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
Bioactivity Comments
MIC90 for antimicrobial activity against β-lactamase-negative, ampicillin-resistant Haemophilus influenzae is 1 μg/ml in vitro [1].
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TAS2R8 Hs Agonist Agonist - - - 2
Description: Threshold=30 μM
TAS2R41 Hs Agonist Agonist - - - 3
Description: Threshold=300 μM