(1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.02,4]tetradec-7-en-13-one

• ChemBase ID: 179839
• Molecular Formular: C15H20O3
• Molecular Mass: 248.3175
• Monoisotopic Mass: 248.1412445
• SMILES: [C@H]12O[C@@]1(CCC=C(CC[C@@H]1[C@@H]2OC(=O)C1=C)C)C
• Canonical SMILES: CC1=CCC[C@@]2(C)O[C@@H]2[C@@H]2[C@@H](CC1)C(=C)C(=O)O2
• InChI: InChI=1S/C15H20O3/c1-9-5-4-8-15(3)13(18-15)12-11(7-6-9)10(2)14(16)17-12/h5,11-13H,2,4,6-8H2,1,3H3/b9-5+/t11-,12-,13-,15+/m0/s1
• InChIKey: KTEXNACQROZXEV-SLXBATTESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^2,^4]tetradec-7-en-13-one
• IUPAC Traditional name: (-)-parthenolide; (1S,2S,4R,7E,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^2,^4]tetradec-7-en-13-one
• Synonyms: 4,5-Epoxy-1(10),11(13)-germacradien-12,6-olide; Parthenolide

Database IDs

• CAS Number: 20554-84-1
• PubChem SID: 164235749
• PubChem CID: 6473881

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 3.0712926
• LogD (pH = 7.4): 3.0712926
• Log P: 3.0712926
• Molar Refractivity: 68.5529 cm^3
• Polarizability: 27.145802 Å^3
• Polar Surface Area: 38.83 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: Powder

Pharmacology Properties

• Mechanism of Action: 5-HT antagonist; Interleukin antagonist; Interleukin-1 antagonist; Nitric oxide antagonist; Prostaglandin antagonist; Prostaglandin-E2 antagonist; TNF-alpha antagonist

Product Information

• Purity: 98.5
• Biological Source: Constit. of Chrysanthemum parthenium (feverfew) and Michelia champaca
• Application(s): Active ingredient in folk remedies used to treat migraine; Antineoplastic agent; Inhibits smooth muscle contractility

REFERENCES

• Govindachari, T.R. et al., Tetrahedron, 1965, 21, 1509, (isol, struct)
• Quick, A. et al., J.C.S. Perkin 2, 1976, 465, (cryst struct)
• Ogura, M. et al., Phytochemistry, 1978, 17, 957, (isol)
• Heptinstall, S. et al., J. Pharm. Pharmacol., 1992, 44, 391, (anal)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1370
• Hay, A.J.B. et al., Br. J. Pharmacol., 1994, 112, 9, (pharmacol)
• Jacobsson, U. et al., Phytochemistry, 1995, 39, 839, (Parthenolide, pmr, cmr)
• Hendriks, H. et al., Planta Med., 1997, 63, 356-359, (Parthenolide, isol)
• Fischer, N.H. et al., Phytochemistry, 1998, 49, 559-564, (activity)