Elephantopin

Also known as [(1R,3R,5R,6S,10R,11S)-3-methyl-9-methylidene-8,14-dioxo-4,7,15-trioxatetracyclo[11.2.1.03,5.06,10]hexadec-13(16)-en-11-yl] 2-methylprop-2-enoate

Elephantopin is a natural chemical compound extracted from the Elephantopus elatus plant of the genus Elephantopus, family Compositae. It is a sesquiterpene lactone with a germacranolide skeleton, containing two lactone rings and an epoxide functional group.

Chemical data

Formula: C19H20O7
Molecular weight: 360.4 g/mol
IUPAC name: [(1R,3R,5R,6S,10R,11S)-3-methyl-9-methylidene-8,14-dioxo-4,7,15-trioxatetracyclo[11.2.1.03,5.06,10]hexadec-13(16)-en-11-yl] 2-methylprop-2-enoate
SMILES: CC(=C)C(=O)O[C@H]1CC2=C[C@@H](C[C@@]3([C@H](O3)[C@@H]4[C@@H]1C(=C)C(=O)O4)C)OC2=O
InChIKey: WIQOUTANBFOBPB-KIVXNUBRSA-N
XLogP: 0.7
Polar surface area: 91.4 Å²
H-bond donors: 0
H-bond acceptors: 7
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 360.12090298

Show 4 more facts

chemical formula: C₁₉H₂₀O₇
found in taxon: Orthopappus angustifolius
canonical SMILES: O=C(OC1CC2=CC(OC2=O)CC3(OC3C4OC(=O)C(=C)C14)C)C(=C)C
isomeric SMILES: CC(=C)C(=O)O[C@H]1CC2=C[C@@H](C[C@@]3([C@H](O3)[C@@H]4[C@@H]1C(=C)C(=O)O4)C)OC2=O

Sources (3)

via Wikidata · CC0

~1 min read