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Compound Detail

CHEMBL158037

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C=CC(=O)N1C/C(=C\c2ccc([N+](=O)[O-])cc2)C(=O)/C(=C/c2ccc([N+](=O)[O-])cc2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL158037
Phase Preclinical
Structure Type MOL
InChI Key GFARQYQBWJLZMW-JYFOCSDGSA-N
7
Targets
17
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

419.4
MW (Da)
3.57
ALogP
6
HBA
0
HBD
123.7
PSA (Ų)
0.41
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H17N3O6
MW 419.39
Aromatic Rings 2
Heavy Atoms 31
NP-Likeness -0.37

Activity Summary

IC50 15 meas. best 7.3
EC50 2 meas. best 5.98

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
P388
CHEMBL389
 IC50 7.3 6.925 50.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.82 6.82 150.0 2
CCRF-CEM
CHEMBL382
 IC50 6.58 6.57 260.0 3
L1210
CHEMBL386
 IC50 6.55 5.9333 280.0 6
Unchecked
CHEMBL612545
 IC50 6.55 6.55 280.0 1
Caspase-3
CHEMBL2334
 IC50 5.98 5.98 1050.0 1
HCT-116
CHEMBL394
 EC50 5.98 5.98 1050.0 1
Unchecked
CHEMBL612545
 EC50 5.19 5.19 6500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
P388 IC50 = 50.0 nM 7.3 Cytotoxicity against murine P388 cells. 11170648
NON-PROTEIN TARGET IC50 = 150.0 nM 6.82 Cytotoxicity against human Molt 4/C8 cells. 11170648
NON-PROTEIN TARGET IC50 = 150.0 nM 6.82 Cytotoxicity against human Molt4/C8 cells 19819135
CCRF-CEM IC50 = 260.0 nM 6.58 Cytotoxicity against CEM T-lymphocytes. 11170648
CCRF-CEM IC50 = 260.0 nM 6.58 Cytotoxicity against human CEM cells 19819135
P388 IC50 = 280.0 nM 6.55 Antiproliferative activity against mouse P388 cells assessed as cell growth inhi... 32172081
L1210 IC50 = 280.0 nM 6.55 Antiproliferative activity against mouse L1210 cells assessed as cell growth inh... 32172081
Unchecked IC50 = 280.0 nM 6.55 Antiproliferative activity against human Molt 4/C8 cells assessed as cell growth... 32172081
CCRF-CEM IC50 = 280.0 nM 6.55 Antiproliferative activity against human CEM cells assessed as cell growth inhib... 32172081
L1210 IC50 = 420.0 nM 6.38 Cytotoxicity against murine L1210 cells. 11170648
L1210 IC50 = 420.0 nM 6.38 Cytotoxicity against mouse L1210 cells 19819135
HCT-116 EC50 = 1050.0 nM 5.98 Cytotoxicity in human HCT116 cells assessed as reduction in cell viability incub... 31682427
Caspase-3 IC50 = 1050.0 nM 5.98 Inhibition of caspase-3 (unknown origin) by microplate reader analysis 38262120
L1210 IC50 = 2770.0 nM 5.56 Inhibitory effect on the biosyntheses of DNA in murine L1210 cells. 11170648
L1210 IC50 = 3210.0 nM 5.49 Inhibitory effect on the biosyntheses of protein in murine L1210 cells. 11170648
L1210 IC50 = 5730.0 nM 5.24 Inhibitory effect on the biosyntheses of RNA in murine L1210 cells. 11170648
Unchecked EC50 = 6500.0 nM 5.19 Inhibition of 26S proteasome (unknown origin) incubated for 2 hrs by proteasome ... 31682427

Literature References

PubMed DOI Target Context # Activities
32109059 10.1021/acs.jmedchem.0c00144 Unchecked 11
32109059 10.1021/acs.jmedchem.0c00144 Ubiquitin carboxyl-terminal hydrolase 14 6
32109059 10.1021/acs.jmedchem.0c00144 Ubiquitin carboxyl-terminal hydrolase isozyme L5 6
11170648 10.1021/jm0002580 L1210 4
17499885 10.1016/j.ejmech.2007.03.010 ADMET 3
32109059 10.1021/acs.jmedchem.0c00144 Anamorsin 2
32109059 10.1021/acs.jmedchem.0c00144 No relevant target 2
17499885 10.1016/j.ejmech.2007.03.010 HL-60 1
17499885 10.1016/j.ejmech.2007.03.010 HSC-4 1
19819135 10.1016/j.bmcl.2009.09.069 L1210 1
19819135 10.1016/j.bmcl.2009.09.069 NON-PROTEIN TARGET 1
19819135 10.1016/j.bmcl.2009.09.069 CCRF-CEM 1
31682427 10.1021/acs.jmedchem.9b01138 HCT-116 1
31682427 10.1021/acs.jmedchem.9b01138 Unchecked 1
32109059 10.1021/acs.jmedchem.0c00144 KMS-11 1
38262120 10.1016/j.ejmech.2024.116161 Caspase-3 1
17499885 10.1016/j.ejmech.2007.03.010 HSC-2 1
11170648 10.1021/jm0002580 Unchecked 1
11170648 10.1021/jm0002580 CCRF-CEM 1
11170648 10.1021/jm0002580 NON-PROTEIN TARGET 1

Data from ChEMBL 36 via Core Engine