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

• ChemBase ID: 170938
• Molecular Formular: C35H36ClNO4S
• Molecular Mass: 602.18264
• Monoisotopic Mass: 601.20535732
• SMILES: c1cc(cc2c1ccc(n2)/C=C/c1cccc(c1)[C@@H](C[C@@H](c1c(cccc1)C(O)(C)C)O)SCC1(CC(=O)O)CC1)Cl
• Canonical SMILES: OC(=O)CC1(CS[C@@H](c2cccc(c2)/C=C/c2ccc3c(n2)cc(cc3)Cl)C[C@@H](c2ccccc2C(O)(C)C)O)CC1
• InChI: InChI=1S/C35H36ClNO4S/c1-34(2,41)29-9-4-3-8-28(29)31(38)20-32(42-22-35(16-17-35)21-33(39)40)25-7-5-6-23(18-25)10-14-27-15-12-24-11-13-26(36)19-30(24)37-27/h3-15,18-19,31-32,38,41H,16-17,20-22H2,1-2H3,(H,39,40)/b14-10+/t31-,32+/m0/s1
• InChIKey: CHRNGXJVKOMERP-SIOAQITRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[1-({[(1R,3S)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxy-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid
• IUPAC Traditional name: [1-({[(1R,3S)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-hydroxy-3-[2-(2-hydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid
• Synonyms: [R-[R*,S*-(E)]]-1-[[[1-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxy-3-[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-cyclopropaneacetic Acid; Montelukast M5a; 21(S)-Hydroxy Montelukast

Database IDs

• CAS Number: 184763-29-9
• PubChem SID: 164226848
• PubChem CID: 10841306

CALCULATED PROPERTIES

• Acid pKa: 4.25548
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 6.097098
• LogD (pH = 7.4): 4.3789186
• Log P: 7.137863
• Molar Refractivity: 170.9758 cm^3
• Polarizability: 67.76459 Å^3
• Polar Surface Area: 90.65 Å^2
• Rotatable Bonds: 12
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform
• Apperance: Pale Yellow Solid
• Melting Point: 71-75°C

Safety Information

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

DETAILS

Toronto Research Chemicals - H948461

A metabolite of Montelukast (M568000).

REFERENCES

• Madan, A., et al.: Biochem. Pharmacol., 46, 2291 (1993)
• Blake, B.L., et al.: Xenobiotica, 25, 377 (1993)
• LaBelle, M., et al.: Bioorg. Med. Chem. Lett., 5, 283 (1993)
• Chiba, M., et al.: Drug Metab. Dispos., 24, 307 (1993)