Structure via PubChem · Public domain (PubChem)
آپرامایسین
Sign in to saveAlso known as nebramycin factor 2, nebramycin II, 4-O-((8R)-2-amino-8-O-(4-amino-4-deoxy-alpha-D-glucopyranosyl)-2,3,7-trideoxy-7-(methylamino)-D-glycero-alpha-D-allo-octodialdo-1,5:8,4-dipyranos-1-yl)-2-deoxy-D-streptamine, 4-O-(3alpha-amino-6alpha-((4-amino-4-deoxy-alpha-D-glucopyranosyl)oxy)-2,3,4,5abeta,6,7,8,8aalpha-octahydro-8beta-hydroxy-7beta-(methylamino)pyrano(3,2-b)pyran-2alpha-yl)-2-deoxy-D-streptamine, Nebramycin II, Apramycin
Apramycin (nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine. It is produced by Streptomyces tenebrarius.
Chemical data
- Formula
- C21H41N5O11
- Molecular weight
- 539.6 g/mol
- IUPAC name
- (2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4aR,6S,7R,8aS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4a,6,7,8,8a-octahydropyrano[3,2-b]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol
- SMILES
- CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O
- InChIKey
- XZNUGFQTQHRASN-XQENGBIVSA-N
- XLogP
- -7
- Polar surface area
- 284 Ų
- H-bond donors
- 11
- H-bond acceptors
- 16
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
492 papers- Apramycin has high in vitro activity against Mycobacterium tuberculosis.Journal of medical microbiology · 2024
- Apramycin resistance in epidemic carbapenem-resistant Klebsiella pneumoniae ST258 strains.The Journal of antimicrobial chemotherapy · 2021
- Apramycin Overcomes the Inherent Lack of Antimicrobial Bactericidal Activity in Mycobacterium abscessus.Antimicrobial agents and chemotherapy · 2022
- In vitro activity of apramycin against 16S-RMTase-producing Gram-negative isolates.Journal of global antimicrobial resistance · 2023
- Pharmacodynamic assessment of apramycin against Mycobacterium abscessus in a hollow fibre infection model.The Journal of antimicrobial chemotherapy · 2025
via PubMed
Wikidata facts
- Mass
- 539.28
Show 6 more facts
- chemical formula
- C₂₁H₄₁N₅O₁₁
- World Health Organisation international non-proprietary name
- apramycin
- isomeric SMILES
- CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O
- canonical SMILES
- CNC1C(C2C(CC(C(O2)OC3C(CC(C(C3O)O)N)N)N)OC1OC4C(C(C(C(O4)CO)N)O)O)O
- subject has role
- bactericide
- found in taxon
- Streptomyces
Sources (2)
via Wikidata · CC0