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73573-88-3

73573-88-3 | Butanoic acid, 2-methyl-, (1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, (2S)-

CAS No: 73573-88-3 Catalog No: AG0038GT MDL No:MFCD05662341

Product Description

Catalog Number:
AG0038GT
Chemical Name:
Butanoic acid, 2-methyl-, (1S,7S,8S,8aR)-1,2,3,7,8,8a-hexahydro-7-methyl-8-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-1-naphthalenyl ester, (2S)-
CAS Number:
73573-88-3
Molecular Formula:
C23H34O5
Molecular Weight:
390.5131
MDL Number:
MFCD05662341
IUPAC Name:
[(1S,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-7-methyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate
InChI:
InChI=1S/C23H34O5/c1-4-14(2)23(26)28-20-7-5-6-16-9-8-15(3)19(22(16)20)11-10-18-12-17(24)13-21(25)27-18/h6,8-9,14-15,17-20,22,24H,4-5,7,10-13H2,1-3H3/t14-,15-,17+,18+,19-,20-,22-/m0/s1
InChI Key:
AJLFOPYRIVGYMJ-INTXDZFKSA-N
SMILES:
CC[C@@H](C(=O)O[C@H]1CCC=C2[C@H]1[C@@H](CC[C@@H]1C[C@@H](O)CC(=O)O1)[C@H](C=C2)C)C
EC Number:
700-442-0
UNII:
1UQM1K0W9X

Properties

Complexity:
637  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
7  
Defined Bond Stereocenter Count:
0
Exact Mass:
390.241g/mol
Formal Charge:
0
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
1  
Isotope Atom Count:
0
Molecular Weight:
390.52g/mol
Monoisotopic Mass:
390.241g/mol
Rotatable Bond Count:
7  
Topological Polar Surface Area:
72.8A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.9  

