(2S,5S)-2-(3-methanesulfonyl-5-methoxy-4-propoxyphenyl)-5-(3,4,5-trimethoxyphenyl)oxolane

• ChemBase ID: 172145
• Molecular Formular: C24H32O8S
• Molecular Mass: 480.57108
• Monoisotopic Mass: 480.18178898
• SMILES: C1C[C@H](O[C@@H]1c1cc(c(c(c1)OC)OC)OC)c1cc(c(c(c1)S(=O)(=O)C)OCCC)OC
• Canonical SMILES: CCCOc1c(OC)cc(cc1S(=O)(=O)C)[C@@H]1CC[C@H](O1)c1cc(OC)c(c(c1)OC)OC
• InChI: InChI=1S/C24H32O8S/c1-7-10-31-24-21(29-4)13-16(14-22(24)33(6,25)26)18-9-8-17(32-18)15-11-19(27-2)23(30-5)20(12-15)28-3/h11-14,17-18H,7-10H2,1-6H3/t17-,18-/m0/s1
• InChIKey: NZWPFJNQOZFEDT-ROUUACIJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,5S)-2-(3-methanesulfonyl-5-methoxy-4-propoxyphenyl)-5-(3,4,5-trimethoxyphenyl)oxolane
• IUPAC Traditional name: (2S,5S)-2-(3-methanesulfonyl-5-methoxy-4-propoxyphenyl)-5-(3,4,5-trimethoxyphenyl)oxolane
• Synonyms: (2R,5R)-rel-Tetrahydro-2-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-5-(3,4,5-trimethoxyphenyl)furan; L 659989; trans-(±)-Tetrahydro-2-[3-methoxy-5-(methylsulfonyl)-4-propoxyphenyl]-5-(3,4,5-trimethoxyphenyl)furan; L-659989

Database IDs

• CAS Number: 113787-28-3
• PubChem SID: 164228055
• PubChem CID: 9934870

CALCULATED PROPERTIES

• Acid pKa: 19.572954
• H Acceptors: 8
• H Donor: 0
• LogD (pH = 5.5): 3.03011
• LogD (pH = 7.4): 3.03011
• Log P: 3.03011
• Molar Refractivity: 124.7113 cm^3
• Polarizability: 49.549297 Å^3
• Polar Surface Area: 89.52 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - L009500

L-659989 is a platelet-activating factor (PAF) receptor antagonist. L-659989 is also a potent inhibitor of phospholipase D activity at higher concentrations. L-659989 showed cardioprotective effects as it inhibited heart injury from ischemia and reperfusi

REFERENCES

• Hussaini, I.M. et al.: Acta Pharmacol. Sin., 21, 897 (2000)
• Gomez-M. et al.: Biochim. Biophys. Acta, 1438, 247 (2000)
• Ioculano, M. et al.: J. Cardio. Pharmacol., 23, 7 (2000)