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Compound Detail

CHEMBL40143

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CC1(C)NC(=O)N(C[C@@H](COc2ccc(-c3ccc(OC(F)(F)F)cc3)cc2)N(O)C=O)C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL40143
Phase Preclinical
Structure Type MOL
InChI Key IIHFBHZWJNGWRC-INIZCTEOSA-N
4
Targets
12
Activities
1
Assay Types
24
PK Parameters
20
Publications
0
Known Names

Molecular Properties

481.4
MW (Da)
3.18
ALogP
6
HBA
2
HBD
108.4
PSA (Ų)
0.25
QED
0
Ro5 Violations
9
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C22H22F3N3O6
MW 481.43
Aromatic Rings 2
Heavy Atoms 34
NP-Likeness -0.77

Activity Summary

IC50 12 meas. best 8.4

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
72 kDa type IV collagenase
CHEMBL333
 IC50 8.4 8.4 4.0 3
Stromelysin-1
CHEMBL283
 IC50 7.38 7.38 42.0 3
Matrix metalloproteinase-9
CHEMBL321
 IC50 6.92 6.92 120.0 3
Interstitial collagenase
CHEMBL332
 IC50 5.34 5.34 4600.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 24000.0 ng.hr.mL-1 Rattus norvegicus
AUC 23000.0 ng.hr.mL-1 Canis lupus familiaris
AUC 43000.0 ng.hr.mL-1 Cercopithecidae
CL 2.0 mL.min-1.kg-1 Rattus norvegicus
CL 1.833 mL.min-1.kg-1 Canis lupus familiaris
CL 1.133 mL.min-1.kg-1 Macaca fascicularis
Clp 0.12 kg-1 hr-1 Rattus norvegicus
Clp 0.11 kg-1 hr-1 Canis lupus familiaris
Clp 0.068 kg-1 hr-1 Cercopithecidae
F 93.0 % Rattus norvegicus
F 83.0 % Canis lupus familiaris
F 95.0 % Cercopithecidae
F 83.95 % Rattus norvegicus
F 83.95 % Canis lupus familiaris
F 83.95 % Macaca fascicularis
T1/2 8.0 hr Cercopithecidae
T1/2 9.0 hr Canis lupus familiaris
T1/2 21.0 hr Cercopithecidae
T1/2 8.0 hr Rattus norvegicus
T1/2 9.0 hr Canis lupus familiaris
T1/2 21.0 hr Macaca fascicularis
Vd 1.2 L.kg-1 Rattus norvegicus
Vd 0.9 L.kg-1 Canis lupus familiaris
Vd 1.2 L.kg-1 Cercopithecidae

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
72 kDa type IV collagenase IC50 = 4.0 nM 8.4 In vitro inhibition of human Matrix metalloprotease-2. 11412980
72 kDa type IV collagenase IC50 = 4.0 nM 8.4 Inhibition of MMP2 18790648
72 kDa type IV collagenase IC50 = 4.0 nM 8.4 Inhibition of MMP-2 (unknown origin) 35969157
Stromelysin-1 IC50 = 42.0 nM 7.38 Inhibition of Matrix metalloprotease-3 11412980
Stromelysin-1 IC50 = 42.0 nM 7.38 Inhibition of MMP3 18790648
Stromelysin-1 IC50 = 42.0 nM 7.38 Inhibition of MMP-3 (unknown origin) 35969157
Matrix metalloproteinase-9 IC50 = 120.0 nM 6.92 Inhibition of matrix metalloprotease-9 11412980
Matrix metalloproteinase-9 IC50 = 120.0 nM 6.92 Inhibition of MMP9 18790648
Matrix metalloproteinase-9 IC50 = 120.0 nM 6.92 Inhibition of MMP-9 (unknown origin) 35969157
Interstitial collagenase IC50 = 4600.0 nM 5.34 In vitro inhibition of human Matrix metalloprotease-1. 11412980
Interstitial collagenase IC50 = 4600.0 nM 5.34 Inhibition of MMP1 18790648
Interstitial collagenase IC50 = 4600.0 nM 5.34 Inhibition of MMP-1 (unknown origin) 35969157

Literature References

PubMed DOI Target Context # Activities
35969157 10.1021/acs.jmedchem.1c01855 ADMET 12
11412980 10.1016/s0960-894x(01)00032-4 ADMET 6
11412980 10.1016/s0960-894x(01)00032-4 Canis familiaris 5
11412980 10.1016/s0960-894x(01)00032-4 Rattus norvegicus 4
18790648 10.1016/j.bmc.2008.08.058 Matrix metalloproteinase-9 1
35969157 10.1021/acs.jmedchem.1c01855 B16-F10 1
35969157 10.1021/acs.jmedchem.1c01855 72 kDa type IV collagenase 1
35969157 10.1021/acs.jmedchem.1c01855 Interstitial collagenase 1
20020916 10.1080/15376510701857262 Phospholipidosis 1
20799726 10.1021/mp100103e Phospholipidosis 1
18790648 10.1016/j.bmc.2008.08.058 Interstitial collagenase 1
18790648 10.1016/j.bmc.2008.08.058 72 kDa type IV collagenase 1
18790648 10.1016/j.bmc.2008.08.058 Stromelysin-1 1
18790648 10.1016/j.bmc.2008.08.058 Matrilysin 1
11412980 10.1016/s0960-894x(01)00032-4 Interstitial collagenase 1
11412980 10.1016/s0960-894x(01)00032-4 Mus musculus 1
11412980 10.1016/s0960-894x(01)00032-4 B16 1
11412980 10.1016/s0960-894x(01)00032-4 Matrix metalloproteinase-9 1
11412980 10.1016/s0960-894x(01)00032-4 Matrilysin 1
11412980 10.1016/s0960-894x(01)00032-4 Stromelysin-1 1

Data from ChEMBL 36 via Core Engine