Ligand epigallocatechin

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Basic Ligand Information

Molecular Structure
Picture of epigallocatechin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H14O7
epigallocatechin
XMOCLSLCDHWDHP-IUODEOHRSA-N
Synonyms:
(-)-epigallocatechin, (2R,3R)-epigallocatechin, epi-gallocatechin

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
epigallocatechin + O2 = ? + 2 H2O
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(-)-epigallocatechin gallate + H2O = (-)-epigallocatechin + gallic acid
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(-)-epigallocatechin + O2 = ?
show the reaction diagram
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sucrose + (-)-epigallocatechin = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
delphinidin + NADPH = (-)-epigallocatechin + (-)-gallocatechin + NADP+ + H2O
show the reaction diagram
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delphinidin + 2 NADPH + 2 H+ = epigallocatechin + 2 NADP+
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (30 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
less than 80% activity at 0.2 mM
-
the most potent compound with anti-LDH-5 activity under both normoxia and hypoxia conditions
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NADP+-competitive inhibitor of glucose-6-phosphate dehydrogenase
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50% inhibition at 1.4 mM
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slightly, catechin, non-competitive with both NADPH and GSSG, influence on glutathione recognition
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IC50: 0.073 mM
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complete inhibition of SULT1A1
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82% residual activity at 20 mg/ml
-
IC50: about 0.3 mM
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strong time-dependent inactivation of urease that is not due to their oxygen sensitivity. Rather, the compound appears to inactivate urease by reacting with a specific Cys residue located on the flexible loop. Substitution of this cysteine by alanine in the C319A variant increases the urease resistance
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a mixed-type noncompetitive inhibitor
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0.04 mM, 6.9% inhibition, noncompetitve, CD spectral analysis of complex with enzyme, preferred site of binding is around residues 34-39 with possible hydrogen bonding to K7 and R10
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i.e. (2R,3R)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

KM Value (7 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE

Ki Value (3 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0299
-
pH 7.5, 37°C

IC50 Value (15 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.049
-
pH 7.0, 23°C
0.008
-
25°C, pH 7.4, cell lysate
0.073
-
IC50: 0.073 mM
0.075
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pH 6.8, 30°C
0.3
-
IC50: about 0.3 mM
0.0575
-
pH 7.5, 37°C
3.61
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References & Links

Links to other databases for epigallocatechin

ChEBI
PubChem
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PubChem