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Compound Detail

CHEMBL497985

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CN1CC2(CC2)C[C@H](C(=O)NO)[C@H]1C(=O)N1CCN(c2ccc(C(F)(F)F)cn2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL497985
Phase Preclinical
Structure Type MOL
InChI Key HJNKYGBTSGQBDU-HOCLYGCPSA-N
12
Targets
14
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

441.4
MW (Da)
1.35
ALogP
6
HBA
2
HBD
89.0
PSA (Ų)
0.54
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C20H26F3N5O3
MW 441.45
Aromatic Rings 1
Heavy Atoms 31
NP-Likeness -0.97

Activity Summary

Ki 10 meas. best 8.86
IC50 4 meas. best 7.01

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
72 kDa type IV collagenase
CHEMBL333
 Ki 8.86 8.86 1.4 1
Neutrophil collagenase
CHEMBL4588
 Ki 8.52 8.52 3.0 1
Matrix metalloproteinase-9
CHEMBL321
 Ki 7.98 7.98 10.4 1
Macrophage metalloelastase
CHEMBL4393
 Ki 7.53 7.53 29.5 1
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 Ki 7.21 7.21 61.0 1
Matrix metalloproteinase-14
CHEMBL3869
 Ki 7.17 7.17 67.6 1
Matrilysin
CHEMBL4073
 Ki 7.12 7.12 75.0 1
Disintegrin and metalloproteinase domain-containing protein 10
CHEMBL5028
 IC50 7.01 7.01 97.0 1
Interstitial collagenase
CHEMBL332
 Ki 6.46 6.46 348.0 1
Stromelysin-1
CHEMBL283
 Ki 6.32 6.32 484.0 1
Macrophage metalloelastase
CHEMBL4393
 IC50 6.25 6.25 564.0 1
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 5.69 5.69 2045.0 1
Disintegrin and metalloproteinase domain-containing protein 9
CHEMBL5982
 Ki 5.66 5.66 2200.0 1
Disintegrin and metalloproteinase domain-containing protein 33
CHEMBL6121
 IC50 5.38 5.38 4125.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
72 kDa type IV collagenase Ki = 1.37 nM 8.86 Inhibition of APMA activated recombinant human full length MMP2 expressed in mou... 30034605
Neutrophil collagenase Ki = 3.01 nM 8.52 Inhibition of recombinant human MMP8 catalytic domain (Phe99 to Gln269 residues)... 30034605
Matrix metalloproteinase-9 Ki = 10.4 nM 7.98 Inhibition of recombinant human MMP9 catalytic domain (Phe107 to Pro449 residues... 30034605
Macrophage metalloelastase Ki = 29.5 nM 7.53 Inhibition of recombinant human MMP12 catalytic domain using Mca-PLGL-DpaAR-NH2 ... 30034605
Disintegrin and metalloproteinase domain-containing protein 17 Ki = 61.0 nM 7.21 Inhibition of recombinant human C-terminal His6-tagged ADAM17 (Arg215 to Asn671 ... 30034605
Matrix metalloproteinase-14 Ki = 67.6 nM 7.17 Inhibition of recombinant human MMP14 catalytic domain (89 to 265 residues) expr... 30034605
Matrilysin Ki = 75.0 nM 7.12 Inhibition of recombinant human MMP7 expressed in Escherichia coli using MOCAc-P... 30034605
Disintegrin and metalloproteinase domain-containing protein 10 IC50 = 97.0 nM 7.01 Inhibition of ADAM10 18790648
Interstitial collagenase Ki = 348.0 nM 6.46 Inhibition of recombinant human MMP1 catalytic domain (Phe100 to Gln268 residues... 30034605
Stromelysin-1 Ki = 484.0 nM 6.32 Inhibition of recombinant human MMP3 catalytic domain expressed in Escherichia c... 30034605
Macrophage metalloelastase IC50 = 564.0 nM 6.25 Inhibition of MMP12 18790648
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 2045.0 nM 5.69 Inhibition of TACE 18790648
Disintegrin and metalloproteinase domain-containing protein 9 Ki = 2200.0 nM 5.66 Inhibition of recombinant human C-terminal His10-tagged ADAM9 (Ala206 to Asp697 ... 30034605
Disintegrin and metalloproteinase domain-containing protein 33 IC50 = 4125.0 nM 5.38 Inhibition of ADAM33 18790648

Literature References

PubMed DOI Target Context # Activities
18790648 10.1016/j.bmc.2008.08.058 Disintegrin and metalloproteinase domain-containing protein 9 1
30034605 10.1021/acsmedchemlett.8b00163 Disintegrin and metalloproteinase domain-containing protein 17 1
30034605 10.1021/acsmedchemlett.8b00163 Matrix metalloproteinase-14 1
30034605 10.1021/acsmedchemlett.8b00163 Macrophage metalloelastase 1
30034605 10.1021/acsmedchemlett.8b00163 Matrix metalloproteinase-9 1
30034605 10.1021/acsmedchemlett.8b00163 Neutrophil collagenase 1
30034605 10.1021/acsmedchemlett.8b00163 Matrilysin 1
30034605 10.1021/acsmedchemlett.8b00163 Stromelysin-1 1
30034605 10.1021/acsmedchemlett.8b00163 72 kDa type IV collagenase 1
30034605 10.1021/acsmedchemlett.8b00163 Interstitial collagenase 1
18790648 10.1016/j.bmc.2008.08.058 Disintegrin and metalloproteinase domain-containing protein 17 1
18790648 10.1016/j.bmc.2008.08.058 72 kDa type IV collagenase 1
18790648 10.1016/j.bmc.2008.08.058 Matrilysin 1
18790648 10.1016/j.bmc.2008.08.058 Disintegrin and metalloproteinase domain-containing protein 10 1
18790648 10.1016/j.bmc.2008.08.058 Disintegrin and metalloproteinase domain-containing protein 33 1
18790648 10.1016/j.bmc.2008.08.058 Matrix metalloproteinase-15 1
18790648 10.1016/j.bmc.2008.08.058 Macrophage metalloelastase 1
18790648 10.1016/j.bmc.2008.08.058 Matrix metalloproteinase-14 1
18790648 10.1016/j.bmc.2008.08.058 Matrix metalloproteinase-9 1
18790648 10.1016/j.bmc.2008.08.058 Stromelysin-1 1

Data from ChEMBL 36 via Core Engine