Structure Database (LMSD)
Common Name
24S-hydroxy-cholesterol
Systematic Name
cholest-5-en-3β,24S-diol
Synonyms
LM ID
LMST01010019
Formula
Exact Mass
Calculate m/z
402.34978
Sum Composition
Status
Curated
3D model of 24S-hydroxy-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)-hydroxy Cholesterol is a side-chain substituted oxysterol that has important roles in cholesterol homeostasis. It is generated by the action of CYP46 on cholesterol in the brain and diffuses across the blood-brain barrier to the systemic circulation where it can modulate cell signaling, be used for further sterol biosynthesis, or be metabolized in the liver.1 24(S)-hydroxy cholesterol potently activates LXRα and LXRβ nuclear receptors (EC50 = 4 and 3 μM, respectively), causing upregulation of cholesterol-lowering genes.1,2,3 In the brain, this oxysterol controls cholesterol processing to facilitate neurological repair during Alzheimer’s disease and other neuropathological conditions.1
This information has been provided by Cayman Chemical
References
2. Geyeregger, R., Zeyda, M., and Stulnig, T.M. Liver X receptors in cardiovascular and metabolic disease. Cell. Mol. Life Sci. 63, 524-539 (2006).
Reactions
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References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
J Lipid Res, 2010
Pubmed ID:
20671299
DOI:
10.1194/jlr.M009449
String Representations
InChiKey (Click to copy)
IOWMKBFJCNLRTC-XWXSNNQWSA-N
InChi (Click to copy)
InChI=1S/C27H46O2/c1-17(2)25(29)11-6-18(3)22-9-10-23-21-8-7-19-16-20(28)12-14-26(19,4)24(21)13-15-27(22,23)5/h7,17-18,20-25,28-29H,6,8-16H2,1-5H3/t18-,20+,21+,22-,23+,24+,25+,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](O)C(C)C)CC[C@@]21[H])[H]
Other Databases
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
SST9004
PubChem CID
SwissLipids ID
Cayman ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
29
Rings
4
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
441.16
Topological Polar Surface Area
40.46
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
2
logP
6.93
Molar Refractivity
121.47
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Updated at
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