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].

   

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].

   

WE 20:6;O3

(1S,2E,10R)-10-acetyl-3-methyl-7-methylidene-6-oxocyclodec-2-en-1-yl (2E)-4-hydroxy-4-methylpent-2-enoate

C20H28O5 (348.1936638)


   

Eunicea sesquiterpenoid 3

Eunicea sesquiterpenoid 3

C15H22O3 (250.1568862)


A natural product found in Eunicea.

   

Eunicea sesquiterpenoid 2

Eunicea sesquiterpenoid 2

C15H22O3 (250.1568862)


A eudesmane sesquiterpenoid in which the eudesmane skeleton is substituted with an alpha-hydroxy group at C-1 (eudesmane numbering) and a methylidene group at C-4, and includes a lactone ring formed between C-12 and a beta-hydroxy group at C-6. It is isolated from Eunicea sp. and exhibits significant inhibitory effect upon the growth of the malarial parasite Plasmodium falciparum

   

Eunicea sesquiterpenoid 5

Eunicea sesquiterpenoid 5

C20H30O5 (350.209313)


A natural product found in Eunicea.

   

Eunicea sesquiterpenoid 6

Eunicea sesquiterpenoid 6

C20H30O5 (350.209313)


A natural product found in Eunicea.

   
   

Eunicea sesquiterpenoid 7

Eunicea sesquiterpenoid 7

C20H28O5 (348.1936638)


A sesquiterpenoid that is a carboxylic ester obtained by the formal condensation of the 6-hydroxy group of cyclodec-4-en-1-one which is also substituted by an acetyl, a methyl and a methylidene group at positions 7, 4 and 10 respectively with the carboxy group of pent-2-enoic acid substituted with a hydroxy and a methyl group at position 4. It is an antiplasmodial drug isolated from a Caribbean gorgonian coral Eunicea sp.

   

2-[(1s,3e,7e,11e)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]propan-2-ol

2-[(1s,3e,7e,11e)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]propan-2-ol

C20H34O (290.2609514)


   

7,11,15-trimethyl-3-methylidenehexadecane-1,2-diol

7,11,15-trimethyl-3-methylidenehexadecane-1,2-diol

C20H40O2 (312.302814)


   

2-[(2z)-3,6,10-trimethyl-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-ylidene]acetaldehyde

2-[(2z)-3,6,10-trimethyl-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-ylidene]acetaldehyde

C17H24O2 (260.17762039999997)


   

[10,14-dimethyl-7-(prop-1-en-2-yl)-15-oxabicyclo[12.1.0]pentadeca-4,10-dien-4-yl]methyl acetate

[10,14-dimethyl-7-(prop-1-en-2-yl)-15-oxabicyclo[12.1.0]pentadeca-4,10-dien-4-yl]methyl acetate

C22H34O3 (346.25078140000005)


   

10-hydroperoxy-6,15a-dihydroxy-3,6,10,14-tetramethyl-7h,11h,12h,13h,14h-cyclotetradeca[b]furan-2,15-dione

10-hydroperoxy-6,15a-dihydroxy-3,6,10,14-tetramethyl-7h,11h,12h,13h,14h-cyclotetradeca[b]furan-2,15-dione

C20H28O7 (380.1834938)


   

(1s,2r,5e,10r,11s,12r,16s)-2-hydroxy-2,6,10-trimethyl-15-methylidene-13,18-dioxatricyclo[9.6.1.0¹²,¹⁶]octadec-5-en-14-one

(1s,2r,5e,10r,11s,12r,16s)-2-hydroxy-2,6,10-trimethyl-15-methylidene-13,18-dioxatricyclo[9.6.1.0¹²,¹⁶]octadec-5-en-14-one

C20H30O4 (334.214398)


   

(1r,3as,3bs,7s,9as,9br,10r,11ar)-9a,11a-dimethyl-1-[(1s)-1-[(1r,2r)-2-methyl-2-[(2r)-3-methylbutan-2-yl]cyclopropyl]ethyl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-7,9b,10-triol

(1r,3as,3bs,7s,9as,9br,10r,11ar)-9a,11a-dimethyl-1-[(1s)-1-[(1r,2r)-2-methyl-2-[(2r)-3-methylbutan-2-yl]cyclopropyl]ethyl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-7,9b,10-triol

C30H50O3 (458.37597500000004)


   

2-[(3ar,12as)-3a,6,10-trimethyl-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol

2-[(3ar,12as)-3a,6,10-trimethyl-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol

C20H32O (288.24530219999997)


   

4,9,12-trimethyl-15-(propan-2-ylidene)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-14-one

4,9,12-trimethyl-15-(propan-2-ylidene)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-14-one

C20H30O2 (302.224568)


   

(3ar,9r,12ar)-9-hydroperoxy-1-isopropyl-3a,6,10-trimethyl-1h,3h,4h,7h,8h,9h,12h,12ah-cyclopenta[11]annulen-2-one

