TRICLOSAN

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Synonyms
Status
Molecule Category Free-form
ATC D08AE04 D09AA06
UNII 4NM5039Y5X
EPA CompTox DTXSID5032498

Structure

InChI Key XEFQLINVKFYRCS-UHFFFAOYSA-N
Smiles Oc1cc(Cl)ccc1Oc1ccc(Cl)cc1Cl
InChI
InChI=1S/C12H7Cl3O2/c13-7-1-3-11(9(15)5-7)17-12-4-2-8(14)6-10(12)16/h1-6,16H

Physicochemical Descriptors

Property Name Value
Molecular Formula C12H7Cl3O2
Molecular Weight 289.55
AlogP 5.14
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 2.0
Polar Surface Area 29.46
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 17.0

Bioactivity

Mechanism of Action Action Reference
Bacterial enoyl-[acyl-carrier-protein] reductase inhibitor INHIBITOR PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 200-10000 - 200-220 37
Enzyme
- 66-200 - 0-660 98-98
Secreted protein
- 53500 - - 62
Unclassified protein
- 100000 - - -
Assay Description Organism Bioactivity Reference
Evaluated for inhibition of enoyl acyl carrier protein reductase (FabI) in Escherichia coli. Escherichia coli 430.0 nM
Antibacterial activity against Escherichia coli FabI Escherichia coli 430.0 nM
Inhibitory activity against Enoyl-ACP reductase FabI in Escherichia coli Escherichia coli 430.0 nM
Inhibitory activity against Enoyl-ACP reductase FabI in Staphylococcus aureus Staphylococcus aureus 70.0 nM
Concentration required for the 50% inhibition of enoyl-ACP reductase from Staphylococcus aureus was determined. None 70.0 nM
Inhibition of PfENR enzymatic activity Plasmodium falciparum 73.0 nM
Inhibition of Plasmodium falciparum ENR enzymatic activity Plasmodium falciparum 73.0 nM
Inhibition of Plasmodium falciparum ENR by fluorescence quenching in presence of EGCG Plasmodium falciparum 7.29 nM
Inhibition of Plasmodium falciparum ENR by fluorescence quenching in presence of ECG Plasmodium falciparum 28.31 nM
Inhibition of Plasmodium falciparum ENR by fluorescence quenching in presence of EGC Plasmodium falciparum 52.71 nM
Inhibition of Plasmodium falciparum ENR by fluorescence quenching in presence of quercetin Plasmodium falciparum 30.54 nM
Inhibition of Plasmodium falciparum ENR by fluorescence quenching in presence of butein Plasmodium falciparum 71.02 nM
Inhibition of Plasmodium falciparum ENR in presence of EGCG by dilution assay Plasmodium falciparum 0.0019 nM
Inhibition of Plasmodium falciparum ENR in presence of EGC by dilution assay Plasmodium falciparum 0.109 nM
Inhibition of Plasmodium falciparum ENR in presence of ECG by dilution assay Plasmodium falciparum 0.05206 nM
Inhibition of Plasmodium falciparum ENR in presence of quercetin by dilution assay Plasmodium falciparum 0.2806 nM
Inhibition of Plasmodium falciparum ENR in presence of butein by dilution assay Plasmodium falciparum 0.7983 nM
Inhibition of Plasmodium falciparum ENR in presence of EGCG Plasmodium falciparum 1.0 nM
Inhibition of Plasmodium falciparum ENR in presence of EGC Plasmodium falciparum 8.25 nM
Inhibition of Plasmodium falciparum ENR in presence of ECG Plasmodium falciparum 8.0 nM
Inhibition of Plasmodium falciparum ENR in presence of quercetin Plasmodium falciparum 10.0 nM
Inhibition of Plasmodium falciparum ENR in presence of butein Plasmodium falciparum 13.72 nM
Inhibition of Escherichia coli DH5-alpha His tagged Fab1 Escherichia coli 510.0 nM
Effect on Streptococcus mutans LMG 14558 assessed as inhibition of biofilm formation in modified Robbin's device at 5 ug/ml relative to BHIS control Streptococcus mutans 78.13 %
