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2140-46-7,MFCD00057815
Catalog No.:AA0037SC

2140-46-7 | (8S,9S,10R,13R,14S,17R)-17-((R)-6-Hydroxy-6-methylheptan-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

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1mg
98%
in stock  
$16.00   $11.00
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5mg
98%
in stock  
$32.00   $22.00
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10mg
98%
in stock  
$62.00   $43.00
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25mg
98%
in stock  
$120.00   $84.00
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100mg
98%
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$220.00   $154.00
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA0037SC
Chemical Name:
(8S,9S,10R,13R,14S,17R)-17-((R)-6-Hydroxy-6-methylheptan-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:
2140-46-7
Molecular Formula:
C27H46O2
Molecular Weight:
402.6529
MDL Number:
MFCD00057815
SMILES:
O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC[C@@H]2[C@@H](CCCC(O)(C)C)C)C)C1)C
Properties
Computed Properties
 
Complexity:
636  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
8  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
XLogP3:
6.8  

Downstream Synthesis Route

[1]JournaloftheAmericanChemicalSociety,1950,vol.72,p.4248

[1]JournaloftheAmericanChemicalSociety,1950,vol.72,p.4247

[1]CollectionofCzechoslovakChemicalCommunications,2007,vol.72,p.1319-1330

[2]BioorganicandMedicinalChemistryLetters,2014,vol.24,p.3480-3485

[3]JournalofOrganicChemistry,1957,vol.22,p.1380,1383

[1]JournaloftheChemicalSociety.PerkintransactionsI,1972,vol.19,p.2423-2425

[1]TetrahedronLetters,1997,vol.38,p.7067-7070

[2]JournalofOrganicChemistry,1988,vol.53,p.3891-3893

[3]JournalofOrganicChemistry,1970,vol.35,p.2627-2632

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Title: 7beta-Hydroxycholesterol and 25-hydroxycholesterol-induced interleukin-8 secretion involves a calcium-dependent activation of c-fos via the ERK1/2 signaling pathway in THP-1 cells: oxysterols-induced IL-8 secretion is calcium-dependent.

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Journal: The Journal of biological chemistry 20090116

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Title: Effect of oxysterol-induced apoptosis of vascular smooth muscle cells on experimental hypercholesterolemia.

Journal: Journal of biomedicine & biotechnology 20090101

Title: Cross-talk between oxysterols and glucocorticoids: differential regulation of secreted phopholipase A2 and impact on oligodendrocyte death.

Journal: PloS one 20090101

Title: Cholesterol homeostasis in two commonly used human prostate cancer cell-lines, LNCaP and PC-3.

Journal: PloS one 20090101

Title: 25-Hydroxycholesterol-3-sulfate regulates macrophage lipid metabolism via the LXR/SREBP-1 signaling pathway.

Journal: American journal of physiology. Endocrinology and metabolism 20081201

Title: Primary hepatocytes as targets for hepatitis C virus replication.

Journal: Journal of viral hepatitis 20081201

Title: Role of oxidative stress in adaptive responses in special reference to atherogenesis.

Journal: Journal of clinical biochemistry and nutrition 20081101

Title: Liquid chromatography-tandem mass spectrometry determination of plasma 24S-hydroxycholesterol with chromatographic separation of 25-hydroxycholesterol.

Journal: Analytical biochemistry 20081001

Title: CETP polymorphisms influence cholesterol metabolism but not Alzheimer's disease risk.

Journal: Brain research 20080926

Title: SREBP activity is regulated by mTORC1 and contributes to Akt-dependent cell growth.

Journal: Cell metabolism 20080903

Title: Activation of a caspase-3-independent mode of cell death associated with lysosomal destabilization in cultured human retinal pigment epithelial cells (ARPE-19) exposed to 7beta-hydroxycholesterol.

Journal: Current eye research 20080901

Title: Cadmium chloride-induced disruption of testicular steroidogenesis in rainbow trout, Oncorhynchus mykiss.

Journal: Archives of environmental contamination and toxicology 20080701

Title: OSBP negatively regulates ABCA1 protein stability.

Journal: The Journal of biological chemistry 20080627

Title: 25-hydroxycholesterol induces mitochondria-dependent apoptosis via activation of glycogen synthase kinase-3beta in PC12 cells.

Journal: Free radical research 20080601

Title: Cholesterol supply and SREBPs modulate transcription of the Niemann-Pick C-1 gene in steroidogenic tissues.

Journal: Journal of lipid research 20080501

Title: Ligand specificity and evolution of liver X receptors.

Journal: The Journal of steroid biochemistry and molecular biology 20080501

Title: The N terminus controls sterol binding while the C terminus regulates the scaffolding function of OSBP.

Journal: The Journal of biological chemistry 20080321

Title: Effectors of rapid homeostatic responses of endoplasmic reticulum cholesterol and 3-hydroxy-3-methylglutaryl-CoA reductase.

Journal: The Journal of biological chemistry 20080118

Title: Purified NPC1 protein. I. Binding of cholesterol and oxysterols to a 1278-amino acid membrane protein.

Journal: The Journal of biological chemistry 20080111

Title: OSBP-related protein 8 (ORP8) suppresses ABCA1 expression and cholesterol efflux from macrophages.

Journal: The Journal of biological chemistry 20080104

Title: Oxysterol-binding protein-1 (OSBP1) modulates processing and trafficking of the amyloid precursor protein.

