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Compound Detail

CHEMBL4094346

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Cc1sc2c(c1C)C(c1ccc(Cl)cc1)=N[C@@H](CC(=O)NCCCCNC(=O)COc1cccc3c1C(=O)N(C1CCC(=O)NC1=O)C3=O)c1nnc(C)n1-2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4094346
Phase Preclinical
Structure Type MOL
InChI Key LKEGXJXRNBALBV-PMCHYTPCSA-N
17
Targets
27
Activities
4
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

785.3
MW (Da)
3.68
ALogP
12
HBA
3
HBD
194.1
PSA (Ų)
0.14
QED
2
Ro5 Violations
12
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C38H37ClN8O7S
MW 785.28
Aromatic Rings 4
Heavy Atoms 55
NP-Likeness -0.93

Activity Summary

IC50 22 meas. best 8.51
EC50 2 meas. best 8.28
Ki 2 meas. best 8.28
Kd 1 meas. best 8.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Protein cereblon/DNA damage-binding protein 1
CHEMBL4630734
 IC50 8.51 8.51 3.1 1
Bromodomain-containing protein 3
CHEMBL1795186
 Ki 8.28 8.21 5.3 2
Protein cereblon/Bromodomain-containing protein 4
CHEMBL4296138
 EC50 8.28 8.28 5.3 1
Bromodomain testis-specific protein
CHEMBL1795185
 Kd 8.22 8.22 6.0 1
MV4-11
CHEMBL613835
 IC50 8.21 7.8525 6.1 4
Protein cereblon/DNA damage-binding protein 1/Bromodomain-containing protein 4
CHEMBL4296145
 IC50 7.7 7.7 20.0 1
PC-3
CHEMBL390
 EC50 7.3 7.3 50.0 1
HEK293
CHEMBL614818
 IC50 7.25 6.4975 56.0 4
RS4-11
CHEMBL2366159
 IC50 7.1 7.1 78.8 2
MM1.S
CHEMBL4296471
 IC50 6.85 6.23 141.0 2
MOLM-13
CHEMBL3706572
 IC50 6.85 6.515 140.0 2
HGC-27
CHEMBL1075463
 IC50 6.06 6.06 880.0 1
MCF7
CHEMBL387
 IC50 5.28 5.28 5300.0 1
Unchecked
CHEMBL612545
 IC50 5.15 5.15 7070.0 1
A549
CHEMBL392
 IC50 4.91 4.91 12300.0 1
HeLa
CHEMBL399
 IC50 4.79 4.79 16060.0 1
HepG2
CHEMBL395
 IC50 4.7 4.7 19800.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 2.25 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Protein cereblon/DNA damage-binding protein 1 IC50 = 3.09 nM 8.51 CRBN-DDB1 ligand-displacement AlphaScreen Assay: A thalidomide competition Alpha... -
Protein cereblon/Bromodomain-containing protein 4 EC50 = 5.27 nM 8.28 Protac activity at CRBN/BRD4 in human MV4-11 cells assessed as induction of BRD4... 37178483
Bromodomain-containing protein 3 Ki = 5.26 nM 8.28 Binding affinity to recombinant human BRD3 BD2 (306 to 417 residues) assessed as... 37084596
Bromodomain testis-specific protein Kd = 6.0 nM 8.22 Binding affinity to human partial length BRDT bromodomain 1 (N21 to E137 residue... 32019712
MV4-11 IC50 = 6.1 nM 8.21 Antiproliferative activity against human MV4-11 cells assessed as inhibition of ... 37178483
Bromodomain-containing protein 3 Ki = 7.28 nM 8.14 Binding affinity to recombinant human BRD3 BD1 (24 to 144 residues) assessed as ... 37084596
MV4-11 IC50 = 11.8 nM 7.93 Antiproliferative activity against human MV4-11 cells assessed as cell growth in... 37084596
MV4-11 IC50 = 13.0 nM 7.89 Antiproliferative activity against human MM4-11 cells assessed as inhibition of ... 36563515
Protein cereblon/DNA damage-binding protein 1/Bromodomain-containing protein 4 IC50 = 20.0 nM 7.7 CRBN-DDB1/BRD4 Dimerization Assay: AlphaScreen technology was used to detect CRB... -
MV4-11 IC50 = 42.0 nM 7.38 Growth inhibition of human MV4-11 cells after 96 hrs by CCK8 assay 30019901
PC-3 EC50 = 50.0 nM 7.3 Cytotoxicity against human PC-3 cells assessed as reduction in cell viability me... 36577036
HEK293 IC50 = 56.0 nM 7.25 Cytotoxicity against permeabilized HEK293 cells assessed as inhibition of cell v... 35859867
RS4-11 IC50 = 79.0 nM 7.1 Growth inhibition of human RS4:11 cells after 96 hrs by CCK8 assay 30019901
RS4-11 IC50 = 78.8 nM 7.1 Cytotoxicity against human RS4:11 cells assessed as cell growth inhibition after... 28339196
HEK293 IC50 = 90.0 nM 7.05 Cytotoxicity against permeabilized HEK293 cells assessed as inhibition of cell v... 35859867
MOLM-13 IC50 = 140.0 nM 6.85 Growth inhibition of human MOLM13 cells after 96 hrs by CCK8 assay 30019901
MM1.S IC50 = 141.0 nM 6.85 Antiproliferative activity against human MM1.S cells assessed as inhibition of c... 36563515
MOLM-13 IC50 = 657.0 nM 6.18 Cytotoxicity against human MOLM13 cells assessed as cell growth inhibition after... 28339196
HGC-27 IC50 = 880.0 nM 6.06 Antiproliferative activity against human HGC-27 cells assessed as cell growth in... 37084596
HEK293 IC50 = 930.0 nM 6.03 Cytotoxicity against human HEK293 cells assessed as inhibition of cell viability... 35859867

