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Compound Detail

CHEMBL5183440

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COc1ccc(N(C)c2cc(C#N)nc3ccccc23)cc1/C=C/C(=O)NO
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL5183440
Phase Preclinical
Structure Type MOL
InChI Key QHXOKFICRLZQNX-JXMROGBWSA-N
13
Targets
14
Activities
1
Assay Types
4
PK Parameters
16
Publications
0
Known Names

Molecular Properties

374.4
MW (Da)
3.40
ALogP
6
HBA
2
HBD
98.5
PSA (Ų)
0.40
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H18N4O3
MW 374.40
Aromatic Rings 3
Heavy Atoms 28
NP-Likeness -0.67

Activity Summary

IC50 14 meas. best 10.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NCI-N87
CHEMBL614197
 IC50 10.0 10.0 0.1 1
K562
CHEMBL385
 IC50 9.46 9.355 0.3 2
SK-OV-3
CHEMBL614925
 IC50 9.22 9.22 0.6 1
HT-29
CHEMBL384
 IC50 9.21 9.21 0.6 1
MDA-MB-231
CHEMBL400
 IC50 9.15 9.15 0.7 1
MCF7
CHEMBL387
 IC50 9.11 9.11 0.8 1
A549
CHEMBL392
 IC50 9.08 9.08 0.8 1
MIA PaCa-2
CHEMBL614725
 IC50 9.03 9.03 0.9 1
Unchecked
CHEMBL612545
 IC50 8.56 8.56 2.8 1
Tubulin
CHEMBL2095182
 IC50 7.7 7.7 20.0 1
Histone deacetylase 8
CHEMBL3192
 IC50 6.82 6.82 150.0 1
Histone deacetylase 6
CHEMBL1865
 IC50 6.0 6.0 1000.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 5.72 5.72 1900.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.75 mL.min-1.g-1 Rattus norvegicus
CL 0.36 mL.min-1.g-1 Homo sapiens
T1/2 6.6 hr Rattus norvegicus
T1/2 32.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NCI-N87 IC50 = 0.1 nM 10.0 Antiproliferative activity against human NCI-N87 cells after 72 hrs by CellTiter... 35797900
K562 IC50 = 0.35 nM 9.46 Antiproliferative activity against human K562 cells after 72 hrs by CellTiter Gl... 35797900
K562 IC50 = 0.56 nM 9.25 Antiproliferative activity against imatinib-resistant human K562 cells over expr... 35797900
SK-OV-3 IC50 = 0.6 nM 9.22 Antiproliferative activity against human SK-OV-3 cells after 72 hrs by CellTiter... 35797900
HT-29 IC50 = 0.62 nM 9.21 Antiproliferative activity against human HT-29 cells after 72 hrs by CellTiter G... 35797900
MDA-MB-231 IC50 = 0.7 nM 9.15 Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by CellTi... 35797900
MCF7 IC50 = 0.78 nM 9.11 Antiproliferative activity against human MCF7 cells after 72 hrs by CellTiter Gl... 35797900
A549 IC50 = 0.84 nM 9.08 Antiproliferative activity against human A549 cells after 72 hrs by CellTiter Gl... 35797900
MIA PaCa-2 IC50 = 0.94 nM 9.03 Antiproliferative activity against human MIA PaCa-2 cells after 72 hrs by CellTi... 35797900
Unchecked IC50 = 2.78 nM 8.56 Antiproliferative activity against mouse MCA-205 cells after 72 hrs by CellTiter... 35797900
Tubulin IC50 = 20.0 nM 7.7 Inhibition of tubulin polymerization in human HeLa cells assessed as microtubule... 35797900
Histone deacetylase 8 IC50 = 150.0 nM 6.82 Inhibition of HDAC8 (unknown origin) measured by fluorometry assay 35797900
Histone deacetylase 6 IC50 = 1000.0 nM 6.0 Inhibition of HDAC6 (unknown origin) measured by fluorometry assay 35797900
Histone deacetylase 11 IC50 = 1900.0 nM 5.72 Inhibition of HDAC11 (unknown origin) measured by fluorometry assay 35797900

Literature References

PubMed DOI Target Context # Activities
35797900 10.1016/j.ejmech.2022.114573 Unchecked 7
35797900 10.1016/j.ejmech.2022.114573 HT-29 5
35797900 10.1016/j.ejmech.2022.114573 ADMET 5
35797900 10.1016/j.ejmech.2022.114573 Tubulin 4
35797900 10.1016/j.ejmech.2022.114573 K562 2
35797900 10.1016/j.ejmech.2022.114573 Histone deacetylase 8 2
35797900 10.1016/j.ejmech.2022.114573 NCI-N87 1
35797900 10.1016/j.ejmech.2022.114573 HCT-116 1
35797900 10.1016/j.ejmech.2022.114573 MIA PaCa-2 1
35797900 10.1016/j.ejmech.2022.114573 SK-OV-3 1
35797900 10.1016/j.ejmech.2022.114573 A549 1
35797900 10.1016/j.ejmech.2022.114573 MCF7 1
35797900 10.1016/j.ejmech.2022.114573 MDA-MB-231 1
35797900 10.1016/j.ejmech.2022.114573 Histone deacetylase 6 1
35797900 10.1016/j.ejmech.2022.114573 Histone deacetylase 11 1
35797900 10.1016/j.ejmech.2022.114573 No relevant target 1

Data from ChEMBL 36 via Core Engine