(4S)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoic acid

• ChemBase ID: 179490
• Molecular Formular: C16H21NO4
• Molecular Mass: 291.34224
• Monoisotopic Mass: 291.14705816
• SMILES: c1(c(cc(cc1)[C@](CCC(=O)O)(C(C)C)C#N)OC)OC
• Canonical SMILES: N#C[C@](c1ccc(c(c1)OC)OC)(C(C)C)CCC(=O)O
• InChI: InChI=1S/C16H21NO4/c1-11(2)16(10-17,8-7-15(18)19)12-5-6-13(20-3)14(9-12)21-4/h5-6,9,11H,7-8H2,1-4H3,(H,18,19)/t16-/m0/s1
• InChIKey: BSHCLIANLKRGLY-INIZCTEOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoic acid
• IUPAC Traditional name: (4S)-4-cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoic acid
• Synonyms: (R)-4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoic Acid; (R)-γ-Cyano-3,4-dimethoxy-γ-(1-methylethyl)-benzenebutanoic Acid; (R)-(+)-Verapamilic Acid; (S)-4-Cyano-4-(3,4-dimethoxyphenyl)-5-methylhexanoic Acid; (S)-γ-Cyano-3,4-dimethoxy-γ-(1-methylethyl)-benzenebutanoic Acid; l-γ-Cyano-γ-(3,4-dimethoxyphenyl)-γ-isopropylbutyric Acid; (S)-(-)-Verapamilic Acid

Database IDs

• CAS Number: 36622-24-9; 38175-99-4
• PubChem SID: 164235400
• PubChem CID: 11130069

CALCULATED PROPERTIES

• Acid pKa: 2.54704
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): -0.09821725
• LogD (pH = 7.4): -0.75624377
• Log P: 2.7530844
• Molar Refractivity: 78.3638 cm^3
• Polarizability: 30.468184 Å^3
• Polar Surface Area: 79.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate; Methanol
• Apperance: Clear Colorless Semi Solid; White Solid

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - V126300

Precursor for Verapamil. Calcium antagonist.

Toronto Research Chemicals - V126305

Precursor for Verapamil.Calcium antagonist.

REFERENCES

• Atlas, D, and Adler, M.: Proc. Natl. Acad. Sci. USA, 78, 1237 (1981)
• Janis, R., et al.: Adv. Drug. Res., 16, 309 (1987)
• Atlas, D, and Adler, M.: Proc. Natl. Acad. Sci. USA, 78, 1237 (1981)
• Janis, R., et al.: Adv. Drug. Res., 16, 309 (1987)