(3R,4S,5S,6R,7R,9S,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-9-fluoro-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione

• ChemBase ID: 169122
• Molecular Formular: C37H66FNO13
• Molecular Mass: 751.9172432
• Monoisotopic Mass: 751.4518194
• SMILES: [C@@]1([C@H](OC(=O)[C@@H]([C@H]([C@@H]([C@H]([C@@](C[C@@](C(=O)[C@@H]([C@H]1O)C)(F)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)(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)C[C@H]([C@H]2O)N(C)C)[C@](C[C@](C(=O)[C@@H]([C@H]([C@]1(C)O)O)C)(C)F)(C)O
• InChI: InChI=1S/C37H66FNO13/c1-14-24-37(10,46)29(42)21(5)28(41)34(7,38)17-35(8,45)31(52-33-26(40)23(39(11)12)15-18(2)48-33)19(3)27(20(4)32(44)50-24)51-25-16-36(9,47-13)30(43)22(6)49-25/h18-27,29-31,33,40,42-43,45-46H,14-17H2,1-13H3/t18-,19+,20-,21+,22+,23+,24-,25+,26-,27+,29-,30+,31-,33+,34+,35-,36-,37-/m1/s1
• InChIKey: XOEUHCONYHZURQ-HNUBZJOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R,4S,5S,6R,7R,9S,11R,12R,13S,14R)-6-{[(2S,3R,4S,6R)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy}-14-ethyl-9-fluoro-7,12,13-trihydroxy-4-{[(2R,4R,5S,6S)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy}-3,5,7,9,11,13-hexamethyl-1-oxacyclotetradecane-2,10-dione
• IUPAC Traditional name: flurithromycin
• Synonyms: 8-Fluoroerythromycin; (8S)-8-Fluoroerythromycin A; 8-Fluoroerythromycin A; Antibiotic P 80206; Flurithromycin; P 0501A; P 80206; 8-Fluoro Erythromycin

Database IDs

• CAS Number: 82664-20-8
• PubChem SID: 162263254
• PubChem CID: 71260

CALCULATED PROPERTIES

• Acid pKa: 11.819633
• H Acceptors: 13
• H Donor: 5
• LogD (pH = 5.5): -0.35508764
• LogD (pH = 7.4): 1.4102648
• Log P: 2.4334004
• Molar Refractivity: 185.9324 cm^3
• Polarizability: 75.532104 Å^3
• Polar Surface Area: 193.91 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - F591585

A fluorinated derivative of Erythromycin (E649950). A macrolide antibiotic.

REFERENCES

• Labro, M. et al.: Macrolide Antibiot., 37 (2002)
• Lo Bue, A.M. et al.: J. Chemother., 13, 255 (2002)
• Fera, M.T. et al.: Int. J. Antimicrob. Agents, 17, 151 (2002)