Literature

Title Journal
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Efficient bioconversion of compactin to pravastatin by the quinoline-degrading microorganism Pseudonocardia carboxydivorans isolated from petroleum-contaminated soil. Bioresource technology 20111101
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A plastidial sodium-dependent pyruvate transporter. Nature 20110824
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Host cholesterol synthesis contributes to growth of intracellular Toxoplasma gondii in macrophages. The Journal of veterinary medical science 20110501
Development of natural anti-tumor drugs by microorganisms. Journal of bioscience and bioengineering 20110501
Statins downregulate K6a promoter activity: a possible therapeutic avenue for pachyonychia congenita. The Journal of investigative dermatology 20110501
N-acetylcysteine and N-nitroarginine methyl ester attenuate Carboplatin-induced ototoxicity in dissociated spiral ganglion neuron cultures. Clinical and experimental otorhinolaryngology 20110301
Statins reduce the androgen sensitivity and cell proliferation by decreasing the androgen receptor protein in prostate cancer cells. The Prostate 20110215
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Statin-induced apoptosis via the suppression of ERK1/2 and Akt activation by inhibition of the geranylgeranyl-pyrophosphate biosynthesis in glioblastoma. Journal of experimental & clinical cancer research : CR 20110101
Conversion of commensal Escherichia coli K-12 to an invasive form via expression of a mutant histone-like protein. mBio 20110101
Pleiotropic effects of statins in distal human pulmonary artery smooth muscle cells. Respiratory research 20110101
Nox2 oxidase activity accounts for the oxidative stress and vasomotor dysfunction in mouse cerebral arteries following ischemic stroke. PloS one 20110101
Lipophilic statins prevent matrix metalloproteinase-mediated cartilage collagen breakdown by inhibiting protein geranylgeranylation. Annals of the rheumatic diseases 20101201
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IL-2 costimulation enables statin-mediated activation of human NK cells, preferentially through a mechanism involving CD56+ dendritic cells. Cancer research 20101201
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Chronic cholesterol depletion using statin impairs the function and dynamics of human serotonin(1A) receptors. Biochemistry 20100706
A novel statin-mediated 'prenylation block-and-release' assay provides insight into the membrane targeting mechanisms of small GTPases. Biochemical and biophysical research communications 20100618
Brain-derived neurotrophic factor controls cannabinoid CB1 receptor function in the striatum. The Journal of neuroscience : the official journal of the Society for Neuroscience 20100616
Severe hypocholesterolaemia is often neglected in haematological malignancies. European journal of cancer (Oxford, England : 1990) 20100601
A historical perspective on the discovery of statins. Proceedings of the Japan Academy. Series B, Physical and biological sciences 20100511
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Effect of simvastatin on culturing of kidney cells from pigs in vitro. Molecular biology reports 20100301
Expression, localization, and pharmacological role of Kv7 potassium channels in skeletal muscle proliferation, differentiation, and survival after myotoxic insults. The Journal of pharmacology and experimental therapeutics 20100301
BMPER is upregulated by statins and modulates endothelial inflammation by intercellular adhesion molecule-1. Arteriosclerosis, thrombosis, and vascular biology 20100301
Cholesterol reduction impairs exocytosis of synaptic vesicles. Journal of cell science 20100215
Farnesyl pyrophosphate inhibits epithelialization and wound healing through the glucocorticoid receptor. The Journal of biological chemistry 20100115
Cytotoxic effects of antipsychotic drugs implicate cholesterol homeostasis as a novel chemotherapeutic target. International journal of cancer 20100101
Requirement for nuclear factor kappa B signalling in the interleukin-1-induced expression of the CCAAT/enhancer binding protein-delta gene in hepatocytes. The international journal of biochemistry & cell biology 20100101
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Compactin production studies using Penicillium brevicompactum under solid-state fermentation conditions. Applied biochemistry and biotechnology 20091101
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Suppression in mevalonate synthesis mediates antitumor effects of combined statin and gamma-tocotrienol treatment. Lipids 20091001
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Application of a 3,3-diphenylpentane skeleton as a multi-template for creation of HMG-CoA reductase inhibitors. Bioorganic & medicinal chemistry letters 20090801
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Statins potentiate the in vitro anti-hepatitis C virus activity of selective hepatitis C virus inhibitors and delay or prevent resistance development. Hepatology (Baltimore, Md.) 20090701
Statins inhibit the growth of variant human embryonic stem cells and cancer cells in vitro but not normal human embryonic stem cells. British journal of pharmacology 20090701
Effect of precultural and nutritional parameters on compactin production by solid-state fermentation. Journal of microbiology and biotechnology 20090701
