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2067-66-5 | 6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-Octacontanonadecaen-1-ol, 3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-eicosamethyl-
CAS No: 2067-66-5 Catalog No: AG002IN6 MDL No:
Product Description
Catalog Number:
AG002IN6
Chemical Name:
6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-Octacontanonadecaen-1-ol, 3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-eicosamethyl-
CAS Number:
2067-66-5
Molecular Formula:
C100H164O
Molecular Weight:
1382.3716
IUPAC Name:
(6E,10E,14E,18E,22Z,26E,30E,34E,38E,42E,46E,50E,54E,58Z,62E,66E,70E,74E)-3,7,11,15,19,23,27,31,35,39,43,47,51,55,59,63,67,71,75,79-icosamethyloctaconta-6,10,14,18,22,26,30,34,38,42,46,50,54,58,62,66,70,74,78-nonadecaen-1-ol
InChI:
InChI=1S/C100H164O/c1-81(2)41-22-42-82(3)43-23-44-83(4)45-24-46-84(5)47-25-48-85(6)49-26-50-86(7)51-27-52-87(8)53-28-54-88(9)55-29-56-89(10)57-30-58-90(11)59-31-60-91(12)61-32-62-92(13)63-33-64-93(14)65-34-66-94(15)67-35-68-95(16)69-36-70-96(17)71-37-72-97(18)73-38-74-98(19)75-39-76-99(20)77-40-78-100(21)79-80-101/h41,43,45,47,49,51,53,55,57,59,61,63,65,67,69,71,73,75,77,100-101H,22-40,42,44,46,48,50,52,54,56,58,60,62,64,66,68,70,72,74,76,78-80H2,1-21H3/b82-43+,83-45+,84-47+,85-49+,86-51-,87-53+,88-55+,89-57+,90-59+,91-61+,92-63+,93-65+,94-67+,95-69-,96-71+,97-73+,98-75+,99-77+
InChI Key:
KEVPZUBEAUSPNJ-OYHKHEHLSA-N
SMILES:
OCCC(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(CCC=C(C)C)C)C)C)C)C)C)C)C)C)C)C)C)C)C)C)C)C)C)C
Properties
Complexity:
2840
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
18
Exact Mass:
1382.282g/mol
Formal Charge:
0
Heavy Atom Count:
101
Hydrogen Bond Acceptor Count:
1
Hydrogen Bond Donor Count:
1
Isotope Atom Count:
0
Molecular Weight:
1382.411g/mol
Monoisotopic Mass:
1381.278g/mol
Rotatable Bond Count:
59
Topological Polar Surface Area:
20.2A^2
Undefined Atom Stereocenter Count:
1
Undefined Bond Stereocenter Count:
0
XLogP3:
36.6
Literature
| Title | Journal |
|---|---|
| Heritable disorders in the metabolism of the dolichols: A bridge from sterol biosynthesis to molecular glycosylation. | American journal of medical genetics. Part C, Seminars in medical genetics 20121115 |
| Influence of liver-X-receptor on tissue cholesterol, coenzyme Q and dolichol content. | Molecular membrane biology 20121101 |
| Glycosylation defects underlying fetal alcohol spectrum disorder: a novel pathogenetic model. 'When the wine goes in, strange things come out' - S.T. Coleridge, The Piccolomini. | Journal of inherited metabolic disease 20120501 |
| Isomeric analysis of oligomannosidic N-glycans and their dolichol-linked precursors. | Glycobiology 20120301 |
| 5-thiomannosides block the biosynthesis of dolichol-linked oligosaccharides and mimic class I congenital disorders of glycosylation. | Chembiochem : a European journal of chemical biology 20120213 |
| Liquid chromatography/tandem mass spectrometry of dolichols and polyprenols, lipid sugar carriers across evolution. | Biochimica et biophysica acta 20111101 |
| From glycosylation disorders to dolichol biosynthesis defects: a new class of metabolic diseases. | Journal of inherited metabolic disease 20110801 |
| Isoprenoid biosynthesis in the erythrocytic stages of Plasmodium falciparum. | Memorias do Instituto Oswaldo Cruz 20110801 |
| Nogo-B receptor is necessary for cellular dolichol biosynthesis and protein N-glycosylation. | The EMBO journal 20110615 |
| Polyisoprenoids - Secondary metabolites or physiologically important superlipids? | Biochemical and biophysical research communications 20110422 |
| Improvement of dolichol-linked oligosaccharide biosynthesis by the squalene synthase inhibitor zaragozic acid. | The Journal of biological chemistry 20110225 |
