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Ligand quercetin 3-O-glucoside

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Basic Ligand Information

Molecular Structure
Picture of quercetin 3-O-glucoside (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C21H20O12
quercetin 3-O-glucoside
OVSQVDMCBVZWGM-QSOFNFLRSA-N
Synonyms:
2-(3',4'-dihydroxyphenyl)-5,7-dihydroxy-3-beta-D-glucosyl-4H-chromen-4-one, isoquercetin, isoquercitrin, isoquercitrin-glucoside, isoquercitrin glucoside, quercetin-3-beta-D-glucopyranoside, quercetin-3-beta-D-glucoside, quercetin-3-beta-glucopyranoside, quercetin-3-glucopyranoside, quercetin-3-glucoside, quercetin-3-O-beta-D-glucoside, quercetin-3-O-beta-glucopyranosyl, quercetin 3'-O-beta-D-glucoside, quercetin 3-beta-D-glucoside, quercetin 3-O-beta-D-glucoside
Pathway Source
Pathways
KEGG
Biosynthesis of secondary metabolites, Flavone and flavonol biosynthesis
MetaCyc
flavonol acylglucoside biosynthesis III - quercetin derivatives, quercetin gentiotetraside biosynthesis, quercetin glucoside biosynthesis (Allium), quercetin glycoside biosynthesis (Arabidopsis), quercetin triglucoside biosynthesis more

Roles as Enzyme Ligand

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

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
isoquercitrin + H2O = quercetin + beta-D-glucose
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (1 result)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-alpha-D-glucose + quercetin = UDP + quercetin 3-O-beta-D-glucoside
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (32 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
S-adenosyl-L-methionine + quercetin 3-O-beta-D-glucoside = S-adenosyl-L-homocysteine + 4'-methoxyquercetin 3-O-beta-D-glucoside
show the reaction diagram
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S-adenosyl-L-methionine + quercetin 3-O-beta-D-glucoside = S-adenosyl-L-homocysteine + isorhamnetin 3-O-beta-D-glucoside
show the reaction diagram
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S-adenosyl-L-methionine + quercetin 3-O-glucoside = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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malonyl-CoA + quercetin 3-O-beta-D-glucoside = CoA + quercetin 3-O-(6-O-malonyl-beta-D-glucoside)
show the reaction diagram
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UDP-glucose + quercetin 3-O-beta-D-glucoside = UDP + quercetin 3-O-beta-D-glucosyl-(1-2)-beta-D-glucoside
show the reaction diagram
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UDP-alpha-D-glucose + quercetin 3-O-beta-D-glucoside = UDP + quercetin 3-O-sophoroside
show the reaction diagram
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UDP-alpha-D-glucose + quercetin 3-O-beta-D-glucoside = UDP + quercetin 3,5-di-O-beta-D-glucoside
show the reaction diagram
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UDP-L-rhamnose + quercetin 3-O-beta-D-glucoside = UDP + quercetin 3-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]
show the reaction diagram
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UDP-glucose + quercetin 3-O-glucoside = UDP + quercetin 3-O-beta-D-glucosyl-(1->6)-beta-D-glucoside
show the reaction diagram
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3'-phosphoadenylyl sulfate + isoquercitrin = adenosine 3',5'-bisphosphate + isoquercitrin 4'-O-sulfate
show the reaction diagram
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4-nitrophenyl sulfate + isoquercetin = 4-nitrophenol + isoquercetin 4'-O-sulfate
show the reaction diagram
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quercetin-3-glucoside + H2O = quercetin + D-glucose
show the reaction diagram
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quercetin-3-glucoside + H2O = quercetin + D-glucose
show the reaction diagram
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isoquercitrin + H2O = quercetin + beta-D-glucose
show the reaction diagram
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isoquercitrin + H2O = quercetin + beta-D-glucose
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (19 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-alpha-D-glucose + quercetin = UDP + quercetin 3-O-beta-D-glucoside
show the reaction diagram
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UDP-glucose + quercetin = UDP + quercetin 3-O-beta-D-glucoside
show the reaction diagram
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UDP-alpha-D-glucose + quercetin = UDP + quercetin 7-O-beta-D-glucoside + quercetin 3-O-beta-D-glucoside
show the reaction diagram
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UDP-alpha-D-glucose + quercetin = UDP + quercetin 3'-O-beta-D-glucoside + quercetin 7-O-beta-D-glucoside + quercetin 7,3'-di-O-beta-D-glucoside
show the reaction diagram
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ADP-alpha-D-glucose + quercetin = ADP + isoquercitrin
show the reaction diagram
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UDP-alpha-D-glucose + quercetin = UDP + quercetin 3-O-beta-D-glucoside
show the reaction diagram
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rutin + H2O = isoquercitrin + alpha-L-rhamnose
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (17 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50: 0.0015 mM
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IC50: 0.108 mM
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PI 3-kinase I and PI 3-kinase II; strong inhibition of PI 3-kinase I and II, noncompetitive, apparent Ki value: 4 mM for PI 3-kinase I and 2.5 mM for PI 3-kinase II
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41.8% inhibition at 0.03 mM
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0.05 mM, 57.5% inhibition
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flavonoid in Helichrysum pamphylicum
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.014
-
pH 7.0, 30°C
6.3
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pH 6, 37°C
6.3
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pH 6, 37°C
53.3
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pH 5.0, 95°C
53.3
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pH 5.0, 09°C, recombinant enzyme

KM Value (8 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.437
-
pH 7.0, 30°C
4.51
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pH 8.0, 35°C
0.046
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pH 6, 37°C
0.046
-
pH 6, 37°C
0.17
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pH 5.0, 95°C

Ki Value (1 result)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.025
-
-

IC50 Value (9 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0015
-
IC50: 0.0015 mM
0.108
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IC50: 0.108 mM
0.02
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pH 7.4, 37°C, isozyme sPLA2 IB
0.0185
-
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0.049
-
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0.16
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pH 6.0, 37°C
0.014
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at pH 7.4 and 25°C

References & Links

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Links to other databases for quercetin 3-O-glucoside

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ChEBI
PubChem
ChEBI
PubChem