Journal: Molecular neurodegeneration 20080101

Title: [Effects of (22S,23S)- and (22R,23R)-3beta-hydroxy-22,23-oxido-5alpha-ergost-8(14)-en-15-ones on cholesteryl esters biosynthesis and acyl-CoA:cholesterol acyl transferase activity in Hep G2 cells].

Journal: Biomeditsinskaia khimiia 20080101

Title: Different kinetics of cholesterol delivery to components of the cholesterol homeostatic machinery: implications for cholesterol trafficking to the endoplasmic reticulum.

Journal: Biochimica et biophysica acta 20080101

Title: Taurine reduces the secretion of apolipoprotein B100 and lipids in HepG2 cells.

Journal: Lipids in health and disease 20080101

Title: Liver x receptor: a novel therapeutic target.

Journal: Indian journal of pharmaceutical sciences 20080101

Title: Liver X Receptor Agonists Inhibit the Phospholipid Regulatory Gene CTP: Phosphoethanolamine Cytidylyltransferase-Pcyt2.

Journal: Research letters in biochemistry 20080101

Title: Biosynthesis of the regulatory oxysterol, 5-cholesten-3beta,25-diol 3-sulfate, in hepatocytes.

Journal: Journal of lipid research 20071201

Title: Delta5 desaturase mRNA levels are increased by simvastatin via SREBP-1 at early stages, not via PPARalpha, in THP-1 cells.

Journal: European journal of pharmacology 20071001

Title: 27-Hydroxycholesterol is an endogenous SERM that inhibits the cardiovascular effects of estrogen.

Journal: Nature medicine 20071001

Title: Sulfated oxysterol, 25HC3S, is a potent regulator of lipid metabolism in human hepatocytes.

Journal: Biochemical and biophysical research communications 20070907

Title: Ribonucleic acid binding protein-mediated regulation of luteinizing hormone receptor expression in granulosa cells: relationship to sterol metabolism.

Journal: Molecular endocrinology (Baltimore, Md.) 20070901

Title: Amplification of the gene for SCAP, coupled with Insig-1 deficiency, confers sterol resistance in mutant Chinese hamster ovary cells.

Journal: Journal of lipid research 20070901

Title: The mammalian oxysterol-binding protein-related proteins (ORPs) bind 25-hydroxycholesterol in an evolutionarily conserved pocket.

Journal: The Biochemical journal 20070801

Title: Sterol regulatory element-binding protein-2- and liver X receptor-driven dual promoter regulation of hepatic ABC transporter A1 gene expression: mechanism underlying the unique response to cellular cholesterol status.

Journal: The Journal of biological chemistry 20070720

Title: SREBP-1 regulates the expression of heme oxygenase 1 and the phosphatidylinositol-3 kinase regulatory subunit p55 gamma.

Journal: Journal of lipid research 20070701

Title: Cholesterol oxidation is increased and PUFA decreased by frozen storage and grilling of Atlantic hake fillets (Merluccius hubbsi).

Journal: Lipids 20070701

Title: Cytotoxic oxysterols induce caspase-independent myelin figure formation and caspase-dependent polar lipid accumulation.

Journal: Histochemistry and cell biology 20070601

Title: Characterization of the sterol-binding domain of oxysterol-binding protein (OSBP)-related protein 4 reveals a novel role in vimentin organization.

Journal: Experimental cell research 20070415

Title: Prevention of 7-ketocholesterol-induced mitochondrial damage and cell death by calmodulin inhibition.

Journal: Brain research 20070316

Title: The low-density lipoprotein receptor plays a role in the infection of primary human hepatocytes by hepatitis C virus.

Journal: Journal of hepatology 20070301

Title: 25-Hydroxycholesterol, 7beta-hydroxycholesterol and 7-ketocholesterol upregulate interleukin-8 expression independently of Toll-like receptor 1, 2, 4 or 6 signalling in human macrophages.

Journal: Free radical research 20070301

Title: Oxysterols induced inflammation and oxidation in primary porcine retinal pigment epithelial cells.

Journal: Current eye research 20070301

Title: Regulation of human cytochrome P450 4F2 expression by sterol regulatory element-binding protein and lovastatin.

Journal: The Journal of biological chemistry 20070223

Title: Up-regulation of skeletal muscle LIM protein 1 gene by 25-hydroxycholesterol may mediate morphological changes of rat aortic smooth muscle cells.

Journal: Life sciences 20070109

Title: Cholesterol oxides as biomarkers of oxidative stress in type 1 and type 2 diabetes mellitus.

Journal: Diabetes/metabolism research and reviews 20070101

Title: Modulation of human Niemann-Pick C1-like 1 gene expression by sterol: Role of sterol regulatory element binding protein 2.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20070101

Title: Biosynthetic capacity of rainbow trout (Oncorhynchus mykiss) interrenal tissue after cadmium exposure.

Journal: Archives of environmental contamination and toxicology 20070101

Title: Evidence for the functional role of residues in the B'-C loop of baboon cytochrome P450 side-chain cleavage (CYP11A1) obtained by site-directed mutagenesis, kinetic analysis and homology modelling.

Journal: The Journal of steroid biochemistry and molecular biology 20070101

Title: Enzymatic reduction of oxysterols impairs LXR signaling in cultured cells and the livers of mice.

