Structure Database (LMSD)

Common Name
Desmosterol(d6)
Systematic Name
cholest-5,24-dien-3β-ol(d6)
Synonyms
LM ID
LMST01010090
Formula
Exact Mass
Calculate m/z
390.376877
Status
Curated

Classification

Biological Context

24-dehydro Cholesterol-d6 is intended for use as an internal standard for the quantification of 24-dehydro cholesterol by GC- or LC-MS. 24-dehydro Cholesterol is an immediate precursor to cholesterol in the Bloch pathway of cholesterol biosynthesis. Structurally, it varies from cholesterol only by a single double bond at carbon 24 and has been used as cholesterol substitute in cellular membrane studies.1 During brain development, 24-dehydro cholesterol transiently accumulates, composing up to 30% of total brain sterol, where it is poised to rapidly enrich membrane sterols.2 However, defects in cholesterol synthesis can lead to a condition called desmosterolosis, which results in an accumulation of excess 24-dehydro cholesterol.3 24-dehydro Cholesterol has been reported to activate liver X receptor-target genes in both the liver of cholesterol-free mice and in cholesterol-starved macrophage foam cells in atherosclerotic lesions.4,5

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)
AVSXSVCZWQODGV-QSOBUISFSA-N
InChi (Click to copy)
InChI=1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h7,9,19,21-25,28H,6,8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1/i1D3,2D3
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])CC/C=C(/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