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Compound Detail

CHEMBL4542119

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C=C(c1ccc(OC)c(/C=C/C(=O)NO)c1)c1cc(OC)c(OC)c(OC)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4542119
Phase Preclinical
Structure Type MOL
InChI Key YYPHEUCEVKWVAC-VQHVLOKHSA-N
14
Targets
19
Activities
1
Assay Types
4
PK Parameters
20
Publications
0
Known Names

Molecular Properties

385.4
MW (Da)
3.30
ALogP
6
HBA
2
HBD
86.2
PSA (Ų)
0.41
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H23NO6
MW 385.42
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness 0.21

Activity Summary

IC50 19 meas. best 8.85

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
K562
CHEMBL385
 IC50 8.85 8.825 1.4 2
HCT-116
CHEMBL394
 IC50 8.82 8.82 1.5 1
HT-29
CHEMBL384
 IC50 8.7 8.7 2.0 1
A549
CHEMBL392
 IC50 8.7 8.7 2.0 1
MCF7
CHEMBL387
 IC50 8.66 8.66 2.2 1
NCI-N87
CHEMBL614197
 IC50 8.49 8.49 3.2 1
SK-OV-3
CHEMBL614925
 IC50 8.4 8.4 4.0 1
MDA-MB-231
CHEMBL400
 IC50 8.34 8.34 4.6 1
MIA PaCa-2
CHEMBL614725
 IC50 8.22 8.22 6.0 1
Unchecked
CHEMBL612545
 IC50 8.0 6.9 10.0 2
Histone deacetylase 8
CHEMBL3192
 IC50 6.47 6.47 340.0 2
PBL
CHEMBL614233
 IC50 5.16 5.16 7000.0 1
Histone deacetylase 11
CHEMBL3310
 IC50 5.0 5.0 10000.0 2
Histone deacetylase 6
CHEMBL1865
 IC50 4.82 4.82 15000.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 2.57 mL.min-1.g-1 Rattus norvegicus
CL 0.83 mL.min-1.g-1 Homo sapiens
T1/2 4.42 hr Rattus norvegicus
T1/2 14.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
K562 IC50 = 1.4 nM 8.85 Antiproliferative activity against imatinib-resistant human K562 cells over expr... 35797900
HCT-116 IC50 = 1.5 nM 8.82 Antiproliferative activity against human HCT-116 cells after 72 hrs by CellTiter... 35797900
K562 IC50 = 1.6 nM 8.8 Antiproliferative activity against human K562 cells after 72 hrs by CellTiter Gl... 35797900
A549 IC50 = 2.0 nM 8.7 Antiproliferative activity against human A549 cells after 72 hrs by CellTiter Gl... 35797900
HT-29 IC50 = 2.0 nM 8.7 Antiproliferative activity against human HT-29 cells after 72 hrs by CellTiter G... 35797900
MCF7 IC50 = 2.2 nM 8.66 Antiproliferative activity against human MCF7 cells after 72 hrs by CellTiter Gl... 35797900
NCI-N87 IC50 = 3.2 nM 8.49 Antiproliferative activity against human NCI-N87 cells after 72 hrs by CellTiter... 35797900
SK-OV-3 IC50 = 4.0 nM 8.4 Antiproliferative activity against human SK-OV-3 cells after 72 hrs by CellTiter... 35797900
MDA-MB-231 IC50 = 4.6 nM 8.34 Antiproliferative activity against human MDA-MB-231 cells after 72 hrs by CellTi... 35797900
MIA PaCa-2 IC50 = 6.0 nM 8.22 Antiproliferative activity against human MIA PaCa-2 cells after 72 hrs by CellTi... 35797900
Unchecked IC50 = 10.0 nM 8.0 Antiproliferative activity against human BL2 cells after 72 hrs by MTS assay 30004697
Histone deacetylase 8 IC50 = 340.0 nM 6.47 Inhibition of human recombinant HDAC8 after 30 mins using fluorogenic substrate ... 30004697
Histone deacetylase 8 IC50 = 340.0 nM 6.47 Inhibition of HDAC8 (unknown origin) measured by fluorometry assay 35797900
Unchecked IC50 = 1600.0 nM 5.8 Inhibition of sheep brain tubulin polymerization assessed as reduction in rate o... 30004697
PBL IC50 = 7000.0 nM 5.16 Cytotoxicity against human PBL cells assessed as cell growth inhibition after 72... 30004697
Histone deacetylase 11 IC50 = 10000.0 nM 5.0 Inhibition of human recombinant HDAC11 after 30 mins using fluorogenic substrate... 30004697
Histone deacetylase 11 IC50 = 10000.0 nM 5.0 Inhibition of HDAC11 (unknown origin) measured by fluorometry assay 35797900
Histone deacetylase 6 IC50 = 15000.0 nM 4.82 Inhibition of human recombinant HDAC6 after 30 mins using fluorogenic substrate ... 30004697
Histone deacetylase 6 IC50 = 15000.0 nM 4.82 Inhibition of HDAC6 (unknown origin) measured by fluorometry assay 35797900

Literature References

PubMed DOI Target Context # Activities
30004697 10.1021/acs.jmedchem.8b00050 Unchecked 5
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 8 4
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 6 4
35797900 10.1016/j.ejmech.2022.114573 ADMET 4
30004697 10.1021/acs.jmedchem.8b00050 HT-29 3
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 3
30004697 10.1021/acs.jmedchem.8b00050 Tubulin 3
30004697 10.1021/acs.jmedchem.8b00050 U-87 MG 3
30004697 10.1021/acs.jmedchem.8b00050 K-562R 3
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 11 2
30004697 10.1021/acs.jmedchem.8b00050 No relevant target 2
30004697 10.1021/acs.jmedchem.8b00050 K562 2
35797900 10.1016/j.ejmech.2022.114573 K562 2
30004697 10.1021/acs.jmedchem.8b00050 HCT-116 2
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 5 1
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 9 1
30004697 10.1021/acs.jmedchem.8b00050 Polyamine deacetylase HDAC10 1
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 4 1
30004697 10.1021/acs.jmedchem.8b00050 PC-3 1
30004697 10.1021/acs.jmedchem.8b00050 Histone deacetylase 3 1

Data from ChEMBL 36 via Core Engine