HEXACHLOROPHENE

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Trade Names
Synonyms
Status
Molecule Category Free-form
ATC D08AE01
UNII IWW5FV6NK2
EPA CompTox DTXSID6020690

Structure

InChI Key ACGUYXCXAPNIKK-UHFFFAOYSA-N
Smiles Oc1c(Cl)cc(Cl)c(Cl)c1Cc1c(O)c(Cl)cc(Cl)c1Cl
InChI
InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21/h2-3,20-21H,1H2

Physicochemical Descriptors

Property Name Value
Molecular Formula C13H6Cl6O2
Molecular Weight 406.91
AlogP 6.61
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 2.0
Polar Surface Area 40.46
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 21.0

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 Hydrolase
- 1600 - - -
Enzyme Phosphodiesterase
- 11000 - - -
Enzyme Transferase
- 51000 - - -
Enzyme
- 11000 - 5550 85
Other cytosolic protein
- 1300 - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 3
Unclassified protein
- 9100-9100 - - 96-101
Assay Description Organism Bioactivity Reference
Inhibition of yeast Hst2 at 10 times IC50 by fluorimetric assay relative to control Saccharomyces cerevisiae 85.0 %
PUBCHEM_BIOASSAY: Estrogen Receptor-beta Coactivator Binding Inhibitors ELISA Secondary Assay. (Class of assay: confirmatory) [Related pubchem assays: 633 (Primary screen preceding this ELISA dose response confirmation assay.), 733 (Primary dose response assay preceding this ELISA dose response confirmation assay.)] Homo sapiens 98.27 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify Compounds Cytotoxic to Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1900 (Counter Screen), 1677 (Project Summary), 1902 (Retest at Dose), 1662 (Primary HTS)] Streptococcus 262.0 nM
PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Identify Compounds Cytotoxic to SK(-)GAS Group A Streptococcus. (Class of assay: confirmatory) [Related pubchem assays: 1677 (Project Summary), 1662 (Primary HTS)] Streptococcus 244.0 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 202.0 nM
PUBCHEM_BIOASSAY: A Cell Based Assay for the Identification of Lead Compounds with Inhibitory Activity against HIV-1 Fusion (CCR5 Tropic HIV-1 Fusion Inhibition Assay) - Dose Response. (Class of assay: confirmatory) None 970.0 nM
Induction of toxin TSST-1 production in Staphylococcus aureus MN8 at 1.00 mM after 24 hrs relative to control Staphylococcus aureus 48.1 %
Induction of toxin TSST-1 production in Staphylococcus aureus MN8 at 2.00 mM after 24 hrs relative to control Staphylococcus aureus 19.6 %
Induction of toxin TSST-1 production in Staphylococcus aureus FRI-1187 at 3.00 mM after 24 hrs relative to control Staphylococcus aureus 63.5 %
Induction of toxin TSST-1 production in Staphylococcus aureus FRI-1187 at 1.50 mM after 24 hrs relative to control Staphylococcus aureus 74.3 %
DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: Myelin Basic Protein) Escherichia coli 196.0 nM
DRUGMATRIX: Protein Serine/Threonine Kinase, p38alpha enzyme inhibition (substrate: Myelin Basic Protein) Escherichia coli 87.6 nM
DRUGMATRIX: Protein Tyrosine Kinase, EGF Receptor enzyme inhibition (substrate: Poly(Glu:Tyr)) None 748.6 nM
DRUGMATRIX: Adenosine A2A radioligand binding (ligand: AB-MECA) None 906.0 nM
DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) None 638.9 nM DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) None 361.1 nM
DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) None 644.3 nM
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 7.55 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 3.11 %
PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 3.0 nM
PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 108.5 nM
PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 31.21 nM
PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 32.0 nM
PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area decrease-IC50. (Class of assay: confirmatory) None 405.0 nM
PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 57.2 nM
PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 459.6 nM
PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: confirmatory) None 15.7 nM
Inhibition of wild type His-tagged translin/trax E126A mutant (unknown origin) coexpressed in Escherichia coli BL21 cells using RNase Alert as substrate at 30 uM incubated for 10 mins prior to substrate addition monitored over 60 mins by fluorescence assay Homo sapiens 66.0 %
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 92.91 %
Antiviral activity against SARS-CoV-2 (viral titer) measured by plaque assay in Vero cells at MOI 0.0125 after 24 hr Chlorocebus sabaeus 900.0 nM
Inhibition of Escherichia coli GroEL expressed in Escherichia coliDH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured soluble pig heart MDH refolding by measuring MDH enzyme activity using sodium mesoxalate as substrate after 20 to 40 mins by malachite green dye based spectrometric analysis relative to untreated control Escherichia coli 96.0 %
Inhibition of Escherichia coli GroEL expressed in Escherichia coli DH5alpha/Escherichia coli GroES expressed in Escherichia coli BL21 (DE3) assessed as reduction in GroEL/GroES-mediated denatured rhodanese refolding by measuring rhodanese enzyme activity after 45 mins by Fe(SCN)3 dye based spectrometric analysis relative to untreated control Escherichia coli 101.0 %
Inhibition of N-terminal His6-sumo-tagged full length Staphylococcus aureus ClpP expressed in Escherichia coli BL2 (DE3) at 10 uM pre-incubated for 10 mins before Suc-LY-AMC addition and measured after 1 hr by fluorescence based assay relative to control Staphylococcus aureus 50.0 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 22.43 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 29.72 %
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 43.72 % 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 0.54 % 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 43.72 % 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 0.54 %

Cross References

Resources Reference
ChEBI 5693
ChEMBL CHEMBL496
DrugBank DB00756
DrugCentral 1364
FDA SRS IWW5FV6NK2
Human Metabolome Database HMDB0014894
Guide to Pharmacology 11069
KEGG C08039
PDB H3P
PharmGKB PA449871
PubChem 3598
SureChEMBL SCHEMBL15579
ZINC ZINC000001530968
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