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142561-96-4,MFCD00868072
Catalog No.:AA009GV1

142561-96-4 | ZARAGOZIC ACID A

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1mg
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA009GV1
Chemical Name:
ZARAGOZIC ACID A
CAS Number:
142561-96-4
Molecular Formula:
C35H46O14
Molecular Weight:
690.7313
MDL Number:
MFCD00868072
SMILES:
CC[C@@H](C[C@@H](/C=C/C(=O)O[C@@H]1[C@@H](O)[C@@]2(O[C@@]1(C(=O)O)[C@](O)(C(=O)O)[C@H](O2)C(=O)O)CCC(=C)[C@H]([C@@H](Cc1ccccc1)C)OC(=O)C)C)C
Properties
Computed Properties
 
Complexity:
1290  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
10  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
49  
Hydrogen Bond Acceptor Count:
14  
Hydrogen Bond Donor Count:
5  
Rotatable Bond Count:
19  
XLogP3:
4.9  

Literature

Title: Differential Regulation of Gene Expression by Cholesterol Biosynthesis Inhibitors That Reduce (Pravastatin) or Enhance (Squalestatin 1) Nonsterol Isoprenoid Levels in Primary Cultured Mouse and Rat Hepatocytes.

Journal: The Journal of pharmacology and experimental therapeutics 20160801

Title: Critical time window of neuronal cholesterol synthesis during neurite outgrowth.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 20120530

Title: Binding modes of zaragozic acid A to human squalene synthase and staphylococcal dehydrosqualene synthase.

Journal: The Journal of biological chemistry 20120525

Title: Effects of farnesyl pyrophosphate accumulation on calvarial osteoblast differentiation.

Journal: Endocrinology 20110801

Title: Prevention of transplant coronary artery disease by prenylation inhibitors.

Journal: The Journal of heart and lung transplantation : the official publication of the International Society for Heart Transplantation 20110701

Title: Inhibition of the isoprenoid biosynthesis pathway; detection of intermediates by UPLC-MS/MS.

Journal: Biochimica et biophysica acta 20110401

Title: A general access to zaragozic acids: total synthesis and structure elucidation of zaragozic acid D and formal syntheses of zaragozic acids A and C.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20110314

Title: Improvement of dolichol-linked oligosaccharide biosynthesis by the squalene synthase inhibitor zaragozic acid.

Journal: The Journal of biological chemistry 20110225

Title: Activation of PPAR-γ and PTEN cascade participates in lovastatin-mediated accelerated differentiation of oligodendrocyte progenitor cells.

Journal: Glia 20101101

Title: Molecular docking studies to map the binding site of squalene synthase inhibitors on dehydrosqualene synthase of Staphylococcus aureus.

Journal: Journal of biomolecular structure & dynamics 20101001

Title: 4-Nitrobenzoate inhibits coenzyme Q biosynthesis in mammalian cell cultures.

Journal: Nature chemical biology 20100701

Title: Cholesterol reduction impairs exocytosis of synaptic vesicles.

Journal: Journal of cell science 20100215

Title: Farnesyl pyrophosphate inhibits epithelialization and wound healing through the glucocorticoid receptor.

Journal: The Journal of biological chemistry 20100115

Title: Statins and the squalene synthase inhibitor zaragozic acid stimulate the non-amyloidogenic pathway of amyloid-beta protein precursor processing by suppression of cholesterol synthesis.

Journal: Journal of Alzheimer's disease : JAD 20100101

Title: Cholesterol biosynthesis modulation regulates dengue viral replication.

Journal: Virology 20090620

Title: Raft nanodomains contribute to Akt/PKB plasma membrane recruitment and activation.

Journal: Nature chemical biology 20080901

Title: Inhibition of squalene synthase upregulates PCSK9 expression in rat liver.

Journal: Archives of biochemistry and biophysics 20080215

Title: The ergosterol biosynthesis inhibitor zaragozic acid promotes vacuolar degradation of the tryptophan permease Tat2p in yeast.

Journal: Biochimica et biophysica acta 20070701

Title: Squalene synthase, a determinant of Raft-associated cholesterol and modulator of cancer cell proliferation.

Journal: The Journal of biological chemistry 20070629

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: Squalestatin alters the intracellular trafficking of a neurotoxic prion peptide.

Journal: BMC neuroscience 20070101

Title: Total syntheses of zaragozic acids A and C by a carbonyl ylide cycloaddition strategy.

Journal: Chemistry (Weinheim an der Bergstrasse, Germany) 20061204

Title: Manipulation of isoprenoid biosynthesis as a possible therapeutic option in mevalonate kinase deficiency.

Journal: Arthritis and rheumatism 20060701

Title: INSIG: a broadly conserved transmembrane chaperone for sterol-sensing domain proteins.

Journal: The EMBO journal 20051116

Title: Species-specific mechanisms for cholesterol 7alpha-hydroxylase (CYP7A1) regulation by drugs and bile acids.

Journal: Archives of biochemistry and biophysics 20050201

Title: Simultaneous determination of farnesyl and geranylgeranyl pyrophosphate levels in cultured cells.

Journal: Analytical biochemistry 20050101

Title: Statin inhibition of Fc receptor-mediated phagocytosis by macrophages is modulated by cell activation and cholesterol.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20041101

Title: Squalestatin cures prion-infected neurons and protects against prion neurotoxicity.

Journal: The Journal of biological chemistry 20040409

Title: Cholesterol-modulating agents kill acute myeloid leukemia cells and sensitize them to therapeutics by blocking adaptive cholesterol responses.

Journal: Blood 20030501

Title: Squalestatin 1-inducible expression of rat CYP2B: evidence that an endogenous isoprenoid is an activator of the constitutive androstane receptor.

Journal: Molecular pharmacology 20021101

Title: Inhibition of squalene synthase and squalene epoxidase in tobacco cells triggers an up-regulation of 3-hydroxy-3-methylglutaryl coenzyme a reductase.

Journal: Plant physiology 20020901

Title: Novel approach to the zaragozic acids. Enantioselective total synthesis of 6,7-dideoxysqualestatin H5.

Journal: The Journal of organic chemistry 20020614

Title: Regulation of oxysterol 7alpha-hydroxylase (CYP7B1) in primary cultures of rat hepatocytes.

Journal: Hepatology (Baltimore, Md.) 20020601

Title: Modeling of binding modes and inhibition mechanism of some natural ligands of farnesyl transferase using molecular docking.

Journal: Journal of medicinal chemistry 20020328

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

Journal: Biochemical and biophysical research communications 20020222

Title: Rapid synthesis of the 7-deoxy zaragozic acid core.

Journal: Organic letters 20020124

Title: Inhibitors of sterol biosynthesis and amphotericin B reduce the viability of pneumocystis carinii f. sp. carinii.

Journal: Antimicrobial agents and chemotherapy 20000601

Title: Truncation of human squalene synthase yields active, crystallizable protein.

Journal: Archives of biochemistry and biophysics 19980215

Title: Expression, purification, and characterization of the human squalene synthase: use of yeast and baculoviral systems.

Journal: Archives of biochemistry and biophysics 19950201

Title: Structure-activity relationships of C1 and C6 side chains of zaragozic acid A derivatives.

Journal: Journal of medicinal chemistry 19941111

Title: Zaragozic acids: a family of fungal metabolites that are picomolar competitive inhibitors of squalene synthase.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19930101

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