HARIBOSS

Harnessing RIBOnucleic acid - Small molecules Structures

Compound CLM

Identifiers

  • Canonical SMILES: 
    OC[C@@H](NC(=O)C(Cl)Cl)[C@H](O)c1ccc(cc1)[N+]([O-])=O
  • IUPAC name: 
    2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide
  • InChi: 
    InChI=1S/C11H12Cl2N2O5/c12-10(13)11(18)14-8(5-16)9(17)6-1-3-7(4-2-6)15(19)20/h1-4,8-10,16-17H,5H2,(H,14,18)/t8-,9-/m1/s1
  • InChiKey: 
    WIIZWVCIJKGZOK-RKDXNWHRSA-N

Chemistry rules

Lipinski's RO5 Veber Pfizer's 3/75

External links

5959 CHEMBL130 DB00446

RNA-SM complexes

PDB code Deposition date Reference publication
1k01 Sept. 17, 2001 Schlünzen Frank, Zarivach Raz, Harms Jörg, Bashan Anat, Tocilj Ante, Albrecht Renate, Yonath Ada, Franceschi François. . Structural basis for the interaction of antibiotics with the peptidyl transferase centre in eubacteria Nature
1nji Dec. 31, 2002 Hansen Jeffrey L., Moore Peter B., Steitz Thomas A.. . Structures of Five Antibiotics Bound at the Peptidyl Transferase Center of the Large Ribosomal Subunit Journal of Molecular Biology
4v7t Aug. 14, 2010 Dunkle Jack A., Xiong Liqun, Mankin Alexander S., Cate Jamie H. D.. . Structures of the Escherichia coli ribosome with antibiotics bound near the peptidyl transferase center explain spectra of drug action Proceedings of the National Academy of Sciences
4v7w Aug. 16, 2010 Bulkley David, Innis C. Axel, Blaha Gregor, Steitz Thomas A.. . Revisiting the structures of several antibiotics bound to the bacterial ribosome Proceedings of the National Academy of Sciences
4v7w Aug. 16, 2010 Bulkley David, Innis C. Axel, Blaha Gregor, Steitz Thomas A.. . Revisiting the structures of several antibiotics bound to the bacterial ribosome Proceedings of the National Academy of Sciences
6nd5 Dec. 13, 2018 Svetlov Maxim S., Plessa Elena, Chen Chih-Wei, Bougas Anthony, Krokidis Marios G., Dinos George P., Polikanov Yury S.. . High-resolution crystal structures of ribosome-bound chloramphenicol and erythromycin provide the ultimate basis for their competition RNA
6nd5 Dec. 13, 2018 Svetlov Maxim S., Plessa Elena, Chen Chih-Wei, Bougas Anthony, Krokidis Marios G., Dinos George P., Polikanov Yury S.. . High-resolution crystal structures of ribosome-bound chloramphenicol and erythromycin provide the ultimate basis for their competition RNA
7ood May 27, 2021 Xue Liang, Lenz Swantje, Zimmermann-Kogadeeva Maria, Tegunov Dimitry, Cramer Patrick, Bork Peer, Rappsilber Juri, Mahamid Julia. . Visualizing translation dynamics at atomic detail inside a bacterial cell Nature
7p3k July 8, 2021 Su Ting, Kudva Renuka, Becker Thomas, Buschauer Robert, Komar Tobias, Berninghausen Otto, von Heijne Gunnar, Cheng Jingdong, Beckmann Roland. . Structural basis of l-tryptophan-dependent inhibition of release factor 2 by the TnaC arrest peptide Nucleic Acids Research
7phb Aug. 16, 2021 Xue Liang, Lenz Swantje, Zimmermann-Kogadeeva Maria, Tegunov Dimitry, Cramer Patrick, Bork Peer, Rappsilber Juri, Mahamid Julia. . Visualizing translation dynamics at atomic detail inside a bacterial cell Nature
7u2i Feb. 24, 2022 Syroegin Egor A, Aleksandrova Elena V, Polikanov Yury S. . Structural basis for the inability of chloramphenicol to inhibit peptide bond formation in the presence of A-site glycine Nucleic Acids Research
7u2i Feb. 24, 2022 Syroegin Egor A, Aleksandrova Elena V, Polikanov Yury S. . Structural basis for the inability of chloramphenicol to inhibit peptide bond formation in the presence of A-site glycine Nucleic Acids Research

Physicochemical filters

Descriptor Lipinski's RO5 Veber Pfizer's 3/75
Compliance
MW 322.01 g/mol
HBA 5
HBD 3
HBA + HBD
AlogP 0.91
TPSA 112.70
RB 6

Radar chart