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Compound Detail

CHEMBL1957266

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Cc1sc2c(c1C)C(c1ccc(Cl)cc1)=N[C@@H](CC(=O)OC(C)(C)C)c1nnc(C)n1-2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1957266
Phase Preclinical
Structure Type MOL
InChI Key DNVXATUJJDPFDM-KRWDZBQOSA-N
78
Targets
569
Activities
4
Assay Types
23
PK Parameters
20
Publications
0
Known Names

Molecular Properties

457.0
MW (Da)
5.53
ALogP
7
HBA
0
HBD
69.4
PSA (Ų)
0.49
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C23H25ClN4O2S
MW 457.00
Aromatic Rings 3
Heavy Atoms 31
NP-Likeness -1.05

Activity Summary

IC50 463 meas. best 8.7
Kd 73 meas. best 8.21
EC50 17 meas. best 7.52
Ki 16 meas. best 8.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Monocyte
CHEMBL5314323
 IC50 8.7 8.7 2.0 1
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 8.41 7.2304 3.9 190
Bromodomain-containing protein 2
CHEMBL1293289
 IC50 8.41 7.2571 3.9 34
Bromodomain testis-specific protein
CHEMBL1795185
 IC50 8.4 6.9787 4.0 23
Bromodomain-containing protein 3
CHEMBL1795186
 IC50 8.4 7.2889 4.0 27
Bromodomain-containing protein 4
CHEMBL1163125
 Ki 8.28 7.8725 5.3 8
Bromodomain-containing protein 2
CHEMBL1293289
 Kd 8.21 7.3214 6.2 14
C-C motif chemokine 2
CHEMBL1649052
 IC50 8.2 7.2 6.3 2
Bromodomain-containing protein 3
CHEMBL1795186
 Ki 8.18 8.115 6.6 4
Bromodomain-containing protein 4
CHEMBL1163125
 Kd 8.17 7.2532 6.7 38
Bromodomain-containing protein 3
CHEMBL1795186
 Kd 7.93 7.299 11.7 10
VCaP
CHEMBL4296508
 IC50 7.92 7.92 12.0 1
MV4-11
CHEMBL613835
 IC50 7.92 7.063 12.0 20
Bromodomain-containing protein 2
CHEMBL1293289
 Ki 7.9 7.89 12.5 4
Unchecked
CHEMBL612545
 IC50 7.75 6.6467 18.0 15
MM1.S
CHEMBL4296471
 IC50 7.72 7.1929 19.0 7
HT-29
CHEMBL384
 IC50 7.7 6.2667 20.0 6
Bromodomain testis-specific protein
CHEMBL1795185
 Kd 7.66 6.8175 22.0 8
MOLM-13
CHEMBL3706572
 IC50 7.62 6.8767 24.0 3
Unchecked
CHEMBL612545
 EC50 7.52 6.9867 30.0 3
CWR22R
CHEMBL612657
 IC50 7.48 6.995 33.0 4
LNCaP
CHEMBL612518
 IC50 7.3 6.965 50.0 4
Mus musculus
CHEMBL375
 IC50 7.25 7.25 56.0 1
NALM-6
CHEMBL614187
 EC50 7.22 7.22 60.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 7.22 6.322 60.0 5
D283 Med
CHEMBL614476
 IC50 7.22 6.6575 60.0 4
Bromodomain-containing protein 4
CHEMBL1163125
 EC50 7.19 6.95 64.0 3
HEL
CHEMBL613888
 IC50 7.16 7.16 69.0 1
HL-60
CHEMBL383
 IC50 7.16 6.4 70.0 7
HD-MB03
CHEMBL5441366
 IC50 7.11 6.836 78.0 5
ONS-76
CHEMBL2366068
 IC50 7.06 6.8725 87.0 4
LOUCY
CHEMBL2366252
 EC50 7.05 7.05 90.0 1
697
CHEMBL2366253
 EC50 7.05 7.05 90.0 1
SK-OV-3
CHEMBL614925
 IC50 7.0 7.0 100.0 1
OVCAR-5
CHEMBL614214
 IC50 7.0 7.0 100.0 1
OVCAR-3
CHEMBL614213
 IC50 7.0 7.0 100.0 1
OVCAR-8
CHEMBL612555
 IC50 7.0 7.0 100.0 1
A2780
CHEMBL614004
 IC50 7.0 7.0 100.0 1
HEK-293T
CHEMBL3706568
 IC50 6.97 6.97 107.0 1
D341 cell line
CHEMBL614478
 IC50 6.8 6.5025 157.0 4
Hs-578T
CHEMBL614645
 IC50 6.8 6.8 160.0 1
LNCaP
CHEMBL612518
 EC50 6.79 6.79 162.0 1
VCaP
CHEMBL4296508
 EC50 6.79 6.79 160.3 1
LNCaP C4-2B
CHEMBL4296461
 IC50 6.72 6.72 190.0 2
SARS-CoV-2
CHEMBL4303835
 IC50 6.71 6.71 192.8 1
DU-145
CHEMBL613508
 IC50 6.7 5.895 200.0 4
MCF7
CHEMBL387
 IC50 6.7 5.3467 200.0 3
HL-60
CHEMBL383
 EC50 6.7 6.415 200.0 2
MX1
CHEMBL613704
 EC50 6.59 6.59 254.0 1
BCPAP
CHEMBL1075394
 IC50 6.59 6.59 254.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 172.1 - Chlorocebus sabaeus
AUC 3381.8 ng.hr.mL-1 Mus musculus
AUC 75100.0 ng.hr.mL-1 Mus musculus
AUC 41100.0 ng.hr.mL-1 Mus musculus
AUC 914.0 ng.hr.mL-1 Mus musculus
CL 16.6 uL.min-1.(10^6cells)-1 Homo sapiens
CL 78.0 mL.min-1.g-1 Homo sapiens
CL 136.0 mL.min-1.g-1 Homo sapiens
CL 129.0 mL.min-1.g-1 Rattus norvegicus
CL 166.0 mL.min-1.g-1 Mus musculus
Cmax 840.0 nM Mus musculus
T1/2 0.2167 hr Homo sapiens
T1/2 0.2167 hr Rattus norvegicus
T1/2 0.1167 hr Mus musculus
T1/2 0.2 hr Mus musculus
T1/2 0.2333 hr Homo sapiens
T1/2 100.0 hr Homo sapiens
T1/2 0.4 hr Homo sapiens
T1/2 0.8167 hr Homo sapiens
T1/2 3.36 hr Mus musculus
T1/2 1.93 hr Mus musculus
T1/2 0.1833 hr Mus musculus
T1/2 2.3 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Monocyte IC50 = 2.0 nM 8.7 Inhibition of LPS-induced MCP-1 production in mouse Monocyte 38876177
Bromodomain-containing protein 2 IC50 = 3.93 nM 8.41 Inhibition of C-terminal His6-tagged BRD2 BD2 (unknown origin) using H-YSGRGK(Ac... 35333526
Bromodomain-containing protein 4 IC50 = 3.9 nM 8.41 Inhibition of BRD4 BD2 (unknown origin) preincubated for 15 mins followed by pep... 32883643
Bromodomain testis-specific protein IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction (Cell Proliferation (Cell TiterGlo assa... -
Bromodomain-containing protein 4 IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction (Cell Proliferation (Cell TiterGlo assa... -
Bromodomain-containing protein 4 IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction (Cell Proliferation (Cell TiterGlo assa... -
Bromodomain-containing protein 2 IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction (Cell Proliferation (Cell TiterGlo assa... -
Bromodomain-containing protein 2 IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction (Cell Proliferation (Cell TiterGlo assa... -
Bromodomain-containing protein 3 IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction (Cell Proliferation (Cell TiterGlo assa... -
Bromodomain-containing protein 3 IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction (Cell Proliferation (Cell TiterGlo assa... -
Bromodomain testis-specific protein IC50 = 4.0 nM 8.4 Affinity Phenotypic Cellular interaction (Cell Proliferation (Cell TiterGlo assa... -
Bromodomain-containing protein 3 IC50 = 4.87 nM 8.31 Inhibition of C-terminal His6-tagged BRD3 BD2 (unknown origin) using H-YSGRGK(Ac... 35333526
Bromodomain-containing protein 4 IC50 = 5.16 nM 8.29 Binding affinity to human partial length BRD4 BD2 (K333 to E460 residues) expres... 36577036
Bromodomain-containing protein 4 IC50 = 5.31 nM 8.28 Inhibition of C-terminal His6-tagged BRD4 BD2 (unknown origin) using H-YSGRGK(Ac... 35333526
Bromodomain-containing protein 4 Ki = 5.3 nM 8.28 Binding affinity to human BRD4 BD1 (44 to 168 residues) by fluorescence polariza... 30019901
Bromodomain testis-specific protein IC50 = 5.47 nM 8.26 Binding affinity to human partial length BRDT BD2 (K250 to E382 residues) expres... 36577036
Bromodomain-containing protein 4 IC50 = 5.7 nM 8.24 Inhibition of BRD4 BD2 (unknown origin) incubated for 15 mins by TR-FRET assay 38749341
Bromodomain-containing protein 2 Kd = 6.2 nM 8.21 Binding affinity to biotinylated BRD2 BD2 (349 to 460 amino acid residues) (unkn... 26080064
C-C motif chemokine 2 IC50 = 6.31 nM 8.2 Inhibition of MCP-1 in LPS-stimulated human PBMC cells pretreated with compound ... 37736196
Bromodomain-containing protein 3 Ki = 6.6 nM 8.18 Displacement of FAM-labeled ZBA248 from BRD3 BD1 (24 to 144 amino acid residues)... 26080064

