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Compound Detail

CHEMBL66654

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Cc1cccc(C#Cc2ccccc2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL66654
Phase Preclinical
Structure Type MOL
InChI Key NEWKHUASLBMWRE-UHFFFAOYSA-N
8
Targets
62
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

193.2
MW (Da)
2.79
ALogP
1
HBA
0
HBD
12.9
PSA (Ų)
0.59
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C14H11N
MW 193.25
Aromatic Rings 2
Heavy Atoms 15
NP-Likeness -1.19

Activity Summary

IC50 38 meas. best 9.7
Ki 23 meas. best 8.47
Kd 1 meas. best 8.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Metabotropic glutamate receptor 5
CHEMBL2564
 IC50 9.7 8.04 0.2 10
Metabotropic glutamate receptor 5
CHEMBL3227
 IC50 8.82 7.8915 1.5 20
Metabotropic glutamate receptor 5
CHEMBL3227
 Ki 8.47 7.92 3.4 8
Metabotropic glutamate receptor 5
CHEMBL2564
 Ki 8.33 7.9308 4.7 12
Metabotropic glutamate receptor 5
CHEMBL3227
 Kd 8.07 8.07 8.6 1
Metabotropic glutamate receptor 1
CHEMBL3772
 Ki 7.44 5.98 36.0 2
Histone deacetylase 6
CHEMBL1865
 IC50 6.32 6.32 475.8 1
Cytochrome P450 1A2
CHEMBL3356
 Ki 6.3 6.3 500.0 1
Luciferin 4-monooxygenase
CHEMBL5567
 IC50 5.33 5.04 4700.0 4
Amine oxidase [flavin-containing] A
CHEMBL3681
 IC50 5.1 5.1 8000.0 1
Glutamate receptor ionotropic, NMDA 2B
CHEMBL1904
 IC50 4.75 4.75 18000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Metabotropic glutamate receptor 5 IC50 = 0.2 nM 9.7 Activity at rat mGlu5 receptor expressed in CHO cells assessed as inhibition of ... 17590335
Metabotropic glutamate receptor 5 IC50 = 1.5 nM 8.82 Antagonist activity at human mGluR5 receptor expressed in CHOK1 cells assessed a... 17569516
Metabotropic glutamate receptor 5 IC50 = 2.0 nM 8.7 Tested in vitro against human recombinant Metabotropic glutamate receptor 5 stab... 12519057
Metabotropic glutamate receptor 5 IC50 = 2.0 nM 8.7 In vitro functional potency using an automated assay employing LtK-cells stably ... 12565928
Metabotropic glutamate receptor 5 IC50 = 2.3 nM 8.64 Antagonist activity at human mGluR5 expressed in HEK293 cells assessed as inhibi... 23357634
Metabotropic glutamate receptor 5 IC50 = 2.93 nM 8.53 Antagonist activity at rat mGluR5 expressed in human HEK-293 cells assessed as i... 21546249
Metabotropic glutamate receptor 5 Ki = 3.4 nM 8.47 Displacement of [3H]-ABP688 from human mGluR5 expressed in HEK293 cells after 60... 23357634
Metabotropic glutamate receptor 5 Ki = 3.5 nM 8.46 Displacement of [3H]-M-MPEP from mGluR5 StaR domain (569 to 836 residues) (unkno... 26706173
Metabotropic glutamate receptor 5 IC50 = 3.54 nM 8.45 Antagonist activity at rat mGluR5 expressed in HEK293T cells assessed as inhibit... 21295978
Metabotropic glutamate receptor 5 IC50 = 3.54 nM 8.45 Antagonist activity at rat mGluR5 expressed in HEK293A cells assessed as glutama... 19445453
Metabotropic glutamate receptor 5 IC50 = 4.0 nM 8.4 Displacement of [3H]MPEP from mGlu5 receptor 17196387
Metabotropic glutamate receptor 5 Ki = 4.7 nM 8.33 Displacement of [3H]3methoxy-5-(pyridin-2-ylethynyl)pyridine from rat mGluR5 19854049
Metabotropic glutamate receptor 5 Ki = 4.7 nM 8.33 Displacement of [3H]3methoxy-5-(pyridin-2-ylethynyl)pyridine from rat mGluR5 19854049
Metabotropic glutamate receptor 5 Ki = 5.7 nM 8.24 Displacement of [3H]MPEP from mGlu5 receptor in rat brain 17590335
Metabotropic glutamate receptor 5 Kd = 8.6 nM 8.07 Binding affinity to human mGluR5 expressed in HEK293 cell membranes expressing G... 23046966
Metabotropic glutamate receptor 5 Ki = 9.6 nM 8.02 Displacement of [3H]M-MPEP from mGluR5 in Sprague-Dawley rat cerebrocortical mem... 28212015
Metabotropic glutamate receptor 5 IC50 = 10.0 nM 8.0 Antagonist activity at human mGluR5 expressed in CHO cells assessed as increase ... 18304814
Metabotropic glutamate receptor 5 Ki = 10.4 nM 7.98 Displacement of [3H]MPEP from human cloned mGluR5 receptor expressed in CHO-T-Re... 26014480
Metabotropic glutamate receptor 5 Ki = 10.4 nM 7.98 Displacement of [3H]MPEP from human mGlu5 receptor expressed in CHO-TREx cell me... 30624919
Metabotropic glutamate receptor 5 IC50 = 11.0 nM 7.96 Binding affinity towards human mGlu5 receptors expressed in LtK-cells 12565928

Literature References

PubMed DOI Target Context # Activities
22924094 10.1021/ml3000726 Mus musculus 12
18363348 10.1021/jm701302v Luciferin 4-monooxygenase 5
- 10.6019/CHEMBL4808148 Histone deacetylase 6 4
18327252 10.1038/nchembio.78 Drosophila 4
26014480 10.1016/j.bmc.2015.05.008 Metabotropic glutamate receptor 5 3
12519057 10.1021/jm025570j Rattus norvegicus 3
19445453 10.1021/jm900172f Metabotropic glutamate receptor 5 3
12519057 10.1021/jm025570j Metabotropic glutamate receptor 5 3
23046966 10.1016/j.bmcl.2012.08.100 Metabotropic glutamate receptor 5 3
12565928 10.1016/s0960-894x(02)00997-6 Metabotropic glutamate receptor 5 3
22924094 10.1021/ml3000726 Metabotropic glutamate receptor 5 3
11814808 10.1016/s0960-894x(01)00767-3 Metabotropic glutamate receptor 5 2
17196387 10.1016/j.bmcl.2006.12.033 Metabotropic glutamate receptor 5 2
21546249 10.1016/j.bmcl.2011.04.047 Metabotropic glutamate receptor 5 2
23357634 10.1016/j.bmcl.2012.12.078 Metabotropic glutamate receptor 5 2
18363348 10.1021/jm701302v Unchecked 2
20615697 10.1016/j.bmcl.2010.06.075 Metabotropic glutamate receptor 1 2
19854049 10.1016/j.bmcl.2009.10.024 Metabotropic glutamate receptor 5 2
21295978 10.1016/j.bmcl.2010.12.110 Metabotropic glutamate receptor 5 2
17110115 10.1016/j.bmc.2006.10.038 Metabotropic glutamate receptor 5 2

Data from ChEMBL 36 via Core Engine