(2S,3S,4R,5S,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-7-propyl-1-oxa-7-azacyclopentadecan-15-one

• ChemBase ID: 169573
• Molecular Formular: C40H76N2O12
• Molecular Mass: 777.03764
• Monoisotopic Mass: 776.53982588
• SMILES: N1([C@@H](CC([C@@H]([C@H]([C@H]([C@H](C(=O)O[C@@H](C([C@@H]([C@H](C1)C)O)(O)C)CC)C)O[C@@H]1O[C@@H]([C@@H]([C@](C1)(C)OC)O)C)C)O[C@H]1[C@@H]([C@@H](C[C@H](O1)C)N(C)C)O)(O)C)C)CCC
• Canonical SMILES: CCCN1C[C@H](C)[C@@H](O)C(C)(O)[C@@H](CC)OC(=O)[C@@H]([C@@H]([C@@H]([C@H](C(C[C@H]1C)(C)O)O[C@@H]1O[C@H](C)C[C@H]([C@H]1O)N(C)C)C)O[C@@H]1O[C@H](C)[C@@H]([C@](C1)(C)OC)O)C
• InChI: InChI=1S/C40H76N2O12/c1-15-17-42-21-22(3)33(44)40(11,48)29(16-2)52-36(46)26(7)32(53-30-20-39(10,49-14)34(45)27(8)51-30)25(6)35(38(9,47)19-23(42)4)54-37-31(43)28(41(12)13)18-24(5)50-37/h22-35,37,43-45,47-48H,15-21H2,1-14H3/t22-,23+,24+,25-,26+,27-,28-,29-,30-,31+,32-,33+,34-,35+,37-,38+,39+,40+/m0/s1
• InChIKey: VWAMTBXLZPEDQO-SARCLEJTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5S,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-7-propyl-1-oxa-7-azacyclopentadecan-15-one
• IUPAC Traditional name: (2S,3S,4R,5S,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-7-propyl-1-oxa-7-azacyclopentadecan-15-one
• Synonyms: (2R,3S,4R,5S,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-7-propyl-11-[[3,4,6-trideoxy-3-(dimethylamino)-β-D-xylo-hexopyranosyl]oxy]-1-oxa-7-azacyclopentadecan-15-one; ML 1709460; Gamithromycin

Database IDs

• CAS Number: 145435-72-9
• PubChem SID: 162263705
• PubChem CID: 71317037

CALCULATED PROPERTIES

• Acid pKa: 12.462237
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -3.7058218
• LogD (pH = 7.4): -1.1511282
• Log P: 2.9810598
• Molar Refractivity: 203.5464 cm^3
• Polarizability: 82.67436 Å^3
• Polar Surface Area: 180.08 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - G195000

A macrolide compound which is known to have antibacterial activity, and is useful in the therapy of bacterial infections in mammals. Antibiotic.

REFERENCES

• Broto, P., et al.: Eur. J. Med. Chem., 19, 71 (1984)
• Farrar, V., et al.: J. Med. Chem., 36, 3517 (1984)
• Clark, D., et al.: J. Pharm. Sci., 88, 807 (1984)