(2S,3S,4S,5R,6S)-6-[4-(dipropylsulfamoyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 176926
• Molecular Formular: C19H27NO10S
• Molecular Mass: 461.48338
• Monoisotopic Mass: 461.13556707
• SMILES: c1cc(ccc1S(=O)(=O)N(CCC)CCC)C(=O)O[C@H]1[C@H]([C@H]([C@@H]([C@@H](O1)C(=O)O)O)O)O
• Canonical SMILES: CCCN(S(=O)(=O)c1ccc(cc1)C(=O)O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)CCC
• InChI: InChI=1S/C19H27NO10S/c1-3-9-20(10-4-2)31(27,28)12-7-5-11(6-8-12)18(26)30-19-15(23)13(21)14(22)16(29-19)17(24)25/h5-8,13-16,19,21-23H,3-4,9-10H2,1-2H3,(H,24,25)/t13-,14-,15+,16-,19-/m0/s1
• InChIKey: BZOGRYWIYJNLDE-NAHJCDBISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6S)-6-[4-(dipropylsulfamoyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6S)-6-[4-(dipropylsulfamoyl)benzoyloxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: 1-[4-[(Dipropylamino)sulfonyl]benzoate] β-D-Glucopyranuronic Acid; 1-[p-(Dipropylsulfamoyl)benzoate] β-D-Glucopyranuronic Acid; Probenecid Glucuronide; Probenecid Acyl β-D-Glucuronide

Database IDs

• CAS Number: 34017-15-7
• PubChem SID: 164232836
• PubChem CID: 182154

CALCULATED PROPERTIES

• Acid pKa: 2.8022041
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -1.9438941
• LogD (pH = 7.4): -2.7987998
• Log P: 0.6950788
• Molar Refractivity: 106.1093 cm^3
• Polarizability: 42.90953 Å^3
• Polar Surface Area: 170.9 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: White Solid
• Melting Point: 136-139°C°C

Safety Information

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

DETAILS

Toronto Research Chemicals - P755010

The major metabolite of Probenecid (P755000).

REFERENCES

• Blanckaert, N., et al.: Biochem. J., 171, 203 (1978)
• Worrall, S., et al.: Life Sci., 56, 1921 (1978)
• Presle, N., et al.: Drug Metab. Disos., 24, 1050 (1978)
• Akira, K., et al.: J. Pharmacol. Toxicol. Methods, 37, 237 (1978)
• Terrier, N., et al.: Mol. P