Ligand rutin

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Basic Ligand Information

Molecular Structure
Picture of rutin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C27H30O16
rutin
IKGXIBQEEMLURG-UHFFFAOYSA-N
Synonyms:
quercetin 3-O-[alpha-L-rhamnosyl-(1->6)-beta-D-glucoside]

Roles as Enzyme Ligand

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

EC NUMBER
LITERATURE
REACTION DIAGRAM
PROVEN IN VIVO REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
rutin + H2O = quercetin + rutinose
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Substrate in Enzyme-catalyzed Reactions (21 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
rutin + O2 = ?
-
show the reaction diagram
S-adenosyl-L-methionine + rutin = S-adenosyl-L-homocysteine + ?
-
show the reaction diagram
malonyl-CoA + rutin = ?
-
show the reaction diagram
starch + rutin = glycosyl rutin
-
show the reaction diagram
UDP-glucose + rutin = UDP + rutin 7-O-beta-D-glucoside
-
show the reaction diagram
UDPglucose + rutin = UDP + rutin 3-O-glucoside
-
show the reaction diagram
3'-phosphoadenylyl sulfate + rutin = adenosine 3',5'-bisphosphate + rutin 4'-O-sulfate
-
show the reaction diagram
maltose + rutin = ?
-
show the reaction diagram
rutin + H2O = ?
-
show the reaction diagram
rutin + H2O = quercetin + rutinose
-
show the reaction diagram
rutin + H2O = quercetin + rutinose
-

Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
-
show the reaction diagram
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
isorhamnetin 3-O-rutinoside + H2O = isorhamnetin + rutin
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Activator in Enzyme-catalyzed Reactions (1 result)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
significantly increases serum xanthine oxidase activities
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Inhibitor in Enzyme-catalyzed Reactions (36 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
IC50 0.06 mM
-
competitive
-
binding structure at the substrate binding site
IC50: 1 mM
-
IC50: 0.033 mM
-
tyrosinase inhibitors from Marrubium velutinum, flavone/flavonol glucosides
-
at 0.01 mM, 52% inhibition of 0.1 mM substrate benzaldehyde, 27% inhibition of 0.05 mM substrate phenanthridine, 34% inhibition of 0.05 mM substrate vanillin. Mixed type inhibition for benzaldehyde and vanillin, non-competitive with phenanthridine
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slightly, flavonol glycoside, non-competitive with both NADPH and GSSG, influence on glutathione recognition
-
50% inhibition at 0.07 mM
-
IC50: 0.32 mM
-
noncompetitive inhibitor, i.e. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one, about 20% residual activity at 0.02-0.06 mM rutin
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61.87% inhibition at 0.2 mM
-
slight inhibition
-
competitve inhibition, structually related to glutathione, Dixon plot analysis, significantly lower inhibition than that with curcumin, pH 7.0, 30°C, results in a decrease of D-lactate release
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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) (4 results)

COMMENTARY
EC NUMBER
LITERATURE
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
pH 5.0, 50°C
550
-
pH 6.9, 37°C
18.2
-
pH 5.0, 09°C, recombinant enzyme
0.026
-
pH 5.0, 95°C
0.027
-

KM Value (11 results)

COMMENTARY
EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
LITERATURE
isoform RhaB1
1.77
-
isoform RhaB2
1.06
-
pH 5.0, 50°C
0.39
-
pH 6.9, 37°C
0.031
-
30°C, pH not specified in the publication
0.561
-
pH 5.0, 09°C, recombinant enzyme
0.34
-
pH 5.0, 37°C, isoenzyme f3gI
0.115
-
pH 5.0, 37°C, isoenzyme f3gII
0.125
-
pH 5.0, 95°C
0.34
-

Ki Value (6 results)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
pH 7.0, 37°C, substrate benzaldehyde
0.001
-
pH 7.0, 37°C, substrate vanillin
0.00092
-
in the presence of increasing amounts of inhibitor at different concentrations of the substrates methylglyoxal and glutathione, Dixon plot analysis, significantly lower inhibition than that with curcumin, competitive inhibition, pH 7.0, 30°C
0.14
-

IC50 Value (20 results)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
pH and temperature not specified in the publication
0.06
-
IC50 0.06 mM
0.06
-
wild-type, pH 7.4, 37°C
0.0018
-
pH 7.4, 37°C
0.0021
-
at pH 8.4 and 37°C
0.00074
-
mutant D218V, pH 7.4, 37°C
0.0014
-
pH 6.4, 24°C
0.01
-
pH 7.0, 23°C
0.036
-
IC50: 1 mM
1
-
IC50: 0.033 mM
0.033
-
the effect of the formosan apple constituents on hydroxyl radical-scavenging activity
0.08
-
pH 7.0 and 37°C
0.0271
-
pH 7.5, 22°C
0.057
-
at pH 8.0 and 30°C
0.0103
-
pH and temperature not specified in the publication
0.042
-
IC50: 0.32 mM
0.32
-
56.1% inhibition at 0.1 mM
0.091
-
-
0.196
-
pH not specified in the publication, 37°C
0.472
-
37°C, pH not specified in the publication
0.472
-

References & Links

Links to other databases for rutin

ChEBI
PubChem
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PubChem