(1S)-3-[(2Z)-but-2-en-1-yl]-2-methyl-4-oxocyclopent-2-en-1-yl (1R,3R)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate

• ChemBase ID: 164770
• Molecular Formular: C20H28O3
• Molecular Mass: 316.43452
• Monoisotopic Mass: 316.20384476
• 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
• 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)C
• InChI: InChI=1S/C20H28O3/c1-7-8-9-14-13(4)17(11-16(14)21)23-19(22)18-15(10-12(2)3)20(18,5)6/h7-8,10,15,17-18H,9,11H2,1-6H3/b8-7-/t15-,17+,18+/m1/s1
• InChIKey: FMTFEIJHMMQUJI-DFKXKMKHSA-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)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
• IUPAC Traditional name: cinerin I
• Synonyms: (1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propenyl)cyclopropanecarboxylic Acid (1S)-3-(2Z)-2-Butenyl-2-methyl-4-oxo-2-cyclopenten-1-yl Ester; Cinerin; Cinerin I

Database IDs

• CAS Number: 25402-06-6
• PubChem SID: 162258905
• PubChem CID: 5281547

CALCULATED PROPERTIES

• Acid pKa: 18.088158
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.4428253
• LogD (pH = 7.4): 4.4428253
• Log P: 4.4428253
• Molar Refractivity: 94.3835 cm^3
• Polarizability: 36.222446 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C441980

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)