NCBI Taxonomy: 3028843

Thymidine

C10H14N2O5 (242.0902674)

Deoxythymidine, also known as 2-deoxy-5-methyluridine or 5-methyl-2-deoxyuridine, is a member of the class of compounds known as pyrimidine 2-deoxyribonucleosides. Pyrimidine 2-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxythymidine is soluble (in water) and a very weakly acidic compound (based on its pKa). Deoxythymidine can be synthesized from thymine. Deoxythymidine is also a parent compound for other transformation products, including but not limited to, tritiated thymidine, alpha-tritiated thymidine, and 5,6-dihydrothymidine. Deoxythymidine can be found in a number of food items such as butternut squash, mammee apple, catjang pea, and climbing bean, which makes deoxythymidine a potential biomarker for the consumption of these food products. Deoxythymidine can be found primarily in most biofluids, including blood, amniotic fluid, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Deoxythymidine exists in all living species, ranging from bacteria to humans. In humans, deoxythymidine is involved in the pyrimidine metabolism. Deoxythymidine is also involved in few metabolic disorders, which include beta ureidopropionase deficiency, dihydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and UMP synthase deficiency (orotic aciduria). Moreover, deoxythymidine is found to be associated with canavan disease and degenerative disc disease. Thymidine (deoxythymidine; other names deoxyribosylthymine, thymine deoxyriboside) is a pyrimidine deoxynucleoside. Deoxythymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in G1/early S phase . Thymidine, also known as deoxythymidine or deoxyribosylthymine or thymine deoxyriboside, is a pyrimidine deoxynucleoside. It consists of the nucleobase thymine attached to deoxyribose through a beta N- glycosidic bond. Thymidine also belongs to the class of organic compounds known as pyrimidine 2-deoxyribonucleosides. Pyrimidine 2-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2. Deoxythymidine (or thymidine) is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. Therefore, thymidine is essential to all life. Indeed, thymidine exists in all living species, ranging from bacteria to plants to humans. Within humans, thymidine participates in a number of enzymatic reactions. In particular, thymidine can be biosynthesized from 5-thymidylic acid through its interaction with the enzyme cytosolic purine 5-nucleotidase. In addition, thymidine can be converted into 5-thymidylic acid; which is catalyzed by the enzyme thymidine kinase. Deoxythymidine can be phosphorylated with one, two or three phosphoric acid groups, creating dTMP (deoxythymidine monophosphate), dTDP, or dTTP (for the di- and tri- phosphates, respectively). dTMP can be incorporated into DNA via DNA polymerases. In cell biology, thymidine can be used to synchronize the cells in S phase. Derivatives of thymidine are used in a number of drugs, including Azidothymidine (AZT), which is used in the treatment of HIV infection. AZT inhibits the process of reverse transcription in the human immunodeficiency virus. Thymidine is a pyrimidine 2-deoxyribonucleoside having thymine as the nucleobase. It has a role as a metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. It is functionally related to a thymine. It is an enantiomer of a telbivudine. Thymidine is a pyrimidine deoxynucleoside. Thymidine is the DNA nucleoside T, which pairs with deoxyadenosine (A) in double-stranded DNA. In cell biology it is used to synchronize the cells in S phase. Thymidine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Thymidine is a natural product found in Fritillaria thunbergii, Saussurea medusa, and other organisms with data available. Thymidine is a pyrimidine nucleoside that is composed of the pyrimidine base thymine attached to the sugar deoxyribose. As a constituent of DNA, thymidine pairs with adenine in the DNA double helix. (NCI04) Thymidine is a metabolite found in or produced by Saccharomyces cerevisiae. A nucleoside in which THYMINE is linked to DEOXYRIBOSE. A pyrimidine 2-deoxyribonucleoside having thymine as the nucleobase. KEIO_ID T014; [MS2] KO009272 KEIO_ID T014 Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3]. Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3].

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].

Tryptamine

C10H12N2 (160.1000432)

Tryptamine, also known as TrpN, is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine. Both Clostridium sp. and Ruminococcus sp. have been found to convert tryptophan into tryptamine (PMID: 30120222). Tryptamine is a monoamine compound that is a common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, acerola, Japanese walnuts, custard apples, and green zucchinis. This could make tryptamine a potential biomarker for the consumption of these foods. Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is an aminoalkylindole, an indole alkaloid, an aralkylamino compound and a member of tryptamines. It is a conjugate base of a tryptaminium. Tryptamine is a natural product found in Mus musculus, Prosopis glandulosa, and other organisms with data available. Occurs widely in plants, especies Lens esculenta (lentil) and the fungi Coprinus micaceus (glistening ink cap) An aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. KEIO_ID T031

Caffeine

C8H10N4O2 (194.080372)

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).

Luteolin

C15H10O6 (286.047736)

Luteolin is a naturally occurring flavonoid. (PMID:17168665). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445). Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate. Luteolin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Luteolin is a naturally-occurring flavonoid, with potential anti-oxidant, anti-inflammatory, apoptosis-inducing and chemopreventive activities. Upon administration, luteolin scavenges free radicals, protects cells from reactive oxygen species (ROS)-induced damage and induces direct cell cycle arrest and apoptosis in tumor cells. This inhibits tumor cell proliferation and suppresses metastasis. 5,7,3,4-tetrahydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. Flavone v. widespread in plant world; found especies in celery, peppermint, rosemary, thyme and Queen Annes Lace leaves (wild carrot). Potential nutriceutical. Luteolin is found in many foods, some of which are soy bean, ginger, abalone, and swiss chard. Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 361; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 48 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

Palmitic acid

C16H32O2 (256.2402172)

Palmitic acid, also known as palmitate or hexadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, palmitic acid is considered to be a fatty acid lipid molecule. Palmitic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Palmitic acid can be found in a number of food items such as sacred lotus, spinach, shallot, and corn salad, which makes palmitic acid a potential biomarker for the consumption of these food products. Palmitic acid can be found primarily in most biofluids, including feces, sweat, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Palmitic acid exists in all living species, ranging from bacteria to humans. In humans, palmitic acid is involved in several metabolic pathways, some of which include alendronate action pathway, rosuvastatin action pathway, simvastatin action pathway, and cerivastatin action pathway. Palmitic acid is also involved in several metabolic disorders, some of which include hypercholesterolemia, familial lipoprotein lipase deficiency, ethylmalonic encephalopathy, and carnitine palmitoyl transferase deficiency (I). Moreover, palmitic acid is found to be associated with schizophrenia. Palmitic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Palmitic acid can also be found in meats, cheeses, butter, and dairy products. Palmitate is the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4) . Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation (DrugBank). Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30\\\% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. Hexadecanoic acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid. It has a role as an EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. Palmitic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Palmitic Acid is a saturated long-chain fatty acid with a 16-carbon backbone. Palmitic acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat. Palmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. It occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin and is usually obtained from palm oil, which is widely distributed in plants. Palmitic acid is used in determination of water hardness and is an active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging and as an ultrasound contrast medium. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. A straight-chain, sixteen-carbon, saturated long-chain fatty acid. Palmitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-10-3 (retrieved 2024-07-01) (CAS RN: 57-10-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Campesterol

C28H48O (400.37049579999996)

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

C29H48O (412.37049579999996)

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

beta-Elemene

C15H24 (204.1877904)

(-)-beta-elemene is the (-)-enantiomer of beta-elemene that has (1S,2S,4R)-configuration. It has a role as an antineoplastic agent. beta-Elemene is a natural product found in Xylopia sericea, Eupatorium cannabinum, and other organisms with data available. Beta-elemene is one of the isomers of elemene, a lipid soluble sesquiterpene and the active component isolated from the Chinese medicinal herb Rhizoma zedoariae with potential antineoplastic and chemopreventive activities. Although the exact mechanism of action through which beta-elemene exerts its effect has yet to be fully elucidated, this agent appears to induce apoptosis through different mechanisms of action and induces cell cycle arrest at different stages based on the tumor cell type involved. Beta-elemene may sensitize cancer cells to other chemotherapeutic agents. See also: Cannabis sativa subsp. indica top (part of). Beta-elemene, also known as B-elemen or 2,4-diisopropenyl-1-methyl-1-vinylcyclohexane, is a member of the class of compounds known as elemane sesquiterpenoids. Elemane sesquiterpenoids are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. Beta-elemene is a fresh, herbal, and waxy tasting compound and can be found in a number of food items such as lovage, anise, spearmint, and orange mint, which makes beta-elemene a potential biomarker for the consumption of these food products. Beta-elemene can be found primarily in saliva. beta-Elemene belongs to the class of organic compounds known as elemane sesquiterpenoids. These are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively. beta-Elemene can be found in herbs, spices, and root vegetables, which makes beta-elemene a potential biomarker for the consumption of these food products. It is a constituent of sweet flag, juniper oils, and Mentha species. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis.

Stigmastanol

C29H52O (416.4017942)

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].

Furanodiene

C15H20O (216.151407)

Furanodiene is a germacrane sesquiterpenoid. Furanodiene is a natural product found in Curcuma amada, Lactarius chrysorrheus, and other organisms with data available. Furanodiene is a constituent of Curcuma zedoaria (zedoary) Constituent of Curcuma zedoaria (zedoary)

Serotonin

C10H12N2O (176.0949582)

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

C27H44O (384.3391974)

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].

Eicosapentaenoic acid

C20H30O2 (302.224568)

Icosapent, also known as icosapentaenoate or (5z,8z,11z,14z,17z)-eicosapentaenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, icosapent is considered to be a fatty acid lipid molecule. Icosapent is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Icosapent can be found in a number of food items such as barley, sacred lotus, white lupine, and rape, which makes icosapent a potential biomarker for the consumption of these food products. Icosapent can be found primarily in blood, feces, sweat, and urine, as well as throughout most human tissues. In humans, icosapent is involved in the alpha linolenic acid and linoleic acid metabolism. Moreover, icosapent is found to be associated with essential hypertension and hypertension. Ethyl eicosapentaenoic acid (E-EPA, icosapent ethyl) is a derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA) that is used in combination with changes in diet to lower triglyceride levels in adults with severe (≥ 500 mg/dL) hypertriglyceridemia. This was the second class of fish oil-based drug to be approved for use as a drug and was approved by the FDA in 2012. These fish oil drugs are similar to fish oil dietary supplements but the ingredients are better controlled and have been tested in clinical trials . The anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40 (DrugBank). Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. Eicosapentaenoic acid is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). Its systematic chemical name is all-cis-5,8,11,14,17-icosapentaenoic acid. It also has the trivial name timnodonic acid. Chemically, EPA is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end. Because of the presence of double bonds, EPS is a polyunsaturated fatty acid. Metabolically it acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3, and leukotriene-5 groups. It is found in fish oils of cod liver, herring, mackerel, salmon, menhaden, and sardine. It is also found in human breast milk (Wikipedia). Chemical was purchased from CAY 90110 (Lot. 0443819-6); Diagnostic ions: 301.2, 257.1, 202.9 CONFIDENCE standard compound; INTERNAL_ID 305 Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3]. Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3].

Sphingosine

C18H37NO2 (299.2824142)

Sphingosine, also known as (4E)-sphingenine or sphing-4-enine, belongs to the class of organic compounds known as 1,2-aminoalcohols. These are organic compounds containing an alkyl chain with an amine group bound to the C1 atom and an alcohol group bound to the C2 atom. Sphingosine is an 18-carbon amino alcohol with an unsaturated hydrocarbon chain, which forms a primary part of sphingolipids. Sphingolipids are a class of cell membrane lipids that include sphingomyelin. Thus, sphingosine is considered to be a sphingoid base lipid. Sphingosine is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Sphingosine is found in all living organisms ranging from bacteria to plants to humans. Sphingosine is synthesized from palmitoyl CoA and serine in a condensation required to yield dehydrosphingosine. Dehydrosphingosine is then reduced by NADPH to dihydrosphingosine (sphinganine), and finally oxidized by FAD to sphingosine. Within humans and other mammals, sphingosine participates in a number of enzymatic reactions. In particular, sphingosine can be converted into sphingosine 1-phosphate through its interaction with the enzyme sphingosine kinase 2. sphingosine 1-phosphate is an important signaling molecule. In addition, sphingosine can be biosynthesized from sphingosine 1-phosphate; which is mediated by the enzyme sphingosine-1-phosphate phosphatase 2. Sphingosine and its derivative sphinganine are the major bases of the sphingolipids in mammals. In humans, sphingosine is involved in globoid cell leukodystrophy. Cerebrosides is the common name for a group of glycosphingolipids called monoglycosylceramides which are important components in animal muscle and nerve cell membranes. They consist of a ceramide with a single sugar residue at the 1-hydroxyl moiety. The sugar residue can be either glucose or galactose; the two major types are therefore called glucocerebrosides and galactocerebrosides. Galactocerebrosides are typically found in neural tissue, while glucocerebrosides are found in other tissues. Sphingosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=123-78-4 (retrieved 2024-07-16) (CAS RN: 123-78-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator[1][2][3][4]. D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator[1][2][3][4].

N-Methyltryptamine

C11H14N2 (174.1156924)

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)

Pregnenolone

C21H32O2 (316.24021719999996)

Pregnenolone is a derivative of cholesterol, the product of cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1. This reaction consists of three consecutive monooxygenations, a 22-hydroxylation, a 20-hydroxylation, and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum, and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted into pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell, angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and many steps in the transport to the inner membrane. Thus, it exerts a powerful control over the use of cholesterol for aldosterone production (PMID: 17222962, 15823613, 16632873, 15134809). C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3]. Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

Prostaglandin E2

C20H32O5 (352.2249622)

The naturally occurring prostaglandin E2 (PGE2) is known in medicine as dinoprostone, and it is the most common and most biologically active of the mammalian prostaglandins. It has important effects during labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bones mineralized matrix). PGE2 is also the prostaglandin that ultimately induces fever. PGE2 has been shown to increase vasodilation and cAMP production, enhance the effects of bradykinin and histamine, and induce uterine contractions and platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus, decreasing T-cell proliferation and lymphocyte migration, and activating the secretion of IL-1α and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation, and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC). PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype (PMID:16978535). Prostaglandins are 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 and are 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 signalling pathways. Dinoprostone is a naturally occurring prostaglandin E2 (PGE2) and the most common and most biologically active of the mammalian prostaglandins. It has important effects in labour and also stimulates osteoblasts to release factors which stimulate bone resorption by osteoclasts (a type of bone cell that removes bone tissue by removing the bones mineralized matrix). PGE2 has been shown to increase vasodilation and cAMP production, to enhance the effects of bradykinin and histamine, induction of uterine contractions and of platelet aggregation. PGE2 is also responsible for maintaining the open passageway of the fetal ductus arteriosus; decreasing T-cell proliferation and lymphocyte migration and activating the secretion of IL-1α and IL-2. PGE2 exhibits both pro- and anti-inflammatory effects, particularly on dendritic cells (DC). Depending on the nature of maturation signals, PGE2 has different and sometimes opposite effects on DC biology. PGE2 exerts an inhibitory action, reducing the maturation of DC and their ability to present antigen. PGE2 has also been shown to stimulate DC and promote IL-12 production when given in combination with TNF-alpha. PGE2 is an environmentally bioactive substance. Its action is prolonged and sustained by other factors especially IL-10. It modulates the activities of professional DC by acting on their differentiation, maturation and their ability to secrete cytokines. PGE2 is a potent inducer of IL-10 in bone marrow-derived DC (BM-DC), and PGE2-induced IL-10 is a key regulator of the BM-DC pro-inflammatory phenotype. (PMID: 16978535) G - Genito urinary system and sex hormones > G02 - Other gynecologicals > G02A - Uterotonics > G02AD - Prostaglandins Chemical was purchased from CAY14010, (Lot 0410966-34); Diagnostic ions: 351.8, 333.1, 271.1, 188.9 D012102 - Reproductive Control Agents > D010120 - Oxytocics C78568 - Prostaglandin Analogue Prostaglandin E2 (PGE2) is a hormone-like substance that participate in a wide range of body functions such as the contraction and relaxation of smooth muscle, the dilation and constriction of blood vessels, control of blood pressure, and modulation of inflammation.

Arachidonic acid

C20H32O2 (304.24021719999996)

Arachidonic acid is a polyunsaturated, essential fatty acid that has a 20-carbon chain as a backbone and four cis-double bonds at the C5, C8, C11, and C14 positions. It is found in animal and human fat as well as in the liver, brain, and glandular organs, and is a constituent of animal phosphatides. It is synthesized from dietary linoleic acid. Arachidonic acid mediates inflammation and the functioning of several organs and systems either directly or upon its conversion into eicosanoids. Arachidonic acid in cell membrane phospholipids is the substrate for the synthesis of a range of biologically active compounds (eicosanoids) including prostaglandins, thromboxanes, and leukotrienes. These compounds can act as mediators in their own right and can also act as regulators of other processes, such as platelet aggregation, blood clotting, smooth muscle contraction, leukocyte chemotaxis, inflammatory cytokine production, and immune function. Arachidonic acid can be metabolized by cytochrome p450 (CYP450) enzymes into 5,6-, 8,9-, 11,12-, and 14,15-epoxyeicosatrienoic acids (EETs), their corresponding dihydroxyeicosatrienoic acids (DHETs), and 20-hydroxyeicosatetraenoic acid (20-HETE). The production of kidney CYP450 arachidonic acid metabolites is altered in diabetes, pregnancy, hepatorenal syndrome, and in various models of hypertension, and it is likely that changes in this system contribute to the abnormalities in renal function that are associated with many of these conditions. Phospholipase A2 (PLA2) catalyzes the hydrolysis of the sn-2 position of membrane glycerophospholipids to liberate arachidonic acid (PMID: 12736897, 12736897, 12700820, 12570747, 12432908). The beneficial effects of omega-3 fatty acids are believed to be due in part to selective alteration of arachidonate metabolism that involves cyclooxygenase (COX) enzymes (PMID: 23371504). 9-Oxononanoic acid (9-ONA), one of the major products of peroxidized fatty acids, was found to stimulate the activity of phospholipase A2 (PLA2), the key enzyme to initiate the arachidonate cascade and eicosanoid production (PMID: 23704812). Arachidonate lipoxygenase (ALOX) enzymes metabolize arachidonic acid to generate potent inflammatory mediators and play an important role in inflammation-associated diseases (PMID: 23404351). Essential fatty acid. Constituent of many animal phospholipids Arachidonic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=506-32-1 (retrieved 2024-07-15) (CAS RN: 506-32-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Arachidonic acid is an essential fatty acid and a major constituent of biomembranes. Arachidonic acid is an essential fatty acid and a major constituent of biomembranes.

Docosahexaenoic acid

C22H32O2 (328.2402172)

Docosahexaenoic acid (DHA) is an omega-3 essential fatty acid. Chemically, DHA is a carboxylic acid with a 22-carbon chain and six cis- double bonds with the first double bond located at the third carbon from the omega end. DHA is most often found in fish oil. It is a major fatty acid in sperm and brain phospholipids, especially in the retina. Dietary DHA can reduce the level of blood triglycerides in humans, which may reduce the risk of heart disease (Wikipedia). Docosahexaenoic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Extensively marketed as a dietary supplement in Japan [DFC]. Doconexent is found in many foods, some of which are mung bean, fruit preserve, northern pike, and snapper. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Docosahexaenoic Acid (DHA) is an omega-3 fatty acid abundantly present brain and retina. It can be obtained directly from fish oil and maternal milk.

Prostaglandin D2

C20H32O5 (352.2249622)

Prostaglandin D2 (or PGD2) is a prostaglandin that is actively produced in various organs such as the brain, spleen, thymus, bone marrow, uterus, ovary, oviduct, testis, prostate and epididymis, and is involved in many physiological events. PGD2 binds to the prostaglandin D2 receptor (PTGDR) which is a G-protein-coupled receptor. Its activity is mainly mediated by G-S proteins that stimulate adenylate cyclase resulting in an elevation of intracellular cAMP and Ca2+. PGD2 promotes sleep; regulates body temperature, olfactory function, hormone release, and nociception in the central nervous system; prevents platelet aggregation; and induces vasodilation and bronchoconstriction. PGD2 is also released from mast cells as an allergic and inflammatory mediator. Prostaglandin H2 is an unstable intermediate formed from PGG2 by the action of cyclooxygenase (COX) in the arachidonate cascade. In mammalian systems, it is efficiently converted into more stable arachidonate metabolites, such as PGD2, PGE2, PGF2a by the action of three groups of enzymes, PGD synthases (PGDS), PGE synthases and PGF synthases, respectively. PGDS catalyzes the isomerization of PGH2 to PGD2. Two types of PGD2 synthase are known. Lipocalin-type PGD synthase is present in cerebrospinal fluid, seminal plasma and may play an important role in male reproduction. Another PGD synthase, hematopoietic PGD synthase is present in the spleen, fallopian tube, endometrial gland cells, extravillous trophoblasts and villous trophoblasts, and perhaps plays an important role in female reproduction. Recent studies demonstrate that PGD2 is probably involved in multiple aspects of inflammation through its dual receptor systems, DP and CRTH2. (PMID:12148545)Prostaglandins are 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 signalling pathways. Prostaglandin D2 (or PGD2) is a prostaglandin that is actively produced in various organs such as the brain, spleen, thymus, bone marrow, uterus, ovary, oviduct, testis, prostate and epididymis, and is involved in many physiological events. PGD2 binds to the prostaglandin D2 receptor (PTGDR) which is a G-protein-coupled receptor. Its activity is mainly mediated by G-S proteins that stimulate adenylate cyclase resulting in an elevation of intracellular cAMP and Ca2+. PGD2 promotes sleep; regulates body temperature, olfactory function, hormone release, and nociception in the central nervous system; prevents platelet aggregation; and induces vasodilation and bronchoconstriction. PGD2 is also released from mast cells as an allergic and inflammatory mediator. Chemical was purchased from CAY 12010, (Lot 0436713-1); Diagnostic ions: 351.1, 333.0, 271.3, 233.1, 189.1

Cholesterol

C27H46O (386.3548466)

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

Xanthyletin

C14H12O3 (228.0786402)

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.

Prostaglandin B2

C20H30O4 (334.214398)

Prostaglandin B2 (PGB2) is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207). Prostaglandins are 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 signalling pathways. Prostaglandin B2 (PGB2) is a prostanoid. Prostanoids is a term that collectively describes prostaglandins, prostacyclines and thromboxanes. Prostanoids are a subclass of the lipid mediator group known as eicosanoids. They derive from C-20 polyunsaturated fatty acids, mainly dihomo-gamma-linoleic (20:3n-6), arachidonic (20:4n-6), and eicosapentaenoic (20:5n-3) acids, through the action of cyclooxygenases-1 and -2 (COX-1 and COX-2). The reaction product of COX is the unstable endoperoxide prostaglandin H (PGH) that is further transformed into the individual prostanoids by a series of specific prostanoid synthases. Prostanoids are local-acting mediators formed and inactivated within the same or neighbouring cells prior to their release into circulation as inactive metabolites (15-keto- and 13,14-dihydroketo metabolites). Non-enzymatic peroxidation of arachidonic acid and other fatty acids in vivo can result in prostaglandin-like substances isomeric to the COX-derived prostaglandins that are termed isoprostanes. Prostanoids take part in many physiological and pathophysiological processes in practically every organ, tissue and cell, including the vascular, renal, gastrointestinal and reproductive systems. Their activities are mediated through prostanoid-specific receptors and intracellular signalling pathways, whilst their biosynthesis and action are blocked by nonsteroidal antiinflammatory drugs (NSAID). Isoprostanes are considered to be reliable markers of oxidant stress status and have been linked to inflammation, ischaemia-reperfusion, diabetes, cardiovascular disease, reproductive disorders and diabetes. (PMID: 16986207)

Batyl alcohol

C21H44O3 (344.3290274)

C26170 - Protective Agent > C797 - Radioprotective Agent 3-(Octadecyloxy)propane-1,2-diol is an endogenous metabolite.

Brassicasterol

C28H46O (398.3548466)

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

C27H44O (384.3391974)

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

C20H30O4 (334.214398)

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.

15-Keto-prostaglandin F2a

C20H32O5 (352.2249622)

15-Keto-prostaglandin F2a is the oxidized product of prostaglandin F2a by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-dydroxyl group. 15-Keto-prostaglandin F2a is further metabolized by its delta13-reduction, beta-oxidation and omega oxidation. The ultimate metabolite is 5a,7a-dihydroxy-11-keto-tetranorprosta-1,16-dioic acid, and excreted in urine. Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787, 184496, 5951401, 12432938)Prostaglandins are 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 signalling pathways. 15-Keto-prostaglandin F2a is the oxidized product of prostaglandin F2a by 15-hydroxyprostaglandin dehydrogenase, which is present in lung, kidney, placenta and other tissues and catalyzes the NAD- or NADP-dependent dehydrogenation of 15-dydroxyl group. 15-Keto-prostaglandin F2a is further metabolized by its delta13-reduction, beta-oxidation and omega oxidation. The ultimate metabolite is 5a,7a-dihydroxy-11-keto-tetranorprosta-1,16-dioic acid, and excreted in urine. Prostaglandin F2a (PGF2) is one of the earliest discovered and most common prostaglandins is actively biosynthesized in various organs of mammals and exhibits a variety of biological activities, including contraction of pulmonary arteries. PGF2 is mainly synthesized directly from PGH2 by PGH2 9,11-endoperoxide reductase. A small amount of PGF2 is also produced from PGE2 by PGE2 9-ketoreductase. A PGF2 epimer has been reported to exhibit various biological activities, and its levels are increased in bronchoalveolar lavage fluid, plasma, and urine in patients with mastocytosis and bronchial asthma. PGF2 is synthesized from PGD2 by PGD2 11-ketoreductase. (PMID: 16475787, 184496, 5951401, 12432938)

Fucosterol

C29H48O (412.37049579999996)

Characteristic sterol of seaweeds; isolated from bladderwrack Fucus vesiculosus. Fucosterol is found in lemon grass and coconut. Fucosterol is found in coconut. Characteristic sterol of seaweeds; isolated from bladderwrack Fucus vesiculosu Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1]. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].

Neocembrene

C20H32 (272.2503872)

(-)-alpha-Curcumene

C15H22 (202.1721412)

1-[(2R)-hex-5-en-2-yl]-4-methylbenzene is a member of the class of compounds known as aromatic monoterpenoids. Aromatic monoterpenoids are monoterpenoids containing at least one aromatic ring. (-)-alpha-Curcumene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Germacrene

C15H24 (204.18779039999998)

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 .

6-Hydroxyluteolin

C15H10O7 (302.042651)

Isolated from Valerianella eriocarpa (Italian corn salad). 6-Hydroxyluteolin is found in many foods, some of which are common thyme, mexican oregano, green vegetables, and lemon verbena. 6-Hydroxyluteolin is found in common thyme. 6-Hydroxyluteolin is isolated from Valerianella eriocarpa (Italian corn salad).

Clavulone I

C25H34O7 (446.2304414)

Cetyl palmitate

C32H64O2 (480.4906044)

Ceryl palmitate, also known as hexadecanyl hexadecanoate or hexadecanoic acid, hexadecyl ester, is a member of the class of compounds known as wax monoesters. Wax monoesters are waxes bearing an ester group at exactly one position. Thus, ceryl palmitate is considered to be a fatty ester lipid molecule. Ceryl palmitate is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Ceryl palmitate can be found in loquat and opium poppy, which makes ceryl palmitate a potential biomarker for the consumption of these food products.

Chimyl alcohol

C19H40O3 (316.297729)

24-Methylenecholesterol

C28H46O (398.3548466)

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

C28H50O (402.386145)

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)

Ergostane

C28H50 (386.39123)

germacrene C

C15H24 (204.18779039999998)

Elisabethatriene

C20H32 (272.2503872)

Cembrene C

C20H32 (272.2503872)

A fourteen-membered macrocyclic diterpene consisting of 12-isopropylidene-1,5,9-trimethylcyclotetradecane having three endocyclic double bonds located at positions 1, 5 and 9.

Clionasterol

C29H50O (414.386145)

Clionasterol is a triterpenoid isolated from the Indian marine red alga Gracilaria edulis, the sponge Veronica aerophoba and the Kenyan Marine Green. Macroalga Halimeda macroloba. It is a potent inhibitor of complement component C1. (PMID 12624828). D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites

5-Dehydroavenasterol

C29H46O (410.3548466)

5-Dehydroavenasterol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, 5-dehydroavenasterol is considered to be a sterol lipid molecule. 5-Dehydroavenasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Dehydroavenasterol is an intermediate in the biosynthesis of steroids. It is the third to last step in the synthesis of stigmasterol and is converted from delta 7-avenasterol via the enzyme lathosterol oxidase (EC 1.14.21.6). It is then converted into Isofucosterol via the enzyme 7-dehydrocholesterol reductase (EC 1.3.1.21). 5-Dehydroavenasterol is an intermediate in the biosynthesis of steroids (KEGG ID C15783). It is the third to last step in the synthesis of Stigmasterol and is converted from delta 7-Avenasterol via the enzyme lathosterol oxidase [EC:1.14.21.6]. It is then converted to Isofucosterol via the enzyme 7-dehydrocholesterol reductase [EC:1.3.1.21]. [HMDB]. 5-Dehydroavenasterol is found in many foods, some of which are daikon radish, nance, skunk currant, and jujube.

Poriferasterol

C29H48O (412.37049579999996)

(+)-germacrene D

C15H24 (204.18779039999998)

8(R)-HETE

C20H32O3 (320.23513219999995)

A HETE having an (8R)-hydroxy group and (5Z)-, (9E)-, (11Z)- and (14Z)-double bonds.

clavulone III

C25H34O7 (446.2304414)

clavulone IV

C25H34O7 (446.2304414)

Spathulenol

C15H24O (220.18270539999997)

Spathulenol is a tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. It has a role as a volatile oil component, a plant metabolite, an anaesthetic and a vasodilator agent. It is a sesquiterpenoid, a carbotricyclic compound, a tertiary alcohol and an olefinic compound. Spathulenol is a natural product found in Xylopia aromatica, Xylopia emarginata, and other organisms with data available. See also: Chamomile (part of). A tricyclic sesquiterpenoid that is 4-methylidenedecahydro-1H-cyclopropa[e]azulene carrying three methyl substituents at positions 1, 1 and 7 as well as a hydroxy substituent at position 7. Spathulenol is found in alcoholic beverages. Spathulenol is a constituent of Salvia sclarea (clary sage).

Xanthoxyletin

C15H14O4 (258.0892044)

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.

Levulinic acid

C5H8O3 (116.0473418)

Found in beet, caramel etcand is also reported in papaya (Carica papaya), wheat bread, rice bran, sake and Chinese quince fruit (Chaenomeles legenaria)and is also production by lychee (Litchi chinensis), Malabar spinach (Basella rubra) and Phyllophora subspecies Flavour ingredient. Levulinic acid is a crystalline keto acid prepared from levulose, inulin, starch, etc., by boiling them with dilute hydrochloric or sulfuric acids. D004791 - Enzyme Inhibitors Levulinic acid is a precursor for the synthesis of biofuels, such as ethyl levulinate. Levulinic acid is a precursor for the synthesis of biofuels, such as ethyl levulinate.

Methyl Arachidonate

C21H34O2 (318.2558664)

Methyl Arachidonate, also known as Arachidonate methyl ester or (5Z,8Z,11Z,14Z)-Icosatetraenoate methyl ester, is classified as a member of the Fatty acid methyl esters. Fatty acid methyl esters are compounds containing a fatty acid that is esterified with a methyl group. They have the general structure RC(=O)OR, where R=fatty aliphatic tail or organyl group and R=methyl group. Methyl Arachidonate is considered to be practically insoluble (in water) and basic. Methyl Arachidonate can be synthesized from arachidonic acid. Methyl Arachidonate can be synthesized into 12(R)-HPETE methyl ester and 12(S)-HPETE methyl ester

Ergosterol peroxide

C28H44O3 (428.3290274)

Ergosterol peroxide is found in fruits. Ergosterol peroxide is obtained from leaves of Ananas comosus (pineapple obtained from leaves of Ananas comosus (pineapple). Ergosterol peroxide is found in pineapple and fruits.

(E)-Calamene

C15H22 (202.1721412)

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-Curcumene

C15H22 (202.1721412)

alpha-Curcumene belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units

(+)-alpha-Muurolene

C15H24 (204.18779039999998)

(+)-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)

29-Methylisofucosterol

C30H50O (426.386145)

29-Methylisofucosterol is found in mollusks. 29-Methylisofucosterol is a constituent of the edible scallop Trochostoma orientale. Constituent of the edible scallop Trochostoma orientale. 29-Methylisofucosterol is found in mollusks.

Cholesteryl acetate

C29H48O2 (428.36541079999995)

Cholesteryl acetate is a normal human cholesteryl ester present in diverse fluids and organs. Cholesteryl acetate is also present in foods. Food oxidation affects the quality and safety of the human diet by generating compounds with biological activities that can adversely affect health. In particular the susceptibility of cholesterol to oxidation is well known; certain products of cholesterol oxidation have been reported to produce cytotoxic, angiotoxic and carcinogenic effects. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 10918380, 16458590, 9420339, 3343104, 6721900, 7278520).

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

C15H22 (202.1721412)

Calamenene belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Docosahexaenoicacid(DHA)

C22H32O2 (328.24021719999996)

2,5,9-Trimethyl-11-oxotricyclo[6.3.0.01,5]undec-3-ene-3-carboxylic acid

C15H20O3 (248.14123700000002)

Icosa-2,4,6,8,10-pentaenoic acid

C20H30O2 (302.224568)

1-[(2R,3S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

C9H12N2O6 (244.0695332)

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-beta-d-Arabinofuranosylguanine

C10H13N5O5 (283.09166480000005)

5-Hydroperoxyeicosatetraenoic acid

C20H32O4 (336.2300472)

5,8,11,14-Icosatetraenoic Acid

C20H32O2 (304.24021719999996)

9-Arabinofuranosyladenine

C10H13N5O4 (267.09674980000005)

Eicosatetraenoic acid

C20H32O2 (304.24021719999996)

Isofuranodiene

C15H20O (216.151407)

L-Thymidine

C10H14N2O5 (242.09026740000002)

Isolated from seedlings of Phaseolus vulgaris (kidney bean)

lavendustin c

C14H13NO5 (275.0793688)

D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor

Peridinin

C39H50O7 (630.3556349999999)

5-Hydroxytryptoline

C11H12N2O (188.09495819999998)

Poriferasterol

C29H48O (412.37049579999996)

Loliolide

C11H16O3 (196.1099386)

Loliolide, also known as (3s5r)-loliolide, is a member of the class of compounds known as benzofurans. Benzofurans are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Loliolide is soluble (in water) and an extremely weak acidic compound (based on its pKa). Loliolide can be found in sunflower, tea, and wakame, which makes loliolide a potential biomarker for the consumption of these food products.

gamma-Elemene

C15H24 (204.18779039999998)

Gamma-Elemene, also known as g-elemene, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-erythritol-phosphate (MEP) pathway in the cytosol. Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. More formally, gamma-elemene is a cyclohexane substituted at positions 1, 1, 2, and 4 by methyl, vinyl, isopropenyl and isopropylidene groups, respectively. There are four known elemene isomers including α-, β-, γ-, and δ-elemene. The elemenes contribute to the floral aromas of some plants and are used as pheromones by some insects. Gamma-elemene is found in many essential plant oils including wormwood leaf oil, peppermint oil, pepper tree leaf oil, parsley leaf oil, orange peel oil, lime oil, juniper berry oil, hinoki leaf oil, angelica root oil, and angelica seed oil. Gamma-elemene has been shown to exhibit good insecticidal activity against the crop pest Spodoptera litura (tobacco cutworm or cotton leafworm) and could be useful as an eco-friendly biopesticide (PMID:28634795). Gamma-elemene, also known as (+)-G-elemene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Gamma-elemene can be found in a number of food items such as sweet basil, mandarin orange (clementine, tangerine), sweet bay, and pot marjoram, which makes gamma-elemene a potential biomarker for the consumption of these food products.

Germacrene A

C15H24 (204.18779039999998)

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.

1-S-cis-Calamenene

C15H22 (202.1721412)

(E)-Calamene, also known as calamenene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (E)-Calamene is possibly neutral. (E)-Calamene is found in highest concentrations in allspices, common oregano, and rosemaries and in lower concentrations in lovages. (E)-Calamene has also been detected in cloves, guava, summer savories, sweet basils, and pepper (spice). This could make (E)-calamene a potential biomarker for the consumption of these foods. Calamene is a metabolite of plant Turnera diffusa (Damiana, Mexican holly, Old Womans Broom), 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. 1-s-cis-calamenene, also known as (7r,10r)-calamenene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. 1-s-cis-calamenene is a herb and spice tasting compound found in rosemary, which makes 1-s-cis-calamenene a potential biomarker for the consumption of this food product.

Androsterol

C19H30O (274.229653)

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.

1-methyl-5-methylene-8-(1-methylethyl)-1,6-cyclodecadiene

C15H24 (204.18779039999998)

Flavouring compound [Flavornet]

Caffeine

C8H10N4O2 (194.080372)

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

Incensole

C20H34O2 (306.2558664)

Incensole is a sesquiterpenoid. CID 73228441 is a natural product found in Boswellia serrata with data available. Incensole, a 14-membered diterpenoid, is isolated from both essential oils and resins of frankincense. Incensole has shown anti-inflammatory and anti-depression activities due to their ability to activate ion channels in the brain to alleviate anxiety or depression[1]. Incensole, a 14-membered diterpenoid, is isolated from both essential oils and resins of frankincense. Incensole has shown anti-inflammatory and anti-depression activities due to their ability to activate ion channels in the brain to alleviate anxiety or depression[1].

Aristolone

C15H22O (218.1670562)

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].

Capillolide

C20H32O5 (352.2249622)

A natural product found in Sinularia capillosa and Sinularia microclavata.

Crassumolide B

C20H28O3 (316.2038338)

Cerevisterol

C28H46O3 (430.34467659999996)

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].

Flexusine B

C20H30O2 (302.224568)

Chlorovulone II

C21H29ClO4 (380.17542640000005)

Crassumolide A

C20H28O3 (316.2038338)

A cembrane diterpenoid isolated from the soft coral Lobophytum crassum and shown to have anti-inflammatory and antineoplastic activity.

Grandilobatin D

C20H32O2 (304.24021719999996)

Sinularolide D

C20H28O4 (332.19874880000003)

A cembrane diterpenoid isolated from Sinularia gibberosa and has been shown to exhibit antineoplastic activity.

Gibberosene A

C22H32O4 (360.2300472)

Grandilobatin E

C20H32O2 (304.24021719999996)

Crassumolide D

C20H28O3 (316.2038338)

Dendronpholide H

C24H38O7 (438.2617398)

1,4-dimethyl-2,3,3a,4,5,6-hexahydroazulene

C12H18 (162.1408428)

Microclavatin

C20H28O3 (316.2038338)

A macrocyclic diterpenoid isolated from the soft coral Sinularia microclavata and has been shown to exhibit cytotoxic activities against tumor cell lines.

Querciformolide A

C22H32O7 (408.2147922)

Nardosinanol C

C15H22O3 (250.1568862)

Cespihypotin V

C20H28O4 (332.19874880000003)

Crassumolide C

C21H28O4 (344.19874880000003)

Gibberosene C

C20H32O3 (320.23513219999995)

Dendronpholide G

C23H36O7 (424.2460906)

Sarcostolide G

C20H28O4 (332.19874880000003)

Crassumolide E

C20H32O4 (336.2300472)

Cespihypotin T

C19H28O4 (320.19874880000003)

Grandilobatin A

C21H36O4 (352.2613456)

Clavulolactone I

C22H28O5 (372.1936638)

5-methyl-2-(6-methylhept-5-en-2-yl)phenol

C15H22O (218.1670562)

Granosolide B

C24H34O7 (434.2304414)

Sinularolide C

C20H28O5 (348.1936638)

A cembrane diterpenoid that is an epimer of sinularolide B at C-3. Isolated from Sinularia gibberosa and has been found to exhibit antineoplastic activity.

Brianodin B

C28H38O14 (598.2261447999999)

Nardosinanol A

C15H22O (218.1670562)

Grandilobatin C

C20H32O3 (320.23513219999995)

Dendronpholide F

C22H34O7 (410.2304414)

Granosolide A

C22H32O6 (392.2198772)

Flexusine A

C20H30O2 (302.224568)

Grandilobatin B

C20H32O3 (320.23513219999995)

Bipinnatin J

C20H24O4 (328.1674504)

Suberosanone

C15H24O (220.18270539999997)

Bipinnatin K

C23H26O9 (446.15767460000006)

Bipinnatin P

C25H28O11 (504.16315380000003)

Bipinnatin Q

C23H26O11 (478.14750460000005)

Nardosinanol B

C15H20O2 (232.14632200000003)

Palmitic Acid

C16H32O2 (256.2402172)

COVID info from WikiPathways D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Curcumene

C15H22 (202.1721412)

sitosterol

C29H50O (414.386145)

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].

Methyl arachidonate

C21H34O2 (318.2558664)

A fatty acid methyl ester resulting from the formal condensation of the carboxy group of arachidonic acid with methanol.

Stigmasterol

C29H48O (412.37049579999996)

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.

Luteolin

C15H10O6 (286.047736)

Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.976 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.975 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.968 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.971 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].

Psychosine

C24H47NO7 (461.3352352)

A glycosylsphingoid consisting of sphingosine having a beta-D-galactosyl residue attached at the 1-position.

Peridinin

C39H50O7 (630.3556349999999)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Window width to select the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 10 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.

Fucosterol

C29H48O (412.37049579999996)

A 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol can be found in horseradish tree and sunflower, which makes (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol a potential biomarker for the consumption of these food products. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1]. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].

Globulol

C15H26O (222.1983546)

D006133 - Growth Substances > D006131 - Growth Inhibitors

Arachidonic acid

C20H32O2 (304.2402172)

A long-chain fatty acid that is a C20, polyunsaturated fatty acid having four (Z)-double bonds at positions 5, 8, 11 and 14. COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Arachidonic acid is an essential fatty acid and a major constituent of biomembranes. Arachidonic acid is an essential fatty acid and a major constituent of biomembranes.

michaolide F

C22H30O6 (390.204228)

A cembrane diterpenoid with cytotoxic activity isolated from the soft coral Lobophytum michaelae.

Alcyopterosins O

C15H22O2 (234.1619712)

Buddledin C

C15H22O (218.1670562)

pregna-1,4,20-trien-3-one

C21H28O (296.2140038)

A natural product found in Carijoa multiflora and Carijoa species.

Ergosterol peroxide

C28H44O3 (428.3290274)

Dinosterol

C30H52O (428.4017942)

punaglandin 1

C27H37ClO10 (556.2075132)

flavalin B

C15H22O3 (250.1568862)

A sesquiterpenoid of the class of nardosinane-type terpenoids isolated from the Formosan soft coral Lemnalia flava, and has been shown to exhibit neuroprotective activity.

hirsutalin H

C26H42O7 (466.2930382)

michaolide C

C24H32O8 (448.20970719999997)

A cembrane diterpenoid with cytotoxic activity isolated from the soft coral Lobophytum michaelae.

hirsutalin B

C30H46O9 (550.3141666)

hirsutalin A

C28H44O7 (492.3086874)

A natural product found in Cladiella hirsuta.

Punaglandin 2

C27H39ClO10 (558.2231624)

lemnafricanol

C17H26O5 (310.1780146)

Heptadecyl heptadecanoate

C34H68O2 (508.52190279999996)

hirsutalin E

C24H40O5 (408.28755900000004)

A natural product found in Cladiella hirsuta.

Spathulenol

C15H24O (220.18270539999997)

Constituent of Salvia sclarea (clary sage). Spathulenol is found in many foods, some of which are tarragon, spearmint, common sage, and tea.

Cetyl stearate

C34H68O2 (508.52190279999996)

punaglandin 3

C25H33ClO8 (496.18638480000004)

Ledol

C15H26O (222.1983546)

Ledol is a sesquiterpenoid. Ledol is a natural product found in Waitzia acuminata, Aloysia gratissima, and other organisms with data available. Constituent of Valeriana officinalis (valerian), Piper subspecies and others. Ledol is found in many foods, some of which are fats and oils, common sage, tea, and allspice. Ledol ((+)-Ledol) is an antifungal agent that can be isolated from the essential oil fractions of Rhododendron tomentosum. Ledol is also the expectorant and antitussive agent, which is simultaneously responsible for adverse reactions such as dizziness, nausea and vomiting[1]. Ledol ((+)-Ledol) is an antifungal agent that can be isolated from the essential oil fractions of Rhododendron tomentosum. Ledol is also the expectorant and antitussive agent, which is simultaneously responsible for adverse reactions such as dizziness, nausea and vomiting[1].

punaglandin 4

C25H35ClO8 (498.202034)

pachycladin A

C26H44O7 (468.3086874)

hirsutalin D

C26H40O7 (464.277389)

michaolide H

C27H38O10 (522.2464848)

A cembrane diterpenoid with cytotoxic activity isolated from the soft coral Lobophytum michaelae.

5-Dehydroavenasterol

C29H46O (410.3548466)

5-Dehydroavenasterol belongs to the class of organic compounds known as stigmastanes and derivatives. These are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, 5-dehydroavenasterol is considered to be a sterol lipid molecule. 5-Dehydroavenasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 5-Dehydroavenasterol is an intermediate in the biosynthesis of steroids. It is the third to last step in the synthesis of stigmasterol and is converted from delta 7-avenasterol via the enzyme lathosterol oxidase (EC 1.14.21.6). It is then converted into Isofucosterol via the enzyme 7-dehydrocholesterol reductase (EC 1.3.1.21). 5-Dehydroavenasterol is an intermediate in the biosynthesis of steroids (KEGG ID C15783). It is the third to last step in the synthesis of Stigmasterol and is converted from delta 7-Avenasterol via the enzyme lathosterol oxidase [EC:1.14.21.6]. It is then converted to Isofucosterol via the enzyme 7-dehydrocholesterol reductase [EC:1.3.1.21]. [HMDB]. 5-Dehydroavenasterol is found in many foods, some of which are daikon radish, nance, skunk currant, and jujube.

Waixenicin A

C26H36O7 (460.2460906)

seco-pseudopteroxazole

C21H29NO (311.2249024)

A natural product found in Pseudopterogorgia elisabethae.

michaolide A

C24H32O8 (448.20970719999997)

A cembrane diterpenoid with cytotoxic activity isolated from the soft coral Lobophytum michaelae.

sinulobatin B

C20H28O (284.2140038)

lobophytumin D

C20H32 (272.2503872)

A diterpenoid that is 1,2,3,4,4a,5,6,8a-octahydronaphthalene substituted by methyl groups at positions 4a and 8 and a 6-methylhepta-1,5-dien-2-yl group at position 2 (the 2S,4aR,8aR-stereoisomer). It has been isolated from from the Hainan soft coral Lobophytum cristatum.

lobophytumin C

C20H32 (272.2503872)

A diterpenoid that is decahydronaphthalene substituted by a methyl group at position 4a, a methylidiene group at position 1 and a 6-methylhepta-1,5-dien-2-yl group at position 7 (the 4aS,7S,8aR-stereoisomer). It has been isolated from the Hainan soft coral Lobophytum cristatum.

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

C27H46O (386.3548466)

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

klymollin D

C24H36O7 (436.2460906)

An eunicellin diterpenoid isolated from the soft coral Klyxum molle.

6-bromo-N-methyltryptamine

C11H13BrN2 (252.02620380000002)

A natural product found in Paramuricea clavata.

eunicidiol

C20H32O2 (304.24021719999996)

clavirin I

C17H22O4 (290.1518012)

Arachidyl stearate

C38H76O2 (564.5844996)

sinulobatin A

C22H30O3 (342.21948299999997)

capillofuranocarboxylate

C18H24O5 (320.1623654)

michaolide D

C24H30O8 (446.194058)

A cembrane diterpenoid with cytotoxic activity isolated from the soft coral Lobophytum michaelae.

hirsutalin C

C28H44O7 (492.3086874)

michaolide E

C24H32O7 (432.2147922)

A cembrane diterpenoid with cytotoxic activity isolated from the soft coral Lobophytum michaelae.

michaolide B

C24H32O8 (448.20970719999997)

A cembrane diterpenoid with cytotoxic activity isolated from the soft coral Lobophytum michaelae.

flavalin A

C15H22O2 (234.1619712)

A sesquiterpenoid of the class of nardosinane-type terpenoids isolated from the Formosan soft coral Lemnalia flava, and has been shown to exhibit neuroprotective activity.

1,3,7-trimethylisoguanine

C8H11N5O (193.09635559999998)

A natural product found in Paramuricea clavata and Pseudodistoma cereum.

HEPTADECYL NONADECANOATE

C36H72O2 (536.5532012)

hirsutalin F

C28H44O8 (508.3036024)

A natural product found in Cladiella hirsuta.

pseudopteroxazole

C21H27NO (309.20925320000003)

A natural product found in Pseudopterogorgia elisabethae.

flavalin C

C16H24O3 (264.1725354)

A sesquiterpenoid of the class of nardosinane-type terpenoids isolated from the Formosan soft coral Lemnalia flava.

michaolide K

C24H34O8 (450.2253564)

A cembrane diterpenoid with cytotoxic activity isolated from the soft coral Lobophytum michaelae.

lipidyl pseudopterane D

C37H54O7 (610.3869334)

pachycladin B

C26H42O7 (466.2930382)

Myristyl stearate

C32H64O2 (480.4906044)

lavendustin c

C14H13NO5 (275.0793688)

D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor

Batyl alcohol

C21H44O3 (344.3290274)

Caffeine

C8H10N4O2 (194.080372)

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

C29H52O (416.4017942)

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

C28H46O (398.3548466)

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

C28H48O (400.37049579999996)

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.

Thymidine

C10H14N2O5 (242.09026740000002)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.220 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.211 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.213 Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3]. Thymidine, a specific precursor of deoxyribonucleic acid, is used as a cell synchronizing agent. Thymidine is a DNA synthesis inhibitor that can arrest cell at G1/S boundary, prior to DNA replication[1][2][3].

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

Pregnenolone

C21H32O2 (316.24021719999996)

A 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20. C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Pregnenolone is a derivative of cholesterol, the product of Cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1); this reaction consists of three consecutive monooxygenations; a 22-hydroxylation, 20-hydroxylation and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted to pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and transport to the inner membrane steps and thus to exerts a powerful control over the use of cholesterol for aldosterone production. (PMID: 17222962, 15823613, 16632873, 15134809) [HMDB]. Pregnenolone is found in many foods, some of which are common wheat, yellow bell pepper, oval-leaf huckleberry, and fenugreek. Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3]. Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

Tryptamine

C10H12N2 (160.1000432)

Eicosapentaenoic acid

C20H30O2 (302.224568)

Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3]. Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3].

Prostaglandin B2

C20H30O4 (334.214398)

Bufotenine

C12H16N2O (204.12625659999998)

loliolide

C11H16O3 (196.1099386)

A natural product found in Brachystemma calycinum.

Sphingosine

C18H37NO2 (299.2824142)

A sphing-4-enine in which the double bond is trans. D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator[1][2][3][4]. D-erythro-Sphingosine (Erythrosphingosine) is a very potent activator of p32-kinase with an EC50 of 8 μM, and inhibits protein kinase C (PKC). D-erythro-Sphingosine (Erythrosphingosine) is also a PP2A activator[1][2][3][4].

LEVULINIC ACID

C5H8O3 (116.0473418)

D004791 - Enzyme Inhibitors Levulinic acid is a precursor for the synthesis of biofuels, such as ethyl levulinate. Levulinic acid is a precursor for the synthesis of biofuels, such as ethyl levulinate.

Cholestenone

C27H44O (384.3391974)

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].

Xanthyletin

C14H12O3 (228.0786402)

Hexadecanoic acid

C16H32O2 (256.2402172)

Desmosterol

C27H44O (384.3391974)

DOCOSAHEXAENOIC ACID

C22H32O2 (328.24021719999996)

7α-hydroxycholesterol

C27H46O2 (402.3497616)

The 7alpha-hydroxy derivative of cholesterol. 7α-Hydroxycholesterol is a cholesterol oxide and is formed by both enzymatic and non-enzymatic oxidation. 7α-Hydroxycholesterol can be used as a biomarker for lipid peroxidation[1][2].

SARCOPHYTOL A

C20H32O (288.24530219999997)

D000970 - Antineoplastic Agents

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].

clavulone II

C25H34O7 (446.2304414)

20-acetoxy-clavulone I

C27H36O9 (504.2359206)

20-acetoxy-clavulone III

C27H36O9 (504.2359206)

chlorovulone I

C21H29ClO4 (380.17542640000005)

chlorovulone IV

C21H29ClO4 (380.17542640000005)

10,11-epoxy-chlorovulone I

C21H29ClO5 (396.17034140000004)

Bromovulone I

C21H29BrO4 (424.12490940000004)

Iodovulone I

C21H29IO4 (472.1110504)

clavulolactone II

C22H28O5 (372.1936638)

clavulolactone III

C22H28O5 (372.1936638)

17,18-dehydro-clavulone I

C25H32O7 (444.2147922)

preclavulone lactone I

C20H28O3 (316.2038338)

preclavulone lactone II

C20H28O3 (316.2038338)

4-epi-clavulone II

C25H34O7 (446.2304414)

4-epi-clavulone III

C25H34O7 (446.2304414)

clavirin II

C17H22O4 (290.1518012)

punaglandin 5

C25H35ClO8 (498.202034)

punaglandin 6

C25H37ClO8 (500.2176832)

punaglandin 7

C23H31ClO6 (438.1809056)

punaglandin 8

C23H33ClO6 (440.19655480000006)

7,11-hexadecadien-1-ol

C16H30O (238.22965299999998)

astrogorgiadiol B

C27H44O2 (400.3341124)

Xeniolit A

C20H28O4 (332.19874880000003)

Erogorgiaene

C20H30 (270.234738)

DOCOSA-2,4,6,8,10,12-HEXAENOIC ACID

C22H32O2 (328.24021719999996)

Cetyl palmitate

C32H64O2 (480.4906044)

29-methylisofucosterol

C30H50O (426.386145)

Beta-Elemene

C15H24 (204.18779039999998)

β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis. β-Elemene ((-)-β-Elemene; Levo-β-elemene) is isolated from natural plant Curcuma aromatica with an antitumor activity. β-Elemene can induce cell apoptosis.

Isointermedeol

C15H26O (222.1983546)

(+)-alpha-Muurolene

C15H24 (204.18779039999998)

myristyl oleate

C32H62O2 (478.47495519999995)

Prostaglandin D2

C20H32O5 (352.2249622)

A member of the class of prostaglandins D that is prosta-5,13-dien-1-oic acid substituted by hydroxy groups at positions 9 and 15 and an oxo group at position 11 (the 5Z,9alpha,13E,15S- stereoisomer).

PROSTAGLANDIN A2

C20H30O4 (334.214398)

chlorovulone I

C21H29O4Cl (380.17542640000005)

Chlorovulone II

C21H29O4Cl (380.17542640000005)

chlorovulone III

C21H29O4Cl (380.17542640000005)

10,11-epoxy-chlorovulone I

C21H29O5Cl (396.17034140000004)

Bromovulone I

C21H29O4Br (424.12490940000004)

punaglandin 1

C27H37O10Cl (556.2075132)

Punaglandin 2

C27H39O10Cl (558.2231624)

punaglandin 4

C25H35O8Cl (498.202034)

punaglandin 5

C25H35O8Cl (498.202034)

punaglandin 6

C25H37O8Cl (500.2176832)

WE 20:6;O3

C20H28O5 (348.1936638)

clionasterol

C29H50O (414.386145)

A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites

alpha-Curcumene

C15H22 (202.1721412)

Alpha-curcumene is also known as α-curcumene. Alpha-curcumene is a herb tasting compound and can be found in a number of food items such as pepper (spice), lovage, wild carrot, and rosemary, which makes alpha-curcumene a potential biomarker for the consumption of these food products.

Lobohedleolide

C20H26O4 (330.18309960000005)

A cembrane diterpenoid isolated from Lobophytum hedleyi and Lobophytum. It exhibits anti-HIV-1 activity.

Furanodiene

C15H20O (216.151407)

Lanol

C27H46O (386.3548466)

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

Pirod

C4H4N2O2 (112.02727639999999)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.

Cholesteryl acetate

C29H48O2 (428.36541079999995)

A cholesterol ester obtained by formal acylation of the hydroxy group of cholesterol by acetic acid. Cholesteryl acetate is a normal human cholesteryl ester present in diverse fluids and organs. Cholesteryl acetate is also present in foods. Food oxidation affects the quality and safety of the human diet by generating compounds with biological activities that can adversely affect health. In particular the susceptibility of cholesterol to oxidation is well known; certain products of cholesterol oxidation have been reported to produce cytotoxic, angiotoxic and carcinogenic effects. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 10918380, 16458590, 9420339, 3343104, 6721900, 7278520) [HMDB]

Minabeolide 1

C28H38O3 (422.2820798)

A withanolide that is (22R)-22,26-epoxyergosta-1,4,24-triene substituted by oxo groups at positions 3 and 26. Isolated from Paraminabea acronocephala, it exhibits antineoplastic and anti-inflammatory activities.

Eunicea sesquiterpenoid 3

C15H22O3 (250.1568862)

A natural product found in Eunicea.

(-)-Germacrene A

C15H24 (204.18779039999998)

Minabeolide 4

C27H38O3 (410.2820798)

A withanolide that is (22R,25S)-22,26-epoxycholesta-1,4-dien-26-one substituted by an oxo group at position 3. Isolated from Paraminabea acronocephala,it exhibits anti-inflammatory activity.

(-)-Alismoxide

C15H26O2 (238.1932696)

A natural product found in Sanicula lamelligera.

Verrucoside

C30H48O7 (520.3399858)

A natural product found in Eunicella verrucosa.

Eunicea sesquiterpenoid 2

C15H22O3 (250.1568862)

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

Pacificin C(rel)

C20H34O4 (338.24569640000004)

A natural product found in Nephthea pacifica.

Pacificin H(rel)

C22H36O5 (380.2562606)

A natural product found in Nephthea pacifica.

Tritoniopsin B, rel-

C24H38O7 (438.2617398)

A natural product found in Tritoniopsis elegans and Cladiella krempfi.

Eunicea sesquiterpenoid 5

C20H30O5 (350.209313)

A natural product found in Eunicea.

Eunicea sesquiterpenoid 6

C20H30O5 (350.209313)

A natural product found in Eunicea.

(1S,2E,10R)-3,7,11,11-tetramethylbicyclo[8.1.0]undeca-2,6-diene

C15H24 (204.18779039999998)

Elongatol E

C15H24O3 (252.1725354)

A sesquiterpenoid that is 1,2,3a,4,5,5a,8,9,9a,9b-decahydronaphtho[2,1-b]furan substituted by methyl groups at positions 1, 9 and 9a and hydroxy groups at positions 2 and 5a. Isolated from methylene chloride solubles of the Formosan soft coral Nephthea elongata, it exhibits cytotoxicity against selected cancer cells.

17-Dimethylaminolobohedleolide

C22H33NO4 (375.2409458000001)

A cembrane diterpenoid isolated from Lobophytum and shown to have anti-HIV-1 activity.

Klymollin H

C27H40O11 (540.257049)

An eunicellin diterpenoid isolated from the soft coral Klyxum molle.

Minabeolide 5

C29H40O5 (468.28755900000004)

A withanolide that is (22R,25S)-22,26-epoxycholesta-1,4-dien-26-one substituted by an oxo group at position 3 and an acetoxy group at position 18. Isolated from Paraminabea acronocephala, it exhibits anti-inflammatory activity.

Klymollin C

C26H38O9 (494.25156979999997)

An eunicellin diterpenoid isolated from the soft coral Klyxum molle.

Klymollin G

C42H70O11 (750.491787)

An eunicellin diterpenoid isolated from the soft coral Klyxum molle.

Klymollin F

C40H66O11 (722.4604886000001)

An eunicellin diterpenoid isolated from the soft coral Klyxum molle.

Klymollin E

C28H42O11 (554.2726982)

An eunicellin diterpenoid isolated from the soft coral Klyxum molle.

Flavalin D

C16H24O3 (264.1725354)

A sesquiterpenoid of the class of nardosinane-type terpenoids isolated from the Formosan soft coral Lemnalia flava.

Minabeolide 2

C30H40O5 (480.28755900000004)

A withanolide that is (22R)-22,26-epoxyergosta-1,4,24-triene substituted by oxo groups at positions 3 and 26 and an acetoxy group at position 18. Isolated from Paraminabea acronocephala, it exhibits anti-inflammatory activity.

Tritoniopsin C, rel-

C24H38O6 (422.2668248)

A natural product found in Tritoniopsis elegans and Cladiella krempfi.

Elongatol A

C15H24O3 (252.1725354)

A sesquiterpenoid that is 1,2,3a,4,5,7,8,9,9a,9b-decahydronaphtho[2,1-b]furan substituted by methyl groups at positions 1, 9 and 9a and hydroxy groups at positions 2 and 7. Isolated from methylene chloride solubles of the Formosan soft coral Nephthea elongata, it exhibits cytotoxicity against selected cancer cells.

Minabeolide 8

C29H42O5 (470.30320820000003)

A withanolide that is (22R,25S)-22,26-epoxycholest-4-en-26-one substituted by an oxo group at position 3 and an alpha-acetoxy group at position 11. Isolated from Paraminabea acronocephala, it exhibits anti-inflammatory activity.

sinularolide B

C20H28O5 (348.1936638)

A cembrane diterpenoid isolated from Sinularia gibberosa and has been found to exhibit antineoplastic activity.

Hirsutalin G, (rel)-

C22H34O5 (378.24061140000003)

A natural product found in Cladiella hirsuta.

(1R,3R,4S,11S,12R)-3,4,11-trihydroxy-4,8,12-trimethyl-15-methylidene-13-oxabicyclo[10.3.2]heptadec-7-en-14-one

C20H32O5 (352.2249622)

Dinoprostone

C20H32O5 (352.2249622)

G - Genito urinary system and sex hormones > G02 - Other gynecologicals > G02A - Uterotonics > G02AD - Prostaglandins D012102 - Reproductive Control Agents > D010120 - Oxytocics C78568 - Prostaglandin Analogue Prostaglandin E2 (PGE2) is a hormone-like substance that participate in a wide range of body functions such as the contraction and relaxation of smooth muscle, the dilation and constriction of blood vessels, control of blood pressure, and modulation of inflammation.

(R)-nephthenol

C20H34O (290.2609514)

A cembrane diterpenoid obtained by regio- and stereoselective hydration of the exocyclic double bond of cembrene C.

4-Oxopentanoic acid

C5H8O3 (116.0473418)

An oxopentanoic acid with the oxo group in the 4-position.

Coprostanol

C27H48O (388.37049579999996)

A member of the class of phytosterols that is 5beta-cholestane carrying a hydroxy substituent at the 3beta-position.

Dihydrocholesterol

C27H48O (388.37049579999996)

5α-Cholestan-3β-ol is a derivitized steroid compound. 5α-Cholestan-3β-ol is a derivitized steroid compound.

11R-HETE

C20H32O3 (320.23513219999995)

An 11-HETE in which the chiral centre at position 11 has R-configuration.

Eunicea sesquiterpenoid 7

C20H28O5 (348.1936638)

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

5-Dehydroavenasterol

C29H46O (410.3548466)

Avenasterol

C29H48O (412.37049579999996)

A stigmastane sterol that is 5alpha-stigmastane carrying a hydroxy group at position 3beta and double bonds at positions 7 and 24.

icosa-5,8,11,14-tetraenoic acid

C20H32O2 (304.24021719999996)

Any icosatetraenoic acid with the double bonds at positions 5, 8, 11 and 14.

Hirsutalin C, (rel)-

C28H44O7 (492.3086874)

A natural product found in Cladiella hirsuta.

Hirsutalin D, (rel)-

C26H40O7 (464.277389)

A natural product found in Cladiella hirsuta.

Hirsutalin H, (rel)-

C26H42O7 (466.2930382)

A natural product found in Cladiella hirsuta.

Prostaglandin E2

C20H32O5 (352.2249622)

Prostaglandin F2alpha in which the hydroxy group at position 9 has been oxidised to the corresponding ketone. Prostaglandin E2 is the most common and most biologically potent of mammalian prostaglandins.

(1s,3r,5r,6r,9r)-6-hydroxy-6,10,10-trimethyltricyclo[7.2.0.0³,⁵]undecan-2-one

C14H22O2 (222.1619712)

(1r,4e,12r,14r)-1,5,9-trimethyl-12-(prop-1-en-2-yl)-15-oxabicyclo[12.1.0]pentadeca-4,8-dien-3-one

C20H30O2 (302.224568)

(1r,7s,9r,10s,12s,14r)-4,9,14-trimethyl-6,11,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0³,⁷.0¹⁰,¹²]pentadec-3-en-5-one

C15H18O4 (262.1205028)

(1r,3as,3bs,5s,5ar,7s,9s,9as,9bs,10s,11s,11ar)-5,5a,7,9,10-pentahydroxy-9a,11a-dimethyl-1-[(1r)-1-[(1r,2s)-2-methyl-2-[(2s)-3-methylbutan-2-yl]cyclopropyl]ethyl]-tetradecahydrocyclopenta[a]phenanthren-11-yl acetate

C32H54O7 (550.3869334)

eleutherobin

C35H48N2O10 (656.3308787999999)

(2r,3s,6s)-3-methyl-2-(3-oxobutyl)-6-(prop-1-en-2-yl)cycloheptan-1-one

C15H24O2 (236.1776204)

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

C20H34O (290.2609514)

(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

C27H46O4 (434.3395916)

(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

C27H40O4 (428.29264400000005)

methyl (1r,2r,3s,6s,7s)-3-[(2e,5s)-1-(acetyloxy)-5,6-dihydroxy-6-methylhept-2-en-2-yl]-1,7-dihydroxy-6-methylbicyclo[4.3.1]decane-2-carboxylate

C23H38O8 (442.2566548)

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

C20H40O2 (312.302814)

1-[(1as,4s,4as,5s,6s,8s,8as)-6-acetyl-8-hydroxy-4,4a-dimethyl-octahydronaphtho[4,4a-b]oxiren-5-yl]ethanone

C16H24O4 (280.1674504)

9-(acetyloxy)-12,13-dihydroxy-6-isopropyl-3,9,13-trimethyl-15-oxatricyclo[6.6.1.0²,⁷]pentadecan-3-yl butanoate

C26H44O7 (468.3086874)

(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

C24H36O6 (420.2511756)

1-(4-ethyl-5,6-dimethylheptan-2-yl)-6,9a,11a-trimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol

C31H56O (444.4330926)

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

C17H24O2 (260.17762039999997)

(1r,7r,9r,10s,12s,14r)-7-methoxy-4,9,14-trimethyl-6,11,15-trioxapentacyclo[8.5.0.0¹,¹⁴.0³,⁷.0¹⁰,¹²]pentadec-3-en-5-one

C16H20O5 (292.13106700000003)

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]acetaldehyde

C26H40O4 (416.29264400000005)

(2s)-2-[(8r,8as)-8,8a-dimethyl-4,6,7,8-tetrahydro-3h-naphthalen-2-yl]propane-1,2-diol

C15H24O2 (236.1776204)

(2s,3s,4r,5r)-2-{[(2r)-1-hydroxy-3-(octadecyloxy)propan-2-yl]oxy}oxane-3,4,5-triol

C26H52O7 (476.3712842)

6,10-dimethyl-10-(4-methyl-3-oxopentyl)-2-methylidenebicyclo[7.2.0]undecan-5-one

C20H32O2 (304.24021719999996)

(1s,3s,6r,7s,8s,9r)-3-[(2r,6r)-6-[(1s,4as,8ar)-4,7-dimethyl-1,2,4a,5,6,8a-hexahydronaphthalen-1-yl]heptan-2-yl]-7,9-dihydroxy-2,4,10-trioxabicyclo[4.3.1]decan-8-yl acetate

C28H44O7 (492.3086874)

(2r,3r,9s,10s,11s)-10-hydroxy-11-methyl-2,9-bis(prop-1-en-2-yl)-4,13-dioxatricyclo[9.2.1.1³,⁶]pentadeca-1(14),6(15)-diene-5,12-dione

C20H24O5 (344.1623654)

(5r,6r,7s,10r)-10-chloro-6,7-dimethyl-6-(2-oxopropyl)-1-oxaspiro[4.5]decan-2-one

C14H21ClO3 (272.1179146)

(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

C22H34O3 (346.25078140000005)

3,10-dimethyl-4h,7h,8h,11h-cyclodeca[b]furan-6-yl acetate

C16H20O3 (260.14123700000005)

methyl 2-[2,5-dihydroxy-4-(3,7,11-trimethyl-9-oxododeca-2,6,10-trien-1-yl)phenyl]acetate

C24H32O5 (400.2249622)

(5s)-3-hexadecyl-5-hydroxy-5-methylfuran-2-one

C21H38O3 (338.2820798)

(2z,5s,11r,12s)-12-hydroxy-3,14-dimethyl-11-(prop-1-en-2-yl)-6,16-dioxatricyclo[11.2.1.1⁵,⁸]heptadeca-1(15),2,8(17),13-tetraen-7-one

C20H24O4 (328.1674504)

(1s,2s,11s,12s)-8-(hydroxymethyl)-1-isopropyl-4,12-dimethyl-15-oxabicyclo[10.2.1]pentadeca-3,7-diene-2,11-diol

C20H34O4 (338.24569640000004)

(5e)-1-(oct-2-en-1-yl)-4-oxo-5-(2-oxoethylidene)cyclopent-2-en-1-yl acetate

C17H22O4 (290.1518012)

(1s,9r,11s,12s,15r,16r,18r)-15-[(2r,5s)-5,6-dimethylheptan-2-yl]-18-hydroxy-2,16-dimethyl-8-oxatetracyclo[9.7.0.0³,⁹.0¹²,¹⁶]octadeca-2,4-dien-7-one

C28H44O3 (428.3290274)

6,14-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,12h,13h,15ah-cyclotetradeca[b]furan-10-carboxylic acid

C20H26O4 (330.18309960000005)

4-hydroxy-5-(hydroxymethyl)-6-methyl-3-[(2r)-6-methylhept-5-en-2-yl]cyclohexa-3,5-diene-1,2-dione

C16H22O4 (278.1518012)

ethyl 2-[(1r,3r,4e,7e,12r)-3,12-dihydroxy-4,8,12-trimethyl-11-oxocyclotetradeca-4,7-dien-1-yl]prop-2-enoate

C22H34O5 (378.24061140000003)

10,14-dihydroxy-3-isopropyl-6,10,14-trimethyl-8-oxo-15-oxatricyclo[9.3.1.0²,⁷]pentadecan-6-yl acetate

C22H36O6 (396.2511756)

(1r,2s)-1-[(1r,4as,8s,9r,11ar)-1-(acetyloxy)-8,9-dihydroxy-7-methyl-11-methylidene-1h,4ah,5h,8h,9h,10h,11ah-cyclonona[c]pyran-4-yl]-1-(acetyloxy)-4-methylpent-3-en-2-yl acetate

C26H36O9 (492.2359206)

(1s,2s,3s,4s,7s,8z,10s,11r,12s,13r,16r,17s)-10,12,16-tris(acetyloxy)-3,4,11,17-tetrahydroxy-4,9,13,17-tetramethyl-5-oxo-6-oxatricyclo[11.4.0.0³,⁷]heptadeca-8,14-dien-2-yl acetate

C28H38O14 (598.2261447999999)

[(3ar,15as)-10,14-dimethyl-3-methylidene-2-oxo-3ah,4h,7h,8h,11h,12h,15h,15ah-cyclotetradeca[b]furan-6-yl]methyl acetate

C22H30O4 (358.214398)

6-{7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methyl-3-methylideneheptan-2-ol

C28H46O2 (414.34976159999997)

4-isopropyl-1,7,11-trimethylcyclotetradeca-2,7,11-trien-1-ol

C20H34O (290.2609514)

[(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

C35H50O11 (646.335295)

(1r,3s,4z,9s)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-en-3-ol

C15H24O (220.18270539999997)

{6,14-dimethyl-3-methylidene-2-oxo-3ah,4h,5h,8h,9h,12h,13h,15ah-cyclotetradeca[b]furan-10-yl}methyl acetate

C22H30O4 (358.214398)

[(1s,2e,4e,8e,12r)-1-isopropyl-8,12-dimethyl-15-oxabicyclo[10.2.1]pentadeca-2,4,8-trien-4-yl]methyl acetate

C22H34O3 (346.25078140000005)

9,11,11-trimethyl-2-methylidenetricyclo[4.3.2.0¹,⁵]undecan-3-yl acetate

C17H26O2 (262.1932696)

(1r,2r,5s,8s)-5-hydroxy-2,6,10,10-tetramethyl-12-oxatricyclo[6.3.1.0¹,⁸]dodec-6-en-9-one

C15H22O3 (250.1568862)

2,16-dimethyl-15-(6-methyl-5-methylideneheptan-2-yl)-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadecane-3,5-diol

C28H46O3 (430.34467659999996)

7,9-dihydroxy-9a,11a-dimethyl-1-(6-methylhept-5-en-2-yl)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-10-yl acetate

C29H46O4 (458.3395916)