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17954-98-2,MFCD00070042
Catalog No.:AA00270C

17954-98-2 | (8S,9S,10R,13S,14S,17R)-17-((2S,3R)-3-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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  • Technical Information
  • Properties
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Technical Information
Catalog Number:
AA00270C
Chemical Name:
(8S,9S,10R,13S,14S,17R)-17-((2S,3R)-3-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:
17954-98-2
Molecular Formula:
C27H46O2
Molecular Weight:
402.6529
MDL Number:
MFCD00070042
SMILES:
CC(CC[C@H]([C@H]([C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CC=C2[C@]1(C)CC[C@@H](C2)O)C)O)C
Properties
Computed Properties
 
Complexity:
624  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
9  
Heavy Atom Count:
29  
Hydrogen Bond Acceptor Count:
2  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  
XLogP3:
7  

Literature

Title: Expression of CYP4V2 in human THP1 macrophages and its transcriptional regulation by peroxisome proliferator-activated receptor gamma.

Journal: Toxicology and applied pharmacology 20170901

Title: In vivo production of novel vitamin D2 hydroxy-derivatives by human placentas, epidermal keratinocytes, Caco-2 colon cells and the adrenal gland.

Journal: Molecular and cellular endocrinology 20140305

Title: Cisplatin inhibits testosterone synthesis by a mechanism that includes the action of reactive oxygen species (ROS) at the level of P450scc.

Journal: Chemico-biological interactions 20120930

Title: LXR agonists and ABCG1-dependent cholesterol efflux in MCF-7 breast cancer cells: relation to proliferation and apoptosis.

Journal: Anticancer research 20120701

Title: Dietary supplementation with 22-S-hydroxycholesterol to rats reduces body weight gain and the accumulation of liver triacylglycerol.

Journal: Lipids 20120501

Title: Liver X receptor activation downregulates organic anion transporter 1 (OAT1) in the renal proximal tubule.

Journal: American journal of physiology. Renal physiology 20120301

Title: The liver X receptor modulator 22(S)-hydroxycholesterol exerts cell-type specific effects on lipid and glucose metabolism.

Journal: The Journal of steroid biochemistry and molecular biology 20120201

Title: A steroid isolated from the water mold Achlya heterosexualis induces neurogenesis in vitro and in vivo.

Journal: Steroids 20120201

Title: Caprospinol: discovery of a steroid drug candidate to treat Alzheimer's disease based on 22R-hydroxycholesterol structure and properties.

Journal: Journal of neuroendocrinology 20120101

Title: Simvastatin reduces steroidogenesis by inhibiting Cyp17a1 gene expression in rat ovarian theca-interstitial cells.

Journal: Biology of reproduction 20120101

Title: Regulation of LXR by fatty acids, insulin, growth hormone and tumor necrosis factor-α in rainbow trout myocytes.

Journal: Comparative biochemistry and physiology. Part A, Molecular & integrative physiology 20111001

Title: Dysregulation of SREBP2 induces BACE1 expression.

Journal: Neurobiology of disease 20111001

Title: The human placenta expresses CYP17 and generates androgens de novo.

Journal: The Journal of clinical endocrinology and metabolism 20110501

Title: Structural basis for three-step sequential catalysis by the cholesterol side chain cleavage enzyme CYP11A1.

Journal: The Journal of biological chemistry 20110218

Title: Oxysterols inhibit differentiation and fusion of term primary trophoblasts by activating liver X receptors.

Journal: Placenta 20110201

Title: Antiproliferative effect of LXR agonists T0901317 and 22(R)-hydroxycholesterol on multiple human cancer cell lines.

Journal: Anticancer research 20100901

Title: Identification of a naturally occurring rexinoid, honokiol, that activates the retinoid X receptor.

Journal: Journal of natural products 20100827

Title: Testosterone synthesized in cultured human SZ95 sebocytes derives mainly from dehydroepiandrosterone.

Journal: Experimental dermatology 20100501

Title: Mesenchymal stem cells differentiate into renin-producing juxtaglomerular (JG)-like cells under the control of liver X receptor-alpha.

