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

• ChemBase ID: 166295
• Molecular Formular: C34H32ClNO4S
• Molecular Mass: 586.14018
• Monoisotopic Mass: 585.17405719
• SMILES: c1cc(cc2c1ccc(n2)/C=C/c1cccc(c1)[C@@H](CCc1c(cccc1)C(=O)OC)SCC1(CC(=O)O)CC1)Cl
• Canonical SMILES: COC(=O)c1ccccc1CC[C@H](c1cccc(c1)/C=C/c1ccc2c(n1)cc(cc2)Cl)SCC1(CC1)CC(=O)O
• InChI: InChI=1S/C34H32ClNO4S/c1-40-33(39)29-8-3-2-6-24(29)12-16-31(41-22-34(17-18-34)21-32(37)38)26-7-4-5-23(19-26)9-14-28-15-11-25-10-13-27(35)20-30(25)36-28/h2-11,13-15,19-20,31H,12,16-18,21-22H2,1H3,(H,37,38)/b14-9+/t31-/m1/s1
• InChIKey: FVMXWBDOMBDOJN-JLBZDQGGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(methoxycarbonyl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid
• IUPAC Traditional name: [1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(methoxycarbonyl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid
• Synonyms: 2-[(3R)-3-[[[1-(Carboxymethyl)cyclopropyl]methyl]thio]-3-[3-[(1E)-2-(7-chloro-2-quinolinyl)ethenyl]phenyl]propyl]benzoic Acid 1-Methyl Ester; Montelukast Impurity H; (R)-2-[1-[[[1-[3-[(E)-2-(7-Chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(methoxycarbonyl)phenyl]propyl]thio]methyl]cyclopropyl]acetic Acid; 2-[1-[[[(1R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-(2-methoxycarbonylphenyl)propyl]thio]methyl]cyclopropyl]acetic Acid; 2-[1-[[[(1R)-1-[3-[(1E)-2-(7-Chloroquinolin-2-yl)ethenyl]phenyl]-3-[2-(methoxycarbonyl)phenyl]propyl]sulfanyl]methyl]cyclopropyl]acetic Acid; 2'-Des(1-hydroxy-1-methylethyl)-2'-methycarboxy Montelukast

Database IDs

• PubChem SID: 162260428
• PubChem CID: 11556341

CALCULATED PROPERTIES

• Acid pKa: 4.307373
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 7.5270977
• LogD (pH = 7.4): 5.795609
• Log P: 8.535327
• Molar Refractivity: 165.6563 cm^3
• Polarizability: 65.35119 Å^3
• Polar Surface Area: 76.49 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D290040

An impurity of the selective leukotriene D4-receptor antagonist, Montelukast (M568000).

REFERENCES

• Kumar, I.V. et al.: Asian J. Chem., 23, 4536 (2011)