1.0 2011-09-21 00:39:01 UTC 2019-11-26 03:21:11 UTC FDB024047 CE(20:5(5Z,8Z,11Z,14Z,17Z) 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] (3b)-Cholest-5-en-3-ol (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoate (3b)-Cholest-5-en-3-ol (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-eicosapentaenoic acid (3b)-Cholest-5-en-3-ol (all-Z)-5,8,11,14,17-eicosapentaenoate (3b)-Cholest-5-en-3-ol (all-Z)-5,8,11,14,17-eicosapentaenoic acid 20:5 Cholesterol ester cholest-5-en-3beta-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoate cholest-5-en-3beta-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoate) cholest-5-en-3beta-yl (5Z,8Z,11Z,14Z,17Z-eicosapentaenoic acid Cholesteryl 5,8,11,14,17-eicosapentaenoate Cholesteryl 5,8,11,14,17-eicosapentaenoic acid Cholesteryl eicosapentaenoate Cholesteryl eicosapentaenoic acid C47H74O2 671.0893 670.568881612 (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 icosa-5,8,11,14,17-pentaenoate (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 icosa-5,8,11,14,17-pentaenoate 74892-97-0 [H][C@@](C)(CCCC(C)C)C1CCC2C3CC=C4C[C@]([H])(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCCC=CCC=CCC=CCC=CCC=CCC InChI=1S/C47H74O2/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/h8-9,11-12,14-15,17-18,20-21,28,37-38,40-44H,7,10,13,16,19,22-27,29-36H2,1-6H3/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1 XZFUGMCJZFRBKF-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 10.03 ALOGPS logs -7.97 ALOGPS solubility 7.27e-06 g/l ALOGPS logp 14 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 icosa-5,8,11,14,17-pentaenoate ChemAxon average_mass 671.0893 ChemAxon mono_mass 670.568881612 ChemAxon smiles [H][C@@](C)(CCCC(C)C)C1CCC2C3CC=C4C[C@]([H])(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCCC=CCC=CCC=CCC=CCC=CCC ChemAxon formula C47H74O2 ChemAxon inchi InChI=1S/C47H74O2/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/h8-9,11-12,14-15,17-18,20-21,28,37-38,40-44H,7,10,13,16,19,22-27,29-36H2,1-6H3/t38-,40+,41?,42?,43?,44?,46+,47-/m1/s1 ChemAxon inchikey XZFUGMCJZFRBKF-YEYBIBAWSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 218.19 ChemAxon polarizability 86.03 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB06731 #<Reference:0x000055ce2ca4f4c0> #<Reference:0x000055ce2ca4f100> #<Reference:0x000055ce2ca4ee80> #<Reference:0x000055ce2ca4e930> Almond Type 1 specific Prunus dulcis 3755 0.002 0.002 0.002 mg/100 g Carrot Type 1 specific Daucus carota ssp. sativus 79200 0.0 0.0 0.0 mg/100 g Cheddar Cheese Type 2 Cheddar Cheese 0.01 0.01 0.01 mg/100 g Cheese Type 2 specific 0.009 0.009 0.009 mg/100 g Chicken Type 1 specific Gallus gallus 9031 0.004 0.004 0.004 mg/100 g Coconut oil Type 2 0.0 0.0 0.0 mg/100 g Cottage cheese Type 2 0.001 0.001 0.001 mg/100 g Haddock Type 1 specific Melanogrammus aeglefinus 8056 0.042 0.042 0.042 mg/100 g Milk (Cow) Type 2 specific 103.0 162.0 60.0 uM Mozzarella cheese Type 2 0.006 0.006 0.006 mg/100 g 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 0.042 0.042 0.042 mg/100 g Olive Type 1 specific Olea europaea 4146 0.0 0.0 0.0 mg/100 g Parmesan cheese Type 2 0.008 0.008 0.008 mg/100 g Pollock Type 1 specific Pollachius 8059 0.049 0.049 0.049 mg/100 g Rice Type 1 specific Oryza sativa 4530 0.0 0.0 0.0 mg/100 g Rye bread Type 2 specific 0.0 0.0 0.0 mg/100 g Swiss cheese Type 2 0.009 0.009 0.009 mg/100 g White bread Type 1 0.002 0.002 0.002 mg/100 g 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