Ligand naringenin chalcone

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Basic Ligand Information

Molecular Structure
Picture of naringenin chalcone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H12O5
naringenin chalcone
YQHMWTPYORBCMF-ZZXKWVIFSA-N
Synonyms:
(2E)-3-(4-hydroxyphenyl)-1-(2,4,6-trihydroxyphenyl)prop-2-en-1-one, 2',4',6',4-tetrahydroxy chalcone, 2',4',6',4-tetrahydroxychalcone, 2',4,4',6'-tetrahydroxychalcone, chalconaringenin, trans-2',4,4',6'-tetrahydroxychalcone

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (6 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
2',4',6',4-tetrahydroxychalcone + O2 = aureusidin + H2O
-
show the reaction diagram
dimethylallyl diphosphate + naringenin chalcone = diphosphate + desmethylxanthohumol
-

In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
(2S)-naringenin = naringenin chalcone
-

Substrate in Enzyme-catalyzed Reactions (12 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
naringenin chalcone + 2-oxoglutarate + O2 = eriodictyol chalcone
-
show the reaction diagram
2',4',6',4-tetrahydroxychalcone + O2 = aureusidin + H2O
-
show the reaction diagram
S-adenosyl-L-methionine + chalconaringenin = S-adenosyl-L-homocysteine + ?
-
show the reaction diagram
UDP-glucuronate + 2',4,4',6'-tetrahydroxychalcone = ?
-
show the reaction diagram
UDPglucose + 2',4',6',4-tetrahydroxychalcone = UDP + 2',4',6',4-tetrahydroxychalcone 4'-O-glucoside
-
show the reaction diagram
UDP-alpha-D-glucose + 2',4,4',6'-tetrahydroxychalcone = UDP + 2',4,4',6'-tetrahydroxychalcone 4'-O-beta-D-glucoside
-
show the reaction diagram
dimethylallyl diphosphate + naringenin chalcone = diphosphate + desmethylxanthohumol
-

Product in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (3 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
0.1 mM
-
50% inhibition of naringenin formation and total inhibition of eriodictyol formation
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (17 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
mutant enzyme M96K, at pH 7.6 and 25°C
7.8
-
wild type enzyme, at pH 7.6 and 25°C
130.3
-
wild type enzyme, at pH 6.4, temperature not specified in the publication
1142
-
mutant enzyme Y48F, at pH 6.4, temperature not specified in the publication
784
-
mutant enzyme Y116A, at pH 7.6 and 25°C
9.6
-
mutant enzyme S189T, at pH 7.6 and 25°C
228.2
-
mutant enzyme S189A, at pH 7.6 and 25°C
5
-
mutant enzyme R125A, at pH 6.4, temperature not specified in the publication
1379
-
mutant enzyme Q104E, at pH 7.6 and 25°C
134.7
-
-
2300
-
mutant enzyme M36A, at pH 7.6 and 25°C
35.2
-
mutant enzyme K108A, at pH 7.6 and 25°C
56.9
-
mutant enzyme I190M, at pH 7.6 and 25°C
197.7
-
mutant enzyme H73A, at pH 6.4, temperature not specified in the publication
1313
-
mutant enzyme H33Q, at pH 6.4, temperature not specified in the publication
0.07
-
mutant enzyme H33E, at pH 6.4, temperature not specified in the publication
0.2
-
mutant enzyme H33A, at pH 6.4, temperature not specified in the publication
0.6
-

KM Value (20 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
pH 6.6
0.0043
-
pH 7.5, 30°C
0.237
-
-
0.13
-
mutant enzyme Q104E, at pH 7.6 and 25°C
0.0061
-
wild type enzyme, at pH 7.6 and 25°C
0.0085
-
wild type enzyme, at pH 6.4, temperature not specified in the publication
0.354
-
mutant enzyme Y48F, at pH 6.4, temperature not specified in the publication
0.0143
-
mutant enzyme Y116A, at pH 7.6 and 25°C
0.007
-
mutant enzyme S189T, at pH 7.6 and 25°C
0.0099
-
mutant enzyme S189A, at pH 7.6 and 25°C
0.0024
-
mutant enzyme R125A, at pH 6.4, temperature not specified in the publication
0.0567
-
mutant enzyme M96K, at pH 7.6 and 25°C
0.0105
-
mutant enzyme M36A, at pH 7.6 and 25°C
0.0048
-
mutant enzyme K108A, at pH 7.6 and 25°C
0.0048
-
mutant enzyme I190M, at pH 7.6 and 25°C
0.0086
-
mutant enzyme H73A, at pH 6.4, temperature not specified in the publication
0.0439
-
mutant enzyme H33Q, at pH 6.4, temperature not specified in the publication
0.0798
-
mutant enzyme H33E, at pH 6.4, temperature not specified in the publication
0.1319
-
mutant enzyme H33A, at pH 6.4, temperature not specified in the publication
0.0203
-
-
0.043
-

References & Links

Links to other databases for naringenin chalcone

ChEBI
PubChem
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PubChem