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
SMILES / InChI / InChIKey
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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
InChI Key XZNUGFQTQHRASN-XQENGBIVSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(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
International Nonproprietary Names Click here for help
INN number INN
3185 apramycin
Synonyms Click here for help
EL-857 | EL857 | Nebramycin factor 2 | Nebramycin II
Database Links Click here for help
Specialist databases
Antibiotic DB Antibiotic DB Database logo 1287
Other databases
CAS Registry No. 37321-09-8 (source: WHO INN record)
ChEMBL Ligand CHEMBL1230961
GtoPdb PubChem SID 405560201
PubChem CID 3081545
RCSB PDB Ligand AM2
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