CHEBI:17224 - 4-methylumbelliferone

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ChEBI Name 4-methylumbelliferone
ChEBI ID CHEBI:17224
Definition A hydroxycoumarin that is umbelliferone substituted by a methyl group at position 4.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:1903, CHEBI:20452, CHEBI:110550, CHEBI:12030
Supplier Information ChemicalBook:CB5745737, eMolecules:36378197, eMolecules:529222, Selleckchem:4-Methylumbelliferone(4-MU), ZINC000000058121
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Hymecromone (4-methylumbelliferone) is a drug used in bile therapy. It is used as choleretic and antispasmodic drugs and as a standard for the fluorometric determination of enzyme activity. Hymecromone is a crystalline solid with a melting point of 194–195 °C. It is soluble in methanol and glacial acetic acid.
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Formulae C10H8O3
C10H8O3
Net Charge 0
Average Mass 176.169
Monoisotopic Mass 176.04734
InChI InChI=1S/C10H8O3/c1-6-4-10(12)13-9-5-7(11)2-3-8(6)9/h2-5,11H,1H3
InChIKey HSHNITRMYYLLCV-UHFFFAOYSA-N
SMILES C1=2OC(=O)C=C(C1=CC=C(C2)O)C
Roles Classification
Biological Role(s): hyaluronic acid synthesis inhibitor
Any compound that inhibits one or more steps in the pathway leading to the synthesis of hyaluronic acid.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
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ChEBI Ontology
Outgoing 4-methylumbelliferone (CHEBI:17224) has functional parent umbelliferone (CHEBI:27510)
4-methylumbelliferone (CHEBI:17224) has role antineoplastic agent (CHEBI:35610)
4-methylumbelliferone (CHEBI:17224) has role hyaluronic acid synthesis inhibitor (CHEBI:131561)
4-methylumbelliferone (CHEBI:17224) is a hydroxycoumarin (CHEBI:37912)
Incoming 4-methylumbelliferone β-D-glucuronide (CHEBI:1904) has functional parent 4-methylumbelliferone (CHEBI:17224)
4-methylumbelliferone sulfate (CHEBI:1905) has functional parent 4-methylumbelliferone (CHEBI:17224)
4-methylumbelliferyl α-D-galactoside (CHEBI:91115) has functional parent 4-methylumbelliferone (CHEBI:17224)
4-methylumbelliferyl α-L-arabinoside (CHEBI:90130) has functional parent 4-methylumbelliferone (CHEBI:17224)
4-methylumbelliferyl β-D-galactoside (CHEBI:91116) has functional parent 4-methylumbelliferone (CHEBI:17224)
4-methylumbelliferyl β-D-glucoside (CHEBI:91117) has functional parent 4-methylumbelliferone (CHEBI:17224)
4-methylumbelliferyl butyate (CHEBI:91120) has functional parent 4-methylumbelliferone (CHEBI:17224)
chlorferron (CHEBI:38620) has functional parent 4-methylumbelliferone (CHEBI:17224)
IUPAC Name
7-hydroxy-4-methyl-2H-chromen-2-one
INNs Sources
himecromona ChemIDplus
hymecromone KEGG DRUG
hymecromonum ChemIDplus
Synonyms Sources
4-Methyl-7-hydroxycoumarin ChemIDplus
4-Methylumbelliferone KEGG COMPOUND
4-methylumbelliferone UniProt
4-MU ChEBI
7-Hydroxy-4-methyl-2-oxo-2H-1-benzopyran ChemIDplus
7-Hydroxy-4-methyl-2-oxo-3-chromene NIST Chemistry WebBook
7-Hydroxy-4-methyl-2H-1-benzopyran-2-one NIST Chemistry WebBook
7-Hydroxy-4-methylcoumarin ChemIDplus
beta-Methylumbelliferone ChemIDplus
Hymecromone KEGG COMPOUND
Imecromone NIST Chemistry WebBook
Manual Xrefs Databases
1401 DrugCentral
4MU PDBeChem
C03081 KEGG COMPOUND
CPD-182 MetaCyc
D00170 KEGG DRUG
HMDB0059622 HMDB
Hymecromone Wikipedia
LSM-3025 LINCS
View more database links
Registry Numbers Types Sources
142217 Reaxys Registry Number Reaxys
165817 Gmelin Registry Number Gmelin
90-33-5 CAS Registry Number KEGG COMPOUND
90-33-5 CAS Registry Number ChemIDplus
90-33-5 CAS Registry Number NIST Chemistry WebBook
Citations
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, 78-90 [PubMed:26548718]
[show Abstract]
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, 31-37 [PubMed:24080584]
[show Abstract]
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, 335-342 [PubMed:23124556]
[show Abstract]
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, 285-290 [PubMed:23228386]
[show Abstract]
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, 2613-2623 [PubMed:20332231]
[show Abstract]
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, 1022-1026 [PubMed:17470403]
[show Abstract]
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, 646-650 [PubMed:12419303]
[show Abstract]
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, 641-654 [PubMed:1650428]
[show Abstract]
Last Modified
20 August 2019