apramycin   Click here for help

GtoPdb Ligand ID: 10760

Synonyms: EL-857 | EL857 | Nebramycin factor 2 | Nebramycin II
PDB Ligand
Compound class: Synthetic organic
Comment: Apramycin is a deoxystreptamine class antibiotic with Gram-negative activity [2-3].
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 16
Hydrogen bond donors 11
Rotatable bonds 6
Topological polar surface area 283.64
Molecular weight 539.28
XLogP -4.99
No. Lipinski's rules broken 2
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Canonical SMILES CN[C@@H]1[C@H](O[C@@H]2[C@@H]([C@@H]1O)O[C@@H]([C@@H](C2)N)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O)N)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)N
Isomeric SMILES CN[C@@H]1[C@H](O[C@@H]2[C@@H]([C@@H]1O)O[C@@H]([C@@H](C2)N)O[C@@H]1[C@@H](N)C[C@H]([C@@H]([C@H]1O)O)N)O[C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)N
InChI InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1
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Summary of Clinical Use Click here for help
Apramycin was progressed to clinical trial, but its development was discontinued.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04105205 First-In-Human Study of Apramycin Phase 1 Interventional Juvabis AG This first-in-human study is designed to evaluate the safety, tolerability and pharmacokinetics of apramycin in healthy volunteers. As of April 2020 is is noted as 'Active, not recruiting' on ClinicalTrials.gov.