Compound ID | 2288

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N-benzyl–substituted 3′-(R)-3′-aminomethyl-3′-hydroxy spectinomycin 1

Synonym(s): amSPC 1

Class: Aminoglycoside

Spectrum of activity: Gram-positive  &  Gram-negative
Details of activity: Active against Streptococcus pneumoniae, Streptococcus pyogenes, Listeria monocytogenes, Neisseria gonorrhoeae, Neisseria meningitidis, Haemophilus influenzae , and Legionella pneumophila; protein synthesis inhibitor
Description: Synthetic compound based on 3'-aminomethyl-3'-hydroxy spectinomycin, R-isomers have activity; N-benzyl–substituted 3′-(R)-3′-aminomethyl-3′-hydroxy spectinomycin; fluorine substitution to the para position of the phenyl ring; no mammalian toxicity observed in Vero cells and non-haemolytic at >100 ug/ml; 80% of mice survivability from Streptococcus pneumoniae infection in mice
Year first mentioned: 2015
Development status: Experimental
Chemical structure(s):
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Molecular weight: 471.52
Iso. SMILES: FC1=CC=C(CNC[C@@]2([C@]3(O[C@H]4[C@@H]([C@@H]([C@@H]([C@H]([C@@H]4O[C@]3(O[C@H](C2)C)[H])O)NC)O)NC)O)O)C=C1
InChI Key: XCLCDNAVWHNZSQ-JVIMCCEPSA-N
Can. SMILES: C[C@H]1C[C@](CNCC2=CC=C(C=C2)F)([C@@]3([C@]([H])(O1)O[C@H]4[C@@H]([C@H]([C@H]([C@H]([C@@H]4O3)NC)O)NC)O)O)O
InChI: InChI=1S/C22H34FN3O7/c1-11-8-21(29,10-26-9-12-4-6-13(23)7-5-12)22(30)20(31-11)32-19-17(28)14(24-2)16(27)15(25-3)18(19)33-22/h4-7,11,14-20,24-30H,8-10H2,1-3H3/t11-,14-,15+,16+,17+,18-,19-,20+,21-,22-/m0/s1
External links:
Citation: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4641453/
Patent: US10266544B2

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