Synonyms: AS-E 136 | Dynabac® | LY237216
dirithromycin is an approved drug (FDA (1995))
Comment: Dirithromycin is a 14-membered macrolide antibacterial compound [ 1]. It is an orally administered prodrug of the semi-synthetic erythromycin derivative erythromycyclamine.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors
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16
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Hydrogen bond donors
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5
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Rotatable bonds
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12
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Topological polar surface area
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196.33
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Molecular weight
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835.08
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XLogP
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1.56
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No. Lipinski's rules broken
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3
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Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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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]2[C@@H](C)[C@H]([C@H](C)C[C@](C)([C@@H]([C@@H](C)[C@@H]([C@@H](C)C(=O)O1)O[C@H]3C[C@](C)([C@H]([C@H](C)O3)O)OC)O[C@H]4[C@@H]([C@H](C[C@@H](C)O4)N(C)C)O)O)N[C@@H](COCCOC)O2)O
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Isomeric SMILES
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CC[C@@H]1[C@@]([C@H]2[C@H]([C@H]([C@@H](C[C@@]([C@@H]([C@H]([C@@H]([C@H](C(=O)O1)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)O)(C)OC)C)O[C@H]4[C@@H]([C@H](C[C@H](O4)C)N(C)C)O)(C)O)C)N[C@H](O2)COCCOC)C)(C)O
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InChI
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InChI=1S/C42H78N2O14/c1-15-29-42(10,49)37-24(4)32(43-30(56-37)21-52-17-16-50-13)22(2)19-40(8,48)36(58-39-33(45)28(44(11)12)18-23(3)53-39)25(5)34(26(6)38(47)55-29)57-31-20-41(9,51-14)35(46)27(7)54-31/h22-37,39,43,45-46,48-49H,15-21H2,1-14H3/t22-,23-,24+,25+,26-,27+,28+,29-,30-,31+,32+,33-,34+,35+,36-,37-,39+,40-,41-,42-/m1/s1
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InChI Key
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WLOHNSSYAXHWNR-DWIOZXRMSA-N
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Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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