Reduced expression of the mevalonate pathway enzyme farnesyl pyrophosphate synthase unveils recognition of tumor cells by Vgamma9Vdelta2 T cells. Journal of immunology (Baltimore, Md. : 1950) 20090615
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Combined treatment of gamma-tocotrienol with statins induce mammary tumor cell cycle arrest in G1. Experimental biology and medicine (Maywood, N.J.) 20090601
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A comparison between the effects of hydrophobic and hydrophilic statins on osteoclast function in vitro and ovariectomy-induced bone loss in vivo. Calcified tissue international 20071101
Synergistic activity of the histone deacetylase inhibitor suberoylanilide hydroxamic acid and the bisphosphonate zoledronic acid against prostate cancer cells in vitro. Molecular cancer therapeutics 20071101
Comparative evaluation of the effects of statins on human stem and cancer cells in vitro. Reproductive biomedicine online 20071101
Salicylic acid-induced taxol production and isopentenyl pyrophosphate biosynthesis in suspension cultures of Taxus chinensis var. mairei. Cell biology international 20071001
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Modulation of COX-2 expression by statins in human monocytic cells. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20070601
Asbestos induces nitric oxide synthesis in mesothelioma cells via Rho signaling inhibition. American journal of respiratory cell and molecular biology 20070601
Characterization of Salmonella enterica serovar Typhimurium DT104 invasion in an epithelial cell line (IPEC J2) from porcine small intestine. Veterinary microbiology 20070310
Gamma delta T cells kill myeloma cells by sensing mevalonate metabolites and ICAM-1 molecules on cell surface. Biochemical and biophysical research communications 20070309
Cholesterol-dependent balance between evoked and spontaneous synaptic vesicle recycling. The Journal of physiology 20070301
Analysis of pharmaceuticals in wastewater and removal using a membrane bioreactor. Analytical and bioanalytical chemistry 20070201
Relative activation of human pregnane X receptor versus constitutive androstane receptor defines distinct classes of CYP2B6 and CYP3A4 inducers. The Journal of pharmacology and experimental therapeutics 20070101
The Interleukin-6 inflammation pathway from cholesterol to aging--role of statins, bisphosphonates and plant polyphenols in aging and age-related diseases. Immunity & ageing : I & A 20070101
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Mevastatin increases eNO synthase expression and inhibits lipid peroxidation in human endothelial cells. Clinical hemorheology and microcirculation 20070101
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Characterization of an HMG-CoA reductase from Listeria monocytogenes that exhibits dual coenzyme specificity. Biochemistry 20061205
Cholinesterase inhibitor blockade and its prevention by statins of sympathetic alpha7-nAChR-mediated cerebral nitrergic neurogenic vasodilation. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20061201
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Internal mammary artery smooth muscle cells resist migration and possess high antioxidant capacity. Cardiovascular research 20061001
Mevastatin inhibits proliferation of rat ovarian theca-interstitial cells by blocking the mitogen-activated protein kinase pathway. Fertility and sterility 20061001
The key role of apoptosis in the pathogenesis and treatment of pulmonary hypertension. European journal of cardio-thoracic surgery : official journal of the European Association for Cardio-thoracic Surgery 20060901
Screening of compactin-resistant microorganisms capable of converting compactin to pravastatin. Current microbiology 20060801
Statins revert doxorubicin resistance via nitric oxide in malignant mesothelioma. International journal of cancer 20060701
Statins inhibit growth of human endometrial stromal cells independently of cholesterol availability. Biology of reproduction 20060701
Regulation of de novo phosphatidylinositol synthesis. Journal of lipid research 20060701
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Microsphere-based protease assays and screening application for lethal factor and factor Xa. Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501
Inhibition of protein prenylation by bisphosphonates causes sustained activation of Rac, Cdc42, and Rho GTPases. Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20060501
Involvement of Rho signaling in PAR2-mediated regulation of neutrophil adhesion to lung epithelial cells. European journal of pharmacology 20060424
Pitavastatin effect on ATP binding cassette A1-mediated lipid efflux from macrophages: evidence for liver X receptor (LXR)-dependent and LXR-independent mechanisms of activation by cAMP. The Journal of pharmacology and experimental therapeutics 20060401
HMG-CoA reductase inhibitors induce apoptosis in pericytes. Microvascular research 20060301
Biosynthesis of mono- and sesquiterpenes in strawberry fruits and foliage: 2H labeling studies. Journal of agricultural and food chemistry 20060222
Formal enantioselective synthesis of (+)-compactin. Organic letters 20060216
Activators of the energy sensing kinase AMPK inhibit random cell movement and chemotaxis in U937 cells. Immunology and cell biology 20060201
Alkylamines cause Vgamma9Vdelta2 T-cell activation and proliferation by inhibiting the mevalonate pathway. Blood 20060115
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Statins decrease serotonin-induced contractions in coronary arteries of swine in vitro. Pharmacology 20060101
