Synonyms: (8S)-8-fluoroerythromycin A | P-0501A
flurithromycin is an approved drug
Comment: Flurithromycin is a 14-membered macrolide antibacterial compound, originally isolated from Streptomyces erythraeus using a mutational biosynthesis approach [ 4]. It is a fluorinated derivative of erythromycin with improved acid stability.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors
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14
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Hydrogen bond donors
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5
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Rotatable bonds
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7
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Topological polar surface area
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193.91
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Molecular weight
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751.92
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XLogP
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1.19
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No. Lipinski's rules broken
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2
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SMILES / InChI / InChIKey
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Canonical SMILES
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CC[C@@H]1[C@](C)([C@@H]([C@@H](C)C(=O)[C@](C)(C[C@](C)([C@@H]([C@@H](C)[C@@H]([C@@H](C)C(=O)O1)O[C@H]2C[C@](C)([C@H]([C@H](C)O2)O)OC)O[C@H]3[C@@H]([C@H](C[C@@H](C)O3)N(C)C)O)O)F)O)O
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Isomeric SMILES
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CC[C@@H]1[C@@]([C@@H]([C@H](C(=O)[C@@](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]2C[C@@]([C@H]([C@@H](O2)C)O)(C)OC)C)O[C@H]3[C@@H]([C@H](C[C@H](O3)C)N(C)C)O)(C)O)(C)F)C)O)(C)O
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InChI
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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
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InChI Key
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XOEUHCONYHZURQ-HNUBZJOYSA-N
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