(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecane-7,15-dione

• ChemBase ID: 160931
• 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)C(=O)N[C@@H]([C@H]1O)C)(O)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)CC)(C)O
• 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(C)C)[C@](C[C@H](C(=O)N[C@@H]([C@H]([C@]1(C)O)O)C)C)(C)O
• InChI: InChI=1S/C37H68N2O13/c1-14-25-37(10,46)29(41)22(6)38-32(43)18(2)16-35(8,45)31(52-34-27(40)24(39(11)12)15-19(3)48-34)20(4)28(21(5)33(44)50-25)51-26-17-36(9,47-13)30(42)23(7)49-26/h18-31,34,40-42,45-46H,14-17H2,1-13H3,(H,38,43)/t18-,19-,20+,21-,22-,23+,24+,25-,26+,27-,28+,29-,30+,31-,34+,35-,36-,37-/m1/s1
• InChIKey: UXDNUPFGRUGPKK-XBWOTNPQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecane-7,15-dione
• IUPAC Traditional name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-2-ethyl-3,4,10-trihydroxy-13-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecane-7,15-dione
• Synonyms: 9a-aza-9a-homo Erythromycin A; (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-3,5,8,10,12,14-hexamethyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-6-azacyclopentadecane-7,15-dione

Database IDs

• CAS Number: 76820-32-1
• PubChem SID: 162255066
• PubChem CID: 21673481

CALCULATED PROPERTIES

• Acid pKa: 12.413933
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -1.7913673
• LogD (pH = 7.4): -0.23651244
• Log P: 1.4472188
• Molar Refractivity: 188.9399 cm^3
• Polarizability: 76.91697 Å^3
• Polar Surface Area: 205.94 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Dichloromethane; Methanol
• Apperance: Off-White Solid

DETAILS

Toronto Research Chemicals - A797800

Novel intermediate of Azithromycin that acts as antibiotic.

REFERENCES

• Krajacic, M.B., et al.: J. Antibiot., 58, 380 (2005)