3-{[(R)-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}({[2-(dimethylcarbamoyl)ethyl]sulfanyl})methyl]sulfanyl}propanoic acid

• ChemBase ID: 179447
• Molecular Formular: C26H27ClN2O3S2
• Molecular Mass: 515.08718
• Monoisotopic Mass: 514.11516241
• SMILES: c1(ccc2c(c1)nc(cc2)/C=C/c1cc(ccc1)[C@H](SCCC(=O)N(C)C)SCCC(=O)O)Cl
• Canonical SMILES: OC(=O)CCS[C@H](c1cccc(c1)/C=C/c1ccc2c(n1)cc(cc2)Cl)SCCC(=O)N(C)C
• InChI: InChI=1S/C26H27ClN2O3S2/c1-29(2)24(30)12-14-33-26(34-15-13-25(31)32)20-5-3-4-18(16-20)6-10-22-11-8-19-7-9-21(27)17-23(19)28-22/h3-11,16-17,26H,12-15H2,1-2H3,(H,31,32)/b10-6+/t26-/m1/s1
• InChIKey: AXUZQJFHDNNPFG-LHAVAQOQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-{[(R)-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}({[2-(dimethylcarbamoyl)ethyl]sulfanyl})methyl]sulfanyl}propanoic acid
• IUPAC Traditional name: verlukast
• Synonyms: 3-[[(R)-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl][[3-(dimethylamino)-3-oxopropyl]thio]methyl]thio]-propanoic Acid; L 668019; MK 679; R-(-)-MK 571; Verlukast

Database IDs

• CAS Number: 120443-16-5
• PubChem SID: 164235357
• PubChem CID: 6509849

CALCULATED PROPERTIES

• Acid pKa: 4.2618084
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.6334977
• LogD (pH = 7.4): 2.9135962
• Log P: 5.6703496
• Molar Refractivity: 142.5198 cm^3
• Polarizability: 56.410862 Å^3
• Polar Surface Area: 70.5 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Dark Yellow Solid
• Melting Point: 57-62°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V128500

A receptor antagonist for the treatment of respiratory diseases.

REFERENCES

• Morgenstern, R., et al.: Biochem. J., 260, 577 (1989)
• Armstrong, R., et al.: Chem. Res. Toxicol., 10, 2 (1989)
• Larsen, J., et al.: Ann. Allergy, 71, 103 (1989)