Journal: Cell metabolism 20070101

Title: Synthesis of the oxysterol, 24(S), 25-epoxycholesterol, parallels cholesterol production and may protect against cellular accumulation of newly-synthesized cholesterol.

Journal: Lipids in health and disease 20070101

Title: Leptin stimulates endogenous cholesterol synthesis in human monocytes: New role of an old player in atherosclerotic plaque formation. Leptin-induced increase in cholesterol synthesis.

Journal: The international journal of biochemistry & cell biology 20070101

Title: The immune response is involved in atherosclerotic plaque calcification: could the RANKL/RANK/OPG system be a marker of plaque instability?

Journal: Clinical & developmental immunology 20070101

Title: A Chinese hamster ovarian cell line imports cholesterol by high density lipoprotein degradation.

Journal: The Journal of biological chemistry 20061215

Title: Low cell cholesterol levels increase NFkappaB activity through a p38 MAPK-dependent mechanism.

Journal: Cellular signalling 20061201

Title: Effects of crude adlay hull acetone extract on corticosterone release from rat zona fasciculata-reticularis cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20061101

Title: Induction of apoptosis by 25-hydroxycholesterol in adult rat Leydig cells: protective effect of 17beta-estradiol.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20061101

Title: [Synthesis and structure-activity relationships of bioactive compounds using sterols].

Journal: Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan 20061101

Title: Neuropeptides induced a pronounced and statin-sensitive dysregulation of mevalonate cycle in human monocytes of patients with hypercholesterolemia.

Journal: Neuropeptides 20061001

Title: Oxysterol mixtures, in atheroma-relevant proportions, display synergistic and proapoptotic effects.

Journal: Free radical biology & medicine 20060915

Title: ABCA1 mediates high-affinity uptake of 25-hydroxycholesterol by membrane vesicles and rapid efflux of oxysterol by intact cells.

Journal: American journal of physiology. Cell physiology 20060901

Title: Bleomycin is a potent small-molecule inhibitor of hepatitis C virus replication.

Journal: Chembiochem : a European journal of chemical biology 20060901

Title: 25-Hydroxycholesterol has a dual effect on the proliferation of cultured rat astrocytes.

Journal: Neuropharmacology 20060801

Title: RhoA and p38 MAPK mediate apoptosis induced by cellular cholesterol depletion.

Journal: Apoptosis : an international journal on programmed cell death 20060701

Title: Sterol dependent regulation of human TM7SF2 gene expression: role of the encoded 3beta-hydroxysterol Delta14-reductase in human cholesterol biosynthesis.

Journal: Biochimica et biophysica acta 20060701

Title: Seasonal variation in calcitropic hormones and bone accrual in puberty.

Journal: The British journal of nutrition 20060701

Title: Regulation of cholesterol 25-hydroxylase expression by vitamin D3 metabolites in human prostate stromal cells.

Journal: Biochemical and biophysical research communications 20060630

Title: Formation of cholesterol oxidation products in marinated foods during heating.

Journal: Journal of agricultural and food chemistry 20060628

Title: Synthesis of ent-25-hydroxycholesterol.

Journal: Steroids 20060601

Title: Localization of StarD5 cholesterol binding protein.

Journal: Journal of lipid research 20060601

Title: HPLC method for quantification and characterization of cholesterol and its oxidation products in eggs.

Journal: Lipids 20060601

Title: A critical role for the histidine residues in the catalytic function of acyl-CoA:cholesterol acyltransferase catalysis: evidence for catalytic difference between ACAT1 and ACAT2.

Journal: FEBS letters 20060515

Title: Phase behavior of lipid monolayers containing DPPC and cholesterol analogs.

Journal: Biophysical journal 20060501

Title: Identification of a novel sulfonated oxysterol, 5-cholesten-3beta,25-diol 3-sulfonate, in hepatocyte nuclei and mitochondria.

Journal: Journal of lipid research 20060501

Title: Multiplexed flow cytometric analyses of pro- and anti-inflammatory cytokines in the culture media of oxysterol-treated human monocytic cells and in the sera of atherosclerotic patients.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Cloning and characterization of a cDNA encoding cholesterol side-chain cleavage cytochrome P450 (CYP11A1): tissue-distribution and changes in the transcript abundance in ovarian tissue of Japanese eel, Anguilla japonica, during artificially induced sexual development.

Journal: The Journal of steroid biochemistry and molecular biology 20060501

Title: Cholesterol, LDL, and 25-hydroxycholesterol regulate expression of the steroidogenic acute regulatory protein in microvascular endothelial cell line (bEnd.3).

Journal: Biochemical and biophysical research communications 20060421

Title: Apoptotic effects of 25-hydroxycholesterol in immature rat Sertoli cells: prevention by 17beta-estradiol.

Journal: Reproductive toxicology (Elmsford, N.Y.) 20060401

Title: Discovery and optimization of a novel series of liver X receptor-alpha agonists.

Journal: Bioorganic & medicinal chemistry letters 20060315

Title: Analysis of oxysterols by electrospray tandem mass spectrometry.

Journal: Journal of the American Society for Mass Spectrometry 20060301

Title: Coxiella burnetii inhabits a cholesterol-rich vacuole and influences cellular cholesterol metabolism.

Journal: Cellular microbiology 20060301

Title: The influence of cholesterol and lipid metabolism on host cell structure and hepatitis C virus replication.

