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Compound Detail

CHEMBL595689

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Cc1cnc2c(C(F)(F)F)cccc2c1-c1cccc(Oc2cccc(S(C)(=O)=O)c2)c1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL595689
Phase Preclinical
Structure Type MOL
InChI Key ZDUOYBOFMKORCT-UHFFFAOYSA-N
6
Targets
16
Activities
2
Assay Types
12
PK Parameters
20
Publications
0
Known Names

Molecular Properties

457.5
MW (Da)
6.42
ALogP
4
HBA
0
HBD
56.3
PSA (Ų)
0.35
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

First in Class Prodrug

Extended Properties

Molecular Formula C24H18F3NO3S
MW 457.47
Aromatic Rings 4
Heavy Atoms 32
NP-Likeness -1.09

Activity Summary

EC50 8 meas. best 8.22
IC50 8 meas. best 9.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Oxysterols receptor LXR-alpha
CHEMBL2808
 IC50 9.0 8.925 1.0 4
Oxysterols receptor LXR-beta
CHEMBL4093
 IC50 9.0 8.715 1.0 4
J774.A1
CHEMBL614040
 EC50 8.22 8.22 6.0 1
THP-1
CHEMBL614245
 EC50 8.0 8.0 10.0 2
Oxysterols receptor LXR-alpha
CHEMBL2808
 EC50 7.51 7.51 31.0 1
Liver X receptor
CHEMBL3706564
 EC50 7.51 7.51 31.0 1
HepG2
CHEMBL395
 EC50 6.83 6.83 147.0 2
Oxysterols receptor LXR-beta
CHEMBL4093
 EC50 6.74 6.74 183.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 1690.0 ng.hr.mL-1 Mus musculus
Cmax 998.97 nM Mus musculus
T1/2 0.5 hr Mus musculus
T1/2 0.5 hr Rattus norvegicus
T1/2 0.5 hr Homo sapiens
T1/2 0.5 hr Rattus norvegicus
T1/2 0.5 hr Homo sapiens
T1/2 0.5 hr Mus musculus
T1/2 0.5 hr Rattus norvegicus
T1/2 0.5 hr Homo sapiens
t1/2 - - Mus musculus
Tmax 2.0 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Oxysterols receptor LXR-alpha IC50 = 1.0 nM 9.0 Displacement of [3H]T0901317 from human recombinant LXRalpha LBD 20006495
Oxysterols receptor LXR-beta IC50 = 1.0 nM 9.0 Displacement of [3H]TO901317 from human recombinant LXRbeta expressed in Escheri... 19962892
Oxysterols receptor LXR-alpha IC50 = 1.0 nM 9.0 Displacement of [3H]T0901317 from human recombinant LXRalpha-LBD 19932617
Oxysterols receptor LXR-alpha IC50 = 1.0 nM 9.0 Displacement of [3H]T0901317 from human recombinant LXRalpha LBD 20005711
Oxysterols receptor LXR-alpha IC50 = 2.0 nM 8.7 Displacement of [3H]TO901317 from human recombinant LXRalpha expressed in Escher... 19962892
Oxysterols receptor LXR-beta IC50 = 2.4 nM 8.62 Displacement of [3H]T0901317 from human recombinant LXRbeta LBD 20006495
Oxysterols receptor LXR-beta IC50 = 2.4 nM 8.62 Displacement of [3H]T0901317 from human recombinant LXRbeta-LBD 19932617
Oxysterols receptor LXR-beta IC50 = 2.4 nM 8.62 Displacement of [3H]T0901317 from human recombinant LXRbeta LBD 20005711
J774.A1 EC50 = 6.0 nM 8.22 Induction of ABCA1 mRNA expression in mouse J774A1 cells 19932617
THP-1 EC50 = 10.0 nM 8.0 Induction of ABCA1 mRNA upregulation in human THP1 cells 20006495
THP-1 EC50 = 10.0 nM 8.0 Induction of ABCA1 mRNA upregulation in human THP1 cells 20005711
Liver X receptor EC50 = 31.0 nM 7.51 Agonist activity at human recombinant LXR-LBD by Gal4beta transactivation assay 19932617
Oxysterols receptor LXR-alpha EC50 = 31.0 nM 7.51 Agonist activity at human Gal4-LBD fused LXRalpha LBD expressed in Huh7 cells by... 20005711
HepG2 EC50 = 147.0 nM 6.83 Increase in cellular triglyceride level in human HepG2 cells 20006495
HepG2 EC50 = 147.0 nM 6.83 Increase in cellular triglyceride level in human HepG2 cells 20005711
Oxysterols receptor LXR-beta EC50 = 183.0 nM 6.74 Agonist activity at human Gal4-LBD fused LXRbeta LBD expressed in Huh7 cells by ... 20005711

Literature References

PubMed DOI Target Context # Activities
20005711 10.1016/j.bmcl.2009.11.098 Mus musculus 4
20005711 10.1016/j.bmcl.2009.11.098 Oxysterols receptor LXR-beta 3
20005711 10.1016/j.bmcl.2009.11.098 Oxysterols receptor LXR-alpha 3
19932617 10.1016/j.bmcl.2009.10.132 Liver microsomes 2
20005711 10.1016/j.bmcl.2009.11.098 Liver microsomes 2
20005711 10.1016/j.bmcl.2009.11.098 HepG2 2
20005711 10.1016/j.bmcl.2009.11.098 THP-1 2
19932617 10.1016/j.bmcl.2009.10.132 Liver X receptor 2
19932617 10.1016/j.bmcl.2009.10.132 J774.A1 2
20006495 10.1016/j.bmcl.2009.11.099 Liver microsomes 2
20006495 10.1016/j.bmcl.2009.11.099 HepG2 2
20006495 10.1016/j.bmcl.2009.11.099 THP-1 2
19962892 10.1016/j.bmcl.2009.11.062 Oxysterols receptor LXR-beta 1
20006495 10.1016/j.bmcl.2009.11.099 Oxysterols receptor LXR-alpha 1
19962892 10.1016/j.bmcl.2009.11.062 Oxysterols receptor LXR-alpha 1
19962892 10.1016/j.bmcl.2009.11.062 Liver X receptor (LXR alpha AND LXR beta) 1
19932617 10.1016/j.bmcl.2009.10.132 Oxysterols receptor LXR-beta 1
20005711 10.1016/j.bmcl.2009.11.098 No relevant target 1
20006495 10.1016/j.bmcl.2009.11.099 ADMET 1
20006495 10.1016/j.bmcl.2009.11.099 Liver X receptor (LXR alpha AND LXR beta) 1

Data from ChEMBL 36 via Core Engine