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Compound Detail

CHEMBL2023820

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O=C(O)c1cccc(Nc2ccc([N+](=O)[O-])c3ccccc23)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2023820
Phase Preclinical
Structure Type MOL
InChI Key ZLIDMWNTWSBTSM-UHFFFAOYSA-N
5
Targets
12
Activities
1
Assay Types
0
PK Parameters
14
Publications
0
Known Names

Molecular Properties

308.3
MW (Da)
4.19
ALogP
4
HBA
2
HBD
92.5
PSA (Ų)
0.56
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C17H12N2O4
MW 308.29
Aromatic Rings 3
Heavy Atoms 23
NP-Likeness -1.14

Activity Summary

IC50 12 meas. best 7.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aldo-keto reductase family 1 member C3
CHEMBL4681
 IC50 7.1 7.085 80.0 2
Androgen receptor
CHEMBL1871
 IC50 5.33 5.11 4700.0 4
Aldo-keto reductase family 1 member C4
CHEMBL4999
 IC50 5.09 4.8 8170.0 2
Aldo-keto reductase family 1 member C2
CHEMBL5847
 IC50 5.09 4.85 8170.0 2
Aldo-keto reductase family 1 member C1
CHEMBL5905
 IC50 4.96 4.67 11100.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aldo-keto reductase family 1 member C3 IC50 = 80.0 nM 7.1 Inhibition of recombinant AKR1C3 assessed as enzyme catalyzed oxidation of S-tet... 22507964
Aldo-keto reductase family 1 member C3 IC50 = 86.0 nM 7.07 Inhibition of human AKR1C3 using S-tetralol as substrate in presence of NADP by ... 32463235
Androgen receptor IC50 = 4700.0 nM 5.33 Antagonist activity at androgen receptor expressed in HeLa-AR3A-PSA-(ARE)4-Luc13... 22507964
Androgen receptor IC50 = 4700.0 nM 5.33 Antagonistic activity at AR in human 22Rv1 cells assessed as reduction in cell n... 32847363
Androgen receptor IC50 = 8000.0 nM 5.1 Displacement of [3H]-R1881 from androgen receptor (unknown origin) expressed in ... 32463235
Aldo-keto reductase family 1 member C2 IC50 = 8170.0 nM 5.09 Inhibition of recombinant AKR1C2 assessed as enzyme catalyzed oxidation of S-tet... 22507964
Aldo-keto reductase family 1 member C4 IC50 = 8170.0 nM 5.09 Inhibition of recombinant AKR1C4 assessed as enzyme catalyzed oxidation of S-tet... 22507964
Aldo-keto reductase family 1 member C1 IC50 = 11100.0 nM 4.96 Inhibition of recombinant AKR1C1 assessed as enzyme catalyzed oxidation of S-tet... 22507964
Androgen receptor IC50 = 21000.0 nM 4.68 Antagonist activity at androgen receptor (unknown origin) expressed in human HeL... 32463235
Aldo-keto reductase family 1 member C2 IC50 = 24700.0 nM 4.61 Inhibition of human AKR1C2 using S-tetralol as substrate in presence of NADP by ... 32463235
Aldo-keto reductase family 1 member C4 IC50 = 30600.0 nM 4.51 Inhibition of human AKR1C4 using S-tetralol as substrate in presence of NADP by ... 32463235
Aldo-keto reductase family 1 member C1 IC50 = 41300.0 nM 4.38 Inhibition of human AKR1C1 using S-tetralol as substrate in presence of NADP by ... 32463235

Literature References

PubMed DOI Target Context # Activities
22507964 10.1016/j.bmcl.2012.03.085 Androgen receptor 4
22507964 10.1016/j.bmcl.2012.03.085 Unchecked 3
22507964 10.1016/j.bmcl.2012.03.085 Aldo-keto reductase family 1 member C3 2
32463235 10.1021/acs.jmedchem.9b02138 Androgen receptor 2
22507964 10.1016/j.bmcl.2012.03.085 Aldo-keto reductase family 1 member C1 1
22507964 10.1016/j.bmcl.2012.03.085 Aldo-keto reductase family 1 member C2 1
22507964 10.1016/j.bmcl.2012.03.085 Aldo-keto reductase family 1 member C4 1
22507964 10.1016/j.bmcl.2012.03.085 Prostaglandin G/H synthase 1 1
22507964 10.1016/j.bmcl.2012.03.085 Prostaglandin G/H synthase 2 1
32847363 10.1021/acs.jmedchem.0c00939 Androgen receptor 1
32463235 10.1021/acs.jmedchem.9b02138 Aldo-keto reductase family 1 member C4 1
32463235 10.1021/acs.jmedchem.9b02138 Aldo-keto reductase family 1 member C2 1
32463235 10.1021/acs.jmedchem.9b02138 Aldo-keto reductase family 1 member C3 1
32463235 10.1021/acs.jmedchem.9b02138 Aldo-keto reductase family 1 member C1 1

Data from ChEMBL 36 via Core Engine