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Compound Detail

CHEMBL3358156

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

Basic Information

ChEMBL ID CHEMBL3358156
Phase Preclinical
Structure Type MOL
InChI Key NPWGFJCNOCYDSO-KRWDZBQOSA-N
10
Targets
17
Activities
1
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

387.8
MW (Da)
1.28
ALogP
6
HBA
3
HBD
118.3
PSA (Ų)
0.58
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 C17H14ClN5O4
MW 387.78
Aromatic Rings 3
Heavy Atoms 27
NP-Likeness -1.22

Activity Summary

IC50 17 meas. best 8.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A disintegrin and metalloproteinase with thrombospondin motifs 5
CHEMBL2285
 IC50 8.52 7.6575 3.0 4
A disintegrin and metalloproteinase with thrombospondin motifs 4
CHEMBL2318
 IC50 8.52 8.41 3.0 2
Collagenase 3
CHEMBL280
 IC50 5.6 5.49 2500.0 2
72 kDa type IV collagenase
CHEMBL333
 IC50 5.5 5.31 3200.0 2
Disintegrin and metalloproteinase domain-containing protein 17
CHEMBL3706
 IC50 5.0 5.0 10000.0 1
Matrix metalloproteinase-9
CHEMBL321
 IC50 4.77 4.77 17000.0 1
Interstitial collagenase
CHEMBL332
 IC50 4.72 4.72 19000.0 1
Stromelysin-1
CHEMBL283
 IC50 4.64 4.53 23000.0 2
Matrix metalloproteinase-14
CHEMBL3869
 IC50 4.43 4.43 37000.0 1
Matrilysin
CHEMBL4073
 IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 8100.0 ng.hr.mL-1 Rattus norvegicus
AUC 8143.38 ng.hr.mL-1 Rattus norvegicus
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 10573.01 nM Rattus norvegicus
Cmax 11000.0 nM Rattus norvegicus
F 58.0 % Rattus norvegicus
T1/2 4.2 hr Rattus norvegicus
Tmax 0.33 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 = 3.0 nM 8.52 Inhibition of human ADAMTS5 using 43-mer VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPS... 27194201
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 3.0 nM 8.52 Inhibition of human ADAMTS4 using 43-mer VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPS... 27194201
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 5.0 nM 8.3 Inhibition of human ADAMTS-4 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG p... 25415648
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 9.0 nM 8.05 Inhibition of human ADAMTS-5 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG p... 25415648
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 79.0 nM 7.1 Inhibition of human ADAMTS5 using 43-mer-VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPS... 27194201
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 110.0 nM 6.96 Inhibition of human ADAMTS-5 using VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPSPLKG p... 25415648
Collagenase 3 IC50 = 2500.0 nM 5.6 Inhibition of human MMP13 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminopro... 27194201
72 kDa type IV collagenase IC50 = 3200.0 nM 5.5 Inhibition of human MMP2 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Collagenase 3 IC50 = 4200.0 nM 5.38 Inhibition of human MMP13 using Mca-PQG1 peptide substrate assessed as substrate... 25415648
72 kDa type IV collagenase IC50 = 7500.0 nM 5.12 Inhibition of human MMP2 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
Matrix metalloproteinase-9 IC50 = 17000.0 nM 4.77 Inhibition of human MMP9 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Interstitial collagenase IC50 = 19000.0 nM 4.72 Inhibition of human MMP1 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Stromelysin-1 IC50 = 23000.0 nM 4.64 Inhibition of human MMP3 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Matrix metalloproteinase-14 IC50 = 37000.0 nM 4.43 Inhibition of human MMP14 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminopro... 27194201
Stromelysin-1 IC50 = 38000.0 nM 4.42 Inhibition of human MMP3 using Mca-PQG1 peptide substrate assessed as substrate ... 25415648
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 Unchecked 18
25415648 10.1021/jm501522n Rattus norvegicus 7
27194201 10.1021/acs.jmedchem.6b00398 ADMET 3
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 Disintegrin and metalloproteinase domain-containing protein 17 1
25415648 10.1021/jm501522n Cytochrome P450 2D6 1
25415648 10.1021/jm501522n Cytochrome P450 2C9 1
25415648 10.1021/jm501522n Cytochrome P450 3A4 1
25415648 10.1021/jm501522n Matrix metalloproteinase-14 1
25415648 10.1021/jm501522n Collagenase 3 1
25415648 10.1021/jm501522n Stromelysin-1 1
27194201 10.1021/acs.jmedchem.6b00398 Interstitial collagenase 1
27194201 10.1021/acs.jmedchem.6b00398 ADAMTS5 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