(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-10-(hydroxyimino)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one

• ChemBase ID: 168178
• Molecular Formular: C37H68N2O13
• Molecular Mass: 748.94142
• Monoisotopic Mass: 748.47214025
• SMILES: [C@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H](/C(=N\O)/[C@@H]([C@H]1O)C)C)(O)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)CC)(C)O
• Canonical SMILES: O/N=C/1\[C@H](C)C[C@@](C)(O)[C@H](O[C@@H]2O[C@H](C)C[C@H]([C@H]2O)N(C)C)[C@@H](C)[C@H](O[C@H]2C[C@@](C)(OC)[C@H]([C@H](O2)C)O)[C@H](C(=O)O[C@@H]([C@@]([C@@H]([C@H]1C)O)(C)O)CC)C
• InChI: InChI=1S/C37H68N2O13/c1-14-25-37(10,45)30(41)20(4)27(38-46)18(2)16-35(8,44)32(52-34-28(40)24(39(11)12)15-19(3)48-34)21(5)29(22(6)33(43)50-25)51-26-17-36(9,47-13)31(42)23(7)49-26/h18-26,28-32,34,40-42,44-46H,14-17H2,1-13H3/b38-27+/t18-,19-,20+,21+,22-,23+,24+,25-,26+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
• InChIKey: KYTWXIARANQMCA-ZTILBQITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-10-(hydroxyimino)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one
• IUPAC Traditional name: (3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-10-(hydroxyimino)-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecan-2-one
• Synonyms: 9-Erythromycin 9-Oxime; 9-Erythromycin A Oxime; Erythromycin Oxime; Roxithromycin Impurity C; Erythromycin A Oxime (Roxithromycin Impurity C)

Database IDs

• CAS Number: 13127-18-9
• PubChem SID: 162262310
• PubChem CID: 6537896

CALCULATED PROPERTIES

• Acid pKa: 9.819748
• H Acceptors: 14
• H Donor: 6
• LogD (pH = 5.5): -0.6312785
• LogD (pH = 7.4): 0.9232951
• Log P: 2.19165
• Molar Refractivity: 189.8588 cm^3
• Polarizability: 77.11856 Å^3
• Polar Surface Area: 209.43 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Choroform; Dichloromethane; Methanol
• Apperance: Off-White Solid
• Melting Point: 159-161°C

Safety Information

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

DETAILS

Toronto Research Chemicals - E650010

The major metabolite of Roxithromycin; also an intermediate of Azithromycin. Antibacterial agent. Roxithromycin impurity C.

REFERENCES

• Ferrero, J., et al.: Drug Metab. Dispos., 18, 441 (1990)
• Gase, C., et al.: J. Antibiot., 44, 313 (1990)
• Markham, A., et al.: Drugs, 48, 297 (1990)
• Jarukamjorn, K., et al.: J. Pharm. Pharmacol., 50, 515 (1990)