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Compound Detail

CHEMBL3597594

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Cc1cccc(C#CC=C2CCN(c3ncccc3[N+](=O)[O-])CC2)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3597594
Phase Preclinical
Structure Type MOL
InChI Key WYDQDVYUIYFOCH-UHFFFAOYSA-N
4
Targets
9
Activities
2
Assay Types
0
PK Parameters
9
Publications
0
Known Names

Molecular Properties

334.4
MW (Da)
3.27
ALogP
5
HBA
0
HBD
72.2
PSA (Ų)
0.48
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C19H18N4O2
MW 334.38
Aromatic Rings 2
Heavy Atoms 25
NP-Likeness -1.15

Activity Summary

Ki 5 meas. best 10.52
IC50 4 meas. best 9.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Metabotropic glutamate receptor 5
CHEMBL2564
 Ki 10.52 10.52 0.0 1
Metabotropic glutamate receptor 5
CHEMBL3227
 Ki 9.3 9.3 0.5 2
Metabotropic glutamate receptor 5
CHEMBL3227
 IC50 9.1 9.1 0.8 2
Metabotropic glutamate receptor 1
CHEMBL4477
 Ki 6.74 6.74 184.2 2
Metabotropic glutamate receptor 1
CHEMBL4477
 IC50 6.35 6.35 447.5 1
Cytochrome P450 3A4
CHEMBL340
 IC50 5.35 5.35 4500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Metabotropic glutamate receptor 5 Ki = 0.03 nM 10.52 Displacement of [3H]MPEP from mGluR5 receptor in Sprague-Dawley rat forebrain me... 26014480
Metabotropic glutamate receptor 5 Ki = 0.5 nM 9.3 Displacement of [3H]MPEP from human cloned mGluR5 receptor expressed in CHO-T-Re... 26014480
Metabotropic glutamate receptor 5 Ki = 0.5 nM 9.3 Displacement of [3H]MPEP from human mGlu5 receptor expressed in CHO-TREx cell me... 30624919
Metabotropic glutamate receptor 5 IC50 = 0.8 nM 9.1 Negative allosteric modulatory activity at human cloned mGluR5 receptor expresse... 26014480
Metabotropic glutamate receptor 5 IC50 = 0.8 nM 9.1 Negative allosteric modulation of human mGlu5 receptor expressed in CHO-TREx cel... 30624919
Metabotropic glutamate receptor 1 Ki = 184.2 nM 6.74 Displacement of [3H]R214127 from rat cloned mGluR1 receptor expressed in CHO-T-R... 26014480
Metabotropic glutamate receptor 1 Ki = 184.2 nM 6.74 Displacement of [3H]MPEP from rat mGlu1 receptor expressed in CHO-TREx cell memb... 30624919
Metabotropic glutamate receptor 1 IC50 = 447.5 nM 6.35 Negative allosteric modulatory activity at rat cloned mGluR1 receptor expressed ... 26014480
Cytochrome P450 3A4 IC50 = 4500.0 nM 5.35 Inhibition of recombinant human CYP3A4 using 7-benzyloxy-trifluoromethylcoumarin... 30624919

Literature References

PubMed DOI Target Context # Activities
26014480 10.1016/j.bmc.2015.05.008 Metabotropic glutamate receptor 5 4
26014480 10.1016/j.bmc.2015.05.008 Metabotropic glutamate receptor 1 2
30624919 10.1021/acs.jmedchem.8b01226 ADMET 2
30624919 10.1021/acs.jmedchem.8b01226 Metabotropic glutamate receptor 5 2
30624919 10.1021/acs.jmedchem.8b01226 Cytochrome P450 3A4 1
30624919 10.1021/acs.jmedchem.8b01226 Cytochrome P450 2D6 1
30624919 10.1021/acs.jmedchem.8b01226 Cytochrome P450 1A2 1
30624919 10.1021/acs.jmedchem.8b01226 No relevant target 1
30624919 10.1021/acs.jmedchem.8b01226 Metabotropic glutamate receptor 1 1

Data from ChEMBL 36 via Core Engine