(2S,3S,4S,5R,6S)-6-({2-[1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-{2-[2-hydroxy(2H6)propan-2-yl]phenyl}propyl]sulfanyl}methyl)cyclopropyl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 174789
• Molecular Formular: C41H44ClNO9S
• Molecular Mass: 762.30736
• Monoisotopic Mass: 761.24253067
• SMILES: O1[C@H]([C@H]([C@H]([C@@H]([C@@H]1C(=O)O)O)O)O)OC(=O)CC1(CS[C@@H](c2cccc(/C=C/c3nc4cc(ccc4cc3)Cl)c2)CCc2c(cccc2)C(O)(C)C)CC1
• Canonical SMILES: O=C(CC1(CS[C@@H](c2cccc(c2)/C=C/c2ccc3c(n2)cc(cc3)Cl)CCc2ccccc2C(O)(C)C)CC1)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C41H44ClNO9S/c1-40(2,50)30-9-4-3-7-25(30)13-17-32(27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(42)21-31(26)43-29)53-23-41(18-19-41)22-33(44)51-39-36(47)34(45)35(46)37(52-39)38(48)49/h3-12,14-16,20-21,32,34-37,39,45-47,50H,13,17-19,22-23H2,1-2H3,(H,48,49)/b15-10+/t32-,34+,35+,36-,37+,39-/m1/s1
• InChIKey: SXJRVQZUUOADNS-IIHPLMAZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-({2-[1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-{2-[2-hydroxy(^2H₆)propan-2-yl]phenyl}propyl]sulfanyl}methyl)cyclopropyl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-({2-[1-({[(1R)-1-{3-[(E)-2-(7-chloroquinolin-2-yl)ethenyl]phenyl}-3-{2-[2-hydroxy(^2H₆)propan-2-yl]phenyl}propyl]sulfanyl}methyl)cyclopropyl]acetyl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: Montelukast Acyl-β-D-glucuronide-d6; 1-[1-[[[(1R)-1-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-(1-hydroxy-1-methylethyl-d6)phenyl]propyl]thio]methyl]cyclopropaneacetate] β-D-Glucopyranuronic Acid

Database IDs

• PubChem SID: 164230699
• PubChem CID: 71750829

CALCULATED PROPERTIES

• Acid pKa: 3.5943532
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 4.6695857
• LogD (pH = 7.4): 3.352613
• Log P: 6.240583
• Molar Refractivity: 201.8025 cm^3
• Polarizability: 80.714 Å^3
• Polar Surface Area: 166.64 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: Yellow Solid
• Melting Point: 141-143°C

Safety Information

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

DETAILS

Toronto Research Chemicals - M568012

A labelled 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)