NCBI Taxonomy: 6157

Fucoxanthin

C42H58O6 (658.4233)

Fucoxanthin is an epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties. It has a role as an algal metabolite, a CFTR potentiator, a food antioxidant, a neuroprotective agent, a hypoglycemic agent, an apoptosis inhibitor, a hepatoprotective agent, a marine metabolite and a plant metabolite. It is an epoxycarotenol, an acetate ester, a secondary alcohol, a tertiary alcohol and a member of allenes. Fucoxanthin is a natural product found in Aequipecten opercularis, Ascidia zara, and other organisms with data available. Fucoxanthin is a carotenoid, with formula C40H60O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510-525 nm by various estimates and absorbing significantly in the range of 450 to 540 nm. -- Wikipedia [HMDB] Fucoxanthin is a carotenoid, with formula C40H60O6. It is found as an accessory pigment in the chloroplasts of brown algae and most other heterokonts, giving them a brown or olive-green color. Fucoxanthin absorbs light primarily in the blue-green to yellow-green part of the visible spectrum, peaking at around 510-525 nm by various estimates and absorbing significantly in the range of 450 to 540 nm. -- Wikipedia. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Fucoxanthin (all-trans-Fucoxanthin) is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities[1][2][3][4][5][6][7][8][9]. Fucoxanthin is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities. Fucoxanthin (all-trans-Fucoxanthin) is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities[1][2][3][4][5][6][7][8][9]. Fucoxanthin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=3351-86-8 (retrieved 2024-11-06) (CAS RN: 3351-86-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Berberine

[C20H18NO4]+ (336.1236)

Berberine is an organic heteropentacyclic compound, an alkaloid antibiotic, a botanical anti-fungal agent and a berberine alkaloid. It has a role as an antilipemic drug, a hypoglycemic agent, an antioxidant, a potassium channel blocker, an antineoplastic agent, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor, an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor, an EC 1.21.3.3 (reticuline oxidase) inhibitor, an EC 2.1.1.116 [3-hydroxy-N-methyl-(S)-coclaurine 4-O-methyltransferase] inhibitor, an EC 3.1.1.4 (phospholipase A2) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 2.7.11.10 (IkappaB kinase) inhibitor, an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor, a geroprotector and a metabolite. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. Berberine is a quaternary ammonia compound found in many botanical products, including goldenseal, barberry and Oregon grape, which is used for its purported antioxidant and antimicrobial properties for a host of conditions, including obesity, diabetes, hyperlipidemia, heart failure, H. pylori infection and colonic adenoma prevention. Berberine has not been linked to serum aminotransferase elevations during therapy nor to instances of clinically apparent liver injury. Berberine is a natural product found in Berberis poiretii, Thalictrum delavayi, and other organisms with data available. Berberine is a quaternary ammonium salt of an isoquinoline alkaloid and active component of various Chinese herbs, with potential antineoplastic, radiosensitizing, anti-inflammatory, anti-lipidemic and antidiabetic activities. Although the mechanisms of action through which berberine exerts its effects are not yet fully elucidated, upon administration this agent appears to suppress the activation of various proteins and/or modulate the expression of a variety of genes involved in tumorigenesis and inflammation, including, but not limited to transcription factor nuclear factor-kappa B (NF-kB), myeloid cell leukemia 1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), B-cell lymphoma-extra large (Bcl-xl), cyclooxygenase (COX)-2, tumor necrosis factor (TNF), interleukin (IL)-6, IL-12, inducible nitric oxide synthase (iNOS), intercellular adhesion molecule-1 (ICAM-1), E-selectin, monocyte chemoattractant protein-1 (MCP-1), C-X-C motif chemokine 2 (CXCL2), cyclin D1, activator protein (AP-1), hypoxia-inducible factor 1 (HIF-1), signal transducer and activator of transcription 3 (STAT3), peroxisome proliferator-activated receptor (PPAR), arylamine N-acetyltransferase (NAT), and DNA topoisomerase I and II. The modulation of gene expression may induce cell cycle arrest and apoptosis, and inhibit cancer cell proliferation. In addition, berberine modulates lipid and glucose metabolism. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. See also: Goldenseal (part of); Berberis aristata stem (part of). Berberine is a quaternary ammonium salt that belongs to the protoberberine group of benzylisoquinoline alkaloids. Chemically, berberine is classified as an isoquinoline alkaloid. More specifically, berberine is a plant alkaloid derived from tyrosine through a complex 8 step biosynthetic process. Berberine is found in plants such as Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape) and Hydrastis canadensis (goldenseal). Two other known berberine-containing plants are Phellodendron chinense and Phellodendron amurense. Berberine is usually found in the roots, rhizomes, stems, and bark of Berberis plants. Due to berberines intense yellow color, plants that contain berberine were traditionally used to dye wool, leather, and wood. Under ultraviolet light, berberine shows a strong yellow fluorescence, making it useful in histology for staining heparin in mast cells. Berberine is a bioactive plant compound that has been frequently used in traditional medicine. Among the known physiological effects or bioactivities are: 1) Antimicrobial action against bacteria, fungi, protozoa, viruses, helminthes, and Chlamydia; 2) Antagonism against the effects of cholera and E coli heat-stable enterotoxin; 3) Inhibition of intestinal ion secretion and of smooth muscle contraction; 4) Reduction of inflammation and 5) Stimulation of bile secretion and bilirubin discharge (PMID:32335802). Berberine can inhibit bacterial growth in the gut, including Helicobacter pylori, protect the intestinal epithelial barrier from injury, and ameliorate liver injury. Currently, berberine is sold as an Over-the-Counter (OTC) drug for treating gastrointestinal infections in China (PMID:18442638). Berberine also inhibits the proliferation of various types of cancer cells and impedes invasion and metastasis (PMID:32335802). Recent evidence has also confirmed that berberine improves the efficacy and safety of both chemo and radiotherapies for cancer treatment (PMID:32335802). Berberine has also been shown to regulate glucose and lipid metabolism in vitro and in vivo (PMID:18442638). In fact, berberine is the main active component of an ancient Chinese herb Coptis chinensis French, which has been used to treat diabetes for thousands of years. As an anti-diabetic, berberine increases glucose uptake by muscle fibers independent of insulin levels. It triggers AMPK activation and increases glycolysis, leading to decreased insulin resistance and decreased oxygen respiration. The same mechanism leads to a reduction in gluconeogenesis in the liver. AMPK activation by berberine also leads to an antiatherosclerotic effect in mice. Berberines AMPK activation may also underlie berberines anti-obesity effects and favorable influence on weight loss (PMID:18442638). While its use as a medication is widely touted, it is important to remember that berberine inhibits CYP2D6 and CYP3A4 enzymes, both of which are involved in the metabolism of many endogenous substances and xenobiotics, including a number of prescription drugs. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. [HMDB] COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials [Raw Data] CBA98_Berberine_pos_50eV.txt [Raw Data] CBA98_Berberine_pos_10eV.txt [Raw Data] CBA98_Berberine_pos_20eV.txt [Raw Data] CBA98_Berberine_pos_40eV.txt [Raw Data] CBA98_Berberine_pos_30eV.txt Berberine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=2086-83-1 (retrieved 2024-09-04) (CAS RN: 2086-83-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Lovastatin

