BIRABRESIB

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
UNII X40LKS49S3

Structure

InChI Key GNMUEVRJHCWKTO-FQEVSTJZSA-N
Smiles Cc1sc2c(c1C)C(c1ccc(Cl)cc1)=N[C@@H](CC(=O)Nc1ccc(O)cc1)c1nnc(C)n1-2
InChI
InChI=1S/C25H22ClN5O2S/c1-13-14(2)34-25-22(13)23(16-4-6-17(26)7-5-16)28-20(24-30-29-15(3)31(24)25)12-21(33)27-18-8-10-19(32)11-9-18/h4-11,20,32H,12H2,1-3H3,(H,27,33)/t20-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C25H22ClN5O2S
Molecular Weight 492.0
AlogP 5.53
Hydrogen Bond Acceptor 7.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 4.0
Polar Surface Area 92.4
Molecular species NEUTRAL
Aromatic Rings 4.0
Heavy Atoms 34.0

Bioactivity

Mechanism of Action Action Reference
Bromodomain and extra-terminal motif (BET) inhibitor INHIBITOR PubMed
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Epigenetic regulator Reader Bromodomain
- 9-197 - 6-12 -
Assay Description Organism Bioactivity Reference
Displacement of FAM-labeled ZBA248 from BRD4 BD1 (44 to 168 amino acid residues) (unknown origin) expressed in Rosetta2 DE3 cells after 30 mins by fluorescence polarization assay Homo sapiens 25.5 nM Displacement of FAM-labeled ZBA248 from BRD4 BD1 (44 to 168 amino acid residues) (unknown origin) expressed in Rosetta2 DE3 cells after 30 mins by fluorescence polarization assay Homo sapiens 10.9 nM
Displacement of FAM-labeled ZBA248 from BRD4 BD2 (333 to 460 amino acid residues) (unknown origin) expressed in Rosetta2 DE3 cells after 30 mins by fluorescence polarization assay Homo sapiens 16.6 nM Displacement of FAM-labeled ZBA248 from BRD4 BD2 (333 to 460 amino acid residues) (unknown origin) expressed in Rosetta2 DE3 cells after 30 mins by fluorescence polarization assay Homo sapiens 6.0 nM
Displacement of FAM-labeled ZBA248 from BRD2 BD1 (72 to 205 amino acid residues) (unknown origin) expressed in Rosetta2 DE3 cells after 30 mins by fluorescence polarization assay Homo sapiens 16.6 nM
Displacement of FAM-labeled ZBA248 from BRD2 BD2 (349 to 460 amino acid residues) (unknown origin) expressed in Rosetta2 DE3 cells after 30 mins by fluorescence polarization assay Homo sapiens 5.4 nM
Displacement of FAM-labeled ZBA248 from BRD3 BD1 (24 to 144 amino acid residues) (unknown origin) expressed in Rosetta2 DE3 cells after 30 mins by fluorescence polarization assay Homo sapiens 10.7 nM
Displacement of FAM-labeled ZBA248 from BRD3 BD2 (306 to 417 amino acid residues) (unknown origin) expressed in Rosetta2 DE3 cells after 30 mins by fluorescence polarization assay Homo sapiens 4.0 nM
Inhibition of BRD4 bromodomain 1 (unknown origin) Homo sapiens 20.0 nM
Inhibition of acetylated H4 binding to BRD4 (unknown origin) Homo sapiens 92.0 nM
Inhibition of acetylated H4 binding to BRD2 (unknown origin) Homo sapiens 92.0 nM
Inhibition of acetylated H4 binding to BRD3 (unknown origin) Homo sapiens 92.0 nM
Inhibition of BRD4 BD1-BD2 (unknown origin) using tetraacetylated histone peptide as substrate after 2 hrs by alphascreen assay Homo sapiens 16.0 nM
Antiproliferative activity against human TY82 cells Homo sapiens 67.0 nM
Antiproliferative activity against human THP1 cells Homo sapiens 33.0 nM
Inhibition of BRD4 bromodomain-1 (unknown origin) by AlphaScreen assay Homo sapiens 92.0 nM
Antiproliferative activity against human LNCAP cells Homo sapiens 111.4 nM
Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD2 bromodomain 1 (72 to 205 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 16.6 nM Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD2 bromodomain 1 (72 to 205 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 33.3 nM
Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD2 bromodomain 2 (349 to 460 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 5.4 nM Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD2 bromodomain 2 (349 to 460 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 24.8 nM
Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD3 bromodomain 1 (24 to 144 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 10.7 nM Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD3 bromodomain 1 (24 to 144 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 38.5 nM
Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD3 bromodomain 2 (306 to 417residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 4.0 nM Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD3 bromodomain 2 (306 to 417residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 21.0 nM
Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD4 bromodomain 1 (44 to 168 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 25.5 nM Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD4 bromodomain 1 (44 to 168 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 10.9 nM
Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD4 bromodomain 2 (333 to 460 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 6.0 nM Inhibition of FAM-labeled ZBA248 binding to recombinant N-terminal His6-tagged BRD4 bromodomain 2 (333 to 460 residues) (unknown origin) expressed in Escherichia coli Rosetta2 DE3 after 30 mins by fluorescence polarization assay Homo sapiens 16.6 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 -2.34 %
Inhibition of recombinant full length human N-terminal His6-tagged BRD4 (2 to 1362 residues) expressed in baculovirus infected insect cells using histone H4 peptide as substrate by alpha screen assay Homo sapiens 92.0 nM
Antiproliferative activity against human MV4-11 cells assessed as cell growth inhibition after 4 days by CCK8 assay Homo sapiens 17.6 nM
Binding affinity to human recombinant BRD4 BD1 (44 to 168 residues) by fluorescence polarization assay Homo sapiens 11.7 nM
Binding affinity to human recombinant BRD4 BD2 (333 to 460 residues) by fluorescence polarization assay Homo sapiens 9.9 nM
Binding affinity to human recombinant BRD3 BD1 (24 to 144 residues) by fluorescence polarization assay Homo sapiens 8.7 nM
Binding affinity to human recombinant BRD3 BD2 (306 to 417 residues) by fluorescence polarization assay Homo sapiens 11.2 nM
Binding affinity to human recombinant BRD2 BD1 (72 to 205 residues) by fluorescence polarization assay Homo sapiens 33.2 nM
Binding affinity to human recombinant BRD2 BD2 (349 to 460 residues) by fluorescence polarization assay Homo sapiens 10.3 nM
Antiproliferative activity against human MM1S cells assessed as cell growth inhibition after 4 days by CCK8 assay Homo sapiens 22.7 nM
Binding affinity to human BRD4 BD1 (44 to 168 residues) by fluorescence polarization assay Homo sapiens 23.0 nM Binding affinity to human BRD4 BD1 (44 to 168 residues) by fluorescence polarization assay Homo sapiens 5.7 nM
Inhibition of BRD4 (unknown origin) Homo sapiens 92.0 nM
Inhibition of SGRG-K(Ac)-GG-K(Ac)-GLG-K(Ac)-GGA-K(Ac)-RHRKVGG-K-Biotin binding to N-terminal His6-tagged BRD4 bromodomain 1 (49 to 170 residues) (unknown origin) expressed in Escherichia coli BL21 (DE3) preincubated for 15 mins followed by biotin-labeled H4 peptide addition and measured after 10 mins by Alphascreen assay Homo sapiens 40.8 nM
Inhibition of SGRG-K(Ac)-GG-K(Ac)-GLG-K(Ac)-GGA-K(Ac)-RHRKVGG-K-Biotin binding to N-terminal His6-tagged BRD4 bromodomain 2 (344 to 455 residues) (unknown origin) expressed in Escherichia coli BL21 (DE3) preincubated for 15 mins followed by biotin-labeled H4 peptide addition and measured after 10 mins by Alphascreen assay Homo sapiens 197.0 nM
Antiproliferative activity against human MV4-11 cells assessed as reduction in cell viability measured after 72 hrs by Celltitre-glo luminescence assay Homo sapiens 46.3 nM
Antiproliferative activity against human Kasumi-1 cells assessed as reduction in cell viability measured after 72 hrs by Celltitre-glo luminescence assay Homo sapiens 135.0 nM
Antiproliferative activity against human RS4:11 cells assessed as reduction in cell viability measured after 72 hrs by Celltitre-glo luminescence assay Homo sapiens 416.0 nM
Antiproliferative activity against human MM1S cells assessed as reduction in cell viability measured after 72 hrs by Celltitre-glo luminescence assay Homo sapiens 137.0 nM
Displacement of 5-FITC labelled (+)-JQ1 from His6-tagged human BRD4 bromodomain 1 expressed in Escherichia coli BL21(DE3) )-codon plus-RIL cells incubated for 4 hrs in dark condition by fluorescence anisotropy binding assay Homo sapiens 34.3 nM
Antiproliferative activity against human MM1S cells after 72 hrs by CCK8 or SRB assay Homo sapiens 6.3 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 22.08 % SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 -1.965 %
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 0.49 % 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 4.23 % 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 4.23 % 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 0.49 %
Inhibition of His-tagged BRD4 bromodomain 1 (unknown origin) using [Lys (5,8,12,16) Ac] H4(1-21) as substrate by fluorescence based assay Homo sapiens 9.2 nM
Inhibition of His-tagged BRD4 bromodomain 2 (unknown origin) using [Lys (5,8,12,16) Ac] H4(1-21) as substrate by fluorescence based assay Homo sapiens 15.4 nM
Antiproliferative activity against human MV4-11 cells assessed as cell viability after 72 hrs by CCK8 assay Homo sapiens 200.0 nM
Cytotoxicity against human MOLM-14 cells assessed as reduction in cell viability incubated for 72 hrs Homo sapiens 80.0 nM
Anticancer activity against human HL-60 cells assessed as cell growth inhibition by CellTiter-Glo luminescent assay Homo sapiens 820.0 nM

Related Entries

Cross References

Resources Reference
ChEMBL CHEMBL3581647
DrugBank DB15189
FDA SRS X40LKS49S3
Guide to Pharmacology 8359
PDB 6JE
PubChem 9936746
SureChEMBL SCHEMBL2898131
ZINC ZINC000003960759
CONTENTS