N-[(2S,3R,4S,6R)-2-{[(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-15-oxo-1-oxa-6-azacyclopentadecan-11-yl]oxy}-3-hydroxy-6-methyloxan-4-yl]-N-methylformamide

• ChemBase ID: 166440
• Molecular Formular: C38H70N2O13
• Molecular Mass: 762.968
• Monoisotopic Mass: 762.48779031
• SMILES: [C@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@@H](C)CN([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)O)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)CC)(C)O
• Canonical SMILES: O=CN([C@@H]1C[C@@H](C)O[C@H]([C@@H]1O)O[C@@H]1[C@@H](C)[C@H](O[C@@H]2O[C@H](C)[C@@H]([C@](C2)(C)OC)O)[C@@H](C)C(=O)O[C@H](CC)[C@@]([C@@H]([C@H](N(C[C@@H](C[C@@]1(C)O)C)C)C)O)(C)O)C
• InChI: InChI=1S/C38H70N2O13/c1-14-27-38(10,47)31(43)24(6)39(11)18-20(2)16-36(8,46)33(53-35-29(42)26(40(12)19-41)15-21(3)49-35)22(4)30(23(5)34(45)51-27)52-28-17-37(9,48-13)32(44)25(7)50-28/h19-33,35,42-44,46-47H,14-18H2,1-13H3/t20-,21-,22+,23-,24-,25+,26+,27-,28+,29-,30+,31-,32+,33-,35+,36-,37-,38-/m1/s1
• InChIKey: QNGDWLRYIAHQGP-BICOPXKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S,3R,4S,6R)-2-{[(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-15-oxo-1-oxa-6-azacyclopentadecan-11-yl]oxy}-3-hydroxy-6-methyloxan-4-yl]-N-methylformamide
• IUPAC Traditional name: N-[(2S,3R,4S,6R)-2-{[(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-15-oxo-1-oxa-6-azacyclopentadecan-11-yl]oxy}-3-hydroxy-6-methyloxan-4-yl]-N-methylformamide
• Synonyms: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-13-[(2,6-Dideoxy-3-C-methyl-3-O-methyl-α-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-11-[[3,4,6-trideoxy-3-(formylmethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one; 3'-N-Desmethyl-3'-N-formyl Azithromycin

Database IDs

• CAS Number: 612069-28-0
• PubChem SID: 162260573
• PubChem CID: 71315738

CALCULATED PROPERTIES

• Acid pKa: 12.4204035
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -1.7328749
• LogD (pH = 7.4): -0.36902076
• Log P: 1.6229773
• Molar Refractivity: 193.8889 cm^3
• Polarizability: 78.747185 Å^3
• Polar Surface Area: 197.15 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D291635

Azithromycin impurity.

REFERENCES

• Kirst, H., et al.: Antimicrob. Agents Chemother., 33, 1419 (1989)
• Fouda, H., et al.: Ther. Drug Monit., 17, 179 (1989)
• Gandhi, R., et al.: J. Pharm. Biomed. Anal., 23, 1073 (1989)