Compound ID | 611

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CHIR-090

Class: Small molecule antibacterial agent

Agent Type: Synthetic; Small molecule; Direct acting;
Spectrum of activity: Gram-negative
Mechanism of action: Lipopolysaccharide synthesis inhibitor. LpxC inhibitor
Target Pathogen: Active against Pseudomonas aeruginosa, Neisseria meningitis, and Helicobacter pylori
Description: Synthetic compound with N-aroyl-L-threonine hydroxamic acid scaffold
Institute where first reported: Novartis Inst. for BioMed. Res., Inc, USA
Year first mentioned: 2010
Development status: Experimental
Reason dropped: CHIR 090's was discontinued due to problems with developing resistance
Chemical structure(s):
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Molecular weight: 437.49
Iso. SMILES: C[C@H]([C@@H](C(=O)NO)NC(=O)C1=CC=C(C=C1)C#CC2=CC=C(C=C2)CN3CCOCC3)O
InChI Key: FQYBTYFKOHPWQT-VGSWGCGISA-N
Can. SMILES: C[C@H]([C@@H](C(=O)NO)NC(=O)C1=CC=C(C#CC2=CC=C(C=C2)CN3CCOCC3)C=C1)O
InChI: InChI=1S/C24H27N3O5/c1-17(28)22(24(30)26-31)25-23(29)21-10-8-19(9-11-21)3-2-18-4-6-20(7-5-18)16-27-12-14-32-15-13-27/h4-11,17,22,28,31H,12-16H2,1H3,(H,25,29)(H,26,30)/t17-,22+/m1/s1
External links:
PubChem link: https://pubchem.ncbi.nlm.nih.gov/compound/11546620
Citations:
  • https://www.nature.com/articles/ja201349.pdf
  • https://doi.org/10.1021/bi6025165
  • https://doi.org/10.1021/bi0518186

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