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Compound Detail

CHEMBL2386850

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Cc1cc(Oc2cncnc2)cc(C(=O)Nc2ccc(F)cn2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL2386850
Phase Preclinical
Structure Type MOL
InChI Key RBAHIIPVJVMACF-UHFFFAOYSA-N
5
Targets
16
Activities
2
Assay Types
22
PK Parameters
20
Publications
0
Known Names

Molecular Properties

325.3
MW (Da)
2.76
ALogP
6
HBA
1
HBD
89.9
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 C16H12FN5O2
MW 325.30
Aromatic Rings 3
Heavy Atoms 24
NP-Likeness -1.62

Activity Summary

IC50 14 meas. best 8.11
Ki 2 meas. best 8.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Metabotropic glutamate receptor 5
CHEMBL2564
 Ki 8.36 7.49 4.4 2
Metabotropic glutamate receptor 5
CHEMBL2564
 IC50 8.11 8.0 7.8 4
Metabotropic glutamate receptor 5
CHEMBL3227
 IC50 7.85 7.85 14.0 1
Cytochrome P450 1A2
CHEMBL3356
 IC50 6.0 5.8467 1000.0 3
Cytochrome P450 2C9
CHEMBL3397
 IC50 4.92 4.7867 12100.0 3
Voltage-gated inwardly rectifying potassium channel KCNH2
CHEMBL240
 IC50 4.13 4.13 73600.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 4749.38 ng.hr.mL-1 Rattus norvegicus
AUC 2381.2 ng.hr.mL-1 Macaca fascicularis
CL 19.3 mL.min-1.kg-1 Rattus norvegicus
CL 15.5 mL.min-1.kg-1 Macaca fascicularis
Cmax 4340.0 nM Rattus norvegicus
Cmax 1720.0 nM Macaca fascicularis
F 30.0 % Rattus norvegicus
F 42.0 % Macaca fascicularis
F 53.0 % Rattus norvegicus
F 44.0 % Macaca fascicularis
Fu 0.106 - Rattus norvegicus
Fu 0.12 - Homo sapiens
Fu 0.078 - Mus musculus
Fu 0.106 - Rattus norvegicus
Fu 0.12 - Homo sapiens
MRT 1.55 hr Rattus norvegicus
MRT 2.717 hr Macaca fascicularis
T1/2 6.5 hr Rattus norvegicus
T1/2 5.033 hr Macaca fascicularis
T1/2 5.367 hr Homo sapiens
Tmax 0.5 hr Rattus norvegicus
Tmax 3.0 hr Macaca fascicularis

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Metabotropic glutamate receptor 5 Ki = 4.4 nM 8.36 Displacement of [3H]-3-methoxy-5-(pyridin-2-ylethynyl)pyridine from rat mGlu5 re... 28530802
Metabotropic glutamate receptor 5 IC50 = 7.8 nM 8.11 Negative allosteric modulation of rat mGluR5 receptor expressed in HEK293A cells... 24900698
Metabotropic glutamate receptor 5 IC50 = 10.72 nM 7.97 Negative allosteric modulation of rat mGlu5 receptor expressed in HEK293A cells ... 28530802
Metabotropic glutamate receptor 5 IC50 = 11.0 nM 7.96 Negative allosteric modulation of rat mGlu5 receptor expressed in HEK293A cells ... 28530802
Metabotropic glutamate receptor 5 IC50 = 11.0 nM 7.96 Negative allosteric modulator activity at rat mGlu5 receptor expressed in HEK293... 29705142
Metabotropic glutamate receptor 5 IC50 = 14.0 nM 7.85 Negative allosteric modulation of human mGlu5 receptor expressed in HEK293 cells... 28530802
Metabotropic glutamate receptor 5 Ki = 240.0 nM 6.62 Negative allosteric modulation of rat mGlu5 receptor expressed in HEK293A cells ... 28530802
Cytochrome P450 1A2 IC50 = 1000.0 nM 6.0 Inhibition of CYP1A2 in human liver microsomes using tacrine as substrate preinc... 28530802
Cytochrome P450 1A2 IC50 = 1000.0 nM 6.0 Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate in ... 29705142
Cytochrome P450 1A2 IC50 = 2900.0 nM 5.54 Inhibition of CYP1A2 in human liver microsomes using phenacetin as substrate pre... 28530802
Cytochrome P450 2C9 IC50 = 12100.0 nM 4.92 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate pre... 28530802
Cytochrome P450 2C9 IC50 = 12100.0 nM 4.92 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate in ... 29705142
Cytochrome P450 2C9 IC50 = 29900.0 nM 4.52 Inhibition of CYP2C9 in human liver microsomes using diclofenac as substrate pre... 28530802
Voltage-gated inwardly rectifying potassium channel KCNH2 IC50 = 73600.0 nM 4.13 Inhibition of human ERG expressed in CHO cells by automated patch clamp assay 28530802

Literature References

PubMed DOI Target Context # Activities
28530802 10.1021/acs.jmedchem.7b00410 Rattus norvegicus 13
28530802 10.1021/acs.jmedchem.7b00410 ADMET 10
28530802 10.1021/acs.jmedchem.7b00410 Unchecked 10
28530802 10.1021/acs.jmedchem.7b00410 Metabotropic glutamate receptor 5 9
28530802 10.1021/acs.jmedchem.7b00410 Cynomolgus monkey 8
29705142 10.1016/j.bmcl.2018.04.053 Unchecked 7
28530802 10.1021/acs.jmedchem.7b00410 Brain 5
28530802 10.1021/acs.jmedchem.7b00410 Salmonella typhimurium 4
28530802 10.1021/acs.jmedchem.7b00410 Papio anubis 4
28530802 10.1021/acs.jmedchem.7b00410 Plasma 4
28530802 10.1021/acs.jmedchem.7b00410 Cytochrome P450 3A4 4
28530802 10.1021/acs.jmedchem.7b00410 Cytochrome P450 2D6 3
28530802 10.1021/acs.jmedchem.7b00410 Cytochrome P450 2C9 3
28530802 10.1021/acs.jmedchem.7b00410 Cytochrome P450 1A2 3
28530802 10.1021/acs.jmedchem.7b00410 Sodium channel protein type 5 subunit alpha 2
29705142 10.1016/j.bmcl.2018.04.053 ADMET 2
24900698 10.1021/ml400138p Cynomolgus monkey 1
28530802 10.1021/acs.jmedchem.7b00410 Metabotropic glutamate receptor 2 1
29705142 10.1016/j.bmcl.2018.04.053 Cytochrome P450 1A2 1
24900698 10.1021/ml400138p Metabotropic glutamate receptor 5 1

Data from ChEMBL 36 via Core Engine