CHEBI:65794 - dilopholide

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ChEBI Name dilopholide
ChEBI ID CHEBI:65794
Definition A diterpenoid isolated from the brown alga Dilophus ligulatus and has been shown to exhibit cytotoxic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C22H32O4
Net Charge 0
Average Mass 360.48710
Monoisotopic Mass 360.23006
InChI InChI=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
InChIKey DFKHRBLZEJCJLU-ZBXWVNBDSA-N
SMILES [H][C@@]12C\C(C)=C\CC\C(=C\OC(C)=O)[C@@]([H])(C(=O)O1)[C@@]2([H])[C@@H](C)CCC=C(C)C
Metabolite of Species Details
Dilophus ligulatus (WORMS:381221) 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 dilopholide (CHEBI:65794) has role antineoplastic agent (CHEBI:35610)
dilopholide (CHEBI:65794) has role metabolite (CHEBI:25212)
dilopholide (CHEBI:65794) is a γ-lactone (CHEBI:37581)
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)
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 Number Type Source
15775451 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
8277314 PubMed citation Europe PMC
Last Modified
01 August 2013