josamycin   Click here for help

GtoPdb Ligand ID: 12924

Synonyms: kitasamycin A3 | leucomycin A3 | turimycin A5
Approved drug
josamycin is an approved drug
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
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes
IUPAC Name Click here for help
[(2S,3S,4R,6S)-6-[(2R,3S,4R,5R,6S)-6-[[(4R,5S,6S,7R,9R,10R,11E,13E,16R)-4-acetyloxy-10-hydroxy-5-methoxy-9,16-dimethyl-2-oxo-7-(2-oxoethyl)-1-oxacyclohexadeca-11,13-dien-6-yl]oxy]-4-dimethylamino-5-hydroxy-2-methyloxan-3-yl]oxy-4-hydroxy-2,4-dimethyloxan-3-yl] 3-methylbutanoate
International Nonproprietary Names Click here for help
INN number INN
2837 josamycin
Synonyms Click here for help
kitasamycin A3 | leucomycin A3 | turimycin A5
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo
Other databases
CAS Registry No. 16846-24-5 (source: Scifinder)
ChEBI CHEBI:31739
ChEMBL Ligand CHEMBL224436
DrugBank Ligand DB01321
DrugCentral Ligand 1518
GtoPdb PubChem SID 485206045
PubChem CID 5282165
Search Google for chemical match using the InChIKey XJSFLOJWULLJQS-NGVXBBESSA-N
Search Google for chemicals with the same backbone XJSFLOJWULLJQS
Search PubMed clinical trials josamycin
Search PubMed titles josamycin
Search PubMed titles/abstracts josamycin
UniChem Compound Search for chemical match using the InChIKey XJSFLOJWULLJQS-NGVXBBESSA-N
UniChem Connectivity Search for chemical match using the InChIKey XJSFLOJWULLJQS-NGVXBBESSA-N