Journal: Biochemistry and cell biology = Biochimie et biologie cellulaire 20060201

Title: Expression and localization of PCSK9 in rat hepatic cells.

Journal: Biochemistry and cell biology = Biochimie et biologie cellulaire 20060201

Title: Effects of hydroxysterols and atorvastatin on lipopolysaccharide-induced secretion of tumor necrosis factor and interleukin-10 by mouse macrophages.

Journal: Bulletin of experimental biology and medicine 20060201

Title: Physiologic interactions between macrophages and Leydig cells.

Journal: Experimental biology and medicine (Maywood, N.J.) 20060101

Title: Sterol-regulated ubiquitination and degradation of Insig-1 creates a convergent mechanism for feedback control of cholesterol synthesis and uptake.

Journal: Cell metabolism 20060101

Title: Targeted silencing of Jab1/Csn5 in human cells downregulates SCF activity through reduction of F-box protein levels.

Journal: BMC biochemistry 20060101

Title: Receptor Ck-dependent signaling regulates hTERT gene transcription.

Journal: BMC cell biology 20060101

Title: Drug-induced activation of SREBP-controlled lipogenic gene expression in CNS-related cell lines: marked differences between various antipsychotic drugs.

Journal: BMC neuroscience 20060101

Title: Oxidized LDL, a critical factor in atherogenesis.

Journal: Cardiovascular research 20051201

Title: Combined effect of 25-hydroxycholesterol and IL-1beta on IL-8 production in human colon carcinoma cell line (Caco-2).

Journal: Inflammation 20051201

Title: Regulation of adiponectin receptor 1 in human hepatocytes by agonists of nuclear receptors.

Journal: Biochemical and biophysical research communications 20050902

Title: Sterol structure determines miscibility versus melting transitions in lipid vesicles.

Journal: Biophysical journal 20050901

Title: Structural mechanism for sterol sensing and transport by OSBP-related proteins.

Journal: Nature 20050901

Title: Human StarD5, a cytosolic StAR-related lipid binding protein.

Journal: Journal of lipid research 20050801

Title: Is C-26 hydroxylation an evolutionarily conserved steroid inactivation mechanism?

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050801

Title: Inhibition of cholesterol biosynthesis by 25-hydroxycholesterol is independent of OSBP.

Journal: Genes to cells : devoted to molecular & cellular mechanisms 20050801

Title: Insig required for sterol-mediated inhibition of Scap/SREBP binding to COPII proteins in vitro.

Journal: The Journal of biological chemistry 20050715

Title: Isolation of sterol-resistant Chinese hamster ovary cells with genetic deficiencies in both Insig-1 and Insig-2.

Journal: The Journal of biological chemistry 20050701

Title: Cholesterol modulation of the expression of mitochondrial aconitase in human prostatic carcinoma cells.

Journal: The Chinese journal of physiology 20050630

Title: Cholesterol modulates human intestinal sodium-dependent bile acid transporter.

Journal: American journal of physiology. Gastrointestinal and liver physiology 20050501

Title: Tocotrienols reduce 25-hydroxycholesterol-induced monocyte-endothelial cell interaction by inhibiting the surface expression of adhesion molecules.

Journal: Atherosclerosis 20050501

Title: In vivo and in vitro exposures of carp and carp tissues to graded concentrations of endocrine disrupting chemicals.

Journal: Annals of the New York Academy of Sciences 20050401

Title: A new LC/APCI-MS method for the determination of cholesterol oxidation products in food.

Journal: Journal of chromatography. A 20050304

Title: Comparison of the cytotoxic, pro-oxidant and pro-inflammatory characteristics of different oxysterols.

Journal: Cell biology and toxicology 20050301

Title: Post-transcriptional regulation of apoC-I synthesis and secretion in human HepG2 cells.

Journal: Atherosclerosis 20050201

Title: Differential effects of mixtures of cholesterol oxidation products on bovine aortic endothelial cells and human monocytic U937 cells.

Journal: International journal of toxicology 20050101

Title: Cholesterol and 25-hydroxycholesterol inhibit activation of SREBPs by different mechanisms, both involving SCAP and Insigs.

Journal: The Journal of biological chemistry 20041210

Title: Translocation of phospholipase A2 to membranes by oxidized LDL and hydroxyoctadecadienoic acid to contribute to cholesteryl ester formation.

Journal: Biochimica et biophysica acta 20041108

Title: Effects of 25-hydroxycholesterol on cholesterol esterification and sterol regulatory element-binding protein processing are dissociable: implications for cholesterol movement to the regulatory pool in the endoplasmic reticulum.

Journal: The Journal of biological chemistry 20041105

Title: The influence of the amino acid substitution I98K on the catalytic activity of baboon cytochrome P450 side-chain cleavage (CYP11A1).

Journal: Endocrine research 20041101

Title: Role for sterol regulatory element-binding protein in activation of endothelial cells by phospholipid oxidation products.

Journal: Circulation research 20041015

Title: Vascular endothelial growth factor activation of sterol regulatory element binding protein: a potential role in angiogenesis.

Journal: Circulation research 20040903

Title: Platelet-derived growth factor stimulates membrane lipid synthesis through activation of phosphatidylinositol 3-kinase and sterol regulatory element-binding proteins.

