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Compound Detail

CHEMBL288166

2S,4R-4-METHYLGLUTAMATE
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C[C@H](C[C@H](N)C(=O)O)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL288166
Name 2S,4R-4-METHYLGLUTAMATE
Phase Preclinical
Structure Type MOL
InChI Key KRKRAOXTGDJWNI-DMTCNVIQSA-N
10
Targets
18
Activities
3
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

161.2
MW (Da)
-0.49
ALogP
3
HBA
3
HBD
100.6
PSA (Ų)
0.52
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C6H11NO4
MW 161.16
Aromatic Rings 0
Heavy Atoms 11
NP-Likeness 1.17

Activity Summary

Ki 12 meas. best 9.18
EC50 3 meas. best 6.25
IC50 3 meas. best 7.46

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Glutamate receptor ionotropic, kainate 1
CHEMBL2919
 Ki 9.18 9.18 0.7 2
Glutamate receptor ionotropic, kainate 1
CHEMBL1918
 Ki 8.52 8.52 3.0 1
Glutamate receptor ionotropic, kainate 3
CHEMBL3744
 Ki 8.33 8.285 4.7 2
Glutamate receptor ionotropic, kainate 2
CHEMBL3683
 Ki 8.0 8.0 10.0 1
Glutamate receptor ionotropic, kainate 2
CHEMBL3607
 Ki 7.83 7.8 14.8 2
Glutamate receptor ionotropic, kainate
CHEMBL2094119
 IC50 7.46 7.46 35.0 2
Unchecked
CHEMBL612545
 EC50 6.25 5.47 558.0 3
Metabotropic glutamate receptor 6
CHEMBL4573
 IC50 5.4 5.4 4000.0 1
Excitatory amino acid transporter 3
CHEMBL2721
 Ki 5.27 5.225 5370.3 2
Excitatory amino acid transporter 2
CHEMBL4973
 Ki 4.93 4.91 11749.0 2

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Glutamate receptor ionotropic, kainate 1 Ki = 0.663 nM 9.18 Displacement of [3H]SYM2081 from rat recombinant iGluR5 18578478
Glutamate receptor ionotropic, kainate 1 Ki = 0.6607 nM 9.18 Displacement of [3H]SYM2081 from rat recombinant iGluR5 18578478
Glutamate receptor ionotropic, kainate 1 Ki = 3.0 nM 8.52 Binding affinity against human ionotropic glutamate receptor kainate 1 in HK293 ... 10821708
Glutamate receptor ionotropic, kainate 3 Ki = 4.677 nM 8.33 Displacement of [3H]SYM2081 from rat recombinant iGluR7 18578478
Glutamate receptor ionotropic, kainate 3 Ki = 5.69 nM 8.24 Displacement of [3H]SYM2081 from rat recombinant iGluR7 18578478
Glutamate receptor ionotropic, kainate 2 Ki = 10.0 nM 8.0 Binding affinity against human ionotropic glutamate receptor ionotropic kainate ... 10821708
Glutamate receptor ionotropic, kainate 2 Ki = 14.79 nM 7.83 Displacement of [3H]SYM2081 from rat recombinant iGluR6 18578478
Glutamate receptor ionotropic, kainate 2 Ki = 17.0 nM 7.77 Displacement of [3H]SYM2081 from rat recombinant iGluR6 18578478
Glutamate receptor ionotropic, kainate IC50 = 35.0 nM 7.46 Compound was tested for inhibition of [3H]kainate (KA) binding to cortical membr... -
Glutamate receptor ionotropic, kainate IC50 = 35.0 nM 7.46 Ability to inhibit [3H]-KA binding to Ionotropic glutamate receptor kainate from... 7629789
Unchecked EC50 = 558.0 nM 6.25 Agonist activity at Non-desensitized homomeric rat GluK1(Q)1b mutant expressed i... 21619066
Unchecked EC50 = 1550.0 nM 5.81 Agonist activity at rat GluK2 mutant expressed in Xenopus oocytes by two-electro... 21619066
Metabotropic glutamate receptor 6 IC50 = 4000.0 nM 5.4 Antagonist activity at human recombinant GluR6 expressed in HEK cells coexpressi... 19819046
Excitatory amino acid transporter 3 Ki = 5370.32 nM 5.27 Binding affinity to human EAAT3 expressed in HEK293 cells in FMP (FLPR) assay 16335922
Excitatory amino acid transporter 3 Ki = 6600.0 nM 5.18 Binding affinity to human EAAT3 expressed in HEK293 cells in FMP (FLPR) assay 16335922
Excitatory amino acid transporter 2 Ki = 11748.98 nM 4.93 Binding affinity to human EAAT2 expressed in HEK293 cells in FMP (FLPR) assay 16335922
Excitatory amino acid transporter 2 Ki = 13000.0 nM 4.89 Binding affinity to human EAAT2 expressed in HEK293 cells in FMP (FLPR) assay 16335922
Unchecked EC50 = 45100.0 nM 4.35 Agonist activity at non-desensitized homomeric rat GluK3 mutant expressed in Xen... 21619066

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 U2OS 320
- 10.6019/CHEMBL5724801 Fibroblast 320
- 10.6019/CHEMBL5724801 HEK-293T 320
21619066 10.1021/jm2004078 Unchecked 6
- 10.6019/CHEMBL5303304 Fibroblast 5
- 10.6019/CHEMBL5303304 U2OS 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
18578478 10.1021/jm800092x Glutamate receptor ionotropic, kainate 3 2
18578478 10.1021/jm800092x Glutamate receptor ionotropic, kainate 2 2
16335922 10.1021/jm050597z Excitatory amino acid transporter 1 2
16335922 10.1021/jm050597z Excitatory amino acid transporter 2 2
16335922 10.1021/jm050597z Excitatory amino acid transporter 3 2
18578478 10.1021/jm800092x Glutamate receptor ionotropic, kainate 1 2
7629789 10.1021/jm00014a002 Glutamate receptor ionotropic, NMDA 2C 1
7629789 10.1021/jm00014a002 Glutamate receptor ionotropic, kainate 1
- 10.1016/0960-894X(95)00335-Q Glutamate NMDA receptor 1
- 10.1016/0960-894X(95)00335-Q Glutamate receptor ionotropic, kainate 1
10229625 10.1021/jm980571q Metabotropic glutamate receptor 2 1
10821708 10.1021/jm9911682 Unchecked 1

Data from ChEMBL 36 via Core Engine