Literature References

PubMed DOI Target Context # Activities
24796395 10.18632/oncotarget.1659 Bromodomain-containing protein 4 1419
- 10.6019/CHEMBL4689842 U2OS 262
- 10.6019/CHEMBL4689842 Fibroblast 261
- 10.6019/CHEMBL4689842 HEK-293T 260
27607580 10.1038/cddis.2016.271 Unchecked 67
31937753 10.1038/s41467-019-14083-4 MDA-MB-231 51
35091172 10.1016/j.ejmech.2022.114116 Unchecked 42
37992518 10.1016/j.ejmech.2023.115924 MV4-11 37
31937753 10.1038/s41467-019-14083-4 BT-549 37
27607580 10.1038/cddis.2016.271 A549 35
27607580 10.1038/cddis.2016.271 NCI-H1373 33
34813314 10.1021/acs.jmedchem.1c01535 SW1990 27
31476112 10.15252/emmm.201809930 Breast cancer cell line 26
31734632 10.1016/j.neo.2019.10.003 Bromodomain-containing protein 4 26
24231268 10.18632/oncotarget.1534 Bromodomain-containing protein 4 26
24973920 10.1038/nm.3613 Unchecked 24
34982556 10.1021/acs.jmedchem.1c01851 Bromodomain-containing protein 4 23
34813314 10.1021/acs.jmedchem.1c01535 Unchecked 22
35091172 10.1016/j.ejmech.2022.114116 SW1990 22
27607580 10.1038/cddis.2016.271 NCI-H460 21

Data from ChEMBL 36 via Core Engine