Ligand 4-Methylumbelliferone

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Basic Ligand Information

Molecular Structure
Picture of 4-Methylumbelliferone (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C10H8O3
4-Methylumbelliferone
CRWNKXHVYMVLCY-UHFFFAOYSA-N
Synonyms:
4-methyl-umbelliferol, 4-methyl-umbelliferone, 4-methylumbeliferone, 4-Methylumbelliferol, 7-hydroxy-4-methyl-2H-1-benzopyran-2-one, coumarin-4, Methylumbelliferone, methylumberlliferone

Roles as Enzyme Ligand

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

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate
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4-methylumbelliferyl beta-D-cellobioside + 2 H2O = 4-methylumbelliferol + 2 D-glucose
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4-methylumbelliferyl alpha-L-iduronide + H2O = 4-methylumbelliferone + alpha-L-iduronic acid
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Substrate in Enzyme-catalyzed Reactions (25 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-glucose + 4-methylumbelliferone = UDP + 7-O-glucosyl-4-methylumbelliferone
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UDP-beta-D-glucose + 4-methylumbelliferone = UDP + 4-methylumbelliferyl-beta-D-glucopyranoside
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3'-phosphoadenylylsulfate + 4-methylumbelliferone = adenosine 3',5'-bisphosphate + 4-methylumbelliferone sulfate
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3'-phosphoadenylylsulfate + 4-methylumbelliferol = adenosine 3',5'-bisphosphate + 4-methylumbelliferyl sulfate
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3'-phosphoadenylylsulfate + 4-methylumbelliferol = adenosine 3',5'-bisphosphate + 4-methylumbelliferyl sulfate
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4-methylumbelliferone + H2O = ?
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Product in Enzyme-catalyzed Reactions (400 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
adenosine 3',5'-bisphosphate + 4-methylumbelliferyl sulfate = 3'-phosphoadenylyl sulfate + 4-methylumbelliferone
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4-methylumbelliferyl butyrate + H2O = 4-methylumbelliferol + butyrate
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4-methylumbelliferyl acetate + H2O = 4-methylumbelliferol + acetate
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4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate
show the reaction diagram
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4-methylumbelliferyl acetate + H2O = 4-methylumbelliferol + acetate
show the reaction diagram
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4-methylumbelliferyl acetate + H2O = 4-methylumbelliferone + acetate
show the reaction diagram
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4-methylumbelliferyl thymidine 3'-phosphate + H2O = thymidine 3'-phosphate + 4-methylumbelliferone
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4-methylumbelliferyl phosphate + H2O = 4-methylumbelliferone + phosphate
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4-methylumbelliferyl phosphate + H2O = 4-methylumbelliferone + phosphate
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4-methylumbelliferyl phosphate + H2O = 4-methylumbelliferone + phosphate
show the reaction diagram
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4-methylumbelliferyl phosphate + H2O = 4-methylumbelliferol + phosphate
show the reaction diagram
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4-methylumbelliferyl phosphate + H2O = 4-methylumbelliferone + phosphate
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4-methylumbelliferyl phosphate + H2O = 4-methylumbelliferone + phosphate
show the reaction diagram
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4-methylumbelliferyl-alpha-L-iduronate 2-sulfate + H2O = 4-methylumbelliferol + L-iduronate 2-sulfate
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4-methylumbelliferyl sulfate + H2O = 4-methylumbelliferone + sulfate
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4-methylumbelliferyl sulfate + H2O = 4-methylumbelliferone + sulfate
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4-methylumbelliferyl sulfate + H2O = methylumbelliferone + sulfate
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methylumbelliferyl sulfate + H2O = methylumbelliferone + sulfate
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4-methylumbelliferyl beta-D-glucoside + H2O = D-glucose + 4-methylumbelliferone
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4-methylumbelliferyl alpha-D-mannopyranoside + H2O = 4-methylumbelliferone + alpha-D-mannopyranose
