Ligand isoliquiritigenin

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Basic Ligand Information

Molecular Structure
Picture of isoliquiritigenin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H12O4
isoliquiritigenin
DXDRHHKMWQZJHT-FPYGCLRLSA-N
Synonyms:
(2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one, (2E)-1-(2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one, 2',4',4-trihydroxy-4'-chalcone, 2',4,4'-trihydroxychalcone, 4,2',4'-trihydroxychalcone, iso-liquiritigenin

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
S-adenosyl-L-methionine + isoliquiritigenin = S-adenosyl-L-homocysteine + 2'-O-methylisoliquiritigenin
show the reaction diagram

In Vivo Product in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ = CoA + isoliquiritigenin + CO2 + NADP+ + H2O
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
isoliquiritigenin + 2-oxoglutarate + O2 = butein + succinate + CO2
show the reaction diagram
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isoliquiritigenin + O2 = sulfuretin + H2O
show the reaction diagram
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S-adenosyl-L-methionine + isoliquiritigenin = S-adenosyl-L-homocysteine + 2'-O-methylisoliquiritigenin
show the reaction diagram
S-adenosyl-L-methionine + isoliquiritigenin = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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S-adenosyl-L-methionine + isoliquiritigenin = S-adenosyl-L-homocysteine + 2'-O-methylisoliquiritigenin
show the reaction diagram
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2',4,4'-trihydroxychalcone + UDP-glucuronate = UDP + 2',4,4'-trihydroxychalcone 4'-O-glucoside + 2',4,4'-trihydroxychalcone 2'-O-glucoside
show the reaction diagram
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UDP-alpha-D-glucose + isoliquiritigenin = UDP + isoliquiritigenin 7-O-beta-D-glucoside
show the reaction diagram
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UDP-alpha-D-glucose + isoliquiritigenin = UDP + isoliquiritin
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
malonyl-CoA + 4-coumaroyl-CoA + NADPH + H+ = CoA + isoliquiritigenin + CO2 + NADP+ + H2O
show the reaction diagram
-
liquiritigenin = isoliquiritigenin
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 0.0338 mM
-
mixed-type, IC50: 0.047
-
IC50: 0.0088 mM
-
isolated from the CH2Cl2 extract of Glycyrrhiza inflata
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strong inhibitory activity, noncompetitive inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (2 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (17 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
4.35
-
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C

KM Value (26 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0039
-
pH 7.5, 30°C
0.0025
-
pH 6.6
2.2
-
-
0.0024
-
with UDP-alpha-D-glucose as cosubstrate, at pH 7.5 and 30°C

IC50 Value (8 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0338
-
IC50: 0.0338 mM
0.047
-
mixed-type, IC50: 0.047 mM
0.0088
-
IC50: 0.0088 mM
0.0964
-
at pH 7.4 and 37°C
0.05
-
above, pH 6.0, 37°C
0.009
-
-

References & Links

Links to other databases for isoliquiritigenin

ChEBI
PubChem
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PubChem