Ligand coumarin

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Basic Ligand Information

Molecular Structure
Picture of coumarin (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C9H6O2
coumarin
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N
Synonyms:
1,2-benzopyrone, 2H-1-benzopyran-2-one, 2H-chromen-2-one, Coumarine

Roles as Enzyme Ligand

Substrate in Enzyme-catalyzed Reactions (1 result)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE
show the reaction diagram
coumarin + [reduced NADPH-hemoprotein reductase] + O2 = ? + [oxidized NADPH-hemoprotein reductase] + H2O

Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
LITERATURE
REACTION DIAGRAM
REACTION
ENZYME 3D STRUCTURE

Activator in Enzyme-catalyzed Reactions (2 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (14 results)

COMMENTARY
EC NUMBER
LITERATURE
ENZYME 3D STRUCTURE
slight
-
anticoagulants
-
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
-
IC50: 2.8 mM
-
uncompetitive inhibition
-
about 17% inhibition at 0.01 mM
-
IC50 ketonase reaction 88.8 microM, pH 6.5, room temperatur
-

3D Structure of Enzyme-Ligand-Complex (PDB) (22 results)

Enzyme Kinetic Parameters

Ki Value (20 results)

COMMENTARY
EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
LITERATURE
pH 7.0, 30°C
0.4203
-
inhibition of isozyme hCA I, pH not specified in the publication, temperature not specified in the publication
0.0001
-
isozyme hCAII, pH 7.5, 22°C
0.0092
-
isozyme hCAI, pH 7.5, 22°C
0.0031
-
isoform CA IV, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.0622
-
isoform CA II, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.0092
-
isoform CA I, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.0031
-
inhibition of isozyme hCA XII, pH not specified in the publication, temperature not specified in the publication
0.0031
-
inhibition of isozyme hCA IX, pH not specified in the publication, temperature not specified in the publication
0.0092
-
inhibition of isozyme hCA II, pH not specified in the publication, temperature not specified in the publication
0.0001
-
above, isozyme hCAIX, pH 7.5, 22°C
1
-
IC50 above 0.5 mM, isoform CA XIV, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.5
-
IC50 above 0.5 mM, isoform CA XII, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.5
-
IC50 above 0.5 mM, isoform CA VII, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.5
-
IC50 above 0.5 mM, isoform CA VI, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.5
-
IC50 above 0.5 mM, isoform CA VB, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.5
-
IC50 above 0.5 mM, isoform CA VA, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.5
-
IC50 above 0.5 mM, isoform CA IX, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.5
-
IC50 above 0.5 mM, isoform CA III, in 20 m M HEPES (pH 7.5), and 20 mM Na2SO4, at 22°C
0.5
-
above, isozyme hCAXII, pH 7.5, 22°C
1
-

IC50 Value (4 results)

COMMENTARY
EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
LITERATURE
ALR1, pH not specified in the publication, temperature not specified in the publication
0.5
-
ALR2, pH not specified in the publication, temperature not specified in the publication
0.4
-
IC50: 2.8 mM
2.8
-
IC50 ketonase reaction 88.8 microM, pH 6.5, room temperatur
0.0888
-

References & Links

Links to other databases for coumarin

ChEBI
PubChem
-
PubChem