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

• ChemBase ID: 133564
• Molecular Formular: C15H20O3
• Molecular Mass: 248.3175
• Monoisotopic Mass: 248.1412445
• SMILES: CC1=CCC[C@@]2([C@H](O2)[C@@H]2[C@@H](CC1)C(=C)C(=O)O2)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-ZRPLFPEYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,4R,7Z,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^2,^4]tetradec-7-en-13-one
• IUPAC Traditional name: (1S,2R,4R,7Z,11S)-4,8-dimethyl-12-methylidene-3,14-dioxatricyclo[9.3.0.0^2,^4]tetradec-7-en-13-one
• Synonyms: Parthenolide

Database IDs

• CAS Number: 20554-84-1
• MDL Number: MFCD00134592
• PubChem SID: 24278621; 162227841
• PubChem CID: 5420804

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

• Melting Point: 115-116 °C(lit.)

Safety Information

• RTECS: LY4220000
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ELA2(1991), IKBKG(8517), NFKB1(4790), NKAP(79576), NKRF(55922)

Product Information

• Purity: ≥98% (HPLC)
• Classification: Rare Genuine Natural Compounds

DETAILS

Sigma Aldrich - P0667

Biochem/physiol Actions
Anti-inflammatory agent that inhibits NF-κB activation.
Other Notes
Sesquiterpene lactone found in feverfew (Tanacetum parthenium) and other plants.