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153559-76-3,MFCD01758574
Catalog No.:AA00AAZI

153559-76-3 | 6-[1-(3,5,5,8,8-PENTAMETHYL-5,6,7,8-TETRAHYDRO-NAPHTHALEN-2-YL)-CYCLOPROPYL]-NICOTINIC ACID

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1mg
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5mg
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00AAZI
Chemical Name:
6-[1-(3,5,5,8,8-PENTAMETHYL-5,6,7,8-TETRAHYDRO-NAPHTHALEN-2-YL)-CYCLOPROPYL]-NICOTINIC ACID
CAS Number:
153559-76-3
Molecular Formula:
C24H29NO2
Molecular Weight:
363.4926
MDL Number:
MFCD01758574
SMILES:
Cc1cc2c(cc1C1(CC1)c1ccc(cn1)C(=O)O)C(C)(C)CCC2(C)C
Properties
Computed Properties
 
Complexity:
591  
Covalently-Bonded Unit Count:
1  
Heavy Atom Count:
27  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
1  
Rotatable Bond Count:
3  
XLogP3:
6.1  

Literature

Title: Tributyltin induces a transcriptional response without a brite adipocyte signature in adipocyte models.

Journal: Archives of toxicology 20180901

Title: Tributyltin engages multiple nuclear receptor pathways and suppresses osteogenesis in bone marrow multipotent stromal cells.

Journal: Chemical research in toxicology 20150615

Title: Identification of potent Yes1 kinase inhibitors using a library screening approach.

Journal: Bioorganic & medicinal chemistry letters 20130801

Title: Mechanisms of action of hormone-sensitive lipase in mouse Leydig cells: its role in the regulation of the steroidogenic acute regulatory protein.

Journal: The Journal of biological chemistry 20130322

Title: Regulation of sphingomyelin phosphodiesterase acid-like 3A gene (SMPDL3A) by liver X receptors.

Journal: Molecular pharmacology 20121001

Title: The combination of tamoxifen and the rexinoid LG100268 prevents ER-positive and ER-negative mammary tumors in p53-null mammary gland mice.

Journal: Cancer prevention research (Philadelphia, Pa.) 20121001

Title: Tributyltin synergizes with 20-hydroxyecdysone to produce endocrine toxicity.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20110901

Title: Research resource: transcriptome profiling of genes regulated by RXR and its permissive and nonpermissive partners in differentiating monocyte-derived dendritic cells.

Journal: Molecular endocrinology (Baltimore, Md.) 20101101

Title: Synthetic triterpenoids prolong survival in a transgenic mouse model of pancreatic cancer.

Journal: Cancer prevention research (Philadelphia, Pa.) 20101101

Title: Retinoic acid regulates myelin formation in the peripheral nervous system.

Journal: Glia 20100901

Title: Gene regulation of CYP4F11 in human keratinocyte HaCaT cells.

Journal: Drug metabolism and disposition: the biological fate of chemicals 20100101

Title: Triterpenoids CDDO-methyl ester or CDDO-ethyl amide and rexinoids LG100268 or NRX194204 for prevention and treatment of lung cancer in mice.

Journal: Cancer prevention research (Philadelphia, Pa.) 20091201

Title: Placental steroidogenesis in rats is independent of signaling pathways induced by retinoic acids.

Journal: General and comparative endocrinology 20090915

Title: Peroxisome proliferator-activated receptor-gamma and retinoid X receptor agonists synergistically suppress proliferation of immortalized endometrial stromal cells.

Journal: Fertility and sterility 20090501

Title: Rexinoids modulate steroid and xenobiotic receptor activity by increasing its protein turnover in a calpain-dependent manner.

Journal: The Journal of biological chemistry 20080808

Title: Prevention and treatment of experimental estrogen receptor-negative mammary carcinogenesis by the synthetic triterpenoid CDDO-methyl Ester and the rexinoid LG100268.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20080715

Title: The rexinoid LG100268 and the synthetic triterpenoid CDDO-methyl amide are more potent than erlotinib for prevention of mouse lung carcinogenesis.

Journal: Molecular cancer therapeutics 20080501

Title: Development and quality of bovine morulae cultured in serum-free medium with specific retinoid receptor agonists.

