1.02011-09-21 00:38:57 UTC2015-07-21 06:57:58 UTCFDB024043CE(22:0)CE(22:0) 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-behenoyl-cholesterol22:0 cholesterol ester3beta-Hydroxy-5-cholestene 3-docosanoate3beta-Hydroxy-5-cholestene 3-docosanoic acid5-Cholesten-3beta-ol 3-docosanoate5-Cholesten-3beta-ol 3-docosanoic acidCE(22:0)CE(22:0/0:0)cholest-5-en-3beta-yl docosanoatecholest-5-en-3beta-yl docosanoic acidcholesterol 1-behenoatecholesterol 1-behenoic acidcholesterol 1-docosanoatecholesterol 1-docosanoic acidCholesterol Ester(22:0)Cholesterol Ester(22:0/0:0)cholesteryl 1-behenoatecholesteryl 1-behenoic acidcholesteryl 1-docosanoatecholesteryl 1-docosanoic acidCholesteryl behenateCholesteryl behenic acidCholesteryl docosanoateCholesteryl docosanoic acidC49H88O2709.2218708.67843206(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl docosanoate(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl docosanoate61510-09-6CCCCCCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)CInChI=1S/C49H88O2/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/h30,39-40,42-46H,7-29,31-38H2,1-6H3/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1WBOQXYUYHINMOC-KNEWWSHNSA-N belongs to the class of organic compounds known as phosphatidylcholines. These are glycerophosphocholines in which the two free -OH are attached to one fatty acid each through an ester linkage.PhosphatidylcholinesOrganic compoundsLipids and lipid-like moleculesGlycerophospholipidsGlycerophosphocholinesAliphatic acyclic compoundsAminesCarbonyl compoundsCarboxylic acid estersDialkyl phosphatesDicarboxylic acids and derivativesFatty acid estersHydrocarbon derivativesOrganic oxidesOrganic saltsOrganopnictogen compoundsPhosphocholinesTetraalkylammonium saltsAliphatic acyclic compoundAlkyl phosphateAmineCarbonyl groupCarboxylic acid derivativeCarboxylic acid esterDiacylglycero-3-phosphocholineDialkyl phosphateDicarboxylic acid or derivativesFatty acid esterFatty acylHydrocarbon derivativeOrganic nitrogen compoundOrganic oxideOrganic oxygen compoundOrganic phosphoric acid derivativeOrganic saltOrganonitrogen compoundOrganooxygen compoundOrganopnictogen compoundPhosphocholinePhosphoric acid esterQuaternary ammonium saltTetraalkylammonium saltDiacylglycerophosphocholinesphosphatidylcholine 32:0Solidlogp11.10logs-7.95solubility7.89e-06 g/llogp16.7pka_strongest_basic-7iupac(2R,5S,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl docosanoateaverage_mass709.2218mono_mass708.67843206smilesCCCCCCCCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@]2(C)C3CC[C@]4(C)C(CCC4C3CC=C2C1)[C@H](C)CCCC(C)CformulaC49H88O2inchiInChI=1S/C49H88O2/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/h30,39-40,42-46H,7-29,31-38H2,1-6H3/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1inchikeyWBOQXYUYHINMOC-KNEWWSHNSA-Npolar_surface_area26.3refractivity221.81polarizability97.66rotatable_bond_count27acceptor_count1donor_count0physiological_charge0formal_charge0Specdb::MsMs292225Specdb::MsMs292226Specdb::MsMs292227Specdb::MsMs332362Specdb::MsMs332363Specdb::MsMs332364Specdb::MsMs2770409Specdb::MsMs2770410Specdb::MsMs2770411Specdb::MsMs2908686Specdb::MsMs2908687Specdb::MsMs2908688HMDB06727AnatidaeType 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