amikacin   Click here for help

GtoPdb Ligand ID: 10894

Synonyms: Amikin® | AMK | Arikayce liposomal® | BB-K8
Approved drug PDB Ligand
amikacin is an approved drug (FDA (1981), EMA (2020))
Compound class: Synthetic organic
Comment: Amikacin is a semi-synthetic aminoglycoside antibiotic that is active against a broad spectrum of Gram-negative organisms, including pseudomonas and some Gram-positive organisms (principally Staphylococcus aureus, including some methicillin-resistant strains). It is a kanamycin derivative. Functionally it binds to the bacterial 30S ribosomal subunit and disrupts protein synthesis, thereby creating its bactericidal effect.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 18
Hydrogen bond donors 13
Rotatable bonds 11
Topological polar surface area 331.94
Molecular weight 585.29
XLogP -6.56
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
Click here for help
Canonical SMILES NCC[C@@H](C(=O)N[C@@H]1C[C@H](N)[C@H]([C@@H]([C@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)N)O)O)O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1O)O)O)O
Isomeric SMILES NCC[C@@H](C(=O)N[C@@H]1C[C@H](N)[C@H]([C@@H]([C@H]1O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)N)O)O)O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1O)O)O)O
InChI InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1
InChI Key LKCWBDHBTVXHDL-RMDFUYIESA-N