Pharmacological evidence for activation of phospholipid and small GTP binding protein signalling cascades by Nod factors. Plant physiology and biochemistry : PPB 20060101
Statin-induced expression of CD59 on vascular endothelium in hypoxia: a potential mechanism for the anti-inflammatory actions of statins in rheumatoid arthritis. Arthritis research & therapy 20060101
Statins prevent beta-amyloid inhibition of sympathetic alpha7-nAChR-mediated nitrergic neurogenic dilation in porcine basilar arteries. Journal of cerebral blood flow and metabolism : official journal of the International Society of Cerebral Blood Flow and Metabolism 20051201
Bioactive small molecules reveal antagonism between the integrated stress response and sterol-regulated gene expression. Cell metabolism 20051201
X-Hitting: an algorithm for novelty detection and dereplication by UV spectra of complex mixtures of natural products. Analytical chemistry 20051101
Cholesterol biosynthesis and the pro-apoptotic effects of the p75 nerve growth factor receptor in PC12 pheochromocytoma cells. Brain research. Molecular brain research 20051003
Statins modulate the levels of osteoprotegerin/receptor activator of NFkappaB ligand mRNA in mouse bone-cell cultures. Hormone and metabolic research = Hormon- und Stoffwechselforschung = Hormones et metabolisme 20051001
Structural insights into drug processing by human carboxylesterase 1: tamoxifen, mevastatin, and inhibition by benzil. Journal of molecular biology 20050909
Fast analysis of pravastatin in production media. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050805
Kruppel-like factor 2 as a novel mediator of statin effects in endothelial cells. Circulation 20050802
Genomic effect of vitamin 'C' and statins within human mononuclear cells involved in atherogenic process. European journal of clinical nutrition 20050801
Induction of macrophage elastase (MMP-12) gene expression by statins. Journal of cellular physiology 20050701
Statins prevent oxidized LDL-induced injury of glomerular podocytes by activating the phosphatidylinositol 3-kinase/AKT-signaling pathway. Journal of the American Society of Nephrology : JASN 20050701
In vivo and in vitro effects of statins on lymphocytes in patients with Hashimoto's thyroiditis. European journal of endocrinology 20050701
JBMR anniversary classic. Nitrogen-containing biophosphonates inhibit the mevalonate pathway and prevent post-translational prenylation of GTP-binding proteins, including Ras. Originally published in Volume 7, number 4, pp 581-9 (1998). Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20050701
Cholesterol modulation of the expression of mitochondrial aconitase in human prostatic carcinoma cells. The Chinese journal of physiology 20050630
Regulation of HMG-CoA reductase in MCF-7 cells by genistein, EPA, and DHA, alone and in combination with mevastatin. Cancer letters 20050628
FOXO-dependent expression of the proapoptotic protein Bim: pivotal role for apoptosis signaling in endothelial progenitor cells. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050601
4,8-Dimethyldecanal, the aggregation pheromone of Tribolium castaneum, is biosynthesized through the fatty acid pathway. Journal of chemical ecology 20050601
Novel and simple high-performance liquid chromatographic method for determination of 3-hydroxy-3-methylglutaryl-coenzyme A reductase activity. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20050525
HMG CoA reductase inhibitors (statins) to treat Epstein-Barr virus-driven lymphoma. British journal of cancer 20050509
Interleukin-6 and mevastatin regulate plasminogen activator inhibitor-1 through CCAAT/enhancer-binding protein-delta. Arteriosclerosis, thrombosis, and vascular biology 20050501
Statins potentiate the IFN-gamma-induced upregulation of group IIA phospholipase A2 in human aortic smooth muscle cells and HepG2 hepatoma cells. Biochimica et biophysica acta 20050415
Induction of de novo volatile terpene biosynthesis via cytosolic and plastidial pathways by methyl jasmonate in foliage of Vitis vinifera L. Journal of agricultural and food chemistry 20050406
Effector gammadelta T cells and tumor cells as immune targets of zoledronic acid in multiple myeloma. Leukemia 20050401
Disruption of lipid rafts causes apoptotic cell death in HaCaT keratinocytes. Experimental dermatology 20050401
Progesterone-receptor antagonists and statins decrease de novo cholesterol synthesis and increase apoptosis in rat and human periovulatory granulosa cells in vitro. Biology of reproduction 20050301
A simultaneous assessment of CYP3A4 metabolism and induction in the DPX-2 cell line. The AAPS journal 20050301
Three-dimensional quantitative structure (3-D QSAR) activity relationship studies on imidazolyl and N-pyrrolyl heptenoates as 3-hydroxy-3-methylglutaryl-CoA reductase (HMGR) inhibitors by comparative molecular similarity indices analysis (CoMSIA). Bioorganic & medicinal chemistry letters 20050215
High volume bioassays to assess CYP3A4-mediated drug interactions: induction and inhibition in a single cell line. Drug metabolism and disposition: the biological fate of chemicals 20050101
Inhibitory effects of mevastatin and a geranylgeranyl transferase I inhibitor (GGTI-2166) on mononuclear osteoclast formation induced by receptor activator of NF kappa B ligand (RANKL) or tumor necrosis factor-alpha (TNF-alpha). Biochemical pharmacology 20050101
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