From August 18th 2026, GtoPdb will require users to register to use the website. Please see our blog post for more information.

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: Natural product
Comment: Chloramphenicol is a broad-spectrum antibacterial originally isolated from the soil-dwelling actinomycete Streptomyces venequelae [2], but now produced commercially through total chemical synthesis. Its activity is primarily bacteriostatic.
Chloramphenicol is one of the access group antibacterials on the World Health Organization's Model List of Essential Medicines (link provided in the Classification table under the Summary tab).

chloramphenicol is commercially available from our sponsors

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

✖
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
InChI Key WIIZWVCIJKGZOK-RKDXNWHRSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Bioactivity Comments
MIC90 for antimicrobial activity against β-lactamase-negative, ampicillin-resistant Haemophilus influenzae is 1 μg/ml in vitro [1].
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
TAS2R8 Hs Agonist Agonist - - - 3
⤷ [3]
Description: Threshold=30 μM
TAS2R41 Hs Agonist Agonist - - - 4
⤷ [4]
Description: Threshold=300 μM