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

• ChemBase ID: 174790
• Molecular Formular: C35H36ClNO4S
• Molecular Mass: 602.18264
• Monoisotopic Mass: 601.20535732
• SMILES: c1cc(cc2c1ccc(n2)/C=C/c1cccc(c1)[C@@H](CCc1c(cccc1)C(C)(CO)O)SCC1(CC1)CC(=O)O)Cl
• Canonical SMILES: OCC(c1ccccc1CC[C@H](c1cccc(c1)/C=C/c1ccc2c(n1)cc(cc2)Cl)SCC1(CC1)CC(=O)O)(O)C
• InChI: InChI=1S/C35H36ClNO4S/c1-34(41,22-38)30-8-3-2-6-25(30)12-16-32(42-23-35(17-18-35)21-33(39)40)27-7-4-5-24(19-27)9-14-29-15-11-26-10-13-28(36)20-31(26)37-29/h2-11,13-15,19-20,32,38,41H,12,16-18,21-23H2,1H3,(H,39,40)/b14-9+/t32-,34?/m1/s1
• InChIKey: UFQIEVSCRCMNLW-SHISVWIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(1,2-dihydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid
• IUPAC Traditional name: [1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-[2-(1,2-dihydroxypropan-2-yl)phenyl]propyl]sulfanyl}methyl)cyclopropyl]acetic acid
• Synonyms: 1-[1-[[[(1R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1,2-diol-2-methylethyl)phenyl]propyl]thio]methyl]cyclopropaneacetic; M6a,b; Montelukast 1,2-Diol(Mixture of Diastereomers)

Database IDs

• CAS Number: 186352-97-6
• PubChem SID: 164230700
• PubChem CID: 9960377

CALCULATED PROPERTIES

• Acid pKa: 4.398714
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 6.4973807
• LogD (pH = 7.4): 4.747015
• Log P: 7.4460278
• Molar Refractivity: 171.0476 cm^3
• Polarizability: 67.692154 Å^3
• Polar Surface Area: 90.65 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Methanol
• Apperance: Yellow Solid
• Melting Point: 78-80°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M568015

The methyl-hydroxylated metabolite of Montelukast.

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)