PLECONARIL

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Synonyms
Status
Molecule Category Free-form
ATC J05AX06
UNII 9H4570Q89D
EPA CompTox DTXSID8057649

Structure

InChI Key KQOXLKOJHVFTRN-UHFFFAOYSA-N
Smiles Cc1cc(CCCOc2c(C)cc(-c3noc(C(F)(F)F)n3)cc2C)on1
InChI
InChI=1S/C18H18F3N3O3/c1-10-7-13(16-22-17(27-24-16)18(19,20)21)8-11(2)15(10)25-6-4-5-14-9-12(3)23-26-14/h7-9H,4-6H2,1-3H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C18H18F3N3O3
Molecular Weight 381.35
AlogP 4.68
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 6.0
Polar Surface Area 74.18
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 27.0

Bioactivity

Mechanism of Action Action Reference
VP1 capsid protein disrupting agent DISRUPTING AGENT PubMed PubMed PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- 1259 - - -
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 6310 - - -
Enzyme Protease Cysteine protease Cysteine protease PAC clan Cysteine protease C3A subfamily
58 - - - -
Structural protein
4-490 - - - -
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
251 - - - -
Assay Description Organism Bioactivity Reference
In vitro anti-rhinoviral activity against human rhinovirus serotypes 2,3,9,14,16,25 and 39 Enterovirus 136.0 nM
Anti-HRV activity against HRV serotype 14 human rhinovirus type 14 0.03431 ug.mL-1
Anti-HRV activity against HRV serotype 15 Human rhinovirus 15 0.0698 ug.mL-1
Anti-HRV activity against HRV serotype 16 Human rhinovirus 16 0.108 ug.mL-1
Anti-HRV activity against HRV serotype 2 human rhinovirus type 2 0.02647 ug.mL-1
Anti-HRV activity against HRV serotype 29 Human rhinovirus 29 0.0454 ug.mL-1
Anti-HRV activity against HRV serotype 39 Human rhinovirus 39 0.04488 ug.mL-1
Anti-HRV activity against HRV serotype 45 Human rhinovirus 45 1.908 ug.mL-1
Anti-HRV activity against HRV serotype 51 Human rhinovirus 51 0.0304 ug.mL-1
Anti-HRV activity against HRV serotype 59 Human rhinovirus 59 0.3873 ug.mL-1
Anti-HRV activity against HRV serotype 63 Human rhinovirus 63 0.0623 ug.mL-1
Anti-HRV activity against HRV serotype 70 Human rhinovirus 70 0.05387 ug.mL-1
Anti-HRV activity against HRV serotype 72 Human rhinovirus 72 0.4687 ug.mL-1
Anti-HRV activity against HRV serotype 85 Human rhinovirus 85 0.034 ug.mL-1
Anti-HRV activity against HRV serotype 86 Human rhinovirus 86 0.07004 ug.mL-1
Anti-HRV activity against HRV serotype 89 human rhinovirus type 89 0.02933 ug.mL-1
Anti-HRV activity against HRV serotype 9 Human rhinovirus 9 0.03716 ug.mL-1
Inhibition of HRV Protease 3CP (serotype 14). Human rhinovirus B 58.0 nM
Median effective concentration against HRV serotypes; Number of serotypes 16 Human rhinovirus sp. 0.04963 ug.mL-1
Effective concentration against HRV serotype 2 (assay was run at least six times) Human rhinovirus sp. 0.02647 ug.mL-1
Effective concentration against HRV serotype 9 (assay was run at least six times) Human rhinovirus sp. 0.03716 ug.mL-1
Effective concentration against HRV serotype 14 (assay was run at least six times) Human rhinovirus sp. 0.03431 ug.mL-1
Effective concentration against HRV serotype 15 (assay was run at least six times) Human rhinovirus sp. 0.0698 ug.mL-1
Effective concentration against HRV serotype 16 (assay was run at least six times) Human rhinovirus sp. 0.108 ug.mL-1
Effective concentration against HRV serotype 29 (assay was run at least six times) Human rhinovirus sp. 0.0454 ug.mL-1
Effective concentration against HRV serotype 39 (assay was run at least six times) Human rhinovirus sp. 0.04488 ug.mL-1
Effective concentration against HRV serotype 45 (assay was run at least six times) Human rhinovirus sp. 1.908 ug.mL-1
Effective concentration against HRV serotype 51 (assay was run at least six times) Human rhinovirus sp. 0.0304 ug.mL-1
Effective concentration against HRV serotype 59 (assay was run at least six times) Human rhinovirus sp. 0.3873 ug.mL-1
Effective concentration against HRV serotype 63 (assay was run at least six times) Human rhinovirus sp. 0.0623 ug.mL-1
Effective concentration against HRV serotype 70 (assay was run at least six times) Human rhinovirus sp. 0.05387 ug.mL-1
Effective concentration against HRV serotype 72 (assay was run at least six times) Human rhinovirus sp. 0.4687 ug.mL-1
Effective concentration against HRV serotype 85 (assay was run at least six times) Human rhinovirus sp. 0.034 ug.mL-1
Effective concentration against HRV serotype 86 (assay was run at least six times) Human rhinovirus sp. 0.07004 ug.mL-1
Effective concentration against HRV serotype 89 (assay was run at least six times) Human rhinovirus sp. 0.02933 ug.mL-1
Antiviral activity against HRV2 in HeLa cells Human rhinovirus 2 0.01 ug.mL-1
Antiviral activity against HRV1A in HeLa cells Human rhinovirus 1A 0.02 ug.mL-1
Antiviral activity against HRV14 in HeLa cells Human rhinovirus 14 0.02 ug.mL-1
Antiviral activity against HRV16 in HeLa cells Human rhinovirus 16 0.02 ug.mL-1
Inhibition of HRV2 absorption on HeLa cells assessed as reduction in plaques at 0.25 ug/ml after 2 hrs Human rhinovirus 2 100.0 %
Inhibition of HRV2 replication cycle progression Human rhinovirus 2 40.0 nM
Inhibition of HRV16 replication cycle progression Human rhinovirus 16 570.0 nM
Antiviral activity against HRV-14 Human rhinovirus 14 0.03 ug.mL-1
Antiviral activity against Human rhinovirus 14 infected in human HeLa Ohio cells assessed as inhibition of virus-induced cytopathic effect by CellTiter-Glo assay Human rhinovirus 14 100.0 nM
Antiviral activity against Human rhinovirus 2 infected in human HeLa Ohio cells assessed as inhibition of virus-induced cytopathic effect by CellTiter-Glo assay Human rhinovirus 2 100.0 nM
Activation of human PXR expressed in african green monkey CV1 cells transfected with pSG5-hPXRDATG and (ER6)3-tk-CAT reporter Homo sapiens 251.19 nM
Antirhinoviral activity against Human rhinovirus A infected in human HeLa cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay Human rhinovirus sp. 0.0374 ug.mL-1
Antirhinoviral activity against Human rhinovirus B infected in human HeLa cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay Human rhinovirus sp. 0.2241 ug.mL-1
Antirhinoviral activity against antiviral-resistant Human rhinovirus A infected in human HeLa cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay Human rhinovirus sp. 0.3876 ug.mL-1
Antirhinoviral activity against antiviral-resistant Human rhinovirus B infected in human HeLa cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay Human rhinovirus sp. 0.0338 ug.mL-1
Antirhinoviral activity against major receptor-resistant Human rhinovirus infected in human HeLa cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay Human rhinovirus sp. 0.0492 ug.mL-1
Antirhinoviral activity against minor receptor-resistant Human rhinovirus infected in human HeLa cells assessed as inhibition of virus-induced cytopathic effect after 5 days by MTT assay Human rhinovirus sp. 0.0232 ug.mL-1
Antiviral activity against Coxsackievirus B3 assessed as inhibition of viral replication Human coxsackievirus B3 410.0 nM
Antienteroviral activity against poliovirus 3 infected in african green monkey Vero cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human poliovirus 3 84.0 nM
Antienteroviral activity against Coxsackievirus A9 infected in african green monkey Vero cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human coxsackievirus A9 33.0 nM
Antienteroviral activity against Human rhinovirus 89 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 89 75.0 nM
Antienteroviral activity against Human rhinovirus 86 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 86 89.0 nM
Antienteroviral activity against Human rhinovirus 85 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 85 883.0 nM
Antienteroviral activity against Human rhinovirus 70 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 70 578.0 nM
Antienteroviral activity against Human rhinovirus 63 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 63 85.0 nM
Antienteroviral activity against Human rhinovirus 59 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus A59 471.0 nM
Antienteroviral activity against Human rhinovirus 41 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 41 655.0 nM
