| Compound Information | SONAR Target prediction |
| Name: | Chloramphenicol |
| Unique Identifier: | LAT002D07 |
| MolClass: | Checkout models in ver1.5 and ver1.0 |
| Molecular Formula: | C11Cl2H12N2O5 |
| Molecular Weight: | 311.034 g/mol |
| X log p: | 8.564 (online calculus) |
| Lipinksi Failures | 1 |
| TPSA | 60.21 |
| Hydrogen Bond Donor Count: | 0 |
| Hydrogen Bond Acceptors Count: | 4 |
| Rotatable Bond Count: | 7 |
| Canonical Smiles: | [O-][N+](=O)c1ccc(cc1)C(O)C(CO)NC(=O)C(Cl)Cl |
| Generic_name: | Chloramphenicol |
| Chemical_iupac_name: | 2,2-dichloro-N-[1,3-dihydroxy-1-(4-nitrophenyl)-propan-2-yl]-acetamide |
| Drug_type: | Approved Drug |
| Pharmgkb_id: | PA448927 |
| Kegg_compound_id: | C00918 |
| Drugbank_id: | APRD00862 |
| Melting_point: | 150.5 oC |
| H2o_solubility: | 2500 mg/L (at 25 °C) |
| Logp: | 1.476 |
| Cas_registry_number: | 56-75-7 |
| Mass_spectrum: | http://webbook.nist.gov/cgi/cbook.cgi?Spec=C56757&Index=0&Type=Mass&Large=on |
| Drug_category: | Anti-Bacterial Agents; Protein Synthesis Inhibitors; ATC:D06AX02; ATC:D10AF03; ATC:G01AA05; ATC:J01BA01; ATC:S01AA01; ATC:S02AA01; ATC:S03AA08 |
| Indication: | Used in treatment of cholera, as it destroys the vibrios and decreases the diarrhea. It is effective against tetracycline-resistant vibrios. It is also used in eye drops or ointment to treat bacterial conjunctivitis. |
| Pharmacology: | Chloramphenicol is a broad-spectrum antibiotic that was derived from the bacterium Streptomyces venezuelae and is now produced synthetically. Chloramphenicol is effective against a wide variety of microorganisms, but due to serious side-effects (e.g., damage to the bone marrow, including aplastic anemia) in humans, it is usually reserved for the treatment of serious and life-threatening infections (e.g., typhoid fever). Chloramphenicol is bacteriostatic but may be bactericidal in high concentrations or when used against highly susceptible organisms. Chloramphenicol stops bacterial growth by binding to the bacterial ribosome (blocking peptidyl transferase) and inhibiting protein synthesis. |
| Mechanism_of_action: | Chloramphenicol is lipid-soluble, allowing it to diffuse through the bacterial cell membrane. It then reversibly binds to the 50S subunit of bacterial ribosomes where transfer of amino acids to growing peptide chains is prevented (perhaps by suppression of peptidyl transferase activity), thus inhibiting peptide bond formation and subsequent protein synthesis. |
| Organisms_affected: | Enteric bacteria and other eubacteria |
| Found: 5 nonactive as graph: single | with analogs | 1 2 3 4 5 Next >> |
| Species: | 4932 |
| Condition: | pdr18h |
| Replicates: | 2 |
| Raw OD Value: r im | 0.6133±0.00268701 |
| Normalized OD Score: sc h | 0.9707±0.00186281 |
| Z-Score: | -0.6896±0.108633 |
| p-Value: | 0.49171 |
| Z-Factor: | -1.98866 |
| Fitness Defect: | 0.7099 |
| Bioactivity Statement: | Nonactive |
| ps |
| DBLink | Rows returned: 7 | 1 2 Next >> |
| 298 | 2,2-dichloro-N-[1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide |
| 5959 | 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide |
| 92099 | 2,2-dichloro-N-[(1S,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide |
| 127517 | 2,2-dichloro-N-[(1R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide |
| 146033 | 2,2-dichloro-N-[(1R,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide |
| 146034 | 2,2-dichloro-N-[(1S,2R)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide |
| internal high similarity DBLink | Rows returned: 3 |
| JFD 01781 | 1.0000 |
| Prest51 | 1.0000 |
| SPE01500174 | 1.0000 |
| active | Cluster 681 | Additional Members: 8 | Rows returned: 0 |
Service provided by the
Mike Tyers Laboratory