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Compound Detail

CHEMBL4790618

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CCCCN(Cc1ccccc1)C(=O)c1ccc(S(=O)(=O)Nc2ccccc2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4790618
Phase Preclinical
Structure Type MOL
InChI Key VNCIWNGCMAKKEO-UHFFFAOYSA-N
3
Targets
24
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

422.6
MW (Da)
4.93
ALogP
3
HBA
1
HBD
66.5
PSA (Ų)
0.53
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C24H26N2O3S
MW 422.55
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.65

Activity Summary

IC50 18 meas. best 7.84
Kd 6 meas. best 7.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
LIM domain kinase 2
CHEMBL5932
 IC50 7.84 7.2125 14.4 8
LIM domain kinase 1
CHEMBL3836
 Kd 7.19 6.8 64.0 4
LIM domain kinase 2
CHEMBL5932
 Kd 7.19 6.485 64.0 2
LIM domain kinase 1
CHEMBL3836
 IC50 7.08 6.6233 83.8 9
LIM domain kinase 1/2
CHEMBL3885599
 IC50 6.59 6.59 257.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 500.0 mL.min-1.g-1 Rattus norvegicus
CL 450.0 mL.min-1.g-1 Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
LIM domain kinase 2 IC50 = 14.45 nM 7.84 Inhibition of recombinant LIMK2 (347 to 659 residues) (unknown origin) incubated... 36205722
LIM domain kinase 2 IC50 = 15.5 nM 7.81 Inhibition of recombinant LIMK2 (330 to 632 residues) (unknown origin) expressed... 36136092
LIM domain kinase 2 IC50 = 15.49 nM 7.81 Inhibition of PAK mediated recombinant LIMK2 phosphorylation (347 to 659 residue... 36205722
LIM domain kinase 2 IC50 = 15.5 nM 7.81 Affinity Biochemical interaction (RapidFire MS assay) EUB0000232b LIMK2 -
LIM domain kinase 1 Kd = 64.0 nM 7.19 Binding affinity to recombinant LIMK1 (330 to 637 residues) (unknown origin) exp... 36136092
LIM domain kinase 2 Kd = 64.0 nM 7.19 Binding affinity to human wild-type full length LIMK2 (M1 to P638 residues) expr... 36136092
LIM domain kinase 1 IC50 = 83.8 nM 7.08 Affinity Biochemical interaction (RapidFire MS assay) EUB0000232b LIMK1 -
LIM domain kinase 1 IC50 = 83.8 nM 7.08 Inhibition of recombinant LIMK1 (330 to 637 residues) (unknown origin) expressed... 36136092
LIM domain kinase 2 IC50 = 91.0 nM 7.04 Inhibition of recombinant full length LIMK2 (330 to 632 residues) (unknown origi... 36136092
LIM domain kinase 2 IC50 = 91.0 nM 7.04 Affinity On-target Cellular interaction (NanoBRET assay (HEK293T cells)) EUB0000... -
LIM domain kinase 1 Kd = 120.0 nM 6.92 Selectivity interaction (ScanMAX (DiscoverX, competition-binding assay)) EUB0000... -
LIM domain kinase 1 Kd = 120.0 nM 6.92 Binding affinity to human wild-type full length LIMK1 (M1 to D647 residues) expr... 36136092
LIM domain kinase 2 IC50 = 190.55 nM 6.72 Inhibition of recombinant LIMK2(unknown origin) expressed in HEK293 cells using ... 36205722
LIM domain kinase 1 IC50 = 194.98 nM 6.71 Inhibition of PAK mediated recombinant LIMK1 phosphorylation (330 to 637 residue... 36205722
LIM domain kinase 1 IC50 = 199.53 nM 6.7 Inhibition of recombinant LIMK1 (330 to 637 residues) (unknown origin) incubated... 36205722
LIM domain kinase 1 IC50 = 229.09 nM 6.64 Inhibition of recombinant LIMK1(unknown origin) expressed in HEK293 cells using ... 36205722
LIM domain kinase 1 IC50 = 238.0 nM 6.62 Inhibition of recombinant full length LIMK1 (330 to 637 residues) (unknown origi... 36136092
LIM domain kinase 1 IC50 = 238.0 nM 6.62 Affinity On-target Cellular interaction (NanoBRET assay (HEK293T cells)) EUB0000... -
LIM domain kinase 1/2 IC50 = 257.04 nM 6.59 Inhibition of LIMK1/LIMK2 in human SH-SY5Y cells assessed as effect on phospho c... 36205722
LIM domain kinase 1 Kd = 682.0 nM 6.17 Binding affinity to LIMK1 in human HeLa cells assessed as apparent dissociation ... 36136092

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL4689842 Fibroblast 9
- 10.6019/CHEMBL5724696 U2OS 8
- 10.6019/CHEMBL4689842 U2OS 7
36136092 10.1021/acs.jmedchem.2c01106 LIM domain kinase 1 7
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.6019/CHEMBL4689842 HEK-293T 6
36136092 10.1021/acs.jmedchem.2c01106 LIM domain kinase 2 6
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
- 10.6019/CHEMBL5212743 Epidermal growth factor receptor 4
- 10.6019/CHEMBL5212743 LIM domain kinase 1 3
36205722 10.1021/acs.jmedchem.2c00751 LIM domain kinase 2 3
36205722 10.1021/acs.jmedchem.2c00751 LIM domain kinase 1 3
36136092 10.1021/acs.jmedchem.2c01106 HeLa 3
36205722 10.1021/acs.jmedchem.2c00751 ADMET 2
- 10.6019/CHEMBL5212743 Tyrosine-protein kinase SYK 2
- 10.6019/CHEMBL5212743 Tyrosine-protein kinase Lck 2
- 10.6019/CHEMBL5212743 STE20-like serine/threonine-protein kinase 2
- 10.1021/acschembio.2c00877 Colon organoid 1

Data from ChEMBL 36 via Core Engine