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CHEBI:69111 - withalongolide F

ChEBI IDCHEBI:69111
ChEBI Namewithalongolide F
Stars
DefinitionA steroid lactone that is a 4-norwithanolide with a 2,5-dien-1-one system isolated from the aerial parts of Physalis longifolia.
Last Modified20 November 2013
DownloadsMolfile
FormulaC27H36O4
Net Charge0
Average Mass424.581
Monoisotopic Mass424.26136
SMILES[H][C@@]12CC=C3C=CC(=O)[C@]3(C)[C@@]1([H])CC[C@@]1(C)[C@@]2([H])CC[C@]1([H])[C@H](C)[C@@]1([H])CC(C)=C(CO)C(=O)O1
InChIInChI=1S/C27H36O4/c1-15-13-23(31-25(30)19(15)14-28)16(2)20-8-9-21-18-7-5-17-6-10-24(29)27(17,4)22(18)11-12-26(20,21)3/h5-6,10,16,18,20-23,28H,7-9,11-14H2,1-4H3/t16-,18-,20+,21-,22-,23+,26+,27-/m0/s1
InChIKeyIBYXDWNHLOGYIN-OSVRZWSTSA-N
Species of MetaboliteComponentSourceComments
Physalis longifolia (ncbitaxon:161495) aerial part (BTO:0001658) PubMed (22098611) CH2Cl2-MeOH(1:1) extract of the air-dried aerial parts
Roles Classification
Biological Roles:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
ChEBI Ontology
Outgoing Relation(s)
withalongolide F (CHEBI:69111) has role metabolite (CHEBI:25212)
withalongolide F (CHEBI:69111) has role plant metabolite (CHEBI:76924)
withalongolide F (CHEBI:69111) is a steroid lactone (CHEBI:26766)
withalongolide F (CHEBI:69111) is a δ-lactone (CHEBI:18946)
IUPAC Name 
(6R)-6-{(1S)-1-[(1R,3aS,3bS,8aR,8bS,10aS)-8a,10a-dimethyl-8-oxo-1,2,3,3a,3b,4,8,8a,8b,9,10,10a-dodecahydrodicyclopenta[a,f]naphthalen-1-yl]ethyl}-3-(hydroxymethyl)-4-methyl-5,6-dihydro-2H-pyran-2-one
Synonym  Source
nor-27-hydroxy-1-oxowitha-2,5,24-trienolideChEBI
Registry NumbersSources
Reaxys:22217706Reaxys
Citations