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CHEBI:66542 - lancifodilactone F

ChEBI IDCHEBI:66542
ChEBI Namelancifodilactone F
Stars
DefinitionA tetracyclic triterpenoid that is a rearranged pentanortriterpenoid derived from cycloartane. Isolated from the leaves and stem of Schisandra lancifolia, it exhibits anti-HIV activity.
Last Modified19 March 2013
DownloadsMolfile
FormulaC25H40O6
Net Charge0
Average Mass436.589
Monoisotopic Mass436.28249
SMILES[H][C@]12CC[C@@]3(C)[C@@](C)(CC[C@]3([H])[C@H](C)C(=O)O)[C@@]1([H])CC[C@@]([H])([C@](C)(O)CO)[C@@]1(CCC(=O)O1)C2
InChIInChI=1S/C25H40O6/c1-15(21(28)29)17-8-11-23(3)18-5-6-19(24(4,30)14-26)25(12-9-20(27)31-25)13-16(18)7-10-22(17,23)2/h15-19,26,30H,5-14H2,1-4H3,(H,28,29)/t15-,16+,17+,18-,19-,22+,23-,24+,25+/m0/s1
InChIKeyGFRDTMTUJTYIJJ-IUSUREMMSA-N
Species of MetaboliteComponentSourceComments
Schisandra lancifolia (ncbitaxon:238549)
leaf (BTO:0000713) PubMed (15787482)
stem (BTO:0001300) PubMed (15787482)
Roles Classification
Chemical Role:
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
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)
lancifodilactone F (CHEBI:66542) has role anti-HIV agent (CHEBI:64946)
lancifodilactone F (CHEBI:66542) has role metabolite (CHEBI:25212)
lancifodilactone F (CHEBI:66542) is a diol (CHEBI:23824)
lancifodilactone F (CHEBI:66542) is a monocarboxylic acid (CHEBI:25384)
lancifodilactone F (CHEBI:66542) is a oxaspiro compound (CHEBI:37948)
lancifodilactone F (CHEBI:66542) is a tetracyclic triterpenoid (CHEBI:26893)
lancifodilactone F (CHEBI:66542) is a γ-lactone (CHEBI:37581)
IUPAC Name 
(2S)-2-{(3R,3aR,5aR,7R,8S,10aS,10bS)-8-[(2S)-1,2-dihydroxypropan-2-yl]-3a,10b-dimethyl-5'-oxotetradecahydro-1H,3'H-spiro[cyclohepta[e]indene-7,2'-furan]-3-yl}propanoic acid
Registry NumbersSources
Reaxys:10049664Reaxys
Citations