Structure Database (LMSD)
Common Name
25-hydroxy-cholesterol(d6)
Systematic Name
cholest-5-en-3β,25-diol(d6)
Synonyms
3D model of 25-hydroxy-cholesterol(d6)
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
25-hydroxy Cholesterol-d6 is intended for use as an internal standard for the quantification of 25-hydroxy cholesterol by GC- or LC-MS. 25-hydroxy Cholesterol is a side-chain substituted oxysterol derived from dietary cholesterol that inhibits the cleavage of sterol regulatory element binding proteins (SREBPs) to suppress endogenous cholesterol synthesis in various cell types.1 It has been implicated in a variety of metabolic events including cholesterol homeostasis and atherosclerosis as well as antitumor activities as it has been shown to induce apoptosis through down-regulation of Bcl-2 expression and activation of caspases.2 Immunomodulating capabilities have also been observed as the oxysterol can act as a LXR-RXR ligand coupling cholesterol synthesis to T cell proliferation, can reduce (EC50 ~ 65 nM) IgA production by B cells in response to IL-2, and can suppress differentiation of monocytes into macrophages.3,4,5
This information has been provided by Cayman Chemical
References
2. Adams, C.M., Reitz, J., De Brabander, J.K., et al. Cholesterol and 25-hydroxycholesterol inhibit activation of SREBPs by different mechanisms, both involving SCAP and Insigs. The Journal of Biological Chemisty 279(50), 52772-52780 (2004).
3. McDonald, J.G., and Russell, D.W. Editorial: 25-Hydroxycholesterol: A new life in immunology. J. Leukoc. Biol. 88(6), 1071-1072 (2010).
References
Comments
Synthetic deuterated standard
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
synthetic construct
(#32630)
Synthetic deuterated standard
String Representations
InChiKey (Click to copy)
INBGSXNNRGWLJU-KHKDDIDZSA-N
InChi (Click to copy)
InChI=1S/C27H46O2/c1-18(7-6-14-25(2,3)29)22-10-11-23-21-9-8-19-17-20(28)12-15-26(19,4)24(21)13-16-27(22,23)5/h8,18,20-24,28-29H,6-7,9-17H2,1-5H3/t18-,20+,21+,22-,23+,24+,26+,27-/m1/s1/i2D3,3D3
SMILES (Click to copy)
[C@]12(CC=C3C[C@@H](O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@@]([H])([C@@](C)([H])CCCC(O)(C([2H])([2H])[2H])C([2H])([2H])[2H])CC[C@@]21[H])[H]
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Created at
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Updated at
29th Jan 2021