Compound ID | 2489
Synonym(s): Pseudomonic acid
Class: Aminoacyl-tRNA synthetase inhibitor (isoleucyl-tRNA synthetase [Ile-RS] inhibitor)
Spectrum of activity: | Gram-positive |
Details of activity: | Active against Staphylococcus aureus, Staphylococcus epidermidis, and Streptococcus pyogenes |
Propensity to select resistant mutants: | Yes |
Description: | Natural product from Pseudomonas fluorescens; used topically but not systemically (compound is rapidly hydrolysed to inactive metabolites in the latter case) |
Year first mentioned: | 1971 |
Highest developmental phase: | Approved for topical use by FDA in 1997 |
Development status: | Approved |
Chemical structure(s): | |
Canonical SMILES: | C/C(=C\C(=O)OCCCCCCCCC(=O)O)/C[C@H]1[C@@H]([C@@H]([C@@H](C[C@H]2[C@H]([C@@H](C)[C@H](C)O)O2)CO1)O)O |
Isomeric SMILES: | C[C@H]([C@H]1[C@@H](O1)C[C@H]2CO[C@H]([C@@H]([C@@H]2O)O)C/C(=C/C(=O)OCCCCCCCCC(=O)O)/C)[C@H](C)O |
InChI: | InChI=1S/C26H44O9/c1-16(13-23(30)33-11-9-7-5-4-6-8-10-22(28)29)12-20-25(32)24(31)19(15-34-20)14-21-26(35-21)17(2)18(3)27/h13,17-21,24-27,31-32H,4-12,14-15H2,1-3H3,(H,28,29)/b16-13+/t17-,18-,19-,20-,21-,24+,25-,26-/m0/s1 |
InChI Key: | MINDHVHHQZYEEK-HBBNESRFSA-N |
Structure link: | https://pubchem.ncbi.nlm.nih.gov/compound/446596 |
External links: | |
Guide to Pharmacology: | mupirocin |
Main Source: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1162199/ |
Patent: | US6013657A |