1.0 2011-09-21 00:32:44 UTC 2015-07-21 06:57:48 UTC FDB023636 CE(20:1(11Z)) CE(20:1(11Z)) is a cholesterol fatty acid ester or simply a cholesterol ester (CE). Cholesterol esters are cholesterol molecules with long-chain fatty acids linked to the hydroxyl group. They are much less polar than free cholesterol and appear to be the preferred form for transport in plasma and for storage. Cholesterol esters do not contribute to membranes but are packed into intracellular lipid particles or lipoprotein particles. Because of the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of C18 fatty acids. Cholesterol esters are major constituents of the adrenal glands and they also accumulate in the fatty lesions of atherosclerotic plaques. Cholesterol esters are also major constituents of the lipoprotein particles carried in blood (HDL, LDL, VLDL). The cholesterol esters in high-density lipoproteins (HDL) are synthesized largely by transfer of fatty acids to cholesterol from position sn-2 (or C-2) of phosphatidylcholine catalyzed by the enzyme lecithin cholesterol acyl transferase (LCAT). The enzyme also promotes the transfer of cholesterol from cells to HDL. As cholesterol esters accumulate in the lipoprotein core, cholesterol is removed from its surface thus promoting the flow of cholesterol from cell membranes into HDL. This in turn leads to morphological changes in HDL, which grow and become spherical. Subsequently, cholesterol esters are transferred to the other lipoprotein fractions LDL and VLDL, a reaction catalyzed by cholesteryl ester transfer protein. Another enzyme, acyl-CoA:cholesterol acyltransferase (ACAT) synthesizes cholesterol esters from CoA esters of fatty acids and cholesterol. Cholesterol ester hydrolases liberate cholesterol and free fatty acids when required for membrane and lipoprotein formation, and they also provide cholesterol for hormone synthesis in adrenal cells. Cholesteryl eicosapentaenoic acid is a cholesteryl ester. A cholesteryl ester is an ester of cholesterol. Fatty acid esters of cholesterol constitute about two-thirds of the cholesterol in the plasma. Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. The accumulation of cholesterol esters in the arterial intima (the innermost layer of an artery, in direct contact with the flowing blood) is a characteristic feature of atherosclerosis. Atherosclerosis is a disease affecting arterial blood vessels. It is a chronic inflammatory response in the walls of arteries, in large part to the deposition of lipoproteins (plasma proteins that carry cholesterol and triglycerides). In patients with triglyceride levels above 500 mg/dl, approximately 4 g/day of eicosapentaenoic acid reduces triglyceride levels 45% and very low-density lipoprotein cholesterol levels by more than 50%. Physical exercise and fish oil (a rich source of eicosapentaenoic acid) suppress the activity of endothelial lipase (EL) and this, in turn, enhances the plasma concentrations of HDL cholesterol. EL has been shown to have a significant role in modulating the concentrations of plasma HDL. (PMID: 17461707, 15664301, 15524182, 15485592) [HMDB] 1-(11-eicosenoate 1-(11-eicosenoic acid 1-(11-eicosenoic acid) 1-(11-eicosenoyl)-cholesterol 1-eicosenoyl-cholesterol 20:1 Cholesterol ester 20:1(11Z) cholesterol ester CE(20:1) CE(20:1/0:0) CE(20:1n9/0:0) CE(20:1w9/0:0) cholest-5-en-3beta-yl (11Z-eicosenoate cholest-5-en-3beta-yl (11Z-eicosenoate) cholest-5-en-3beta-yl (11Z-eicosenoic acid cholest-5-en-3beta-yl 11Z-eicosenoate cholest-5-en-3beta-yl 11Z-eicosenoic acid cholesterol 1-(11-eicosenoate cholesterol 1-(11-eicosenoate) cholesterol 1-(11-eicosenoic acid cholesterol 1-(11-eicosenoic acid) cholesterol 1-eicosenoate cholesterol 1-eicosenoic acid Cholesterol Ester(20:1) Cholesterol Ester(20:1/0:0) Cholesterol Ester(20:1n9/0:0) Cholesterol Ester(20:1w9/0:0) cholesteryl cholesteryl 1-(11-eicosenoate cholesteryl 1-(11-eicosenoate) cholesteryl 1-(11-eicosenoic acid cholesteryl 1-eicosenoate cholesteryl 1-eicosenoic acid Cholesteryl eicosenoate Cholesteryl eicosenoic acid C47H82O2 679.1528 678.631481868 (2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl icos-11-enoate (2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl icos-11-enoate 70832-37-0 [H][C@@](C)(CCCC(C)C)C1CCC2C3CC=C4C[C@]([H])(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCCCCCCCCC=CCCCCCCCC