2-{2-[(3R)-3-({[1-(carboxymethyl)cyclopropyl]methyl}sulfanyl)-3-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}propyl]phenyl}-2-hydroxypropanoic acid

• ChemBase ID: 174796
• Molecular Formular: C35H34ClNO5S
• Molecular Mass: 616.16616
• Monoisotopic Mass: 615.18462187
• SMILES: c1cc(cc2c1ccc(n2)/C=C/c1cccc(c1)[C@@H](CCc1c(cccc1)C(O)(C)C(=O)O)SCC1(CC(=O)O)CC1)Cl
• Canonical SMILES: OC(=O)CC1(CS[C@@H](c2cccc(c2)/C=C/c2ccc3c(n2)cc(cc3)Cl)CCc2ccccc2C(C(=O)O)(O)C)CC1
• InChI: InChI=1S/C35H34ClNO5S/c1-34(42,33(40)41)29-8-3-2-6-24(29)12-16-31(43-22-35(17-18-35)21-32(38)39)26-7-4-5-23(19-26)9-14-28-15-11-25-10-13-27(36)20-30(25)37-28/h2-11,13-15,19-20,31,42H,12,16-18,21-22H2,1H3,(H,38,39)(H,40,41)/b14-9+/t31-,34?/m1/s1
• InChIKey: FJSYYPGNUBZDIM-VZLZVWCJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{2-[(3R)-3-({[1-(carboxymethyl)cyclopropyl]methyl}sulfanyl)-3-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}propyl]phenyl}-2-hydroxypropanoic acid
• IUPAC Traditional name: 2-{2-[(3R)-3-({[1-(carboxymethyl)cyclopropyl]methyl}sulfanyl)-3-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}propyl]phenyl}-2-hydroxypropanoic acid
• Synonyms: 2-[(3R)-3-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-3-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]propyl]-α-hydroxy-α-methylbenzeneacetic Acid; Montelukast Dicarboxylic Acid(Mixture of Diastereomers)

Database IDs

• CAS Number: 213380-27-9
• PubChem SID: 164230706
• PubChem CID: 9873776

CALCULATED PROPERTIES

• Acid pKa: 3.776053
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 5.2576685
• LogD (pH = 7.4): 1.9541918
• Log P: 7.673303
• Molar Refractivity: 170.9901 cm^3
• Polarizability: 67.56894 Å^3
• Polar Surface Area: 107.72 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M568045

A biliary metabolite of Montelukast sodium (M568000).

REFERENCES

• Chiba, M., et al.: Drug Metab. Dispos., 25, 1022 (1997)
• Delepeleire, I., et al.: Clin. Pharmacol.Ther., 61, 83 (1997)