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


Classification

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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Reactions graph legend

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
Pubmed ID: 20671299

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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