chloramphenicol   Click here for help

GtoPdb Ligand ID: 10901

Synonyms: Brolene® | chloromycetin
Approved drug PDB Ligand
chloramphenicol is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: Chloramphenicol is a semisynthetic, broad-spectrum antibacterial derived from Streptomyces venequelae. Its activity is primarily bacteriostatic.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 7
Topological polar surface area 112.7
Molecular weight 322.01
XLogP 0.69
No. Lipinski's rules broken 0
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Canonical SMILES OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
Isomeric SMILES OC[C@H]([C@@H](c1ccc(cc1)[N+](=O)[O-])O)NC(=O)C(Cl)Cl
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
1. Bae S, Lee J, Lee J, Kim E, Lee S, Yu J, Kang Y. (2010)
Antimicrobial resistance in Haemophilus influenzae respiratory tract isolates in Korea: results of a nationwide acute respiratory infections surveillance.
Antimicrob Agents Chemother, 54 (1): 65-71. [PMID:19884366]
2. Meyerhof W, Batram C, Kuhn C, Brockhoff A, Chudoba E, Bufe B, Appendino G, Behrens M. (2010)
The molecular receptive ranges of human TAS2R bitter taste receptors.
Chem Senses, 35 (2): 157-70. [PMID:20022913]
3. Thalmann S, Behrens M, Meyerhof W. (2013)
Major haplotypes of the human bitter taste receptor TAS2R41 encode functional receptors for chloramphenicol.
Biochem Biophys Res Commun, 435 (2): 267-73. [PMID:23632330]