive inhibition
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slight inhibition
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a noncompetitive inhibitor
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enzyme activitiy of pectin lyase decreases significantly when 0.1 mg/l of gallic acid is added
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3D Structure of Enzyme-Ligand-Complex (PDB) (16 results)

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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (16 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
675
-
pH 7.0, 40°C
15.22
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at pH 6.0 and 28°C
28.2
-
-
42
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pH 6.2, 40°C

KM Value (31 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
4.6
-
pH 5.8, 25°C
0.1128
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at pH 6.0 and 28°C
1.3
-
pH 6.0, temperature not specified in the publication
0.002
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pH 7.5, 38°C

Ki Value (15 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
32
-
pH 7.0, 45°C
2.3
-
-
6.7
-
-
0.03
-
-
13.4
-
pH 6.8, 30°C
0.7
-
-
1.6
-
pH 6.8, 37°C
0.45
-
endogenous tannase
0.00095
-
pH 8.5, 37°C
0.018
-
pH 7.5, 37°C

IC50 Value (13 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
12.27
-
recombinant enzyme, pH 6.5, 50°C
3.8
-
-
0.046
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pH 7.0, 23°C
0.08
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in 0.1 M sodium phosphate buffer, pH 8.0, using 50 mM sodium glutamate and 0.2 mM NAD+
0.0068
-
-
0.001
-
pH 8.5, 37°C
0.0444
-
pH 7.5, 37°C
0.132
-
pH 6.5, 37°C

References & Links

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Links to other databases for gallic acid

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ChEBI
PubChem
ChEBI
PubChem