CHEBI:66508 - sinularolide C

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ChEBI Name sinularolide C
ChEBI ID CHEBI:66508
Definition A cembrane diterpenoid that is an epimer of sinularolide B at C-3. Isolated from Sinularia gibberosa and has been found to exhibit antineoplastic activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C20H28O5
Net Charge 0
Average Mass 348.43330
Monoisotopic Mass 348.19367
InChI InChI=1S/C20H28O5/c1-12-6-4-8-13(2)17(22)18-15(14(3)19(23)24-18)10-16-20(11-21,25-16)9-5-7-12/h7-8,15-18,21-22H,3-6,9-11H2,1-2H3/b12-7+,13-8+/t15-,16+,17+,18-,20+/m1/s1
InChIKey MULWDJOXRRXULO-HAUURUDMSA-N
SMILES [H][C@]12C[C@]3([H])C(=C)C(=O)O[C@@]3([H])[C@@H](O)\C(C)=C\CC\C(C)=C\CC[C@@]1(CO)O2
Metabolite of Species Details
Sinularia gibberosa (WORMS:288527) 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 sinularolide C (CHEBI:66508) has role antineoplastic agent (CHEBI:35610)
sinularolide C (CHEBI:66508) has role metabolite (CHEBI:25212)
sinularolide C (CHEBI:66508) is a γ-lactone (CHEBI:37581)
sinularolide C (CHEBI:66508) is a cembrane diterpenoid (CHEBI:60687)
sinularolide C (CHEBI:66508) is a epoxide (CHEBI:32955)
sinularolide C (CHEBI:66508) is a macrocycle (CHEBI:51026)
sinularolide C (CHEBI:66508) is a primary alcohol (CHEBI:15734)
sinularolide C (CHEBI:66508) is a secondary alcohol (CHEBI:35681)
IUPAC Name
(1aS,4E,8E,10S,10aR,13aR,14aS)-10-hydroxy-1a-(hydroxymethyl)-5,9-dimethyl-13-methylidene-2,3,6,7,10,10a,13,13a,14,14a-decahydrooxireno[4,5]cyclotetradeca[1,2-b]furan-12(1aH)-one
Registry Number Type Source
10725395 Reaxys Registry Number Reaxys
Citation Waiting for Citations Type Source
15921403 PubMed citation Europe PMC
Last Modified
08 July 2013