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Compound Detail

CHEMBL560141

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CCOC(=O)CC1C(C(=O)OCC)=C(N)Oc2ccc(-c3ccccc3)cc21
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL560141
Phase Preclinical
Structure Type MOL
InChI Key SKRXDYLNZWOTRL-UHFFFAOYSA-N
12
Targets
17
Activities
2
Assay Types
1
PK Parameters
17
Publications
0
Known Names

Molecular Properties

381.4
MW (Da)
3.52
ALogP
6
HBA
1
HBD
87.8
PSA (Ų)
0.77
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H23NO5
MW 381.43
Aromatic Rings 2
Heavy Atoms 28
NP-Likeness -0.21

Activity Summary

IC50 16 meas. best 4.83
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DU-145
CHEMBL613508
 IC50 4.83 4.83 14730.0 1
NCI-H460
CHEMBL396
 IC50 4.81 4.81 15530.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 4.73 4.6667 18690.0 3
HCT-116
CHEMBL394
 IC50 4.73 4.73 18490.0 1
MCF7
CHEMBL387
 IC50 4.72 4.72 18870.0 1
REH
CHEMBL2366320
 IC50 4.7 4.7 20180.0 1
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1
CHEMBL4693
 IC50 4.64 4.64 23000.0 1
Unchecked
CHEMBL612545
 IC50 4.64 4.64 23000.0 1
Jurkat
CHEMBL397
 IC50 4.57 4.57 27200.0 2
RPMI-8226
CHEMBL614882
 IC50 4.57 4.57 27200.0 1
NALM-6
CHEMBL614187
 IC50 4.36 4.36 44200.0 1
HL-60
CHEMBL383
 IC50 4.04 4.04 91000.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 24.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DU-145 IC50 = 14730.0 nM 4.83 Cytotoxicity against human DU145 cells after 48 hrs by cell titer-blue assay 19743858
NCI-H460 IC50 = 15530.0 nM 4.81 Cytotoxicity against human H460 cells after 48 hrs by cell titer-blue assay 19743858
NON-PROTEIN TARGET IC50 = 18690.0 nM 4.73 Cytotoxicity against human SU-8686 cells after 48 hrs by cell titer-blue assay 19743858
HCT-116 IC50 = 18490.0 nM 4.73 Cytotoxicity against human HCT116 cells after 48 hrs by cell titer-blue assay 19743858
MCF7 IC50 = 18870.0 nM 4.72 Cytotoxicity against human MCF7 cells after 48 hrs by cell titer-blue assay 19743858
REH IC50 = 20180.0 nM 4.7 Cytotoxicity against human REH cells after 48 hrs by cell titer-blue assay 19743858
NON-PROTEIN TARGET IC50 = 22780.0 nM 4.64 Cytotoxicity against mouse Hepa-1c1c7 cells after 48 hrs by cell titer-blue assa... 19743858
Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 IC50 = 23000.0 nM 4.64 Inhibition of rabbit skeletal muscle microsomes SERCA1a by enzyme-coupled method 32030976
Unchecked IC50 = 23000.0 nM 4.64 Inhibition of porcine cerebellar microsomes SERCA2b by enzyme-coupled method 32030976
NON-PROTEIN TARGET IC50 = 23200.0 nM 4.63 Cytotoxicity against human HL60/MX2 cells after 48 hrs by CellTiter-Blue cell vi... 21780800
Jurkat IC50 = 27200.0 nM 4.57 Cytotoxicity against human Jurkat cells after 48 hrs by cell titer-blue assay 19743858
RPMI-8226 IC50 = 27200.0 nM 4.57 Cytotoxicity against human RPMI-8226 cells assessed as reduction in cell viabili... 37690265
Jurkat IC50 = 27200.0 nM 4.57 Antiproliferative activity against human Jurkat cells assessed as reduction in c... 37690265
NALM-6 IC50 = 44200.0 nM 4.36 Cytotoxicity against human NALM6 cells after 48 hrs by cell titer-blue assay 19743858
HL-60 IC50 = 91000.0 nM 4.04 Cytotoxicity against human HL60 cells after 48 hrs by CellTiter-Blue cell viabil... 21780800
HL-60 IC50 = 91000.0 nM 4.04 Cytotoxicity against human HL60 cells assessed as cell viability after 48 hrs by... 22582991

Literature References

PubMed DOI Target Context # Activities
19743858 10.1021/jm9005059 NALM-6 3
19743858 10.1021/jm9005059 NON-PROTEIN TARGET 2
21780800 10.1021/jm200764t HL-60 2
37690265 10.1016/j.ejmech.2023.115792 ADMET 1
19743858 10.1021/jm9005059 Jurkat 1
37690265 10.1016/j.ejmech.2023.115792 Jurkat 1
37690265 10.1016/j.ejmech.2023.115792 RPMI-8226 1
32030976 10.1021/acs.jmedchem.9b01509 Unchecked 1
32030976 10.1021/acs.jmedchem.9b01509 Sarcoplasmic/endoplasmic reticulum calcium ATPase 1 1
22582991 10.1021/jm300515q HL-60 1
21780800 10.1021/jm200764t NON-PROTEIN TARGET 1
19743858 10.1021/jm9005059 Bcl-2-like protein 1 1
19743858 10.1021/jm9005059 DU-145 1
19743858 10.1021/jm9005059 NCI-H460 1
19743858 10.1021/jm9005059 HCT-116 1
19743858 10.1021/jm9005059 MCF7 1
19743858 10.1021/jm9005059 REH 1

Data from ChEMBL 36 via Core Engine