Ligand epicatechin

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

Basic Ligand Information

Molecular Structure
Picture of epicatechin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H14O6
epicatechin
PFTAWBLQPZVEMU-ZFWWWQNUSA-N
Synonyms:
(+)-epicatechin, (2S,3S)-3',4',5,7-tetrahydroxyflavan-3-ol, D-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 = ? + 2 H2O
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
4beta-(S-cysteinyl)-epicatechin + NADPH + H+ = epicatechin + cysteine + NADP+
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
epicatechin + O2 = ?
show the reaction diagram
-
(+)-epicatechin + 2 NADP+ = cyanidin + 2 NADPH + 2 H+
show the reaction diagram
-
epicatechin + UDP-glucuronate = ?
show the reaction diagram
-
UDP-alpha-D-glucose + epicatechin = UDP + ?
show the reaction diagram
-
UDP-glucose + epicatechin = UDP + epicatechin 3-O-beta-D-glucoside
show the reaction diagram
-
3'-phosphoadenylyl sulfate + epicatechin = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4beta-(S-cysteinyl)-epicatechin + NADPH + H+ = epicatechin + cysteine + NADP+
show the reaction diagram
-
-

Activator in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.03 mM completely prevents inactivation of glutamine synthetase by peroxynitrite
-

Inhibitor in Enzyme-catalyzed Reactions (23 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 0.06 mM
-
slightly, catechin, non-competitive with both NADPH and GSSG, influence on glutathione recognition
-
a flavonol, 0.888 mM, pH 6.0, room temperature, 10.3% maximum inhibition
-
noncompetitive
-
slight inhibition
-
0.04 mM, 4.4% 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
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE

KM Value (13 results)

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

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.828
-
pH 8.3, 37°C

IC50 Value (15 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.06
-
IC50: 0.06 mM
0.0166
-
pH 7.0 and 37°C
0.2
-
above, pH 6.8, 30°C
0.2
-
pH 7.0, 37°C

References & Links

Links to other databases for epicatechin

ChEBI
PubChem
-
PubChem