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Compound Detail

CHEMBL3358158

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Cn1ccnc1[C@]1(CNC(=O)c2cc3cc(C(F)(F)F)ccc3o2)NC(=O)NC1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3358158
Phase Preclinical
Structure Type MOL
InChI Key PDBQNZHFRVAZBC-KRWDZBQOSA-N
10
Targets
19
Activities
1
Assay Types
23
PK Parameters
20
Publications
0
Known Names

Molecular Properties

421.3
MW (Da)
1.65
ALogP
6
HBA
3
HBD
118.3
PSA (Ų)
0.55
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C18H14F3N5O4
MW 421.34
Aromatic Rings 3
Heavy Atoms 30
NP-Likeness -1.20

Activity Summary

IC50 19 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A disintegrin and metalloproteinase with thrombospondin motifs 5
CHEMBL2285
 IC50 8.4 7.93 4.0 4
A disintegrin and metalloproteinase with thrombospondin motifs 4
CHEMBL2318
 IC50 8.4 8.4 4.0 2
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 5.0 5.0 10000.0 2
72 kDa type IV collagenase
CHEMBL333
 IC50 4.96 4.96 11000.0 2
Collagenase 3
CHEMBL280
 IC50 4.52 4.52 30000.0 2
Matrix metalloproteinase-9
CHEMBL321
 IC50 4.19 4.19 65000.0 1
Stromelysin-1
CHEMBL283
 IC50 4.16 4.16 69000.0 2
Matrix metalloproteinase-14
CHEMBL3869
 IC50 4.07 4.07 86000.0 2
Interstitial collagenase
CHEMBL332
 IC50 4.0 4.0 100000.0 1
Matrilysin
CHEMBL4073
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 8500.0 ng.hr.mL-1 Rattus norvegicus
AUC 8426.8 ng.hr.mL-1 Rattus norvegicus
CL 4.8 mL.min-1.kg-1 Rattus norvegicus
CL 4.8 mL.min-1.kg-1 Rattus norvegicus
CL 4.8 mL.min-1.kg-1 Canis lupus familiaris
CL 7.3 mL.min-1.kg-1 Macaca fascicularis
Cmax 7594.82 nM Rattus norvegicus
Cmax 7600.0 nM Rattus norvegicus
F 25.0 % Rattus norvegicus
F 25.0 % Rattus norvegicus
F 93.0 % Canis lupus familiaris
F 76.0 % Macaca fascicularis
Fu 0.143 - Rattus norvegicus
Fu 0.196 - Canis lupus familiaris
Fu 0.248 - Macaca fascicularis
Fu 0.245 - Homo sapiens
Fu 0.719 - Homo sapiens
T1/2 4.3 hr Rattus norvegicus
T1/2 1.9 hr Rattus norvegicus
T1/2 5.7 hr Canis lupus familiaris
T1/2 6.5 hr Macaca fascicularis
Tmax 1.6 hr Rattus norvegicus
Tmax 1.0 hr 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 = 4.0 nM 8.4 Inhibition of human ADAMTS-5 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG p... 25415648
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 4.0 nM 8.4 Inhibition of human ADAMTS4 using 43-mer VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPS... 27194201
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 4.0 nM 8.4 Inhibition of human ADAMTS5 using 43-mer VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPS... 27194201
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 4.0 nM 8.4 Inhibition of human ADAMTS-4 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG p... 25415648
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 35.0 nM 7.46 Inhibition of human ADAMTS-5 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG p... 25415648
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 35.0 nM 7.46 Inhibition of human ADAMTS5 using 43-mer-VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPS... 27194201
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 10000.0 nM 5.0 Inhibition of human TACE using Mca-PQG1 peptide substrate assessed as substrate ... 25415648
Disintegrin and metalloproteinase domain-containing protein 17 IC50 = 10000.0 nM 5.0 Inhibition of human TACE using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
72 kDa type IV collagenase IC50 = 11000.0 nM 4.96 Inhibition of human MMP2 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
72 kDa type IV collagenase IC50 = 11000.0 nM 4.96 Inhibition of human MMP2 using Mca-PQG1 peptide substrate assessed as substrate ... 25415648
Collagenase 3 IC50 = 30000.0 nM 4.52 Inhibition of human MMP13 using Mca-PQG1 peptide substrate assessed as substrate... 25415648
Collagenase 3 IC50 = 30000.0 nM 4.52 Inhibition of human MMP13 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminopro... 27194201
Matrix metalloproteinase-9 IC50 = 65000.0 nM 4.19 Inhibition of human MMP9 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Stromelysin-1 IC50 = 69000.0 nM 4.16 Inhibition of human MMP3 using Mca-PQG1 peptide substrate assessed as substrate ... 25415648
Stromelysin-1 IC50 = 69000.0 nM 4.16 Inhibition of human MMP3 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Matrix metalloproteinase-14 IC50 = 86000.0 nM 4.07 Inhibition of human MMP14 using Mca-PQG1 peptide substrate assessed as substrate... 25415648
Matrix metalloproteinase-14 IC50 = 86000.0 nM 4.07 Inhibition of human MMP14 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminopro... 27194201
Interstitial collagenase IC50 = 100000.0 nM 4.0 Inhibition of human MMP1 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Matrilysin IC50 = 100000.0 nM 4.0 Inhibition of human MMP7 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201

Literature References

PubMed DOI Target Context # Activities
27194201 10.1021/acs.jmedchem.6b00398 ADMET 28
27194201 10.1021/acs.jmedchem.6b00398 Unchecked 27
25415648 10.1021/jm501522n Rattus norvegicus 8
27194201 10.1021/acs.jmedchem.6b00398 Rattus norvegicus 7
27194201 10.1021/acs.jmedchem.6b00398 No relevant target 5
25415648 10.1021/jm501522n A disintegrin and metalloproteinase with thrombospondin motifs 5 2
27194201 10.1021/acs.jmedchem.6b00398 A disintegrin and metalloproteinase with thrombospondin motifs 5 2
27194201 10.1021/acs.jmedchem.6b00398 A disintegrin and metalloproteinase with thrombospondin motifs 4 2
25415648 10.1021/jm501522n ADMET 2
25415648 10.1021/jm501522n Plasma 2
25415648 10.1021/jm501522n Cytochrome P450 2C9 1
25415648 10.1021/jm501522n Cytochrome P450 3A4 1
25415648 10.1021/jm501522n Disintegrin and metalloproteinase domain-containing protein 17 1
25415648 10.1021/jm501522n Matrix metalloproteinase-14 1
25415648 10.1021/jm501522n Collagenase 3 1
27194201 10.1021/acs.jmedchem.6b00398 ADAMTS5 1
25415648 10.1021/jm501522n Stromelysin-1 1
27194201 10.1021/acs.jmedchem.6b00398 Stromelysin-1 1
27194201 10.1021/acs.jmedchem.6b00398 Matrilysin 1
25415648 10.1021/jm501522n 72 kDa type IV collagenase 1

Data from ChEMBL 36 via Core Engine