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Compound Detail

CHEMBL4066040

A-1596584
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COc1ccc2c(c1)O[C@H](c1ccc(OC)c(OC)c1)C[C@@H]2NC(=O)C1(c2ccc3c(c2)OC(F)(F)O3)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL4066040
Name A-1596584
Phase Preclinical
Structure Type MOL
InChI Key KDOQEEMQPHIANX-REWPJTCUSA-N
5
Targets
13
Activities
2
Assay Types
2
PK Parameters
20
Publications
0
Known Names

Molecular Properties

539.5
MW (Da)
5.45
ALogP
7
HBA
1
HBD
84.5
PSA (Ų)
0.43
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C29H27F2NO7
MW 539.53
Aromatic Rings 3
Heavy Atoms 39
NP-Likeness -0.17

Activity Summary

Ki 9 meas. best 6.66
EC50 4 meas. best 6.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Gamma-aminobutyric acid receptor subunit alpha-1
CHEMBL1962
 Ki 6.66 6.66 217.7 1
Unchecked
CHEMBL612545
 Ki 6.66 6.66 217.7 2
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 6.23 6.23 584.0 3
Cystic fibrosis transmembrane conductance regulator
CHEMBL4051
 EC50 6.0 5.705 1000.0 4
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 5.56 5.56 2740.3 3

Pharmacokinetic Data

Parameter Value Units Species
CL 20833.33 mL.min-1.kg-1 Homo sapiens
CL 12916.67 mL.min-1.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked Ki = 217.72 nM 6.66 GPCRScan assay: inhibition of GABA/PBR -
Unchecked Ki = 218.78 nM 6.66 GPCRScan assay: inhibition of GABA/PBR -
Gamma-aminobutyric acid receptor subunit alpha-1 Ki = 217.72 nM 6.66 Selectivity interaction (GPCR panel (PDSP screen)) EUB0000264b GABRA1 -
Sigma intracellular receptor 2 Ki = 583.98 nM 6.23 GPCRScan assay: inhibition of Sigma 2 -
Sigma intracellular receptor 2 Ki = 588.84 nM 6.23 GPCRScan assay: inhibition of Sigma 2 -
Sigma intracellular receptor 2 Ki = 583.98 nM 6.23 Selectivity interaction (GPCR panel (PDSP screen)) EUB0000264b TMEM97 -
Cystic fibrosis transmembrane conductance regulator EC50 = 1000.0 nM 6.0 Corrector activity at HRP-fused CFTR F508del mutant (unknown origin) expressed i... 29251932
Cystic fibrosis transmembrane conductance regulator EC50 = 1000.0 nM 6.0 CSE-HRP surface expression (Cell surface expression-horseradish peroxidase) assa... -
Sigma non-opioid intracellular receptor 1 Ki = 2740.31 nM 5.56 GPCRScan assay: inhibition of Sigma 1 -
Sigma non-opioid intracellular receptor 1 Ki = 2754.23 nM 5.56 GPCRScan assay: inhibition of Sigma 1 -
Sigma non-opioid intracellular receptor 1 Ki = 2740.31 nM 5.56 Selectivity interaction (GPCR panel (PDSP screen)) EUB0000264b SIGMAR1 -
Cystic fibrosis transmembrane conductance regulator EC50 = 3900.0 nM 5.41 Plasma membrane-expressed enzyme acceptor protein (EA-MEM) assay -
Cystic fibrosis transmembrane conductance regulator EC50 = 3900.0 nM 5.41 Affinity Phenotypic Cellular interaction (Plasma membrane-expressed enzyme accep... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4507262 Tyrosine-protein kinase ABL1 15
- 10.6019/CHEMBL4507262 Epidermal growth factor receptor 12
- 10.6019/CHEMBL5674860 Colon cancer organoid 12
- 10.6019/CHEMBL5724558 Colon cancer organoid 12
- 10.6019/CHEMBL4507262 Receptor-type tyrosine-protein kinase FLT3 11
- 10.6019/CHEMBL4507262 Unchecked 11
- 10.6019/CHEMBL4689842 HEK-293T 10
- 10.6019/CHEMBL4507262 Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform 10
- 10.6019/CHEMBL4507262 Mast/stem cell growth factor receptor Kit 9
- 10.6019/CHEMBL4689842 U2OS 8
- 10.6019/CHEMBL4689842 Fibroblast 8
- 10.6019/CHEMBL5608141 Colon cancer organoid 6
- 10.1158/2159-8290.CD-23-0050 Colon cancer organoid 5
- 10.6019/CHEMBL4507262 Proto-oncogene tyrosine-protein kinase receptor Ret 4
- 10.6019/CHEMBL4507262 Sigma non-opioid intracellular receptor 1 4
- 10.6019/CHEMBL4507262 Cystic fibrosis transmembrane conductance regulator 4
- 10.6019/CHEMBL4507262 GABA-A receptor; anion channel 4
- 10.6019/CHEMBL4507262 Sigma intracellular receptor 2 3
- 10.6019/CHEMBL4507262 ALK tyrosine kinase receptor 3
29251932 10.1021/acs.jmedchem.7b01339 Cystic fibrosis transmembrane conductance regulator 3

Data from ChEMBL 36 via Core Engine