BEDAQUILINE

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Synonyms
Status
Molecule Category UNKNOWN
ATC J04AK05
UNII 78846I289Y

Structure

InChI Key QUIJNHUBAXPXFS-XLJNKUFUSA-N
Smiles COc1nc2ccc(Br)cc2cc1[C@@H](c1ccccc1)[C@@](O)(CCN(C)C)c1cccc2ccccc12
InChI
InChI=1S/C32H31BrN2O2/c1-35(2)19-18-32(36,28-15-9-13-22-10-7-8-14-26(22)28)30(23-11-5-4-6-12-23)27-21-24-20-25(33)16-17-29(24)34-31(27)37-3/h4-17,20-21,30,36H,18-19H2,1-3H3/t30-,32-/m1/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C32H31BrN2O2
Molecular Weight 555.52
AlogP 7.13
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 45.59
Molecular species BASE
Aromatic Rings 5.0
Heavy Atoms 37.0
Assay Description Organism Bioactivity Reference
Inhibition of Mycobacterium smegmatis ATCC 607 ATP synthase subunit c-mediated ATP synthesis after 60 mins by luminometry Mycobacterium smegmatis 2.5 nM Inhibition of Mycobacterium smegmatis ATCC 607 ATP synthase subunit c-mediated ATP synthesis after 60 mins by luminometry Mycobacterium smegmatis 25.0 nM
Binding affinity to Bacillus PS3 ATP synthase subunit c Bacillus sp. PS3 500.0 nM
Inhibition of ATP synthase mediated ATP production in human OVCAR3 cells at 200 uM Homo sapiens 35.0 %
Inhibition of ATP synthase mediated ATP production in human OVCAR3 cells at 5 uM Homo sapiens 90.0 %
Inhibition of ATP synthase mediated ATP production in human OVCAR3 cells at 1 uM Homo sapiens 90.0 %
Inhibition of Mycobacterium smegmatis MC2 155 ATP synthase subunit c-mediated ATP production Mycobacterium smegmatis 10.0 nM
Inhibition of Mycobacterium smegmatis MC2 155 ATP synthase subunit c-mediated ATP production at 100 nM Mycobacterium smegmatis 10.0 nM
Inhibition of ATP synthase in M18 mouse liver mitochondria assessed as inhibition of oxygen consumption Mus musculus 80.0 %
Inhibition of ATP synthase in bovine heart mitochondria assessed as inhibition of oxygen consumption Bos taurus 50.0 %
Inhibition of oxidative phosphorylation in Mycobacterium smegmatis membrane vesicles assessed as inhibition of NADH driven ATP synthesis by luciferin/luciferase assay Mycobacterium smegmatis 1.0 nM
Inhibition of human ERG channel Homo sapiens 0.2 ug.mL-1
Antimycobacterial activity against Mycobacterium tuberculosis H37Rv expressing Lux assessed as reduction in growth measured after 3 weeks by bioluminescence assay Mycobacterium tuberculosis H37Rv 50.0 nM
Inhibition of ATP synthase in Mycobacterium smegmatis inverted membrane vesicles assessed as reduction in oxidative phosphorylation of ADP incubated for 60 mins in presence of NADH by luciferin/luciferase coupled reporter gene assay Mycobacterium smegmatis 5.0 nM
Inhibition of human ERG Homo sapiens 370.0 nM
Cytotoxicity against African green monkey Vero cells after 72 hrs by MTS-PMS assay Chlorocebus sabaeus 10.0 ug.mL-1
Inhibition of human ERG assessed as prolongation of QT interval Homo sapiens 370.0 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 6.62 %
Inhibition of Mycobacterium phlei DSM-43239 C-terminal ATP-synthase assessed as reduction in luciferase activity incubated for 10 mins in presence of ATP by luminometric method Mycolicibacterium phlei DSM 43239 = CCUG 21000 20.0 nM
Cytotoxicity against African green monkey Vero cells measured after 72 hrs by CellTiter 96 aqueous non-radioactive cell proliferation assay Chlorocebus sabaeus 10.0 ug.mL-1
Cytotoxicity against African green monkey Vero cells after 72 hrs by MTS-PMS assay Chlorocebus aethiops 10.0 ug.mL-1
Cytotoxicity against African green monkey Vero cells measured after 72 hrs by MTT assay Chlorocebus aethiops 10.0 ug.mL-1
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 29.38 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -22.19 %
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 0.06 % 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 0.18 % 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 0.06 % 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 0.18 %
Growth inhibiting activity of Naegleria gruberi in vitro Naegleria gruberi 56.3 %
Cytotoxicity against African green monkey Vero cells assessed as reduction in cell viability incubated for 72 hrs by MTS-PBS assay Chlorocebus sabaeus 4.0 ug.mL-1
Inhibition of Mycobacterium smegmatis ATPsynthase Mycobacterium smegmatis 0.55 ug.mL-1

Cross References

Resources Reference
ChEBI 72292
ChEMBL CHEMBL376488
DrugBank DB08903
DrugCentral 4741
FDA SRS 78846I289Y
Guide to Pharmacology 11171
KEGG C14122
PDB BQ1
PubChem 5388906
SureChEMBL SCHEMBL295482
ZINC ZINC000004655029
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