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Compound Detail

CHEMBL79140

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N[C@H](C(=O)O)[C@H](OCc1ccccc1)C(=O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL79140
Phase Preclinical
Structure Type MOL
InChI Key BYOBCYXURWDEDS-IUCAKERBSA-N
5
Targets
33
Activities
1
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

239.2
MW (Da)
0.07
ALogP
4
HBA
3
HBD
109.8
PSA (Ų)
0.65
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C11H13NO5
MW 239.23
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 0.31

Activity Summary

IC50 33 meas. best 6.02

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Excitatory amino acid transporter 2
CHEMBL4973
 IC50 6.02 5.4713 955.0 8
Unchecked
CHEMBL612545
 IC50 5.89 5.89 1300.0 1
Excitatory amino acid transporter 1
CHEMBL3085
 IC50 5.8 5.2933 1600.0 6
Excitatory amino acid transporter 4
CHEMBL3700
 IC50 5.64 5.64 2290.9 2
Excitatory amino acid transporter 3
CHEMBL2721
 IC50 5.43 5.2325 3700.0 8

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Excitatory amino acid transporter 2 IC50 = 954.99 nM 6.02 Inhibition of [3H]-D-Asp uptake at human EAAT2 expressed in HEK293 cells measure... 27636002
Excitatory amino acid transporter 2 IC50 = 960.0 nM 6.02 Inhibition of [3H]-D-Asp uptake at human EAAT2 expressed in HEK293 cells measure... 27636002
Unchecked IC50 = 1300.0 nM 5.89 Glutamate uptake inhibition assay on glutamate transporters (excitatory amino ac... 12617931
Excitatory amino acid transporter 1 IC50 = 1600.0 nM 5.8 Inhibition of [3H]-D-Asp uptake at human EAAT1 expressed in HEK293 cells measure... 27636002
Excitatory amino acid transporter 1 IC50 = 1621.81 nM 5.79 Inhibition of [3H]-D-Asp uptake at human EAAT1 expressed in HEK293 cells measure... 27636002
Excitatory amino acid transporter 2 IC50 = 1900.0 nM 5.72 Inhibition of human EAAT2 expressed in HEK293 cells assessed as reduction in [3H... 30011368
Excitatory amino acid transporter 2 IC50 = 1905.46 nM 5.72 Inhibition of human EAAT2 expressed in HEK293 cells assessed as reduction in [3H... 30011368
Excitatory amino acid transporter 1 IC50 = 2100.0 nM 5.68 Inhibition of human EAAT1 expressed in HEK293 cells assessed as reduction in [3H... 30011368
Excitatory amino acid transporter 1 IC50 = 2089.3 nM 5.68 Inhibition of human EAAT1 expressed in HEK293 cells assessed as reduction in [3H... 30011368
Excitatory amino acid transporter 4 IC50 = 2300.0 nM 5.64 Inhibition of rat EAAT4 expressed in tsA201 cells assessed as reduction in [3H]-... 30011368
Excitatory amino acid transporter 4 IC50 = 2290.87 nM 5.64 Inhibition of rat EAAT4 expressed in tsA201 cells assessed as reduction in [3H]-... 30011368
Excitatory amino acid transporter 3 IC50 = 3715.35 nM 5.43 Inhibition of [3H]-D-Asp uptake at human EAAT3 expressed in HEK293 cells measure... 27636002
Excitatory amino acid transporter 3 IC50 = 3700.0 nM 5.43 Inhibition of [3H]-D-Asp uptake at human EAAT3 expressed in HEK293 cells measure... 27636002
Excitatory amino acid transporter 2 IC50 = 3800.0 nM 5.42 Concentration required for blocking [14C]glutamate uptake in COS-1 cells express... 11078189
Excitatory amino acid transporter 2 IC50 = 3800.0 nM 5.42 Inhibition of human GLT1 expressed in Xenopus laevis Oocytes assessed as reducti... 20812729
Excitatory amino acid transporter 3 IC50 = 3800.0 nM 5.42 Inhibition of human EAAT3 expressed in HEK293 cells assessed as reduction in [3H... 30011368
Excitatory amino acid transporter 3 IC50 = 3801.89 nM 5.42 Inhibition of human EAAT3 expressed in HEK293 cells assessed as reduction in [3H... 30011368
Excitatory amino acid transporter 2 IC50 = 5500.0 nM 5.26 Inhibition of human EAAT2 transfected in African green monkey COS-1 cells assess... 36787643
Excitatory amino acid transporter 3 IC50 = 7000.0 nM 5.16 Concentration required for blocking [14C]glutamate uptake in COS-1 cells express... 11078189
Excitatory amino acid transporter 3 IC50 = 7000.0 nM 5.16 Inhibition of [14C]glutamate uptake at human EAAT3 expressed in african green mo... 18650095

Literature References

PubMed DOI Target Context # Activities
11078189 10.1016/s0960-894x(00)00487-x Excitatory amino acid transporter 2 12
11078189 10.1016/s0960-894x(00)00487-x Excitatory amino acid transporter 3 12
11078189 10.1016/s0960-894x(00)00487-x Excitatory amino acid transporter 1 12
36787643 10.1021/acs.jmedchem.2c01572 Unchecked 2
30011368 10.1021/acs.jmedchem.8b00700 Excitatory amino acid transporter 4 2
30011368 10.1021/acs.jmedchem.8b00700 Excitatory amino acid transporter 3 2
30011368 10.1021/acs.jmedchem.8b00700 Excitatory amino acid transporter 1 2
30011368 10.1021/acs.jmedchem.8b00700 Excitatory amino acid transporter 2 2
27636002 10.1021/acs.jmedchem.6b01066 Excitatory amino acid transporter 3 2
27636002 10.1021/acs.jmedchem.6b01066 Excitatory amino acid transporter 2 2
27636002 10.1021/acs.jmedchem.6b01066 Excitatory amino acid transporter 1 2
18578477 10.1021/jm800091e Unchecked 2
20812729 10.1021/jm100959g Excitatory amino acid transporter 3 1
20812729 10.1021/jm100959g Excitatory amino acid transporter 2 1
18650095 10.1016/j.bmc.2008.07.001 Excitatory amino acid transporter 3 1
18578477 10.1021/jm800091e Glutamate NMDA receptor 1
18578477 10.1021/jm800091e Glutamate receptor ionotropic, kainate 1 1
18578477 10.1021/jm800091e Glutamate receptor ionotropic, kainate 2 1
18578477 10.1021/jm800091e Glutamate receptor ionotropic, kainate 3 1
36787643 10.1021/acs.jmedchem.2c01572 Excitatory amino acid transporter 1 1

Data from ChEMBL 36 via Core Engine