1.02011-09-21 01:25:54 UTC2015-07-21 06:59:08 UTCFDB027526CE(22:5(4Z,7Z,10Z,13Z,16Z))CE(22:5(4Z,7Z,10Z,13Z,16Z)) 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. [HMDB]1-Docosapentaenoyl-cholesterol1-osbondoyl-cholesterol22:5(4Z,7Z,10Z,13Z,16Z) cholesterol esterCE(22:5)CE(22:5/0:0)CE(22:5n6/0:0)CE(22:5w6/0:0)cholesterol 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoatecholesterol 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoate)cholesterol 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoic acidcholesterol 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid)Cholesterol 1-docosapentaenoateCholesterol 1-docosapentaenoic acidcholesterol 1-osbondoatecholesterol 1-osbondoic acidCholesterol ester(22:5)Cholesterol ester(22:5/0:0)Cholesterol Ester(22:5n6/0:0)Cholesterol Ester(22:5w6/0:0)cholesteryl 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoatecholesteryl 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoate)cholesteryl 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoic acidcholesteryl 1-(4Z,7Z,10Z,13Z,16Z-docosapentaenoic acid)Cholesteryl 1-docosapentaenoateCholesteryl 1-docosapentaenoic acidcholesteryl 1-osbondoatecholesteryl 1-osbondoic acidC49H78O2699.1424698.60018174[H][C@@](C)(CCCC(C)C)C1CCC2C3CC=C4C[C@]([H])(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCC=CCC=CCC=CCC=CCC=CCCCCCInChI=1S/C49H78O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-47(50)51-42-34-36-48(5)41(38-42)30-31-43-45-33-32-44(40(4)28-26-27-39(2)3)49(45,6)37-35-46(43)48/h11-12,14-15,17-18,20-21,23-24,30,39-40,42-46H,7-10,13,16,19,22,25-29,31-38H2,1-6H3/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1OMHZQRFOHAXINE-KNEWWSHNSA-N belongs to the class of organic compounds known as cholesteryl esters. Cholesteryl esters are compounds containing an esterified cholestane moiety.Cholesteryl estersOrganic compoundsLipids and lipid-like moleculesSteroids and steroid derivativesSteroid estersAliphatic homopolycyclic compoundsCarbonyl compoundsCarboxylic acid estersCholesterols and derivativesDelta-5-steroidsHydrocarbon derivativesMonocarboxylic acids and derivativesOrganic oxidesAliphatic homopolycyclic compoundCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterCholestane-skeletonCholesterolCholesteryl esterDelta-5-steroidHydrocarbon derivativeMonocarboxylic acid or derivativesOrganic oxideOrganic oxygen compoundOrganooxygen compoundSolidaverage_mass699.1424mono_mass698.60018174smiles[H][C@@](C)(CCCC(C)C)C1CCC2C3CC=C4C[C@]([H])(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCC=CCC=CCC=CCC=CCC=CCCCCCformulaC49H78O2inchiInChI=1S/C49H78O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-29-47(50)51-42-34-36-48(5)41(38-42)30-31-43-45-33-32-44(40(4)28-26-27-39(2)3)49(45,6)37-35-46(43)48/h11-12,14-15,17-18,20-21,23-24,30,39-40,42-46H,7-10,13,16,19,22,25-29,31-38H2,1-6H3/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1inchikeyOMHZQRFOHAXINE-KNEWWSHNSA-NHMDB10374AnatidaeType 1specificAnatidae8830BeefaloType 1specificBos taurus X Bison bison297284BisonType 1specificBison bison9901BuffaloType 1specificBubalus bubalis89462Cattle (Beef, Veal)Type 1specificBos taurus9913ChickenType 1specificGallus gallus9031Columbidae (Dove, Pigeon)Type 1specificColumbidae8930DeerType 1specificCervidae9850Domestic goatType 1specificCapra aegagrus hircus9925Domestic pigType 1specificSus scrofa domestica9825ElkType 1specificCervus canadensis1574408EmuType 1specificDromaius novaehollandiae8790European rabbitType 1specificOryctolagus9984Greylag gooseType 1specificAnser anser8843Guinea henType 1specificNumida meleagris8996HorseType 1specificEquus caballus9796Mallard duckType 1specificAnas platyrhynchos8839Mountain hareType 1specificLepus timidus62621Mule deerType 1specificOdocoileus9871OstrichType 1specificStruthio camelus8801PheasantType 1specificPhasianus colchicus9054QuailType 1specificPhasianidae9005RabbitType 1specificLeporidae9979Rock ptarmiganType 1specificLagopus muta64668Sheep (Mutton, Lamb)Type 1specificOvis aries9940SquabType 1specificColumba8931TurkeyType 1specificMeleagris gallopavo9103Velvet duckType 1specificMelanitta fusca371864Wild boarType 1specificSus scrofa9823Liver carboxylesterase 1P23141CES1Lysosomal acid lipase/cholesteryl ester hydrolaseP38571LIPANeutral cholesterol ester hydrolase 1Q6PIU2NCEH1Phosphatidylcholine-sterol acyltransferaseP04180LCATScavenger receptor class B member 1Q8WTV0SCARB1Sterol O-acyltransferase 1P35610SOAT1Sterol O-acyltransferase 2O75908SOAT2