melophlin R (CHEBI:66693)

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ChEBI Name	melophlin R

ChEBI ID	CHEBI:66693

Definition	A member of the class of pyrrolidin-2-ones that is 1,5-dimethylpyrrolidine-2,4-dione substituted by a 1-hydroxy-12-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

Average Mass

351.52340

Monoisotopic Mass

351.27734

InChI

InChI=1S/C21H37NO3/c1-5-16(2)14-12-10-8-6-7-9-11-13-15-18(23)19-20(24)17(3)22(4)21(19)25/h16-17,23H,5-15H2,1-4H3/b19-18-

InChIKey

QDDWPSIPKTZOEU-HNENSFHCSA-N

SMILES

CCC(C)CCCCCCCCCC\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.

ChEBI Ontology
Outgoing	melophlin R (CHEBI:66693) has role antineoplastic agent (CHEBI:35610) melophlin R (CHEBI:66693) has role metabolite (CHEBI:25212) melophlin R (CHEBI:66693) is a enol (CHEBI:33823) melophlin R (CHEBI:66693) is a pyrrolidin-2-ones (CHEBI:74223)

IUPAC Name

(3Z)-3-(1-hydroxy-12-methyltetradecylidene)-1,5-dimethylpyrrolidine-2,4-dione

Registry Number	Type	Source
10382681	Reaxys Registry Number	Reaxys

Citation	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 5R and 5S enantiomers.