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

• ChemBase ID: 164055
• Molecular Formular: C17H20Cl2N2O11
• Molecular Mass: 499.2535
• Monoisotopic Mass: 498.04441483
• SMILES: c1c(ccc(c1)[C@H]([C@@H](CO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1O)O)O)C(=O)O)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Canonical SMILES: O=C(C(Cl)Cl)N[C@@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)CO[C@@H]1O[C@@H](C(=O)O)[C@H]([C@@H]([C@@H]1O)O)O
• InChI: InChI=1S/C17H20Cl2N2O11/c18-14(19)15(26)20-8(9(22)6-1-3-7(4-2-6)21(29)30)5-31-17-12(25)10(23)11(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: UARPTSDFEIFMJP-PEXHWNMISA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 39751-33-2
• PubChem SID: 162258190
• PubChem CID: 83960

CALCULATED PROPERTIES

• Acid pKa: 3.1406157
• H Acceptors: 11
• H Donor: 6
• LogD (pH = 5.5): -2.9067402
• LogD (pH = 7.4): -4.159691
• Log P: -0.57185763
• Molar Refractivity: 105.4814 cm^3
• Polarizability: 41.653797 Å^3
• Polar Surface Area: 211.6 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 170-174°C

Safety Information

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

DETAILS

Toronto Research Chemicals - C325045

The major glucuronide metabolite of Chloramphenicol (C325030).

REFERENCES

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