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Compound Detail

CHEMBL4097165

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O=C1NC(=O)[C@](CNC(=O)c2cc3cc(C(F)(F)F)ccc3o2)(C2CC2)N1

Basic Information

ChEMBL ID CHEMBL4097165
Phase Preclinical
Structure Type MOL
InChI Key INOYENJSYPDBEC-INIZCTEOSA-N
10
Targets
11
Activities
1
Assay Types
14
PK Parameters
16
Publications
0
Known Names

Molecular Properties

381.3
MW (Da)
2.17
ALogP
4
HBA
3
HBD
100.4
PSA (Ų)
0.71
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 C17H14F3N3O4
MW 381.31
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -1.01

Activity Summary

IC50 11 meas. best 8.3

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
A disintegrin and metalloproteinase with thrombospondin motifs 5
CHEMBL2285
IC50 8.3 7.75 5.0 2
A disintegrin and metalloproteinase with thrombospondin motifs 4
CHEMBL2318
IC50 8.22 8.22 6.0 1
Macrophage metalloelastase
CHEMBL4393
IC50 8.05 8.05 9.0 1
72 kDa type IV collagenase
CHEMBL333
IC50 5.24 5.24 5800.0 1
Matrix metalloproteinase-14
CHEMBL3869
IC50 5.12 5.12 7600.0 1
Collagenase 3
CHEMBL280
IC50 4.8 4.8 16000.0 1
Stromelysin-1
CHEMBL283
IC50 4.77 4.77 17000.0 1
Matrix metalloproteinase-9
CHEMBL321
IC50 4.72 4.72 19000.0 1
Interstitial collagenase
CHEMBL332
IC50 4.3 4.3 50000.0 1
Matrilysin
CHEMBL4073
IC50 4.0 4.0 100000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.3 mL.min-1.kg-1 Canis lupus familiaris
CL 1.0 mL.min-1.kg-1 Macaca fascicularis
F 83.0 % Rattus norvegicus
F 74.0 % Canis lupus familiaris
F 100.0 % Macaca fascicularis
Fu 0.206 - Rattus norvegicus
Fu 0.215 - Canis lupus familiaris
Fu 0.229 - Macaca fascicularis
Fu 0.255 - Homo sapiens
Fu 0.557 - Homo sapiens
T1/2 3.8 hr Rattus norvegicus
T1/2 9.1 hr Canis lupus familiaris
T1/2 12.0 hr Macaca fascicularis

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 = 5.0 nM 8.3 Inhibition of human ADAMTS5 using 43-mer VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPS... 27194201
A disintegrin and metalloproteinase with thrombospondin motifs 4 IC50 = 6.0 nM 8.22 Inhibition of human ADAMTS4 using 43-mer VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPS... 27194201
Macrophage metalloelastase IC50 = 9.0 nM 8.05 Inhibition of human MMP12 using Mca-PQGL-(3-[2, 4-dinitrophenyl]-L-2, 3-diaminop... 28613895
A disintegrin and metalloproteinase with thrombospondin motifs 5 IC50 = 63.0 nM 7.2 Inhibition of human ADAMTS5 using 43-mer-VQTVTWPDMELPLPRNITEGEARGSVILTVKPIFEVSPS... 27194201
72 kDa type IV collagenase IC50 = 5800.0 nM 5.24 Inhibition of human MMP2 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Matrix metalloproteinase-14 IC50 = 7600.0 nM 5.12 Inhibition of human MMP14 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminopro... 27194201
Collagenase 3 IC50 = 16000.0 nM 4.8 Inhibition of human MMP13 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminopro... 27194201
Stromelysin-1 IC50 = 17000.0 nM 4.77 Inhibition of human MMP3 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Matrix metalloproteinase-9 IC50 = 19000.0 nM 4.72 Inhibition of human MMP9 using Mca-PQGL-(3-[2,4-dinitrophenyl]-L-2,3-diaminoprop... 27194201
Interstitial collagenase IC50 = 50000.0 nM 4.3 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 Unchecked 22
27194201 10.1021/acs.jmedchem.6b00398 ADMET 21
27194201 10.1021/acs.jmedchem.6b00398 Rattus norvegicus 7
27194201 10.1021/acs.jmedchem.6b00398 No relevant target 4
27194201 10.1021/acs.jmedchem.6b00398 A disintegrin and metalloproteinase with thrombospondin motifs 4 2
27194201 10.1021/acs.jmedchem.6b00398 A disintegrin and metalloproteinase with thrombospondin motifs 5 2
28613895 10.1021/acs.jmedchem.7b00650 Macrophage metalloelastase 1
27194201 10.1021/acs.jmedchem.6b00398 Interstitial collagenase 1
27194201 10.1021/acs.jmedchem.6b00398 72 kDa type IV collagenase 1
27194201 10.1021/acs.jmedchem.6b00398 Stromelysin-1 1
27194201 10.1021/acs.jmedchem.6b00398 Matrilysin 1
27194201 10.1021/acs.jmedchem.6b00398 Matrix metalloproteinase-9 1
27194201 10.1021/acs.jmedchem.6b00398 Collagenase 3 1
27194201 10.1021/acs.jmedchem.6b00398 Matrix metalloproteinase-14 1
27194201 10.1021/acs.jmedchem.6b00398 Disintegrin and metalloproteinase domain-containing protein 17 1
27194201 10.1021/acs.jmedchem.6b00398 ADAMTS5 1

Data from ChEMBL 36 via Core Engine