(2R,3R,4R,5S,6S)-6-[5-(difluoromethoxy)-2-{[(3,4-dimethoxypyridin-2-yl)methyl]sulfanyl}-1H-1,3-benzodiazol-1-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176229
• Molecular Formular: C22H23F2N3O9S
• Molecular Mass: 543.4945264
• Monoisotopic Mass: 543.11230677
• SMILES: O1[C@@H]([C@H](O)[C@@H]([C@H]([C@H]1C(=O)O)O)O)n1c2ccc(cc2nc1SCc1c(c(ccn1)OC)OC)OC(F)F
• Canonical SMILES: COc1c(nccc1OC)CSc1nc2c(n1[C@H]1O[C@H](C(=O)O)[C@@H]([C@H]([C@H]1O)O)O)ccc(c2)OC(F)F
• InChI: InChI=1S/C22H23F2N3O9S/c1-33-13-5-6-25-11(17(13)34-2)8-37-22-26-10-7-9(35-21(23)24)3-4-12(10)27(22)19-16(30)14(28)15(29)18(36-19)20(31)32/h3-7,14-16,18-19,21,28-30H,8H2,1-2H3,(H,31,32)/t14-,15-,16+,18-,19+/m1/s1
• InChIKey: DEFATFFTNRHGJX-VYDRJQSISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4R,5S,6S)-6-[5-(difluoromethoxy)-2-{[(3,4-dimethoxypyridin-2-yl)methyl]sulfanyl}-1H-1,3-benzodiazol-1-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2R,3R,4R,5S,6S)-6-[5-(difluoromethoxy)-2-{[(3,4-dimethoxypyridin-2-yl)methyl]sulfanyl}-1,3-benzodiazol-1-yl]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 5-(Difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl)]thio]-1-β-D-glucopyranosyl-1H-benzimidazole; Pantoprazole Sulfide-β-D-glucuronide

Database IDs

• CAS Number: 867300-67-2
• PubChem SID: 164232139
• PubChem CID: 71751463

CALCULATED PROPERTIES

• Acid pKa: 2.9158666
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -0.49948934
• LogD (pH = 7.4): -1.8056045
• Log P: -0.34081018
• Molar Refractivity: 121.1065 cm^3
• Polarizability: 48.95228 Å^3
• Polar Surface Area: 165.62 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - P190000

Pantoprazole Sulfide-β-D-glucuronide is a metabolite of Pantoprazole (P183000).

REFERENCES

• Abourashed, E., et al.: Curr. Med. Chem., 6, 359 (1999)
• Chatterjee, P., et al.: J. Nat. Prod., 62, 761 (1999)
• Jungnickel, P., et al.: Clin. Ther., 22, 1268 (2000)