Ligand scopoletin

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Basic Ligand Information

Molecular Structure
Picture of scopoletin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H8O4
scopoletin
RODXRVNMMDRFIK-UHFFFAOYSA-N
Synonyms:
6-methoxy-7-hydroxycoumarin, 7-hydroxy-6-methoxycoumarin, beta-methylesculetin, scopeletin

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
scopoletin + 2-oxoglutarate + O2 = fraxetin + succinate + CO2
show the reaction diagram
-
UDP-glucose + scopoletin = UDP + scopolin
show the reaction diagram
-
UDP-glucose + scopoletin = UDP + scopolin
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

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

Substrate in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
scopoletin + H2O2 = ?
show the reaction diagram
-
scopoletin + 2-oxoglutarate + O2 = fraxetin + succinate + CO2
show the reaction diagram
-
N6-(2-isopentenyl)adenine + scopoletin = adenine + 3-methylbut-2-enal + ?
show the reaction diagram
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S-adenosyl-L-methionine + scopoletin = S-adenosyl-L-homocysteine + ?
show the reaction diagram
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UDP-glucose + scopoletin = UDP + scopolin
show the reaction diagram
-
UDPglucose + scopoletin = UDP + 4-O-beta-D-glucosyl-scopoletin
show the reaction diagram
-
UDP-glucose + scopoletin = UDP + scopolin
show the reaction diagram
-
UDP-glucose + scopoletin = UDP + scopoletin 7-O-beta-D-glucoside
show the reaction diagram
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UDP-glucose + scopoletin = UDP + scopoletin 7-O-beta-D-glucoside
show the reaction diagram
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UDPglucose + scopoletin = UDP + scopoletin beta-D-glucoside
show the reaction diagram
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UDP-alpha-D-glucose + scopoletin = UDP + 6-methoxy-2-oxo-2H-1-benzopyran-7-yl beta-D-glucopyranoside
show the reaction diagram
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UDP-alpha-D-glucose + scopoletin = UDP + ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (3 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
aesculetin + S-adenosyl-L-methionine = scopoletin + S-adenosyl-L-homocysteine
show the reaction diagram
-
-

Inhibitor in Enzyme-catalyzed Reactions (11 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
low competitive inhibition and interaction with the molybdopterin region of the enzyme, structure-function relationship of coumarin derivatives in inhibition of the enzyme, structure-based computer-aided molecular modeling, overview
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moderate inhibition, effect on superoxide anion formation is more pronounced than effect on hydrogen peroxide formation or substrate oxidation
-
73.5% inhibition at 1 mM
-
increases the negative cooperativity between the substrate binding sites
-
IC50 ketonase reaction 133.8 microM, pH 6.5, room temperatur
-
16% inhibition at 0.1 mM
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Enzyme Kinetic Parameters

kcat Value (Turnover Number) (6 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
1.73
-
pH 8.0, 31.5°C
1.4
-
pH 6.5, recombinant enzyme

KM Value (21 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.011
-
pH 8.0, 31.5°C
1.4
-
-

IC50 Value (3 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.1338
-
IC50 ketonase reaction 133.8 microM, pH 6.5, room temperatur

References & Links

Links to other databases for scopoletin

ChEBI
PubChem
ChEBI
PubChem