Cholesterol

(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-ol

C27H46O (386.3548466)


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 name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50\\\\% of the lipid in the membrane or 60-80\\\\% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with c... Constituent either free or as esters, of fish liver oils, lard, dairy fats, egg yolk and bran Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

   

microthecin

2-Hydroxy-2-(hydroxymethyl)-2H-pyran-3(6H)-one

C6H8O4 (144.0422568)


A metabolite isolated from morels (e.g. Morchella costata) and red algae (e.g. Gracilariopsis lemaneiformis).

   

Cholesterol

(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-ol

C27H46O (386.3548466)


A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group. Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

   

Lanol

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methylheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C27H46O (386.3548466)


Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

   

methyl (6z,8e,10s,12z,15z)-10-(acetyloxy)octadeca-6,8,12,15-tetraenoate

methyl (6z,8e,10s,12z,15z)-10-(acetyloxy)octadeca-6,8,12,15-tetraenoate

C21H32O4 (348.2300472)


   

methyl (9z,11e)-13-oxooctadeca-9,11-dienoate

methyl (9z,11e)-13-oxooctadeca-9,11-dienoate

C19H32O3 (308.23513219999995)


   

(2s)-1-{[(5z,8z,10e,12r,13s,14z,17z)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoyl]oxy}-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (5z,8z,10e,12r,13s,14z,17z)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoate

(2s)-1-{[(5z,8z,10e,12r,13s,14z,17z)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoyl]oxy}-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (5z,8z,10e,12r,13s,14z,17z)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoate

C49H74O14 (886.5078304)


   

methyl (9z,11e,13s,15z)-13-(acetyloxy)octadeca-9,11,15-trienoate

methyl (9z,11e,13s,15z)-13-(acetyloxy)octadeca-9,11,15-trienoate

C21H34O4 (350.24569640000004)


   

(5z,8z,10z,12r,13s,14z,17z)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoic acid

(5z,8z,10z,12r,13s,14z,17z)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoic acid

C20H30O4 (334.214398)


   

methyl 13-(acetyloxy)octadeca-9,11-dienoate

methyl 13-(acetyloxy)octadeca-9,11-dienoate

C21H36O4 (352.2613456)


   

6-amino-6-carboxy-2-(trimethylammonio)hexanoate

6-amino-6-carboxy-2-(trimethylammonio)hexanoate

C10H20N2O4 (232.1423)


   

methyl 10-(acetyloxy)octadeca-6,8,12,15-tetraenoate

methyl 10-(acetyloxy)octadeca-6,8,12,15-tetraenoate

C21H32O4 (348.2300472)


   

methyl 12,13-bis(acetyloxy)icosa-5,8,10,14,17-pentaenoate

methyl 12,13-bis(acetyloxy)icosa-5,8,10,14,17-pentaenoate

C25H36O6 (432.2511756)


   

methyl 12,13-bis(acetyloxy)-18-oxoicosa-5,8,10,14,16-pentaenoate

methyl 12,13-bis(acetyloxy)-18-oxoicosa-5,8,10,14,16-pentaenoate

C25H34O7 (446.2304414)


   

methyl 12-(acetyloxy)icosa-5,8,10,14,17-pentaenoate

methyl 12-(acetyloxy)icosa-5,8,10,14,17-pentaenoate

C23H34O4 (374.24569640000004)


   

(2r)-2-hydroxy-2-(hydroxymethyl)-6h-pyran-3-one

(2r)-2-hydroxy-2-(hydroxymethyl)-6h-pyran-3-one

C6H8O4 (144.0422568)


   

2-{[(10e)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoyl]oxy}-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 12,13-dihydroxyicosa-5,8,10,14,17-pentaenoate

2-{[(10e)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoyl]oxy}-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl 12,13-dihydroxyicosa-5,8,10,14,17-pentaenoate

C49H74O14 (886.5078304)


   

(2r)-2-(hexadecanoyloxy)-3-{[(2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3s,4r,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propyl (5z,8z,10e,12s,13r,14z,17z)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoate

(2r)-2-(hexadecanoyloxy)-3-{[(2s,3s,4r,5s,6s)-3,4,5-trihydroxy-6-({[(2r,3s,4r,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propyl (5z,8z,10e,12s,13r,14z,17z)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoate

C51H86O17 (970.5864706)


   

methyl (5z,8z,10e,12r,13s,14z,17z)-12,13-bis(acetyloxy)icosa-5,8,10,14,17-pentaenoate

methyl (5z,8z,10e,12r,13s,14z,17z)-12,13-bis(acetyloxy)icosa-5,8,10,14,17-pentaenoate

C25H36O6 (432.2511756)


   

2-(hexadecanoyloxy)-3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propyl (10e)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoate

2-(hexadecanoyloxy)-3-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}propyl (10e)-12,13-dihydroxyicosa-5,8,10,14,17-pentaenoate

C51H86O17 (970.5864706)


   

methyl (5z,8e,10e)-12-(acetyloxy)dodeca-5,8,10-trienoate

methyl (5z,8e,10e)-12-(acetyloxy)dodeca-5,8,10-trienoate

C15H22O4 (266.1518012)


   

methyl (5z,8z,10e,12s,14z,17z)-12-(acetyloxy)icosa-5,8,10,14,17-pentaenoate

methyl (5z,8z,10e,12s,14z,17z)-12-(acetyloxy)icosa-5,8,10,14,17-pentaenoate

C23H34O4 (374.24569640000004)


   

12,13-dihydroxyicosa-5,8,10,14,17-pentaenoic acid

12,13-dihydroxyicosa-5,8,10,14,17-pentaenoic acid

C20H30O4 (334.214398)


   

methyl 13-(acetyloxy)octadeca-9,11,15-trienoate

methyl 13-(acetyloxy)octadeca-9,11,15-trienoate

C21H34O4 (350.24569640000004)


   

methyl (9z,11e,13s)-13-(acetyloxy)octadeca-9,11-dienoate

methyl (9z,11e,13s)-13-(acetyloxy)octadeca-9,11-dienoate

C21H36O4 (352.2613456)


   

methyl (5z,8z,10e,12r,13s,14z,16e)-12,13-bis(acetyloxy)-18-oxoicosa-5,8,10,14,16-pentaenoate

methyl (5z,8z,10e,12r,13s,14z,16e)-12,13-bis(acetyloxy)-18-oxoicosa-5,8,10,14,16-pentaenoate

C25H34O7 (446.2304414)


   

methyl 13-oxooctadeca-9,11-dienoate

methyl 13-oxooctadeca-9,11-dienoate

C19H32O3 (308.23513219999995)


   

methyl 12-(acetyloxy)dodeca-5,8,10-trienoate

methyl 12-(acetyloxy)dodeca-5,8,10-trienoate

C15H22O4 (266.1518012)