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BRENDA support

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:
(-)-catechin, (-)epicatechin, (2R,3R)-epicatechin, epicatechol, 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 (6 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
cyanidin + NADPH + H+ = (-)-epicatechin + NADP+ + H2O
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (14 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
L-epicatechin + O2 = ?
show the reaction diagram
-
(-)-epicatechin + H2O2 = ? + H2O
show the reaction diagram
-
(-)-epicatechin + NADH + H+ = cyanidin + NAD+
show the reaction diagram
-
S-adenosyl-L-methionine + (-)-epicatechin = S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
(-)-epicatechin + S-adenosyl-L-methionine = S-adenosyl-L-homocysteine + ?
show the reaction diagram
-
sucrose + (-)-epicatechin = D-fructose + (-)-epicatechin-3'-O-alpha-D-glucopyranoside
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
2 cyanidin + 4 NADPH + 4 H+ = (+)-epicatechin + (-)-catechin + 4 NADP+
show the reaction diagram
-

Inhibitor in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
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
-
serves as prodrug for conversion into apocynin-like NAD(P)H oxidase inhibitors
-
IC50: 0.06 mM with 2-hydroxyestradiol as substrate, IC50: 0.08 mM with 4-hydroxyestradiol as substrate
-
50% inhibition of overall enzyme reaction at 3.8 mM, 50% inhibition of ketoacyl reduction reaction at 9.38 mM
-
IC50: 0.32 mM
-
complete inhibition of SULT1A1
-
IC50: about 1.7 mM
-
IC50: 0.0281 mM, noncompetitive inhibition
-
(-)-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
-

Enzyme Kinetic Parameters

KM Value (6 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0022
0.0082
-

IC50 Value (10 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
-999
-
value above 2.5 mM, pH 6, 25°C
0.0032
-
pH 7.5, 22°C
0.08
-
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
-
IC50: about 1.7 mM
0.0281
-
IC50: 0.0281 mM, noncompetitive inhibition
0.0372
-
-

References & Links

Links to other databases for (-)-epicatechin

ChEBI
PubChem
ChEBI
PubChem