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
408.387441
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 an oxysterol.1 It is formed from cholesterol by cholesterol-25-hydroxylase, and its production can be induced by inflammation or infection.2 25-hydroxy Cholesterol suppresses endogenous cholesterol synthesis by binding to insulin-induced gene (INSIG) proteins and preventing sterol regulatory element binding proteins (SREBPs) from being transported to the Golgi. It inhibits IgA class switching induced by LPS and various cytokines in B cells (IC50 = ~50 nM).3 25-hydroxy Cholesterol inhibits replication of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in Vero cells (EC50 = 3.675 µM) and reduces increases in viral protein production in infected Vero cells when used prior to infection.4 It reduces viral RNA loads in the lung and trachea in a mouse model of SARS-CoV-2 infection when administered at a dose of 100 mg/kg per day. Serum levels of 25-hydroxy cholesterol are increased in patients with SARS-CoV-2.5

This information has been provided by Cayman Chemical

References

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

Admin

Created at
-
Updated at
29th Jan 2021