Accession NumberHMDB06740
Common_NameCholesteryl eicosanoic acid
DescriptionCholesteryl eicosanoic acid is a cholesteryl ester. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. Cholesteryl eicosanoic acid has been also found in the umbilical cord and in the content of chalazion (chalazia, also known as a meibomian gland lipogranuloma, is a cyst in the eyelid that is caused by inflammation of a blocked meibomian gland, usually on the upper eyelid). (PMID: 16458590, 9420339, 3343104, 6721900)
Chemical_IUPAC_Name[(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl] icosanoate
Chemical FormulaC47H84O2
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Predicted 1H NMR SpectrumDownload
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Predicted 13C NMR PeaklistDownload
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