(22R)-hydroxycholesterol





Description


(22R)-hydroxycholesterol is a naturally occurring sterol that is produced in the body from cholesterol through the action of the enzyme cholesterol 22-hydroxylase. It is primarily synthesized in the brain and is involved in the regulation of cholesterol metabolism, as well as in the synthesis of steroid hormones. (22R)-hydroxycholesterol has been shown to have a number of biological activities, including anti-inflammatory and neuroprotective effects. It is thought to play a role in the regulation of immune function, and has been shown to inhibit the production of pro-inflammatory cytokines in vitro. In addition to its biological activity, (22R)-hydroxycholesterol has been identified as a biomarker for a number of diseases, including Alzheimer's disease and multiple sclerosis. It has been suggested that measuring levels of (22R)-hydroxycholesterol in the blood or cerebrospinal fluid may be a useful diagnostic tool for these conditions. Overall, (22R)-hydroxycholesterol is an important molecule in the body with a range of biological activities and potential clinical applications.


Chemical Formula:
C27H46O2
Molecular Weight:
402.659 Daltons
Monoisotopic Mass:
402.34978072079997 Daltons
SMILES:
CC(C)CCC(O)C(C)[CH]3(CC[CH]4([CH]2(CC=C1(CC(O)CCC(C)1[CH]2CCC(C)34))))
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

Synonyms
  • (22R)-OH-cholesterol

Databases
MetaCyc:  CPD-14702
PubChem (CID):  167685
HMDB:  HMDB04035
LIPID MAPS:  LMST01010086
KEGG:  C05502
ChEBI:  67237
Reactome:  193019
MetaNetX:  MNXM90173