1.0 2011-09-21 00:38:58 UTC 2015-07-21 06:57:58 UTC FDB024044 CE(24:1(15Z)) Cholesteryl nervonic 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). Placental membrane changes in permeability to water, urea and mannitol in intrauterine growth restriction are related to changes in cholesterol fatty acid content of the membranes with a predominance of saturated fatty acid species such as nervonic acid. Nervonic acid may have preventive effects on obesity-related metabolic disorders. Lower levels of nervonic acid are 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: 16394593, 10446293, 15051839) [HMDB] 24:1 Cholesterol ester cholest-5-en-3beta-yl (15Z-tetracosenoate cholest-5-en-3beta-yl (15Z-tetracosenoate) cholest-5-en-3beta-yl (15Z-tetracosenoic acid Cholesteryl nervonic acid C51H90O2 735.2591 734.694082124 (1S,2R,5S,10S,11S,14R,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 tetracos-15-enoate (1S,2R,5S,10S,11S,14R,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 tetracos-15-enoate 60758-73-8 [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)CCCCCCCCCCCCCC=CCCCCCCCC InChI=1S/C51H90O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-31-49(52)53-44-36-38-50(5)43(40-44)32-33-45-47-35-34-46(42(4)30-28-29-41(2)3)51(47,6)39-37-48(45)50/h14-15,32,41-42,44-48H,7-13,16-31,33-40H2,1-6H3/t42-,44+,45+,46-,47+,48+,50+,51-/m1/s1 PUKCXSHDVCMMAN-LTRCVRFVSA-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 11.19 ALOGPS logs -8.01 ALOGPS solubility 7.14e-06 g/l ALOGPS logp 17.23 ChemAxon pka_strongest_basic -7 ChemAxon iupac (1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-yl tetracos-15-enoate ChemAxon average_mass 735.2591 ChemAxon mono_mass 734.694082124 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)CCCCCCCCCCCCCC=CCCCCCCCC ChemAxon formula C51H90O2 ChemAxon inchi InChI=1S/C51H90O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-24-25-26-27-31-49(52)53-44-36-38-50(5)43(40-44)32-33-45-47-35-34-46(42(4)30-28-29-41(2)3)51(47,6)39-37-48(45)50/h14-15,32,41-42,44-48H,7-13,16-31,33-40H2,1-6H3/t42-,44+,45+,46-,47+,48+,50+,51-/m1/s1 ChemAxon inchikey PUKCXSHDVCMMAN-LTRCVRFVSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 232.13 ChemAxon polarizability 100.21 ChemAxon rotatable_bond_count 28 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB06728 #<Reference:0x000055ce316db348> #<Reference:0x000055ce316db078> #<Reference:0x000055ce316dae20> 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