(2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-amino-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}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one

• ChemBase ID: 167219
• Molecular Formular: C36H68N2O12
• Molecular Mass: 720.93132
• Monoisotopic Mass: 720.47722563
• 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)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@H](CN([C@@H]([C@H]([C@]1(C)O)O)C)C)C)(C)O
• InChI: InChI=1S/C36H68N2O12/c1-13-25-36(10,44)29(40)22(6)38(11)17-18(2)15-34(8,43)31(50-33-27(39)24(37)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/h18-31,33,39-41,43-44H,13-17,37H2,1-12H3/t18-,19-,20+,21-,22-,23+,24+,25-,26+,27-,28+,29-,30+,31-,33+,34-,35-,36-/m1/s1
• InChIKey: PCDDIDGPAIGEHC-GGNUPITBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-amino-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}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
• IUPAC Traditional name: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-{[(2S,3R,4S,6R)-4-amino-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}-3,5,6,8,10,12,14-heptamethyl-1-oxa-6-azacyclopentadecan-15-one
• Synonyms: (2R,3S,4R,5R,8R,10R,11R,12S,13S,14R)-11-[(3-Amino-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; Aminoazithromycin A; 3'-N,N-Di(desmethyl) Azithromycin

Database IDs

• CAS Number: 612069-27-9
• PubChem SID: 162261352
• PubChem CID: 59659945

CALCULATED PROPERTIES

• Acid pKa: 12.435368
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -4.727916
• LogD (pH = 7.4): -2.5496109
• Log P: 1.6291533
• Molar Refractivity: 184.0389 cm^3
• Polarizability: 75.34145 Å^3
• Polar Surface Area: 202.86 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - D440850

A metabolite of Azithromycin.

REFERENCES

• Bright, G., et al.: J. Antibiotics., 41, 1029 (1988)
• Amacher, D., et al.: Antimicrob. Agents Chemother., 35, 1186 (1988)
• Peters, D., et al.: Drugs, 44, 750 (1988)