You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version3.6
Creation Date2012-10-30 10:32:48 UTC
Update Date2016-02-11 07:49:33 UTC
HMDB IDHMDB59622
Secondary Accession NumbersNone
Metabolite Identification
Common Name4-Methylumbelliferone
Description4-methylumbelliferone is a substrate for: Liver carboxylesterase 1, Cocaine esterase, and S-formylglutathione hydrolase.
Structure
Thumb
Synonyms
ValueSource
4-Methyl-7-hydroxycoumarinChEBI
7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyranChEBI
7-Hydroxy-4-methyl-2-oxo-3-chromeneChEBI
7-Hydroxy-4-methyl-2H-1-benzopyran-2-oneChEBI
7-Hydroxy-4-methylcoumarinChEBI
beta-MethylumbelliferoneChEBI
HimecromonaChEBI
HymecromoneChEBI
HymecromonumChEBI
ImecromoneChEBI
b-MethylumbelliferoneGenerator
β-methylumbelliferoneGenerator
Chemical FormulaC10H8O3
Average Molecular Weight176.1687
Monoisotopic Molecular Weight176.047344122
IUPAC Name7-hydroxy-4-methyl-2H-chromen-2-one
Traditional Name4-methylumbelliferone
CAS Registry NumberNot Available
SMILES
CC1=CC(=O)OC2=C1C=CC(O)=C2
InChI Identifier
InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
InChI KeyInChIKey=HSHNITRMYYLLCV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • 1-benzopyran
  • Benzopyran
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.99 mg/mLALOGPS
logP2.19ALOGPS
logP1.78ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity47.81 m3·mol-1ChemAxon
Polarizability17.42 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4444190
KEGG Compound IDC03081
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB59622
Metagene LinkHMDB59622
METLIN IDNot Available
PubChem Compound5280567
PDB IDNot Available
ChEBI ID17224
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:
CES1
Uniprot ID:
P23141
Molecular weight:
62520.62
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails
General function:
Lipid transport and metabolism
Specific function:
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Shows high catalytic efficiency for hydrolysis of cocaine, 4-methylumbelliferyl acetate, heroin and 6-monoacetylmorphine.
Gene Name:
CES2
Uniprot ID:
O00748
Molecular weight:
68898.39
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails
General function:
Involved in carboxylesterase activity
Specific function:
Serine hydrolase involved in the detoxification of formaldehyde.
Gene Name:
ESD
Uniprot ID:
P10768
Molecular weight:
31462.545
Reactions
4-Methylumbelliferyl acetate + Water → 4-Methylumbelliferone + Acetic aciddetails