Effect on Streptococcus mutans LMG 14558 assessed as inhibition of biofilm formation in modified Robbin's device at 1333 ug/ml relative to BHIS control Streptococcus mutans 10.9 %
Inhibition of Plasmodium falciparum recombinant enoyl ACP reductase expressed in BL21 (DE3) cells Plasmodium falciparum 66.0 nM
Inhibition of Plasmodium falciparum recombinant enoyl ACP reductase expressed in BL21 (DE3) cells with respect to crotonyl CoA Plasmodium falciparum 660.0 nM
Inhibition of Escherichia coli FabI Escherichia coli 900.0 nM
Inhibition of Escherichia coli enoyl-ACP reductase FabI Escherichia coli 900.0 nM
Inhibition of transthyretin fibril formation assessed as turbidity at 21.6 uM at pH 4.4 after 3 hrs None 62.0 %
Inhibition of Plasmodium falciparum FabI Plasmodium falciparum 0.014 ug.mL-1
Inhibition of Mycobacterium tuberculosis H37RV InhA Mycobacterium tuberculosis 200.0 nM
Inhibition of Plasmodium falciparum ENR Plasmodium falciparum 73.0 nM
Inhibition of Bacillus anthracis Enoyl ACP reductase Bacillus anthracis 500.0 nM
Binding affinity to human recombinant carbonyl reductase 1 expressed in Escherichia coli assessed as NADPH oxidation using isatin as substrate Homo sapiens 400.0 nM Binding affinity to human recombinant carbonyl reductase 1 expressed in Escherichia coli assessed as NADPH oxidation using isatin as substrate Homo sapiens 60.0 nM
Antimalarial activity after 48 hrs against Plasmodium falciparum 7G8 by [3H]hypoxanthine uptake Plasmodium falciparum 773.9 nM
Antimalarial activity after 96hrs against Plasmodium falciparum 7G8 by [3H]hypoxanthine uptake Plasmodium falciparum 424.4 nM
Inhibition of Plasmodium falciparum recombinant FabI Plasmodium falciparum 70.0 nM
Antiparasitic activity against Plasmodium falciparum in RBCs Plasmodium falciparum 700.0 nM
Inhibition of Plasmodium falciparum recombinant FabI A217V mutant Plasmodium falciparum 232.0 nM
Antibacterial activity against wild type Escherichia coli K12 after 12 hrs by microdilution method Escherichia coli 750.0 nM
Inhibition of Plasmodium falciparum enoyl-acyl carrier protein reductase Plasmodium falciparum 73.0 nM
Inhibition of Plasmodium falciparum enoyl-acyl carrier protein reductase expressed in Escherichia coli BL21(DE3) by spectrophotometry Plasmodium falciparum 50.0 nM
Inhibition of Pseudomonas aeruginosa PA0170 fabV assessed as reduction of Enoyl-[acyl-carrier-protein] reductase activity at 15 ug/ml Pseudomonas aeruginosa 15.0 %
Inhibition of wild type Pseudomonas aeruginosa ENR at 15 ug/ml Pseudomonas aeruginosa 29.0 %
Inhibition of Toxoplasma gondii enoyl reductase Toxoplasma gondii 20.0 nM
Inhibition of Plasmodium falciparum FabI by spectrophotometric analysis Plasmodium falciparum 0.014 ug.mL-1
PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhimurium using a modified counterscreen. (Class of assay: confirmatory) [Related pubchem assays: 2253, 1863, 1874 ] None 680.0 nM
PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibitors of the PhoP region in Salmonella Typhimurium. (Class of assay: confirmatory) [Related pubchem assays: 2253, 1863, 1981, 1874 ] None 490.0 nM
PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in Salmonella Typhimurium. (Class of assay: confirmatory) [Related pubchem assays: 2253, 1981, 1874 ] None 820.0 nM
PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of the PhoP region in Salmonella typhi. (Class of assay: confirmatory) [Related pubchem assays: 1850, 1864, 2252, 1985 ] None 550.0 nM
PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in Salmonella typhi. (Class of assay: confirmatory) [Related pubchem assays: 1864, 2252, 1985 ] None 670.0 nM
PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi using a modified counterscreen. (Class of assay: confirmatory) None 369.0 nM
Antiproliferative activity against Theileria parva-induced proliferation of bovine BL3 cells assessed as inhibition of [3H]thymidine uptake after 32 hrs Bos taurus 75.0 %
Induction of toxin TSST-1 production in Staphylococcus aureus FRI-1187 at 0.50 mM after 24 hrs relative to control Staphylococcus aureus 3.7 %
Induction of toxin TSST-1 production in Staphylococcus aureus FRI-1187 at 0.05 mM after 24 hrs relative to control Staphylococcus aureus 9.9 %
Inhibition of Plasmodium falciparum Enoyl-ACP reductase using crotonyl-CoA as substrate peincubated for 5 mins measured after 10 mins of substrate addition by UV-vis spectrophotometry Plasmodium falciparum 200.0 nM
Inhibition of Plasmodium falciparum Enoyl-ACP reductase using crotonyl-CoA as substrate at 0.05 mM peincubated for 5 mins measured after 10 mins of substrate addition by UV-vis spectrophotometry Plasmodium falciparum 99.5 %
Inhibition of Mycobacterium tuberculosis InhA expressed in Escherichia coli BL21 using trans-2-dodecenoyl-Coenzyme A as substrate at 10 uM by spectrophotometry Mycobacterium tuberculosis 99.0 %
Inhibition of Mycobacterium tuberculosis InhA using 2-trans-decenoyl-CoA as substrate at 10 uM after 5 mins using by spectrophotometry Mycobacterium tuberculosis 37.0 %
Inhibition of Plasmodium falciparum enoyl-ACP reductase assessed as oxidation of NADH to NAD+ after 10 mins by spectrophotometric analysis Plasmodium falciparum 70.0 nM
Inhibition of Staphylococcus aureus recombinant FabI using trans-2-octenoyl N-acetylcysteamine thioester as substrate preincubated for 60 mins Staphylococcus aureus 59.0 nM
Inhibition of Escherichia coli FabI using crotonoyl-CoA as substrate preincubated for 90 mins Escherichia coli 170.0 nM
Leishmanicidal activity against axenic amastigote stage of Leishmania panamensis MHOM/CO/87/UA140epir GFP assessed as parasite viability after 72 hr by MTT assay Leishmania panamensis 11.3 ug.mL-1
Inhibition of Toxoplasma gondii enoyl reductase assessed as conversion of trans-2-acyl-ACP to acyl-ACP Toxoplasma gondii 15.0 nM
Inhibition of Toxoplasma gondii enoyl reductase assessed as conversion of trans-2-acyl-ACP to acyl-ACP at 1 uM Toxoplasma gondii 98.0 %
Inhibition of Escherichia coli FabI using 2-dodecenoyl-CoA as substrate at pH 8 Escherichia coli 5.0 nM
Inhibition of Staphylococcus aureus FabI using dodecenoyl ACP at pH 7.8 Staphylococcus aureus 25.0 nM
Inhibition of Plasmodium falciparum FabI using crotonoyl-CoA as substrate preincubated for 10 mins prior to substrate addition Plasmodium falciparum 50.0 nM
Inhibition of Toxoplasma gondii enoyl acyl-carrier protein reductase Toxoplasma gondii 15.0 nM
Inhibition of Toxoplasma gondii enoyl acyl-carrier protein reductase at 1 uM Toxoplasma gondii 98.0 %
Inhibition of Francisella tularensis SCHU S4 FabI R96M mutant using CrCoA as substrate by UV-vis spectrophotometric analysis in presence of non pre-equilibrated NAD+ Francisella tularensis subsp. tularensis SCHU S4 300.0 nM
