Name: Apramycin (Nebramycin II)
Rating: 5 (10 reviews)

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HIT ID:HIT212038730
Cas No:37321-09-8
常用名:Apramycin (Nebramycin II)
IUPAC:(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)-octahydropyrano[3,2-b]pyran-2-yl]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol
IUPAC:(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)-octahydropyrano[3,2-b]pyran-2-yl]oxy}-5-amino-6-(hydroxymethyl)oxane-3,4-diol
InChI key:XZNUGFQTQHRASN-XQENGBIVSA-N

分子式:C21H41N5O11
分子量:539.583
氢键供体数 (HBD):11
氢键受体数 (HBA):16
LogP:-6.5081105
SMILES:[H][C@]1(O[C@H]2O[C@H](CO)[C@@H](N)[C@H](O)[C@H]2O)O[C@H]2C[C@@H](N)[C@@H](O[C@]3([H])[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)O[C@]2([H])[C@H](O)[C@@H]1NC
SMILES:[H][C@]1(O[C@H]2O[C@H](CO)[C@@H](N)[C@H](O)[C@H]2O)O[C@H]2C[C@@H](N)[C@@H](O[C@]3([H])[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)O[C@]2([H])[C@H](O)[C@@H]1NC

Apramycin(Nebramycin II) is an aminoglycoside antibiotic used in veterinary medicine.Target: Apramycin stands out among aminoglycosides for its mechanism of action which is based on blocking translocation and its ability to bind also to the eukaryotic decoding site despite differences in key residues required for apramycin recognition by the bacterial target. The drug binds in the deep groove of the RNA which forms a continuously stacked helix comprising non-canonical C.A and G.A base pairs and a bulged-out adenine. The binding mode of apramycin at the human decoding-site RNA is distinct from aminoglycoside recognition of the bacterial target, suggesting a molecular basis for the actions of apramycin in eukaryotes and bacteria.

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