| Glycoprotein maturation and the UPR. | Methods in enzymology 20110101 |
| A novel cerebello-ocular syndrome with abnormal glycosylation due to abnormalities in dolichol metabolism. | Brain : a journal of neurology 20101101 |
| Defect in dolichol-dependent glycosylation increases sensitivity of Saccharomyces cerevisiae towards anti-fungal drugs. | Yeast (Chichester, England) 20100801 |
| SRD5A3 is required for converting polyprenol to dolichol and is mutated in a congenital glycosylation disorder. | Cell 20100723 |
| Molecular characterization of the cis-prenyltransferase of Giardia lamblia. | Glycobiology 20100701 |
| [Biomarkers of alcohol abuse. Part II. New biomarkers and their interpretation]. | Psychiatria polska 20100101 |
| Separation of hydrophobic metabolites using monolithic silica column in high-performance liquid chromatography and supercritical fluid chromatography. | Journal of separation science 20090801 |
| Biochemical characterization and membrane topology of Alg2 from Saccharomyces cerevisiae as a bifunctional alpha1,3- and 1,6-mannosyltransferase involved in lipid-linked oligosaccharide biosynthesis. | The Journal of biological chemistry 20090501 |
| Characterization of dehydrodolichyl diphosphate synthase gene in rainbow trout (Oncorhynchus mykiss). | Comparative biochemistry and physiology. Part B, Biochemistry & molecular biology 20090301 |
| Quantification of dolichol in the human lens with different types of cataracts. | Molecular vision 20090101 |
| Regulation of sterol transport between membranes and NPC2. | Biochemistry 20081021 |
| Rsp5p ubiquitin ligase and the transcriptional activators Spt23p and Mga2p are involved in co-regulation of biosynthesis of end products of the mevalonate pathway and triacylglycerol in yeast Saccharomyces cerevisiae. | Biochimica et biophysica acta 20081001 |
| Contribution of the mevalonate and methylerythritol phosphate pathways to the biosynthesis of dolichols in plants. | The Journal of biological chemistry 20080725 |
| Leishmania amazonensis: biosynthesis of polyprenols of 9 isoprene units by amastigotes. | Experimental parasitology 20080401 |
| Distribution of dolichol in the serum and relationships between serum dolichol levels and various laboratory test values. | Biological & pharmaceutical bulletin 20080301 |
| Polyisoprenol specificity in the Campylobacter jejuni N-linked glycosylation pathway. | Biochemistry 20071218 |
| Effects of oxidative stress on the Dolichol content of isolated rat liver cells. | Free radical research 20071101 |
| Deletion of a single mevalonate kinase (Mvk) allele yields a murine model of hyper-IgD syndrome. | Journal of inherited metabolic disease 20071101 |
| The farnesyl-diphosphate/geranylgeranyl-diphosphate synthase of Toxoplasma gondii is a bifunctional enzyme and a molecular target of bisphosphonates. | The Journal of biological chemistry 20071019 |
| Lovastatin suppresses erythropoietin receptor surface expression through dual inhibition of glycosylation and geranylgeranylation. | Biochemical pharmacology 20070815 |
| Identification and quantification of dolichol and dolichoic acid in neuromelanin from substantia nigra of the human brain. | Journal of lipid research 20070701 |
| Defect in fatty acid esterification of dolichol in Niemann-Pick type C1 mouse livers in vivo. | Biochimica et biophysica acta 20070401 |
| Dissecting the role of dolichol in cell wall assembly in the yeast mutants impaired in early glycosylation reactions. | Yeast (Chichester, England) 20070401 |
| Generation of reactive oxygen species is an early event in dolichyl phosphate-induced apoptosis. | Journal of cellular biochemistry 20070201 |
