EMBL-EBI | Chemical Biology | ChEBI

Example searches: iron*, InChI=1S/CH4O/c1-2/h2H,1H3, caffeine | Advanced Search

CHEBI:66508 - sinularolide C

ChEBI IDCHEBI:66508
ChEBI Namesinularolide C
Stars
DefinitionA cembrane diterpenoid that is an epimer of sinularolide B at C-3. Isolated from Sinularia gibberosa and has been found to exhibit antineoplastic activity.
Last Modified8 July 2013
DownloadsMolfile
FormulaC20H28O5
Net Charge0
Average Mass348.439
Monoisotopic Mass348.19367
SMILES[H][C@@]12OC(=O)C(=C)[C@@]1([H])C[C@]1([H])O[C@]1(CO)CC/C=C(\C)CC/C=C(\C)[C@@H]2O
InChIInChI=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
InChIKeyMULWDJOXRRXULO-HAUURUDMSA-N
Species of MetaboliteComponentSourceComments
Sinularia gibberosa (WORMS:288527) - PubMed (15921403)
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)
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 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)
sinularolide C (CHEBI:66508) is a γ-lactone (CHEBI:37581)
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 NumbersSources
Reaxys:10725395Reaxys
Citations