Chemistry:20S-Hydroxycholesterol
From HandWiki
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| IUPAC name
(3S,8S,9S,10R,13S,14S,17S)-17-[(2S)-2-Hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
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| Other names
20α-Hydroxycholesterol; 5-Cholestene-3β,20α-diol; 20(S)-OHC
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| Identifiers | |
3D model (JSmol)
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PubChem CID
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| Properties | |
| C27H46O2 | |
| Molar mass | 402.663 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). | |
| Infobox references | |
Tracking categories (test):
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
- ↑ Griffiths, William J.; Wang, Yuqin (2019). "Oxysterol research: A brief review". Biochemical Society Transactions 47 (2): 517–526. doi:10.1042/BST20180135. 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.
- ↑ 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. 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. PMID 23831757.
- ↑ Derek Lowe (November 22, 2021). "Another Orphan Reunited". In The Pipeline. Science. https://www.science.org/content/blog-post/another-orphan-reunited.
- ↑ Cheng, Yu-Shiuan; Zhang, Tianyi; Ma, Xiang; Pratuangtham, Sarida; Zhang, Grace C.; Ondrus, Alexander A.; Mafi, Amirhossein; Lomenick, Brett et al. (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. PMID 34799735.
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