Home Other Building Blocks (8S,9S,10R,13R,14S,17R)-17-((R)-4-((S)-3,3-Dimethyloxiran-2-yl)butan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

(8S,9S,10R,13R,14S,17R)-17-((R)-4-((S)-3,3-Dimethyloxiran-2-yl)butan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

CAS No.:
77058-74-3
Catalog Number:
AG00G2QO
Molecular Formula:
C27H44O2
Molecular Weight:
400.6371
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥95%
1 week
United States
$161
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Product Description
Catalog Number:
AG00G2QO
Chemical Name:
(8S,9S,10R,13R,14S,17R)-17-((R)-4-((S)-3,3-Dimethyloxiran-2-yl)butan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol
CAS Number:
77058-74-3
Molecular Formula:
C27H44O2
Molecular Weight:
400.6371
MDL Number:
MFCD03695562
IUPAC Name:
(3S,8S,9S,10R,13R,14S,17R)-17-[(2R)-4-[(2S)-3,3-dimethyloxiran-2-yl]butan-2-yl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol
InChI:
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
InChI Key:
OSENKJZWYQXHBN-XVYZBDJZSA-N
SMILES:
OC1CCC2(C(=CCC3C2CCC2(C3CCC2C(CCC2OC2(C)C)C)C)C1)C
Properties
Complexity:
680  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Defined Bond Stereocenter Count:
0
Exact Mass:
400.334g/mol
Formal Charge:
0
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
400.647g/mol
Monoisotopic Mass:
400.334g/mol
Rotatable Bond Count:
4  
Topological Polar Surface Area:
32.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.6  
Literature
Title Journal
Upregulation of hydroxysteroid sulfotransferase 2B1b promotes hepatic oval cell proliferation by modulating oxysterol-induced LXR activation in a mouse model of liver injury. Archives of toxicology 20170101
Brain endogenous liver X receptor ligands selectively promote midbrain neurogenesis. Nature chemical biology 20130201
The endogenous regulator 24(S),25-epoxycholesterol inhibits cholesterol synthesis at DHCR24 (Seladin-1). Biochimica et biophysica acta 20120901
Liver X receptors agonists impede hepatitis C virus infection in an Idol-dependent manner. Antiviral research 20120901
[Research progress of liver X receptor agonists]. Yao xue xue bao = Acta pharmaceutica Sinica 20120401
Mast cell death induced by 24(S),25-epoxycholesterol. Experimental cell research 20101115
Low-density lipoprotein and oxysterols suppress the transcription of CTP: Phosphoethanolamine cytidylyltransferase in vitro. Biochimica et biophysica acta 20100401
Enhanced steatosis by nuclear receptor ligands: a study in cultured human hepatocytes and hepatoma cells with a characterized nuclear receptor expression profile. Chemico-biological interactions 20100330
LXR-activating oxysterols induce the expression of inflammatory markers in endothelial cells through LXR-independent mechanisms. Atherosclerosis 20091101
Ligand, receptor, and cell type-dependent regulation of ABCA1 and ABCG1 mRNA in prostate cancer epithelial cells. Molecular cancer therapeutics 20090701
Oxysterols: Sources, cellular storage and metabolism, and new insights into their roles in cholesterol homeostasis. Molecular aspects of medicine 20090601
24(S),25-epoxycholesterol: a messenger for cholesterol homeostasis. The international journal of biochemistry & cell biology 20090401
Epoxycholesterol impairs cholesteryl ester hydrolysis in macrophage foam cells, resulting in decreased cholesterol efflux. Arteriosclerosis, thrombosis, and vascular biology 20080601
Ligand specificity and evolution of liver X receptors. The Journal of steroid biochemistry and molecular biology 20080501
Combination of virtual screening and high throughput gene profiling for identification of novel liver X receptor modulators. Journal of medicinal chemistry 20080410
Endogenous 24(S),25-epoxycholesterol fine-tunes acute control of cellular cholesterol homeostasis. The Journal of biological chemistry 20080111
[Synthesis of sterols oxygenated in the terminal fragment of their side chains]. Bioorganicheskaia khimiia 20080101
Primary human astrocytes produce 24(S),25-epoxycholesterol with implications for brain cholesterol homeostasis. Journal of neurochemistry 20071201
Regulation of CYP3A4 and CYP2B6 expression by liver X receptor agonists. Biochemical pharmacology 20071115
Studies on the cholesterol-free mouse: strong activation of LXR-regulated hepatic genes when replacing cholesterol with desmosterol. Arteriosclerosis, thrombosis, and vascular biology 20071001
9-cis-Retinoic acid (9cRA), a retinoid X receptor (RXR) ligand, exerts immunosuppressive effects on dendritic cells by RXR-dependent activation: inhibition of peroxisome proliferator-activated receptor gamma blocks some of the 9cRA activities, and precludes them to mature phenotype development. Journal of immunology (Baltimore, Md. : 1950) 20070515
Selective up-regulation of LXR-regulated genes ABCA1, ABCG1, and APOE in macrophages through increased endogenous synthesis of 24(S),25-epoxycholesterol. The Journal of biological chemistry 20070223
SREBP-2 positively regulates transcription of the cholesterol efflux gene, ABCA1, by generating oxysterol ligands for LXR. The Biochemical journal 20061215
Discovery and optimization of a novel series of liver X receptor-alpha agonists. Bioorganic & medicinal chemistry letters 20060315
[Synthesis of (24S)-hydroxy- and (24S)-24,25-epoxycholesterol analogues, potential agonists of nuclear LXR receptors]. Bioorganicheskaia khimiia 20060101
Adipocytic differentiation and liver x receptor pathways regulate the accumulation of triacylglycerols in human vascular smooth muscle cells. The Journal of biological chemistry 20050204
Statins inhibit synthesis of an oxysterol ligand for the liver x receptor in human macrophages with consequences for cholesterol flux. Arteriosclerosis, thrombosis, and vascular biology 20041201
24(S),25-epoxycholesterol--a potential friend. Arteriosclerosis, thrombosis, and vascular biology 20041201
Enhanced synthesis of the oxysterol 24(S),25-epoxycholesterol in macrophages by inhibitors of 2,3-oxidosqualene:lanosterol cyclase: a novel mechanism for the attenuation of foam cell formation. Circulation research 20031017
Induction of intestinal ATP-binding cassette transporters by a phytosterol-derived liver X receptor agonist. The Journal of biological chemistry 20030919
X-ray crystal structure of the liver X receptor beta ligand binding domain: regulation by a histidine-tryptophan switch. The Journal of biological chemistry 20030718
Identification of a nonsteroidal liver X receptor agonist through parallel array synthesis of tertiary amines. Journal of medicinal chemistry 20020509
Oxysterol stimulation of epidermal differentiation is mediated by liver X receptor-beta in murine epidermis. The Journal of investigative dermatology 20020101
Key regulatory oxysterols in liver: analysis as delta4-3-ketone derivatives by HPLC and response to physiological perturbations. Journal of lipid research 20010401
Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha. Journal of medicinal chemistry 20010315
Structural requirements of ligands for the oxysterol liver X receptors LXRalpha and LXRbeta. Proceedings of the National Academy of Sciences of the United States of America 19990105
Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway. The Journal of biological chemistry 19970207
Properties