Journal: The Journal of biological chemistry 20100416

Title: LXR-activating oxysterols induce the expression of inflammatory markers in endothelial cells through LXR-independent mechanisms.

Journal: Atherosclerosis 20091101

Title: Effects of cholesterol and cAMP on progesterone production in cultured luteal cells isolated from pseudopregnant cat ovaries.

Journal: Animal reproduction science 20091001

Title: Mechanism underlying apolipoprotein E (ApoE) isoform-dependent lipid efflux from neural cells in culture.

Journal: Journal of neuroscience research 20090815

Title: OSBP-related protein 2 is a sterol receptor on lipid droplets that regulates the metabolism of neutral lipids.

Journal: Journal of lipid research 20090701

Title: Activators of PPARs and LXR decrease the adverse effects of exogenous glucocorticoids on the epidermis.

Journal: Experimental dermatology 20090701

Title: Highly sensitive quantification of key regulatory oxysterols in biological samples by LC-ESI-MS/MS.

Journal: Journal of lipid research 20090201

Title: Transport-metabolism interplay: LXRalpha-mediated induction of human ABC transporter ABCC2 (cMOAT/MRP2) in HepG2 cells.

Journal: Molecular pharmaceutics 20090101

Title: Androgen deprivation by activating the liver X receptor.

Journal: Endocrinology 20080801

Title: Epoxycholesterol impairs cholesteryl ester hydrolysis in macrophage foam cells, resulting in decreased cholesterol efflux.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20080601

Title: Co-existence of alpha-glucosidase-inhibitory and liver X receptor-regulatory activities and their separation by structural development.

Journal: Bioorganic & medicinal chemistry 20080415

Title: Expression and biological activity of ABCA1 in alveolar epithelial cells.

Journal: American journal of respiratory cell and molecular biology 20080301

Title: Fenvalerate inhibits progesterone production through cAMP-dependent signal pathway.

Journal: Toxicology letters 20080104

Title: 22R-Hydroxycholesterol induces differentiation of human NT2 precursor (Ntera2/D1 teratocarcinoma) cells.

Journal: Neuroscience 20070824

Title: Monobutyl phthalate inhibits steroidogenesis by downregulating steroidogenic acute regulatory protein expression in mouse Leydig tumor cells (MLTC-1).

Journal: Journal of toxicology and environmental health. Part A 20070601

Title: 22-Hydroxycholesterols regulate lipid metabolism differently than T0901317 in human myotubes.

Journal: Biochimica et biophysica acta 20061201

Title: Sesquiterpene lactone helenalin suppresses Leydig and adrenocortical cell steroidogenesis by inhibiting expression of the steroidogenic acute regulatory protein.

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

Title: Energized, polarized, and actively respiring mitochondria are required for acute Leydig cell steroidogenesis.

Journal: Endocrinology 20060801

Title: Synergistic effect of peroxisome proliferator activated receptor-gamma and liver X receptor-alpha in the regulation of inflammation in macrophages.

Journal: Shock (Augusta, Ga.) 20060801

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

Journal: Lipids 20060601

Title: Oxysterol 22(R)-hydroxycholesterol induces the expression of the bile salt export pump through nuclear receptor farsenoid X receptor but not liver X receptor.

Journal: The Journal of pharmacology and experimental therapeutics 20060401

Title: Carbaryl inhibits basal and FSH-induced progesterone biosynthesis of primary human granulosa-lutein cells.

Journal: Toxicology 20060301

Title: Suppression of inducible nitric oxide synthase and cyclooxygenase-2 gene expression by 22(R)-hydroxycholesterol requires de novo protein synthesis in activated macrophages.

Journal: The Journal of steroid biochemistry and molecular biology 20051201

Title: Liver X receptors mediate inhibition of hCG secretion in a human placental trophoblast cell line.

Journal: Placenta 20051101

Title: Liver X receptor and retinoic X receptor agonists modulate the expression of genes involved in lipid metabolism in human endothelial cells.

Journal: International journal of molecular medicine 20051001

Title: Osteogenic oxysterols inhibit the adverse effects of oxidative stress on osteogenic differentiation of marrow stromal cells.