Journal: The Journal of biological chemistry 20040820

Title: Mechanisms of cholesterol and sterol regulatory element binding protein regulation of the sterol 12alpha-hydroxylase gene (CYP8B1).

Journal: Biochemical and biophysical research communications 20040806

Title: Statins upregulate PCSK9, the gene encoding the proprotein convertase neural apoptosis-regulated convertase-1 implicated in familial hypercholesterolemia.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20040801

Title: 25-hydroxycholesterol acts in the Golgi compartment to induce degradation of tyrosinase.

Journal: Pigment cell research 20040801

Title: The effect of LXR activators on AP-1 proteins in keratinocytes.

Journal: The Journal of investigative dermatology 20040701

Title: Cell-based screen of HMG-CoA reductase inhibitors and expression regulators using LC-MS.

Journal: Analytical biochemistry 20040601

Title: Rat cytochrome P450C24 (CYP24A1) and the role of F249 in substrate binding and catalytic activity.

Journal: Archives of biochemistry and biophysics 20040515

Title: Sterol regulation of scavenger receptor class B type I in macrophages.

Journal: Journal of lipid research 20040501

Title: Signaling pathway of magnolol-stimulated lipolysis in sterol ester-loaded 3T3-L1 preadipocyes.

Journal: Journal of cellular biochemistry 20040401

Title: Oxysterols regulate expression of the steroidogenic acute regulatory protein.

Journal: Journal of molecular endocrinology 20040401

Title: Effect of LPS on basal and induced apo E secretion by 25-OH chol and 9cRA in differentiated CaCo-2.

Journal: Journal of cellular biochemistry 20040301

Title: Apomine, a novel hypocholesterolemic agent, accelerates degradation of 3-hydroxy-3-methylglutaryl-coenzyme A reductase and stimulates low density lipoprotein receptor activity.

Journal: The Journal of biological chemistry 20040220

Title: Peroxisome proliferator-activated receptor alpha (PPARalpha) activators induce hepatic farnesyl diphosphate synthase gene expression in rodents.

Journal: The Journal of steroid biochemistry and molecular biology 20040201

Title: AKT/protein kinase B regulation of BCL family members during oxysterol-induced apoptosis.

Journal: The Journal of biological chemistry 20040109

Title: CYP3A induction by liver x receptor ligands in primary cultured rat and mouse hepatocytes is mediated by the pregnane X receptor.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20040101

Title: NFY interacts with the promoter region of two genes involved in the rat peroxisomal fatty acid beta-oxidation: the multifunctional protein type 1 and the 3-ketoacyl-CoA B thiolase.

Journal: Lipids in health and disease 20040101

Title: Analysis of cholesterol oxidation products in biological samples.

Journal: Journal of AOAC International 20040101

Title: Inhibitory effects of red wine extracts on endothelial-dependent adhesive interactions with monocytes induced by oxysterols.

Journal: Biological research 20040101

Title: Antisteroidogenic actions of hydrogen peroxide on rat Leydig cells.

Journal: Journal of cellular biochemistry 20031215

Title: Cholesterol oxides mediated changes in cytoskeletal organisation involves Rho GTPases.

Journal: Experimental cell research 20031210

Title: Steroid structural requirements for stabilizing or disrupting lipid domains.

Journal: Biochemistry 20031209

Title: Oxysterol and 9-cis-retinoic acid stimulate the group IIA secretory phospholipase A2 gene in rat smooth-muscle cells.

Journal: The Biochemical journal 20031201

Title: Effects of dehydroepiandrosterone on corticosterone release in rat zona fasciculata-reticularis cells.

Journal: Naunyn-Schmiedeberg's archives of pharmacology 20031201

Title: Identification of natural ligands of retinoic acid receptor-related orphan receptor alpha ligand-binding domain expressed in Sf9 cells--a mass spectrometry approach.

Journal: Analytical biochemistry 20031201

Title: In vivo implants of beta-sitosterol cause reductions of reactive cholesterol pools in mitochondria isolated from gonads of male goldfish (Carassius auratus).

Journal: General and comparative endocrinology 20031201

Title: Clofibrate, a peroxisome-proliferator, enhances reverse cholesterol transport through cytochrome P450 activation and oxysterol generation.

Journal: The Tohoku journal of experimental medicine 20031201

Title: Serum ferritin concentration is associated with plasma levels of cholesterol oxidation products in man.

Journal: Free radical biology & medicine 20031015

Title: 7-ketocholesterol stimulates differentiation of lens epithelial cells.

Journal: Molecular vision 20031006

Title: Origin of oxysterols in hepatic bile of patients with biliary infection.

Journal: The American journal of gastroenterology 20031001

Title: Hypoxia increases 25-hydroxycholesterol-induced interleukin-8 protein secretion in human macrophages.

Journal: Atherosclerosis 20031001

Title: Direct effect of propylthiouracil on progesterone release in rat granulosa cells.

Journal: British journal of pharmacology 20030802

Title: On the substrate specificity of human CYP27A1: implications for bile acid and cholestanol formation.

Journal: Journal of lipid research 20030801

Title: Regulation of PPAR-gamma gene in human promyelocytic HL-60 cell line.

Journal: Leukemia research 20030801

Title: Involvement of the SREBP pathway in the mode of action of androgens in sebaceous glands in vivo.

