(1S)-2-methyl-4-oxo-3-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl (1R,3R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate

• ChemBase ID: 172009
• Molecular Formular: C22H30O5
• Molecular Mass: 374.4706
• Monoisotopic Mass: 374.20932406
• SMILES: [C@H]1(C(=C(C(=O)C1)C/C=C\CC)C)OC(=O)[C@@H]1[C@H](C1(C)C)/C=C(\C)/C(=O)OC
• Canonical SMILES: CC/C=C\CC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@H](C1(C)C)/C=C(/C(=O)OC)\C
• InChI: InChI=1S/C22H30O5/c1-7-8-9-10-15-14(3)18(12-17(15)23)27-21(25)19-16(22(19,4)5)11-13(2)20(24)26-6/h8-9,11,16,18-19H,7,10,12H2,1-6H3/b9-8-,13-11+/t16-,18+,19+/m1/s1
• InChIKey: WKNSDDMJXANVMK-XIGJTORUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-2-methyl-4-oxo-3-[(2Z)-pent-2-en-1-yl]cyclopent-2-en-1-yl (1R,3R)-3-[(1E)-3-methoxy-2-methyl-3-oxoprop-1-en-1-yl]-2,2-dimethylcyclopropane-1-carboxylate
• IUPAC Traditional name: jasmolin II
• Synonyms: (1R,3R)-3-[(1E)-3-Methoxy-2-methyl-3-oxo-1-propen-1-yl]-2,2-dimethylcyclopropanecarboxylic Acid (1S)-2-Methyl-4-oxo-3-(2Z)-2-penten-1-yl-2-cyclopenten-1-yl Ester; Jasmolin II

Database IDs

• CAS Number: 1172-63-0
• PubChem SID: 164227919
• PubChem CID: 12304690

CALCULATED PROPERTIES

• Acid pKa: 18.08816
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.458314
• LogD (pH = 7.4): 4.458314
• Log P: 4.458314
• Molar Refractivity: 105.4708 cm^3
• Polarizability: 40.674923 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - J210505

An active insecticidal constituent of pyrethrum flowers.

REFERENCES

• Okey, A., et al.: Pharmacol. Ther., 45, 241 (1990)
• Barter, R., et al.: Toxicol. Appl. Pharmacol., 113, 36 (1990)
• Hood, A., et al.: Toxicol. Sci., 49, 263 (1990)