(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}-3,5,7,9,11,13-hexamethyl-10-(2,4,6,9-tetraoxa-1-azadecan-1-ylidene)-1-oxacyclotetradecan-2-one

• ChemBase ID: 168177
• Molecular Formular: C42H78N2O16
• Molecular Mass: 867.07252
• Monoisotopic Mass: 866.53513443
• SMILES: [C@@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H](/C(=N\OCOCOCCOC)/[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)(O)C
• Canonical SMILES: COCCOCOCO/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]2O[C@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C(=O)O[C@@H]([C@@]([C@@H]([C@H]1C)O)(C)O)CC)C
• InChI: InChI=1S/C42H78N2O16/c1-15-30-42(10,50)35(46)25(4)32(43-55-22-54-21-53-17-16-51-13)23(2)19-40(8,49)37(60-39-33(45)29(44(11)12)18-24(3)56-39)26(5)34(27(6)38(48)58-30)59-31-20-41(9,52-14)36(47)28(7)57-31/h23-31,33-37,39,45-47,49-50H,15-22H2,1-14H3/b43-32+/t23-,24-,25+,26+,27-,28+,29+,30-,31+,33-,34+,35-,36+,37-,39+,40-,41-,42-/m1/s1
• InChIKey: HPSZFRAOTAULNG-VVYQSLRXSA-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}-3,5,7,9,11,13-hexamethyl-10-(2,4,6,9-tetraoxa-1-azadecan-1-ylidene)-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}-3,5,7,9,11,13-hexamethyl-10-(2,4,6,9-tetraoxa-1-azadecan-1-ylidene)-1-oxacyclotetradecan-2-one
• Synonyms: Roxithromycin impurity G; (9E)-Erythromycin 9-[O-[[(2-Methoxyethoxy)methoxy]methyl]oxime]DISCONTINUED

Database IDs

• CAS Number: 425365-64-6
• PubChem SID: 162262309
• PubChem CID: 71316419

CALCULATED PROPERTIES

• Acid pKa: 12.454023
• H Acceptors: 17
• H Donor: 5
• LogD (pH = 5.5): -0.17573205
• LogD (pH = 7.4): 1.3793703
• Log P: 3.0631046
• Molar Refractivity: 217.0906 cm^3
• Polarizability: 88.46537 Å^3
• Polar Surface Area: 226.12 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E650005

Roxithromycin impurity G, a Roxithromycin homolog.

REFERENCES

• Gasc, J., et al.: Antibiot., 44, 313 (1991)
• Chepkwony, H., et al.: J. Chromatogr., 914, 53 (1991)