CHLORAMPHENICOL

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC D06AX02 D10AF03 G01AA05 J01BA01 S01AA01 S02AA01 S03AA08
UNII 66974FR9Q1
EPA CompTox DTXSID7020265

Structure

InChI Key WIIZWVCIJKGZOK-RKDXNWHRSA-N
Smiles O=C(N[C@H](CO)[C@H](O)c1ccc([N+](=O)[O-])cc1)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

Physicochemical Descriptors

Property Name Value
Molecular Formula C11H12Cl2N2O5
Molecular Weight 323.13
AlogP 0.91
Hydrogen Bond Acceptor 5.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 6.0
Polar Surface Area 112.7
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 20.0

Bioactivity

Mechanism of Action Action Reference
Bacterial 70S ribosome inhibitor INHIBITOR PubMed PubMed Wikipedia
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Ligase
7900 - - - -
Other cytosolic protein
- 430 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 85
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - - 1
Unclassified protein
- 430 - - -
Assay Description Organism Bioactivity Reference
Tested for inhibition of puromycin reaction and reported as equilibrium constant derived from primary and secondary kinetic plots for the inhibition of peptide bond formation Escherichia coli 700.0 nM
Inhibitory concentration of compound was determined against Escherichia coli in the absence of alkynyl amino acid 1 Escherichia coli 5.0 ug.mL-1
Inhibitory concentration of compound was determined against Escherichia coli in the presence of alkynyl amino acid 1 Escherichia coli 100.0 ug.mL-1
inhibition of Bacillus cereus was measured by zone diameter Bacillus cereus 8.0 mm
Zone of inhibition of Escherichia coli after treatment with the 30 ug of the compound Escherichia coli 15.0 mm
Zone of inhibition of Staphylococcus aureus after treatment with the 30 ug of the compound Staphylococcus aureus 0.0 mm
Zone of inhibition of Pseudomonas aeruginosa after treatment with the 30 ug of the compound Pseudomonas aeruginosa 0.0 mm
Antiproliferative effect against primary human osteoblasts assessed as BrdU incorporation into DNA after 48 hrs Homo sapiens 230.0 ug.mL-1
Inhibition of metabolic activity in primary human osteoblasts assessed as MTT reduction after 48 hrs Homo sapiens 400.0 ug.mL-1
Antiproliferative effect against MG63 cells assessed as BrdU incorporation into DNA after 48 hrs after 48 hrs Homo sapiens 400.0 ug.mL-1
Inhibition of metabolic activity in MG63 cells assessed as MTT reduction after 48 hrs Homo sapiens 400.0 ug.mL-1
Antiproliferative effect against HeLa cells after 48 hrs Homo sapiens 400.0 ug.mL-1
Inhibition of metabolic activity in HeLa cells assessed as MTT reduction after 48 hrs Homo sapiens 340.0 ug.mL-1
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens 1.4 %
Inhibition of type II fatty acid synthesis in Staphylococcus aureus using n-octanoyl-CoA and [14C]malonyl CoA substrate Staphylococcus aureus 250.0 ug.mL-1
Displacement of [3H]chloramphenicol from 70S ribosomal complex in Staphylococcus aureus ATCC 29213 by competitive binding assay Staphylococcus aureus 430.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Inhibitors of Streptokinase Promotor Activity. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)] Streptococcus pyogenes M1 GAS 973.0 nM
Inhibition of ribosomal subunit assembly in Escherichia coli assessed as reduction in mature 23S rRNA at 7 ug/ml Escherichia coli 50.0 %
Inhibition of ribosomal subunit assembly in Escherichia coli assessed as reduction in mature 23S rRNA at 100 ug/ml in presence of E-peptide Escherichia coli 50.0 %
Antimalarial activity against trophozoite stage of chloroquine-sensitive Plasmodium falciparum 3D7 infected in human erythrocytes after 48 hrs Plasmodium falciparum 0.02 ug.mL-1
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 84.74 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 90.58 %
Inhibition of protein synthesis in Mycobacterium bovis BCG assessed as inhibition of [3H]leucine incorporation by liquid scintillation counting Mycobacterium bovis BCG 5.6 ug.mL-1
Cytotoxicity against mouse HII4E cells after 24 hrs by MTT cell viability assay Mus musculus 143.0 ug.mL-1
Antibacterial activity against Staphylococcus aureus ATCC 25923 assessed as growth inhibition after 24 hrs by microdilution method Staphylococcus aureus 430.0 nM
Inhibition of Escherichia coli K-12 70S ribosome poly(U)-programmed ribosome (complex C) bearing tRNAPhe at E-site and Ac[3H]Phe-tRNA at P-site assessed as reduction in peptide bond formation using puromycin(S) substrate Escherichia coli K-12 880.0 nM
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging Homo sapiens -3.94 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 22.7 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.65 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus 0.65 %

Related Entries

Environmental Exposure

Environmental Exposure Map
Countries
Romania

Cross References

Resources Reference
ChEBI 17698
ChEMBL CHEMBL130
DrugBank DB00446
DrugCentral 589
FDA SRS 66974FR9Q1
Human Metabolome Database HMDB0014589
Guide to Pharmacology 10901
KEGG C00918
PDB CLM
PubChem 5959
SureChEMBL SCHEMBL16111
ZINC ZINC000000113382
CONTENTS