Ligand hesperetin

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Basic Ligand Information

Molecular Structure
Picture of hesperetin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C16H14O6
hesperetin
AIONOLUJZLIMTK-AWEZNQCLSA-N
Synonyms:
(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydro-4H-chromen-4-one, 4'-methoxyeriodictyol, 4'-methoxy eriodictyol, 5,7,3'-trihydroxy-4'-methoxyflavanone, eriodictoyl-4'-O-methylether, hesperitin
Pathway Source
Pathways

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hesperetin 7-O-beta-glucopyranoside + H2O = hesperetin + beta-D-glucose
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4'-methoxy eriodictyol + 2-oxoglutarate + O2 = ? + succinate + CO2
show the reaction diagram
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hesperetin + 2-oxoglutarate + O2 = 3,5-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-chromen-4-one + succinate + CO2 + H2O
show the reaction diagram
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UDP-D-glucuronate + hesperetin = UDP + hesperetin 7-O-beta-D-glucuronoside
show the reaction diagram
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dimethylallyl diphosphate + hesperetin = diphosphate + sigmoidin B
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
S-adenosyl-L-methionine + eriodictyol = S-adenosyl-L-homocysteine + 4'-methoxyeriodictyol
show the reaction diagram
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hesperetin 7-O-beta-glucopyranoside + H2O = hesperetin + beta-D-glucose
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (16 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 0.09 mM
-
i.e. 3',5,7-trihydroxy-4'-methoxyflavanone, major flavanone component of orange juice, inhibits hepatic XDH activity and decreases serum uric acid levels, exhibits antioxidative and antihyperuricemic properties
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the enzyme activity is reduced by about 75% in the presence of hesperitin
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50% inhibition at 0.06886 mM
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1 mM: 66% inhibition, 0.1 mM: 47% inhibition
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IC50: 0.0282 mM, PDE4
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a flavanone, 0.888 mM, pH 6.0, room temperature, 39.8% maximum inhibition
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slight inhibition
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (2 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.77
-
pH 7.5, 30°C, with UDP-glucose, recombinant enzyme
0.026
-
pH not specified in the publication, 37°C

KM Value (4 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.1
-
pH not specified in the publication, 37°C

IC50 Value (11 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.09
-
IC50: 0.09 mM
0.0074
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25°C, pH 7.4, cell lysate
0.61
-
pH 5.5, 20°C
0.08529
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at pH 7.4 and 37°C
0.1539
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at pH 7.4 and 37°C
0.0282
-
IC50: 0.0282 mM, PDE4
0.15
-
pH 6.8, 30°C

References & Links

Links to other databases for hesperetin

ChEBI
PubChem
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PubChem