Structure Database (LMSD)

Common Name
22S-hydroxycholesterol
Systematic Name
cholest-5-en-3β,22S-diol
Synonyms
LM ID
LMST01010345
Formula
Exact Mass
Calculate m/z
402.34978
Sum Composition
Status
Curated

Classification

Biological Context

22(S)-hydroxy Cholesterol is a synthetic oxysterol and a modulator of the liver X receptor (LXR).1 It prevents monocyte chemoattractant protein 1 (MCP-1) expression induced by the LXR agonist GW 3965 in primary hepatocytes and downregulates mRNA expression of the LXR target genes CD36, ACSL1, and SCD-1 in human myotubes.2 It decreases triacylglycerol and diacylglycerol synthesis from labeled palmitate and acetate, respectively, in human myoblasts by 50% when used at a concentration of 10 µM.1 22(S)-hydroxy Cholesterol also reduces fatty acid synthase (FASN) reporter activity through an LXR response element in the promoter region in COS-1 cells transfected with RXRα and LXRα and decreases the expression of MCP-1 and CCR2 in a mouse model of chronic ethanol consumption.1,2 Dietary supplementation of 22(S)-hydroxy cholesterol (30 mg/kg per day) leads to less body weight gain and lower liver triacylglycerol levels in rats when fed either a regular chow or high-fat diet as well as prevents an increase in plasma triacylglycerol levels resulting from a high-fat diet.3

This information has been provided by Cayman Chemical

References

1. Kase, E.T., Andersen, B., Nebb, H.I., et al. 22-Hydroxycholesterols regulate lipid metabolism differently than T0901317 in human myotubes. Biochim. Biophys. Acta 1761(12), 1515-1522 (2006).

String Representations

InChiKey (Click to copy)
RZPAXNJLEKLXNO-QUOSNDFLSA-N
InChi (Click to copy)
InChI=1S/C27H46O2/c1-17(2)6-11-25(29)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+/m0/s1
SMILES (Click to copy)
C1[C@]2(C)[C@@]3([H])CC[C@]4(C)[C@@]([H])([C@]([H])(C)[C@@H](O)CCC(C)C)CC[C@@]4([H])[C@]3([H])CC=C2C[C@@H](O)C1

Other Databases

CHEBI ID
PubChem CID
Cayman 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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