Structure Database (LMSD)

Common Name
24,25-epoxy-cholesterol
Systematic Name
24S,25-epoxy-cholest-5-en-3β-ol
Synonyms
  • 24S,25-epoxy-cholesterol
LM ID
LMST01010012
Formula
Exact Mass
Calculate m/z
400.33413
Sum Composition
Status
Curated

Classification

Biological Context

24(S),25-epoxy Cholesterol is an oxysterol and the most abundant oxysterol in mouse ventral midbrain.1 It activates liver X receptors (LXRs) in the developing ventral midbrain to induce stem cell differentiation into dopaminergic neurons. 24(S),25-epoxy Cholesterol inhibits IL-6 production and degranulation of bone marrow-derived murine mast cells that express LXRβ.2 It inhibits the conversion of desmosterol to cholesterol by 3β-hydroxysterol Δ24-reductase (DHCR24/Seladin-1) in CHO-7 and SRD-1 cells when used at a concentration of 2.5 μM.3

This information has been provided by Cayman Chemical

References

3. Broccoli, V., and Caiazzo, M. Nuclear receptors: Oxysterols detour to neurodevelopment. Nat. Chem. Biol. 9(2), 70-71 (2013).
2. Zerenturk, E.J., Kristiana, I., Gill, S., et al. The endogenous regulator 24(S),25-epoxycholesterol inhibits cholesterol synthesis at DHCR24 (Seladin-1). Biochim. Biophys. Acta 1821(9), 1269-1277 (2012).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Mus musculus (#10090)
Mammalia (#40674)
Subcellular organelle lipidomics in TLR-4-activated macrophages.,
J Lipid Res, 2010
Pubmed ID: 20574076

String Representations

InChiKey (Click to copy)
OSENKJZWYQXHBN-XVYZBDJZSA-N
InChi (Click to copy)
InChI=1S/C27H44O2/c1-17(6-11-24-25(2,3)29-24)21-9-10-22-20-8-7-18-16-19(28)12-14-26(18,4)23(20)13-15-27(21,22)5/h7,17,19-24,28H,6,8-16H2,1-5H3/t17-,19+,20+,21-,22+,23+,24+,26+,27-/m1/s1
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@@H]3O[C@@]3(C)C)CC[C@@]21[H])[H]

Other Databases

KEGG ID
CHEBI ID
LIPIDBANK ID
SST0209
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 29
Rings 5
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 428.80
Topological Polar Surface Area 32.76
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 7.38
Molar Refractivity 120.09

Admin

Created at
-
Updated at
-