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Compound Detail

CHEMBL5195122

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COc1cc(/C=C2\N=C(Nc3ccccc3)NC2=O)ccc1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5195122
Phase Preclinical
Structure Type MOL
InChI Key UUXDJIVNVOOKFQ-LCYFTJDESA-N
13
Targets
13
Activities
2
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

309.3
MW (Da)
2.34
ALogP
5
HBA
3
HBD
83.0
PSA (Ų)
0.76
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H15N3O3
MW 309.32
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.20

Activity Summary

IC50 12 meas. best 7.68
EC50 1 meas. best 5.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Dual specificity protein kinase CLK1
CHEMBL1075280
 IC50 7.68 7.68 21.0 1
Dual specificity protein kinase CLK4
CHEMBL1075283
 IC50 7.64 7.64 23.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 2
CHEMBL4376
 IC50 7.48 7.48 33.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1B
CHEMBL5543
 IC50 7.21 7.21 62.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL2292
 IC50 7.16 7.16 70.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 3
CHEMBL4575
 IC50 6.92 6.92 120.0 1
Dual specificity protein kinase CLK2
CHEMBL1075281
 IC50 6.85 6.85 140.0 1
Serine/threonine-protein kinase pim-1
CHEMBL2147
 IC50 6.75 6.75 180.0 1
Dual specificity protein kinase CLK3
CHEMBL1075282
 IC50 6.21 6.21 610.0 1
Casein kinase 2
CHEMBL3832943
 IC50 6.21 6.21 620.0 1
Glycogen synthase kinase-3
CHEMBL2366565
 IC50 5.96 5.96 1100.0 1
HT-22
CHEMBL614316
 EC50 5.89 5.89 1280.0 1
Cannabinoid receptor 1
CHEMBL218
 IC50 5.33 5.33 4703.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Dual specificity protein kinase CLK1 IC50 = 21.0 nM 7.68 Inhibition of GST-fused mouse recombinant CLK1 expressed in Escherichia coli usi... 34928152
Dual specificity protein kinase CLK4 IC50 = 23.0 nM 7.64 Inhibition of GST-fused mouse recombinant CLK4 expressed in Escherichia coli usi... 34928152
Dual specificity tyrosine-phosphorylation-regulated kinase 2 IC50 = 33.0 nM 7.48 Inhibition of GST-fused human recombinant DYRK2 expressed in Escherichia coli us... 34928152
Dual specificity tyrosine-phosphorylation-regulated kinase 1B IC50 = 62.0 nM 7.21 Inhibition of GST-fused human recombinant DYRK1B expressed in Escherichia coli u... 34928152
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 70.0 nM 7.16 Inhibition of GST-fused human recombinant DYRK1A expressed in Escherichia coli u... 34928152
Dual specificity tyrosine-phosphorylation-regulated kinase 3 IC50 = 120.0 nM 6.92 Inhibition of GST-fused human recombinant DYRK3 expressed in Escherichia coli us... 34928152
Dual specificity protein kinase CLK2 IC50 = 140.0 nM 6.85 Inhibition of mouse recombinant GST-fused CLK2 expressed in Escherichia coli usi... 34928152
Serine/threonine-protein kinase pim-1 IC50 = 180.0 nM 6.75 Inhibition of human recombinant Pim1 expressed in Escherichia coli using histone... 34928152
Dual specificity protein kinase CLK3 IC50 = 610.0 nM 6.21 Inhibition of GST-fused mouse recombinant CLK3 expressed in Escherichia coli usi... 34928152
Casein kinase 2 IC50 = 620.0 nM 6.21 Inhibition of human recombinant CK2 using RRRDDDSDDD peptide as substrate incuba... 34928152
Glycogen synthase kinase-3 IC50 = 1100.0 nM 5.96 Inhibition of porcine brain GSK-3alpha/beta using YRRAAVPPSPSLSRHSSPHQpSEDEEE as... 34928152
HT-22 EC50 = 1280.0 nM 5.89 Neuroprotective activity against glutamate-induced cell death in mouse HT-22 cel... 34928152
Cannabinoid receptor 1 IC50 = 4703.0 nM 5.33 Antagonist activity at CP-55940-activated CB1 receptor (unknown origin) by beta-... 34928152

Literature References

PubMed DOI Target Context # Activities
34928152 10.1021/acs.jmedchem.1c01141 Unchecked 4
34928152 10.1021/acs.jmedchem.1c01141 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 2
34928152 10.1021/acs.jmedchem.1c01141 Cannabinoid receptor 1 2
34928152 10.1021/acs.jmedchem.1c01141 Glycogen synthase kinase-3 1
34928152 10.1021/acs.jmedchem.1c01141 Dual specificity protein kinase CLK4 1
34928152 10.1021/acs.jmedchem.1c01141 Dual specificity protein kinase CLK3 1
34928152 10.1021/acs.jmedchem.1c01141 Dual specificity protein kinase CLK1 1
34928152 10.1021/acs.jmedchem.1c01141 Dual specificity protein kinase CLK2 1
34928152 10.1021/acs.jmedchem.1c01141 Dual specificity tyrosine-phosphorylation-regulated kinase 1B 1
34928152 10.1021/acs.jmedchem.1c01141 Dual specificity tyrosine-phosphorylation-regulated kinase 2 1
34928152 10.1021/acs.jmedchem.1c01141 Dual specificity tyrosine-phosphorylation-regulated kinase 3 1
34928152 10.1021/acs.jmedchem.1c01141 Serine/threonine-protein kinase pim-1 1
34928152 10.1021/acs.jmedchem.1c01141 Casein kinase 2 1
34928152 10.1021/acs.jmedchem.1c01141 ADMET 1
34928152 10.1021/acs.jmedchem.1c01141 HT-22 1

Data from ChEMBL 36 via Core Engine