Structure Database (LMSD)

Common Name
25-hydroxy-cholesterol(d6)
Systematic Name
cholest-5-en-3β,25-diol(d6)
Synonyms
LM ID
LMST01010146
Formula
Exact Mass
Calculate m/z
408.387442
Status
Curated

Classification

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]

Other Databases

KEGG ID
HMDB ID
PubChem CID
Cayman ID
Avanti ID

Admin

Created at
-
Updated at
29th Jan 2021