Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL59030

Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
O=C(O)Cc1cccc(OCCCN(Cc2cccc(C(F)(F)F)c2Cl)CC(c2ccccc2)c2ccccc2)c1

Basic Information

ChEMBL ID CHEMBL59030
Phase Preclinical
Structure Type MOL
InChI Key NAXSRXHZFIBFMI-UHFFFAOYSA-N
13
Targets
75
Activities
4
Assay Types
8
PK Parameters
20
Publications
0
Known Names

Molecular Properties

582.1
MW (Da)
8.09
ALogP
3
HBA
1
HBD
49.8
PSA (Ų)
0.16
QED
2
Ro5 Violations
13
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug Chemical Probe

Extended Properties

Molecular Formula C33H31ClF3NO3
MW 582.06
Aromatic Rings 4
Heavy Atoms 41
NP-Likeness -0.81

Activity Summary

EC50 54 meas. best 9.64
IC50 17 meas. best 8.1
Ki 3 meas. best 8.66
Kd 1 meas. best 5.16

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Retinoic acid receptor RXR-alpha/oxysterols receptor LXR-beta
CHEMBL3430878
EC50 9.64 9.64 0.2 1
Retinoic acid receptor RXR-alpha/oxysterols receptor LXR-alpha
CHEMBL3430879
EC50 9.4 9.4 0.4 1
Oxysterols receptor LXR-beta
CHEMBL4093
Ki 8.66 8.66 2.2 2
Oxysterols receptor LXR-beta
CHEMBL4093
EC50 8.4 7.2118 4.0 22
Oxysterols receptor LXR-beta
CHEMBL4093
IC50 8.1 7.772 7.9 5
THP-1
CHEMBL614245
EC50 8.0 7.4675 10.0 4
THP-1
CHEMBL614245
IC50 7.7 7.7 20.0 1
Unchecked
CHEMBL612545
EC50 7.7 7.235 20.0 2
Oxysterols receptor LXR-alpha
CHEMBL2808
EC50 7.66 6.603 22.0 20
RAW264.7
CHEMBL612557
EC50 7.54 7.54 29.0 1
Unchecked
CHEMBL612545
IC50 7.52 6.42 30.0 2
Mus musculus
CHEMBL375
EC50 7.3 7.3 50.0 1
Oxysterols receptor LXR-alpha
CHEMBL2808
IC50 7.0 6.9075 100.0 4
HepG2
CHEMBL395
EC50 6.68 6.19 210.0 2
Schistosoma mansoni
CHEMBL612893
IC50 5.7 5.69 2000.0 2
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
Ki 5.7 5.7 2000.0 1
U-87 MG
CHEMBL614247
IC50 5.44 5.44 3650.0 1
Oxysterols receptor LXR-alpha
CHEMBL2808
Kd 5.16 5.16 6970.0 1
SARS-CoV-2
CHEMBL4303835
IC50 4.56 4.56 27710.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 2.0 uM.hr.Kg/mg Mus musculus
AUC 1867.0 ng/g.hr Mus musculus
AUC 8853.0 ng/g.hr Mus musculus
CL 8.0 mL.min-1.kg-1 Mus musculus
Cmax 21819.06 nM Mus musculus
F 70.0 % -
T1/2 2.0 hr Mus musculus
T1/2 3.4 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Retinoic acid receptor RXR-alpha/oxysterols receptor LXR-beta EC50 = 0.228 nM 9.64 Agonist activity at human RXRalpha/LXRbeta expressed in HEK293 cells measured af... 32248003
Retinoic acid receptor RXR-alpha/oxysterols receptor LXR-alpha EC50 = 0.401 nM 9.4 Agonist activity at human RXRalpha/LXRalpha expressed in HEK293 cells measured a... 32248003
Oxysterols receptor LXR-beta Ki = 2.2 nM 8.66 Binding affinity to recombinant human LXRbeta-LBD expressed in Escherichia coli ... 31202993
Oxysterols receptor LXR-beta Ki = 2.2 nM 8.66 Displacement of hyodeoxycholicacid-based fluorescent tracer from recombinant hum... 32248003
Oxysterols receptor LXR-beta EC50 = 4.0 nM 8.4 Activity at human LXRbeta by Gal4 transactivation assay 17665897
Oxysterols receptor LXR-beta EC50 = 5.0 nM 8.3 Binding to human LXRbeta 26990539
Oxysterols receptor LXR-beta IC50 = 7.943 nM 8.1 Displacement of [N-methyl-3H]T1317 from human biotinylated LXRbeta LBD after 3 h... 20345102
THP-1 EC50 = 10.0 nM 8.0 Induction of cholesterol efflux in THP1 cells 17587573
THP-1 EC50 = 10.0 nM 8.0 Induction of cholesterol efflux in THP1 cells after 18 hrs 17416521
Oxysterols receptor LXR-beta IC50 = 12.0 nM 7.92 Displacement of [3H]TO901317 from human recombinant LXRbeta expressed in Escheri... 18973288
Oxysterols receptor LXR-beta IC50 = 12.0 nM 7.92 Displacement of [3H]T-0901317 from human LXR beta receptor 17034119
Oxysterols receptor LXR-beta EC50 = 15.0 nM 7.82 Agonist activity at human LXRbeta receptor transfected in COS7 cells after 16 hr... 17587573
Oxysterols receptor LXR-beta EC50 = 15.0 nM 7.82 Activation of LXRbeta co-transfected in COS7 cells with RXRalpha by reporter tra... 17416521
THP-1 IC50 = 20.0 nM 7.7 Antiinflammatory activity against human THP1 cells assessed as inhibition of LPS... 18800767
Oxysterols receptor LXR-beta EC50 = 20.0 nM 7.7 Effective concentration for Steroid receptor coactivator-1 (SRC1) recruitment to... 16107141
Unchecked EC50 = 20.0 nM 7.7 Protac activity at VHL/LXR (unknown origin) by TR-FRET assay 34656901
Oxysterols receptor LXR-alpha EC50 = 22.0 nM 7.66 Binding affinity to human LXRalpha 26990539
Oxysterols receptor LXR-beta EC50 = 25.0 nM 7.6 Agonist activity at LXRbeta by FRET assay 19167885
Oxysterols receptor LXR-beta EC50 = 27.0 nM 7.57 Agonist activity at GAL-linked human LXRbeta expressed in THP1 cells assessed as... 17665897
RAW264.7 EC50 = 29.0 nM 7.54 Induction of [3H]cholesterol efflux in mouse RAW264.7 cells loaded with acetylat... 19717304

