methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(2R,3S)-3-(acetyloxy)-2-(2,2-dichloroacetamido)-3-(4-nitrophenyl)propoxy]oxane-2-carboxylate

• ChemBase ID: 164056
• Molecular Formular: C26H30Cl2N2O15
• Molecular Mass: 681.4268
• Monoisotopic Mass: 680.10232363
• SMILES: c1c(ccc(c1)[C@@H]([C@@H](CO[C@@H]1O[C@H]([C@H]([C@@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C)C(=O)OC)NC(=O)C(Cl)Cl)OC(=O)C)[N+](=O)[O-]
• Canonical SMILES: COC(=O)[C@@H]1O[C@@H](OC[C@H]([C@H](c2ccc(cc2)[N+](=O)[O-])OC(=O)C)NC(=O)C(Cl)Cl)[C@H]([C@H]([C@@H]1OC(=O)C)OC(=O)C)OC(=O)C
• InChI: InChI=1S/C26H30Cl2N2O15/c1-11(31)41-18(15-6-8-16(9-7-15)30(37)38)17(29-24(35)23(27)28)10-40-26-22(44-14(4)34)20(43-13(3)33)19(42-12(2)32)21(45-26)25(36)39-5/h6-9,17-23,26H,10H2,1-5H3,(H,29,35)/t17-,18+,19+,20+,21+,22-,26-/m1/s1
• InChIKey: UUUVKPPGQNGBDP-ZJAFXRPMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(2R,3S)-3-(acetyloxy)-2-(2,2-dichloroacetamido)-3-(4-nitrophenyl)propoxy]oxane-2-carboxylate
• IUPAC Traditional name: methyl (2S,3S,4S,5R,6R)-3,4,5-tris(acetyloxy)-6-[(2R,3S)-3-(acetyloxy)-2-(2,2-dichloroacetamido)-3-(4-nitrophenyl)propoxy]oxane-2-carboxylate
• Synonyms: (2R,3R)-2-[(2,2-dichloroacetyl)amino]-3-O-acetate-3-(4-nitrophenyl)propyl β-D-Glucuronide-2’,3’,4’-tri-O-acetate Methyl Ester; Chloramphenicol 3-O-β-D-Glucuronide-3,2',3',4'-tetra-O-acetate Methyl Ester

Database IDs

• PubChem SID: 162258191
• PubChem CID: 71314671

CALCULATED PROPERTIES

• Acid pKa: 7.8659515
• H Acceptors: 10
• H Donor: 1
• LogD (pH = 5.5): 1.3368853
• LogD (pH = 7.4): 1.2273968
• Log P: 1.338538
• Molar Refractivity: 146.8565 cm^3
• Polarizability: 59.09651 Å^3
• Polar Surface Area: 224.88 Å^2
• Rotatable Bonds: 18
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; Ethyl Acetate
• Apperance: White Foam

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C325055

Protected metabolite of Chloramphenicol (C325030).

REFERENCES

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