2-(1-{[(1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[4-hydroxy-2-(2-hydroxypropan-2-yl)phenyl]propyl)sulfanyl]methyl}cyclopropyl)acetic acid

• ChemBase ID: 170941
• Molecular Formular: C35H36ClNO4S
• Molecular Mass: 602.18264
• Monoisotopic Mass: 601.20535732
• SMILES: c1cc(cc2c1ccc(n2)/C=C/c1cccc(c1)C(CCc1c(cc(cc1)O)C(C)(O)C)SCC1(CC(=O)O)CC1)Cl
• Canonical SMILES: OC(=O)CC1(CSC(c2cccc(c2)/C=C/c2ccc3c(n2)cc(cc3)Cl)CCc2ccc(cc2C(O)(C)C)O)CC1
• InChI: InChI=1S/C35H36ClNO4S/c1-34(2,41)30-20-29(38)14-9-24(30)10-15-32(42-22-35(16-17-35)21-33(39)40)26-5-3-4-23(18-26)6-12-28-13-8-25-7-11-27(36)19-31(25)37-28/h3-9,11-14,18-20,32,38,41H,10,15-17,21-22H2,1-2H3,(H,39,40)/b12-6+
• InChIKey: OUCJSWWLSUSPOP-WUXMJOGZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(1-{[(1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[4-hydroxy-2-(2-hydroxypropan-2-yl)phenyl]propyl)sulfanyl]methyl}cyclopropyl)acetic acid
• IUPAC Traditional name: (1-{[(1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[4-hydroxy-2-(2-hydroxypropan-2-yl)phenyl]propyl)sulfanyl]methyl}cyclopropyl)acetic acid
• Synonyms: Montelukast M3; 25-Hydroxy Montelukast; 1-[[[(1R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[4-hydroxy-2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic Acid

Database IDs

• CAS Number: 200804-28-0
• PubChem SID: 164226851
• PubChem CID: 46781842

CALCULATED PROPERTIES

• Acid pKa: 4.3911324
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 7.233249
• LogD (pH = 7.4): 5.481967
• Log P: 8.18697
• Molar Refractivity: 171.4848 cm^3
• Polarizability: 67.675705 Å^3
• Polar Surface Area: 90.65 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H948465

A metabolite of Montelukast.

REFERENCES

• Cheng, H., et al.: Drug Metab. Dispos., 22, 139 (1994)
• Gorenne, I., et al.: Eur. J. Pharmacol., 275, 207 (1994)
• Chiba, M., et al.: Drug Metab. Dispos., 25, 1022 (1994)
• Delepeleire, I., et al.: Clin. Pharmacol. Ther., 61, 83 (1994)