Ligand (-)-epicatechin

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Basic Ligand Information

Molecular Structure
Picture of (-)-epicatechin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H14O6
(-)-epicatechin
PFTAWBLQPZVEMU-UKRRQHHQSA-N
Synonyms:
(-)epicatechin, (2R,3R)-epicatechin, L-catechin, L-epicatechin

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
(-)-epicatechin + O2 = ?
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cyanidin + NADPH = (-)-epicatechin + NADP+ + H2O
show the reaction diagram
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(-)-epicatechin gallate + H2O = (-)-epicatechin + gallic acid
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-epicatechin + O2 = ?
show the reaction diagram
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(-)-epicatechin + H2O2 = ? + H2O
show the reaction diagram
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(-)-epicatechin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
(-)-epicatechin gallate + H2O = (-)-epicatechin + gallic acid
show the reaction diagram
-
-

Inhibitor in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
about 95% activity at 0.2 mM
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interacts with the R2 protein, leading to a loss of the tyrosyl radical EPR signal. Proliferation of cells exposed to (-)-epicatechin is downregulated, and deoxyribonucleotide levels are significantly diminished
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serves as prodrug for conversion into apocynin-like NAD(P)H oxidase inhibitors
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IC50: 0.06 mM with 2-hydroxyestradiol as substrate, IC50: 0.08 mM with 4-hydroxyestradiol as substrate
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50% inhibition of overall enzyme reaction at 3.8 mM, 50% inhibition of ketoacyl reduction reaction at 9.38 mM
-
IC50: 0.32 mM
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; complete inhibition of SULT1A1
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IC50: about 1.7 mM
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IC50: 0.0281 mM, noncompetitive inhibition
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(-)-epicatechin leads to a decreased arginase-2 mRNA expression after 24 h of incubation, in contrast a weak basal arginase-1 mRNA expression is not affected
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Enzyme Kinetic Parameters

KM Value (6 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0022
0.0082
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IC50 Value (9 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0032
-
pH 7.5, 22°C
0.08
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IC50: 0.06 mM with 2-hydroxyestradiol as substrate, IC50: 0.08 mM with 4-hydroxyestradiol as substrate
0.32
-
IC50: 0.32 mM
1.7
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IC50: about 1.7 mM
0.0281
-
IC50: 0.0281 mM, noncompetitive inhibition
0.0372
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-

References & Links

Links to other databases for (-)-epicatechin

ChEBI
PubChem
ChEBI
PubChem