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Compound Detail

CHEMBL189620

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N#C[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)CCCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL189620
Phase Preclinical
Structure Type MOL
InChI Key SPXFAUXQZWJGCJ-ROUUACIJSA-N
5
Targets
16
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

339.4
MW (Da)
2.51
ALogP
3
HBA
0
HBD
64.4
PSA (Ų)
0.83
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 C20H25N3O2
MW 339.44
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness -0.66

Activity Summary

Ki 9 meas. best 10.7
IC50 7 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prolyl endopeptidase
CHEMBL2461
 Ki 10.7 10.4467 0.0 3
Prolyl endopeptidase
CHEMBL3202
 Ki 10.7 9.85 0.0 4
Prolyl endopeptidase
CHEMBL4035
 Ki 10.7 10.7 0.0 1
Unchecked
CHEMBL612545
 Ki 10.7 10.7 0.0 1
Prolyl endopeptidase
CHEMBL2461
 IC50 9.7 9.27 0.2 5
Prolyl endopeptidase
CHEMBL4935
 IC50 9.52 9.52 0.3 1
Unchecked
CHEMBL612545
 IC50 8.22 8.22 6.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prolyl endopeptidase Ki = 0.02 nM 10.7 Inhibitory activity against prolyl oligopeptidase of porcine brain homogenate 15509157
Prolyl endopeptidase Ki = 0.02 nM 10.7 Inhibition of POP in Han/Wistar rat brain using Suc-Gly-Pro-AMC substrate incuba... 26619267
Unchecked Ki = 0.02 nM 10.7 Binding affinity to PREP (unknown origin) assessed as inhibition constant 37248563
Prolyl endopeptidase Ki = 0.02 nM 10.7 Inhibition of PREP (unknown origin) assessed as inhibition constant 38546708
Prolyl endopeptidase Ki = 0.023 nM 10.64 Inhibition of pig POP 20058865
Prolyl endopeptidase Ki = 0.023 nM 10.64 Inhibition of prolyl oligopeptidase (unknown origin) 24763264
Prolyl endopeptidase Ki = 0.1 nM 10.0 Inhibition of porcine prolyl oligopeptidase using Z-Gly-Pro-AMC as substrate aft... 24763264
Prolyl endopeptidase IC50 = 0.2 nM 9.7 Inhibitory activity against prolyl oligopeptidase of porcine brain homogenate 15509157
Prolyl endopeptidase IC50 = 0.2 nM 9.7 Inhibition of recombinant porcine PREP expressed in Escherichia coli using Suc-G... 34671446
Prolyl endopeptidase IC50 = 0.22 nM 9.66 In vitro inhibitory activity against porcine prolyl oligopeptidase by using 4 mM... 16033257
Prolyl endopeptidase IC50 = 0.3 nM 9.52 Inhibition of PREP in C57BL/6 mouse cortex homogenate assessed as formation of 7... 31857839
Prolyl endopeptidase IC50 = 0.86 nM 9.07 Inhibition of recombinant porcine brain PREP expressed in Escherichia coli asses... 31857839
Prolyl endopeptidase Ki = 0.92 nM 9.04 Inhibition of human POP by tight binding based Morrison equation analysis 26619267
Prolyl endopeptidase Ki = 0.95 nM 9.02 Inhibition of human POP expressed in Escherichia coli BL21 pre-incubated for 30 ... 26619267
Prolyl endopeptidase IC50 = 6.0 nM 8.22 Inhibition of pig PREP expressed in Escherichia coli using Z-Gly-Pro-p-nitroanil... 23121075
Unchecked IC50 = 6.0 nM 8.22 Inhibition of POP (unknown origin) 35797897

Literature References

PubMed DOI Target Context # Activities
37248563 10.1021/acs.jmedchem.3c00235 Unchecked 19
37248563 10.1021/acs.jmedchem.3c00235 Mus musculus 4
31857839 10.1021/acsmedchemlett.9b00394 Prolyl endopeptidase 4
26619267 10.1021/acs.jmedchem.5b01296 Prolyl endopeptidase 3
- 10.6019/CHEMBL5724709 HEK-293T 2
- 10.6019/CHEMBL5724709 U2OS 2
24763264 10.1016/j.ejmech.2014.04.014 Prolyl endopeptidase 2
15509157 10.1021/jm049503w Prolyl endopeptidase 2
34671446 10.1021/acsmedchemlett.1c00399 Prolyl endopeptidase 2
- 10.6019/CHEMBL5724709 Fibroblast 2
15509157 10.1021/jm049503w No relevant target 1
23121075 10.1021/jm301060g Unchecked 1
16033257 10.1021/jm0500020 Prolyl endopeptidase 1
35797897 10.1016/j.ejmech.2022.114543 Dipeptidyl peptidase 4 1
35797897 10.1016/j.ejmech.2022.114543 Unchecked 1
34671446 10.1021/acsmedchemlett.1c00399 HEK293 1
20058865 10.1021/jm901104g Prolyl endopeptidase 1
23121075 10.1021/jm301060g Prolyl endopeptidase 1
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
23121075 10.1021/jm301060g Dipeptidyl peptidase 4 1

Data from ChEMBL 36 via Core Engine