2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazol-5-ol

• ChemBase ID: 166457
• Molecular Formular: C16H17N3O3S
• Molecular Mass: 331.38948
• Monoisotopic Mass: 331.09906242
• SMILES: c1cc(cc2c1[nH]c(n2)S(=O)Cc1c(c(c(cn1)C)OC)C)O
• Canonical SMILES: COc1c(C)cnc(c1C)CS(=O)c1nc2c([nH]1)ccc(c2)O
• InChI: InChI=1S/C16H17N3O3S/c1-9-7-17-14(10(2)15(9)22-3)8-23(21)16-18-12-5-4-11(20)6-13(12)19-16/h4-7,20H,8H2,1-3H3,(H,18,19)
• InChIKey: TWXDTVZNDQKCOS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazol-5-ol
• IUPAC Traditional name: 2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1H-1,3-benzodiazol-5-ol
• Synonyms: 2-[[(4-Methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazol-5-ol; 5-O-Desmethyl Omeprazole

Database IDs

• CAS Number: 151602-49-2
• PubChem SID: 162260590
• PubChem CID: 10404448

CALCULATED PROPERTIES

• Acid pKa: 9.020618
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.2157333
• LogD (pH = 7.4): 2.2766616
• Log P: 2.287615
• Molar Refractivity: 89.18 cm^3
• Polarizability: 35.437096 Å^3
• Polar Surface Area: 88.1 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dimethyl Sulfoxide; Dimethylformamide; Ethanol; Methanol
• Apperance: Light-Yellow Solid
• Melting Point: 238-240°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D292120

A metabolite of Omeprazole, an antiulcerative.

REFERENCES

• Andersson, T., et al.: Ther. Drug Monit., 12, 415 (1990)
• de Morais, S., et al.: J. Biol. Chem., 269, 15419 (1990)
• Tanigawara, Y., et al.: Clin. Pharmacol. Ther., 66, 528 (1990)
• Abelo, A., et al.: Drug Metab. Disos., 28, 966 (1990)