1.0 2011-09-21 00:09:27 UTC 2015-10-09 22:30:26 UTC FDB022167 CE(16:1(9Z)) CE(16:1(9Z)) is an important plasma 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). Cholesteryl palmitoleate is one of the two more prevalent esters that are a component of Dehydroepiandrosterone fatty acid esters (DHEA-FA). DHEA-FA is formed from DHEA by lecithin-cholesterol acyltransferase, localized on high density lipoprotein (HDL). Once DHEA-FA is formed, it is subsequently transferred to very low density lipoprotein (VLDL) and low density lipoprotein (LDL), like cholesteryl esters. Cholesteryl palmitoleate constitutes 20% of the total lipoidal pregnenolone (an important precursor steroid) in follicular fluid. The fatty acid components of the resulting lipoidal pregnenolone derivatives resemble those of cholesteryl esters formed in plasma by the enzymatic activity of lecithin: cholesterol acyltransferase. (PMID 2770299, 8943795) [HMDB] (Z)-Cholesterol 9-hexadecenoate (Z)-Cholesterol 9-hexadecenoic acid 1-palmitoleoyl-cholesterol 16:1(9Z) cholesterol ester CE(16:1) CE(16:1/0:0) CE(16:1n7/0:0) CE(16:1w7/0:0) cholest-5-en-3beta-yl (9Z hexadecenoate cholest-5-en-3beta-yl (9Z hexadecenoate) cholest-5-en-3beta-yl (9Z hexadecenoic acid cholesterol 1-(9Z-hexadecenoate cholesterol 1-(9Z-hexadecenoate) cholesterol 1-(9Z-hexadecenoic acid cholesterol 1-(9Z-hexadecenoic acid) cholesterol 1-palmitoleoate cholesterol 1-palmitoleoic acid Cholesterol Ester(16:1) Cholesterol Ester(16:1/0:0) Cholesterol Ester(16:1n7/0:0) Cholesterol Ester(16:1w7/0:0) Cholesterol palmitoleate cholesteryl 1-(9Z-hexadecenoate cholesteryl 1-(9Z-hexadecenoate) cholesteryl 1-(9Z-hexadecenoic acid cholesteryl 1-(9Z-hexadecenoic acid) cholesteryl 1-palmitoleoate cholesteryl 1-palmitoleoic acid Cholesteryl cis-hexadecenoate Cholesteryl cis-hexadecenoic acid Cholesteryl palmitoleat Cholesteryl palmitoleate Cholesteryl palmitoleic acid C43H74O2 623.0465 622.568881612 (2R,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 hexadec-9-enoate (2R,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 hexadec-9-enoate 16711-66-3 [H][C@@](C)(CCCC(C)C)[C@@]1([H])CCC2C3CC=C4CC(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCCCCCCC=CCCCCCC InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/t34-,36?,37?,38-,39?,40?,42+,43-/m1/s1 HODJWNWCVNUPAQ-DVQNJVTISA-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 10.44 ALOGPS logs -8.03 ALOGPS solubility 5.78e-06 g/l ALOGPS logp 13.67 ChemAxon pka_strongest_basic -7 ChemAxon iupac (2R,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 hexadec-9-enoate ChemAxon average_mass 623.0465 ChemAxon mono_mass 622.568881612 ChemAxon smiles [H][C@@](C)(CCCC(C)C)[C@@]1([H])CCC2C3CC=C4CC(CC[C@]4(C)C3CC[C@]12C)OC(=O)CCCCCCCC=CCCCCCC ChemAxon formula C43H74O2 ChemAxon inchi InChI=1S/C43H74O2/c1-7-8-9-10-11-12-13-14-15-16-17-18-19-23-41(44)45-36-28-30-42(5)35(32-36)24-25-37-39-27-26-38(34(4)22-20-21-33(2)3)43(39,6)31-29-40(37)42/h12-13,24,33-34,36-40H,7-11,14-23,25-32H2,1-6H3/t34-,36?,37?,38-,39?,40?,42+,43-/m1/s1 ChemAxon inchikey HODJWNWCVNUPAQ-DVQNJVTISA-N ChemAxon polar_surface_area 26.3 ChemAxon refractivity 195.32 ChemAxon polarizability 84.23 ChemAxon rotatable_bond_count 20 ChemAxon acceptor_count 1 ChemAxon donor_count 0 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon HMDB00658 #<Reference:0x000055ce32fb87d0> #<Reference:0x000055ce32fb8618> 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