Josamycin

Synonym(s): Leucomycin A3  |  turimycin A5  |  kitasamycin A3

Class: Macrolide (16-membered macrolide)

Spectrum of activity:	Gram-positive
Details of activity:	Binds to the peptidyl transferase component of the 50S subunit of ribosomes, thus inhibiting peptide bond formation and bacterial protein synthesis. It is active against Gram-positive bacteria.
Description:	Natural product produced by Streptomyces.
Year first mentioned:	1964
Development status:	Approved, off-patent, not available in many countries

Chemical structure(s):
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
Structure link:	https://pubchem.ncbi.nlm.nih.gov/compound/5282165

External links:
Guide to Pharmacology:	josamycin
Main Source:	https://pubmed.ncbi.nlm.nih.gov/1506329/