Inhibition of Francisella tularensis SCHU S4 FabI R96G mutant using CrCoA as substrate by UV-vis spectrophotometric analysis in presence of non pre-equilibrated NAD+ Francisella tularensis subsp. tularensis SCHU S4 50.0 nM
Inhibition of Plasmodium falciparum FabI using crotonoyl-CoA as substrate by UV-Vis spectrophotometric analysis in presence of NADH Plasmodium falciparum 50.0 nM
Inhibition of recombinant Plasmodium falciparum FabI using crotonoyl-CoA as substrate assessed as consumption of NADH after 10 mins Plasmodium falciparum 50.0 nM
Inhibition of wild type Mycobacterium tuberculosis inhA Mycobacterium tuberculosis 200.0 nM
Inhibition of Mycobacterium tuberculosis recombinant His6x-tagged InhA expressed in Escherichia coli BL21 at 50 uM Mycobacterium tuberculosis 99.0 %
Inhibition of Mycobacterium tuberculosis InhA using dodecyl coA as substrate by LC-MS/MS analysis Mycobacterium tuberculosis 630.0 nM
Inhibition of Plasmodium falciparum FabI Plasmodium falciparum 0.015 ug.mL-1
Inhibition of Staphylococcus aureus FabI assessed as reduction in inhibition of reduction of trans-2-octenoyl N-acetylcysteamine substrate by spectrophotometry Staphylococcus aureus 440.0 nM
Inhibition of Mycobacterium tuberculosis His6-tagged InhA expressed in Escherichia coli BL21 using trans-2-dodecenoyl-coA as substrate at 50 uM Mycobacterium tuberculosis 99.0 %
Inhibition of His6-tagged recombinant Mycobacterium tuberculosis InhA expressed in protease-deficient Escherichia coli (BL21) using trans-2-dodecenoyl-coenzyme A as substrate assessed as NADH oxidation at 50 uM relative to control Mycobacterium tuberculosis 99.0 %
Inhibition of Mycobacterium tuberculosis His6-tagged wild type InhA expressed in Escherichia coli BL21 at 50 uM using DDCoA as substrate relative to control Mycobacterium tuberculosis 99.0 %
Inhibition of Mycobacterium tuberculosis InhA Mycobacterium tuberculosis 220.0 nM
Uncompetitive inhibition of Mycobacterium tuberculosis InhA using trans-2-dodecenoyl-CoA as substrate in presence of NADH Mycobacterium tuberculosis 200.0 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 -1.82 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.41 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 4.443 %
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 0.09 % 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 -0.01 % 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 0.09 % 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 -0.01 %
Inhibition of Mycobacterium tuberculosis InhA assessed as effect on NADH oxidation incubated for 10 mins by spectrophotometry None 460.0 nM
Inhibition of wild type InhA in Mycobacterium tuberculosis H37Rv using trans-2-dodecenoyl-coenzyme A as substrate at 50 uM Mycobacterium tuberculosis H37Rv 99.0 %
Inhibition of recombinant Mycobacterium tuberculosis His6-tagged InHA expressed in Escherichia coli BL21 using trans-2-dodecenoyl-Coenzyme A as substrate at 50 uM relative to control Mycobacterium tuberculosis 99.0 %
Inhibition of recombinant Mycobacterium tuberculosis His6-tagged InHA expressed in Escherichia coli BL21 using trans-2-dodecenoyl-Coenzyme A as substrate at 5 uM relative to control Mycobacterium tuberculosis 95.0 %

Environmental Exposure

Environmental Exposure Map
Countries
India
Sweden

Cross References

Resources Reference
ChEBI 164200
ChEMBL CHEMBL849
DrugBank DB08604
DrugCentral 3631
FDA SRS 4NM5039Y5X
Human Metabolome Database HMDB0061385
KEGG C12059
PDB TCL
PubChem 5564
SureChEMBL SCHEMBL3269
ZINC ZINC000000002216
CONTENTS