| Analysis of ubiquinones, dolichols, and dolichol diphosphate-oligosaccharides by liquid chromatography-electrospray ionization-mass spectrometry. | Methods in enzymology 20070101 |
| Lipid content determines aggregation of neuromelanin granules in vitro. | Journal of neural transmission. Supplementum 20070101 |
| Increased nonsterol isoprenoids, dolichol and ubiquinone, in the Smith-Lemli-Opitz syndrome: effects of dietary cholesterol. | Journal of lipid research 20061201 |
| Protein dolichylation in Plasmodium falciparum. | FEBS letters 20061127 |
| In vitro evidence for the dual function of Alg2 and Alg11: essential mannosyltransferases in N-linked glycoprotein biosynthesis. | Biochemistry 20060808 |
| Overexpression of the Saccharomyces cerevisiae RER2 gene in Trichoderma reesei affects dolichol dependent enzymes and protein glycosylation. | Fungal genetics and biology : FG & B 20060601 |
| Activity of Pichia pastoris alternative cis-prenyltransferase is correlated with proliferation of peroxisomes. | Cell biology international 20060201 |
| Interplay between the cis-prenyltransferases and polyprenol reductase in the yeast Saccharomyces cerevisiae. | Biochimie 20060101 |
| Application of fluorophore-assisted carbohydrate electrophoresis for the study of the dolichol pyrophosphate-linked oligosaccharides pathway in cell cultures and animal tissues. | Methods in molecular biology (Clifton, N.J.) 20060101 |
| Controlling N-linked glycan site occupancy. | Biochimica et biophysica acta 20051115 |
| Separation of polyprenol and dolichol by monolithic silica capillary column chromatography. | Journal of lipid research 20051001 |
| NMR studies on how the binding complex of polyisoprenol recognition sequence peptides and polyisoprenols can modulate membrane structure. | Current protein & peptide science 20051001 |
| Polyisoprenoids: structure, biosynthesis and function. | Progress in lipid research 20050701 |
| Polyprenyl lipid synthesis in mammalian cells expressing human cis-prenyl transferase. | Biochemical and biophysical research communications 20050603 |
| Dolichol is the major lipid component of human substantia nigra neuromelanin. | Journal of neurochemistry 20050201 |
| Chronic high doses of thioacetamide followed by vitamin A modify dolichol, dolichol isoprenoids, and retinol content in rat liver cells. | Drug and chemical toxicology 20050101 |
| Functional relationships between the Saccharomyces cerevisiae cis-prenyltransferases required for dolichol biosynthesis. | Acta biochimica Polonica 20050101 |
| Dolichols of the fern Matteucia struthiopteris. | Acta biochimica Polonica 20050101 |
| The methylerythritol phosphate pathway is functionally active in all intraerythrocytic stages of Plasmodium falciparum. | The Journal of biological chemistry 20041210 |
| Effect of a load of Vitamin A after acute thioacetamide intoxication on dolichol, dolichol isoprenoids and retinol content in isolated rat liver cells. | Toxicology 20040701 |
| Anti-aging effects of anti-lipolytic drugs. | Experimental gerontology 20040701 |
| Defects in the N-linked oligosaccharide biosynthetic pathway in a Trypanosoma brucei glycosylation mutant. | Eukaryotic cell 20040401 |
| Ageing and oxidative stress: a role for dolichol in the antioxidant machinery of cell membranes? | Journal of Alzheimer's disease : JAD 20040401 |
| Association of thioacetamide and ethanol treatment: dolichol and retinol in isolated rat liver cells. | Drug and chemical toxicology 20040201 |
| Familial hypothalamic digoxin deficiency syndrome. | The Journal of neuropsychiatry and clinical neurosciences 20040101 |
| Changes in dolichol and pentosidine levels in the age-mismatched heterotopically transplanted rat heart. | Biogerontology 20040101 |
