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Compound Detail

CHEMBL3980860

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O=C1NC(=O)[C@](CNC(=O)[C@@H](Cc2ccc(C(F)(F)F)cc2)C2CC2)(C2CC2)N1

Basic Information

ChEMBL ID CHEMBL3980860
Phase Preclinical
Structure Type MOL
InChI Key JHOUEQAOHDTLPY-KXBFYZLASA-N
11
Targets
21
Activities
1
Assay Types
10
PK Parameters
12
Publications
0
Known Names

Molecular Properties

409.4
MW (Da)
2.38
ALogP
3
HBA
3
HBD
87.3
PSA (Ų)
0.60
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 C20H22F3N3O3
MW 409.41
Aromatic Rings 1
Heavy Atoms 29
NP-Likeness -0.46

Activity Summary

IC50 21 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A disintegrin and metalloproteinase with thrombospondin motifs 5
CHEMBL2285
IC50 8.7 8.4625 2.0 4
A disintegrin and metalloproteinase with thrombospondin motifs 4
CHEMBL2318
IC50 8.7 8.7 2.0 3
ADAM metallopeptidase with thrombospondin type 1 motif 4
CHEMBL3988592
IC50 8.7 7.85 2.0 2
A disintegrin-like and metallopeptidase (Reprolysin type) with thrombospondin type 1 motif, 5 (Aggrecanase-2)
CHEMBL3988600
IC50 7.75 7.75 18.0 1
Macrophage metalloelastase
CHEMBL4393
IC50 6.57 6.57 268.0 2
Neutrophil collagenase
CHEMBL4588
IC50 6.09 6.09 804.0 1
72 kDa type IV collagenase
CHEMBL333
IC50 4.46 4.46 35000.0 2
Interstitial collagenase
CHEMBL332
IC50 4.41 4.41 39200.0 1
Collagenase 3
CHEMBL280
IC50 4.33 4.33 46952.0 2
Matrix metalloproteinase-14
CHEMBL3869
IC50 4.3 4.3 50000.0 2
Stromelysin-1
CHEMBL283
IC50 4.0 4.0 99710.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 532.23 ng.hr.mL-1 Rattus norvegicus
AUC 9007.02 ng.hr.mL-1 Rattus norvegicus
CL 33.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 1600.0 nM Rattus norvegicus
Cmax 6600.0 nM Rattus norvegicus
F 100.0 % Rattus norvegicus
T1/2 1.5 hr Rattus norvegicus
T1/2 2.6 hr Rattus norvegicus
Tmax 0.5 hr Rattus norvegicus
Vd 4.3 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 2.0 nM 8.7 AlphaScreen Assay: The compounds of the present invention can be evaluated by us... -
ADAM metallopeptidase with thrombospondin type 1 motif 4 IC50 = 2.0 nM 8.7 AlphaScreen Assay: The compounds of the present invention can be evaluated by us... -
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 2.0 nM 8.7 Inhibition of human ADAMTS4 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG pe... 28613895
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 2.0 nM 8.7 Inhibition of human ADAMTS5 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG pe... 28613895
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 2.0 nM 8.7 Inhibition of human recombinant ADAMTS5 using synthetic peptide as substrate by ... 33719441
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 2.0 nM 8.7 Inhibition of human recombinant ADAMTS4 using synthetic peptide as substrate by ... 33719441
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 2.0 nM 8.7 AlphaScreen Assay: The compounds of the present invention can be evaluated by us... -
A disintegrin-like and metallopeptidase (Reprolysin type) with thrombospondin type 1 motif, 5 (Aggrecanase-2) IC50 = 18.0 nM 7.75 Shift AlphaScreen Assay : The AlphaScreen Assay is modified to include the testi... -
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 18.0 nM 7.75 Inhibition of human ADAMTS5 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG pe... 28613895
ADAM metallopeptidase with thrombospondin type 1 motif 4 IC50 = 101.0 nM 7.0 Shift AlphaScreen Assay : The AlphaScreen Assay is modified to include the testi... -
Macrophage metalloelastase IC50 = 268.0 nM 6.57 In Vitro Fluorescence Assay: A continuous assay is used in which the substrate i... -
Macrophage metalloelastase IC50 = 270.0 nM 6.57 Inhibition of human MMP12 using Mca-PQGL-(3-[2, 4-dinitrophenyl]-L-2, 3-diaminop... 28613895
Neutrophil collagenase IC50 = 804.0 nM 6.09 In Vitro Fluorescence Assay: A continuous assay is used in which the substrate i... -
72 kDa type IV collagenase IC50 = 35000.0 nM 4.46 In Vitro Fluorescence Assay: A continuous assay is used in which the substrate i... -
72 kDa type IV collagenase IC50 = 35000.0 nM 4.46 Inhibition of human MMP2 using Mca-PQGL-(3-[2, 4-dinitrophenyl]-L-2, 3-diaminopr... 28613895
Interstitial collagenase IC50 = 39200.0 nM 4.41 In Vitro Fluorescence Assay: A continuous assay is used in which the substrate i... -
Collagenase 3 IC50 = 46952.0 nM 4.33 In Vitro Fluorescence Assay: A continuous assay is used in which the substrate i... -
Collagenase 3 IC50 = 47000.0 nM 4.33 Inhibition of human MMP13 using Mca-PQGL-(3-[2, 4-dinitrophenyl]-L-2, 3-diaminop... 28613895
Matrix metalloproteinase-14 IC50 = 50200.0 nM 4.3 In Vitro Fluorescence Assay: A continuous assay is used in which the substrate i... -
Matrix metalloproteinase-14 IC50 = 50000.0 nM 4.3 Inhibition of human MMP14 using Mca-PQGL-(3-[2, 4-dinitrophenyl]-L-2, 3-diaminop... 28613895

Literature References

PubMed DOI Target Context # Activities
28613895 10.1021/acs.jmedchem.7b00650 Rattus norvegicus 14
28613895 10.1021/acs.jmedchem.7b00650 A disintegrin and metalloproteinase with thrombospondin motifs 5 2
28613895 10.1021/acs.jmedchem.7b00650 Plasma 2
28613895 10.1021/acs.jmedchem.7b00650 A disintegrin and metalloproteinase with thrombospondin motifs 4 1
28613895 10.1021/acs.jmedchem.7b00650 72 kDa type IV collagenase 1
28613895 10.1021/acs.jmedchem.7b00650 Stromelysin-1 1
28613895 10.1021/acs.jmedchem.7b00650 Macrophage metalloelastase 1
28613895 10.1021/acs.jmedchem.7b00650 Collagenase 3 1
28613895 10.1021/acs.jmedchem.7b00650 Matrix metalloproteinase-14 1
28613895 10.1021/acs.jmedchem.7b00650 Unchecked 1
33719441 10.1021/acs.jmedchem.0c02008 A disintegrin and metalloproteinase with thrombospondin motifs 5 1
33719441 10.1021/acs.jmedchem.0c02008 A disintegrin and metalloproteinase with thrombospondin motifs 4 1

Data from ChEMBL 36 via Core Engine