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

• ChemBase ID: 172008
• Molecular Formular: C21H30O3
• Molecular Mass: 330.4611
• Monoisotopic Mass: 330.21949482
• 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
• 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)C
• InChI: InChI=1S/C21H30O3/c1-7-8-9-10-15-14(4)18(12-17(15)22)24-20(23)19-16(11-13(2)3)21(19,5)6/h8-9,11,16,18-19H,7,10,12H2,1-6H3/b9-8-/t16-,18+,19+/m1/s1
• InChIKey: NZKIRHFOLVYKFT-VUMXUWRFSA-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)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carboxylate
• IUPAC Traditional name: jasmolin I
• Synonyms: (1R,3R)-2,2-Dimethyl-3-(2-methyl-1-propen-1-yl)cyclopropanecarboxylic Acid (1S)-2-Methyl-4-oxo-3-(2Z)-2-penten-1-yl-2-cyclopenten-1-yl Ester; Jasmolin I

Database IDs

• CAS Number: 4466-14-2
• PubChem SID: 164227918
• PubChem CID: 12304687

CALCULATED PROPERTIES

• Acid pKa: 18.08816
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 4.887394
• LogD (pH = 7.4): 4.887394
• Log P: 4.887394
• Molar Refractivity: 98.9845 cm^3
• Polarizability: 38.06592 Å^3
• Polar Surface Area: 43.37 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - J210500

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)