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Compound Detail

CHEMBL2179387

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COc1ccccc1S(=O)(=O)Nc1ccc2c(c1)CN(C)C(=O)N2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2179387
Phase Preclinical
Structure Type MOL
InChI Key TXZPMHLMPKIUGK-UHFFFAOYSA-N
8
Targets
24
Activities
3
Assay Types
9
PK Parameters
20
Publications
0
Known Names

Molecular Properties

347.4
MW (Da)
2.47
ALogP
4
HBA
2
HBD
87.7
PSA (Ų)
0.89
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C16H17N3O4S
MW 347.40
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness -1.42

Activity Summary

IC50 21 meas. best 7.39
Kd 2 meas. best 6.87
EC50 1 meas. best 5.72

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Bromodomain-containing protein 4
CHEMBL1163125
 IC50 7.39 6.4747 41.0 15
Bromodomain-containing protein 4
CHEMBL1163125
 Kd 6.87 6.87 136.0 1
THP-1
CHEMBL614245
 IC50 6.37 6.37 430.0 1
PBMC
CHEMBL613107
 EC50 5.72 5.72 1890.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 5.66 5.385 2190.0 2
HL-60
CHEMBL383
 IC50 5.4 5.4 3990.0 1
HT-29
CHEMBL384
 IC50 4.83 4.83 14720.0 1
WI-38
CHEMBL614391
 IC50 4.7 4.7 19800.0 1
CREB-binding protein
CHEMBL5747
 Kd 4.31 4.31 49000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 18.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 166.95 nM Mus musculus
F 32.0 % Rattus norvegicus
F 32.0 % Rattus norvegicus
T1/2 2.0 hr Mus musculus
T1/2 2.0 hr Rattus norvegicus
T1/2 1.0 hr Rattus norvegicus
Tmax 1.0 hr Mus musculus
Vd 1.0 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Bromodomain-containing protein 4 IC50 = 41.0 nM 7.39 Displacement of biotinylated acetylated histone H4 peptide from human recombinan... 35318165
Bromodomain-containing protein 4 IC50 = 88.0 nM 7.06 Inhibition of BRD4 BD1 (unknown origin) preincubated for 15 mins followed by pep... 32883643
Bromodomain-containing protein 4 Kd = 136.0 nM 6.87 Binding affinity to first bromodomain of BRD4 (unknown origin) 24090311
Bromodomain-containing protein 4 IC50 = 220.0 nM 6.66 Inhibition of BRD4 isoform 1 by AlphaScreen assay 23095041
Bromodomain-containing protein 4 IC50 = 220.0 nM 6.66 Binding affinity to human BRD4 bromodomain 1 using H4Ac4 peptide by amplified lu... 23517011
Bromodomain-containing protein 4 IC50 = 220.0 nM 6.66 Inhibition of BRD4 (unknown origin) 29764756
Bromodomain-containing protein 4 IC50 = 220.0 nM 6.66 Inhibition of recombinant His-tagged human BRD4 bromodomain 1 expressed in Esche... 29776834
Bromodomain-containing protein 4 IC50 = 220.0 nM 6.66 Inhibition of BRD4 (unknown origin) by Alphascreen assay 29730189
Bromodomain-containing protein 4 IC50 = 220.0 nM 6.66 Inhibition of BRD4 bromodomain (unknown origin) 31421967
Bromodomain-containing protein 4 IC50 = 220.0 nM 6.66 Displacement of acetylated histone H4 peptide from His-tagged recombinant human ... 35318165
Bromodomain-containing protein 4 IC50 = 220.0 nM 6.66 Inhibition of BRD4 (unknown origin) 31759729
Bromodomain-containing protein 4 IC50 = 220.0 nM 6.66 Inhibition of BRD4 BD1 (unknown origin) using biotinylated histone peptide H4 as... 37992518
THP-1 IC50 = 430.0 nM 6.37 Antiinflammatory activity against human THP-1 cells assessed as inhibition of LP... 35318165
Bromodomain-containing protein 4 IC50 = 980.0 nM 6.01 Inhibition of human His-tagged BRD4 BD1 (49 to 170 residues) using H-SGRGK(Ac)GG... 27266999
PBMC EC50 = 1890.0 nM 5.72 Inhibition of LPS-induced IL6 production in human PBMC by ELISA 23095041
Bromodomain-containing protein 4 IC50 = 2000.0 nM 5.7 Inhibition of BRD4 in human HEL cells harboring JAK2 V617F mutant assessed as de... 33062175
NON-PROTEIN TARGET IC50 = 2190.0 nM 5.66 Cytotoxicity against human HL60 cells assessed as decrease in cell viability aft... 27266999
Bromodomain-containing protein 4 IC50 = 2700.0 nM 5.57 Inhibition of BRD4 in human MOLM-14 cells harboring FLT3-ITD mutant assessed as ... 33062175
Bromodomain-containing protein 4 IC50 = 3540.0 nM 5.45 Inhibition of human BRD4 BD2 (342 to 460 residues) at 30 uM preincubated for 30 ... 27266999
HL-60 IC50 = 3990.0 nM 5.4 Antiproliferative activity against human HL60 cells incubated for 72 hrs by CCK8... 32883643

Literature References

PubMed DOI Target Context # Activities
33062175 10.1021/acsmedchemlett.9b00625 Bromodomain-containing protein 4 15
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5303304 Fibroblast 8
23576556 10.1158/0008-5472.CAN-12-3292 Protein polybromo-1 7
33062175 10.1021/acsmedchemlett.9b00625 Unchecked 6
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
- 10.6019/CHEMBL5303304 U2OS 5
23576556 10.1158/0008-5472.CAN-12-3292 Bromodomain-containing protein 4 4
33691794 10.1186/s13148-021-01037-1 A549 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
23095041 10.1021/jm3010515 Rattus norvegicus 4
- 10.6019/CHEMBL5303304 HEK-293T 4
23576556 10.1158/0008-5472.CAN-12-3292 Bromodomain-containing protein 3 4
29776834 10.1016/j.bmc.2018.05.003 Hs-578T 3
29776834 10.1016/j.bmc.2018.05.003 HOP-92 3
29776834 10.1016/j.bmc.2018.05.003 MDA-MB-468 3
29776834 10.1016/j.bmc.2018.05.003 A498 3
23095041 10.1021/jm3010515 Mus musculus 3

Data from ChEMBL 36 via Core Engine