2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole

• ChemBase ID: 177324
• Molecular Formular: C18H21N3O3S
• Molecular Mass: 359.44264
• Monoisotopic Mass: 359.13036255
• SMILES: c1ccc2c(c1)nc([nH]2)[S@@](=O)Cc1nccc(c1C)OCCCOC
• Canonical SMILES: COCCCOc1ccnc(c1C)C[S@](=O)c1nc2c([nH]1)cccc2
• InChI: InChI=1S/C18H21N3O3S/c1-13-16(19-9-8-17(13)24-11-5-10-23-2)12-25(22)18-20-14-6-3-4-7-15(14)21-18/h3-4,6-9H,5,10-12H2,1-2H3,(H,20,21)/t25-/m0/s1
• InChIKey: YREYEVIYCVEVJK-VWLOTQADSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{[4-(3-methoxypropoxy)-3-methylpyridin-2-yl]methanesulfinyl}-1H-1,3-benzodiazole
• IUPAC Traditional name: irsogladine maleate
• Synonyms: 2-[(S)-[[4-(3-Methoxypropoxy)-3-methyl-2-pyridinyl]methyl]sulfinyl]-1H-benzimidazole; S-(-)-Rabeprazole; (S)-Rabeprazole

Database IDs

• CAS Number: 177795-59-4
• PubChem SID: 164233234
• PubChem CID: 10833710

CALCULATED PROPERTIES

• Acid pKa: 9.346711
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.0682993
• LogD (pH = 7.4): 2.0861723
• Log P: 2.0907433
• Molar Refractivity: 98.0668 cm^3
• Polarizability: 39.284637 Å^3
• Polar Surface Area: 77.1 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R070525

A partially reversible gastric proton pump inhibitor.

REFERENCES

• Moda, T., et al.: Lett. Drug Des. Discov., 4, 502 (2007)
• Belaz, K., et al.: J. Pharm. Biomed. Anal., 47, 81 (2007)