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Compound Detail

CHEMBL13378

(R,S)-AMPA
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Cc1onc(O)c1CC(N)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL13378
Name (R,S)-AMPA
Phase Preclinical
Structure Type MOL
InChI Key UUDAMDVQRQNNHZ-UHFFFAOYSA-N
20
Targets
57
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

186.2
MW (Da)
-0.36
ALogP
5
HBA
3
HBD
109.6
PSA (Ų)
0.59
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C7H10N2O4
MW 186.17
Aromatic Rings 1
Heavy Atoms 13
NP-Likeness 0.09

Activity Summary

IC50 20 meas. best 7.92
EC50 19 meas. best 5.85
Ki 18 meas. best 10.77

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glutamate receptor 2
CHEMBL3503
 Ki 10.77 9.275 0.0 2
Glutamate receptor 3
CHEMBL3504
 Ki 10.68 9.185 0.0 2
Glutamate receptor 1
CHEMBL3753
 Ki 10.66 9.16 0.0 2
Glutamate receptor 4
CHEMBL3505
 Ki 10.4 10.4 0.0 1
Glutamate receptor ionotropic, kainate 1
CHEMBL2919
 Ki 8.92 7.43 1.2 2
Glutamate receptor ionotropic, kainate
CHEMBL2094119
 IC50 7.92 6.11 12.0 2
Glutamate receptor 2
CHEMBL4016
 Ki 7.77 7.77 17.0 1
Glutamate receptor ionotropic AMPA
CHEMBL2096670
 IC50 7.72 7.3 19.0 4
Unchecked
CHEMBL612545
 Ki 7.72 7.72 19.0 1
Glutamate receptor 3
CHEMBL3595
 Ki 7.68 7.68 21.0 1
Glutamate receptor 1
CHEMBL2009
 Ki 7.66 7.66 22.0 1
Unchecked
CHEMBL612545
 IC50 7.62 7.48 24.0 3
Glutamate receptor 1
CHEMBL3753
 IC50 7.4 7.4 40.0 1
Glutamate receptor 4
CHEMBL3190
 Ki 7.4 7.4 40.0 1
Glutamate receptor ionotropic, AMPA
CHEMBL2096617
 IC50 7.4 7.4 40.0 1
Glutamate receptor ionotropic, AMPA
CHEMBL2093871
 IC50 7.4 7.1457 40.0 7
Rattus norvegicus
CHEMBL376
 Ki 6.56 6.56 275.4 1
Glutamate receptor ionotropic, kainate 1
CHEMBL1918
 Ki 6.13 6.13 740.0 1
Rattus norvegicus
CHEMBL376
 IC50 6.1 6.1 800.0 1
Glutamate receptor 3
CHEMBL3504
 EC50 5.85 5.3767 1400.0 3
Glutamate receptor AMPA 1/2
CHEMBL3883294
 EC50 5.48 5.48 3310.0 1
Rattus norvegicus
CHEMBL376
 EC50 5.46 5.4283 3500.0 6
Glutamate receptor ionotropic, AMPA
CHEMBL2093871
 EC50 5.46 5.46 3500.0 1
Unchecked
CHEMBL612545
 EC50 5.46 5.38 3500.0 2
Glutamate receptor 1
CHEMBL3753
 EC50 5.06 4.67 8700.0 2
Glutamate receptor 1
CHEMBL3502
 EC50 5.06 5.06 8700.0 1
ADMET
CHEMBL612558
 EC50 4.89 4.89 13000.0 1
Glutamate receptor 4
CHEMBL3505
 EC50 4.8 4.8 16000.0 1
Glutamate receptor 2
CHEMBL3503
 EC50 4.17 4.17 67000.0 1
Glutamate receptor ionotropic kainate
CHEMBL2109241
 IC50 4.17 4.17 68000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glutamate receptor 2 Ki = 0.017 nM 10.77 Displacement of [3H]AMPA from rat recombinant GluR2 expressed in Sf9 cells 17455929
Glutamate receptor 3 Ki = 0.021 nM 10.68 Displacement of [3H]AMPA from rat recombinant GluR3 expressed in Sf9 cells 17455929
Glutamate receptor 1 Ki = 0.022 nM 10.66 Displacement of [3H]AMPA from rat recombinant GluR1 expressed in Sf9 cells 17455929
Glutamate receptor 4 Ki = 0.04 nM 10.4 Displacement of [3H]AMPA from rat recombinant GluR4 expressed in Sf9 cells 17455929