Journal: Reproduction, fertility, and development 20080101

Title: PPARgamma-active triterpenoid CDDO enhances ATRA-induced differentiation in APL.

Journal: Cancer biology & therapy 20071201

Title: Retinoid receptor-specific agonists regulate bovine in vitro early embryonic development, differentiation and expression of genes related to cell cycle arrest and apoptosis.

Journal: Theriogenology 20071101

Title: In silico prediction of pregnane X receptor activators by machine learning approaches.

Journal: Molecular pharmacology 20070101

Title: Identification of biomarkers modulated by the rexinoid LGD1069 (bexarotene) in human breast cells using oligonucleotide arrays.

Journal: Cancer research 20061215

Title: The combination of the rexinoid, LG100268, and a selective estrogen receptor modulator, either arzoxifene or acolbifene, synergizes in the prevention and treatment of mammary tumors in an estrogen receptor-negative model of breast cancer.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20061001

Title: Neu-induced retroviral rat mammary carcinogenesis: a novel chemoprevention model for both hormonally responsive and nonresponsive mammary carcinomas.

Journal: Cancer research 20060701

Title: PPARalpha activators and fasting induce the expression of adipose differentiation-related protein in liver.

Journal: Journal of lipid research 20060501

Title: Organotin compounds enhance 17beta-hydroxysteroid dehydrogenase type I activity in human choriocarcinoma JAr cells: potential promotion of 17beta-estradiol biosynthesis in human placenta.

Journal: Biochemical pharmacology 20060428

Title: Receptor-selective retinoids inhibit the growth of normal and malignant breast cells by inducing G1 cell cycle blockade.

Journal: Breast cancer research and treatment 20060301

Title: Coactivation of liver receptor homologue-1 by peroxisome proliferator-activated receptor gamma coactivator-1alpha on aromatase promoter II and its inhibition by activated retinoid X receptor suggest a novel target for breast-specific antiestrogen therapy.

Journal: Cancer research 20051215

Title: Distinct mechanisms of glucose lowering by specific agonists for peroxisomal proliferator activated receptor gamma and retinoic acid X receptors.

Journal: The Journal of biological chemistry 20051118

Title: Trialkyltin compounds bind retinoid X receptor to alter human placental endocrine functions.

Journal: Molecular endocrinology (Baltimore, Md.) 20051001

Title: Peroxisome proliferator-activated receptor alpha (PPARalpha) potentiates, whereas PPARgamma attenuates, glucose-stimulated insulin secretion in pancreatic beta-cells.

Journal: Endocrinology 20050801

Title: Thiazolidinediones inhibit proliferation of microvascular and macrovascular cells by a PPARgamma-independent mechanism.

Journal: Diabetologia 20050301

Title: Activation of peroxisome proliferator-activated receptor-gamma and retinoid X receptor inhibits aromatase transcription via nuclear factor-kappaB.

Journal: Endocrinology 20050101

Title: Rexinoids may be ready for prime time in prevention, but challenges remain.

Journal: Journal of the National Cancer Institute 20041215

Title: Molecular cloning and characterization of two novel human RXR alpha splice variants.

Journal: The Journal of steroid biochemistry and molecular biology 20040901

Title: Spatiotemporal retinoid-X receptor activation detected in live vertebrate embryos.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20040615

Title: The selective estrogen receptor modulator arzoxifene and the rexinoid LG100268 cooperate to promote transforming growth factor beta-dependent apoptosis in breast cancer.

Journal: Cancer research 20040515

Title: Design, synthesis and structure-activity relationship of novel RXR-selective modulators.

Journal: Bioorganic & medicinal chemistry letters 20040322

Title: Design and synthesis of novel RXR-selective modulators with improved pharmacological profile.

Journal: Bioorganic & medicinal chemistry letters 20031117

Title: Design, synthesis, and structure-activity relationship studies of novel 6,7-locked-[7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta]-2,4,6-trienoic acids.

Journal: Journal of medicinal chemistry 20030911

Title: Novel (2E,4E,6Z)-7-(2-alkoxy-3,5-dialkylbenzene)-3-methylocta-2,4,6-trienoic acid retinoid X receptor modulators are active in models of type 2 diabetes.

Journal: Journal of medicinal chemistry 20030619

Title: Retinoid X receptor (RXR) agonist-induced antagonism of farnesoid X receptor (FXR) activity due to absence of coactivator recruitment and decreased DNA binding.

