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Compound Detail

CHEMBL5181620

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COc1ncc2cc3cnccc3c([N+](=O)[O-])c2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5181620
Phase Preclinical
Structure Type MOL
InChI Key WPPGBVWZGMDXKF-UHFFFAOYSA-N
12
Targets
22
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

256.2
MW (Da)
2.09
ALogP
6
HBA
0
HBD
91.0
PSA (Ų)
0.40
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C12H8N4O3
MW 256.22
Aromatic Rings 3
Heavy Atoms 19
NP-Likeness -0.76

Activity Summary

IC50 12 meas. best 7.3
EC50 10 meas. best 5.5

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Serine/threonine-protein kinase haspin
CHEMBL1075163
 IC50 7.3 7.24 50.0 4
Serine/threonine-protein kinase PLK3
CHEMBL4897
 IC50 6.93 6.93 117.0 1
Serine/threonine-protein kinase PLK2
CHEMBL5938
 IC50 6.9 6.9 125.0 1
Serine/threonine-protein kinase PLK1
CHEMBL3024
 IC50 6.53 6.53 294.0 1
Dual specificity protein kinase CLK1
CHEMBL1075280
 IC50 6.35 6.35 445.0 2
Death-associated protein kinase 3
CHEMBL2468
 IC50 6.24 6.24 578.0 1
Dual specificity tyrosine-phosphorylation-regulated kinase 1A
CHEMBL5508
 IC50 6.04 6.04 917.0 2
TERT-RPE1
CHEMBL615013
 EC50 5.5 5.425 3200.0 2
SH-SY5Y
CHEMBL614910
 EC50 5.37 5.365 4300.0 2
HCT-116
CHEMBL394
 EC50 5.24 5.225 5800.0 2
U2OS
CHEMBL615023
 EC50 5.24 5.235 5800.0 2
HBL-100
CHEMBL614811
 EC50 5.07 5.045 8500.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Serine/threonine-protein kinase haspin IC50 = 50.0 nM 7.3 Inhibition of recombinant human Haspin (470 to 798 residues) expressed in bacter... 35447555
Serine/threonine-protein kinase haspin IC50 = 50.0 nM 7.3 Inhibition of recombinant human Haspin kinase domain (470 to 798 residues) expre... 38320389
Serine/threonine-protein kinase haspin IC50 = 65.8 nM 7.18 Inhibition of recombinant human haspin (470 to 798 residues) expressed in bacter... 39038808
Serine/threonine-protein kinase haspin IC50 = 65.8 nM 7.18 Inhibition of recombinant human HASPIN (470 to 798 residues) expressed in bacter... 35447555
Serine/threonine-protein kinase PLK3 IC50 = 117.0 nM 6.93 Inhibition of human recombinant PLK3 in presence of ATP by kinomescan assay 35447555
Serine/threonine-protein kinase PLK2 IC50 = 125.0 nM 6.9 Inhibition of human PLK2 in presence of ATP by kinomescan assay 35447555
Serine/threonine-protein kinase PLK1 IC50 = 294.0 nM 6.53 Inhibition of human PLK1 in presence of ATP by kinomescan assay 35447555
Dual specificity protein kinase CLK1 IC50 = 445.0 nM 6.35 Inhibition of recombinant mouse CLK1 expressed in bacteria using GRSRSRSRSRSR as... 38320389
Dual specificity protein kinase CLK1 IC50 = 445.0 nM 6.35 Inhibition of recombinant mouse CLK1 expressed in bacteria using GRSRSRSRSRSR as... 35447555
Death-associated protein kinase 3 IC50 = 578.0 nM 6.24 Inhibition of human DAPK3 in presence of ATP by kinomescan assay 35447555
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 917.0 nM 6.04 Inhibition of recombinant rat DYRK1A kinase domain (1 to 499 residues) expressed... 38320389
Dual specificity tyrosine-phosphorylation-regulated kinase 1A IC50 = 917.0 nM 6.04 Inhibition of recombinant rat DYRK1A (1 to 499 residues ) expressed in bacterial... 35447555
TERT-RPE1 EC50 = 3200.0 nM 5.5 Cytotoxicity against human TERT-RPE1 cells assessed as reduction in cell viabili... 35447555
SH-SY5Y EC50 = 4300.0 nM 5.37 Antiproliferative activity against human SH-SY5Y cells assessed as reduction in ... 38320389
SH-SY5Y EC50 = 4400.0 nM 5.36 Cytotoxicity against human SH-SY5Y cells assessed as reduction in cell viability... 35447555
TERT-RPE1 EC50 = 4500.0 nM 5.35 Cytotoxicity against human TERT-RPE1 cells assessed as reduction in cell viabili... 38320389
HCT-116 EC50 = 5800.0 nM 5.24 Antiproliferative activity against human HCT-116 cells assessed as reduction in ... 38320389
U2OS EC50 = 5800.0 nM 5.24 Cytotoxicity against human U2OS cells assessed as reduction in cell viability me... 35447555
U2OS EC50 = 5900.0 nM 5.23 Antiproliferative activity against human U2OS cells assessed as reduction in cel... 38320389
HCT-116 EC50 = 6200.0 nM 5.21 Cytotoxicity against human HCT-116 cells assessed as reduction in cell viability... 35447555

Literature References

PubMed DOI Target Context # Activities
38320389 10.1016/j.bmc.2024.117619 U2OS 7
35447555 10.1016/j.ejmech.2022.114369 Serine/threonine-protein kinase haspin 4
38320389 10.1016/j.bmc.2024.117619 Serine/threonine-protein kinase haspin 4
38320389 10.1016/j.bmc.2024.117619 Dual specificity protein kinase CLK1 3
38320389 10.1016/j.bmc.2024.117619 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 3
38320389 10.1016/j.bmc.2024.117619 Serine/threonine-protein kinase pim-1 2
38320389 10.1016/j.bmc.2024.117619 Casein kinase I isoform epsilon 2
38320389 10.1016/j.bmc.2024.117619 Glycogen synthase kinase-3 beta 2
38320389 10.1016/j.bmc.2024.117619 CDK9/cyclin T1 2
35447555 10.1016/j.ejmech.2022.114369 U2OS 2
35447555 10.1016/j.ejmech.2022.114369 Dual specificity tyrosine-phosphorylation-regulated kinase 1A 2
35447555 10.1016/j.ejmech.2022.114369 HCT-116 2
35447555 10.1016/j.ejmech.2022.114369 Dual specificity protein kinase CLK1 2
38320389 10.1016/j.bmc.2024.117619 Cyclin-dependent kinase 5/CDK5 activator 1 2
35447555 10.1016/j.ejmech.2022.114369 TERT-RPE1 1
39038808 10.1021/acs.jmedchem.4c00718 Serine/threonine-protein kinase haspin 1
35447555 10.1016/j.ejmech.2022.114369 Unchecked 1
35447555 10.1016/j.ejmech.2022.114369 Tyrosine-protein kinase ABL1 1
35447555 10.1016/j.ejmech.2022.114369 Serine/threonine-protein kinase pim-1 1
35447555 10.1016/j.ejmech.2022.114369 Glycogen synthase kinase-3 beta 1

Data from ChEMBL 36 via Core Engine