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CHEBI:65794 - dilopholide

ChEBI IDCHEBI:65794
ChEBI Namedilopholide
Stars
DefinitionA diterpenoid isolated from the brown alga Dilophus ligulatus and has been shown to exhibit cytotoxic activity.
Last Modified1 August 2013
DownloadsMolfile
FormulaC22H32O4
Net Charge0
Average Mass360.494
Monoisotopic Mass360.23006
SMILES[H][C@]1([C@@H](C)CCC=C(C)C)[C@]2([H])C/C(C)=C/CC/C(=C/OC(C)=O)[C@@]1([H])C(=O)O2
InChIInChI=1S/C22H32O4/c1-14(2)8-6-10-16(4)20-19-12-15(3)9-7-11-18(13-25-17(5)23)21(20)22(24)26-19/h8-9,13,16,19-21H,6-7,10-12H2,1-5H3/b15-9+,18-13-/t16-,19-,20-,21+/m0/s1
InChIKeyDFKHRBLZEJCJLU-ZBXWVNBDSA-N
Species of MetaboliteComponentSourceComments
Dilophus ligulatus (WORMS:381221) - PubMed (8277314)
Roles Classification
Biological Role:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Application:
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
dilopholide (CHEBI:65794) has role antineoplastic agent (CHEBI:35610)
dilopholide (CHEBI:65794) has role metabolite (CHEBI:25212)
dilopholide (CHEBI:65794) is a acetate ester (CHEBI:47622)
dilopholide (CHEBI:65794) is a bridged compound (CHEBI:35990)
dilopholide (CHEBI:65794) is a diterpenoid (CHEBI:23849)
dilopholide (CHEBI:65794) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(Z)-{(1S*,5E,8S*,11R*)-6-methyl-11-[(2S*)-6-methylhept-5-en-2-yl]-10-oxo-9-oxabicyclo[6.2.1]undec-5-en-2-ylidene}methyl acetate
Registry NumbersSources
Reaxys:15775451Reaxys
Citations