(3R,4S,5S,6R,7R,9R,10E,11S,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-[(2-methoxyethoxy)methoxy]-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-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one

• ChemBase ID: 172947
• Molecular Formular: C45H84N2O17
• Molecular Mass: 925.15166
• Monoisotopic Mass: 924.57699924
• SMILES: [C@@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H](/C(=N\OCOCCOC)/[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)OCOCCOC)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)CC)(O)C
• Canonical SMILES: COCCOCO/N=C/1\[C@H](C)C[C@@](C)(O)[C@H](O[C@@H]2O[C@H](C)C[C@H]([C@H]2OCOCCOC)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/C45H84N2O17/c1-16-33-45(10,52)38(48)28(4)35(46-59-25-57-20-18-54-14)26(2)22-43(8,51)40(64-42-37(58-24-56-19-17-53-13)32(47(11)12)21-27(3)60-42)29(5)36(30(6)41(50)62-33)63-34-23-44(9,55-15)39(49)31(7)61-34/h26-34,36-40,42,48-49,51-52H,16-25H2,1-15H3/b46-35+/t26-,27-,28+,29+,30-,31+,32+,33-,34+,36+,37-,38-,39+,40-,42+,43-,44-,45-/m1/s1
• InChIKey: KYAPHMSJPGQOSY-OTHJGQCISA-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-[(2-methoxyethoxy)methoxy]-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-(2,4,7-trioxa-1-azaoctan-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-[(2-methoxyethoxy)methoxy]-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-(2,4,7-trioxa-1-azaoctan-1-ylidene)-1-oxacyclotetradecan-2-one
• Synonyms: (9E)-2'-O-[(2-Methoxyethoxy)methyl] Erythromycin 9-[O-[(2-Methoxyethoxy)methyl]oxime]; 2'-O-[(2-Methoxyethoxy)methyl] Roxithromycin

Database IDs

• CAS Number: 425365-66-8
• PubChem SID: 164228857
• PubChem CID: 71750076

CALCULATED PROPERTIES

• Acid pKa: 12.688881
• H Acceptors: 18
• H Donor: 4
• LogD (pH = 5.5): 0.4450666
• LogD (pH = 7.4): 2.0262074
• Log P: 3.6592557
• Molar Refractivity: 232.8853 cm^3
• Polarizability: 94.75617 Å^3
• Polar Surface Area: 224.35 Å^2
• Rotatable Bonds: 19
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - M262515

Roxithromycin (R700850) structurally related substance in bulk samples. Roxithromycin impurity.

REFERENCES

• Gasc, J., et al.: J. Antibiot., 44, 313 (1991, Chepkwony, H., et al.: J. Chromatogr., 914, 53 (2001)