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Compound Detail

CHEMBL422904

22(R)-HYDROXYCHOLESTEROL
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CC(C)CC[C@@H](O)[C@@H](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 CHEMBL422904
Name 22(R)-HYDROXYCHOLESTEROL
Phase Preclinical
Structure Type MOL
InChI Key RZPAXNJLEKLXNO-GFKLAVDKSA-N
4
Targets
12
Activities
2
Assay Types
0
PK Parameters
20
Publications
0
Known Names

Molecular Properties

402.7
MW (Da)
6.36
ALogP
2
HBA
2
HBD
40.5
PSA (Ų)
0.53
QED
1
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Unknown
Chirality Unknown

Flags

Natural Product First in Class Prodrug

Extended Properties

Molecular Formula C27H46O2
MW 402.66
Aromatic Rings 0
Heavy Atoms 29
NP-Likeness 2.80

Activity Summary

EC50 11 meas. best 7.7
IC50 1 meas. best 4.0

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nuclear receptor ROR-gamma
CHEMBL1741186
 EC50 7.7 7.7 20.0 3
Oxysterols receptor LXR-alpha
CHEMBL2808
 EC50 6.49 5.68 325.0 5
Oxysterols receptor LXR-beta
CHEMBL4093
 EC50 5.82 5.32 1500.0 3
Unchecked
CHEMBL612545
 IC50 4.0 4.0 100000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nuclear receptor ROR-gamma EC50 = 20.0 nM 7.7 Agonist activity at human His6-tagged ROR gamma ligand binding domain (residues ... -
Nuclear receptor ROR-gamma EC50 = 20.0 nM 7.7 Displacement of [3H]25-hydroxycholesterol from human RORc-LBD expressed in bacte... 25453817
Nuclear receptor ROR-gamma EC50 = 20.0 nM 7.7 Agonist activity at 6xHis tagged human RORgammat LBD (262 to 507 residues) expre... 29412659
Oxysterols receptor LXR-alpha EC50 = 325.0 nM 6.49 Concentration required for half maximal activity was calculated in human nuclear... 11300870
Oxysterols receptor LXR-alpha EC50 = 1000.0 nM 6.0 Agonist activity at human LXRalpha-LBD assessed as recruitment of co-activator p... 23769638
Oxysterols receptor LXR-alpha EC50 = 1200.0 nM 5.92 Agonist activity at full length human LXRalpha transfected in HEK293T cells co-e... 37526502
Oxysterols receptor LXR-beta EC50 = 1500.0 nM 5.82 Agonist activity at full length human LXRbeta transfected in HEK293T cells co-ex... 37526502
Oxysterols receptor LXR-beta EC50 = 4750.0 nM 5.32 Activation of GAL4 fused human LXR beta expressed in HEK293 cells after 24 hrs b... 28741954
Oxysterols receptor LXR-alpha EC50 = 6710.0 nM 5.17 Activation of GAL4 fused human LXR alpha expressed in HEK293 cells after 24 hrs ... 28741954
Oxysterols receptor LXR-alpha EC50 = 15000.0 nM 4.82 Effective concentration for cofactor association with recombinant liver X recept... 15911262
Oxysterols receptor LXR-beta EC50 = 15000.0 nM 4.82 Effective concentration for cofactor association with recombinant liver X recept... 15911262
Unchecked IC50 = 100000.0 nM 4.0 Inhibition of Saccharomyces sp. alpha-glucosidase 18343126

Literature References

PubMed DOI Target Context # Activities
28741954 10.1021/acs.jmedchem.7b00091 Unchecked 10
15911262 10.1016/j.bmcl.2005.03.100 Oxysterols receptor LXR-alpha 4
15911262 10.1016/j.bmcl.2005.03.100 Oxysterols receptor LXR-beta 4
16124770 10.1021/np050182g Oxysterols receptor LXR-alpha 3
16124770 10.1021/np050182g Oxysterols receptor LXR-beta 3
37526502 10.1021/acs.jnatprod.3c00059 Oxysterols receptor LXR-alpha 2
11300870 10.1021/jm0004749 Oxysterols receptor LXR-alpha 2
37526502 10.1021/acs.jnatprod.3c00059 Oxysterols receptor LXR-beta 2
37526502 10.1021/acs.jnatprod.3c00059 Liver X receptor 2
24900386 10.1021/ml300192k Unchecked 2
18343126 10.1016/j.bmc.2008.02.078 Unchecked 2
23769638 10.1016/j.bmcl.2013.05.030 Oxysterols receptor LXR-alpha 1
23830695 10.1016/j.bmc.2013.06.022 Unchecked 1
- 10.1039/C3MD00005B Nuclear receptor ROR-gamma 1
25453817 10.1016/j.bmcl.2014.10.037 Nuclear receptor ROR-gamma 1
24928400 10.1016/j.bmcl.2014.05.064 NPC1-like intracellular cholesterol transporter 1 1
28741954 10.1021/acs.jmedchem.7b00091 Oxysterols receptor LXR-alpha 1
20695472 10.1021/np100120c Retinoic acid receptor RXR-alpha 1
28169169 10.1016/j.bmcl.2017.01.066 Oxysterols receptor LXR-alpha 1
29412659 10.1021/acs.jmedchem.7b01314 Nuclear receptor ROR-gamma 1

Data from ChEMBL 36 via Core Engine