Literature References

PubMed DOI Target Context # Activities
31734632 10.1016/j.neo.2019.10.003 Protein cereblon/Bromodomain-containing protein 4 31
36563515 10.1016/j.bmc.2022.117134 Protein cereblon/Bromodomain-containing protein 4 13
37084596 10.1016/j.ejmech.2023.115381 Protein cereblon/Bromodomain-containing protein 4 10
35859867 10.1021/acsmedchemlett.2c00124 HEK293 8
37084596 10.1016/j.ejmech.2023.115381 Protein cereblon/Bromodomain-containing protein 3 8
34119833 10.1016/j.ejmech.2021.113608 Unchecked 7
33026811 10.1021/acs.jmedchem.0c00793 Unchecked 6
37084596 10.1016/j.ejmech.2023.115381 Protein cereblon/Bromodomain-containing protein 2 5
35859867 10.1021/acsmedchemlett.2c00124 Protein cereblon/Bromodomain-containing protein 4 4
28378579 10.1021/acs.jmedchem.6b01781 No relevant target 3
28378579 10.1021/acs.jmedchem.6b01781 Protein cereblon/DNA damage-binding protein 1/Bromodomain-containing protein 4 3
31734632 10.1016/j.neo.2019.10.003 LS174T 3
34119833 10.1016/j.ejmech.2021.113608 Protein cereblon/Bromodomain-containing protein 4 3
31047748 10.1016/j.bmcl.2019.04.030 Protein cereblon/Bromodomain-containing protein 4 2
32858471 10.1016/j.ejmech.2020.112698 Protein cereblon/Bromodomain-containing protein 4 2
36262390 10.1021/acsmedchemlett.2c00300 Protein cereblon/Bromodomain-containing protein 4 2
36323630 10.1021/acs.jmedchem.2c01218 No relevant target 2
31734632 10.1016/j.neo.2019.10.003 HCT-116 2
37084596 10.1016/j.ejmech.2023.115381 Bromodomain-containing protein 3 2
36788245 10.1021/acs.jmedchem.2c01555 Protein cereblon/Bromodomain-containing protein 4 2

Data from ChEMBL 36 via Core Engine