NCBI Taxonomy: 7618

Ophiuroidea (ncbi_taxid: 7618)

found 27 associated metabolites at class taxonomy rank level.

Ancestor: Asterozoa

Child Taxonomies: Ophiuridea, Myophiuroidea, unclassified Ophiuroidea

Stigmasterol

(3S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H48O (412.3705)


Stigmasterol is a phytosterol, meaning it is steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. Stigmasterol is found to be associated with phytosterolemia, which is an inborn error of metabolism. Stigmasterol is a 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. It has a role as a plant metabolite. It is a 3beta-sterol, a stigmastane sterol, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Stigmasterol is a natural product found in Ficus auriculata, Xylopia aromatica, and other organisms with data available. Stigmasterol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and unsaturated bonds in position 5-6 of the B ring, and position 22-23 in the alkyl substituent. Stigmasterol is found in the fats and oils of soybean, calabar bean and rape seed, as well as several other vegetables, legumes, nuts, seeds, and unpasteurized milk. See also: Comfrey Root (part of); Saw Palmetto (part of); Plantago ovata seed (part of). Stigmasterol is an unsaturated plant sterol occurring in the plant fats or oils of soybean, calabar bean, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong) and American Ginseng. Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

   

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 (386.3548)


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 sulfate

[(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]oxidanesulfonic acid

C27H46O4S (466.3117)


Cholesterol sulfate, or cholest-5-en-3beta-ol sulfate, is an endogenous steroid and the C3beta sulfate ester of cholesterol. It is formed from cholesterol by steroid sulfotransferases (SSTs) such as SULT2B1b (also known as cholesterol sulfotransferase) and is converted back into cholesterol by steroid sulfatase (STS). Accumulation of cholesterol sulfate in the skin is implicated in the pathophysiology of X-linked ichthyosis, a congenital disorder in which STS is non-functional and the body cannot convert cholesterol sulfate back into cholesterol. Cholesterol sulfate is quantitatively the most important known sterol sulfate in human plasma, where it is present in a concentration that overlaps that of the other abundant circulating steroid sulfate, dehydroepiandrosterone (DHEA) sulfate (PMID 12730293). Cholesterol sulfate has a stabilizing function on the membrane, supports platelet adhesion and is involved in signal transduction (PMID 12730293). It plays a role in protecting erythrocytes from osmotic lysis and regulating sperm capacitation. Cholesterol sulfate can regulate the activity of serine proteases, e.g., those involved in blood clotting, fibrinolysis, and epidermal cell adhesion (PMID 12730293). As a result of its ability to regulate the activity of selective protein kinase C isoforms and modulate the specificity of phosphatidylinositol 3-kinase, cholesterol sulfate is involved in signal transduction (PMID 12730293). Cholesterol sulfate functions in keratinocyte differentiation, inducing genes that encode for key components involved in development of the barrier (PMID 12730293). Cholesterol sulfate is a sterol sulfate in human plasma. It is a component of cell membrane and has a regulatory function. It has a stabilizing function on the membrane, supports platelet adhesion and involves in signal transduction. (PMID 12730293) [HMDB] D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015842 - Serine Proteinase Inhibitors D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents

   

Poriferasterol

poriferasta-5,22E-dien-3β-ol

C29H48O (412.3705)


   

Poriferasterol

14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

C29H48O (412.3705)


   

cholesterol sulfate

[(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-yl] hydrogen sulfate

C27H46O4S (466.3117)


D004791 - Enzyme Inhibitors > D011480 - Protease Inhibitors > D015842 - Serine Proteinase Inhibitors A steroid sulfate that is cholesterol substituted by a sulfoxy group at position 3. D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents

   

Stigmasterol

Stigmasterol

C29H48O (412.3705)


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

(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 (386.3548)


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].

   

cholesterol sulfate

cholesterol sulfate

C27H46O4S (466.3117)


   

[(1r,3as,3bs,7s,9r,9ar,9bs,11as)-9-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-1-(sulfooxy)heptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

[(1r,3as,3bs,7s,9r,9ar,9bs,11as)-9-hydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-1-(sulfooxy)heptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H46O9S2 (578.2583)


   

3,3a,7a-tribenzyl-3-hydroxy-7-phenyl-dihydrofuro[3,2-b]pyran-2,5-dione

3,3a,7a-tribenzyl-3-hydroxy-7-phenyl-dihydrofuro[3,2-b]pyran-2,5-dione

C34H30O5 (518.2093)


   

1,5,6-trichloro-2-(dichloromethyl)-6-methylocta-1,3,7-triene

1,5,6-trichloro-2-(dichloromethyl)-6-methylocta-1,3,7-triene

C10H11Cl5 (305.9303)


   

(1e,3e,5s,6r)-1,5,6-trichloro-2-(dichloromethyl)-6-methylocta-1,3,7-triene

(1e,3e,5s,6r)-1,5,6-trichloro-2-(dichloromethyl)-6-methylocta-1,3,7-triene

C10H11Cl5 (305.9303)


