(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}-11-{[(2S,3S,6R)-3-hydroxy-6-methyl-4-oxooxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

• ChemBase ID: 166174
• Molecular Formular: C36H65NO13
• Molecular Mass: 719.9002
• Monoisotopic Mass: 719.44559115
• 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(=O)C[C@H](O1)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)CC(=O)[C@H]2O)[C@](C[C@H](CN([C@@H]([C@H]([C@]1(C)O)O)C)C)C)(C)O
• InChI: InChI=1S/C36H65NO13/c1-13-25-36(10,44)29(40)22(6)37(11)17-18(2)15-34(8,43)31(50-33-27(39)24(38)14-19(3)46-33)20(4)28(21(5)32(42)48-25)49-26-16-35(9,45-12)30(41)23(7)47-26/h18-23,25-31,33,39-41,43-44H,13-17H2,1-12H3/t18-,19-,20+,21-,22-,23+,25-,26+,27-,28+,29-,30+,31-,33+,34-,35-,36-/m1/s1
• InChIKey: AMNAVVMCWWSBHN-AWHKAWBESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (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}-11-{[(2S,3S,6R)-3-hydroxy-6-methyl-4-oxooxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
• IUPAC Traditional name: (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}-11-{[(2S,3S,6R)-3-hydroxy-6-methyl-4-oxooxan-2-yl]oxy}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
• Synonyms: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[[4,6-dideoxy-β-D-erythro-hexopyranos-3-ulos-1-yl]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; 3’-De(dimethylamino)-3’-oxoazithromycin; 3'-Des(dimethylamino)-3'-keto Azithromycin

Database IDs

• CAS Number: 612069-25-7
• PubChem SID: 162260307
• PubChem CID: 71315597

CALCULATED PROPERTIES

• Acid pKa: 11.616313
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -0.64902467
• LogD (pH = 7.4): 1.0563958
• Log P: 2.376075
• Molar Refractivity: 181.3736 cm^3
• Polarizability: 73.93106 Å^3
• Polar Surface Area: 193.91 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D288910

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

REFERENCES

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