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]formamide

• ChemBase ID: 167220
• 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)CN([C@@H]([C@H]1O)C)C)(O)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)NC=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
• InChI: InChI=1S/C37H68N2O13/c1-13-26-37(10,46)30(42)23(6)39(11)17-19(2)15-35(8,45)32(52-34-28(41)25(38-18-40)14-20(3)48-34)21(4)29(22(5)33(44)50-26)51-27-16-36(9,47-12)31(43)24(7)49-27/h18-32,34,41-43,45-46H,13-17H2,1-12H3,(H,38,40)/t19-,20-,21+,22-,23-,24+,25+,26-,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
• InChIKey: FSUFNIVRKKVCSI-HOQMJRDDSA-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]formamide
• 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]formamide
• Synonyms: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-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-11-[[3,4,6-trideoxy-3-(formylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecan-15-one; 3'-N,N-Di(desmethyl)-3'-N-formyl Azithromycin

Database IDs

• CAS Number: 765927-71-7
• PubChem SID: 162261353
• PubChem CID: 71316017

CALCULATED PROPERTIES

• Acid pKa: 12.423415
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -1.9565502
• LogD (pH = 7.4): -0.5926968
• Log P: 1.3993012
• Molar Refractivity: 188.9922 cm^3
• Polarizability: 76.91697 Å^3
• Polar Surface Area: 205.94 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D440860

Azithromycin (A927000) impurity. A degradation products of Azithromycin.

REFERENCES

• Anon., et al.: Pharmaeuropa, 13, 750 (2001)