(2S,3S,4S,5R,6R)-6-[(1R,2R)-2-(2,2-dichloroacetamido)-3-hydroxy-1-(4-nitrophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

• ChemBase ID: 164054
• Molecular Formular: C17H20Cl2N2O11
• Molecular Mass: 499.2535
• Monoisotopic Mass: 498.04441483
• SMILES: c1c(ccc(c1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)[N+](=O)[O-]
• Canonical SMILES: OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O)NC(=O)C(Cl)Cl
• InChI: InChI=1S/C17H20Cl2N2O11/c18-14(19)15(26)20-8(5-22)12(6-1-3-7(4-2-6)21(29)30)31-17-11(25)9(23)10(24)13(32-17)16(27)28/h1-4,8-14,17,22-25H,5H2,(H,20,26)(H,27,28)/t8-,9+,10+,11-,12-,13+,17-/m1/s1
• InChIKey: DCHLHOYWKBFSDE-IHYHKNIHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4S,5R,6R)-6-[(1R,2R)-2-(2,2-dichloroacetamido)-3-hydroxy-1-(4-nitrophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• IUPAC Traditional name: (2S,3S,4S,5R,6R)-6-[(1R,2R)-2-(2,2-dichloroacetamido)-3-hydroxy-1-(4-nitrophenyl)propoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• Synonyms: (1R,2R)-2-[(2,2-Dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl β-D-Glucopyranosiduronic Acid; Chloramphenicol 1-O-β-D-Glucuronide

Database IDs

• CAS Number: 1013074-93-5
• PubChem SID: 162258189
• PubChem CID: 71314670

CALCULATED PROPERTIES

• Log P: -0.57185763
• Molar Refractivity: 105.4814 cm^3
• Polarizability: 41.653748 Å^3
• Polar Surface Area: 211.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false
• Acid pKa: 3.1116226
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.9337194
• LogD (pH = 7.4): -4.164222

DETAILS

Toronto Research Chemicals - C325040

The minor glucuronide metabolite of Chloramphenicol (C325030).

REFERENCES

• Simons, P., et al.: Xenobiotica, 22, 1267 (1992)
• Kaji, H., et al.: Drug Metab. Dispos., 33, 60 (1992)