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CHEBI:66542 - lancifodilactone F

Default Structure
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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
anti-HIV agent  An antiviral agent that destroys or inhibits the replication of the human immunodeficiency virus.
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