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Compound Detail

CHEMBL184514

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CC(C)C[C@@H](C(=O)NCC#N)c1cccc(-c2ccc(N3CCNCC3)cc2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL184514
Phase Preclinical
Structure Type MOL
InChI Key AQPCFTUFFUSBNZ-HSZRJFAPSA-N
9
Targets
31
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

390.5
MW (Da)
3.53
ALogP
4
HBA
2
HBD
68.2
PSA (Ų)
0.71
QED
0
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H30N4O
MW 390.53
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness -0.93

Activity Summary

IC50 27 meas. best 8.52
Ki 4 meas. best 8.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Cathepsin K
CHEMBL268
 IC50 8.52 8.2775 3.0 4
Cathepsin K
CHEMBL268
 Ki 8.1 8.1 8.0 1
Cathepsin K
CHEMBL3349
 IC50 7.96 7.72 11.0 2
Osteoclast
CHEMBL612548
 IC50 7.02 6.925 95.0 2
Bos taurus
CHEMBL613489
 IC50 7.02 7.02 95.0 1
Procathepsin L
CHEMBL3837
 IC50 6.5 5.674 320.0 5
Cathepsin S
CHEMBL4098
 IC50 6.13 5.3 740.0 2
Cathepsin S
CHEMBL2954
 IC50 5.87 5.534 1340.0 5
Cathepsin S
CHEMBL2954
 Ki 5.77 5.77 1695.0 1
Cathepsin B
CHEMBL4072
 Ki 5.42 5.42 3843.0 1
Cathepsin B
CHEMBL4072
 IC50 5.4 5.126 3950.0 5
Procathepsin L
CHEMBL3837
 Ki 5.33 5.33 4641.0 1
A20
CHEMBL613850
 IC50 5.07 5.07 8600.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 98.0 mL.min-1.kg-1 Rattus norvegicus
MRT 2.583 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Cathepsin K IC50 = 3.0 nM 8.52 Inhibitory concentration against human cathepsin K 15261289
Cathepsin K IC50 = 3.0 nM 8.52 In vitro inhibitory activity against human cathepsin K, using 2 uM of Z -Leu-Arg... 12904076
Cathepsin K IC50 = 7.8 nM 8.11 Inhibitory activity against humanized rabbit cathepsin K 16302795
Cathepsin K Ki = 8.0 nM 8.1 Inhibition of human cathepsin K 16750630
Cathepsin K IC50 = 11.0 nM 7.96 Inhibitory activity against cathepsin K using humanized rabbit enzyme 16154747
Cathepsin K IC50 = 11.0 nM 7.96 Inhibitory concentration against humanized rabbit cathepsin K 15261289
Cathepsin K IC50 = 33.0 nM 7.48 Inhibitory activity against rabbit cathepsin K 16302795
Bos taurus IC50 = 95.0 nM 7.02 In vitro Bone resorption; measuring degradation of bovine bone by isolated osteo... 12904076
Osteoclast IC50 = 95.0 nM 7.02 Effect on degradation of bovine bone by rabbit osteoclast 16750630
Osteoclast IC50 = 149.0 nM 6.83 Effect of compound on degradation of collagen in osteoclast bone resorption assa... 16302795
Procathepsin L IC50 = 320.0 nM 6.5 Inhibitory activity against human cathepsin L expressed in HepG2 cells 16302795
Cathepsin S IC50 = 740.0 nM 6.13 Inhibitory activity against mouse cathepsin S in mouse splenocytes 16302795
Cathepsin S IC50 = 1340.0 nM 5.87 Inhibitory activity against human cathepsin S expressed in ramos cells 16302795
Cathepsin S Ki = 1695.0 nM 5.77 Inhibition of human cathepsin S 16750630
Cathepsin S IC50 = 2010.0 nM 5.7 In vitro inhibitory activity against human cathepsin S, using 2 uM of Z -Leu-Arg... 12904076
Cathepsin S IC50 = 2010.0 nM 5.7 Inhibitory concentration against human cathepsin S 15261289
Cathepsin S IC50 = 2010.0 nM 5.7 Inhibitory activity against cathepsin S from human 16154747
Procathepsin L IC50 = 2600.0 nM 5.58 Inhibitory activity against human cathepsin L 16302795
Procathepsin L IC50 = 3725.0 nM 5.43 Inhibitory activity against cathepsin L from human 16154747
Procathepsin L IC50 = 3725.0 nM 5.43 Inhibitory concentration against human cathepsin L 15261289

Literature References

PubMed DOI Target Context # Activities
16302795 10.1021/jm0504961 Cathepsin S 4
16750630 10.1016/j.bmcl.2006.05.061 Rattus norvegicus 3
16302795 10.1021/jm0504961 No relevant target 2
15261289 10.1016/j.bmcl.2004.05.087 Cathepsin K 2
16302795 10.1021/jm0504961 Procathepsin L 2
16302795 10.1021/jm0504961 Cathepsin B 2
16302795 10.1021/jm0504961 Cathepsin K 2
16154747 10.1016/j.bmcl.2005.07.071 Cathepsin K 1
16750630 10.1016/j.bmcl.2006.05.061 Cathepsin K 1
16154747 10.1016/j.bmcl.2005.07.071 Cathepsin S 1
16154747 10.1016/j.bmcl.2005.07.071 Procathepsin L 1
16154747 10.1016/j.bmcl.2005.07.071 Cathepsin B 1
12904076 10.1021/jm0301078 Cathepsin K 1
15261289 10.1016/j.bmcl.2004.05.087 Unchecked 1
15261289 10.1016/j.bmcl.2004.05.087 Cathepsin S 1
15261289 10.1016/j.bmcl.2004.05.087 Procathepsin L 1
15261289 10.1016/j.bmcl.2004.05.087 Cathepsin B 1
12904076 10.1021/jm0301078 Bos taurus 1
12904076 10.1021/jm0301078 Cathepsin B 1
12904076 10.1021/jm0301078 Cathepsin S 1

Data from ChEMBL 36 via Core Engine