josamycin   Click here for help

GtoPdb Ligand ID: 12924

Synonyms: kitasamycin A3 | leucomycin A3 | turimycin A5
Approved drug
josamycin is an approved drug
Compound class: Natural product
Comment: Josamycin is a 16-membered macrolide antibacterial compound that is identical to leucomycin A3 [2]. It is obtained from fermentation of the actinomycete Streptomyces narbonensis.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 3
Rotatable bonds 14
Topological polar surface area 206.05
Molecular weight 828
XLogP 2.95
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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Canonical SMILES CC(C)CC(=O)O[C@H]1[C@H](C)O[C@H](C[C@@]1(C)O)O[C@@H]2[C@@H](C)O[C@H]([C@@H]([C@H]2N(C)C)O)O[C@H]3[C@@H](CC=O)C[C@@H](C)[C@H](/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]3OC)OC(=O)C)O
Isomeric SMILES C[C@@H]1C/C=C/C=C/[C@@H]([C@@H](C[C@@H]([C@@H]([C@H]([C@@H](CC(=O)O1)OC(=O)C)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)C)O[C@H]3C[C@@]([C@H]([C@@H](O3)C)OC(=O)CC(C)C)(C)O)N(C)C)O)CC=O)C)O
InChI InChI=1S/C42H69NO15/c1-23(2)19-32(47)56-40-27(6)53-34(22-42(40,8)50)57-37-26(5)54-41(36(49)35(37)43(9)10)58-38-29(17-18-44)20-24(3)30(46)16-14-12-13-15-25(4)52-33(48)21-31(39(38)51-11)55-28(7)45/h12-14,16,18,23-27,29-31,34-41,46,49-50H,15,17,19-22H2,1-11H3/b13-12+,16-14+/t24-,25-,26-,27+,29+,30+,31-,34+,35-,36-,37-,38+,39+,40+,41+,42-/m1/s1
InChI Key XJSFLOJWULLJQS-NGVXBBESSA-N