   

4,8,9-trihydroxyindolo[2,1-b]quinazoline-6,12-dione

4,8,9-trihydroxyindolo[2,1-b]quinazoline-6,12-dione

C15H8N2O5 (296.0433)


   

[(1r,3as,3bs,7s,8s,9ar,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methyl-7-(sulfooxy)heptan-2-yl]-8-(sulfooxy)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

[(1r,3as,3bs,7s,8s,9ar,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methyl-7-(sulfooxy)heptan-2-yl]-8-(sulfooxy)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H46O12S3 (658.2151)


   

[(1r,3as,3br,5r,5as,7r,9ar,9bs,11r,11as)-5-hydroxy-1-[(2r)-1-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-11-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

[(1r,3as,3br,5r,5as,7r,9ar,9bs,11r,11as)-5-hydroxy-1-[(2r)-1-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-11-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C32H56O11S (648.3543)


   

methyl 13-[(2s)-2-hydroxy-3,4-dimethyl-5-oxofuran-2-yl]tridecanoate

methyl 13-[(2s)-2-hydroxy-3,4-dimethyl-5-oxofuran-2-yl]tridecanoate

C20H34O5 (354.2406)


   

[(1s,2r,3r,6r)-6-hydroxy-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(1r,4r,5s,6r)-4-hydroxy-2,2,6-trimethyl-5-(sulfooxy)cyclohexyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohexyl]oxidanesulfonic acid

[(1s,2r,3r,6r)-6-hydroxy-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(1r,4r,5s,6r)-4-hydroxy-2,2,6-trimethyl-5-(sulfooxy)cyclohexyl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohexyl]oxidanesulfonic acid

C40H60O10S2 (764.3628)


   

11,14-dibenzyl-14-hydroxy-10-phenyl-12,15-dioxatetracyclo[7.5.2.0¹,¹¹.0³,⁸]hexadeca-3,5,7-triene-13,16-dione

11,14-dibenzyl-14-hydroxy-10-phenyl-12,15-dioxatetracyclo[7.5.2.0¹,¹¹.0³,⁸]hexadeca-3,5,7-triene-13,16-dione

C34H28O5 (516.1937)


   

(1s,9r,10r,11s,14s)-11,14-dibenzyl-14-hydroxy-10-phenyl-12,15-dioxatetracyclo[7.5.2.0¹,¹¹.0³,⁸]hexadeca-3,5,7-triene-13,16-dione

(1s,9r,10r,11s,14s)-11,14-dibenzyl-14-hydroxy-10-phenyl-12,15-dioxatetracyclo[7.5.2.0¹,¹¹.0³,⁸]hexadeca-3,5,7-triene-13,16-dione

C34H28O5 (516.1937)


   

[9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

[9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H46O4S (466.3117)


   

(3s,3as,7r,7as)-3,3a,7a-tribenzyl-3-hydroxy-7-phenyl-dihydrofuro[3,2-b]pyran-2,5-dione

(3s,3as,7r,7as)-3,3a,7a-tribenzyl-3-hydroxy-7-phenyl-dihydrofuro[3,2-b]pyran-2,5-dione

C34H30O5 (518.2093)


   

methyl 13-(2-hydroxy-3,4-dimethyl-5-oxofuran-2-yl)tridecanoate

methyl 13-(2-hydroxy-3,4-dimethyl-5-oxofuran-2-yl)tridecanoate

C20H34O5 (354.2406)


   

[(1r,3as,3bs,7r,9ar,9bs,11as)-9a,11a-dimethyl-1-[(2r)-6-methyl-1-(sulfooxy)heptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

[(1r,3as,3bs,7r,9ar,9bs,11as)-9a,11a-dimethyl-1-[(2r)-6-methyl-1-(sulfooxy)heptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H46O8S2 (562.2634)


   

[(1r,3as,3bs,5as,6s,7r,9as,9bs,10s,11as)-6,10-dihydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-1-(sulfooxy)heptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

[(1r,3as,3bs,5as,6s,7r,9as,9bs,10s,11as)-6,10-dihydroxy-9a,11a-dimethyl-1-[(2r)-6-methyl-1-(sulfooxy)heptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H48O10S2 (596.2689)


   

[(1r,3as,3br,5r,5as,7r,9ar,9bs,11r,11as)-5-hydroxy-1-[(2r)-1-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-11-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

[(1r,3as,3br,5r,5as,7r,9ar,9bs,11r,11as)-5-hydroxy-1-[(2r)-1-hydroxy-6-methylheptan-2-yl]-9a,11a-dimethyl-11-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C33H58O12S (678.3649)


   

[(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methyl-7-(sulfooxy)heptan-2-yl]-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

[(1r,3as,3br,5as,7s,8s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methyl-7-(sulfooxy)heptan-2-yl]-8-(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C27H48O12S3 (660.2308)