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Compound Detail

CHEMBL327844

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NC(CCc1ccccc1)P(=O)(O)CC(Cc1ccccc1)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL327844
Phase Preclinical
Structure Type MOL
InChI Key QELOIXSGJMIHBZ-UHFFFAOYSA-N
9
Targets
20
Activities
2
Assay Types
0
PK Parameters
18
Publications
0
Known Names

Molecular Properties

361.4
MW (Da)
3.12
ALogP
3
HBA
3
HBD
100.6
PSA (Ų)
0.60
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C19H24NO4P
MW 361.38
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness 0.30

Activity Summary

Ki 18 meas. best 8.7
IC50 2 meas. best 7.62

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aminopeptidase N
CHEMBL1907
 Ki 8.7 8.7 2.0 1
Leucine aminopeptidase
CHEMBL1293313
 Ki 7.89 7.885 13.0 2
Plasmodium falciparum
CHEMBL364
 IC50 7.62 7.62 24.0 1
Cytosol aminopeptidase
CHEMBL3965
 Ki 7.18 7.18 66.0 2
Cytosol aminopeptidase
CHEMBL5624
 Ki 7.18 7.18 66.0 2
Unchecked
CHEMBL612545
 Ki 7.11 6.9083 78.0 6
Unchecked
CHEMBL612545
 IC50 7.1 7.1 79.0 1
Aminopeptidase N
CHEMBL2590
 Ki 6.56 6.56 276.0 3
Endoplasmic reticulum aminopeptidase 2
CHEMBL5043
 Ki 6.46 6.46 350.0 1
Endoplasmic reticulum aminopeptidase 1
CHEMBL5939
 Ki 4.72 4.72 19100.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aminopeptidase N Ki = 2.0 nM 8.7 Inhibition of human recombinant alanyl aminopeptidase after 30 to 60 mins by mor... 25192493
Leucine aminopeptidase Ki = 13.0 nM 7.89 Inhibition of Plasmodium falciparum LAP 30846252
Leucine aminopeptidase Ki = 13.2 nM 7.88 Inhibition of Plasmodium falciparum recombinant leucine aminopeptidase 18262419
Plasmodium falciparum IC50 = 24.0 nM 7.62 Antimalarial activity against Plasmodium falciparum 3D7 infected in human O posi... 23176597
Cytosol aminopeptidase Ki = 66.0 nM 7.18 Binding affinity for cytosolic leucine aminopeptidase (LAP) from porcine kidney 12801228
Cytosol aminopeptidase Ki = 66.0 nM 7.18 Inhibition of pig kidney cytosolic leucine aminopeptidase 18262419
Cytosol aminopeptidase Ki = 66.0 nM 7.18 Inhibition of pig recombinant leucine aminopeptidase after 30 to 60 mins by morr... 25192493
Cytosol aminopeptidase Ki = 66.0 nM 7.18 Inhibition of porcine LAP 30846252
Unchecked Ki = 78.0 nM 7.11 Inhibition of Plasmodium falciparum APN preincubated for 30 mins followed by add... 27390066
Unchecked IC50 = 79.0 nM 7.1 Inhibition of Plasmodium falciparum recombinant AM1 using Leu-pNA as substrate 23176597
Unchecked Ki = 79.0 nM 7.1 Inhibition of Plasmodium falciparum alanyl aminopeptidase assessed as inhibition... 33534577
Unchecked Ki = 79.0 nM 7.1 Inhibition of recombinant Plasmodium falciparum A-M1 assessed as inhibition cons... 33534577
Unchecked Ki = 79.0 nM 7.1 Inhibition of Plasmodium falciparum APN 30846252
Aminopeptidase N Ki = 276.0 nM 6.56 Binding affinity towards aminopeptidase N (APN) from pig kidney 12801228
Aminopeptidase N Ki = 276.0 nM 6.56 Inhibition of pig recombinant alanyl aminopeptidase after 30 to 60 mins by morri... 25192493
Aminopeptidase N Ki = 276.0 nM 6.56 Inhibition of porcine APN 30846252
Unchecked Ki = 302.0 nM 6.52 Inhibition of Neisseria meningitidis recombinant alanyl aminopeptidase after 30 ... 25192493
Unchecked Ki = 302.0 nM 6.52 Inhibition of Neisseria meningitidis APN 30846252
Endoplasmic reticulum aminopeptidase 2 Ki = 350.0 nM 6.46 Inhibition of human ERAP2 preincubated for 30 to 60 mins followed by addition of... 27390066
Endoplasmic reticulum aminopeptidase 1 Ki = 19100.0 nM 4.72 Inhibition of human ERAP1 preincubated for 30 to 60 mins followed by addition of... 27390066

Literature References

PubMed DOI Target Context # Activities
33534577 10.1021/acs.jmedchem.0c01721 Unchecked 2
30846252 10.1016/j.bmcl.2019.02.034 Unchecked 2
25192493 10.1021/jm501071f Aminopeptidase N 2
25192493 10.1021/jm501071f Cytosol aminopeptidase 1
30846252 10.1016/j.bmcl.2019.02.034 Leucine aminopeptidase 1
30846252 10.1016/j.bmcl.2019.02.034 Cytosol aminopeptidase 1
30846252 10.1016/j.bmcl.2019.02.034 Aminopeptidase N 1
27390066 10.1016/j.bmcl.2016.06.062 Endoplasmic reticulum aminopeptidase 1 1
27390066 10.1016/j.bmcl.2016.06.062 Endoplasmic reticulum aminopeptidase 2 1
27390066 10.1016/j.bmcl.2016.06.062 Unchecked 1
12801228 10.1021/jm030795v Cytosol aminopeptidase 1
25192493 10.1021/jm501071f Unchecked 1
23176597 10.1021/jm301506h Unchecked 1
23176597 10.1021/jm301506h Plasmodium falciparum 1
23176597 10.1021/jm301506h MRC5 1
18262419 10.1016/j.bmcl.2008.01.107 Leucine aminopeptidase 1
18262419 10.1016/j.bmcl.2008.01.107 Cytosol aminopeptidase 1
12801228 10.1021/jm030795v Aminopeptidase N 1

Data from ChEMBL 36 via Core Engine