Antienteroviral activity against Human rhinovirus 39 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 39 44.0 nM
Antienteroviral activity against Human rhinovirus 29 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 29 26.0 nM
Antienteroviral activity against Human rhinovirus 15 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 15 166.0 nM
Antienteroviral activity against Human rhinovirus 9 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 9 83.0 nM
Antienteroviral activity against Human rhinovirus 2 infected in human HeLa Rh cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 2 7.0 nM
Antienteroviral activity against Human rhinovirus 14 infected in human HeLa cells assessed as protection against virus-induced cytopathic effect after 2 to 3 days by MTS assay Human rhinovirus 14 177.0 nM
Antiviral activity against Coxsackie virus B3 assessed as inhibition of viral replication Human coxsackievirus B3 300.0 nM
Antiviral activity against Coxsackievirus B5 infected in African green monkey Vero 76 cells after 3 days by plaque reduction assay Human coxsackievirus B5 5.0 nM
Antiviral activity against Coxsackievirus B3 infected in African green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect Human coxsackievirus B3 2.5 nM
Antiviral activity against human CVB5 infected in african green monkey Vero76 cells assessed as inhibition of virus-induced cytopathogenicity after 3 days by plaque reduction assay Human coxsackievirus B5 8.0 nM
Antiviral activity against Human Rhinovirus B serotype 14 infected in HeLa Rh cells assessed as reduction of virus-induced cytopathic effect after 3 days by MTS assay Rhinovirus B 200.0 nM
Antiviral activity against Coxsackievirus B3 infected in African green monkey Vero cells assessed as inhibition of virus-induced cytopathic effect Human coxsackievirus B3 1.0 nM
Antiviral activity against Human rhinovirus B14 infected in human H1HeLa cells assessed as protection against virus induced cytopathic effect after 3 days by MTT assay Human rhinovirus B14 75.0 nM
Antiviral activity against Human rhinovirus A21 infected in human H1HeLa cells assessed as protection against virus induced cytopathic effect after 3 days by MTT assay Human rhinovirus A21 73.0 nM
Antiviral activity against Human rhinovirus A71 infected in human H1HeLa cells assessed as protection against virus induced cytopathic effect after 3 days by MTT assay Human rhinovirus A71 9.4 nM
Antiviral activity against Human rhinovirus A16 infected in human H1HeLa cells assessed as protection against virus induced cytopathic effect after 3 days by MTT assay Human rhinovirus A16 350.0 nM
Antiviral activity against human poliovirus 3 infected in human HeLa cells assessed as reduction in virus-induced cytopathicity incubated for 3 days by MTT assay Human poliovirus 3 510.0 nM
Antiviral activity against human coxsackievirus B1 infected in human HeLa cells assessed as reduction in virus-induced cytopathicity incubated for 3 days by MTT assay Human coxsackievirus B1 130.0 nM
Antiviral activity against human rhinovirus 14 infected in human H1HeLa cells assessed as reduction in virus-induced cytopathicity incubated for 3 days by MTT assay Human rhinovirus 14 310.0 nM
Antiviral activity against human rhinovirus 21 infected in human H1HeLa cells assessed as reduction in virus-induced cytopathicity incubated for 3 days by MTT assay Human rhinovirus A21 83.0 nM
Antiviral activity against human rhinovirus 71 infected in human H1HeLa cells assessed as reduction in virus-induced cytopathicity incubated for 3 days by MTT assay Human rhinovirus A71 13.0 nM
Antiviral activity against Human enterovirus B Faulkner ATCC VR 185 infected in African green monkey Vero 76 cells assessed as protection against virus-induced cytopathic effect after 3 days by crystal violet staining-based plaque reduction assay Human enterovirus B 5.0 nM
Antiviral activity against Human rhinovirus serotype 14 infected in human HeLa cells assessed as reduction in virus-induced cytopathic effect after 24 to 36 hrs by MTT assay Human rhinovirus B14 300.0 nM
