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Compound Detail

CHEMBL219777

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O=C(NO)/C(=C\c1ccccc1)C(=O)NCc1ccc(F)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL219777
Phase Preclinical
Structure Type MOL
InChI Key HJPWSHCUMPAXLD-GDNBJRDFSA-N
5
Targets
9
Activities
1
Assay Types
11
PK Parameters
17
Publications
0
Known Names

Molecular Properties

314.3
MW (Da)
2.03
ALogP
3
HBA
3
HBD
78.4
PSA (Ų)
0.26
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 C17H15FN2O3
MW 314.32
Aromatic Rings 2
Heavy Atoms 23
NP-Likeness -0.90

Activity Summary

IC50 9 meas. best 8.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aminopeptidase N
CHEMBL4117
 IC50 8.22 8.22 6.0 1
Unchecked
CHEMBL612545
 IC50 8.22 8.22 6.0 1
Aminopeptidase N
CHEMBL2590
 IC50 5.86 5.86 1372.0 2
Plasmodium falciparum
CHEMBL364
 IC50 4.96 4.7725 11000.0 4
MRC5
CHEMBL614181
 IC50 4.5 4.5 32000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 21373.76 ng.hr.mL-1 Mus musculus
AUC 98.0 uM.hr/mg Mus musculus
AUC 28288.8 ng.hr.mL-1 Mus musculus
AUC 20745.12 ng.hr.mL-1 Mus musculus
T1/2 22.0 hr Rattus norvegicus
T1/2 24.0 hr Homo sapiens
T1/2 24.0 hr -
T1/2 1.5 hr Mus musculus
T1/2 1.0 hr Mus musculus
T1/2 24.0 hr Homo sapiens
T1/2 22.0 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aminopeptidase N IC50 = 6.0 nM 8.22 Inhibition of Plasmodium falciparum FcB1 M1 aminopeptidase 17326615
Unchecked IC50 = 6.0 nM 8.22 Inhibition of Plasmodium falciparum AM1 using Leu-pNA as substrate preincubated ... 23176597
Aminopeptidase N IC50 = 1372.0 nM 5.86 Inhibition of pig kidney microsomal APN 17326615
Aminopeptidase N IC50 = 1372.0 nM 5.86 Inhibition of porcine kidney microsomal neutral aminopeptidase using Leu-pNA as ... 23176597
Plasmodium falciparum IC50 = 11000.0 nM 4.96 Antimalarial activity against Plasmodium falciparum K1 infected in human O posit... 23176597
Plasmodium falciparum IC50 = 13000.0 nM 4.89 Antimalarial activity against chloroquine-sensitive Plasmodium falciparum F32 17326615
Plasmodium falciparum IC50 = 24000.0 nM 4.62 Antimalarial activity against chloroquine-resistant Plasmodium falciparum FcB1 17326615
Plasmodium falciparum IC50 = 24000.0 nM 4.62 Antimalarial activity against Plasmodium falciparum FcB1 infected in human O pos... 23176597
MRC5 IC50 = 32000.0 nM 4.5 Cytotoxicity against human MRC5 SV2 cells after 72 hrs by resazurin fluorimetric... 23176597

Literature References

PubMed DOI Target Context # Activities
23176597 10.1021/jm301506h Plasma 7
23176597 10.1021/jm301506h ADMET 4
17326615 10.1021/jm061169b Aminopeptidase N 2
17326615 10.1021/jm061169b No relevant target 2
23176597 10.1021/jm301506h Plasmodium falciparum 2
17326615 10.1021/jm061169b Plasmodium falciparum 2
19821586 10.1021/jm900648x Plasma 2
19821586 10.1021/jm900648x No relevant target 2
23176597 10.1021/jm301506h No relevant target 2
23176597 10.1021/jm301506h Unchecked 1
23176597 10.1021/jm301506h MRC5 1
23176597 10.1021/jm301506h Aminopeptidase N 1
23176597 10.1021/jm301506h Liver microsomes 1
23176597 10.1021/jm301506h Liver 1
23176597 10.1021/jm301506h Carbonic anhydrase 2 1
17326615 10.1021/jm061169b Unchecked 1
17326615 10.1021/jm061169b Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine