NCBI Taxonomy: 44191
Plexauridae (ncbi_taxid: 44191)
found 500 associated metabolites at family taxonomy rank level.
Ancestor: Malacalcyonacea
Child Taxonomies: Muricea, Plexaura, Thesea, Paramuricea, Eunicea, Bebryce, Lytreia, Paracis, Swiftia, Menella, Anthomuricea, Caliacis, Trimuricea, Muriceides, Cryogorgia, Plexaurella, Hypnogorgia, Villogorgia, Placogorgia, Discogorgia, Echinogorgia, Trichogorgia, Heterogorgia, Paraplexaura, Pseudothesea, Alaskagorgia, Spinimuricea, Psammogorgia, Lepidomuricea, Echinomuricea, Pseudoplexaura, Chromoplexaura, environmental samples, unclassified Plexauridae
Adenosine
C10H13N5O4 (267.09674980000005)
Adenosine is a ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. It has a role as an anti-arrhythmia drug, a vasodilator agent, an analgesic, a human metabolite and a fundamental metabolite. It is a purines D-ribonucleoside and a member of adenosines. It is functionally related to an adenine. The structure of adenosine was first described in 1931, though the vasodilating effects were not described in literature until the 1940s. Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy, though it is rarely used in this indication, having largely been replaced by [dipyridamole] and [regadenson]. Adenosine is also indicated in the treatment of supraventricular tachycardia. Adenosine was granted FDA approval on 30 October 1989. Adenosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Adenosine is an Adenosine Receptor Agonist. The mechanism of action of adenosine is as an Adenosine Receptor Agonist. Adenosine is a natural product found in Smilax bracteata, Mikania laevigata, and other organisms with data available. Adenosine is a ribonucleoside comprised of adenine bound to ribose, with vasodilatory, antiarrhythmic and analgesic activities. Phosphorylated forms of adenosine play roles in cellular energy transfer, signal transduction and the synthesis of RNA. Adenosine is a nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer - as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate, cAMP. Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously, adenosine causes transient heart block in the AV node. Because of the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Adenosine is a metabolite found in or produced by Saccharomyces cerevisiae. A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. See also: Adenosine; Niacinamide (component of); Adenosine; Glycerin (component of); Adenosine; ginsenosides (component of) ... View More ... Adenosine is a nucleoside that is composed of adenine and D-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously adenosine causes transient heart block in the AV node. Due to the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Overdoses of adenosine intake (as a drug) can lead to several side effects including chest pain, feeling faint, shortness of breath, and tingling of the senses. Serious side effects include a worsening dysrhythmia and low blood pressure. When present in sufficiently high levels, adenosine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of adenosine are associated with adenosine deaminase deficiency. Adenosine is a precursor to deoxyadenosine, which is a precursor to dATP. A buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes. Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a beta-N9-glycosidic bond. [Wikipedia]. Adenosine is found in many foods, some of which are borage, japanese persimmon, nuts, and barley. COVID info from PDB, Protein Data Bank, COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. Adenosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-61-7 (retrieved 2024-06-29) (CAS RN: 58-61-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2].
Caffeine
Caffeine is a methyl xanthine alkaloid that is also classified as a purine. Formally, caffeine belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety. Caffeine is chemically related to the adenine and guanine bases of deoxyribonucleic acid (DNA) and ribonucleic acid (RNA). It is found in the seeds, nuts, or leaves of a number of plants native to Africa, East Asia and South America and helps to protect them against predator insects and to prevent germination of nearby seeds. The most well-known source of caffeine is the coffee bean. Caffeine is the most widely consumed psychostimulant drug in the world. 85\\\% of American adults consumed some form of caffeine daily, consuming 164 mg on average. Caffeine is mostly is consumed in the form of coffee. Caffeine is a central nervous system stimulant that reduces fatigue and drowsiness. At normal doses, caffeine has variable effects on learning and memory, but it generally improves reaction time, wakefulness, concentration, and motor coordination. Caffeine is a proven ergogenic aid in humans. Caffeine improves athletic performance in aerobic (especially endurance sports) and anaerobic conditions. Moderate doses of caffeine (around 5 mg/kg) can improve sprint performance, cycling and running time trial performance, endurance and cycling power output (PMID: 32551869). At intake levels associated with coffee consumption, caffeine appears to exert most of its biological effects through the antagonism of the A1 and A2A subtypes of the adenosine receptor. Adenosine is an endogenous neuromodulator with mostly inhibitory effects, and adenosine antagonism by caffeine results in effects that are generally stimulatory. Some physiological effects associated with caffeine administration include central nervous system stimulation, acute elevation of blood pressure, increased metabolic rate, and diuresis. A number of in vitro and in vivo studies have demonstrated that caffeine modulates both innate and adaptive immune responses. For instance, studies indicate that caffeine and its major metabolite paraxanthine suppress neutrophil and monocyte chemotaxis, and also suppress production of the pro-inflammatory cytokine tumor necrosis factor (TNF) alpha from human blood. Caffeine has also been reported to suppress human lymphocyte function as indicated by reduced T-cell proliferation and impaired production of Th1 (interleukin [IL]-2 and interferon [IFN]-gamma), Th2 (IL-4, IL-5) and Th3 (IL-10) cytokines. Studies also indicate that caffeine suppresses antibody production. The evidence suggests that at least some of the immunomodulatory actions of caffeine are mediated via inhibition of cyclic adenosine monophosphate (cAMP)-phosphodiesterase (PDE), and consequential increase in intracellular cAMP concentrations. Overall, these studies indicate that caffeine, like other members of the methylxanthine family, is largely anti-inflammatory in nature, and based on the pharmacokinetics of caffeine, many of its immunomodulatory effects occur at concentrations that are relevant to normal human consumption. (PMID: 16540173). Caffeine is rapidly and almost completely absorbed in the stomach and small intestine and distributed to all tissues, including the brain. Caffeine metabolism occurs primarily in the liver, where the activity of the cytochrome P450 isoform CYP1A2 accounts for almost 95\\\% of the primary metabolism of caffeine. CYP1A2-catalyzed 3-demethylation of caffeine results in the formation of 1,7-dimethylxanthine (paraxanthine). Paraxanthine may be demethylated by CYP1A2 to form 1-methylxanthine, which may be oxidized to 1-methyluric acid by xanthine oxidase. Paraxanthine may also be hydroxylated by CYP2A6 to form 1,7-dimethyluric acid, or acetylated by N-acetyltransferase 2 (NAT2) to form 5-acetylamino-6-formylamino-3-methyluracil, an unstable compound that may be deformylated nonenzymatically to form ... Caffeine appears as odorless white powder or white glistening needles, usually melted together. Bitter taste. Solutions in water are neutral to litmus. Odorless. (NTP, 1992) Caffeine is a trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee. It has a role as a central nervous system stimulant, an EC 3.1.4.* (phosphoric diester hydrolase) inhibitor, an adenosine receptor antagonist, an EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor, a ryanodine receptor agonist, a fungal metabolite, an adenosine A2A receptor antagonist, a psychotropic drug, a diuretic, a food additive, an adjuvant, a plant metabolite, an environmental contaminant, a xenobiotic, a human blood serum metabolite, a mouse metabolite, a geroprotector and a mutagen. It is a purine alkaloid and a trimethylxanthine. Caffeine is a drug of the methylxanthine class used for a variety of purposes, including certain respiratory conditions of the premature newborn, pain relief, and to combat drowsiness. Caffeine is similar in chemical structure to [Theophylline] and [Theobromine]. It can be sourced from coffee beans, but also occurs naturally in various teas and cacao beans, which are different than coffee beans. Caffeine is also used in a variety of cosmetic products and can be administered topically, orally, by inhalation, or by injection. The caffeine citrate injection, used for apnea of the premature newborn, was initially approved by the FDA in 1999. According to an article from 2017, more than 15 million babies are born prematurely worldwide. This correlates to about 1 in 10 births. Premature birth can lead to apnea and bronchopulmonary dysplasia, a condition that interferes with lung development and may eventually cause asthma or early onset emphysema in those born prematurely. Caffeine is beneficial in preventing and treating apnea and bronchopulmonary dysplasia in newborns, improving the quality of life of premature infants. Caffeine is a Central Nervous System Stimulant and Methylxanthine. The physiologic effect of caffeine is by means of Central Nervous System Stimulation. Caffeine is xanthine alkaloid that occurs naturally in seeds, leaves and fruit of several plants and trees that acts as a natural pesticide. Caffeine is a major component of coffee, tea and chocolate and in humans acts as a central nervous system (CNS) stimulant. Consumption of caffeine, even in high doses, has not been associated with elevations in serum enzyme elevations or instances of clinically apparent liver injury. Caffeine is a natural product found in Mus musculus, Herrania cuatrecasana, and other organisms with data available. Caffeine is a methylxanthine alkaloid found in the seeds, nuts, or leaves of a number of plants native to South America and East Asia that is structurally related to adenosine and acts primarily as an adenosine receptor antagonist with psychotropic and anti-inflammatory activities. Upon ingestion, caffeine binds to adenosine receptors in the central nervous system (CNS), which inhibits adenosine binding. This inhibits the adenosine-mediated downregulation of CNS activity; thus, stimulating the activity of the medullary, vagal, vasomotor, and respiratory centers in the brain. This agent also promotes neurotransmitter release that further stimulates the CNS. The anti-inflammatory effects of caffeine are due the nonselective competitive inhibition of phosphodiesterases (PDEs). Inhibition of PDEs raises the intracellular concentration of cyclic AMP (cAMP), activates protein kinase A, and inhibits leukotriene synthesis, which leads to reduced inflammation and innate immunity. Caffeine is the most widely consumed psychostimulant drug in the world that mostly is consumed in the form of coffee. Whether caffeine and/or coffee consumption contribute to the development of cardiovascular disease (CVD), the single leading cause of death in the US, is uncle... Component of coffee beans (Coffea arabica), many other Coffea subspecies, chocolate (Theobroma cacao), tea (Camellia thea), kolanut (Cola acuminata) and several other Cola subspecies and several other plants. It is used in many cola-type beverages as a flavour enhancer. Caffeine is found in many foods, some of which are black cabbage, canola, jerusalem artichoke, and yellow bell pepper. A trimethylxanthine in which the three methyl groups are located at positions 1, 3, and 7. A purine alkaloid that occurs naturally in tea and coffee. [Raw Data] CBA01_Caffeine_pos_50eV.txt [Raw Data] CBA01_Caffeine_pos_20eV.txt [Raw Data] CBA01_Caffeine_pos_40eV.txt [Raw Data] CBA01_Caffeine_pos_10eV.txt [Raw Data] CBA01_Caffeine_pos_30eV.txt Caffeine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-08-2 (retrieved 2024-06-29) (CAS RN: 58-08-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Campesterol
Campesterol is a phytosterol, meaning it is a 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. -- Wikipedia. Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane. Campesterol is a natural product found in Haplophyllum bucharicum, Bugula neritina, and other organisms with data available. Campesterol is a steroid derivative that is the simplest sterol, characterized by the hydroxyl group in position C-3 of the steroid skeleton, and saturated bonds throughout the sterol structure, with the exception of the 5-6 double bond in the B ring. Campesterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=474-62-4 (retrieved 2024-07-01) (CAS RN: 474-62-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.
Stigmasterol
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
Stigmastanol
Stigmastanol is a 3-hydroxy steroid that is 5alpha-stigmastane which is substituted at the 3beta position by a hydroxy group. It has a role as an anticholesteremic drug and a plant metabolite. It is a 3-hydroxy steroid and a member of phytosterols. It derives from a hydride of a 5alpha-stigmastane. Stigmastanol is a natural product found in Alnus japonica, Dracaena cinnabari, and other organisms with data available. Stigmastanol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and a saturated bond in position 5-6 of the B ring. See also: Saw Palmetto (part of). D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents C1907 - Drug, Natural Product > C28178 - Phytosterol > C68422 - Saturated Phytosterol D009676 - Noxae > D000963 - Antimetabolites Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2]. Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2].
Serotonin
Serotonin or 5-hydroxytryptamine (5-HT) is a molecule that belongs to the class of compounds known as indoleamines. An indoleamine consists of an indole ring that bears an amino group or an alkyl amino group attached to the indole ring. Serotonin has an aminoethyl at position 2 and a hydroxyl group at position 5 of the indole ring. Serotonin exists in all living organisms, ranging from bacteria to plants to humans. In mammals, serotonin functions as a monoamine neurotransmitter, a biochemical messenger and regulator. It is synthesized from the essential amino acid L-Tryptophan. Approximately 90\\\\% of the human bodys total serotonin is located in the enterochromaffin cells in the GI tract, where it regulates intestinal movements. About 8\\\\% is found in platelets and 1–2\\\\% in the CNS. Serotonin in the nervous system acts as a local transmitter at synapses, and as a paracrine or hormonal modulator of circuits upon diffusion, allowing a wide variety of "state-dependent" behavioral responses to different stimuli. Serotonin is widely distributed in the nervous system of vertebrates and invertebrates and some of its behavioral effects have been preserved along evolution. Such is the case of aggressive behavior and rhythmic motor patterns, including those responsible for feeding. In vertebrates, which display a wider and much more sophisticated behavioral repertoire, serotonin also modulates sleep, the arousal state, sexual behavior, and others. Deficiencies of the serotonergic system causes disorders such as depression, obsessive-compulsive disorder, phobias, posttraumatic stress disorder, epilepsy, and generalized anxiety disorder. Serotonin has three different modes of action in the nervous system: as transmitter, acting locally at synaptic boutons; upon diffusion at a distance from its release sites, producing paracrine (also called volume) effects, and by circulating in the blood stream, producing hormonal effects. The three modes can affect a single neuronal circuit. (PMID: 16047543). Serotonin is also a microbial metabolite that can be found in the feces and urine of mammals. Urinary serotonin is produced by Candida, Streptococcus, Escherichia, and Enterococcus (PMID: 24621061). In plants, serotonin was first found and reported in a legume called Mucuna pruriens. The greatest concentration of serotonin in plants has been found in walnuts and hickory. In pineapples, banana, kiwi fruit, plums and tomatoes the concentration of serotonin is around 3 to 30 mg/kg. Isolated from bananas and other fruitsand is also from cotton (Gossypium hirsutum) [DFC]. Serotonin is found in many foods, some of which are common pea, eggplant, swiss chard, and dill. Serotonin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=50-67-9 (retrieved 2024-07-01) (CAS RN: 50-67-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Cholestenone
Cholestenone belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, cholestenone is considered to be a sterol lipid molecule. Cholestenone is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Cholestenone is a dehydrocholestanone. It is a product of cholesterol oxidase {EC 1.1.3.6] in the Bile acid biosynthesis pathway (KEGG). [HMDB] Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop and efflux. Cholestenone may cause long-term functional defects in cells[1][2]. Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop and efflux. Cholestenone may cause long-term functional defects in cells[1][2].
N-Methyltryptamine
N-Methyltryptamine (NMT), or monomethyltryptamine, is a tryptamine alkaloid that has been found in the bark, shoots and leaves of numerous plants. (wikipedia). N-Methyltryptamine was detected in urine from all autistic patients with mental retardation and epilepsy and many autistic patients (32/47) with mental retardation (PubMed ID 8747157 ). N-Methyltryptamine (NMT), or monomethyltryptamine, is a tryptamine alkaloid that has been found in the bark, shoots and leaves of numerous plants. (wikipedia)
Cholesterol
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].
Xanthyletin
Xanthyletin is a member of the class of compounds known as linear pyranocoumarins. Linear pyranocoumarins are organic compounds containing a pyran (or a hydrogenated derivative) linearly fused to a coumarin moiety. Xanthyletin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Xanthyletin can be found in lemon, lime, mandarin orange (clementine, tangerine), and sweet orange, which makes xanthyletin a potential biomarker for the consumption of these food products.
Brassicasterol
Brassicasterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, brassicasterol is considered to be a sterol lipid molecule. Brassicasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Brassicasterol is a potential CSF biomarker for Alzheimer’s disease (PMID: 21585343). C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Constituent of Brassica rapa oil Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].
Desmosterol
Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is found in many foods, some of which are fig, sago palm, mexican groundcherry, and pepper (c. frutescens). Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1]. Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1].
Prostaglandin A2
Produced by the seminal vesicles, prostaglandins are a group of lipid compounds that are derived enzymatically from fatty acids. Technically hormones, the prostanoid class of fatty acid derivatives is a subclass of eicosanoids. The eicosanoids consist of the prostaglandins (PGs), thromboxanes (TXs), leukotrienes (LTs), and lipoxins (LXs). The PGs and TXs are collectively identified as prostanoids. Prostaglandins were originally shown to be synthesized in the prostate gland, thromboxanes from platelets (thrombocytes), and leukotrienes from leukocytes, hence the derivation of their names. All mammalian cells except erythrocytes synthesize eicosanoids. These molecules are extremely potent, able to cause profound physiological effects at very dilute concentrations. All eicosanoids function locally at the site of synthesis through receptor-mediated G-protein linked signaling pathways. Prostaglandin A is a cyclopentenone and is an endogenous metabolite derived from arachidonic acid. It exhibits potent cellular anti-proliferative activity in vivo and in vitro. Excess PGA2 causes an accumulation in both S and G2/M, and a marked decrease in G1. There is also an increase in DNA content preceeding the G0/G1 peak (indicative of apoptotic body formation) mediated by changes in expression levels of Bax and Bcl-2. Produced by the seminal vessicals: Prostaglandins are a group of lipid compounds that are derived enzymatically from fattyacids. Technically a hormone, the prostanoid class of fatty acid derivatives is a subclass of eicosanoids. Prostaglandin A is cyclopentenone and endogenous metabolite derived from arachidonic acid. Exhibits potent cellular anti-proliferative activity in vivo and in vitro. Excess PGA2 causes an accumulation in both S and G2/M, and a marked decrease in G1. As well there is an increase in DNA content preceeding the G0/G1 peak (indicative of apoptic body formation) mediated by changes in expression levels of Bax and Bcl-2.
Germacrene
Germacrene, also known as (e,e)-germacra-1(10),4,7(11)-triene, is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Thus, germacrene is considered to be an isoprenoid lipid molecule. Germacrene can be found in turmeric, which makes germacrene a potential biomarker for the consumption of this food product. Germacrenes are a class of volatile organic hydrocarbons, specifically, sesquiterpenes. Germacrenes are typically produced in a number of plant species for their antimicrobial and insecticidal properties, though they also play a role as insect pheromones. Two prominent molecules are germacrene A and germacrene D .
24-Methylenecholesterol
24-Methylenecholesterol, also known as chalinasterol or ostreasterol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 24-methylenecholesterol is considered to be a sterol lipid molecule. 24-Methylenecholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 24-Methylenecholesterol is involved in the biosynthesis of steroids. 24-Methylenecholesterol is converted from 5-dehydroepisterol by 7-dehydrocholesterol reductase (EC 1.3.1.21). 24-Methylenecholesterol is converted into campesterol by delta24-sterol reductase (EC 1.3.1.72). 24-methylenecholesterol is a 3beta-sterol having the structure of cholesterol with a methylene group at C-24. It has a role as a mouse metabolite. It is a 3beta-sterol and a 3beta-hydroxy-Delta(5)-steroid. It is functionally related to a cholesterol. 24-Methylenecholesterol is a natural product found in Echinometra lucunter, Ulva fasciata, and other organisms with data available. A 3beta-sterol having the structure of cholesterol with a methylene group at C-24. Constituent of clams and oysters 24-Methylenecholesterol (Ostreasterol), a natural marine sterol, stimulates cholesterol acyltransferase in human macrophages. 24-Methylenecholesterol possess anti-aging effects in yeast. 24-methylenecholesterol enhances honey bee longevity and improves nurse bee physiology[1][2][3].
Campestanol
Campestanol is plant stanol. It can decrease the circulating LDL-cholesterol level by reducing intestinal cholesterol absorption. (PMID 8143759). Constituent of coffee and of pot marigold (Calendula officinalis)
Xanthoxyletin
Xanthoxyletin is a member of coumarins. It has a role as a metabolite. Xanthoxyletin is a natural product found in Zanthoxylum dipetalum, Murraya siamensis, and other organisms with data available. Isolated from Zanthoxylum americanum (prickly ash). Xanthoxyletin is found in lemon, sweet orange, and herbs and spices. Xanthoxyletin is found in herbs and spices. Xanthoxyletin is isolated from Zanthoxylum americanum (prickly ash). A natural product found in Clausena harmandiana.
(E)-Calamene
Calamene is a metabolite of plant Turnera diffusa. Turnera diffusa (Damiana, Mexican holly, Old Womans Broom) is a small shrub of the family Tuneraceae. T. diffusa is native to both Central and South America and now commercially cultivated in Bolivia and Mexico. The leaf includes volatile oils (1,8-cineole, p-cymene, alpha- and beta-pinene, thymol, alpha-copaene, and calamene); luteolin; tannins, flavonoids (arbutin, acacetin, apigenin and pinocembrin), beta-sitosterol, damianin, and the cyanogenic glycoside tetraphyllin B. (www.globinmed.com) (e)-calamene is also known as calamenene or 1,6-dimethyl-4-isopropyltetralin. (e)-calamene can be found in a number of food items such as guava, lovage, summer savory, and rosemary, which makes (e)-calamene a potential biomarker for the consumption of these food products (e)-calamene can be found primarily in urine.
(+)-alpha-Muurolene
(+)-alpha-Muurolene is isolated from various plant oils including Pinus mugo (dwarf mountain pine). Isolated from various plant oils including Pinus mugo (dwarf mountain pine)
Vidarabine
C10H13N5O4 (267.09674980000005)
A nucleoside antibiotic isolated from Streptomyces antibioticus. It has some antineoplastic properties and has broad spectrum activity against DNA viruses in cell cultures and significant antiviral activity against infections caused by a variety of viruses such as the herpes viruses, the vaccinia VIRUS and varicella zoster virus. [PubChem] J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors S - Sensory organs > S01 - Ophthalmologicals > S01A - Antiinfectives > S01AD - Antivirals D000890 - Anti-Infective Agents > D000998 - Antiviral Agents C471 - Enzyme Inhibitor > C29575 - DNA Polymerase Inhibitor C254 - Anti-Infective Agent > C281 - Antiviral Agent D009676 - Noxae > D000963 - Antimetabolites Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3]. Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3]. Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3].
Calamenene
Calamenene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
1-[(2R,3S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
1-beta-D-Arabinofuranosyluracil (Uracil 1-β-D-arabinofuranoside) isolated from the Caribbean sponge Tectitethya crypta, is a methoxyadenosine derivative. 1-beta-D-Arabinofuranosyluracil has demonstrated a diverse bioactivity profile including anti-inflammatory activity, analgesic and vasodilation properties[1]. 1-beta-D-Arabinofuranosyluracil reduces a proliferation of mouse lymphoma cells[2]. 1-beta-D-Arabinofuranosyluracil (Uracil 1-β-D-arabinofuranoside) isolated from the Caribbean sponge Tectitethya crypta, is a methoxyadenosine derivative. 1-beta-D-Arabinofuranosyluracil has demonstrated a diverse bioactivity profile including anti-inflammatory activity, analgesic and vasodilation properties[1]. 1-beta-D-Arabinofuranosyluracil reduces a proliferation of mouse lymphoma cells[2]. 1-beta-D-Arabinofuranosyluracil (Uracil 1-β-D-arabinofuranoside) isolated from the Caribbean sponge Tectitethya crypta, is a methoxyadenosine derivative. 1-beta-D-Arabinofuranosyluracil has demonstrated a diverse bioactivity profile including anti-inflammatory activity, analgesic and vasodilation properties[1]. 1-beta-D-Arabinofuranosyluracil reduces a proliferation of mouse lymphoma cells[2].
9-Arabinofuranosyladenine
C10H13N5O4 (267.09674980000005)
Germacrene A
Germacrene a is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Germacrene a can be found in sweet basil, which makes germacrene a a potential biomarker for the consumption of this food product.
Androsterol
Androsterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Androsterol can be found in dandelion, which makes androsterol a potential biomarker for the consumption of this food product.
Caffeine
N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics > N06BC - Xanthine derivatives D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058914 - Purinergic Antagonists D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D004791 - Enzyme Inhibitors > D010726 - Phosphodiesterase Inhibitors C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant CONFIDENCE standard compound; EAWAG_UCHEM_ID 303 EAWAG_UCHEM_ID 303; CONFIDENCE standard compound D - Dermatologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
Serotonin
C10H12N2O (176.09495819999998)
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists
Aristolone
Aristolone is a natural product found in Litophyton erectum, Aristolochia clematitis, and other organisms with data available. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1]. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1].
Cerevisterol
An ergostanoid that is (22E)-ergosta-7,22-diene substituted by hydroxy groups at positions 3, 5 and 6 (the 3beta,5alpha,6beta stereoisomer). It has been isolated from the fungus, Xylaria species. Cerevisterol is a steroid isolated from the fruiting bodies of Agaricus blazei[1]. Cerevisterol is a steroid isolated from the fruiting bodies of Agaricus blazei[1].
sitosterol
A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].
Stigmasterol
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.
3-Bromo-N-methyltyramine
C9H12BrNO (229.01022019999996)
A natural product found in Paramuricea clavata.
2-Bromo-N-methyltryptamine
C11H13BrN2 (252.02620380000002)
A natural product found in Paramuricea clavata.
Cholesterol
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].
6-bromo-N-methyltryptamine
C11H13BrN2 (252.02620380000002)
A natural product found in Paramuricea clavata.
1,3,7-trimethylisoguanine
A natural product found in Paramuricea clavata and Pseudodistoma cereum.
Caffeine
CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5866; ORIGINAL_PRECURSOR_SCAN_NO 5861 N - Nervous system > N06 - Psychoanaleptics > N06B - Psychostimulants, agents used for adhd and nootropics > N06BC - Xanthine derivatives D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058914 - Purinergic Antagonists D002491 - Central Nervous System Agents > D000697 - Central Nervous System Stimulants COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D004791 - Enzyme Inhibitors > D010726 - Phosphodiesterase Inhibitors C78272 - Agent Affecting Nervous System > C47795 - CNS Stimulant D - Dermatologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5880; ORIGINAL_PRECURSOR_SCAN_NO 5879 CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5893; ORIGINAL_PRECURSOR_SCAN_NO 5892 CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5916; ORIGINAL_PRECURSOR_SCAN_NO 5911 CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5923; ORIGINAL_PRECURSOR_SCAN_NO 5921 CONFIDENCE standard compound; INTERNAL_ID 1199; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5924; ORIGINAL_PRECURSOR_SCAN_NO 5922 CONFIDENCE standard compound; INTERNAL_ID 2766 MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; RYYVLZVUVIJVGH-UHFFFAOYSA-N_STSL_0030_Caffeine_0500fmol_180410_S2_LC02_MS02_97; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 1079 CONFIDENCE standard compound; INTERNAL_ID 50 CONFIDENCE standard compound; INTERNAL_ID 8666 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.568 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.560 CONFIDENCE standard compound; INTERNAL_ID 4089 IPB_RECORD: 3001; CONFIDENCE confident structure
Adenosine
C10H13N5O4 (267.09674980000005)
COVID info from PDB, Protein Data Bank, COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058913 - Purinergic Agonists D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents C - Cardiovascular system > C01 - Cardiac therapy Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Formula(Parent): C10H13N5O4; Bottle Name:Adenosine; PRIME Parent Name:Adenosine; PRIME in-house No.:0040 R0018, Purines MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OIRDTQYFTABQOQ_STSL_0143_Adenosine_0500fmol_180430_S2_LC02_MS02_33; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.113 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.109 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.097 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.096 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2621; CONFIDENCE confident structure Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2].
Stigmastanol
Stigmastanol is a 3-hydroxy steroid that is 5alpha-stigmastane which is substituted at the 3beta position by a hydroxy group. It has a role as an anticholesteremic drug and a plant metabolite. It is a 3-hydroxy steroid and a member of phytosterols. It derives from a hydride of a 5alpha-stigmastane. Stigmastanol is a natural product found in Alnus japonica, Dracaena cinnabari, and other organisms with data available. Stigmastanol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and a saturated bond in position 5-6 of the B ring. See also: Saw Palmetto (part of). A 3-hydroxy steroid that is 5alpha-stigmastane which is substituted at the 3beta position by a hydroxy group. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents C1907 - Drug, Natural Product > C28178 - Phytosterol > C68422 - Saturated Phytosterol D009676 - Noxae > D000963 - Antimetabolites 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. Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2]. Stigmastanol is the 6-amino derivative isolated from Hypericum riparium. Hypericum riparium A. Chev. is a Cameroonian medicinal plant belonging to the family Guttiferae[1][2].
Brassicasterol
An 3beta-sterol that is (22E)-ergosta-5,22-diene substituted by a hydroxy group at position 3beta. It is a phytosterol found in marine algae, fish, and rapeseed oil. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol 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. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].
Campesterol
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. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.
Serotonin
C10H12N2O (176.09495819999998)
D018377 - Neurotransmitter Agents > D018490 - Serotonin Agents > D017366 - Serotonin Receptor Agonists A primary amino compound that is the 5-hydroxy derivative of tryptamine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; QZAYGJVTTNCVMB_STSL_0135_Serotonin_8000fmol_180506_S2_LC02_MS02_147; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053
Cholestenone
Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop and efflux. Cholestenone may cause long-term functional defects in cells[1][2]. Cholestenone (4-Cholesten-3-one), the intermediate oxidation product of cholesterol, is metabolized primarily in the liver. Cholestenone is highly mobile in membranes and influences cholesterol flip-flop and efflux. Cholestenone may cause long-term functional defects in cells[1][2].
Vidarabine
C10H13N5O4 (267.09674980000005)
J - Antiinfectives for systemic use > J05 - Antivirals for systemic use > J05A - Direct acting antivirals > J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors S - Sensory organs > S01 - Ophthalmologicals > S01A - Antiinfectives > S01AD - Antivirals D000890 - Anti-Infective Agents > D000998 - Antiviral Agents C471 - Enzyme Inhibitor > C29575 - DNA Polymerase Inhibitor C254 - Anti-Infective Agent > C281 - Antiviral Agent D009676 - Noxae > D000963 - Antimetabolites Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3]. Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3]. Vidarabine (Ara-A) an antiviral agent which is active against herpes simplex and varicella zoster viruses[1][2]. Vidarabine has IC50s of 9.3 μg/ml for HSV-1 and 11.3 μg/ml for HSV-2[2]. Vidarabine also has anti-orthopoxvirus activity[3].
WE 20:6;O3
84-99-1
Eunicea sesquiterpenoid 2
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
Coprostanol
A member of the class of phytosterols that is 5beta-cholestane carrying a hydroxy substituent at the 3beta-position.
Dihydrocholesterol
5α-Cholestan-3β-ol is a derivitized steroid compound. 5α-Cholestan-3β-ol is a derivitized steroid compound.
Eunicea sesquiterpenoid 7
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.
Avenasterol
A stigmastane sterol that is 5alpha-stigmastane carrying a hydroxy group at position 3beta and double bonds at positions 7 and 24.
(1s,3r,5r,6r,9r)-6-hydroxy-6,10,10-trimethyltricyclo[7.2.0.0³,⁵]undecan-2-one
2-[(1s,3e,7e,11e)-4,8,12-trimethylcyclotetradeca-3,7,11-trien-1-yl]propan-2-ol
(1r,3as,3br,4s,5ar,7s,9as,9br,11ar)-4,7,9b-trihydroxy-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-dodecahydro-1h-cyclopenta[a]phenanthren-5-one
(1s,3as,3br,9ar,9bs,11as)-1-hydroxy-1-[(2r,3r,6r)-2-hydroxy-6-isopropyloxan-3-yl]-9a,11a-dimethyl-2h,3h,3ah,3bh,4h,5h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one
7,11,15-trimethyl-3-methylidenehexadecane-1,2-diol
(1r,2s,3r,6r,7r,8r,9r,13z)-9-(acetyloxy)-6-isopropyl-3,9,13-trimethyl-12-oxo-15-oxatricyclo[6.6.1.0²,⁷]pentadec-13-en-3-yl acetate
2-[(2z)-3,6,10-trimethyl-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-ylidene]acetaldehyde
(1r,2r,6r,7r,8r,9s,12z)-6-isopropyl-9,13-dimethyl-3-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadec-12-en-9-yl acetate
3,10-dimethyl-4h,7h,8h,11h-cyclodeca[b]furan-6-yl acetate
[(2r,3s,4r,5r,6s)-3,4-bis(acetyloxy)-5-hydroxy-6-{4-hydroxy-2-[(2e,6e,9e)-11-methoxy-3,7,11-trimethyldodeca-2,6,9-trien-1-yl]-5-methylphenoxy}oxan-2-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
10-hydroperoxy-6,15a-dihydroxy-3,6,10,14-tetramethyl-7h,11h,12h,13h,14h-cyclotetradeca[b]furan-2,15-dione
(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
(3s,7r,10r,12r,13r)-12-hydroxy-3,7,13-trimethyl-10-(prop-1-en-2-yl)cyclotetradecane-1,6-dione
(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
2-[(1s,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-5-methylhex-3-en-2-yl]cyclopentyl]ethyl acetate
2-[(3ar,12as)-3a,6,10-trimethyl-3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-ol
n-methyl-5-(n-methylformamido)-3-[(2e,6e,11z)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl]imidazole-4-carboximidic acid
4,9,12-trimethyl-15-(propan-2-ylidene)-5-oxatricyclo[10.3.0.0⁴,⁶]pentadec-9-en-14-one
(1r,2s,3r,6r,7r,8r,9r,12s)-9,12-bis(acetyloxy)-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate
9a,11a-dimethyl-1-(5-methylhex-3-en-2-yl)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
(3ar,9r,12ar)-9-hydroperoxy-1-isopropyl-3a,6,10-trimethyl-1h,3h,4h,7h,8h,9h,12h,12ah-cyclopenta[11]annulen-2-one
(1r,3as,3bs,4r,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5s)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-4,5,5a,7-tetrol
(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
(3e,5e,7r,8e)-3,7,11-trimethyldodeca-1,3,5,8,10-pentaene
(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
(5z,8z,11z)-n-[2-(4-hydroxyphenyl)ethyl]tetradeca-5,8,11-trienimidic acid
6,9a,11a-trimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol
3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,5h,6h,7h,8h,11h,12h,12ah-cyclopenta[11]annulene-2,4-dione
4-isopropyl-7,11-dimethyl-2-(prop-1-en-2-yl)cyclododeca-3,7-dien-1-one
(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]
(1s,2r,5s,7s,9r,10r,11s,12s,15r,16r)-2,16-dimethyl-15-[(2r)-6-methylheptan-2-yl]-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecane-5,10-diol
(1r,3as,3br,5as,7s,9as,9bs,11ar)-1-ethenyl-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol
(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
1,3-dimethyl-7-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10-trien-1-yl)purine-2,6-dione
(1r,3as,3bs,5r,5ar,7s,9ar,9bs,11ar)-1-[(2r,5s)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthrene-5,5a,7-triol
(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
3,5',5',6,10-pentamethyl-3a,4,5,8,9,11a-hexahydro-3h-spiro[cyclodeca[b]furan-2,2'-oxolane]
7-[(4-{[3-(acetyloxy)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy]-11a-methyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-9a-carboxylic acid
9-hydroxy-1,10-dimethyl-5,14-dimethylidene-6-oxo-7,18-dioxatricyclo[13.2.1.0⁴,⁸]octadecan-2-yl acetate
(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
6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol
(1s,3as,3br,5as,9as,9bs,11as)-1-hydroxy-1-[(2r,3r,6r)-2-hydroxy-6-isopropyloxan-3-yl]-9a,11a-dimethyl-dodecahydro-2h-cyclopenta[a]phenanthren-7-one
(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,2s,3r,6r,7r,8r,9r)-9-(acetyloxy)-6-isopropyl-3,9-dimethyl-13-methylidene-12-oxo-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate
(1r,4e,8e,12s,13r)-12-hydroxy-4,8,12-trimethyl-16-methylidene-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-15-one
(6s,7e,9e)-2,6,10-trimethyldodeca-2,7,9,11-tetraen-6-ol
(3z,5z,9e,13r)-6-isopropyl-3,9,13-trimethylcyclotetradeca-3,5,9-trien-1-one
(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
2-{3a,6,10-trimethyl-1h,2h,3h,4h,7h,8h,11h-cyclopenta[11]annulen-1-yl}propan-2-ol
(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
4-(hydroxymethyl)-10,14-dimethyl-7-(prop-1-en-2-yl)-15-oxabicyclo[12.1.0]pentadeca-4,10-dien-6-ol
(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
9a,11a-dimethyl-1-{1-[2-methyl-2-(3-methylbutan-2-yl)cyclopropyl]ethyl}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthrene-7,9b-diol
(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
n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)imidazole-4-carboximidic acid
(2s,3z,7e,11r)-4-isopropyl-7,11-dimethyl-2-(prop-1-en-2-yl)cyclododeca-3,7-dien-1-one
(1r,3as,3bs,5as,7s,9as,9bs,10r,11ar)-1-ethenyl-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-10-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
(2s,4e,6r)-6-[(1r,3as,3bs,5ar,7s,9ar,9bs,11ar)-5a,7-dihydroxy-9a,11a-dimethyl-5-oxo-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylhept-4-en-1-yl acetate
(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
7-{2-[3-(acetyloxy)oct-1-en-1-yl]-5-oxocyclopent-3-en-1-yl}hept-5-enoic acid
1,3-dimethyl-7-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10-trien-1-yl)-2h-purin-6-one
(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,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
2,6-dihydroxy-2,6,10-trimethyl-15-methylidene-13,18-dioxatricyclo[9.6.1.0¹²,¹⁶]octadec-4-en-14-one
6,10-dimethyl-5-(6-methyl-5-methylideneheptan-2-yl)-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol
9a,11a-dimethyl-1-{1-[2-methyl-2-(3-methylbutan-2-yl)cyclopropyl]ethyl}-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-7,10-diol
6-({1-ethenyl-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}oxy)-4,5-dihydroxyoxan-3-yl acetate
(4ar,7ar)-3,8-dimethyl-5-methylidene-4h,4ah,6h,7h,7ah-azuleno[6,5-b]furan
(3ar,4as,8r,8ar,10as)-8-hydroxy-3a,8a-dimethyl-5-methylidene-1-(propan-2-ylidene)-octahydro-3h-cyclohexa[f]azulen-2-one
2-[2-(4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl)-1-methyl-5-(5-methylhex-3-en-2-yl)cyclopentyl]ethyl acetate
9,12-bis(acetyloxy)-6-isopropyl-3,9-dimethyl-13-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl acetate
(2s,3s,4r,5r)-2-{[(3e,5e)-6-[(1s,3r,4r)-4-ethenyl-4-methyl-3-(prop-1-en-2-yl)cyclohexyl]-2-methylhepta-3,5-dien-2-yl]oxy}oxane-3,4,5-triol
11a-methyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,3bh,4h,5h,8h,9h,9ah,9bh,10h,11h-cyclopenta[a]phenanthren-7-one
(2s,3s,4s)-2-methyl-5-oxo-4-tetradecyloxolan-3-yl acetate
(1r,4r,6r,9s,10s)-4,12,12-trimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecane-9-carboxylic acid
5-(5-ethyl-6-methylheptan-2-yl)-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol
(1s,2r,5r,6r,9r,10r,13s,15s)-5-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol
n-methyl-5-(n-methylformamido)-3-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10-trien-1-yl)imidazole-4-carboximidic acid
2-[(1s,2s,3r,4r,7r,8s,11s,14r)-4,11,14-tris(acetyloxy)-6,14-dimethyl-10-methylidene-15-oxatricyclo[6.6.1.0²,⁷]pentadec-5-en-3-yl]propan-2-yl acetate
(1r,3as,3bs,5as,9as,9bs,10r,11ar)-1-ethenyl-9a,11a-dimethyl-7-oxo-tetradecahydrocyclopenta[a]phenanthren-10-yl acetate
(2s,3s,4s)-4-hexadecyl-2-methyl-5-oxooxolan-3-yl acetate
(1r,3ar,12ar)-1-isopropyl-3a,6,10-trimethyl-1h,3h,7h,8h,11h,12h,12ah-cyclopenta[11]annulene-2,4-dione
(1r,3as,3bs,5as,9as,9bs,10r,11ar)-1-ethenyl-7,7-dimethoxy-9a,11a-dimethyl-tetradecahydrocyclopenta[a]phenanthren-10-yl acetate
(1r,4s,7s,8e,12r)-9-isopropyl-4,12-dimethyl-7-(prop-1-en-2-yl)-13-oxabicyclo[10.1.0]tridec-8-en-6-one
(1r,4r,6r,10s,12r)-12-(hydroxymethyl)-4,12-dimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-9-one
2-[(1s,2r,5r)-2-[(4s,4as,6s,8as)-4,6-dihydroxy-8a-methyl-1-oxo-4,4a,5,6,7,8-hexahydronaphthalen-2-yl]-1-methyl-5-[(2r,3e)-6-methylhept-3-en-2-yl]cyclopentyl]ethyl acetate
(1r,3as,12as)-3a,6,10-trimethyl-1-(prop-1-en-2-yl)-2h,3h,4h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-ol
(4as,7as)-3-methyl-6,8-dimethylidene-4h,4ah,5h,7h,7ah,9h-azuleno[6,5-b]furan
3,11-dimethyl-7-methylidenedodeca-1,3,10-trien-6-yl acetate
1,3-dimethyl-7-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)purine-2,6-dione
2-({1-ethenyl-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}oxy)oxane-3,4,5-triol
3-methyl-7-(3,7,11,15-tetramethyl-13-oxohexadeca-2,6,11-trien-1-yl)purin-6-one
C26H38N4O2 (438.29946079999996)
(3s,4r)-3-hexadecyl-4-hydroxy-5-methylideneoxolan-2-one
(3as,6s,12ar)-3a,6,10-trimethyl-1-(propan-2-ylidene)-3h,5h,6h,7h,8h,11h,12h,12ah-cyclopenta[11]annulene-2,4-dione
(2s,3s,4r,5r)-2-{[(1r,4r,4as,6r,8ar)-6-[(2z,4e)-6-hydroxy-6-methylhepta-2,4-dien-2-yl]-4,4a-dimethyl-octahydro-1h-naphthalen-1-yl]oxy}-4,5-dihydroxyoxan-3-yl acetate
3,13-dihydroxy-6-isopropyl-12-methoxy-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-9-yl acetate
[(1s,4e,6s,7r,10e,14s)-6-hydroxy-10,14-dimethyl-7-(prop-1-en-2-yl)-15-oxabicyclo[12.1.0]pentadeca-4,10-dien-4-yl]methyl acetate
(3ar,12ar)-3a,6,10-trimethyl-1-(propan-2-ylidene)-2h,3h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-4-one
[3,4-bis(acetyloxy)-5-hydroxy-6-[4-hydroxy-5-methyl-2-(3,7,11-trimethyl-9-oxododeca-2,6-dien-1-yl)phenoxy]oxan-2-yl]methyl acetate
6-hydroperoxy-2-hydroxy-2,6,10-trimethyl-15-methylidene-13,18-dioxatricyclo[9.6.1.0¹²,¹⁶]octadec-4-en-14-one
(5e)-7-[(1r,2r)-2-[(2e)-oct-2-en-1-yl]-5-oxocyclopent-3-en-1-yl]hept-5-enoic acid
[3,4-bis(acetyloxy)-5-hydroxy-6-[4-hydroxy-2-(9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl)-5-methylphenoxy]oxan-2-yl]methyl acetate
(4e,8z)-12-hydroxy-4,8,12-trimethyl-16-methylidene-15-oxo-14-oxabicyclo[11.3.1]heptadeca-4,8-dien-2-yl acetate
(1s,2r,5s,7s,9r,10r,11s,12s,15r,16r)-2,16-dimethyl-15-[(2r)-6-methyl-5-methylideneheptan-2-yl]-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecane-5,10-diol
(1r,9s)-9-[(2e,4e)-6-hydroxy-6-methylhepta-2,4-dien-2-yl]-6-methyl-2-methylidenecyclodec-5-en-1-ol
(4as,7as)-3-methyl-5,8-dimethylidene-4h,4ah,6h,7h,7ah,9h-azuleno[6,5-b]furan
(1s,2r,4s,8r,9r,10s,15r)-2-hydroxy-1,10-dimethyl-5,14-dimethylidene-6-oxo-7,18-dioxatricyclo[13.2.1.0⁴,⁸]octadecan-9-yl acetate
(1r,2r,6r,7r,8r,9r,12e)-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadeca-3,12-dien-9-ol
2-(acetyloxy)-2,6,10-trimethyldodeca-3,7,9,11-tetraen-5-yl acetate
[(1e,3s,4r,7e,12s)-3-(acetyloxy)-12-hydroxy-7,11-dimethyl-4-(prop-1-en-2-yl)cyclotetradeca-1,7,10-trien-1-yl]methyl acetate
(2s,7s,11s)-7,11,15-trimethyl-3-methylidenehexadecane-1,2-diol
5-hydroxy-3-(icosa-6,9-dien-1-yl)-5-methylfuran-2-one
(1r,3s,5s,8s,10s,14s,15r,16s)-15-hydroxy-5,10,14-trimethyl-19-methylidene-4,9,17-trioxatetracyclo[14.3.0.0³,⁵.0⁸,¹⁰]nonadecan-18-one
3,6,10-trimethyl-2-(3-methylbut-1-en-1-yl)-3h,3ah,4h,5h,8h,9h,11ah-cyclodeca[b]furan-2-ol
(2s,3r,4e,6r)-6-[(1r,3as,3bs,5ar,7s,9ar,9bs,11ar)-5a,7-dihydroxy-9a,11a-dimethyl-5-oxo-dodecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2,3-dimethylhept-4-en-1-yl acetate
n-[2-(4-hydroxyphenyl)ethyl]tetradeca-5,8,11-trienimidic acid
2-({1-ethenyl-7-hydroxy-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-6-yl}oxy)-5-hydroxy-4-methoxy-6-methyloxan-3-yl acetate
1,3-dimethyl-7-[(2e,6e,10e)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10-trien-1-yl]purine-2,6-dione
(1s,2r,4s,8r,9s,10r,15r)-9-hydroxy-1,10-dimethyl-5,14-dimethylidene-6-oxo-7,18-dioxatricyclo[13.2.1.0⁴,⁸]octadecan-2-yl acetate
[(2r,3s,4r,5r,6s)-3,4-bis(acetyloxy)-5-hydroxy-6-{4-hydroxy-2-[(2e,6e,9r)-9-hydroxy-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]-5-methylphenoxy}oxan-2-yl]methyl acetate
9a,11a-dimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-tetradecahydrocyclopenta[a]phenanthrene-4,5,5a,7-tetrol
6-ethenyl-3,5',5',6-tetramethyl-7-(prop-1-en-2-yl)-hexahydrospiro[1-benzofuran-2,2'-oxolane]
2-{6,10,14-trimethyl-15-oxabicyclo[12.1.0]pentadeca-6,10-dien-3-yl}prop-2-enal
[(2r,3s,4r,5r,6s)-3,4-bis(acetyloxy)-5-hydroxy-6-{4-hydroxy-5-methyl-2-[(2e,6e)-3,7,11-trimethyldodeca-2,6,10-trien-1-yl]phenoxy}oxan-2-yl]methyl acetate
1-ethenyl-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol
4-isopropyl-1,9-dimethyl-7-oxo-6-(prop-1-en-2-yl)-13-oxabicyclo[10.1.0]tridec-4-en-3-yl acetate
2-({1-ethenyl-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl}oxy)-3,5-dihydroxyoxan-4-yl acetate
(1r,3as,3bs,5as,6s,7s,9ar,9bs,11ar)-1-[(2r,5s)-5,6-dimethylheptan-2-yl]-6,9a,11a-trimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol
3-methyl-7-[(2e,6e,10e)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10-trien-1-yl]purin-6-one
C26H38N4O2 (438.29946079999996)