20S-Hydroxycholesterol
From Wikipedia, the free encyclopedia
| Names | |
|---|---|
| IUPAC name
Cholest-5-ene-3β,20-diol | |
| Systematic IUPAC name
(1S,3aS,3bS,7S,9aR,9bS,11aS)-1-[(2S)-2-Hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-2,3,3a,3b,4,6,7,8,9,9a,9b,10,11,11a-tetradecahydro-1H-cyclopenta[a]phenanthren-7-ol | |
| Other names
20α-Hydroxycholesterol; 5-Cholestene-3β,20α-diol; 20(S)-OHC | |
| Identifiers | |
3D model (JSmol) |
|
| ChEBI | |
| ChemSpider | |
PubChem CID |
|
| UNII | |
| |
| |
| Properties | |
| C27H46O2 | |
| Molar mass | 402.663g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25°C [77°F], 100kPa).
| |
Chemical compound
20S-Hydroxycholesterol is a steroid of the oxysterol class. It is a human metabolite of cholesterol.
20S-Hydroxycholesterol has been the subject of research into its role in human health. For example, 20S-hydroxycholesterol has been found to be an allosteric activator of the Hedgehog signaling pathway, which has implications in cancer research.[1] [2] [3] [4] [5]
More recently, 20S-hydroxycholesterol was identified as an endogenous ligand for the sigma-2 receptor, which had previously been considered an orphan receptor since its discovery in 1990.[6] [7]
References
[edit ]- ↑ Griffiths, William J.; Wang, Yuqin (2019). "Oxysterol research: A brief review". Biochemical Society Transactions. 47 (2): 517–526. doi:10.1042/BST20180135. PMC 6490702 . PMID 30936243.
- ↑ Kim, W. K.; Meliton, V.; Amantea, C. M.; Hahn, T. J.; Parhami, F. (2007). "20(S)-hydroxycholesterol inhibits PPARgamma expression and adipogenic differentiation of bone marrow stromal cells through a hedgehog-dependent mechanism". Journal of Bone and Mineral Research. 22 (11): 1711–1719. doi:10.1359/jbmr.070710 . PMID 17638575. S2CID 935824.
- ↑ Nachtergaele, S.; Mydock, L. K.; Krishnan, K.; Rammohan, J.; Schlesinger, P. H.; Covey, D. F.; Rohatgi, R. (2012). "Oxysterols are allosteric activators of the oncoprotein Smoothened". Nature Chemical Biology. 8 (2): 211–220. doi:10.1038/nchembio.765. PMC 3262054 . PMID 22231273.
- ↑ Dwyer, J. R.; Sever, N.; Carlson, M.; Nelson, S. F.; Beachy, P. A.; Parhami, F. (2007). "Oxysterols are novel activators of the hedgehog signaling pathway in pluripotent mesenchymal cells". The Journal of Biological Chemistry. 282 (12): 8959–8968. doi:10.1074/jbc.M611741200 . PMID 17200122.
- ↑ Nedelcu, D.; Liu, J.; Xu, Y.; Jao, C.; Salic, A. (2013). "Oxysterol binding to the extracellular domain of Smoothened in Hedgehog signaling". Nature Chemical Biology. 9 (9): 557–564. doi:10.1038/nchembio.1290. PMC 3749252 . PMID 23831757.
- ↑ Derek Lowe (November 22, 2021). "Another Orphan Reunited". In The Pipeline. Science.
- ↑ Cheng, Yu-Shiuan; Zhang, Tianyi; Ma, Xiang; Pratuangtham, Sarida; Zhang, Grace C.; Ondrus, Alexander A.; Mafi, Amirhossein; Lomenick, Brett; Jones, Jeffrey J.; Ondrus, Alison E. (2021). "A proteome-wide map of 20(S)-hydroxycholesterol interactors in cell membranes". Nature Chemical Biology. 17 (12): 1271–1280. doi:10.1038/s41589-021-00907-2. ISSN 1552-4450. PMC 8607797 . PMID 34799735.