LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

22R-hydroxycholesterol

Systematic Name

cholest-5-en-3β,22R-diol

Synonyms

LM ID

LMST01010086

Formula

C₂₇H₄₆O₂

Exact Mass

Calculate m/z

402.34978

Sum Composition

ST 27:1;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View NP-MRD ID(NMR) spectrum

Classification

Biological Context

22(R)-hydroxy Cholesterol is an endogenous agonist for LXRs that activates LXRα with an EC50 value of 325 nM.¹ 22(R)-hydroxy Cholesterol, acting through LXR heterodimerized with the retinoid X receptor, induces the expression of the ABCA1 reverse cholesterol transporter.² This activity increases the efflux of cholesterol from enterocytes and thus inhibits the overall absorption of cholesterol. 22(R)-hydroxy Cholesterol can be used as a substrate to monitor cholesterol transport or as an endogenous positive control for testing LXR agonists which have potential as therapeutic agents for the treatment of atherosclerosis.

This information has been provided by Cayman Chemical

References

1. Costet, P., Luo, Y., Wang, N., et al. Sterol-dependent transactivation of the ABC1 promoter by the liver X receptor/retinoid X receptor. J. Biol. Chem. 275(36), 28240-28245 (2000).

2. Spencer, T.A., Dansu, L., Russel, J.S., et al. Pharmacophore analysis of the nuclear oxysterol receptor LXRα. J. Med. Chem. 44(6), 886-897 (2001).

Reactions

Filter by species:

Click on an edge to display the reaction(s).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Mus musculus (#10090)

Mammalia (#40674)

Subcellular organelle lipidomics in TLR-4-activated macrophages.,
J Lipid Res, 2010

Pubmed ID: 20574076

DOI: 10.1194/jlr.M008748

String Representations

InChiKey (Click to copy)

RZPAXNJLEKLXNO-GFKLAVDKSA-N

InChi (Click to copy)

InChI=1S/C27H46O2/c1-17(2)6-11-25(29)18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20-,21-,22+,23-,24-,25+,26-,27+/m0/s1

SMILES (Click to copy)

C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)[C@H](O)CCC(C)C)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1