1.0 2011-09-21 00:39:02 UTC 2015-07-21 06:57:59 UTC FDB024048 CE(22:6(4Z,7Z,10Z,13Z,16Z,19Z)) Cholesteryl docosahexaenoic 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). Depression has been found weakly related to serum cholesteryl ester arachidonic/docosahexaenoic fatty acid ratio. In healthy human receiving a diet rich in docosahexaenoic acid (DHA), it was incorporated into LDL cholesteryl esters; DHA does not appear to increase the susceptibility of LDL to oxidation. Lower levels of DHA were found in all plasma lipid fractions from infants fed formula compared with those in the human milk-fed infants, irrespective of the source of the formula supplement. (PMID: 16482070, 15262190, 15051839) [HMDB] 22:6 Cholesterol ester cholest-5-en-3beta-yl (4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoate cholest-5-en-3beta-yl (4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoate) cholest-5-en-3beta-yl (4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid Cholesteryl docosahexaenoate Cholesteryl docosahexaenoic acid C49H76O2 697.1265 696.584531676 (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 docosa-4,7,10,13,16,19-hexaenoate (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 docosa-4,7,10,13,16,19-hexaenoate 70110-50-8 [H][C@@](C)(CCCC(C)C)C1CCC2C3CC=C4C[C@]([H])(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC InChI=1S/C49H76O2/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/h8-9,11-12,14-15,17-18,20-21,23-24,30,39-40,42-46H,7,10,13,16,19,22,25-29,31-38H2,1-6H3/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1 VOEVEGPMRIYYKC-KNEWWSHNSA-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 10.03 ALOGPS logs -7.95 ALOGPS solubility 7.85e-06 g/l ALOGPS logp 14.53 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 docosa-4,7,10,13,16,19-hexaenoate ChemAxon average_mass 697.1265 ChemAxon mono_mass 696.584531676 ChemAxon smiles [H][C@@](C)(CCCC(C)C)C1CCC2C3CC=C4C[C@]([H])(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCC=CCC=CCC=CCC=CCC=CCC=CCC ChemAxon formula C49H76O2 ChemAxon inchi InChI=1S/C49H76O2/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/h8-9,11-12,14-15,17-18,20-21,23-24,30,39-40,42-46H,7,10,13,16,19,22,25-29,31-38H2,1-6H3/t40-,42+,43?,44?,45?,46?,48+,49-/m1/s1 ChemAxon inchikey VOEVEGPMRIYYKC-KNEWWSHNSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 228.51 ChemAxon polarizability 89.93 ChemAxon rotatable_bond_count 21 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB06733 #<Reference:0x000055ce3263da48> #<Reference:0x000055ce3263d890> #<Reference:0x000055ce3263d6d8> Almond Type 1 specific Prunus dulcis 3755 0.0 0.0 0.0 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 Buffalo Type 1 specific Bubalus bubalis 89462 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 0.001 0.001 0.001 mg/100 g Cheese Type 2 specific 0.0 0.0 0.0 mg/100 g Chicken Type 1 specific Gallus gallus 9031 0.007 0.007 0.007 mg/100 g Coconut oil Type 2 0.0 0.0 0.0 mg/100 g Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Cottage cheese Type 2 0.0 0.0 0.0 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 0.089 0.089 0.089 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 0.0 0.0 0.0 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 0.089 0.089 0.089 mg/100 g Olive Type 1 specific Olea europaea 4146 0.0 0.0 0.0 mg/100 g Ostrich Type 1 specific Struthio camelus 8801 Parmesan cheese Type 2 0.0 0.0 0.0 mg/100 g Pheasant Type 1 specific Phasianus colchicus 9054 Pollock Type 1 specific Pollachius 8059 0.116 0.116 0.116 mg/100 g Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rice Type 1 specific Oryza sativa 4530 0.0 0.0 0.0 mg/100 g Rock ptarmigan Type 1 specific Lagopus muta 64668 Rye bread Type 2 specific 0.0 0.0 0.0 mg/100 g Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Swiss cheese Type 2 0.0 0.0 0.0 mg/100 g Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 White bread Type 1 0.0 0.0 0.0 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