(1S)-3-[(2Z)-but-2-en-1-yl]-2-methyl-4-oxocyclopent-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: 164771
• Molecular Formular: C21H28O5
• Molecular Mass: 360.44402
• Monoisotopic Mass: 360.193674
• SMILES: [C@H]1(C(=C(C(=O)C1)C/C=C\C)C)OC(=O)[C@@H]1[C@H](C1(C)C)/C=C(\C)/C(=O)OC
• Canonical SMILES: C/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/C21H28O5/c1-7-8-9-14-13(3)17(11-16(14)22)26-20(24)18-15(21(18,4)5)10-12(2)19(23)25-6/h7-8,10,15,17-18H,9,11H2,1-6H3/b8-7-,12-10+/t15-,17+,18+/m1/s1
• InChIKey: SHCRDCOTRILILT-WOBDGSLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S)-3-[(2Z)-but-2-en-1-yl]-2-methyl-4-oxocyclopent-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: cinerin II
• Synonyms: (1R,3R)-3-[(1E)-3-Methoxy-2-methyl-3-oxo-1-propen-1-yl]-2,2-dimethylcyclopropanecarboxylic Acid (1S)-3-(2Z)-2-Buten-1-yl-2-methyl-4-oxo-2-cyclopenten-1-yl Ester; Cinerin II

Database IDs

• CAS Number: 121-20-0
• PubChem SID: 162258906
• PubChem CID: 5281548

CALCULATED PROPERTIES

• Acid pKa: 18.088158
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 4.0137453
• LogD (pH = 7.4): 4.0137453
• Log P: 4.0137453
• Molar Refractivity: 100.8698 cm^3
• Polarizability: 38.83629 Å^3
• Polar Surface Area: 69.67 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C441985

An active insecticidal constituent of pyrethrum flowers. Oxidizes rapidly and becomes inactive in presence of air.

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)