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Compound Detail

CHEMBL2386849

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Cc1cc(Oc2cncc(F)c2)cc(C(=O)Nc2ccc(F)cn2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2386849
Phase Preclinical
Structure Type MOL
InChI Key MBSANIMQXDBICP-UHFFFAOYSA-N
5
Targets
11
Activities
1
Assay Types
21
PK Parameters
20
Publications
0
Known Names

Molecular Properties

342.3
MW (Da)
3.50
ALogP
5
HBA
1
HBD
77.0
PSA (Ų)
0.79
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 C17H12F2N4O2
MW 342.31
Aromatic Rings 3
Heavy Atoms 25
NP-Likeness -1.65

Activity Summary

IC50 11 meas. best 8.51

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Metabotropic glutamate receptor 5
CHEMBL2564
 IC50 8.51 8.4967 3.1 3
Cytochrome P450 1A2
CHEMBL3356
 IC50 6.7 6.7 200.0 2
Sodium-dependent dopamine transporter
CHEMBL238
 IC50 5.86 5.835 1380.0 2
Cytochrome P450 3A4
CHEMBL340
 IC50 5.37 5.37 4300.0 2
Cytochrome P450 2C9
CHEMBL3397
 IC50 5.27 5.27 5400.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 13007.78 ng.hr.mL-1 Rattus norvegicus
AUC 2201.05 ng.hr.mL-1 Macaca fascicularis
CL 9.2 mL.min-1.kg-1 Rattus norvegicus
CL 13.3 mL.min-1.kg-1 Macaca fascicularis
Cmax 3330.0 nM Rattus norvegicus
Cmax 1360.0 nM Macaca fascicularis
F 25.0 % Macaca fascicularis
F 67.0 % Rattus norvegicus
F 71.0 % Rattus norvegicus
F 35.0 % Macaca fascicularis
Fu 0.015 - Rattus norvegicus
Fu 0.011 - Homo sapiens
Fu 0.011 - Mus musculus
Fu 0.015 - Rattus norvegicus
Fu 0.011 - Homo sapiens
MRT 3.467 hr Rattus norvegicus
MRT 5.05 hr Macaca fascicularis
T1/2 4.683 hr Rattus norvegicus
T1/2 9.383 hr Macaca fascicularis
Tmax 1.5 hr Rattus norvegicus
Tmax 2.0 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Metabotropic glutamate receptor 5 IC50 = 3.1 nM 8.51 Negative allosteric modulation of rat mGlu5 receptor expressed in HEK293A cells ... 28530802
Metabotropic glutamate receptor 5 IC50 = 3.09 nM 8.51 Negative allosteric modulation of rat mGlu5 receptor expressed in HEK293A cells ... 28530802
Metabotropic glutamate receptor 5 IC50 = 3.4 nM 8.47 Negative allosteric modulation of rat mGluR5 receptor expressed in HEK293A cells... 24900698
Cytochrome P450 1A2 IC50 = 200.0 nM 6.7 Inhibition of CYP1A2 in human liver microsomes using tacrine as substrate preinc... 28530802
Cytochrome P450 1A2 IC50 = 200.0 nM 6.7 Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate pre... 28958625
Sodium-dependent dopamine transporter IC50 = 1380.0 nM 5.86 Inhibition of human recombinant DAT expressed in CHO-S cells assessed as reducti... 28530802
Sodium-dependent dopamine transporter IC50 = 1540.0 nM 5.81 Displacement of [125I] RTI-55 from human recombinant DAT expressed in CHO-S cell... 28530802
Cytochrome P450 3A4 IC50 = 4300.0 nM 5.37 Inhibition of CYP3A4 in human liver microsomes using midazolam as substrate prei... 28530802
Cytochrome P450 3A4 IC50 = 4300.0 nM 5.37 Inhibition of CYP3A4 in human liver microsomes using midazolam as substrate pret... 28958625
Cytochrome P450 2C9 IC50 = 5400.0 nM 5.27 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate pre... 28530802
Cytochrome P450 2C9 IC50 = 5400.0 nM 5.27 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate pre... 28958625

Literature References

PubMed DOI Target Context # Activities
28530802 10.1021/acs.jmedchem.7b00410 Cynomolgus monkey 8
28530802 10.1021/acs.jmedchem.7b00410 Rattus norvegicus 8
28530802 10.1021/acs.jmedchem.7b00410 Plasma 4
28530802 10.1021/acs.jmedchem.7b00410 Sodium-dependent dopamine transporter 3
28530802 10.1021/acs.jmedchem.7b00410 Metabotropic glutamate receptor 5 3
28530802 10.1021/acs.jmedchem.7b00410 Brain 3
28958625 10.1016/j.bmcl.2017.09.042 Plasma 2
28530802 10.1021/acs.jmedchem.7b00410 Unchecked 2
28530802 10.1021/acs.jmedchem.7b00410 ADMET 2
28530802 10.1021/acs.jmedchem.7b00410 Cytochrome P450 2C9 1
28530802 10.1021/acs.jmedchem.7b00410 Metabotropic glutamate receptor 3 1
28530802 10.1021/acs.jmedchem.7b00410 Metabotropic glutamate receptor 2 1
28958625 10.1016/j.bmcl.2017.09.042 Sodium-dependent dopamine transporter 1
24900698 10.1021/ml400138p Mus musculus 1
28530802 10.1021/acs.jmedchem.7b00410 Cytochrome P450 2D6 1
28530802 10.1021/acs.jmedchem.7b00410 Cytochrome P450 3A4 1
24900698 10.1021/ml400138p Metabotropic glutamate receptor 5 1
24900698 10.1021/ml400138p Plasma 1
24900698 10.1021/ml400138p Nucleic Acid 1
24900698 10.1021/ml400138p Rattus norvegicus 1

Data from ChEMBL 36 via Core Engine