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Compound Detail

CHEMBL434302

24(S),25-EPOXYCHOLESTEROL
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C[C@H](CC[C@@H]1OC1(C)C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL434302
Name 24(S),25-EPOXYCHOLESTEROL
Phase Preclinical
Structure Type MOL
InChI Key OSENKJZWYQXHBN-XVYZBDJZSA-N
2
Targets
9
Activities
1
Assay Types
0
PK Parameters
8
Publications
0
Known Names

Molecular Properties

400.6
MW (Da)
6.52
ALogP
2
HBA
1
HBD
32.8
PSA (Ų)
0.43
QED
1
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C27H44O2
MW 400.65
Aromatic Rings 0
Heavy Atoms 29
NP-Likeness 2.96

Activity Summary

EC50 9 meas. best 7.02

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Oxysterols receptor LXR-alpha
CHEMBL2808
 EC50 7.02 6.4433 95.0 6
Oxysterols receptor LXR-beta
CHEMBL4093
 EC50 6.78 6.5733 168.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Oxysterols receptor LXR-alpha EC50 = 95.0 nM 7.02 Ligand-dependent recruitment of steroid receptor co-activator 1 (SRC1) to Liver ... 11985463
Oxysterols receptor LXR-alpha EC50 = 117.0 nM 6.93 Agonist activity at human LXRalpha coexpressed in African green monkey CV1 cells... 26990539
Oxysterols receptor LXR-beta EC50 = 168.0 nM 6.78 Agonist activity at human LXRbeta coexpressed in African green monkey CV1 cells ... 26990539
Oxysterols receptor LXR-alpha EC50 = 280.0 nM 6.55 Agonist activity at LXRalpha ligand binding domain by FRET based SRC1 recruitmen... 19264481
Oxysterols receptor LXR-beta EC50 = 286.0 nM 6.54 Agonist activity at LXRbeta ligand binding domain by FRET based SRC1 recruitment... 19264481
Oxysterols receptor LXR-beta EC50 = 400.0 nM 6.4 Agonist activity at human LXRbeta expressed in human SH-SY5Y cells co-transfecte... 19264481
Oxysterols receptor LXR-alpha EC50 = 460.0 nM 6.34 Concentration required for half maximal activity was calculated in human nuclear... 11300870
Oxysterols receptor LXR-alpha EC50 = 500.0 nM 6.3 Activity against LXR alpha transiently transfected in HEK293 cells 16386417
Oxysterols receptor LXR-alpha EC50 = 3000.0 nM 5.52 Effective concentration in LXR alpha-Gal4 receptor gene assay 11985463

Literature References

PubMed DOI Target Context # Activities
18324758 10.1021/jm7011326 THP-1 14
11985463 10.1021/jm0255116 Oxysterols receptor LXR-alpha 4
11300870 10.1021/jm0004749 Oxysterols receptor LXR-alpha 2
16386417 10.1016/j.bmcl.2005.12.015 Oxysterols receptor LXR-alpha 2
19264481 10.1016/j.bmcl.2009.02.039 Oxysterols receptor LXR-beta 2
19264481 10.1016/j.bmcl.2009.02.039 Oxysterols receptor LXR-alpha 2
26990539 10.1021/acs.jmedchem.5b02029 Oxysterols receptor LXR-alpha 2
26990539 10.1021/acs.jmedchem.5b02029 Oxysterols receptor LXR-beta 2

Data from ChEMBL 36 via Core Engine