CHEBI:66694 - melophlin S

Main ChEBI Ontology Automatic Xrefs Reactions Pathways Models
ChEBI Name melophlin S
ChEBI ID CHEBI:66694
Definition A member of the class of pyrrolidin-2-ones that is 1,5-dimethylpyrrolidine-2,4-dione substituted by a 1-hydroxy-5-methyltetradecylidene moiety at position 3. Isolated from the marine sponge Melophlus sarasinorum and other species of genus Melophlus, it exhibits cytotoxicity against murine leukemia cell line.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
more structures >>
Formula C21H37NO3
Net Charge 0
Average Mass 351.52340
Monoisotopic Mass 351.27734
InChI InChI=1S/C21H37NO3/c1-5-6-7-8-9-10-11-13-16(2)14-12-15-18(23)19-20(24)17(3)22(4)21(19)25/h16-17,23H,5-15H2,1-4H3/b19-18-
InChIKey WGGHNDTUKMWTHN-HNENSFHCSA-N
SMILES CCCCCCCCCC(C)CCC\C(O)=C1/C(=O)C(C)N(C)C1=O
Metabolite of Species Details
Melophlus (NCBI:txid283574) See: PubMed
Melophlus sarasinorum (WORMS:169852) See: PubMed
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing melophlin S (CHEBI:66694) has role antineoplastic agent (CHEBI:35610)
melophlin S (CHEBI:66694) has role metabolite (CHEBI:25212)
melophlin S (CHEBI:66694) is a enol (CHEBI:33823)
melophlin S (CHEBI:66694) is a pyrrolidin-2-ones (CHEBI:74223)
IUPAC Name
(3Z)-3-(1-hydroxy-5-methyltetradecylidene)-1,5-dimethylpyrrolidine-2,4-dione
Registry Number Type Source
10383543 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
16755057 PubMed citation Europe PMC
Last Modified
20 June 2013
General Comment
2013-04-08 The compound has been isolated as a mixture of all 4 stereoisomers at C-5 and C-10.