Journal: Experimental dermatology 20030801

Title: NPC1 and NPC2 regulate cellular cholesterol homeostasis through generation of low density lipoprotein cholesterol-derived oxysterols.

Journal: The Journal of biological chemistry 20030711

Title: Oxysterols suppress constitutive fibrinogen expression.

Journal: Thrombosis and haemostasis 20030701

Title: Sterol-mediated regulation of hormone-sensitive lipase in 3T3-L1 adipocytes.

Journal: Lipids 20030701

Title: Oxysterol-induced toxicity in R28 and ARPE-19 cells.

Journal: Neurochemical research 20030601

Title: PPAR agonists protect mesangial cells from interleukin 1beta-induced intracellular lipid accumulation by activating the ABCA1 cholesterol efflux pathway.

Journal: Journal of the American Society of Nephrology : JASN 20030301

Title: Seasonal alterations in adrenocortical cell function associated with stress-responsiveness and sex in the eastern fence lizard (Sceloporus undulatus).

Journal: Hormones and behavior 20030301

Title: Effects of dioxin (2,3,7,8-TCDD) and PCDDs/PCDFs congeners mixture on steroidogenesis in human placenta tissue culture.

Journal: Endocrine regulations 20030301

Title: Regulation of isoprenoid/cholesterol biosynthesis in cells from mevalonate kinase-deficient patients.

Journal: The Journal of biological chemistry 20030221

Title: Oxysterols induce apoptosis and accumulation of cell cycle at G(2)/M phase in the human monocytic THP-1 cell line.

Journal: Life sciences 20030207

Title: Liver X receptor activators display anti-inflammatory activity in irritant and allergic contact dermatitis models: liver-X-receptor-specific inhibition of inflammation and primary cytokine production.

Journal: The Journal of investigative dermatology 20030201

Title: Cholesterol cell content modulates GTPase activity of G proteins in GH4C1 cell membranes.

Journal: Cellular signalling 20030101

Title: Toxicity of cholesterol oxidation products to Caco-2 and HepG2 cells: modulatory effects of alpha- and gamma-tocopherol.

Journal: Journal of applied toxicology : JAT 20030101

Title: Cholesterol transport and steroidogenesis by the corpus luteum.

Journal: Reproductive biology and endocrinology : RB&E 20030101

Title: On the rate of translocation in vitro and kinetics in vivo of the major oxysterols in human circulation: critical importance of the position of the oxygen function.

Journal: Journal of lipid research 20021201

Title: Testosterone regulates 25-hydroxycholesterol production in testicular macrophages.

Journal: Biology of reproduction 20021101

Title: Bile acids enhance low density lipoprotein receptor gene expression via a MAPK cascade-mediated stabilization of mRNA.

Journal: The Journal of biological chemistry 20021004

Title: Dietary cholesterol-oxidation products accumulate in serum and liver in apolipoprotein E-deficient mice, but do not accelerate atherosclerosis.

Journal: The British journal of nutrition 20021001

Title: Inhibition of testosterone production by propylthiouracil in rat Leydig cells.

Journal: Biology of reproduction 20020801

Title: Cholesterol addition to ER membranes alters conformation of SCAP, the SREBP escort protein that regulates cholesterol metabolism.

Journal: Molecular cell 20020801

Title: Effect of oxysterols on hematopoietic progenitor cells.

Journal: Experimental hematology 20020701

Title: 7-Ketocholesterol and staurosporine induce opposite changes in intracellular pH, associated with distinct types of cell death in ECV304 cells.

Journal: Archives of biochemistry and biophysics 20020615

Title: Dietary cholesterol fails to stimulate the human cholesterol 7alpha-hydroxylase gene (CYP7A1) in transgenic mice.

Journal: The Journal of biological chemistry 20020607

Title: Human organic anion transporting polypeptide 8 promoter is transactivated by the farnesoid X receptor/bile acid receptor.

Journal: Gastroenterology 20020601

Title: Characterization of the estrogenic response to genistein in Japanese medaka (Oryzias latipes).

Journal: Comparative biochemistry and physiology. Toxicology & pharmacology : CBP 20020601

Title: Induction of hepatic inducible nitric oxide synthase by cholesterol in vivo and in vitro.

Journal: Experimental & molecular medicine 20020531

Title: 25-hydroxycholesterol is produced by testicular macrophages during the early postnatal period and influences differentiation of Leydig cells in vitro.

Journal: Biology of reproduction 20020501

Title: 25R,26-Hydroxycholesterol revisited: synthesis, metabolism, and biologic roles.

Journal: Journal of lipid research 20020501

Title: The cDNA cloning and tissue expression of the cytochrome P450scc from Syrian hamster (Mesocricetus auratus).

Journal: General and comparative endocrinology 20020501

Title: Cholesterol, hydroxycholesterols, and bile acids.

Journal: Biochemical and biophysical research communications 20020419

Title: Modulation of goldfish testicular testosterone production in vitro by tumor necrosis factor alpha, interleukin-1beta, and macrophage conditioned media.

Journal: The Journal of experimental zoology 20020401

Title: Lymphatic transport of dietary cholesterol oxidation products, cholesterol and triacylglycerols in rats.

Journal: Bioscience, biotechnology, and biochemistry 20020401

Title: A Link between cholesterol levels and phenobarbital induction of cytochromes P450.

