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CHEBI:69111 - withalongolide F

Default Structure
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:
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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