1.0 2011-09-21 01:25:50 UTC 2015-10-09 22:33:34 UTC FDB027522 CE(18:3(9Z,12Z,15Z)) CE(18:3(9Z,12Z,15Z)) 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] (3b) Cholest 5 en 3 ol (Z,Z,Z) octadecatrienoate (3b) Cholest 5 en 3 ol (Z,Z,Z) octadecatrienoic acid 1-a-linolenoyl-cholesterol 1-alpha-linolenoyl-cholesterol 18:3 Cholesteryl ester 18:3(9Z,12Z,15Z) cholesterol ester CE(18:3n3/0:0) CE(18:3w3/0:0 Cholest 5 en 3beta yl (Z,Z,Z) octadeca 9,12,15 trien 1 oate Cholest 5 en 3beta yl (Z,Z,Z) octadeca 9,12,15 trien 1 oic acid cholesterol 1-(9Z,12Z,15Z-octadeatrienoate cholesterol 1-(9Z,12Z,15Z-octadeatrienoate) cholesterol 1-(9Z,12Z,15Z-octadeatrienoic acid cholesterol 1-(9Z,12Z,15Z-octadeatrienoic acid) cholesterol 1-a-linolenoate cholesterol 1-a-linolenoic acid cholesterol 1-alpha-linolenoate cholesterol 1-alpha-linolenoic acid Cholesterol a linolenate Cholesterol alpha linolenate Cholesterol Ester(18:3n3/0:0) Cholesterol Ester(18:3w3/0:0) Cholesterol linolenate Cholesterol octadecatrienoate Cholesterol octadecatrienoic acid Cholesteryl (9Z,12Z,15Z)-octadeca-9,12,15-trienoate Cholesteryl (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid cholesteryl 1-(9Z,12Z,15Z-octadeatrienoate cholesteryl 1-(9Z,12Z,15Z-octadeatrienoate) cholesteryl 1-(9Z,12Z,15Z-octadeatrienoic acid cholesteryl 1-(9Z,12Z,15Z-octadeatrienoic acid) cholesteryl 1-a-linolenoate cholesteryl 1-a-linolenoic acid cholesteryl 1-alpha-linolenoate cholesteryl 1-alpha-linolenoic acid Cholesteryl linolenate Cholesteryl linolenic acid Cholesteryl octadecatrienoate Cholesteryl octadecatrienoic acid Linolenic acid cholesteryl ester C45H74O2 647.0679 646.568881612 (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl octadeca-9,12,15-trienoate (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl octadeca-9,12,15-trienoate 2545-22-4 [H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCC=CCC=CCC=CCC InChI=1S/C45H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h8-9,11-12,14-15,26,35-36,38-42H,7,10,13,16-25,27-34H2,1-6H3/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1 FYMCIBHUFSIWCE-XNTGVSEISA-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 Lineolic acids and 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 Octadecanoid Organic oxide Organic oxygen compound Organooxygen compound Solid logp 10.24 ALOGPS logs -8.05 ALOGPS solubility 5.80e-06 g/l ALOGPS logp 13.84 ChemAxon pka_strongest_basic -7 ChemAxon iupac (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-yl octadeca-9,12,15-trienoate ChemAxon average_mass 647.0679 ChemAxon mono_mass 646.568881612 ChemAxon smiles [H][C@@](C)(CCCC(C)C)[C@@]1([H])CC[C@@]2([H])[C@]3([H])CC=C4C[C@]([H])(CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCC=CCC=CCC=CCC ChemAxon formula C45H74O2 ChemAxon inchi InChI=1S/C45H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-25-43(46)47-38-30-32-44(5)37(34-38)26-27-39-41-29-28-40(36(4)24-22-23-35(2)3)45(41,6)33-31-42(39)44/h8-9,11-12,14-15,26,35-36,38-42H,7,10,13,16-25,27-34H2,1-6H3/t36-,38+,39+,40-,41+,42+,44+,45-/m1/s1 ChemAxon inchikey FYMCIBHUFSIWCE-XNTGVSEISA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 206.76 ChemAxon polarizability 85.69 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB10370 Almond Type 1 specific Prunus dulcis 3755 0.052 0.052 0.052 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 7.45 7.45 7.45 mg/100 g Canola oil Type 2 7.45 7.45 7.45 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 0.118 0.118 0.118 mg/100 g Cheese Type 2 specific 0.127 0.127 0.127 mg/100 g Chicken Type 1 specific Gallus gallus 9031 0.026 0.026 0.026 mg/100 g Coconut oil Type 2 0.02 0.02 0.02 mg/100 g Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Corn oil Type 2 1.04 1.04 1.04 mg/100 g Cottage cheese Type 2 0.007 0.007 0.007 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 Eggs Unknown generic 0.011 0.011 0.011 mg/100 g 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 0.002 0.002 0.002 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 0.076 0.076 0.076 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 0.002 0.002 0.002 mg/100 g Olive Type 1 specific Olea europaea 4146 0.104 0.104 0.104 mg/100 g Olive oil Type 2 0.651 0.651 0.651 mg/100 g Ostrich Type 1 specific Struthio camelus 8801 Parmesan cheese Type 2 0.103 0.103 0.103 mg/100 g Pheasant Type 1 specific Phasianus colchicus 9054 Pollock Type 1 specific Pollachius 8059 0.001 0.001 0.001 mg/100 g Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rice Type 1 specific Oryza sativa 4530 0.123 0.123 0.123 mg/100 g Rock ptarmigan Type 1 specific Lagopus muta 64668 Rye bread Type 2 specific 0.141 0.141 0.141 mg/100 g Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Swiss cheese Type 2 0.127 0.127 0.127 mg/100 g Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 White bread Type 1 0.2 0.2 0.2 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