Journal: Biochemical and biophysical research communications 20020222

Title: Oxysterol-binding-protein (OSBP)-related protein 4 binds 25-hydroxycholesterol and interacts with vimentin intermediate filaments.

Journal: The Biochemical journal 20020201

Title: Cellular antioxidant effects of atorvastatin in vitro and in vivo.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20020201

Title: Scavenger receptor class B type I is expressed in cultured keratinocytes and epidermis. Regulation in response to changes in cholesterol homeostasis and barrier requirements.

Journal: The Journal of biological chemistry 20020125

Title: Dissociation of apoptosis induction and CD36 upregulation by enzymatically modified low-density lipoprotein in monocytic cells.

Journal: Biochemical and biophysical research communications 20020125

Title: Induction of monocyte differentiation and foam cell formation in vitro by 7-ketocholesterol.

Journal: Journal of lipid research 20020101

Title: Oxysterols induce interleukin-1beta production in human macrophages.

Journal: European journal of clinical investigation 20020101

Title: Selective effect of cholesterylphosphoserine on intracellular cholesterol transport.

Journal: Lipids 20020101

Title: Green tea catechins decrease apolipoprotein B-100 secretion from HepG2 cells.

Journal: Molecular and cellular biochemistry 20020101

Title: The effect of Puerariae radix on lipoprotein metabolism in liver and intestinal cells.

Journal: BMC complementary and alternative medicine 20020101

Title: Adrenodoxin-cytochrome P450scc interaction as revealed by EPR spectroscopy: comparison with the putidaredoxin-cytochrome P450cam system.

Journal: Journal of biochemistry 20011201

Title: The hypocholesterolemic agent LY295427 reverses suppression of sterol regulatory element-binding protein processing mediated by oxysterols.

Journal: The Journal of biological chemistry 20011130

Title: Acid sphingomyelinase-deficient macrophages have defective cholesterol trafficking and efflux.

Journal: The Journal of biological chemistry 20011130

Title: 7-Ketocholesterol forms crystalline domains in model membranes and murine aortic smooth muscle cells.

Journal: Atherosclerosis 20011101

Title: Growth modulation of low density lipoprotein receptor sterol sensitivity in cultured human fibroblasts.

Journal: Lipids 20011101

Title: Molecular cloning and structural analysis of human sterol C5 desaturase.

Journal: Biochimica et biophysica acta 20011031

Title: Inhibition of the mitogen activated protein kinase, p38 alpha, prevents proinflammatory cytokine induction by human adherent mononuclear leukocytes in response to lipid loading.

Journal: Atherosclerosis 20011001

Title: Arachidonate metabolism and the signaling pathway of induction of apoptosis by oxidized LDL/oxysterol.

Journal: Journal of lipid research 20011001

Title: Regulation of sterol regulatory element-binding proteins by cholesterol flux in CaCo-2 cells.

Journal: Journal of lipid research 20011001

Title: 25-hydroxycholesterol induces lipopolysaccharide-tolerance and decreases a lipopolysaccharide-induced TNF-alpha secretion in macrophages.

Journal: Atherosclerosis 20010901

Title: Binding and uptake of chylomicron remnants by primary and THP-1 human monocyte-derived macrophages: determination of binding proteins.

Journal: Clinical science (London, England : 1979) 20010801

Title: [Studies on the mechanism of arterial in vitro calcification].

Journal: Zhongguo ying yong sheng li xue za zhi = Zhongguo yingyong shenglixue zazhi = Chinese journal of applied physiology 20010801

Title: Woc (without children) gene control of ecdysone biosynthesis in Drosophila melanogaster.

Journal: Molecular and cellular endocrinology 20010705

Title: Concerted transcriptional activation of the low density lipoprotein receptor gene by insulin and luteinizing hormone in cultured porcine granulosa-luteal cells: possible convergence of protein kinase a, phosphatidylinositol 3-kinase, and mitogen-activated protein kinase signaling pathways.

Journal: Endocrinology 20010701

Title: Fatty acid modifications and cholesterol oxidation in pork loin during frying at different temperatures.

Journal: Journal of food protection 20010701

Title: Neurosteroid hydroxylase CYP7B: vivid reporter activity in dentate gyrus of gene-targeted mice and abolition of a widespread pathway of steroid and oxysterol hydroxylation.

Journal: The Journal of biological chemistry 20010629

Title: Plant sterols regulate rat vascular smooth muscle cell growth and prostacyclin release in culture.

Journal: Prostaglandins, leukotrienes, and essential fatty acids 20010601

Title: Stimulatory effect of lactate on testosterone production by rat Leydig cells.

Journal: Journal of cellular biochemistry 20010601

Title: Novel members of the human oxysterol-binding protein family bind phospholipids and regulate vesicle transport.

Journal: The Journal of biological chemistry 20010525

Title: Selective distribution of oxysterols in atherosclerotic lesions and human plasma lipoproteins.

Journal: Free radical research 20010501

Title: An oxidized derivative of cholesterol increases the release of soluble vascular cell adhesion molecule-1 from human umbilical vein endothelial cells in culture.

Journal: Biochimica et biophysica acta 20010430

Title: Differential modulation of ACAT1 and ACAT2 transcription and activity by long chain free fatty acids in cultured cells.

Journal: Biochemistry 20010417

Title: cyp7b1 catalyses the 7alpha-hydroxylation of dehydroepiandrosterone and 25-hydroxycholesterol in rat prostate.

