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Compound Detail

CHEMBL148169

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Cc1cc(COc2ccc([C@]3(C)CCN([C@H](C)C(=O)NO)C3=O)cc2)c2ccccc2n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL148169
Phase Preclinical
Structure Type MOL
InChI Key YDMIPBHQKFOFQW-NSYGIPOTSA-N
14
Targets
43
Activities
2
Assay Types
13
PK Parameters
20
Publications
0
Known Names

Molecular Properties

433.5
MW (Da)
3.51
ALogP
5
HBA
2
HBD
91.8
PSA (Ų)
0.46
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C25H27N3O4
MW 433.51
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.62

Activity Summary

Ki 29 meas. best 10.22
IC50 14 meas. best 9.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 Ki 10.22 10.22 0.1 1
Unchecked
CHEMBL612545
 IC50 9.46 7.96 0.3 2
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 9.46 8.695 0.3 6
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3332
 Ki 9.25 9.25 0.6 3
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3332
 IC50 9.0 9.0 1.0 1
Disintegrin and metalloproteinase domain-containing protein 33
CHEMBL6121
 Ki 7.82 7.82 15.0 1
Stromelysin-1
CHEMBL283
 IC50 6.85 6.85 141.0 1
Stromelysin-1
CHEMBL283
 Ki 6.85 6.85 141.0 3
Neutrophil collagenase
CHEMBL4588
 Ki 6.59 6.59 257.0 2
Matrilysin
CHEMBL4073
 Ki 6.59 6.59 259.0 3
Collagenase 3
CHEMBL280
 IC50 5.85 5.85 1417.0 1
Collagenase 3
CHEMBL280
 Ki 5.85 5.85 1417.0 3
Matrix metalloproteinase-16
CHEMBL2200
 Ki 5.8 5.8 1599.0 2
72 kDa type IV collagenase
CHEMBL333
 Ki 5.69 5.69 2050.0 3
72 kDa type IV collagenase
CHEMBL333
 IC50 5.69 5.69 2050.0 1
Matrix metalloproteinase-15
CHEMBL2963
 Ki 5.4 5.4 3997.0 2
Matrix metalloproteinase-9
CHEMBL321
 Ki 4.99 4.99 10340.0 2
Matrix metalloproteinase-9
CHEMBL321
 IC50 4.99 4.99 10340.0 1
Matrix metalloproteinase-14
CHEMBL3869
 Ki 4.8 4.8 15872.0 2
Interstitial collagenase
CHEMBL332
 Ki 4.52 4.52 30000.0 2
Interstitial collagenase
CHEMBL332
 IC50 4.52 4.52 30000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1808.17 ng.hr.mL-1 Rattus norvegicus
AUC 4426.14 ng.hr.mL-1 Canis lupus familiaris
CL 35.0 mL.min-1.kg-1 Rattus norvegicus
CL 15.67 mL.min-1.kg-1 Canis lupus familiaris
F 41.0 % Rattus norvegicus
F 32.0 % Canis lupus familiaris
F 32.0 % Canis lupus familiaris
F 41.0 % Rattus norvegicus
Fu 0.036 - Homo sapiens
T1/2 11.8 - Rattus norvegicus
T1/2 7.1 - Canis lupus familiaris
Tmax 0.38 hr Rattus norvegicus
Tmax 0.38 hr Canis lupus familiaris

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Disintegrin and metalloproteinase domain-containing protein 17 Ki = 0.06 nM 10.22 Inhibition of TACE catalytic domain by FRET assay 19054672
Unchecked IC50 = 0.35 nM 9.46 Inhibition of LPS-stimulated TNFalpha production in whole blood 18790648
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 0.35 nM 9.46 Inhibition of Tumor necrosis factor alpha secretion in LPS-stimulated human whol... 12408705
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 0.56 nM 9.25 Inhibition of TACE 17064892
Disintegrin and metalloproteinase domain-containing protein 17 Ki = 0.56 nM 9.25 Affinity for Tumor necrosis factor alpha converting enzyme (TACE) 12408705
Disintegrin and metalloproteinase domain-containing protein 17 Ki = 0.56 nM 9.25 Inhibition of pig TACE 18790648
Disintegrin and metalloproteinase domain-containing protein 17 Ki = 0.56 nM 9.25 Inhibition of porcine TACE 34624823
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 1.0 nM 9.0 Inhibitory activity against porcine Tumor necrosis factor alpha converting enzym... 12408705
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 1.0 nM 9.0 Inhibition of pTACE 17368021
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 1.0 nM 9.0 Inhibition of TACE 19095454
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 1.0 nM 9.0 Inhibition of TACE 19095454
Disintegrin and metalloproteinase domain-containing protein 33 Ki = 15.0 nM 7.82 Inhibition of ADAM33 18790648
Stromelysin-1 Ki = 141.0 nM 6.85 Inhibition of MMP3 18790648
Stromelysin-1 Ki = 141.0 nM 6.85 Affinity for Matrix metalloprotease-3 (MMP-3) 12408705
Stromelysin-1 Ki = 141.0 nM 6.85 Binding affinity to MMP3 17368021
Stromelysin-1 IC50 = 141.0 nM 6.85 Inhibition of MMP3 17064892
Matrilysin Ki = 259.0 nM 6.59 Inhibition of MMP7 18790648
Matrilysin Ki = 259.0 nM 6.59 Affinity for Matrix metalloprotease-7 (MMP-7) 12408705
Neutrophil collagenase Ki = 257.0 nM 6.59 Affinity for Matrix metalloprotease-8 (MMP-8) 12408705
Neutrophil collagenase Ki = 257.0 nM 6.59 Inhibition of MMP8 18790648

Literature References

PubMed DOI Target Context # Activities
12408705 10.1021/jm0255670 Canis familiaris 6
12408705 10.1021/jm0255670 Rattus norvegicus 6
12408705 10.1021/jm0255670 Disintegrin and metalloproteinase domain-containing protein 17 4
19095454 10.1016/j.bmc.2008.11.067 Disintegrin and metalloproteinase domain-containing protein 17 2
12408705 10.1021/jm0255670 Matrix metalloproteinase-16 1
34624823 10.1016/j.ejmech.2021.113877 Disintegrin and metalloproteinase domain-containing protein 17 1
17064892 10.1016/j.bmcl.2006.10.004 Disintegrin and metalloproteinase domain-containing protein 17 1
17368021 10.1016/j.bmcl.2007.02.076 Collagenase 3 1
17368021 10.1016/j.bmcl.2007.02.076 Matrilysin 1
17368021 10.1016/j.bmcl.2007.02.076 Stromelysin-1 1
17368021 10.1016/j.bmcl.2007.02.076 72 kDa type IV collagenase 1
17368021 10.1016/j.bmcl.2007.02.076 Disintegrin and metalloproteinase domain-containing protein 17 1
12408705 10.1021/jm0255670 Matrix metalloproteinase-15 1
12408705 10.1021/jm0255670 Matrix metalloproteinase-14 1
12408705 10.1021/jm0255670 Collagenase 3 1
12408705 10.1021/jm0255670 Matrix metalloproteinase-9 1
12408705 10.1021/jm0255670 Neutrophil collagenase 1
12408705 10.1021/jm0255670 Matrilysin 1
12408705 10.1021/jm0255670 Stromelysin-1 1
12408705 10.1021/jm0255670 72 kDa type IV collagenase 1

Data from ChEMBL 36 via Core Engine