(3ar,9r,12ar)-9-hydroperoxy-1-isopropyl-3a,6,10-trimethyl-1h,3h,4h,7h,8h,9h,12h,12ah-cyclopenta[11]annulen-2-one

C20H32O3 (320.23513219999995)


   

(1r,3s,5s,7e,9r,13s,15s)-9-hydroperoxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-7-ene-14,17-dione

(1r,3s,5s,7e,9r,13s,15s)-9-hydroperoxy-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-7-ene-14,17-dione

C20H28O6 (364.1885788)


   

(1r,2s,5s,7s,11s,12r,13s)-2-hydroxy-16-(hydroxymethyl)-2,7,11-trimethyl-6,14,19-trioxatetracyclo[10.6.1.0⁵,⁷.0¹³,¹⁷]nonadec-16-en-15-one

(1r,2s,5s,7s,11s,12r,13s)-2-hydroxy-16-(hydroxymethyl)-2,7,11-trimethyl-6,14,19-trioxatetracyclo[10.6.1.0⁵,⁷.0¹³,¹⁷]nonadec-16-en-15-one

C20H30O6 (366.204228)


   

3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,5h,6h,7h,8h,11h,12h,12ah-cyclopenta[11]annulene-2,4-dione

3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,5h,6h,7h,8h,11h,12h,12ah-cyclopenta[11]annulene-2,4-dione

C20H30O2 (302.224568)


   

4-isopropyl-7,11-dimethyl-2-(prop-1-en-2-yl)cyclododeca-3,7-dien-1-one

4-isopropyl-7,11-dimethyl-2-(prop-1-en-2-yl)cyclododeca-3,7-dien-1-one

C20H32O (288.24530219999997)


   

(2s,3r,3ar,11as)-3,5',5',6,10-pentamethyl-3a,4,5,8,9,11a-hexahydro-3h-spiro[cyclodeca[b]furan-2,2'-oxolane]

(2s,3r,3ar,11as)-3,5',5',6,10-pentamethyl-3a,4,5,8,9,11a-hexahydro-3h-spiro[cyclodeca[b]furan-2,2'-oxolane]

C20H32O2 (304.24021719999996)


   

(3ar,9r,12as)-9-hydroperoxy-3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,9h,12h,12ah-cyclopenta[11]annulen-2-one

(3ar,9r,12as)-9-hydroperoxy-3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,4h,7h,8h,9h,12h,12ah-cyclopenta[11]annulen-2-one

C20H30O3 (318.21948299999997)


   

(1s,2r,4s,8r,9r,10s,14s,15r)-9-(acetyloxy)-2-hydroxy-1,10,14-trimethyl-5-methylidene-6-oxo-7,18-dioxatricyclo[13.2.1.0⁴,⁸]octadecan-14-yl acetate

(1s,2r,4s,8r,9r,10s,14s,15r)-9-(acetyloxy)-2-hydroxy-1,10,14-trimethyl-5-methylidene-6-oxo-7,18-dioxatricyclo[13.2.1.0⁴,⁸]octadecan-14-yl acetate

C24H36O8 (452.2410056)


   

3,5',5',6,10-pentamethyl-3a,4,5,8,9,11a-hexahydro-3h-spiro[cyclodeca[b]furan-2,2'-oxolane]

3,5',5',6,10-pentamethyl-3a,4,5,8,9,11a-hexahydro-3h-spiro[cyclodeca[b]furan-2,2'-oxolane]

C20H32O2 (304.24021719999996)


   

9-hydroxy-1,10-dimethyl-5,14-dimethylidene-6-oxo-7,18-dioxatricyclo[13.2.1.0⁴,⁸]octadecan-2-yl acetate

9-hydroxy-1,10-dimethyl-5,14-dimethylidene-6-oxo-7,18-dioxatricyclo[13.2.1.0⁴,⁸]octadecan-2-yl acetate

C22H32O6 (392.2198772)


   

(1s,2r,4s,8r,9r,10s,15r)-2,9-dihydroxy-1,10-dimethyl-5,14-dimethylidene-7,18-dioxatricyclo[13.2.1.0⁴,⁸]octadecan-6-one

(1s,2r,4s,8r,9r,10s,15r)-2,9-dihydroxy-1,10-dimethyl-5,14-dimethylidene-7,18-dioxatricyclo[13.2.1.0⁴,⁸]octadecan-6-one

C20H30O5 (350.209313)


   

(1r,3s,5s,7e,9s,13s,15s)-5,9,13-trimethyl-18-methylidene-14,17-dioxo-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-7-en-9-yl acetate

(1r,3s,5s,7e,9s,13s,15s)-5,9,13-trimethyl-18-methylidene-14,17-dioxo-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-7-en-9-yl acetate

