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Compound Detail

CHEMBL1082381

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C#CCN1CCC(C(=O)NO)(S(=O)(=O)c2ccc(Sc3ccccc3)cc2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1082381
Phase Preclinical
Structure Type MOL
InChI Key WXNWNNKHEJMQOM-UHFFFAOYSA-N
7
Targets
18
Activities
1
Assay Types
5
PK Parameters
20
Publications
0
Known Names

Molecular Properties

430.6
MW (Da)
2.58
ALogP
6
HBA
2
HBD
86.7
PSA (Ų)
0.42
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C21H22N2O4S2
MW 430.55
Aromatic Rings 2
Heavy Atoms 29
NP-Likeness -1.17

Activity Summary

IC50 18 meas. best 9.48

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
72 kDa type IV collagenase
CHEMBL333
 IC50 9.48 9.48 0.3 3
Collagenase 3
CHEMBL280
 IC50 9.4 9.4 0.4 2
Matrix metalloproteinase-9
CHEMBL321
 IC50 8.82 8.82 1.5 3
Neutrophil collagenase
CHEMBL4588
 IC50 8.74 8.74 1.8 3
Matrix metalloproteinase-14
CHEMBL3869
 IC50 8.1 7.8467 8.0 3
Stromelysin-1
CHEMBL283
 IC50 7.89 7.89 13.0 2
Interstitial collagenase
CHEMBL332
 IC50 5.06 5.06 8660.0 2

Pharmacokinetic Data

Parameter Value Units Species
Cmax 31657.18 nM Rattus norvegicus
F 28.0 % Rattus norvegicus
F 28.0 % Rattus norvegicus
T1/2 1.1 hr Rattus norvegicus
T1/2 1.1 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
72 kDa type IV collagenase IC50 = 0.33 nM 9.48 Inhibition of human MMP2 21493063
72 kDa type IV collagenase IC50 = 0.33 nM 9.48 Inhibition of human MMP2 assessed as cleavage of fluorogenic peptide MCAPro-Leu-... 20726512
72 kDa type IV collagenase IC50 = 0.33 nM 9.48 Inhibition of MMP2 20529684
Collagenase 3 IC50 = 0.4 nM 9.4 Inhibition of MMP13 20529684
Collagenase 3 IC50 = 0.4 nM 9.4 Inhibition of human MMP13 assessed as cleavage of fluorogenic peptide MCAPro-Leu... 20726512
Matrix metalloproteinase-9 IC50 = 1.5 nM 8.82 Inhibition of MMP9 20529684
Matrix metalloproteinase-9 IC50 = 1.5 nM 8.82 Inhibition of human MMP9 21493063
Matrix metalloproteinase-9 IC50 = 1.5 nM 8.82 Inhibition of human MMP9 assessed as cleavage of fluorogenic peptide MCAPro-Leu-... 20726512
Neutrophil collagenase IC50 = 1.8 nM 8.74 Inhibition of human MMP8 21493063
Neutrophil collagenase IC50 = 1.8 nM 8.74 Inhibition of human MMP8 assessed as cleavage of fluorogenic peptide MCAPro-Leu-... 20726512
Neutrophil collagenase IC50 = 1.8 nM 8.74 Inhibition of MMP8 20529684
Matrix metalloproteinase-14 IC50 = 8.0 nM 8.1 Inhibition of human MMP14 21493063
Stromelysin-1 IC50 = 13.0 nM 7.89 Inhibition of MMP3 20529684
Stromelysin-1 IC50 = 13.0 nM 7.89 Inhibition of human MMP3 assessed as cleavage of fluorogenic peptide MCAPro-Leu-... 20726512
Matrix metalloproteinase-14 IC50 = 19.0 nM 7.72 Inhibition of MMP14 20529684
Matrix metalloproteinase-14 IC50 = 19.1 nM 7.72 Inhibition of human MMP14 assessed as cleavage of fluorogenic peptide MCAPro-Leu... 20726512
Interstitial collagenase IC50 = 8660.0 nM 5.06 Inhibition of MMP1 20529684
Interstitial collagenase IC50 = 8660.0 nM 5.06 Inhibition of human MMP1 expressed in human HT-1080 cells assessed as cleavage o... 20726512

Literature References

PubMed DOI Target Context # Activities
20726512 10.1021/jm100669j Rattus norvegicus 4
20529684 10.1016/j.bmcl.2010.04.130 Rattus norvegicus 2
21493063 10.1016/j.bmcl.2011.03.095 Neutrophil collagenase 1
20726512 10.1021/jm100669j MX1 1
20726512 10.1021/jm100669j Neutrophil collagenase 1
20726512 10.1021/jm100669j Matrix metalloproteinase-9 1
20726512 10.1021/jm100669j Collagenase 3 1
20726512 10.1021/jm100669j Matrix metalloproteinase-14 1
21493063 10.1016/j.bmcl.2011.03.095 Matrix metalloproteinase-14 1
21493063 10.1016/j.bmcl.2011.03.095 Interstitial collagenase 1
21493063 10.1016/j.bmcl.2011.03.095 Collagenase 3 1
21493063 10.1016/j.bmcl.2011.03.095 Matrix metalloproteinase-9 1
20529684 10.1016/j.bmcl.2010.04.130 72 kDa type IV collagenase 1
21493063 10.1016/j.bmcl.2011.03.095 72 kDa type IV collagenase 1
20529684 10.1016/j.bmcl.2010.04.130 Neutrophil collagenase 1
20529684 10.1016/j.bmcl.2010.04.130 Matrilysin 1
20529684 10.1016/j.bmcl.2010.04.130 Stromelysin-1 1
20529684 10.1016/j.bmcl.2010.04.130 Interstitial collagenase 1
20529684 10.1016/j.bmcl.2010.04.130 Matrix metalloproteinase-14 1
20529684 10.1016/j.bmcl.2010.04.130 Collagenase 3 1

Data from ChEMBL 36 via Core Engine