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parthenolide

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Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named, and in the closely related tansy (Tanacetum vulgare). It is found in highest concentration in the flowers and fruit. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available.

Wikidata facts

Mass
248.141245
Show 6 more facts
found in taxon
Asteraceae
chemical formula
C₁₅H₂₀O₃
canonical SMILES
CC1=CCCC2(C(O2)C3C(CC1)C(=C)C(=O)O3)C
isomeric SMILES
C=C1C(=O)O[C@H]2[C@H]1CC/C(C)=C\CC[C@@]1(C)O[C@@H]21
Commons category
Parthenolide
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Encyclopedic overview

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Parthenolide is a sesquiterpene lactone of the germacranolide class which occurs naturally in the plant feverfew (Tanacetum parthenium), after which it is named, and in the closely related tansy (Tanacetum vulgare). It is found in highest concentration in the flowers and fruit. Parthenolide's molecular structure depiction is often incorrect regarding the stereochemistry of the epoxide, although X-ray single crystal structures are available.

Lack of solubility in water and bioavailability limits the potential of parthenolide as a drug.

Excerpted from Wikipedia’s “parthenolide” article, available under the CC BY-SA 4.0 licence.