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Compound Detail

CHEMBL1231206

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Cc1ccc(-c2ccc3c(ccc4sc5c(c43)NC[C@@H](C)NC5=O)n2)cn1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1231206
Phase Preclinical
Structure Type MOL
InChI Key CMWRPDHVGMHLSZ-GFCCVEGCSA-N
25
Targets
100
Activities
3
Assay Types
14
PK Parameters
20
Publications
0
Known Names

Molecular Properties

374.5
MW (Da)
4.36
ALogP
5
HBA
2
HBD
66.9
PSA (Ų)
0.52
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C21H18N4OS
MW 374.47
Aromatic Rings 4
Heavy Atoms 27
NP-Likeness -0.72

Activity Summary

IC50 97 meas. best 8.7
Ki 2 meas. best 8.52
Kd 1 meas. best 8.23

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
MAP kinase-activated protein kinase 2
CHEMBL2208
 IC50 8.7 7.194 2.0 15
MAP kinase-activated protein kinase 2
CHEMBL2208
 Ki 8.52 8.41 3.0 2
MAP kinase-activated protein kinase 5
CHEMBL3094
 IC50 8.3 7.074 5.0 10
MAP kinase-activated protein kinase 2
CHEMBL2208
 Kd 8.23 8.23 5.9 1
MAP kinase-activated protein kinase 3
CHEMBL4670
 IC50 7.28 6.666 53.0 10
Mitogen-activated protein kinase kinase kinase 5
CHEMBL5285
 IC50 7.22 7.22 60.0 3
Unchecked
CHEMBL612545
 IC50 7.16 5.9363 70.0 19
Calcium/calmodulin-dependent protein kinase type II subunit beta
CHEMBL4121
 IC50 7.16 7.16 70.0 1
Calcium/calmodulin-dependent protein kinase type II subunit alpha
CHEMBL4147
 IC50 7.16 7.16 70.0 1
Serine/threonine-protein kinase 17A
CHEMBL4525
 IC50 7.15 7.15 71.0 3
Tyrosine-protein kinase Mer
CHEMBL5331
 IC50 7.12 7.12 76.0 3
Serine/threonine-protein kinase pim-1
CHEMBL2147
 IC50 7.06 7.06 88.0 3
Serine/threonine-protein kinase BRSK2
CHEMBL4574
 IC50 7.05 7.05 90.0 3
5'-AMP-activated protein kinase catalytic subunit alpha-1
CHEMBL4045
 IC50 6.93 6.93 117.0 2
MAP kinase-interacting serine/threonine-protein kinase 2
CHEMBL4204
 IC50 6.83 6.83 148.0 3
U-937
CHEMBL612794
 IC50 6.82 6.82 150.0 1
Serine/threonine-protein kinase BRSK1
CHEMBL5650
 IC50 6.73 6.73 187.0 3
Cyclin-dependent kinase 1
CHEMBL308
 IC50 6.45 6.45 354.0 1
Cyclin-dependent kinase 1/cyclin B
CHEMBL2094127
 IC50 6.45 6.45 354.0 1
Cyclin-dependent kinase 1/cyclin B1
CHEMBL1907602
 IC50 6.45 6.45 354.0 1
Tyrosine-protein kinase receptor UFO
CHEMBL4895
 IC50 6.37 6.37 428.0 3
Phosphorylase b kinase gamma catalytic chain, liver/testis isoform
CHEMBL2349
 IC50 6.28 6.28 528.0 3
Receptor-interacting serine/threonine-protein kinase 2
CHEMBL5014
 IC50 6.23 6.23 590.0 3
Cyclin-dependent kinase 5
CHEMBL4036
 IC50 6.04 6.04 902.0 1
Cyclin-dependent kinase 5/CDK5 activator 1
CHEMBL1907600
 IC50 6.04 6.04 902.0 2
MAP kinase-interacting serine/threonine-protein kinase 1
CHEMBL4718
 IC50 5.52 5.52 3000.0 1
Bile salt export pump
CHEMBL6020
 IC50 5.16 5.16 7000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 43812.99 ng.hr.mL-1 Rattus norvegicus
AUC 12731.98 ng.hr.mL-1 Rattus norvegicus
AUC 674.05 ng.hr.mL-1 Rattus norvegicus
CL 6.92 uL.min-1.(10^6cells)-1 Homo sapiens
CL 10.33 mL.min-1.kg-1 Rattus norvegicus
Cmax 28000.0 nM Rattus norvegicus
Cmax 11000.0 nM Rattus norvegicus
Cmax 660.0 nM Rattus norvegicus
F 46.0 % Rattus norvegicus
T1/2 9.0 hr Rattus norvegicus
T1/2 0.04056 hr Homo sapiens
T1/2 9.1 hr Rattus norvegicus
Tmax 0.1667 hr Rattus norvegicus
Tmax 0.17 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
MAP kinase-activated protein kinase 2 IC50 = 2.0 nM 8.7 Inhibition of human MK2 33481605
MAP kinase-activated protein kinase 2 Ki = 3.0 nM 8.52 Binding affinity to recombinant N-terminal truncated MK2 (45 to 371 residues) (u... 20237073
MAP kinase-activated protein kinase 2 Ki = 5.0 nM 8.3 Inhibition of recombinant MK2 (45 to 400 residues) (unknown origin) using fluore... 28280261
MAP kinase-activated protein kinase 5 IC50 = 5.0 nM 8.3 Inhibition of recombinant PRAK (unknown origin) expressed in Escherichia coli us... 20237073
MAP kinase-activated protein kinase 5 IC50 = 5.0 nM 8.3 Selectivity interaction (Upstate Kinase Profiler service (Millipore, enzymatic a... -
MAP kinase-activated protein kinase 5 IC50 = 5.0 nM 8.3 Affinity Biochemical interaction: (Enzymatic activity assay (Ustate kinase profi... -
MAP kinase-activated protein kinase 2 IC50 = 5.0 nM 8.3 Affinity Biochemical interaction (Enzymatic activity assay (Ustate kinase profil... -
MAP kinase-activated protein kinase 5 IC50 = 5.0 nM 8.3 Affinity Biochemical interaction (Enzymatic activity assay (Ustate kinase profil... -
MAP kinase-activated protein kinase 2 IC50 = 5.0 nM 8.3 Affinity Biochemical interaction: (Enzymatic activity assay (Ustate kinase profi... -
MAP kinase-activated protein kinase 2 IC50 = 5.0 nM 8.3 Binding affinity to recombinant MAPKAP-K2 using KKKALSRQLSVAA as substrate after... 22746295
MAP kinase-activated protein kinase 2 IC50 = 5.0 nM 8.3 Selectivity interaction (Upstate Kinase Profiler service (Millipore, enzymatic a... -
MAP kinase-activated protein kinase 2 IC50 = 5.2 nM 8.28 Inhibition of recombinant N-terminal truncated MK2 (45 to 371 residues) (unknown... 20237073
MAP kinase-activated protein kinase 2 Kd = 5.9 nM 8.23 Binding affinity to recombinant N-terminal truncated MK2 (45 to 371 residues) (u... 20237073
MAP kinase-activated protein kinase 3 IC50 = 53.0 nM 7.28 Affinity Biochemical interaction (Enzymatic activity assay (Ustate kinase profil... -
MAP kinase-activated protein kinase 3 IC50 = 53.0 nM 7.28 Affinity Biochemical interaction: (Enzymatic activity assay (Ustate kinase profi... -
MAP kinase-activated protein kinase 3 IC50 = 53.0 nM 7.28 Selectivity interaction (Upstate Kinase Profiler service (Millipore, enzymatic a... -
MAP kinase-activated protein kinase 3 IC50 = 53.0 nM 7.28 Inhibition of recombinant MK3 (unknown origin) expressed in Escherichia coli usi... 20237073
Mitogen-activated protein kinase kinase kinase 5 IC50 = 60.0 nM 7.22 Selectivity interaction (Upstate Kinase Profiler service (Millipore, enzymatic a... -
Mitogen-activated protein kinase kinase kinase 5 IC50 = 60.0 nM 7.22 Selectivity interaction (Upstate Kinase Profiler service (Millipore)) EUB0000056... -
Mitogen-activated protein kinase kinase kinase 5 IC50 = 60.0 nM 7.22 Inhibition of ASK1 (unknown origin) 20237073