C22H30O6 (390.204228)


   

(1r,4e,8e,12s,13r)-12-hydroxy-4,8,12-trimethyl-16-methylidene-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-15-one

(1r,4e,8e,12s,13r)-12-hydroxy-4,8,12-trimethyl-16-methylidene-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-15-one

C20H30O3 (318.21948299999997)


   

(3z,5z,9e,13r)-6-isopropyl-3,9,13-trimethylcyclotetradeca-3,5,9-trien-1-one

(3z,5z,9e,13r)-6-isopropyl-3,9,13-trimethylcyclotetradeca-3,5,9-trien-1-one

C20H32O (288.24530219999997)


   

(1r,2s,4e,8e,12r,13r)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl acetate

(1r,2s,4e,8e,12r,13r)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl acetate

C22H32O5 (376.2249622)


   

2-{3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h-cyclopenta[11]annulen-1-yl}propan-2-ol

2-{3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h-cyclopenta[11]annulen-1-yl}propan-2-ol

C20H32O (288.24530219999997)


   

(1r,3s,5s,8e,12e,15r)-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadeca-8,12-dien-17-one

(1r,3s,5s,8e,12e,15r)-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadeca-8,12-dien-17-one

C20H28O3 (316.2038338)


   

4-(hydroxymethyl)-10,14-dimethyl-7-(prop-1-en-2-yl)-15-oxabicyclo[12.1.0]pentadeca-4,10-dien-6-ol

4-(hydroxymethyl)-10,14-dimethyl-7-(prop-1-en-2-yl)-15-oxabicyclo[12.1.0]pentadeca-4,10-dien-6-ol

C20H32O3 (320.23513219999995)


   

(1s,3s,4z,6r,9r,12s)-4-isopropyl-1,9-dimethyl-7-oxo-6-(prop-1-en-2-yl)-13-oxabicyclo[10.1.0]tridec-4-en-3-yl acetate

(1s,3s,4z,6r,9r,12s)-4-isopropyl-1,9-dimethyl-7-oxo-6-(prop-1-en-2-yl)-13-oxabicyclo[10.1.0]tridec-4-en-3-yl acetate

C22H34O4 (362.24569640000004)


   

(3as,9s,12ar)-9-hydroperoxy-3a,6-dimethyl-10-methylidene-1-(propan-2-ylidene)-3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-2-one

(3as,9s,12ar)-9-hydroperoxy-3a,6-dimethyl-10-methylidene-1-(propan-2-ylidene)-3h,4h,7h,8h,9h,11h,12h,12ah-cyclopenta[11]annulen-2-one

C20H30O3 (318.21948299999997)


   

(2s,3z,7e,11r)-4-isopropyl-7,11-dimethyl-2-(prop-1-en-2-yl)cyclododeca-3,7-dien-1-one

(2s,3z,7e,11r)-4-isopropyl-7,11-dimethyl-2-(prop-1-en-2-yl)cyclododeca-3,7-dien-1-one

C20H32O (288.24530219999997)


   

(3ar,7s,12as)-10,12a-dimethyl-6-methylidene-2-oxo-3-(propan-2-ylidene)-1h,3ah,4h,5h,7h,8h,9h,12h-cyclopenta[11]annulen-7-yl acetate

(3ar,7s,12as)-10,12a-dimethyl-6-methylidene-2-oxo-3-(propan-2-ylidene)-1h,3ah,4h,5h,7h,8h,9h,12h-cyclopenta[11]annulen-7-yl acetate

C22H32O3 (344.23513219999995)


   

(1s,3r,5r,8e,13s)-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-ene-14,17-dione

(1s,3r,5r,8e,13s)-5,9,13-trimethyl-18-methylidene-4,16-dioxatricyclo[13.3.0.0³,⁵]octadec-8-ene-14,17-dione

C20H28O4 (332.19874880000003)


   

(2r,3r,3ar,11as)-3,5',5',6,10-pentamethyl-3a,4,5,8,9,11a-hexahydro-3h-spiro[cyclodeca[b]furan-2,2'-furan]

(2r,3r,3ar,11as)-3,5',5',6,10-pentamethyl-3a,4,5,8,9,11a-hexahydro-3h-spiro[cyclodeca[b]furan-2,2'-furan]

C20H30O2 (302.224568)


   

[(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-ethenyl-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

[(2r,3r,4s,5r,6r)-6-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-ethenyl-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl acetate

C29H44O7 (504.3086874)


   

2,6-dihydroxy-2,6,10-trimethyl-15-methylidene-13,18-dioxatricyclo[9.6.1.0¹²,¹⁶]octadec-4-en-14-one

2,6-dihydroxy-2,6,10-trimethyl-15-methylidene-13,18-dioxatricyclo[9.6.1.0¹²,¹⁶]octadec-4-en-14-one

C20H30O5 (350.209313)