Journal: The Biochemical journal 20010415

Title: Coronary atherosclerosis and oxidative stress as reflected by autoantibodies against oxidized low-density lipoprotein and oxysterols.

Journal: Atherosclerosis 20010401

Title: Key regulatory oxysterols in liver: analysis as delta4-3-ketone derivatives by HPLC and response to physiological perturbations.

Journal: Journal of lipid research 20010401

Title: Direct inhibitory effect of digitalis on progesterone release from rat granulosa cells.

Journal: British journal of pharmacology 20010401

Title: Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha.

Journal: Journal of medicinal chemistry 20010315

Title: Fas/Fas ligand-mediated death pathway is involved in oxLDL-induced apoptosis in vascular smooth muscle cells.

Journal: American journal of physiology. Cell physiology 20010301

Title: Production of 25-hydroxycholesterol by testicular macrophages and its effects on Leydig cells.

Journal: Biology of reproduction 20010301

Title: Control of apolipoprotein E secretion in the human hepatoma cell line KYN-2.

Journal: Cell biochemistry and function 20010301

Title: Cholesterol biosynthesis from lanosterol: molecular cloning, chromosomal localization, functional expression and liver-specific gene regulation of rat sterol delta8-isomerase, a cholesterogenic enzyme with multiple functions.

Journal: The Biochemical journal 20010201

Title: Mechanism of action of noradrenaline on secretion of progesterone and oxytocin by the bovine corpus luteum in vitro.

Journal: Acta veterinaria Hungarica 20010101

Title: Comparative study of the cytotoxicity and apoptosis-inducing potential of commonly occurring oxysterols.

Journal: Cell biology and toxicology 20010101

Title: Control of apolipoprotein E secretion by 25-hydroxycholesterol and proinflammatory cytokines in the human astrocytoma cell line CCF-STTG1.

Journal: Cell biology and toxicology 20010101

Title: Peroxisome proliferator-activated receptor agonists prevent 25-OH-cholesterol induced c-jun activation and cell death.

Journal: BMC pharmacology 20010101

Title: Oxysterol 7 alpha-hydroxylase activity by cholesterol 7 alpha-hydroxylase (CYP7A).

Journal: The Journal of biological chemistry 20001103

Title: Expression cloning of an oxysterol 7alpha-hydroxylase selective for 24-hydroxycholesterol.

Journal: The Journal of biological chemistry 20000602

Title: The mevalonate/isoprenoid pathway inhibitor apomine (SR-45023A) is antiproliferative and induces apoptosis similar to farnesol.

Journal: Biochemical and biophysical research communications 20000402

Title: Down-regulation of mammalian 3-hydroxy-3-methylglutaryl coenzyme A reductase activity with highly purified liposomal cholesterol.

Journal: European journal of biochemistry 19991201

Title: Oxysterol regulation of steroidogenic acute regulatory protein gene expression. Structural specificity and transcriptional and posttranscriptional actions.

Journal: The Journal of biological chemistry 19981113

Title: Oxysterols, but not cholesterol, inhibit human immunodeficiency virus replication in vitro.

Journal: Antiviral chemistry & chemotherapy 19981101

Title: Meiosis-activating sterol promotes resumption of meiosis in mouse oocytes cultured in vitro in contrast to related oxysterols.

Journal: Biology of reproduction 19980501

Title: Activation of the orphan nuclear receptor steroidogenic factor 1 by oxysterols.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19970513

Title: Studies on the relationships between 7 alpha-hydroxylation and the ability of 25- and 27-hydroxycholesterol to suppress the activity of HMG-CoA reductase.

Journal: Biochimica et biophysica acta 19970218

Title: Activation of the nuclear receptor LXR by oxysterols defines a new hormone response pathway.

Journal: The Journal of biological chemistry 19970207

Title: Oxysterols present in atherosclerotic tissue decrease the expression of lipoprotein lipase messenger RNA in human monocyte-derived macrophages.

Journal: The Journal of clinical investigation 19960115

Title: Effects of 26-aminocholesterol, 27-hydroxycholesterol, and 25-hydroxycholesterol on proliferation and cholesterol homeostasis in arterial myocytes.

Journal: Arteriosclerosis, thrombosis, and vascular biology 19950301

Title: Structural specificity in the suppression of HMG-CoA reductase in human fibroblasts by intermediates in bile acid biosynthesis.

Journal: Journal of lipid research 19950201

Title: 7 alpha hydroxylation of 25-hydroxycholesterol in liver microsomes. Evidence that the enzyme involved is different from cholesterol 7 alpha-hydroxylase.

Journal: European journal of biochemistry 19940901

Title: Atherosclerosis and sterol 27-hydroxylase: evidence for a role of this enzyme in elimination of cholesterol from human macrophages.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19940830

Title: 24-, 25- and 27-hydroxylation of cholesterol by a purified preparation of 27-hydroxylase from pig liver.

Journal: Biochimica et biophysica acta 19930224

Title: McDonald JG, et al. Editorial: 25-Hydroxycholesterol: a new life in immunology. J Leukoc Biol. 2010 Dec;88(6):1071-2.

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Tags:2140-46-7 Molecular Formula|2140-46-7 MDL|2140-46-7 SMILES|2140-46-7 (8S,9S,10R,13R,14S,17R)-17-((R)-6-Hydroxy-6-methylheptan-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