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Compound Detail

CHEMBL4463665

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N#CC1(NC(=O)[C@H](Cc2ccccc2)NC(=O)c2ccccc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4463665
Phase Preclinical
Structure Type MOL
InChI Key PIEOUSVKYUIHRE-KRWDZBQOSA-N
6
Targets
12
Activities
1
Assay Types
2
PK Parameters
18
Publications
0
Known Names

Molecular Properties

333.4
MW (Da)
2.20
ALogP
3
HBA
2
HBD
82.0
PSA (Ų)
0.85
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Unknown
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H19N3O2
MW 333.39
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -0.74

Activity Summary

Ki 12 meas. best 7.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Procathepsin L
CHEMBL3837
 Ki 7.4 7.3667 39.8 3
Cathepsin S
CHEMBL2954
 Ki 7.1 7.1 79.4 1
Unchecked
CHEMBL612545
 Ki 6.8 6.8 158.5 1
Cruzipain
CHEMBL3563
 Ki 6.7 6.6 199.5 5
Cathepsin K
CHEMBL268
 Ki 6.4 6.4 398.1 1
Cathepsin B
CHEMBL4072
 Ki 5.1 5.1 7943.3 1

Pharmacokinetic Data

Parameter Value Units Species
T1/2 100.0 hr -
T1/2 2.65 hr -

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Procathepsin L Ki = 39.81 nM 7.4 Inhibition of Cathepsin L (unknown origin) using Z-Phe-Arg-7-amido-4-methylcouma... 31561938
Procathepsin L Ki = 39.81 nM 7.4 Inhibition of recombinant human liver CatL using Z-FR-AMC as substrate by fluore... 33991733
Procathepsin L Ki = 50.12 nM 7.3 Inhibition of human cathepsin L using Z-Phe-Arg-7-amido-4-methylcoumarin as subs... 33038787
Cathepsin S Ki = 79.43 nM 7.1 Inhibition of recombinant human liver CatS using Z-FR-AMC as substrate by fluore... 33991733
Unchecked Ki = 158.49 nM 6.8 Inhibition of Leishmania mexicana CPB delta CTE mutant using Z-Phe-Arg-7-amido-4... 33038787
Cruzipain Ki = 199.53 nM 6.7 Inhibition of Trypanosoma cruzi cruzain using Z-FR-AMC as substrate by fluoresce... 33991733
Cruzipain Ki = 251.19 nM 6.6 Covalent inhibition of Trypanosoma cruzi cruzipain using Z-Phe-Arg-7-amidomethyl... 34095840
Cruzipain Ki = 251.19 nM 6.6 Inhibition of recombinant Trypanosoma cruzi cruzain using Z-Phe-Arg-7-amido-4-me... 33038787
Cruzipain Ki = 251.0 nM 6.6 Binding affinity to Trypanosoma cruzi Cruzain assessed as inhibition constant 30282318
Cruzipain Ki = 316.23 nM 6.5 Inhibition of Trypanosoma cruzi cruzain using Z-Phe-Arg-7-amido-4-methylcoumarin... 31561938
Cathepsin K Ki = 398.11 nM 6.4 Inhibition of recombinant human liver CatK using Z-FR-AMC as substrate by fluore... 33991733
Cathepsin B Ki = 7943.28 nM 5.1 Inhibition of recombinant human liver CatB using Z-FR-AMC as substrate by fluore... 33991733

Literature References

PubMed DOI Target Context # Activities
34095840 10.1039/d0md00097c Unchecked 2
33038787 10.1016/j.bmc.2020.115743 Unchecked 1
30282318 10.1016/j.ejmech.2018.08.079 Cruzipain 1
33991733 10.1016/j.bmc.2021.116211 Cathepsin S 1
33991733 10.1016/j.bmc.2021.116211 Cathepsin K 1
33991733 10.1016/j.bmc.2021.116211 Cathepsin B 1
33991733 10.1016/j.bmc.2021.116211 Procathepsin L 1
33991733 10.1016/j.bmc.2021.116211 Cruzipain 1
33038787 10.1016/j.bmc.2020.115743 Cruzipain 1
33038787 10.1016/j.bmc.2020.115743 Procathepsin L 1
31561938 10.1016/j.bmc.2019.115083 Cruzipain 1
34095840 10.1039/d0md00097c ADMET 1
34095840 10.1039/d0md00097c LLC-MK2 1
34095840 10.1039/d0md00097c Trypanosoma cruzi 1
34095840 10.1039/d0md00097c Cruzipain 1
31561938 10.1016/j.bmc.2019.115083 Trypanosoma cruzi 1
31561938 10.1016/j.bmc.2019.115083 No relevant target 1
31561938 10.1016/j.bmc.2019.115083 Procathepsin L 1

Data from ChEMBL 36 via Core Engine