Journal: Journal of cellular biochemistry 20050815

Title: Diterpenoid, steroid, and triterpenoid agonists of liver X receptors from diversified terrestrial plants and marine sources.

Journal: Journal of natural products 20050801

Title: Discovery and development of dimeric podocarpic acid leads as potent agonists of liver X receptor with HDL cholesterol raising activity in mice and hamsters.

Journal: Bioorganic & medicinal chemistry letters 20050602

Title: Effects of fenvalerate on steroidogenesis in cultured rat granulosa cells.

Journal: Biomedical and environmental sciences : BES 20050401

Title: Regulatory mechanism of Toona sinensis on mouse leydig cell steroidogenesis.

Journal: Life sciences 20050211

Title: Peripheral-type benzodiazepine receptor-mediated action of steroidogenic acute regulatory protein on cholesterol entry into leydig cell mitochondria.

Journal: Molecular endocrinology (Baltimore, Md.) 20050201

Title: Cellular physiology of cholesterol efflux in vascular endothelial cells.

Journal: Circulation 20041102

Title: Rosiglitazone upregulates caveolin-1 expression in THP-1 cells through a PPAR-dependent mechanism.

Journal: Journal of lipid research 20041101

Title: Evaluation of the role of FSH in regulation of Leydig cell function during different stages of its differentiation.

Journal: Molecular and cellular endocrinology 20040930

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

Journal: The Journal of investigative dermatology 20040701

Title: Oxidized LDL upregulated ATP binding cassette transporter-1 in THP-1 macrophages.

Journal: Acta pharmacologica Sinica 20040501

Title: Role of p160 coactivator complex in the activation of liver X receptor.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20040401

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

Journal: Journal of molecular endocrinology 20040401

Title: Apolipoprotein A-I activates cellular cAMP signaling through the ABCA1 transporter.

Journal: The Journal of biological chemistry 20040312

Title: Verapamil increases the apolipoprotein-mediated release of cellular cholesterol by induction of ABCA1 expression via Liver X receptor-independent mechanism.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20040301

Title: Oxysterols induce cyclooxygenase-2 expression in cholangiocytes: implications for biliary tract carcinogenesis.

Journal: Hepatology (Baltimore, Md.) 20040301

Title: Molecular and cellular physiology of apolipoprotein A-I lipidation by the ATP-binding cassette transporter A1 (ABCA1).

Journal: The Journal of biological chemistry 20040227

Title: Inhibitory actions of lead on steroidogenesis in MA-10 mouse Leydig tumor cells.

Journal: Archives of andrology 20040101

Title: Identification of naturally occurring spirostenols preventing beta-amyloid-induced neurotoxicity.

Journal: Steroids 20040101

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: Identification and characterization of rodent ABCA1 in isolated type II pneumocytes.

Journal: American journal of physiology. Lung cellular and molecular physiology 20031001

Title: Induction of intestinal ATP-binding cassette transporters by a phytosterol-derived liver X receptor agonist.

Journal: The Journal of biological chemistry 20030919

Title: Cross-talk between peroxisome proliferator-activated receptor (PPAR) alpha and liver X receptor (LXR) in nutritional regulation of fatty acid metabolism. II. LXRs suppress lipid degradation gene promoters through inhibition of PPAR signaling.

Journal: Molecular endocrinology (Baltimore, Md.) 20030701

Title: Oxysterols suppress constitutive fibrinogen expression.

Journal: Thrombosis and haemostasis 20030701

Title: Human skin is a steroidogenic tissue: steroidogenic enzymes and cofactors are expressed in epidermis, normal sebocytes, and an immortalized sebocyte cell line (SEB-1).

Journal: The Journal of investigative dermatology 20030601

Title: Regulatory mechanism of Cordyceps sinensis mycelium on mouse Leydig cell steroidogenesis.

Journal: FEBS letters 20030522

Title: The inhibitory effects of manganese on steroidogenesis in rat primary Leydig cells by disrupting steroidogenic acute regulatory (StAR) protein expression.

