contezolid   Click here for help

GtoPdb Ligand ID: 10795

Synonyms: MRX-1 | MRX-I
PDB Ligand
Compound class: Synthetic organic
Comment: Contezolid is an oxazolidinone antibiotic against Gram-positive pathogens [1], including methicillin-resistant Staphylococcus aureus (MRSA), penicillin-resistant Streptococcus pneumoniae, penicillin-intermediate S. pneumoniae (PISP), and vancomycin-resistant enterococci (VRE). Its orally delivered prodrug is contezolid acefosamil (parent) (MRX-4). Contezolid targets protein synthesis by binding to the V region of the bacterial 23S rRNA.
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 87.91
Molecular weight 408.1
XLogP 2.44
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES O=C1CCN(C=C1)c1c(F)cc(c(c1F)F)N1C[C@@H](OC1=O)CNc1ccon1
Isomeric SMILES O=C1CCN(C=C1)c1c(F)cc(c(c1F)F)N1C[C@@H](OC1=O)CNc1ccon1
InChI InChI=1S/C18H15F3N4O4/c19-12-7-13(15(20)16(21)17(12)24-4-1-10(26)2-5-24)25-9-11(29-18(25)27)8-22-14-3-6-28-23-14/h1,3-4,6-7,11H,2,5,8-9H2,(H,22,23)/t11-/m0/s1
InChI Key SULYVXZZUMRQAX-NSHDSACASA-N
References
1. Li CR, Zhai QQ, Wang XK, Hu XX, Li GQ, Zhang WX, Pang J, Lu X, Yuan H, Gordeev MF et al.. (2014)
In vivo antibacterial activity of MRX-I, a new oxazolidinone.
Antimicrob Agents Chemother, 58 (4): 2418-21. [PMID:24395231]