Glutamate receptor ionotropic, kainate 1 Ki = 1.2 nM 8.92 Displacement of [3H]SYM 2081 from rat recombinant GluR5 expressed in Sf9 cells 17455929
Glutamate receptor ionotropic, kainate IC50 = 12.0 nM 7.92 Inhibition of [3H]- Kainate binding to Ionotropic glutamate receptor kainate in ... 8893837
Glutamate receptor 2 Ki = 16.8 nM 7.78 Displacement of (R,S)-[5-methyl-3H]AMPA from rat recombinant flop iGluR2(R) expr... 18811139
Glutamate receptor 2 Ki = 17.0 nM 7.77 Binding affinity of compound was determined towards cloned Ionotropic glutamate ... 12747796
Glutamate receptor ionotropic AMPA IC50 = 19.0 nM 7.72 Inhibition of the binding of radioligand [3H]AMPA in the presence at high-affini... 1825114
Unchecked Ki = 19.0 nM 7.72 DRUGMATRIX: Glutamate, AMPA radioligand binding (ligand: [3H] AMPA) -
Glutamate receptor 3 Ki = 20.6 nM 7.69 Displacement of (R,S)-[5-methyl-3H]AMPA from rat recombinant flop iGluR3 express... 18811139
Glutamate receptor 3 Ki = 21.0 nM 7.68 Binding affinity of compound was determined towards cloned Ionotropic glutamate ... 12747796
Glutamate receptor 1 Ki = 21.9 nM 7.66 Displacement of (R,S)-[5-methyl-3H]AMPA from rat recombinant flop iGluR1 express... 18811139
Glutamate receptor 1 Ki = 22.0 nM 7.66 Binding affinity of compound was determined towards cloned Ionotropic glutamate ... 12747796
Glutamate receptor ionotropic AMPA IC50 = 23.0 nM 7.64 In vitro binding affinity against Ionotropic glutamate receptor AMPA using [3H]A... 9288165
Unchecked IC50 = 24.0 nM 7.62 DRUGMATRIX: Glutamate, AMPA radioligand binding (ligand: [3H] AMPA) -
Unchecked IC50 = 39.0 nM 7.41 Displacement of [3H]AMPA from AMPA receptor in rat synaptosomes 17455929
Unchecked IC50 = 39.0 nM 7.41 Displacement of [3H]AMPA from AMPA receptor in Sprague-Dawley rat brain membrane... 20408529
Glutamate receptor ionotropic, AMPA IC50 = 40.0 nM 7.4 Compound was evaluated for the inhibition of binding of [3H]AMPA to the AMPA rec... 7512140
Glutamate receptor ionotropic, AMPA IC50 = 40.0 nM 7.4 Binding affinity by measuring displacement of [3H]AMPA from Ionotropic glutamate... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5303304 HEK-293T 9
- 10.6019/CHEMBL5303304 U2OS 6
11754576 10.1021/jm010303j No relevant target 6
- 10.6019/CHEMBL5303304 Fibroblast 4
1825114 10.1021/jm00105a019 Glutamate receptor ionotropic AMPA 4
9046343 10.1021/jm9607212 ADMET 3
8558509 10.1021/jm9502908 No relevant target 3
17455929 10.1021/jm061439q Unchecked 3
12747796 10.1021/jm020588f Glutamate receptor 1 3
1825114 10.1021/jm00105a019 Rattus norvegicus 2
9526567 10.1021/jm9706731 Mus musculus 2
7512140 10.1021/jm00033a003 Glutamate NMDA receptor 2
7512140 10.1021/jm00033a003 Rattus norvegicus 2
20096591 10.1016/j.bmc.2009.12.072 Glutamate receptor 1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
1383544 10.1021/jm00097a008 Glutamate receptor ionotropic, AMPA 2
20096591 10.1016/j.bmc.2009.12.072 Glutamate receptor 3 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
12747796 10.1021/jm020588f Glutamate receptor 3 2
20408529 10.1021/jm1001452 Unchecked 2

Data from ChEMBL 36 via Core Engine