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


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

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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
-
UDPglucose + gallate = UDP + 1-O-galloyl-beta-D-glucose
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (15 results)

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

Substrate in Enzyme-catalyzed Reactions (36 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
gallate + O2 = ?
show the reaction diagram
-
Kraft pulp + gallate + O2 = ? + H2O
show the reaction diagram
-
Kraft pulp + gallate + O2 = ? + H2O
show the reaction diagram
-
S-adenosyl-L-methionine + gallic acid = S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
UDPglucose + gallate = UDP + 1-O-galloyl-beta-D-glucose
show the reaction diagram
-
3'-phosphoadenylylsulfate + gallic acid = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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gallic acid + H2O = ?
show the reaction diagram
-
gallic acid + H2O = ?
show the reaction diagram
-
3,4,5-Trihydroxybenzoate = Pyrogallol + CO2
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (58 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3,4-dihydroxybenzoic acid + NADPH + H+ + O2 = gallic acid + NADP+ + H2O
show the reaction diagram
-
-
syringate + NADH + O2 = 3,4-dihydroxy-5-methoxybenzoate + gallate + NAD+ + H2O + formaldehyde
show the reaction diagram
-
-
3-O-methylgallate + tetrahydrofolate = gallate + 5-methyltetrahydrofolate
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
activation of P-PST and M-PST
-

Inhibitor in Enzyme-catalyzed Reactions (66 results)

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
-
mixed inhibition type
-
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
-
50% inhibition of urate formation above 0.2 mM, 50% inhibition of superoxide anion generation at 0.0026 mM
-
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
-
tested at 1.0 mM and under N2, 24% inhibition
-
slightly
-
5.3% inhibition at 0.1 mM
-
50% inhibition of overall enzyme reaction at 21 mM, 50% inhibition of ketoacyl reduction reaction at 26 mM
-
competitive inhibition
-
80-90% inhibition at 4-5 mM, mixed-type inhibition in vitro
-
gallic acid, time-dependent, irreversible
-
inhibitory in micromolar concentrations
-
48.8% inhibition at 1 mM
-
8% inhibition at 5mM
-
0.1 mg/ml, 9% inhibition
-
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
-
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) (4 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (8 results)

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

KM Value (22 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
4.6
-
pH 5.8, 25°C
0.002
-
pH 7.5, 38°C

Ki Value (15 results)

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 (12 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
3.8
-
-
0.046
-
pH 7.0, 23°C
0.08
-
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

Links to other databases for gallic acid

ChEBI
PubChem
ChEBI
PubChem