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Compound Detail

CHEMBL88808

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NC(CCc1ccccc1)P(=O)(O)CC(Cc1ccc(O)cc1)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL88808
Phase Preclinical
Structure Type MOL
InChI Key STVSJGZHUJJREA-UHFFFAOYSA-N
9
Targets
16
Activities
1
Assay Types
0
PK Parameters
15
Publications
0
Known Names

Molecular Properties

377.4
MW (Da)
2.82
ALogP
4
HBA
4
HBD
120.8
PSA (Ų)
0.50
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 C19H24NO5P
MW 377.38
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness 0.44

Activity Summary

Ki 16 meas. best 8.14

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aminopeptidase N
CHEMBL1907
 Ki 8.14 8.14 7.2 1
Leucine aminopeptidase
CHEMBL1293313
 Ki 8.0 8.0 10.0 1
Aminopeptidase N
CHEMBL2590
 Ki 7.44 7.44 36.0 4
Unchecked
CHEMBL612545
 Ki 7.27 6.95 53.6 4
Glutamyl aminopeptidase
CHEMBL3439
 Ki 7.17 7.17 67.0 1
Cytosol aminopeptidase
CHEMBL3965
 Ki 7.17 7.17 67.0 1
Cytosol aminopeptidase
CHEMBL5624
 Ki 7.17 7.17 67.0 2
Endoplasmic reticulum aminopeptidase 2
CHEMBL5043
 Ki 5.98 5.98 1040.0 1
Endoplasmic reticulum aminopeptidase 1
CHEMBL5939
 Ki 5.19 5.19 6470.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aminopeptidase N Ki = 7.2 nM 8.14 Inhibition of human recombinant alanyl aminopeptidase after 30 to 60 mins by mor... 25192493
Leucine aminopeptidase Ki = 10.0 nM 8.0 Inhibition of Plasmodium falciparum LAP 30846252
Aminopeptidase N Ki = 36.0 nM 7.44 Binding affinity towards aminopeptidase N (APN) from pig kidney 12801228
Aminopeptidase N Ki = 36.0 nM 7.44 Inhibition of pig recombinant alanyl aminopeptidase after 30 to 60 mins by morri... 25192493
Aminopeptidase N Ki = 36.0 nM 7.44 Inhibition of APN in porcine kidney using L-leucine p-nitroanilide as substrate ... 29630364
Aminopeptidase N Ki = 36.0 nM 7.44 Inhibition of porcine APN 30846252
Unchecked Ki = 53.6 nM 7.27 Inhibition of Neisseria meningitidis recombinant alanyl aminopeptidase after 30 ... 25192493
Unchecked Ki = 54.0 nM 7.27 Inhibition of Neisseria meningitidis APN 30846252
Cytosol aminopeptidase Ki = 67.0 nM 7.17 Binding affinity for cytosolic leucine aminopeptidase (LAP) from porcine kidney 12801228
Cytosol aminopeptidase Ki = 67.0 nM 7.17 Inhibition of pig recombinant leucine aminopeptidase after 30 to 60 mins by morr... 25192493
Glutamyl aminopeptidase Ki = 67.0 nM 7.17 Inhibition of APA (unknown origin) 29630364
Cytosol aminopeptidase Ki = 67.0 nM 7.17 Inhibition of porcine LAP 30846252
Unchecked Ki = 232.0 nM 6.63 Inhibition of Plasmodium falciparum APN 30846252
Unchecked Ki = 232.0 nM 6.63 Inhibition of Plasmodium falciparum alanyl aminopeptidase assessed as inhibition... 33534577
Endoplasmic reticulum aminopeptidase 2 Ki = 1040.0 nM 5.98 Inhibition of human ERAP2 preincubated for 30 to 60 mins followed by addition of... 27390066
Endoplasmic reticulum aminopeptidase 1 Ki = 6470.0 nM 5.19 Inhibition of human ERAP1 preincubated for 30 to 60 mins followed by addition of... 27390066

Literature References

PubMed DOI Target Context # Activities
25192493 10.1021/jm501071f Aminopeptidase N 2
30846252 10.1016/j.bmcl.2019.02.034 Unchecked 2
12801228 10.1021/jm030795v Cytosol aminopeptidase 1
12801228 10.1021/jm030795v Aminopeptidase N 1
25192493 10.1021/jm501071f Unchecked 1
25192493 10.1021/jm501071f Cytosol aminopeptidase 1
27390066 10.1016/j.bmcl.2016.06.062 Endoplasmic reticulum aminopeptidase 2 1
27390066 10.1016/j.bmcl.2016.06.062 Endoplasmic reticulum aminopeptidase 1 1
29630364 10.1021/acs.jmedchem.7b00782 Unchecked 1
29630364 10.1021/acs.jmedchem.7b00782 Aminopeptidase N 1
29630364 10.1021/acs.jmedchem.7b00782 Glutamyl aminopeptidase 1
30846252 10.1016/j.bmcl.2019.02.034 Aminopeptidase N 1
30846252 10.1016/j.bmcl.2019.02.034 Cytosol aminopeptidase 1
30846252 10.1016/j.bmcl.2019.02.034 Leucine aminopeptidase 1
33534577 10.1021/acs.jmedchem.0c01721 Unchecked 1

Data from ChEMBL 36 via Core Engine