Ligand daidzein

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Basic Ligand Information

Molecular Structure
Picture of daidzein (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H10O4
daidzein
KCWZGJVSDFYRIX-YFKPBYRVSA-N
Synonyms:
3-(4-hydroxyphenyl)-7-hydroxy-chromen-4-one, 4',7-dihydroxy-isoflavone, 4',7-dihydroxyflavanone, 7,4'-dihydroxyisoflavone, 7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
daidzein + NADPH + O2 = 2'-hydroxydaidzein + NADP+ + H2O
show the reaction diagram
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daidzein + NADPH + H+ + O2 = 2'-hydroxydaidzein + NADP+ + H2O
show the reaction diagram
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daidzein + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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daidzein + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone = S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
show the reaction diagram
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UDP-glucose + daidzein = UDP + daidzein 7-O-beta-D-glucoside
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
daidzin + H2O = daidzein + beta-D-glucopyranose
show the reaction diagram
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daidzein 7-O-beta-D-glucopyranoside + H2O = daidzein + beta-D-glucose
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (25 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
daidzein + H2O2 = 6-hydroxydaidzein + H2O
show the reaction diagram
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daidzein + NADPH + O2 = 2'-hydroxydaidzein + NADP+ + H2O
show the reaction diagram
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daidzein + [reduced NADPH-hemoprotein reductase] + O2 = 3'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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daidzein + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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daidzein + [reduced NADPH-hemoprotein reductase] + O2 = 2'-hydroxydaidzein + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
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S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone = S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
show the reaction diagram
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S-adenosyl-L-methionine + 4',7-dihydroxyflavanone = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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S-adenosyl-L-methionine + daidzein = S-adenosyl-L-homocysteine + formononetin
show the reaction diagram
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S-adenosyl-L-methionine + daidzein = ?
show the reaction diagram
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S-adenosyl-L-methionine + 7,4'-dihydroxyisoflavone = S-adenosyl-L-homocysteine + 4'-hydroxy-7-methoxyisoflavone
show the reaction diagram
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UDP-glucose + daidzein = UDP + daidzein 7-O-beta-D-glucoside
show the reaction diagram
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3'-phosphoadenylylsulfate + daidzein = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3'-phosphoadenylylsulfate + daidzein = adenosine 3',5'-bisphosphate + ?
show the reaction diagram
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3'-phosphoadenylylsulfate + daidzein = adenosine 3',5'-bisphosphate + daidzein sulfate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
liquiritigenin + O2 + [reduced NADPH-hemoprotein reductase] = daidzein + 2 H2O + [oxidized NADPH-hemoprotein reductase]
show the reaction diagram
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daidzein 7-O-beta-D-glucopyranoside + H2O = daidzein + beta-D-glucose
show the reaction diagram
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daidzin + H2O = daidzein + beta-D-glucopyranose
show the reaction diagram
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daidzein 7-O-beta-D-glucuronide + H2O = daidzein + D-glucuronate
show the reaction diagram
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daidzin + H2O = beta-D-glucose + daidzein
show the reaction diagram
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2,7,4'-trihydroxyisoflavanone = daidzein + H2O
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
slight activation
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Inhibitor in Enzyme-catalyzed Reactions (32 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibition of isoenzyme BB-ADH, no inhibition of isoenzyme AA-ADH and TT-ADH
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isoflavone, isolated and purified from korean soybean paste, structural analysis
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noncompetitive
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soy isoflavones at hormonally active concentrations cause a significant reduction of both COMT mRNA levels and COMT activity as well as of the methylation of 4-hydroxyestradiol
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IC50: 0.0732 mM
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inhibition of isozymes GST A1-1, M1-1, and P1-1
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isolated from Psoralea corylifolia, slight inhibition
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IC50: 0.008 mM, competitive
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IC50: 0.0286 mM, PDE3
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a isoflavone, 0.888 mM, pH 6.0, room temperature, 23.3% maximum inhibition
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mixed type
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enzyme is a major daidzein-binding protein
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weak
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IC50: 0.0038 mM
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (15 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
0.08
-
pH 8.8, 30°C
0.1673
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pH 7.4, 37°C

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.002
-
-
0.0038
-
pH 7.3, 37°C

IC50 Value (13 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.01
-
in 0.1 M potassium phosphate, pH 7.4
0.01
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IC50: 0.01 mM
0.157
-
pH 7.4, 27°C
0.02455
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pH 7.0 and 37°C
0.0732
-
IC50: 0.0732 mM
0.008
-
IC50: 0.008 mM, competitive
0.0286
-
IC50: 0.0286 mM, PDE3
0.014
-
pH 6.8, 30°C
0.1059
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at pH 2.0 and 37°C
0.0079
-
pH 8.2, 30°C
0.0038
-
IC50: 0.0038 mM

References & Links

Links to other databases for daidzein

ChEBI
PubChem
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PubChem