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BRENDA support

Ligand (+)-catechin

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Basic Ligand Information

Molecular Structure
Picture of (+)-catechin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H14O6
(+)-catechin
PFTAWBLQPZVEMU-DZGCQCFKSA-N
Synonyms:
(2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol, (2R,3S)-2-(3,4-dihydroxyphenyl)-3,4-dihydro-2H-chromene-3,5,7-triol, (2R,3S)-catechin, (RS)-catechin, 2,3-(trans)-(+)-catechin, 2,3-trans-catechin, catechin, D-catechin, p-catechuic 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
2,3-(trans)-(+)-catechin + [reduced NADPH-hemoprotein reductase] + O2 = 2,3-(trans)-(+)-gallocatechin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
catechin + O2 = ? + 2 H2O
show the reaction diagram
-
(2R,3S)-catechin + NADP+ + H2O = 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (3 results)

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

Substrate in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
D-catechin + O2 = ?
show the reaction diagram
-
catechin + O2 = ?
show the reaction diagram
-
2,3-(trans)-(+)-catechin + [reduced NADPH-hemoprotein reductase] + O2 = 2,3-(trans)-(+)-gallocatechin + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
(+)-catechin + 2-oxoglutarate + O2 = cyanidin + succinate + CO2 + 2 H2O
show the reaction diagram
-
phosphoric acid swollen cellulose + catechin + O2 = cello-oligosaccharides + ? + H2O
show the reaction diagram
-
(2R,3S)-catechin + NADP+ + H2O = 2,3-trans-3,4-cis-leucocyanidin + NADPH + H+
show the reaction diagram
UDP-alpha-D-glucose + catechin = UDP + ?
show the reaction diagram
-
sucrose + (+)-catechin = D-fructose + (+)-catechin-3'-O-alpha-D-glucopyranoside
show the reaction diagram
-
3'-phosphoadenylylsulfate + catechin = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
-
catechin + H2O = ?
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (12 results)

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

Inhibitor in Enzyme-catalyzed Reactions (47 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
competitive, IC50 value 0.078 mg/ml
-
competitive inhibition of the LOX/4-nitroso-N,N-dimethylaniline reaction
-
inhibits at lower concentration
-
0.5 mM, 50% inhibition
-
from green tea, Camellia sinensis, is specific for SRD5alpha1 inhibition
-
slightly, catechin, non-competitive with both NADPH and GSSG, influence on glutathione recognition
-
50% inhibition of overall enzyme reaction at 1.6 mM, 50% inhibition of ketoacyl reduction reaction at 7.4 mM
-
poorest inhibitor tested, 0.1 mM, 1.6fold inhibition of isoform SNAT1 at 0.1 mM
-
a coumaroflavan from Treculia africana, 26% total inhibition at 0.033 mM
-
IC50: 0.44 mM
-
catechin shows 43.6% inhibitory effect at 0.2 mg/ml
-
reaches 50% inhibition at concentrations of 2.5 mM
-
a flavonol, 0.888 mM, pH 6.0, room temperature, 13.1% maximum inhibition
-
noncompetitive inhibition
-
noncompetitive
-
0.5 mM, 30°C, pH 6.8, 81.5% inhibition
-
0.1 mM, about 40% inhibition
-
a competitive inhibitor with 4-nitrophenylacetate as substrate
-

3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

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

KM Value (18 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.014
-
pH 7.5, 38°C
0.175
-
pH 6.0, 37°C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
13.6
-
-

IC50 Value (27 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00122
-
pH 7.0, 23°C
0.0045
-
pH 7.5, 22°C
0.164
-
at pH 7.4 and 37°C
0.44
-
IC50: 0.44 mM
0.2
-
above, pH 6.8, 30°C
0.0368
-
30°C, pH 6.8
0.046
-
-

References & Links

Links to other databases for (+)-catechin

ChEBI
PubChem
ChEBI
PubChem