| Schizoid neurochemical pathology-induced membrane Na(+)-K+ ATPase inhibition in relation to neurological disorders. | The International journal of neuroscience 20031201 |
| Hypothalamic digoxin, hemispheric chemical dominance, and oncogenesis: evidence from multiple myeloma. | The International journal of neuroscience 20031201 |
| Hypothalamic digoxin, hemispheric chemical dominance, and mesenteric artery occlusion. | The International journal of neuroscience 20031201 |
| A hypothalamic digoxin-mediated model for autism. | The International journal of neuroscience 20031101 |
| Hypothalamic-mediated model for systemic lupus erythematosis: relation to hemispheric chemical dominance. | The International journal of neuroscience 20031101 |
| Isoprenoid pathway-related membrane dysfunction in neuropsychiatric disorders. | The International journal of neuroscience 20031101 |
| Hypothalamic digoxin, hemispheric chemical dominance, and sarcoidosis. | The International journal of neuroscience 20031101 |
| Hypothalamic digoxin, hemispheric chemical dominance, and peptic ulcer disease. | The International journal of neuroscience 20031001 |
| Hypothalamic digoxin, hemispheric chemical dominance, and interstitial lung disease. | The International journal of neuroscience 20031001 |
| Hypothalamic digoxin, hemispheric chemical dominance, and inflammatory bowel disease. | The International journal of neuroscience 20030901 |
| Hypothalamic digoxin, hemispheric chemical dominance, and chronic bronchitis emphysema. | The International journal of neuroscience 20030901 |
| Endogenous hypodigoxinemia-related immune deficiency syndrome. | The International journal of neuroscience 20030901 |
| Effects of peroxisome proliferators gemfibrozil and clofibrate on syntheses of dolichol and cholesterol in rat liver. | Journal of biochemistry 20030801 |
| The concept of cerebral chemical dominance. | The International journal of neuroscience 20030701 |
| Hypothalamic-mediated model for Creutzfeldt-Jakob disease: relation to hemispheric chemical dominance. | The International journal of neuroscience 20030701 |
| Hypothalamic digoxin, hemispheric dominance, and family bonding behavior. | The International journal of neuroscience 20030701 |
| Hypothalamic digoxin, cerebral chemical dominance, and calcium/magnesium metabolism. | The International journal of neuroscience 20030701 |
| A new type of congenital disorders of glycosylation (CDG-Ii) provides new insights into the early steps of dolichol-linked oligosaccharide biosynthesis. | The Journal of biological chemistry 20030620 |
| Hypothalamic digoxin and hemispheric chemical dominance: relation to speech and language dysfunction. | The International journal of neuroscience 20030601 |
| Hypothalamic digoxin, regulation of neuronal transmission, and cerebral dominance. | The International journal of neuroscience 20030601 |
| Overexpression of GDP-mannose pyrophosphorylase in Saccharomyces cerevisiae corrects defects in dolichol-linked saccharide formation and protein glycosylation. | Biochimica et biophysica acta 20030407 |
| Hypothalamic digoxin-mediated model for Parkinson's disease. | The International journal of neuroscience 20030401 |
| Hypothalamic digoxin and isoprenoid pathway dysfunction relation to alcoholic addiction, alcoholic cirrhosis, and acquired hepatocerebral degeneration--relation to hemispheric chemical dominance. | The International journal of neuroscience 20030401 |
| Hypothalamic digoxin and hemispheric chemical dominance--relation to the pathogenesis of senile osteoporosis, degenerative osteoarthritis, and spondylosis. | The International journal of neuroscience 20030301 |
| Hypothalamic digoxin, hemispheric chemical dominance, and Alzheimer's disease. | The International journal of neuroscience 20030301 |
