(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-azacyclopentadecan-15-one

• ChemBase ID: 165834
• Molecular Formular: C37H70N2O12
• Molecular Mass: 734.9579
• Monoisotopic Mass: 734.49287569
• 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)(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](CN[C@@H]([C@H]([C@]1(C)O)O)C)C)(C)O
• InChI: InChI=1S/C37H70N2O12/c1-14-26-37(10,45)30(41)23(6)38-18-19(2)16-35(8,44)32(51-34-28(40)25(39(11)12)15-20(3)47-34)21(4)29(22(5)33(43)49-26)50-27-17-36(9,46-13)31(42)24(7)48-27/h19-32,34,38,40-42,44-45H,14-18H2,1-13H3/t19-,20-,21+,22-,23-,24+,25+,26-,27+,28-,29+,30-,31+,32-,34+,35-,36-,37-/m1/s1
• InChIKey: HRKNNHYKWGYTEN-HOQMJRDDSA-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-azacyclopentadecan-15-one
• 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-azacyclopentadecan-15-one
• Synonyms: Azaerythromycin A; Azathramycin; Desmethylazithromycin; 9-Deoxo-9a-aza-9a-homo Erythromycin A(Desmethyl Azithromycin)

Database IDs

• CAS Number: 76801-85-9
• PubChem SID: 162259967
• PubChem CID: 9810601

CALCULATED PROPERTIES

• Acid pKa: 12.429625
• H Acceptors: 13
• H Donor: 6
• LogD (pH = 5.5): -4.370175
• LogD (pH = 7.4): -1.848046
• Log P: 2.0617337
• Molar Refractivity: 188.8135 cm^3
• Polarizability: 77.17386 Å^3
• Polar Surface Area: 188.87 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Dichloromethane
• Apperance: Off-White Solid
• Melting Point: 126-136°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - D231500

Novel intermediate of Azithromycin that acts as antibiotic.

REFERENCES

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