Antiviral activity against Human rhinovirus serotype 39 infected in human HeLa cells assessed as reduction in virus-induced cytopathic effect after 24 to 36 hrs by MTT assay Human rhinovirus A39 100.0 nM
Antiviral activity against Coxsackievirus B5 Ohio-1 ATCC VR 29 infected in African green monkey Vero 76 cells after 3 days by plaque reduction assay Coxsackievirus B5 5.0 nM
Antiviral activity against Human rhinovirus B14 infected in human HeLa Rh cells assessed as protection against virus induced cytopathic effect after 3 days in presence of 10% inactivated FBS by MTT assay Human rhinovirus B14 300.0 nM
Antiviral activity against Human rhinovirus B14 infected in human H1HeLa cells assessed as inhibition of viral replication after 3 days by MTT assay Human rhinovirus B14 92.0 nM
Antiviral activity against Human rhinovirus A21 infected in human H1HeLa cells assessed as inhibition of viral replication after 3 days by MTT assay Human rhinovirus A21 73.0 nM
Antiviral activity against Human rhinovirus A71 infected in human H1HeLa cells assessed as inhibition of viral replication after 3 days by MTT assay Human rhinovirus A71 9.4 nM
Inhibition of Rhinovirus B14 capsid infected in human HeLa Rh cells assessed as reduction in virus-induced cytopathic effect after 3 days by MTS assay Human rhinovirus B14 30.0 nM
Inhibition of Rhinovirus A02 capsid infected in human HeLa Rh cells assessed as reduction in virus-induced cytopathic effect after 3 days by MTS assay Human rhinovirus A2 15.0 nM
Inhibition of Rhinovirus A08 capsid infected in human HeLa Rh cells assessed as reduction in virus-induced cytopathic effect after 3 days by MTS assay Human rhinovirus A8 490.0 nM
Inhibition of Rhinovirus A28 capsid infected in human HeLa Rh cells assessed as reduction in virus-induced cytopathic effect after 3 days by MTS assay Rhinovirus A 15.0 nM
Inhibition of Rhinovirus A85 capsid infected in human HeLa Rh cells assessed as reduction in virus-induced cytopathic effect after 3 days by MTS assay Human rhinovirus A85 11.0 nM
Inhibition of Rhinovirus A89 capsid infected in human HeLa Rh cells assessed as reduction in virus-induced cytopathic effect after 3 days by MTS assay Human rhinovirus A89 4.0 nM
Inhibition of Rhinovirus B70 capsid infected in human HeLa Rh cells assessed as reduction in virus-induced cytopathic effect after 3 days by MTS assay Human rhinovirus 70 167.0 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 -2.6 %
Antiviral activity against Enterovirus clinical isolate Enterovirus 30.0 nM
Cytotoxicity against human HeLa cells after 3 days by MTT assay Homo sapiens 180.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 26.3 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 6.7 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 3.549 %
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 -0.02 % 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 -0.11 % 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 -0.11 % 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 -0.02 %
Antiviral activity against Coxsackievirus B3 infected in Vero cells assessed as reduction in virus-induced cytopathic effect incubated for 48 hrs by Reed-Muench method Human coxsackievirus B3 2.0 nM
Antiviral activity against wild type Coxsackievirus B3 97927 infected in human HeLa cell line assessed as inhibition of virus-induced cytopathic effect measured after 48 hrs by crystal violet uptake assay Human coxsackievirus B3 10.0 nM
Antiviral activity against Rhinovirus A2 infected in human HeLa cell line assessed as inhibition of virus-induced cytopathic effect measured after 72 hrs by crystal violet uptake assay Human rhinovirus A2 40.0 nM
Antiviral activity against Rhinovirus B14 infected in human HeLa cell line assessed as inhibition of virus-induced cytopathic effect measured after 72 hrs by crystal violet uptake assay Human rhinovirus B14 70.0 nM

Cross References

Resources Reference
ChEMBL CHEMBL29609
DrugBank DB05105
DrugCentral 4690
FDA SRS 9H4570Q89D
PDB W11
PubChem 1684
SureChEMBL SCHEMBL49383
ZINC ZINC000001537619
CONTENTS