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Compound Detail

CHEMBL489100

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

Basic Information

ChEMBL ID CHEMBL489100
Phase Preclinical
Structure Type MOL
InChI Key QVNZBDLTUKCPGJ-SHQCIBLASA-N
12
Targets
13
Activities
1
Assay Types
9
PK Parameters
19
Publications
0
Known Names

Molecular Properties

476.6
MW (Da)
3.43
ALogP
6
HBA
3
HBD
117.8
PSA (Ų)
0.34
QED
0
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H32N4O4
MW 476.58
Aromatic Rings 3
Heavy Atoms 35
NP-Likeness -0.48

Activity Summary

IC50 13 meas. best 9.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 9.7 8.81 0.2 2
Whole blood
CHEMBL2367389
 IC50 7.22 7.22 60.0 1
Unchecked
CHEMBL612545
 IC50 7.05 7.05 90.0 1
Stromelysin-1
CHEMBL283
 IC50 6.54 6.54 285.0 1
Neutrophil collagenase
CHEMBL4588
 IC50 6.52 6.52 299.0 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 6.41 6.41 389.0 1
Interstitial collagenase
CHEMBL332
 IC50 6.37 6.37 429.0 1
Collagenase 3
CHEMBL280
 IC50 6.34 6.34 461.0 1
Matrilysin
CHEMBL4073
 IC50 6.33 6.33 466.0 1
72 kDa type IV collagenase
CHEMBL333
 IC50 6.32 6.32 482.0 1
Disintegrin and metalloproteinase domain-containing protein 10
CHEMBL5028
 IC50 6.32 6.32 480.0 1
Matrix metalloproteinase-14
CHEMBL3869
 IC50 6.3 6.3 499.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 32356.0 ng.hr.mL-1 Rattus norvegicus
AUC 5970.0 ng.hr.mL-1 Rattus norvegicus
F 54.0 % Canis lupus familiaris
F 16.0 % Rattus norvegicus
F 18.45 % Rattus norvegicus
T1/2 3.0 hr Homo sapiens
T1/2 2.69 hr Rattus norvegicus
T1/2 8.67 hr Rattus norvegicus
Tmax 1.21 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 0.2 nM 9.7 Inhibition of TACE 19095454
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 12.0 nM 7.92 Inhibition of human catalytic domain of TACE assessed as inhibit the cleavage of... -
Whole blood IC50 = 60.0 nM 7.22 Antiinflammatory activity in human whole blood assessed as inhibition of LPS-ind... -
Unchecked IC50 = 90.0 nM 7.05 Inhibition of TNFalpha production in whole blood 19095454
Stromelysin-1 IC50 = 285.0 nM 6.54 Inhibition of MMP3 (unknown origin) by fluorescence-based FRET assay -
Neutrophil collagenase IC50 = 299.0 nM 6.52 Inhibition of MMP8 (unknown origin) by fluorescence-based FRET assay -
Matrix metalloproteinase-9 IC50 = 389.0 nM 6.41 Inhibition of MMP9 (unknown origin) by fluorescence-based FRET assay -
Interstitial collagenase IC50 = 429.0 nM 6.37 Inhibition of MMP1 (unknown origin) by fluorescence-based FRET assay -
Collagenase 3 IC50 = 461.0 nM 6.34 Inhibition of MMP13 (unknown origin) by fluorescence-based FRET assay -
Matrilysin IC50 = 466.0 nM 6.33 Inhibition of MMP7 (unknown origin) by fluorescence-based FRET assay -
Disintegrin and metalloproteinase domain-containing protein 10 IC50 = 480.0 nM 6.32 Inhibition of ADAM10 (unknown origin) using fluorescent substrate by fluorescenc... -
72 kDa type IV collagenase IC50 = 482.0 nM 6.32 Inhibition of MMP2 (unknown origin) by fluorescence-based FRET assay -
Matrix metalloproteinase-14 IC50 = 499.0 nM 6.3 Inhibition of MMP14 (unknown origin) by fluorescence-based FRET assay -

Literature References

PubMed DOI Target Context # Activities
- 10.1039/C0MD00261E Rattus norvegicus 23
- 10.1039/C0MD00261E Disintegrin and metalloproteinase domain-containing protein 17 2
- 10.1039/C0MD00261E Interstitial collagenase 1
- 10.1039/C0MD00261E Mus musculus 1
- 10.1039/C0MD00261E Matrix metalloproteinase-14 1
- 10.1039/C0MD00261E Collagenase 3 1
- 10.1039/C0MD00261E Matrix metalloproteinase-9 1
- 10.1039/C0MD00261E Neutrophil collagenase 1
- 10.1039/C0MD00261E Matrilysin 1
- 10.1039/C0MD00261E Stromelysin-1 1
- 10.1039/C0MD00261E 72 kDa type IV collagenase 1
19095454 10.1016/j.bmc.2008.11.067 Disintegrin and metalloproteinase domain-containing protein 17 1
- 10.1039/C0MD00261E Disintegrin and metalloproteinase domain-containing protein 10 1
- 10.1039/C0MD00261E Whole blood 1
19095454 10.1016/j.bmc.2008.11.067 Homo sapiens 1
19095454 10.1016/j.bmc.2008.11.067 Rattus norvegicus 1
19095454 10.1016/j.bmc.2008.11.067 Canis familiaris 1
19095454 10.1016/j.bmc.2008.11.067 Mus musculus 1
19095454 10.1016/j.bmc.2008.11.067 Unchecked 1

Data from ChEMBL 36 via Core Engine