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Compound Detail

CHEMBL474133

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COc1ccc(C2C(C#N)=C(N)OC3=C2C(=O)CC(c2cccc4ccccc24)C3)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL474133
Phase Preclinical
Structure Type MOL
InChI Key YBMGNDPBARCLFT-UHFFFAOYSA-N
2
Targets
11
Activities
1
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

422.5
MW (Da)
5.06
ALogP
5
HBA
1
HBD
85.3
PSA (Ų)
0.64
QED
1
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C27H22N2O3
MW 422.48
Aromatic Rings 3
Heavy Atoms 32
NP-Likeness -0.73

Activity Summary

IC50 11 meas. best 6.92

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Excitatory amino acid transporter 1
CHEMBL3085
 IC50 6.92 6.2344 120.0 9
Excitatory amino acid transporter 1
CHEMBL4190
 IC50 6.02 6.015 955.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 0.5 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Excitatory amino acid transporter 1 IC50 = 120.0 nM 6.92 Activity at human EAAT1 expressed in HEK293 cells assessed as inhibition of Glu-... 19161278
Excitatory amino acid transporter 1 IC50 = 123.03 nM 6.91 Activity at human EAAT1 expressed in HEK293 cells assessed as inhibition of Glu-... 19161278
Excitatory amino acid transporter 1 IC50 = 660.0 nM 6.18 Displacement of [3H]D-Asp from human EAAT1 receptor expressed in HEK293 cells 19161278
Excitatory amino acid transporter 1 IC50 = 660.69 nM 6.18 Displacement of [3H]D-Asp from human EAAT1 receptor expressed in HEK293 cells 19161278
Excitatory amino acid transporter 1 IC50 = 660.0 nM 6.18 Inhibition of human EAAT1 expressed in HEK293 cells by [3H]D-Asp uptake assay 20857912
Excitatory amino acid transporter 1 IC50 = 660.69 nM 6.18 Inhibition of human EAAT1 expressed in HEK293 cells by [3H]D-Asp uptake assay 20857912
Excitatory amino acid transporter 1 IC50 = 660.0 nM 6.18 Inhibition of human EAAT1 expressed in HEK293 cells assessed as inhibition of 3[... 22594609
Excitatory amino acid transporter 1 IC50 = 660.0 nM 6.18 Inhibition of EAAT1 (unknown origin) stably expressed in HEK293 cells assessed a... 31774679
Excitatory amino acid transporter 1 IC50 = 954.99 nM 6.02 Activity at rat EAAT1 expressed in TSA201 cells assessed as inhibition of Glu-in... 19161278
Excitatory amino acid transporter 1 IC50 = 970.0 nM 6.01 Activity at rat EAAT1 expressed in TSA201 cells assessed as inhibition of Glu-in... 19161278
Excitatory amino acid transporter 1 IC50 = 6300.0 nM 5.2 Inhibition of the Excitatory Amino Acid Transporter 1 (EAAT1, SLC1A3) as assesse... 35677430

Literature References

PubMed DOI Target Context # Activities
19161278 10.1021/jm8013458 Excitatory amino acid transporter 1 7
19161278 10.1021/jm8013458 Excitatory amino acid transporter 2 3
19161278 10.1021/jm8013458 Excitatory amino acid transporter 3 3
19161278 10.1021/jm8013458 Unchecked 2
20857912 10.1021/jm1009154 Excitatory amino acid transporter 1 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL5724796 Bromodomain-containing protein 4 1
- 10.6019/CHEMBL5724796 Tyrosine-protein kinase ABL1 1
- 10.6019/CHEMBL5724796 Aurora kinase A 1
- 10.6019/CHEMBL5724796 Mitogen-activated protein kinase 1 1
- 10.6019/CHEMBL5724796 Glycogen synthase kinase-3 beta 1
- 10.6019/CHEMBL5724796 Cyclin-dependent kinase 2 1
- 10.6019/CHEMBL5724796 Casein kinase I isoform delta 1
35677430 10.3389/fphar.2022.872335 Excitatory amino acid transporter 1 1
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 1
31774679 10.1021/acs.jmedchem.9b01237 Excitatory amino acid transporter 1 1
22594609 10.1021/jm300345z Excitatory amino acid transporter 1 1
20857912 10.1021/jm1009154 Rattus norvegicus 1
20857912 10.1021/jm1009154 Excitatory amino acid transporter 3 1
20857912 10.1021/jm1009154 Excitatory amino acid transporter 2 1

Data from ChEMBL 36 via Core Engine