Ligand 4-Hydroxycoumarin

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Basic Ligand Information

Molecular Structure
Picture of 4-Hydroxycoumarin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H6O3
4-Hydroxycoumarin
VXIXUWQIVKSKSA-UHFFFAOYSA-N
Synonyms:
4-hydroxy-2H-chromen-2-one, 4-hydroxycoumarine, coumarol
Pathway Source
Pathways
MetaCyc
4-hydroxycoumarin and dicoumarol biosynthesis

Roles as Enzyme Ligand

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
malonyl-CoA + 2-hydroxybenzoyl-CoA = 2 CoA + 4-hydroxycoumarin + CO2
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (1 result)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDPglucose + 4-hydroxycoumarine = UDP + 4-hydroxycoumaryl beta-D-glucoside
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (4 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
3 malonyl-CoA + salicyl-CoA = 4 CoA + 4-hydroxy-2H-chromen-2-one + 3 CO2
show the reaction diagram
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malonyl-CoA + 2-hydroxybenzoyl-CoA = 2 CoA + 4-hydroxycoumarin + CO2
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (9 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
weak inhibition
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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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reversible time-independent inhibition. Only dicoumarol, 4-hydroxycoumarin and warfarin inhibit in micromolar ranges. 7-Hydroxy-4-methylcoumarin is ineffective. Competitive inhibition with respect to 2,6-dichlorophenolindophenol, uncompetitive with respect to NADPH. Phenolic hydroxyl group at the C-4 position in the coumarin skeleton is important for the maximal inhibition. Sequence of potency for the inhibitors in descending order: dicoumarol, 4-hydroxycoumarin, warfarin, coumarin
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IC50: 0.57 mM
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Enzyme Kinetic Parameters

Ki Value (1 result)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
7.3
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with Ac-Arg-Val-Arg-Arg-4-nitroanilide as substrate

IC50 Value (4 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0781
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pH 7.0, 37°C, versus xanthine
0.57
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IC50: 0.57 mM

References & Links

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Links to other databases for 4-Hydroxycoumarin

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ChEBI
PubChem
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PubChem