Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB120431
Identification
Name: 4-methylumbelliferone
Description:A hydroxycoumarin that is umbelliferone substituted by a methyl group at position 4.
Structure
Thumb
Synonyms:
  • 4-Methyl-7-hydroxycoumarin
  • 4-Methylumbelliferone
  • 4-methylumbelliferone
  • 4-MU
  • 7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyran
  • 7-Hydroxy-4-methyl-2-oxo-3-chromene
  • 7-Hydroxy-4-methyl-2H-1-benzopyran-2-one
  • 7-Hydroxy-4-methylcoumarin
  • beta-Methylumbelliferone
  • Hymecromone
  • Imecromone
Chemical Formula: C10H8O3
Average Molecular Weight: 176.171
Monoisotopic Molecular Weight: 176.04735
InChI Key: HSHNITRMYYLLCV-UHFFFAOYSA-N
InChI:InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
CAS number: Not Available
IUPAC Name:7-hydroxy-4-methyl-2H-chromen-2-one
Traditional IUPAC Name: 4-methylumbelliferone
SMILES:CC1(=CC(OC2(C=C(O)C=CC1=2))=O)
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
Kingdom Chemical entities
Super ClassOrganic compounds
Class Phenylpropanoids and polyketides
Sub ClassCoumarins and derivatives
Direct Parent 7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
    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
    References
    References:
    • Nakamura T, Ishikawa T, Nanashima N, Miura T, Nozaka H, Nakaoka R, Sato T (2002)4-Methylumbelliferone induces the expression of membrane type 1-matrix metalloproteinase in cultured human skin fibroblasts. Biochemical and biophysical research communications 298, Pubmed: 12419303
    • Varga JM, Kalchschmid G, Klein GF, Fritsch P (1991)Mechanism of allergic cross-reactions--I. Multispecific binding of ligands to a mouse monoclonal anti-DNP IgE antibody. Molecular immunology 28, Pubmed: 1650428
    • Lokeshwar VB, Lopez LE, Munoz D, Chi A, Shirodkar SP, Lokeshwar SD, Escudero DO, Dhir N, Altman N (2010)Antitumor activity of hyaluronic acid synthesis inhibitor 4-methylumbelliferone in prostate cancer cells. Cancer research 70, Pubmed: 20332231
    • Nakamura R, Kuwabara H, Yoneda M, Yoshihara S, Ishikawa T, Miura T, Nozaka H, Nanashima N, Sato T, Nakamura T (2007)Suppression of matrix metalloproteinase-9 by 4-methylumbelliferone. Cell biology international 31, Pubmed: 17470403
    • Saito T, Tamura D, Nakamura T, Makita Y, Ariyama H, Komiyama K, Yoshihara T, Asano R (2013)4-methylumbelliferone leads to growth arrest and apoptosis in canine mammary tumor cells. Oncology reports 29, Pubmed: 23124556
    • Fang Y, Wang H, Zhu W, Wang L, Liu H, He Y, Xu X, Yin W, Sima Y, Xu S (2014)Antioxidative capacity in the fat body of Bombyx mori is increased following oral administration of 4-methylumbelliferone. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 159, Pubmed: 24080584
    • Qin J, Kilkus J, Dawson G (2016)The hyaluronic acid inhibitor 4-methylumbelliferone is an NSMase2 activator-role of Ceramide in MU anti-tumor activity. Biochimica et biophysica acta 1861, Pubmed: 26548718
    • Benitez A, Yates TJ, Shamaldevi N, Bowen T, Lokeshwar VB (2013)Dietary supplement hymecromone and sorafenib: a novel combination for the control of renal cell carcinoma. The Journal of urology 190, Pubmed: 23228386
    Synthesis Reference: Not Available
    Material Safety Data Sheet (MSDS) Not Available
    External Links:
    ResourceLink
    METABOLIGHTSMTBLC17224
    HMDBHMDB59622
    CHEMSPIDER4444190
    PUBCHEM5280567
    CHEBI17224
    LIGAND-CPDC03081
    CAS90-33-5