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

• ChemBase ID: 174662
• Molecular Formular: C26H27ClN2O3S2
• Molecular Mass: 515.08718
• Monoisotopic Mass: 514.11516241
• SMILES: c1(ccc2c(c1)nc(cc2)/C=C/c1cc(ccc1)C(SCCC(=O)N(C)C)SCCC(=O)O)Cl
• Canonical SMILES: OC(=O)CCSC(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+
• InChIKey: AXUZQJFHDNNPFG-UXBLZVDNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-[({3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}({[2-(dimethylcarbamoyl)ethyl]sulfanyl})methyl)sulfanyl]propanoic acid
• IUPAC Traditional name: verlukast, (R-(E))-isomer
• Synonyms: MK-571; 3-[[[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl][[3-(dimethylamino)-3-oxopropyl]thio]methyl]thio]propanoic Acid; L 660711

Database IDs

• CAS Number: 115104-28-4
• PubChem SID: 164230572
• PubChem CID: 5281888

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; Ethyl Acetate
• Apperance: Yellow Solid
• Melting Point: 142-147°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M424500

A receptor antagonist for the treatment of respiratory diseases. Cysteinyl leukotriene receptor antagonist MK-571 alters bronchoalveolar lavage fluid proteome in asthma.

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)