InChI=1S/C47H82O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h14-15,28,37-38,40-44H,7-13,16-27,29-36H2,1-6H3/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1 OWTYWMJVQZQWFH-YEYBIBAWSA-N belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety. Cholesteryl esters Organic compounds Lipids and lipid-like molecules Steroids and steroid derivatives Steroid esters Aliphatic homopolycyclic compounds Carbonyl compounds Carboxylic acid esters Cholesterols and derivatives Delta-5-steroids Hydrocarbon derivatives Monocarboxylic acids and derivatives Organic oxides Aliphatic homopolycyclic compound Carbonyl group Carboxylic acid derivative Carboxylic acid ester Cholestane-skeleton Cholesterol Cholesteryl ester Delta-5-steroid Hydrocarbon derivative Monocarboxylic acid or derivatives Organic oxide Organic oxygen compound Organooxygen compound Solid logp 10.91 ALOGPS logs -8.03 ALOGPS solubility 6.40e-06 g/l ALOGPS logp 15.45 ChemAxon pka_strongest_basic -7 ChemAxon iupac (2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl icos-11-enoate ChemAxon average_mass 679.1528 ChemAxon mono_mass 678.631481868 ChemAxon smiles [H][C@@](C)(CCCC(C)C)C1CCC2C3CC=C4C[C@]([H])(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCCCCCCCCC=CCCCCCCCC ChemAxon formula C47H82O2 ChemAxon inchi InChI=1S/C47H82O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-27-45(48)49-40-32-34-46(5)39(36-40)28-29-41-43-31-30-42(38(4)26-24-25-37(2)3)47(43,6)35-33-44(41)46/h14-15,28,37-38,40-44H,7-13,16-27,29-36H2,1-6H3/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1 ChemAxon inchikey OWTYWMJVQZQWFH-YEYBIBAWSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 213.73 ChemAxon polarizability 91.11 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB05193 #<Reference:0x000055ce31ceeac8> #<Reference:0x000055ce31cee910> #<Reference:0x000055ce31cee758> #<Reference:0x000055ce31cee5a0> Almond Type 1 specific Prunus dulcis 3755 0.037 0.037 0.037 mg/100 g Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Broccoli Type 1 specific Brassica oleracea var. italica 36774 0.0 0.0 0.0 mg/100 g Buffalo Type 1 specific Bubalus bubalis 89462 Canola Type 2 specific 138011 0.49 0.49 0.49 mg/100 g Canola oil Type 2 0.49 0.49 0.49 mg/100 g Carrot Type 1 specific Daucus carota ssp. sativus 79200 0.0 0.0 0.0 mg/100 g Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Cheddar Cheese Type 2 Cheddar Cheese 0.064 0.064 0.064 mg/100 g Cheese Type 2 specific 0.06 0.06 0.06 mg/100 g Chicken Type 1 specific Gallus gallus 9031 0.018 0.018 0.018 mg/100 g Coconut oil Type 2 0.041 0.041 0.041 mg/100 g Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Corn oil Type 2 0.0505 0.0505 0.0505 mg/100 g Cottage cheese Type 2 0.003 0.003 0.003 mg/100 g Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Haddock Type 1 specific Melanogrammus aeglefinus 8056 0.005 0.005 0.005 mg/100 g Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mozzarella cheese Type 2 0.038 0.038 0.038 mg/100 g Mule deer Type 1 specific Odocoileus 9871 Nectarine Type 1 specific Prunus persica var. nucipersica 323851 0.0 0.0 0.0 mg/100 g Norway haddock Type 1 specific Sebastes viviparus 394708 0.005 0.005 0.005 mg/100 g Olive Type 1 specific Olea europaea 4146 0.0045 0.0045 0.0045 mg/100 g Olive oil Type 2 0.0625 0.0625 0.0625 mg/100 g Ostrich Type 1 specific Struthio camelus 8801 Parmesan cheese Type 2 0.05 0.05 0.05 mg/100 g Pheasant Type 1 specific Phasianus colchicus 9054 Pollock Type 1 specific Pollachius 8059 0.01 0.01 0.01 mg/100 g Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rice Type 1 specific Oryza sativa 4530 0.006 0.006 0.006 mg/100 g Rock ptarmigan Type 1 specific Lagopus muta 64668 Rye bread Type 2 specific 0.017 0.017 0.017 mg/100 g Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Swiss cheese Type 2 0.06 0.06 0.06 mg/100 g Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 White bread Type 1 0.011 0.011 0.011 mg/100 g Wild boar Type 1 specific Sus scrofa 9823 Wild carrot Type 1 specific Daucus carota 4039 0.0 0.0 0.0 mg/100 g Liver carboxylesterase 1 P23141 CES1 Lysosomal acid lipase/cholesteryl ester hydrolase P38571 LIPA Neutral cholesterol ester hydrolase 1 Q6PIU2 NCEH1 Phosphatidylcholine-sterol acyltransferase P04180 LCAT Scavenger receptor class B member 1 Q8WTV0 SCARB1 Sterol O-acyltransferase 1 P35610 SOAT1 Sterol O-acyltransferase 2 O75908 SOAT2