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Compound Detail

CHEMBL79993

Z-PRO-PROLINAL
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O=C[C@@H]1CCCN1C(=O)[C@@H]1CCCN1C(=O)OCc1ccccc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL79993
Name Z-PRO-PROLINAL
Phase Preclinical
Structure Type MOL
InChI Key ORZXYSPOAVJYRU-HOTGVXAUSA-N
8
Targets
17
Activities
2
Assay Types
1
PK Parameters
18
Publications
0
Known Names

Molecular Properties

330.4
MW (Da)
1.98
ALogP
4
HBA
0
HBD
66.9
PSA (Ų)
0.79
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C18H22N2O4
MW 330.38
Aromatic Rings 1
Heavy Atoms 24
NP-Likeness -0.29

Activity Summary

Ki 10 meas. best 9.68
IC50 7 meas. best 9.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prolyl endopeptidase
CHEMBL2460
 Ki 9.68 9.57 0.2 2
Unchecked
CHEMBL612545
 Ki 9.54 8.695 0.3 2
Prolyl endopeptidase
CHEMBL2461
 IC50 9.48 9.48 0.3 2
Prolyl endopeptidase
CHEMBL4935
 Ki 9.46 9.46 0.3 1
Prolyl endopeptidase
CHEMBL3202
 Ki 9.4 8.7175 0.4 4
Prolyl endopeptidase
CHEMBL6043
 Ki 9.3 9.3 0.5 1
Prolyl endopeptidase
CHEMBL3202
 IC50 8.96 8.76 1.1 2
Prolyl endopeptidase
CHEMBL6043
 IC50 8.9 8.9 1.3 1
Chymotrypsin-like elastase family member 1
CHEMBL3000
 IC50 7.29 7.29 51.6 1
Prolyl endopeptidase
CHEMBL4035
 IC50 7.27 7.27 54.0 1

Pharmacokinetic Data

Parameter Value Units Species
Ka 7.8 10'5/M/s Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prolyl endopeptidase Ki = 0.21 nM 9.68 Inhibition of bovine brain POP 20058865
Unchecked Ki = 0.29 nM 9.54 Inhibition of POP (unknown origin) 35797897
Prolyl endopeptidase IC50 = 0.33 nM 9.48 In vitro inhibitory activity against porcine prolyl oligopeptidase by using 4 mM... 16033257
Prolyl endopeptidase IC50 = 0.33 nM 9.48 In vitro inhibitory activity against prolyl oligopeptidase (POP) from pig brain ... 12238937
Prolyl endopeptidase Ki = 0.35 nM 9.46 Inhibition of mouse brain POP 20058865
Prolyl endopeptidase Ki = 0.35 nM 9.46 Inhibition of POP in bovine serum using Z-Gly-Pro-NH-Mec fluorimetric substrate 26619267
Prolyl endopeptidase Ki = 0.4 nM 9.4 Inhibition of recombinant human POP assessed as affinity constant of second step... 31393718
Prolyl endopeptidase Ki = 0.5 nM 9.3 Inhibition of Flavobacterium meningosepticum POP 20058865
Prolyl endopeptidase Ki = 1.0 nM 9.0 Inhibition of recombinant human POP pre-incubated for 30 mins before addition of... 31393718
Prolyl endopeptidase IC50 = 1.1 nM 8.96 In vitro inhibitory activity against purified prolyl endopeptidase (PEP) from ca... 8027988
Prolyl endopeptidase IC50 = 1.27 nM 8.9 Inhibition of Flavobacterium meningosepticum propyl endopeptidase 14510601
Prolyl endopeptidase IC50 = 2.75 nM 8.56 Inhibition of POP (unknown origin) using (Z)-Gly-Pro-p-nitroanilide as substrate... 30701972
Prolyl endopeptidase Ki = 4.3 nM 8.37 Inhibition of prolyl oligopeptidase 20627594
Prolyl endopeptidase Ki = 8.0 nM 8.1 Inhibition of recombinant human POP assessed as affinity constant of first step ... 31393718
Unchecked Ki = 14.0 nM 7.85 Inhibition of POP in rabbit brain homogenate 20058865
Chymotrypsin-like elastase family member 1 IC50 = 51.6 nM 7.29 Inhibition of Flavobacterium meningosepticum PEP 11809072
Prolyl endopeptidase IC50 = 54.0 nM 7.27 Inhibitory activity was evaluated against Post-proline cleaving enzyme from rat ... 8691432

Literature References

PubMed DOI Target Context # Activities
31393718 10.1021/acs.jmedchem.9b00642 Prolyl endopeptidase 6
20058865 10.1021/jm901104g Prolyl endopeptidase 3
26619267 10.1021/acs.jmedchem.5b01296 Prolyl endopeptidase 1
35797897 10.1016/j.ejmech.2022.114543 Unchecked 1
31393718 10.1021/acs.jmedchem.9b00642 Prolyl endopeptidase FAP 1
30701972 10.1021/acs.jnatprod.8b00592 No relevant target 1
30701972 10.1021/acs.jnatprod.8b00592 Glycogen synthase kinase-3 beta 1
30701972 10.1021/acs.jnatprod.8b00592 Prolyl endopeptidase 1
30701972 10.1021/acs.jnatprod.8b00592 Acetylcholinesterase 1
30701972 10.1021/acs.jnatprod.8b00592 Cholinesterase 1
8027988 10.1021/jm00039a019 Prolyl endopeptidase 1
20627594 10.1016/j.bmc.2010.05.012 Prolyl endopeptidase 1
20058865 10.1021/jm901104g Unchecked 1
11809072 10.1021/np010194b Chymotrypsin-like elastase family member 1 1
14510601 10.1021/np020186a Prolyl endopeptidase 1
16033257 10.1021/jm0500020 Prolyl endopeptidase 1
8691432 10.1021/jm950858c Prolyl endopeptidase 1
12238937 10.1021/jm020966g Prolyl endopeptidase 1

Data from ChEMBL 36 via Core Engine