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22 (S) -hydroxy Cholesterol

CAT: 0013-GTR19277393-01Size: 1 mgDry Ice: NoHazardous: No
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Description
22 (S) -hydroxy Cholesterol is a synthetic oxysterol and a modulator of the liver X receptor (LXR) .t 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. It decreases triacylglycerol and diacylglycerol synthesis from labeled palmitate and acetate, respectively, in human myoblasts by 50% when used at a concentration of 10 uM. 22 (S) -hydroxy Cholesterol also reduces fatty acid synthase (FAS) 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.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.
CAS Number
22348-64-7
Smiles
C[C@@]12[C@] ([C@]3 ([C@@] ([C@]4 (C) C (=CC3) C[C@@H] (O) CC4) (CC1) [H]) [H]) (CC[C@@]2 ([C@@H] ([C@H] (CCC (C) C) O) C) [H]) [H]
Molecular Formula
C27H46O2
Molecular Weight
402.65
Storage Conditions
-20°C
Notes
For research use only.

Chemical Information

22S-hydroxycholesterol

(22S)-22-hydroxycholesterol is an oxysterol that is the 22S-hydroxy derivative of cholesterol. It is a 3beta-hydroxy-Delta(5)-steroid, a 22-hydroxy steroid and an oxysterol. It is functionally related to a cholesterol.

CAS Number22348-64-7
PubChem CID168038
IUPAC Name(3S,8S,9S,10R,13S,14S,17R)-17-[(2S,3S)-3-hydroxy-6-methylheptan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
Molecular FormulaC27H46O2
Molecular Weight402.7
XLogP7
Topological Polar Surface Area40.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Heavy Atom Count29
Formal Charge0
Complexity624
SMILES
C[C@@H]([C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C)[C@H](CCC(C)C)O
InChI
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
InChIKey
RZPAXNJLEKLXNO-QUOSNDFLSA-N
Chemical Structure
2D Structure
2D structure of 22S-hydroxycholesterol
CAS: 22348-64-7
CID: 168038
Formula: C27H46O2
MW: 402.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight402.7
XLogP37
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass402.349780706
Monoisotopic Mass402.349780706
Topological Polar Surface Area40.5 Ų
Heavy Atom Count29
Formal Charge0
Complexity624
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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