(R)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate

• ChemBase ID: 165728
• Molecular Formular: C22H19Br2NO3
• Molecular Mass: 505.19916
• Monoisotopic Mass: 502.97316747
• SMILES: c1c(cccc1)Oc1cccc(c1)[C@@H](OC(=O)[C@H]1C([C@H]1C=C(Br)Br)(C)C)C#N
• Canonical SMILES: N#C[C@@H](c1cccc(c1)Oc1ccccc1)OC(=O)[C@@H]1[C@@H](C1(C)C)C=C(Br)Br
• InChI: InChI=1S/C22H19Br2NO3/c1-22(2)17(12-19(23)24)20(22)21(26)28-18(13-25)14-7-6-10-16(11-14)27-15-8-4-3-5-9-15/h3-12,17-18,20H,1-2H3/t17-,18-,20-/m0/s1
• InChIKey: OWZREIFADZCYQD-BJLQDIEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (R)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• IUPAC Traditional name: (R)-cyano(3-phenoxyphenyl)methyl (1R,3R)-3-(2,2-dibromoethenyl)-2,2-dimethylcyclopropane-1-carboxylate
• Synonyms: (1R,3R)-3-(2,2-Dibromoethenyl)-2,2-dimethylcyclopropanecarboxylic Acid (S)-cyano(3-phenoxyphenyl)methyl Ester; Decamethrin; Esbecythrin; FMC-45498; NRDC-161; Deltamethrin

Database IDs

• CAS Number: 52918-63-5
• PubChem SID: 162259861
• PubChem CID: 6453235

CALCULATED PROPERTIES

• Acid pKa: 10.619197
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 5.74409
• LogD (pH = 7.4): 5.7438316
• Log P: 5.7440934
• Molar Refractivity: 124.2894 cm^3
• Polarizability: 44.165997 Å^3
• Polar Surface Area: 59.32 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dioxane; Ethanol
• Apperance: White Solid
• Melting Point: 95-97°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - D230700

Synthetic pyrethroid insecticide, which acts as a potent inhibitor of calcineurin (protein phosphatase 2B) and has an IC50 of about 100pM. This inhibition action results in cellular hyperexcitability by causing non-mutated calcium channels to remain open

REFERENCES

• Kavlock, R., et al.: J. Environ. Pathol. Toxicol., 2, 751 (1979)
• Enan, E., et al.: Biochem. Pharmacol., 43, 1777 (1979)
• Tan, J., et al.: Mol. Biol., 32, 445 (1979)