Journal: Toxicology 20030503

Title: Membrane incorporation of 22-hydroxycholesterol inhibits chemokine receptor activity.

Journal: Experimental cell research 20030501

Title: 22R-hydroxycholesterol and 9-cis-retinoic acid induce ATP-binding cassette transporter A1 expression and cholesterol efflux in brain cells and decrease amyloid beta secretion.

Journal: The Journal of biological chemistry 20030411

Title: Formation and functioning of fused cholesterol side-chain cleavage enzymes.

Journal: DNA and cell biology 20030401

Title: Differential regulation of rat and human CYP7A1 by the nuclear oxysterol receptor liver X receptor-alpha.

Journal: Molecular endocrinology (Baltimore, Md.) 20030301

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: Oxysterol-activated LXRalpha/RXR induces hSR-BI-promoter activity in hepatoma cells and preadipocytes.

Journal: Biochemical and biophysical research communications 20021220

Title: 22R-Hydroxycholesterol protects neuronal cells from beta-amyloid-induced cytotoxicity by binding to beta-amyloid peptide.

Journal: Journal of neurochemistry 20021201

Title: Truncation mutations in ABCA1 suppress normal upregulation of full-length ABCA1 by 9-cis-retinoic acid and 22-R-hydroxycholesterol.

Journal: Journal of lipid research 20021101

Title: ATP-binding cassette transporter 1 participates in LDL oxidation by artery wall cells.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20021101

Title: Stimulation of progesterone production in human granulosa-lutein cells by lipoproteins: evidence for cholesterol-independent actions of high-density lipoproteins.

Journal: The Journal of endocrinology 20020401

Title: Alterations in ovarian follicular progesterone secretion by elevated exposures to the drinking water disinfection by-product dibromoacetic acid: examination of the potential site(s) of impact along the steroidogenic pathway.

Journal: Toxicology 20020227

Title: Macrophage cholesterol efflux to free apoprotein A-I in C3H and C57BL/6 mice.

Journal: Biochemical and biophysical research communications 20020208

Title: Expression and functional analyses of novel mutations of ATP-binding cassette transporter-1 in Japanese patients with high-density lipoprotein deficiency.

Journal: Biochemical and biophysical research communications 20020118

Title: Oxysterol stimulation of epidermal differentiation is mediated by liver X receptor-beta in murine epidermis.

Journal: The Journal of investigative dermatology 20020101

Title: Functional analysis of the transcriptional activity of the mouse phospholipid transfer protein gene.

Journal: Biochemical and biophysical research communications 20011005

Title: Leukemia inhibitory factor antagonizes gonadotropin induced-testosterone synthesis in cultured porcine leydig cells: sites of action.

Journal: Endocrinology 20010601

Title: Creation and activity of COS-1 cells stably expressing the F2 fusion of the human cholesterol side-chain cleavage enzyme system.

Journal: Endocrinology 20010601

Title: Luteinization factor-stimulated steroidogenesis in porcine granulosa cells.

Journal: General physiology and biophysics 20010601

Title: Pharmacophore analysis of the nuclear oxysterol receptor LXRalpha.

Journal: Journal of medicinal chemistry 20010315

Title: Genomic sequence and structure of the human ABCG1 (ABC8) gene.

Journal: Biochemical and biophysical research communications 20010112

Title: The inhibitory effects of lead on steroidogenesis in MA-10 mouse Leydig tumor cells.

Journal: Life sciences 20010112

Title: Regulation of cholesterol 7alpha-hydroxylase gene (CYP7A1) transcription by the liver orphan receptor (LXRalpha).

Journal: Gene 20010110

Title: Melatonin inhibits the expression of steroidogenic acute regulatory protein and steroidogenesis in MA-10 cells.

Journal: Journal of andrology 20010101

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

Journal: The Journal of biological chemistry 19970207

Title: An oxysterol signalling pathway mediated by the nuclear receptor LXR alpha.

Journal: Nature 19961024

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Tags:17954-98-2 Molecular Formula|17954-98-2 MDL|17954-98-2 SMILES|17954-98-2 (8S,9S,10R,13S,14S,17R)-17-((2S,3R)-3-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