Literature References

PubMed DOI Target Context # Activities
20237073 10.1124/jpet.110.166173 Unchecked 44
20237073 10.1124/jpet.110.166173 ADMET 19
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL5724696 U2OS 8
20237073 10.1124/jpet.110.166173 MAP kinase-activated protein kinase 2 8
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.6019/CHEMBL5444388 MAP kinase-activated protein kinase 2 5
- 10.6019/CHEMBL5444388 MAP kinase-activated protein kinase 3 5
- 10.6019/CHEMBL5444388 MAP kinase-activated protein kinase 5 5
- 10.6019/CHEMBL4689842 U2OS 5
- 10.6019/CHEMBL3301361 ADMET 4
26502061 10.1021/acs.jmedchem.5b01457 Rattus norvegicus 4
20237073 10.1124/jpet.110.166173 Rattus norvegicus 4
- 10.6019/CHEMBL4689842 HEK-293T 3
- 10.6019/CHEMBL4689842 Fibroblast 2
- 10.6019/CHEMBL5465560 Phosphorylase b kinase gamma catalytic chain, liver/testis isoform 2
- 10.6019/CHEMBL5465560 Serine/threonine-protein kinase pim-1 2
- 10.6019/CHEMBL5465560 MAP kinase-interacting serine/threonine-protein kinase 2 2
26502061 10.1021/acs.jmedchem.5b01457 Canis familiaris 2

Data from ChEMBL 36 via Core Engine