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Compound Detail

CHEMBL144896

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NP(=O)(OCc1ccc([N+](=O)[O-])cc1)N(CCCl)CCCl
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL144896
Phase Preclinical
Structure Type MOL
InChI Key KHWBOTPHMVANOX-UHFFFAOYSA-N
6
Targets
20
Activities
1
Assay Types
1
PK Parameters
18
Publications
0
Known Names

Molecular Properties

356.1
MW (Da)
2.96
ALogP
4
HBA
1
HBD
98.7
PSA (Ų)
0.32
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C11H16Cl2N3O4P
MW 356.15
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness -0.66

Activity Summary

IC50 20 meas. best 9.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
ADMET
CHEMBL612558
 IC50 9.4 7.19 0.4 3
V79
CHEMBL614074
 IC50 9.4 6.98 0.4 5
SK-OV-3
CHEMBL614925
 IC50 7.0 6.0038 99.0 8
Trypanosoma cruzi
CHEMBL368
 IC50 5.47 5.47 3400.0 1
Trypanosoma brucei
CHEMBL612849
 IC50 5.47 5.47 3400.0 1
THP-1
CHEMBL614245
 IC50 4.18 4.18 66000.0 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.03833 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
V79 IC50 = 0.4 nM 9.4 Antiproliferative activity against NTR expressing chinese hamster V79 cells afte... 16821793
ADMET IC50 = 0.4 nM 9.4 Inhibitory activity against V79 (chinese hamster fibroblast) cell line with Esch... 14584930
V79 IC50 = 0.8 nM 9.1 Antiproliferative activity against Chinese hamster V79 cells transfected with Es... 21620697
ADMET IC50 = 10.0 nM 8.0 Inhibitory activity against V79 (chinese hamster fibroblast) cell line with Esch... 14584930
V79 IC50 = 10.0 nM 8.0 Antiproliferative activity against NTR expressing chinese hamster V79 cells afte... 16821793
SK-OV-3 IC50 = 99.0 nM 7.0 Antiproliferative activity against human SKOV3 cells transfected with Escherichi... 21620697
SK-OV-3 IC50 = 160.0 nM 6.8 Antiproliferative activity against NTR expressing human SKOV3 cells after 18 hrs 16821793
SK-OV-3 IC50 = 980.0 nM 6.01 Antiproliferative activity against human SKOV3 cells with mixed population of 25... 21620697
SK-OV-3 IC50 = 1100.0 nM 5.96 Cytotoxicity against human SKOV3 cells 30295477
SK-OV-3 IC50 = 1200.0 nM 5.92 Inhibitory activity against SKOV3 (human ovarian carcinoma) cell line with Esche... 14584930
SK-OV-3 IC50 = 1200.0 nM 5.92 Antiproliferative activity against NTR expressing human SKOV3 cells infected wit... 16821793
Trypanosoma brucei IC50 = 3400.0 nM 5.47 Antiparasitic activity against Trypanosoma brucei BSF after 3 days by Alamar blu... 20028822
Trypanosoma cruzi IC50 = 3400.0 nM 5.47 Trypanocidal activity against Trypanosoma cruzi intracellular amastigotes forms ... 21620697
SK-OV-3 IC50 = 6200.0 nM 5.21 Inhibitory activity against SKOV3 (human ovarian carcinoma) cell line infected a... 14584930
SK-OV-3 IC50 = 6200.0 nM 5.21 Antiproliferative activity against NTR expressing human SKOV3 cells infected wit... 16821793
V79 IC50 = 59000.0 nM 4.23 Antiproliferative activity against Chinese hamster V79 cells assessed as reducti... 21620697
THP-1 IC50 = 66000.0 nM 4.18 Cytotoxicity against human THP1 cells after 6 days by Alamar blue assay 20028822
ADMET IC50 = 67000.0 nM 4.17 Inhibitory activity against V79 (chinese hamster fibroblast) cell line without E... 14584930
V79 IC50 = 67000.0 nM 4.17 Antiproliferative activity against chinese hamster V79 cells after 72 hrs 16821793

Literature References

PubMed DOI Target Context # Activities
16821793 10.1021/jm051246n SK-OV-3 9
14584930 10.1021/jm034133h ADMET 7
16821793 10.1021/jm051246n V79 6
21620697 10.1016/j.bmcl.2011.05.009 SK-OV-3 5
14584930 10.1021/jm034133h Unchecked 4
14584930 10.1021/jm034133h SK-OV-3 4
20028822 10.1128/aac.01213-09 Unchecked 3
21620697 10.1016/j.bmcl.2011.05.009 V79 3
21620697 10.1016/j.bmcl.2011.05.009 Unchecked 2
30295477 10.1021/acs.jmedchem.8b00147 SK-OV-3 1
21620697 10.1016/j.bmcl.2011.05.009 Leishmania major 1
21620697 10.1016/j.bmcl.2011.05.009 Trypanosoma brucei 1
21620697 10.1016/j.bmcl.2011.05.009 Trypanosoma cruzi 1
20028822 10.1128/aac.01213-09 ADMET 1
20028822 10.1128/aac.01213-09 THP-1 1
20028822 10.1128/aac.01213-09 Trypanosoma brucei 1
16821793 10.1021/jm051246n ADMET 1
16821793 10.1021/jm051246n Oxygen-insensitive NAD(P)H nitroreductase 1

Data from ChEMBL 36 via Core Engine