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4-methylumbelliferyl-alpha-D-glucopyranoside 6-phosphate + H2O = alpha-D-glucose 6-phosphate + 4-methylumbelliferone
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4-methylumbelliferyl beta-D-glucoside + H2O = 4-methylumbelliferone + beta-D-glucose
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4-methylumbelliferyl beta-chitotrioside + H2O = 4-methylumbelliferone + chitotriose + chitobiose + 4-methylumbelliferyl N-acetyl-beta-D-glucosaminide
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4-methylumbelliferyl 2-acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-D-glucopyranoside + H2O = 4-methylumbelliferol + 2-acetamido-2-deoxy-3-O-(beta-D-galactopyranosyl)-D-glucopyranose
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4-methylumbelliferyl-beta-D-glucoside + H2O = 4-methylumbelliferone + D-glucose
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4-methylumbelliferyl beta-D-glucoside + H2O = 4-methylumbelliferol + beta-D-glucopyranose
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4-methylumbelliferyl alpha-D-mannopyranosyl-(1->6)-beta-D-mannopyranoside + H2O = 4-methylumbelliferone + alpha-D-mannopyranosyl-(1->6)-beta-D-mannopyranose
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4-methylumbelliferyl-beta-D-glucuronide + H2O = 4-methylumbelliferol + D-glucuronate
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4-methylumbelliferyl tetra N-acetyl-beta-chitotetraoside + H2O = 4-methylumbelliferol + tetra N-acetyl-beta-chitotetraose
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4-methylumbelliferyl-alpha-D-glucoside + H2O = 4-methylumbelliferol + D-glucose
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4-methylumbelliferyl-beta-D-glucoside + H2O = 4-methylumbelliferone + beta-D-glucose
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4-methylumbelliferyl beta-D-glucoside + H2O = 4-methylumbelliferol + D-glucopyranose
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4-methylumbelliferyl-beta-D-N,N'-diacetylchitobioside + H2O = 4-methylumbelliferone + N,N'-diacetylchitobiose
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4-methylumbelliferyl beta-D-N,N'-diacetylchitobioside + H2O = 4-methylumbelliferone + N,N'-diacetylchitobiose
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4-methylumbelliferyl beta-D-mannoside + H2O = 4-methylumbelliferone + beta-D-mannose
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4-methylumbelliferyl-beta-D-glucoside + H2O = 4-methylumbelliferone + beta-D-glucose
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4-methyl-umbelliferyl-beta-D-glucoside = 4-methylumbelliferone + D-glucose
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Glc-beta(1,4)-Glc-beta(1,3)-Glc-methylumbelliferyl + H2O = methylumbelliferone + Glc-beta(1,4)-Glc-beta(1,3)-Glc
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4-methylumbelliferyl alpha-L-fucopyranoside + H2O = 4-methylumbelliferone + L-fucopyranose
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4-methylumbelliferyl mannotrioside + H2O = 4-methylumbelliferone + mannotriose
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4-methylumbelliferyl-2-acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-beta-D-glucose + H2O = 4-methylumbelliferone + 2-acetamido-3-O-(D-1-carboxyethyl)-2-deoxy-beta-D-glucose
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L-Leu-4-methylumbelliferyl + H2O = L-leucine + 4-methylumbelliferol
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4-methylumbelliferyl-4-guanidinobenzoate + H2O = 4-methylumbelliferol + 4-guanidinobenzoate
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4-methylumbelliferyl acetate + H2O = 4-methylumbelliferol + acetate
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4-methylumbelliferyl-alpha-N-acetylneuraminic acid + H2O = 4-methylumbelliferone + 2,7-anhydro-alpha-N-acetylneuraminic acid
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Inhibitor in Enzyme-catalyzed Reactions (10 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
80.9% inhibition at 1 mM
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3D Structure of Enzyme-Ligand-Complex (PDB) (4 results)

Enzyme Kinetic Parameters

KM Value (50 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.077
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Ki Value (8 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.973
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pH 5.5, 24°C

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE

References & Links

Links to other databases for 4-Methylumbelliferone

ChEBI
PubChem
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PubChem