Structure via PubChem · Public domain (PubChem)
parthenolide
Sign in to saveParthenolide 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.
Chemical data
- Formula
- C15H20O3
- Molecular weight
- 248.32 g/mol
- IUPAC name
- (1S,2S,4R,7Z,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one
- SMILES
- C/C/1=C/CC[C@@]2([C@@H](O2)[C@@H]3[C@@H](CC1)C(=C)C(=O)O3)C
- InChIKey
- KTEXNACQROZXEV-QLIGOWBFSA-N
- XLogP
- 2.3
- Polar surface area
- 38.8 Ų
- H-bond donors
- 0
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,192 papers- Parthenolide ameliorates colon inflammation through regulating Treg/Th17 balance in a gut microbiota-dependent manner.Theranostics · 2020
- Parthenolide attenuates hypoxia-induced pulmonary hypertension through inhibiting STAT3 signaling.Phytomedicine : international journal of phytotherapy and phytopharmacology · 2024
- Pivotal role of JNK protein in the therapeutic efficacy of parthenolide against breast cancer: Novel and comprehensive evidences from network pharmacology, single-cell RNA sequencing and metabolomics.International journal of biological macromolecules · 2024
- Advances in chemistry and bioactivity of parthenolide.Natural product reports · 2020
- Parthenolide ameliorates neurological deficits and neuroinflammation in mice with traumatic brain injury by suppressing STAT3/NF-κB and inflammasome activation.International immunopharmacology · 2022
via PubMed
Wikidata facts
- Mass
- 248.141245
Show 6 more facts
- found in taxon
- Asteraceae
- subject has role
- non-steroidal anti-inflammatory drug
- 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
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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.