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Compound Detail

CHEMBL3416733

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CC(C)C[C@H](CP(=O)(O)[C@@H](N)CCc1ccccc1)C(=O)N[C@@H](Cc1c[nH]c2ccccc12)C(N)=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3416733
Phase Preclinical
Structure Type MOL
InChI Key QKFOTLXPIIESQI-IEZKXTBUSA-N
5
Targets
24
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

512.6
MW (Da)
3.53
ALogP
4
HBA
5
HBD
151.3
PSA (Ų)
0.22
QED
1
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H37N4O4P
MW 512.59
Aromatic Rings 3
Heavy Atoms 36
NP-Likeness 0.10

Activity Summary

IC50 24 meas. best 8.44

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aminopeptidase N
CHEMBL1907
 IC50 8.44 8.435 3.6 2
Endoplasmic reticulum aminopeptidase 2
CHEMBL5043
 IC50 7.96 7.1613 11.0 8
Leucyl-cystinyl aminopeptidase
CHEMBL2693
 IC50 7.52 7.38 30.0 2
Interleukin-1 receptor antagonist protein
CHEMBL4523191
 IC50 7.52 7.52 30.0 1
Endoplasmic reticulum aminopeptidase 1
CHEMBL5939
 IC50 7.48 6.982 33.0 10

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Aminopeptidase N IC50 = 3.631 nM 8.44 Inhibition of APN (unknown origin) using A-AMC as substrate 33887439
Aminopeptidase N IC50 = 3.7 nM 8.43 Inhibition of APN (unknown origin) using A-AMC as substrate 33887439
Endoplasmic reticulum aminopeptidase 2 IC50 = 11.0 nM 7.96 Inhibition of human recombinant ERAP2 expressed in baculovirus infected cabbage ... 25635706
Endoplasmic reticulum aminopeptidase 2 IC50 = 11.0 nM 7.96 Inhibition of recombinant human ERAP2 using R-AMC as substrate measured for 15 t... 27390066
Endoplasmic reticulum aminopeptidase 2 IC50 = 11.0 nM 7.96 Inhibition of recombinant human ERAP2 using R-AMC as substrate incubated for 5 t... 33887439
Endoplasmic reticulum aminopeptidase 2 IC50 = 11.0 nM 7.96 Inhibition of ERAP2 (unknown origin) using R-AMC as substrate 39011823
Leucyl-cystinyl aminopeptidase IC50 = 30.0 nM 7.52 Inhibition of human recombinant IRAP expressed in baculovirus infected cabbage l... 25635706
Interleukin-1 receptor antagonist protein IC50 = 30.0 nM 7.52 Inhibition of IRAP (unknown origin) using L-AMC as substrate 39011823
Endoplasmic reticulum aminopeptidase 1 IC50 = 33.0 nM 7.48 Inhibition of recombinant human ERAP1 using L-AMC as substrate incubated for 5 t... 33887439
Endoplasmic reticulum aminopeptidase 1 IC50 = 33.0 nM 7.48 Inhibition of ERAP1 (unknown origin) 39011823
Endoplasmic reticulum aminopeptidase 1 IC50 = 33.0 nM 7.48 Inhibition of human recombinant ERAP1 using L-leucine 7-amido-4-methyl coumarin ... 27437077
Endoplasmic reticulum aminopeptidase 1 IC50 = 33.0 nM 7.48 Inhibition of recombinant human ERAP1 using L-AMC as substrate measured for 15 t... 27390066
Endoplasmic reticulum aminopeptidase 1 IC50 = 33.0 nM 7.48 Inhibition of human recombinant ERAP1 expressed in baculovirus infected Sf9 cell... 25635706
Endoplasmic reticulum aminopeptidase 1 IC50 = 48.0 nM 7.32 Inhibition of ERAP1 (unknown origin) expressed in Hi5 cells by in vitro fluorime... 27606717
Endoplasmic reticulum aminopeptidase 2 IC50 = 50.0 nM 7.3 Inhibition of recombinant ERAP2 (unknown origin) expressed in baculovirus infect... 28337326
Endoplasmic reticulum aminopeptidase 1 IC50 = 52.0 nM 7.28 Inhibition of wild type ERAP1 (unknown origin) using L-Rho-Succ-FKARKF as substr... 34267884
Leucyl-cystinyl aminopeptidase IC50 = 57.0 nM 7.24 Inhibition of IRAP (unknown origin) expressed in HEK 293S GnTI(-) cells by in vi... 27606717
Endoplasmic reticulum aminopeptidase 2 IC50 = 80.0 nM 7.1 Inhibition of ERAP2 (unknown origin) expressed in Hi5 cells by in vitro fluorime... 27606717
Endoplasmic reticulum aminopeptidase 1 IC50 = 186.21 nM 6.73 Inhibition of ERAP1 (unknown origin) using L-AMC as substrate 33887439
Endoplasmic reticulum aminopeptidase 1 IC50 = 190.0 nM 6.72 Inhibition of ERAP1 (unknown origin) using L-AMC as substrate 33887439

Literature References

PubMed DOI Target Context # Activities
33887439 10.1016/j.bmcl.2021.128050 Endoplasmic reticulum aminopeptidase 2 3
33887439 10.1016/j.bmcl.2021.128050 Endoplasmic reticulum aminopeptidase 1 3
33887439 10.1016/j.bmcl.2021.128050 Aminopeptidase N 2
33359953 10.1016/j.ejmech.2020.113053 Endoplasmic reticulum aminopeptidase 2 1
39011823 10.1021/acs.jmedchem.4c00840 Interleukin-1 receptor antagonist protein 1
39011823 10.1021/acs.jmedchem.4c00840 Endoplasmic reticulum aminopeptidase 2 1
39011823 10.1021/acs.jmedchem.4c00840 Endoplasmic reticulum aminopeptidase 1 1
34267884 10.1021/acsmedchemlett.1c00235 Aminopeptidase N 1
34267884 10.1021/acsmedchemlett.1c00235 Endoplasmic reticulum aminopeptidase 1 1
33887439 10.1016/j.bmcl.2021.128050 ADMET 1
33359953 10.1016/j.ejmech.2020.113053 Endoplasmic reticulum aminopeptidase 1 1
25635706 10.1021/jm501867s Endoplasmic reticulum aminopeptidase 1 1
27437077 10.1021/acsmedchemlett.6b00084 Endoplasmic reticulum aminopeptidase 1 1
27606717 10.1021/acs.jmedchem.6b01031 Leucyl-cystinyl aminopeptidase 1
27606717 10.1021/acs.jmedchem.6b01031 Endoplasmic reticulum aminopeptidase 2 1
27606717 10.1021/acs.jmedchem.6b01031 Endoplasmic reticulum aminopeptidase 1 1
28337326 10.1021/acsmedchemlett.6b00505 Endoplasmic reticulum aminopeptidase 2 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
25635706 10.1021/jm501867s Leucyl-cystinyl aminopeptidase 1

Data from ChEMBL 36 via Core Engine