CHEBI:66542 - lancifodilactone F

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ChEBI Name lancifodilactone F
ChEBI ID CHEBI:66542
Definition A tetracyclic triterpenoid that is a rearranged pentanortriterpenoid derived from cycloartane. Isolated from the leaves and stem of Schisandra lancifolia, it exhibits anti-HIV activity.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C25H40O6
Net Charge 0
Average Mass 436.58150
Monoisotopic Mass 436.28249
InChI InChI=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
InChIKey GFRDTMTUJTYIJJ-IUSUREMMSA-N
SMILES [H][C@]12CC[C@]3(C)[C@]([H])(CC[C@@]3(C)[C@@]1([H])CC[C@@]([H])([C@](C)(O)CO)[C@@]1(CCC(=O)O1)C2)[C@H](C)C(O)=O
Metabolite of Species Details
Schisandra lancifolia (NCBI:txid238549) Found in leaf (BTO:0000713). See: PubMed
Schisandra lancifolia (NCBI:txid238549) Found in stem (BTO:0001300). See: PubMed
Roles Classification
Chemical Role(s): Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 γ-lactone (CHEBI:37581)
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)
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 Number Type Source
10049664 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15787482 PubMed citation Europe PMC
18303901 PubMed citation Europe PMC
22133065 PubMed citation Europe PMC
Last Modified
19 March 2013