Journal: The Journal of biological chemistry 20030321

Title: Prevention and treatment of experimental breast cancer with the combination of a new selective estrogen receptor modulator, arzoxifene, and a new rexinoid, LG 100268.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20021001

Title: Mechanism of selective retinoid X receptor agonist-induced hypothyroidism in the rat.

Journal: Endocrinology 20020801

Title: Redundant pathways for negative feedback regulation of bile acid production.

Journal: Developmental cell 20020601

Title: The structural basis for the specificity of retinoid-X receptor-selective agonists: new insights into the role of helix H12.

Journal: The Journal of biological chemistry 20020329

Title: Regional differences in the response of human pre-adipocytes to PPARgamma and RXRalpha agonists.

Journal: Diabetes 20020301

Title: PPARgamma is not a critical mediator of primary monocyte differentiation or foam cell formation.

Journal: Biochemical and biophysical research communications 20020118

Title: Regulation of aromatase by nuclear receptors.

Journal: The Journal of steroid biochemistry and molecular biology 20011201

Title: Inhibition of RXR and PPARgamma ameliorates diet-induced obesity and type 2 diabetes.

Journal: The Journal of clinical investigation 20011001

Title: The rexinoid LG100754 is a novel RXR:PPARgamma agonist and decreases glucose levels in vivo.

Journal: Molecular endocrinology (Baltimore, Md.) 20010801

Title: Combined treatment with specific ligands for PPARgamma:RXR nuclear receptor system markedly inhibits the expression of cytochrome P450arom in human granulosa cancer cells.

Journal: Molecular and cellular endocrinology 20010705

Title: Differential effects of rexinoids and thiazolidinediones on metabolic gene expression in diabetic rodents.

Journal: Molecular pharmacology 20010401

Title: Peroxisome proliferator-activated receptor (PPAR) gamma and retinoid X receptor (RXR) agonists have complementary effects on glucose and lipid metabolism in human skeletal muscle.

Journal: Diabetologia 20010401

Title: Metabolic effects of rexinoids: tissue-specific regulation of lipoprotein lipase activity.

Journal: Molecular pharmacology 20010201

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

Journal: Gene 20010110

Title: The effects of rexinoids and rosiglitazone on body weight and uncoupling protein isoform expression in the Zucker fa/fa rat.

Journal: Metabolism: clinical and experimental 20001201

Title: A synthetic triterpenoid, 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO), is a ligand for the peroxisome proliferator-activated receptor gamma.

Journal: Molecular endocrinology (Baltimore, Md.) 20001001

Title: Insulin sensitizer, troglitazone, directly inhibits aromatase activity in human ovarian granulosa cells.

Journal: Biochemical and biophysical research communications 20000519

Title: Induction of the fatty acid transport protein 1 and acyl-CoA synthase genes by dimer-selective rexinoids suggests that the peroxisome proliferator-activated receptor-retinoid X receptor heterodimer is their molecular target.

Journal: The Journal of biological chemistry 20000428

Title: The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.

Journal: Molecular endocrinology (Baltimore, Md.) 20000101

Title: Therapeutic applications for ligands of retinoid receptors.

Journal: Current pharmaceutical design 20000101

Title: Growth inhibition of myeloid leukemia cells by troglitazone, a ligand for peroxisome proliferator activated receptor gamma, and retinoids.

Journal: International journal of oncology 19991101

Title: Activation of specific RXR heterodimers by an antagonist of RXR homodimers.

Journal: Nature 19961003

Title: Retinoids increase human apolipoprotein A-11 expression through activation of the retinoid X receptor but not the retinoic acid receptor.

Journal: Molecular and cellular biology 19960701

Title: Synthesis of high specific activity [3H]-9-cis-retinoic acid and its application for identifying retinoids with unusual binding properties.

Journal: Journal of medicinal chemistry 19940204

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Tags:153559-76-3 Molecular Formula|153559-76-3 MDL|153559-76-3 SMILES|153559-76-3 6-[1-(3,5,5,8,8-PENTAMETHYL-5,6,7,8-TETRAHYDRO-NAPHTHALEN-2-YL)-CYCLOPROPYL]-NICOTINIC ACID