Ligand dihydroquercetin

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Basic Ligand Information

Molecular Structure
Picture of dihydroquercetin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C15H12O7
dihydroquercetin
CXQWRCVTCMQVQX-UHFFFAOYSA-N
Synonyms:
(+-)-taxifolin, (+/-)-dihydroquercetin, (+/-)-taxifolin, 2,3-dihydroquercetin, dihydro-3,3',4',5,7-pentahydroxy flavone, guaijaverin, rac-taxifolin
Pathway Source
Pathways
KEGG
Biosynthesis of phenylpropanoids, Biosynthesis of secondary metabolites, Flavonoid biosynthesis

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (5 results)

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

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

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EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
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show the reaction diagram
dihydrokaempferol + [reduced NADPH-hemoprotein reductase] + O2 = dihydroquercetin + [oxidized NADPH-hemoprotein reductase] + H2O
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-
show the reaction diagram
dihydrokaempferol + [reduced NADPH-hemoprotein reductase] + O2 = dihydroquercetin + [oxidized NADPH-hemoprotein reductase] + H2O
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Substrate in Enzyme-catalyzed Reactions (24 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
S-adenosyl-L-methionine + dihydroquercetin = S-adenosyl-L-homocysteine + ?
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show the reaction diagram
S-adenosyl-L-methionine + dihydro-3,3',4',5,7-pentahydroxy flavone = S-adenosyl-L-homocysteine + dihydroisorhamnetin
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show the reaction diagram
adenosine 3'-phosphate 5'-phosphosulfate + dihydroquercetin = adenosine 3',5'-bisphosphate + dihydroquercetin 7-sulfate
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Product in Enzyme-catalyzed Reactions (6 results)

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EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
dihydrokaempferol + [reduced NADPH-hemoprotein reductase] + O2 = dihydroquercetin + [oxidized NADPH-hemoprotein reductase] + H2O
-
-
show the reaction diagram
dihydrokaempferol + [reduced NADPH-hemoprotein reductase] + O2 = dihydroquercetin + [oxidized NADPH-hemoprotein reductase] + H2O
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-
show the reaction diagram
eriodictyol + 2-oxoglutarate + O2 = dihydroquercetin + luteolin + succinate + CO2 + 2 H2O
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Inhibitor in Enzyme-catalyzed Reactions (9 results)

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COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
60% inhibition at 0.01 mM
-
0.025 mM
-
50% inhibition at 0.041163 mM
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IC50: 0.08 mM
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0.1 mM, about 25% inhibition
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i.e. (2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-2,3-dihydro-4H-1-benzopyran-4-one
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (9 results)

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COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
pH 6.3, temperature not specified in the publication
3.1
-
mutant E295Q, 37°C
0.015
-
mutant F134L, 37°C
0.019
-
mutant H132F, 37°C
0.034
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mutant H132Y, 37°C
0.03
-
mutant S289T, 37°C
0.024
-
pH 7.5, 30°C
0.16
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recombinant FLS1, pH not specified in the publication, temperature not specified in the publication
3.9
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wild-type, 37°C
0.056
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KM Value (14 results)

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COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
pH 6.3, temperature not specified in the publication
0.0004
-
pH 7.0, 30°C
0.002
-
-
0.272
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in 0.1 M K2HPO4/KH2PO4 (0.6 M sorbitol, 0.4% Na-ascorbate, pH 7.25) with 0.095 nmol dihydrokaempferol, 50 nmol 2-oxoglutarate and 10 nmol FeSO4 hydrate at 30°C
0.0012
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mutant E295Q, 37°C
0.07
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mutant F134L, 37°C
0.129
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mutant H132F, 37°C
0.027
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mutant H132Y, 37°C
0.031
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mutant S289T, 37°C
0.32
-
pH 7.5, 30°C
0.139
-
recombinant FLS1, pH not specified in the publication, temperature not specified in the publication
0.1511
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wild-type, 37°C
0.059
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pH 7.4
0.037
-
-
0.435
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IC50 Value (3 results)

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COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
IC50: 0.08 mM
0.08
-
at 37°C in 10 mM potassium phosphate buffer, pH 7.4, containing 0.05% (w/v) emulphogen
0.0195
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pH 6.0, 37°C
0.12
-

References & Links

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Links to other databases for dihydroquercetin

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ChEBI
PubChem
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PubChem