CHEBI:66692 - melophlin Q

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ChEBI Name melophlin Q
ChEBI ID CHEBI:66692
Definition A pyrrolidinone that is 1,5-dimethylpyrrolidine-2,4-dione substituted by a 1-hydroxy-13-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
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Formula C21H37NO3
Net Charge 0
Average Mass 351.52340
Monoisotopic Mass 351.27734
InChI InChI=1S/C21H37NO3/c1-16(2)14-12-10-8-6-5-7-9-11-13-15-18(23)19-20(24)17(3)22(4)21(19)25/h16-17,23H,5-15H2,1-4H3/b19-18-
InChIKey DOKONNWENRHBTP-HNENSFHCSA-N
SMILES CC(C)CCCCCCCCCCC\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 Q (CHEBI:66692) has role antineoplastic agent (CHEBI:35610)
melophlin Q (CHEBI:66692) has role metabolite (CHEBI:25212)
melophlin Q (CHEBI:66692) is a enol (CHEBI:33823)
melophlin Q (CHEBI:66692) is a lactam (CHEBI:24995)
melophlin Q (CHEBI:66692) is a pyrrolidin-2-ones (CHEBI:74223)
IUPAC Name
(3Z)-3-(1-hydroxy-13-methyltetradecylidene)-1,5-dimethylpyrrolidine-2,4-dione
Manual Xref Database
24693565 ChemSpider
View more database links
Registry Number Type Source
10382724 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
16755057 PubMed citation Europe PMC
19035571 PubMed citation Europe PMC
Last Modified
20 June 2013
General Comment
2013-04-05 The compound has been isolated as a mixture of 5R and 5S enantiomers.