| Involvement of retinoid X receptor alpha in coenzyme Q metabolism. | Journal of molecular biology 20030221 |
| Chronic ethanol treatment: dolichol and retinol distribution in isolated rat liver cells. | Free radical biology & medicine 20030201 |
| Characterization by NMR and molecular modeling of the binding of polyisoprenols and polyisoprenyl recognition sequence peptides: 3D structure of the complexes reveals sites of specific interactions. | Glycobiology 20030201 |
| Hypothalamic digoxin, cerebral chemical dominance, and pathogenesis of pulmonary diseases. | The International journal of neuroscience 20030201 |
| Isoprenoid pathway dysfunction in human male infertility. | Archives of andrology 20030101 |
| The age-related accumulation of dolichol in rat liver may correlate with expectation of life. | Biogerontology 20030101 |
| Isoprenoid pathway related cascade in multiple myeloma. | Pathology oncology research : POR 20030101 |
| Hypothalamic digoxin-mediated model for trisomy 21. | Pediatric pathology & molecular medicine 20030101 |
| The isoprenoid pathway and the pathogenesis of Reye's syndrome. | Pediatric pathology & molecular medicine 20030101 |
| [Dolichols--long-chain isoprenoid lipids required for protein modification]. | Postepy biochemii 20030101 |
| The fate of dolichol in rat cells and tissues. | Biogerontology 20030101 |
| New perspectives for (S)-dolichol and (S)- nor dolichol synthesis and biological functions. | Biogerontology 20030101 |
| The effect of carbon tetrachloride and ultraviolet radiation on dolichol levels in liver cells isolated from 3- and 24-month-old male Sprague-Dawley rats. | Biogerontology 20030101 |
| Age-related changes of isoprenoid biosynthesis in rat liver and brain. | Biogerontology 20030101 |
| Dolichol: a solar filter with UV-absorbing properties which can be photoenhanced. | Biogerontology 20030101 |
| Coupling of the dolichol-P-P-oligosaccharide pathway to translation by perturbation-sensitive regulation of the initiating enzyme, GlcNAc-1-P transferase. | The Journal of biological chemistry 20021018 |
| Influence of chronic ethanol consumption on toxic effects of 1,2-dichloroethane: glycolipoprotein retention and impairment of dolichol concentration in rat liver microsomes and Golgi apparatus. | Toxicology 20020916 |
| Expression and characterization of a human cDNA that complements the temperature-sensitive defect in dolichol kinase activity in the yeast sec59-1 mutant: the enzymatic phosphorylation of dolichol and diacylglycerol are catalyzed by separate CTP-mediated kinase activities in Saccharomyces cerevisiae. | Glycobiology 20020901 |
| Familial hypodigoxinemic membrane Na(+)-K(+) ATPase upregulatory syndrome - relation between digoxin status and cerebral dominance. | Neurology India 20020901 |
| Thioacetamide impairs retinol storage and dolichol content in rat liver cells in vivo. | Biochimica et biophysica acta 20020808 |
| Hypothalamic digoxin-mediated model for subacute sclerosing panencephalitis. | Journal of neurovirology 20020801 |
| Dolichol biosynthesis in the yeast Saccharomyces cerevisiae: an insight into the regulatory role of farnesyl diphosphate synthase. | FEMS yeast research 20020801 |
| Dolichol content in isolated sinusoidal liver cells after in vivo chronic treatment with thioacetamide. | Experimental and toxicologic pathology : official journal of the Gesellschaft fur Toxikologische Pathologie 20020701 |
| Hypothalamic digoxin deficiency in obsessive compulsive disorder and la Tourette's syndrome. | The International journal of neuroscience 20020701 |
| Transmembrane movement of dolichol linked carbohydrates during N-glycoprotein biosynthesis in the endoplasmic reticulum. | Seminars in cell & developmental biology 20020601 |
