Structure

InChI Key GKTWGGQPFAXNFI-HNNXBMFYSA-N
Smiles COC(=O)[C@H](c1ccccc1Cl)N1CCc2sccc2C1
InChI
InChI=1S/C16H16ClNO2S/c1-20-16(19)15(12-4-2-3-5-13(12)17)18-8-6-14-11(10-18)7-9-21-14/h2-5,7,9,15H,6,8,10H2,1H3/t15-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H16ClNO2S
Molecular Weight 321.83
AlogP 3.67
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 0.0
Number of Rotational Bond 3.0
Polar Surface Area 29.54
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 21.0
Assay Description Organism Bioactivity Reference
Mechanism based inhibition of human cytochrome P450 2B6 using human liver microsomes Homo sapiens 500.0 nM
DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 562.0 nM DRUGMATRIX: Transporter, Serotonin (5-Hydroxytryptamine) (SERT) radioligand binding (ligand: [3H] Paroxetine) None 299.0 nM
Antiplatelet activity against New Zealand white rabbit platelets assessed as inhibition of ADP-induced platelet aggregation at 9.6 ug/mL treated 2 mins before ADP challenge measured after 4 mins by turbidimetric analysis Oryctolagus cuniculus 85.2 %
Antiplatelet activity against New Zealand white rabbit platelets assessed as inhibition of collagen-induced platelet aggregation at 9.6 ug/mL treated 2 mins before collagen challenge measured after 4 mins by turbidimetric analysis Oryctolagus cuniculus 3.5 %
Time dependent inhibition of CYP2B6 in human liver microsomes Homo sapiens 500.0 nM
Antiplatelet activity against New Zealand white rabbit platelets assessed as inhibition of ADP-induced platelet aggregation preincubated at 30 uM for 2 mins before challenge measured after 2 mins by spectrophotometry Oryctolagus cuniculus 80.2 %
Inhibition of CYP2B6 variant in human liver microsomes harboring CYP2B6*1/*1 genotype assessed as 8-hydroxyefavirenz formation using efavirenz as substrate after 15 mins by LC/MS/MS analysis Homo sapiens 140.0 nM
Inhibition of CYP2B6 variant in human liver microsomes harboring CYP2B6*6/*6 genotype assessed as 8-hydroxyefavirenz formation using efavirenz as substrate after 15 mins by LC/MS/MS analysis Homo sapiens 50.0 nM
Time dependent inhibition of CYP1A2 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C9 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2C19 in human liver microsomes at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2D6 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP3A4 (unknown origin) at 100 uM by LC/MS system Homo sapiens 35.0 %
Time dependent inhibition of CYP2C8 (unknown origin) at 100 uM by LC/MS system Homo sapiens 10.0 %
Time dependent inhibition of CYP2B6 (unknown origin) at 0.3 uM by LC/MS system Homo sapiens 44.0 %
Anti-platelet activity in rabbit platelet-rich plasma assessed as inhibition of ADP-induced platelet aggregation at 100 uM incubated for 5 mins at 37 degC by aggregometry Oryctolagus cuniculus 94.5 %
Anti-platelet activity in rabbit platelet-rich plasma assessed as inhibition of ADP-induced platelet aggregation at 50 uM incubated for 5 mins at 37 degC by aggregometry Oryctolagus cuniculus 92.3 %
Anti-platelet activity in rabbit platelet-rich plasma assessed as inhibition of ADP-induced platelet aggregation at 25 uM incubated for 5 mins at 37 degC by aggregometry Oryctolagus cuniculus 77.6 %
Anti-platelet activity in rabbit platelet-rich plasma assessed as inhibition of ADP-induced platelet aggregation at 12.5 uM incubated for 5 mins at 37 degC by aggregometry Oryctolagus cuniculus 86.9 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 12.7 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -0.51 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 14.99 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 15.58 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 23.6 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 2.18 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -8.15 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 17.95 %
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 0.03 % 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 0.03 %

Related Entries

Environmental Exposure

Countries
Croatia
Czech Republic
Germany
Hungary
Romania
Serbia
Slovenia

Cross References

Resources Reference
ChEBI 37941
ChEMBL CHEMBL1771
DrugBank DB00758
DrugCentral 708
FDA SRS A74586SNO7
Human Metabolome Database HMDB0005011
Guide to Pharmacology 7150
KEGG D07729
PDB CGE
PharmGKB PA449053
PubChem 60606
SureChEMBL SCHEMBL4769
ZINC ZINC000034781704