1.0 2011-09-21 00:39:05 UTC 2015-07-21 06:57:59 UTC FDB024052 CE(19:0) Cholesteryl nonadecanoic acid is a cholesteryl ester. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 16458590, 9420339) [HMDB] 19:0 Cholesterol ester cholest-5-en-3beta-yl nonadecanoate cholest-5-en-3beta-yl nonadecanoic acid Cholesteryl nonadecanoate Cholesteryl nonadecanoic acid C46H82O2 667.1421 666.631481868 (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 nonadecanoate (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 nonadecanoate 25605-90-7 [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCCCCCCCCCCCC)[C@H](C)CCCC(C)C InChI=1S/C46H82O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-26-44(47)48-39-31-33-45(5)38(35-39)27-28-40-42-30-29-41(37(4)25-23-24-36(2)3)46(42,6)34-32-43(40)45/h27,36-37,39-43H,7-26,28-35H2,1-6H3/t37-,39+,40+,41-,42+,43+,45+,46-/m1/s1 VHYWECIJXTVRSG-TVDLSCFRSA-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 10.88 ALOGPS logs -7.97 ALOGPS solubility 7.23e-06 g/l ALOGPS logp 15.37 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 nonadecanoate ChemAxon average_mass 667.1421 ChemAxon mono_mass 666.631481868 ChemAxon smiles [H][C@@]1(CC[C@@]2([H])[C@]3([H])CC=C4C[C@H](CC[C@]4(C)[C@@]3([H])CC[C@]12C)OC(=O)CCCCCCCCCCCCCCCCCC)[C@H](C)CCCC(C)C ChemAxon formula C46H82O2 ChemAxon inchi InChI=1S/C46H82O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-26-44(47)48-39-31-33-45(5)38(35-39)27-28-40-42-30-29-41(37(4)25-23-24-36(2)3)46(42,6)34-32-43(40)45/h27,36-37,39-43H,7-26,28-35H2,1-6H3/t37-,39+,40+,41-,42+,43+,45+,46-/m1/s1 ChemAxon inchikey VHYWECIJXTVRSG-TVDLSCFRSA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 208.01 ChemAxon polarizability 91.55 ChemAxon rotatable_bond_count 24 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::CMs 16687 Specdb::MsMs 302869 Specdb::MsMs 302870 Specdb::MsMs 302871 Specdb::MsMs 345682 Specdb::MsMs 345683 Specdb::MsMs 345684 Specdb::MsMs 2446408 Specdb::MsMs 2446409 Specdb::MsMs 2446410 Specdb::MsMs 2516028 Specdb::MsMs 2516029 Specdb::MsMs 2516030 HMDB06738 #<Reference:0x000055ce31dcf640> #<Reference:0x000055ce31dcf410> 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 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 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 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 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