| Age-related changes of cholesterol and dolichol biosynthesis in rat liver. | Mechanisms of ageing and development 20020430 |
| Hypothalamic digoxin, hemispheric dominance, and neuroimmune integration. | The International journal of neuroscience 20020401 |
| Induction of the synthesis of an additional family of long-chain dolichols in the yeast Saccharomyces cerevisiae. Effect of starvation and ageing. | Acta biochimica Polonica 20020101 |
| Effects of ageing and increased haemolysis on the levels of dolichol in rat spleen. | Experimental gerontology 20011201 |
| Hypothalamic digoxin mediated model for oncogenesis. | Journal of experimental & clinical cancer research : CR 20011201 |
| Allosteric regulation provides a molecular mechanism for preferential utilization of the fully assembled dolichol-linked oligosaccharide by the yeast oligosaccharyltransferase. | Biochemistry 20011009 |
| Substrate specificity of the glycosyl donor for oligosaccharyl transferase. | The Journal of organic chemistry 20010921 |
| Yeast Saccharomyces cerevisiae has two cis-prenyltransferases with different properties and localizations. Implication for their distinct physiological roles in dolichol synthesis. | Genes to cells : devoted to molecular & cellular mechanisms 20010601 |
| Plasmodium falciparum: the lethal effects of tunicamycin and mevastatin on the parasite are not mediated by the inhibition of N-linked oligosaccharide biosynthesis. | Experimental parasitology 20010601 |
| A novel family of longer chain length dolichols present in oleate-induced yeast Saccharomyces cerevisiae. | Biochimie 20010501 |
| Substrate specificity of N-acetylglucosaminyl(diphosphodolichol) N-acetylglucosaminyl transferase, a key enzyme in the dolichol pathway. | Bioorganic & medicinal chemistry 20010501 |
| Large-scale isolation of dolichol-linked oligosaccharides with homogeneous oligosaccharide structures: determination of steady-state dolichol-linked oligosaccharide compositions. | Glycobiology 20010401 |
| Study on the biosynthesis of dolichol in yeast: recognition of the prenyl chain length in polyprenol reduction. | Journal of biochemistry 20010201 |
| Stimulation of acid sphingomyelinase activity by lysosomal lipids and sphingolipid activator proteins. | Biological chemistry 20010201 |
| Suppression of dolichol synthesis with isoprenoids and statins may potentiate the cancer-retardant efficacy of IGF-I down-regulation. | Medical hypotheses 20010101 |
| An alternative cis-isoprenyltransferase activity in yeast that produces polyisoprenols with chain lengths similar to mammalian dolichols. | Glycobiology 20010101 |
| Interaction between monensin and CCl4 after chronic treatment: dolichol and retinol content of rat liver sinusoidal cells. | International journal of tissue reactions 20010101 |
| The isoprenoid pathway in lone atrial fibrillation with embolic stroke. | Indian heart journal 20010101 |
| Activation of IP(3)-protein kinase C-alpha signal transduction pathway precedes the changes of plasma cholesterol, hepatic lipid metabolism and induction of low-density lipoprotein receptor expression in 17-beta-oestradiol-treated rats. | Experimental physiology 20010101 |
| A hypothalamic digoxin mediated model for conscious and subliminal perception. | Journal of neural transmission (Vienna, Austria : 1996) 20010101 |
| [Synthesis of dolicyl- and polyprenyl sulfates]. | Bioorganicheskaia khimiia 20010101 |
| Hypothalamic digoxin, hemispheric dominance and the acquired immunodeficiency syndrome. | Neuroimmunomodulation 20010101 |
| Influence of peroxisome proliferator-activated receptor alpha on ubiquinone biosynthesis. | Journal of molecular biology 20000331 |
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