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Compound Detail

CHEMBL2159748

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N#C[C@@H]1CCCN1C(=O)c1cccc2c1C(=O)N(Cc1ccccc1)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2159748
Phase Preclinical
Structure Type MOL
InChI Key AUHQVJXPKRFCST-KRWDZBQOSA-N
2
Targets
12
Activities
2
Assay Types
4
PK Parameters
8
Publications
0
Known Names

Molecular Properties

345.4
MW (Da)
2.97
ALogP
3
HBA
0
HBD
64.4
PSA (Ų)
0.86
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H19N3O2
MW 345.40
Aromatic Rings 2
Heavy Atoms 26
NP-Likeness -0.87

Activity Summary

IC50 8 meas. best 7.35
Ki 4 meas. best 7.64

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prolyl endopeptidase
CHEMBL3202
 Ki 7.64 7.6133 23.0 3
Prolyl endopeptidase
CHEMBL3202
 IC50 7.35 6.8763 45.0 8
Unchecked
CHEMBL612545
 Ki 7.35 7.35 45.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 39.0 mL.min-1.g-1 Rattus norvegicus
CL 13.0 mL.min-1.g-1 Homo sapiens
T1/2 0.5833 hr Rattus norvegicus
T1/2 1.85 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prolyl endopeptidase Ki = 23.0 nM 7.64 Inhibition of human POP expressed in Escherichia coli BL21 pre-incubated for 30 ... 26619267
Prolyl endopeptidase Ki = 25.0 nM 7.6 Inhibition of recombinant human POP assessed as affinity constant of second step... 31393718
Prolyl endopeptidase Ki = 25.0 nM 7.6 Inhibition of recombinant human POP pre-incubated for 30 mins before addition of... 31393718
Prolyl endopeptidase IC50 = 45.0 nM 7.35 Inhibition of POP in human HCEC cell extracts using Cbz-Gly-Pro-AMC substrate in... 22765237
Prolyl endopeptidase IC50 = 45.0 nM 7.35 Inhibition of POP in human LNZ308 cell extracts using Cbz-Gly-Pro-AMC substrate ... 22765237
Prolyl endopeptidase IC50 = 45.0 nM 7.35 Inhibition of POP in human LN229 cell extracts using Cbz-Gly-Pro-AMC substrate i... 22765237
Unchecked Ki = 45.0 nM 7.35 Inhibition of POP (unknown origin) 35797897
Prolyl endopeptidase IC50 = 81.0 nM 7.09 Inhibition of POP in human LN18 cell extracts using Cbz-Gly-Pro-AMC substrate in... 22765237
Prolyl endopeptidase IC50 = 200.0 nM 6.7 Inhibition of POP in intact human LNZ308 cells using Cbz-Gly-Pro-AMC substrate i... 22765237
Prolyl endopeptidase IC50 = 300.0 nM 6.52 Inhibition of POP in intact human LN18 cells using Cbz-Gly-Pro-AMC substrate inc... 22765237
Prolyl endopeptidase IC50 = 450.0 nM 6.35 Inhibition of POP in intact human LN229 cells using Cbz-Gly-Pro-AMC substrate in... 22765237
Prolyl endopeptidase IC50 = 500.0 nM 6.3 Inhibition of POP in intact human HCEC cells using Cbz-Gly-Pro-AMC substrate inc... 22765237

Literature References

PubMed DOI Target Context # Activities
22765237 10.1021/jm3002839 Prolyl endopeptidase 18
22765237 10.1021/jm3002839 Liver microsomes 4
22765237 10.1021/jm3002839 Dipeptidyl peptidase 4 4
31393718 10.1021/acs.jmedchem.9b00642 Prolyl endopeptidase 3
22765237 10.1021/jm3002839 Prolyl endopeptidase FAP 2
26619267 10.1021/acs.jmedchem.5b01296 Prolyl endopeptidase 1
31393718 10.1021/acs.jmedchem.9b00642 Prolyl endopeptidase FAP 1
35797897 10.1016/j.ejmech.2022.114543 Unchecked 1

Data from ChEMBL 36 via Core Engine