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Compound Detail

CHEMBL214719

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O=C(O)Cc1ccc(COc2cccc(-c3c(Cc4ccccc4)cnc4c(C(F)(F)F)cccc34)c2)cc1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL214719
Phase Preclinical
Structure Type MOL
InChI Key VXHRQVMQVYQGQG-UHFFFAOYSA-N
12
Targets
46
Activities
2
Assay Types
1
PK Parameters
20
Publications
0
Known Names

Molecular Properties

527.5
MW (Da)
7.72
ALogP
3
HBA
1
HBD
59.4
PSA (Ų)
0.22
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C32H24F3NO3
MW 527.54
Aromatic Rings 5
Heavy Atoms 39
NP-Likeness -0.48

Activity Summary

EC50 34 meas. best 8.22
IC50 12 meas. best 8.7

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Oxysterols receptor LXR-beta
CHEMBL4093
 IC50 8.7 8.688 2.0 5
THP-1
CHEMBL614245
 EC50 8.22 7.572 6.0 5
Oxysterols receptor LXR-alpha
CHEMBL2808
 IC50 8.02 8.012 9.5 5
Oxysterols receptor LXR-beta
CHEMBL2417346
 EC50 7.39 7.39 41.0 1
J774.A1
CHEMBL614040
 EC50 7.39 7.39 41.0 1
J774
CHEMBL614123
 EC50 7.39 7.39 41.0 2
Huh-7
CHEMBL614039
 EC50 7.35 7.065 45.0 2
Oxysterols receptor LXR-beta
CHEMBL4093
 EC50 7.15 7.0757 71.0 7
HepG2
CHEMBL395
 EC50 6.92 6.7833 120.0 3
Liver X receptor
CHEMBL3706564
 EC50 6.65 6.65 224.0 1
Oxysterols receptor LXR-alpha
CHEMBL2808
 EC50 6.62 6.62 238.0 5
Peroxisome proliferator-activated receptor gamma
CHEMBL235
 EC50 6.2 6.18 630.0 3
Peroxisome proliferator-activated receptor delta
CHEMBL3979
 EC50 6.2 6.185 627.0 2
Peroxisome proliferator-activated receptor alpha
CHEMBL239
 EC50 5.88 5.88 1310.0 2

Pharmacokinetic Data

Parameter Value Units Species
T1/2 1.783 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Oxysterols receptor LXR-beta IC50 = 2.0 nM 8.7 Binding affinity at human LXRbeta 18023179
Oxysterols receptor LXR-beta IC50 = 2.0 nM 8.7 Displacement of [3H]TO901317 from human recombinant LXRbeta expressed in Escheri... 18973288
Oxysterols receptor LXR-beta IC50 = 2.1 nM 8.68 Displacement of [3H]T-0901317 from human LXR beta receptor 17034119
Oxysterols receptor LXR-beta IC50 = 2.1 nM 8.68 Displacement of [3H]T0901317 from human recombinant N-terminal biotinylated tagg... 19162487
Oxysterols receptor LXR-beta IC50 = 2.1 nM 8.68 Displacement of [3H]T0901317 from human recombinant LXRbeta ligand binding domai... 19853462
THP-1 EC50 = 6.0 nM 8.22 Stimulation of [3H]cholesterol efflux in human THP1 foam cells loaded with ac-LD... 19962892
THP-1 EC50 = 6.0 nM 8.22 Stimulation of [3H]cholesterol efflux in human THP1 foam cells loaded with ac-LD... 18973288
Oxysterols receptor LXR-alpha IC50 = 9.5 nM 8.02 Displacement of [3H]T-0901317 from human LXR alpha receptor 17034119
Oxysterols receptor LXR-alpha IC50 = 9.5 nM 8.02 Displacement of [3H]T0901317 from human recombinant N-terminal biotinylated tagg... 19162487
Oxysterols receptor LXR-alpha IC50 = 9.5 nM 8.02 Displacement of [3H]T0901317 from human recombinant LXRalpha ligand binding doma... 19853462
Oxysterols receptor LXR-alpha IC50 = 10.0 nM 8.0 Binding affinity at human LXRalpha 18023179
Oxysterols receptor LXR-alpha IC50 = 10.0 nM 8.0 Displacement of [3H]TO901317 from human recombinant LXRalpha expressed in Escher... 18973288
J774 EC50 = 41.0 nM 7.39 Effect on ABCA1 gene expression in mouse J774 cells 18023179
J774 EC50 = 41.0 nM 7.39 Induction of ABCA1 mRNA expression in mouse J774 cells 19162487
J774.A1 EC50 = 41.0 nM 7.39 Induction of ABCA1 mRNA expression in mouse J774A1 cells after 18 hrs by RT-PCR 19394832
Oxysterols receptor LXR-beta EC50 = 41.0 nM 7.39 Agonist activity at LXRbeta in mouse J774 cells assessed as upregulation of ABCA... 19853462
Huh-7 EC50 = 45.0 nM 7.35 Induction of SREBP1c expression in Huh7 cell line 17034119
THP-1 EC50 = 55.0 nM 7.26 Induction of ABCA1 expression in THP1 cell line 17034119
Oxysterols receptor LXR-beta EC50 = 71.0 nM 7.15 Agonist activity at human recombinant LXRbeta expressed in CHO cells assessed as... 19853462
Oxysterols receptor LXR-beta EC50 = 71.0 nM 7.15 Agonist activity at human LXR beta receptor expressed in CHO cells by reporter a... 17034119

Literature References

PubMed DOI Target Context # Activities
18973288 10.1021/jm800799q Syrian golden hamster 16
17034119 10.1021/jm0609566 Oxysterols receptor LXR-beta 5
19853462 10.1016/j.bmc.2009.10.001 Oxysterols receptor LXR-beta 5
18973288 10.1021/jm800799q THP-1 4
18973288 10.1021/jm800799q HepG2 4
17034119 10.1021/jm0609566 THP-1 3
19394832 10.1016/j.bmc.2009.04.012 Oxysterols receptor LXR-alpha 3
19162487 10.1016/j.bmc.2008.12.048 Oxysterols receptor LXR-beta 3
18023179 10.1016/j.bmcl.2007.11.013 Oxysterols receptor LXR-beta 3
18023179 10.1016/j.bmcl.2007.11.013 Oxysterols receptor LXR-alpha 3
19162487 10.1016/j.bmc.2008.12.048 Oxysterols receptor LXR-alpha 3
18973288 10.1021/jm800799q Mus musculus 3
19394832 10.1016/j.bmc.2009.04.012 Oxysterols receptor LXR-beta 3
18973288 10.1021/jm800799q Oxysterols receptor LXR-beta 3
18973288 10.1021/jm800799q Oxysterols receptor LXR-alpha 3
17034119 10.1021/jm0609566 Oxysterols receptor LXR-alpha 3
17034119 10.1021/jm0609566 Peroxisome proliferator-activated receptor delta 2
18023179 10.1016/j.bmcl.2007.11.013 THP-1 2
18023179 10.1016/j.bmcl.2007.11.013 J774 2
18023179 10.1016/j.bmcl.2007.11.013 HepG2 2

Data from ChEMBL 36 via Core Engine