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
3D model of 24,25-epoxy-cholesterol
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
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
J Lipid Res, 2010
Pubmed ID:
20574076
DOI:
10.1194/jlr.M008748
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
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
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Updated at
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