Literature References

PubMed DOI Target Context # Activities
20350005 10.1021/jm100034x Mus musculus 81
16529931 10.1016/j.bmcl.2006.02.050 Mus musculus 16
18324758 10.1021/jm7011326 THP-1 14
19717304 10.1016/j.bmcl.2009.08.036 Macrophage 7
31499362 10.1016/j.ejmech.2019.111647 Unchecked 6
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
17665897 10.1021/jm070453f Oxysterols receptor LXR-alpha 5
18973288 10.1021/jm800799q Mus musculus 5
17665897 10.1021/jm070453f Oxysterols receptor LXR-beta 5
18973288 10.1021/jm800799q THP-1 4
11985463 10.1021/jm0255116 Oxysterols receptor LXR-alpha 4
17416521 10.1016/j.bmcl.2007.03.076 THP-1 4
18973288 10.1021/jm800799q HepG2 4
23844653 10.1021/jm301913k Oxysterols receptor LXR-beta 4
18800767 10.1021/jm800612u Oxysterols receptor LXR-beta 3
17391964 10.1016/j.bmc.2007.03.013 Mus musculus 3
18973288 10.1021/jm800799q Oxysterols receptor LXR-beta 3
18800767 10.1021/jm800612u RAW264.7 3
17587573 10.1016/j.bmcl.2007.06.017 Oxysterols receptor LXR-beta 3
17587573 10.1016/j.bmcl.2007.06.017 THP-1 3

Data from ChEMBL 36 via Core Engine