N-(4-{[(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](methyl)sulfamoyl}phenyl)acetamide

• ChemBase ID: 159129
• Molecular Formular: C45H77N3O15S
• Molecular Mass: 932.16898
• Monoisotopic Mass: 931.50753978
• SMILES: [C@@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@H](CN([C@@H]([C@H]1O)C)C)C)(O)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(S(=O)(=O)c1ccc(cc1)NC(=O)C)C)O)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)CC)(O)C
• Canonical SMILES: CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)[C@@H]([C@](C2)(C)OC)O)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H]([C@H]2O)N(S(=O)(=O)c2ccc(cc2)NC(=O)C)C)[C@](C[C@H](CN([C@@H]([C@H]([C@]1(C)O)O)C)C)C)(C)O
• InChI: InChI=1S/C45H77N3O15S/c1-15-34-45(11,55)38(51)28(6)47(12)23-24(2)21-43(9,54)40(26(4)37(27(5)41(53)61-34)62-35-22-44(10,58-14)39(52)29(7)60-35)63-42-36(50)33(20-25(3)59-42)48(13)64(56,57)32-18-16-31(17-19-32)46-30(8)49/h16-19,24-29,33-40,42,50-52,54-55H,15,20-23H2,1-14H3,(H,46,49)/t24-,25-,26+,27-,28-,29+,33+,34-,35+,36-,37+,38-,39+,40-,42+,43-,44-,45-/m1/s1
• InChIKey: UXWVLGKGQGGAID-SYARVETMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(4-{[(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](methyl)sulfamoyl}phenyl)acetamide
• IUPAC Traditional name: N-(4-{[(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](methyl)sulfamoyl}phenyl)acetamide
• Synonyms: Azithromycin Impurity H; 3'-N-[[4-(Acetylamino)phenyl]sulfonyl]-3'-N-demethyl Azithromycin; (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[[3-[[[4-(Acetylamino)phenyl]sulfonyl]methylamino]-3,4,6-trideoxy-β-D-xylo-hexopyranosyl]oxy]-13-[(2,6-dideoxy-3-C-methyl-3-O-methyl-α-L-ribo-hexopyranosyl)oxy]-2-ethyl-3,4,10-trihydroxy-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

Database IDs

• CAS Number: 612069-30-4
• PubChem SID: 162253264
• PubChem CID: 71312817

CALCULATED PROPERTIES

• Acid pKa: 12.37209
• H Acceptors: 15
• H Donor: 6
• LogD (pH = 5.5): -0.8368986
• LogD (pH = 7.4): 0.5269536
• Log P: 2.5189512
• Molar Refractivity: 236.9924 cm^3
• Polarizability: 95.47261 Å^3
• Polar Surface Area: 243.32 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A168295

3'-N-[[4-(acetylamino)phenyl]sulfonyl]-3'-N-demethyl Azithromycin is an impurity of Azithromycin (A927000).

REFERENCES

• Debremaeker, D. et al.: Rap. Comm. Mass. Spec., 17, 342 (2003)