C24H36O5 (404.2563)

Lovastatin is a fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). It has a role as an Aspergillus metabolite, a prodrug, an anticholesteremic drug and an antineoplastic agent. It is a polyketide, a statin (naturally occurring), a member of hexahydronaphthalenes, a delta-lactone and a fatty acid ester. It is functionally related to a (S)-2-methylbutyric acid and a mevastatin. Lovastatin, also known as the brand name product Mevacor, is a lipid-lowering drug and fungal metabolite derived synthetically from a fermentation product of Aspergillus terreus. Originally named Mevinolin, lovastatin belongs to the statin class of medications, which are used to lower the risk of cardiovascular disease and manage abnormal lipid levels by inhibiting the endogenous production of cholesterol in the liver. More specifically, statin medications competitively inhibit the enzyme hydroxymethylglutaryl-coenzyme A (HMG-CoA) Reductase, which catalyzes the conversion of HMG-CoA to mevalonic acid and is the third step in a sequence of metabolic reactions involved in the production of several compounds involved in lipid metabolism and transport including cholesterol, low-density lipoprotein (LDL) (sometimes referred to as "bad cholesterol"), and very low-density lipoprotein (VLDL). Prescribing of statin medications is considered standard practice following any cardiovascular events and for people with a moderate to high risk of development of CVD, such as those with Type 2 Diabetes. The clear evidence of the benefit of statin use coupled with very minimal side effects or long term effects has resulted in this class becoming one of the most widely prescribed medications in North America. Lovastatin and other drugs from the statin class of medications including [atorvastatin], [pravastatin], [rosuvastatin], [fluvastatin], and [simvastatin] are considered first-line options for the treatment of dyslipidemia. Increasing use of the statin class of drugs is largely due to the fact that cardiovascular disease (CVD), which includes heart attack, atherosclerosis, angina, peripheral artery disease, and stroke, has become a leading cause of death in high-income countries and a major cause of morbidity around the world. Elevated cholesterol levels, and in particular, elevated low-density lipoprotein (LDL) levels, are an important risk factor for the development of CVD. Use of statins to target and reduce LDL levels has been shown in a number of landmark studies to significantly reduce the risk of development of CVD and all-cause mortality. Statins are considered a cost-effective treatment option for CVD due to their evidence of reducing all-cause mortality including fatal and non-fatal CVD as well as the need for surgical revascularization or angioplasty following a heart attack. Evidence has shown that even for low-risk individuals (with <10\\\\% risk of a major vascular event occurring within 5 years) statins cause a 20\\\\%-22\\\\% relative reduction in major cardiovascular events (heart attack, stroke, coronary revascularization, and coronary death) for every 1 mmol/L reduction in LDL without any significant side effects or risks. While all statin medications are considered equally effective from a clinical standpoint, [rosuvastatin] is considered the most potent; doses of 10 to 40mg [rosuvastatin] per day were found in clinical studies to result in a 45.8\\\\% to 54.6\\\\% decrease in LDL cholesterol levels, while lovastatin has been found to have an average decrease in LDL-C of 25-40\\\\%. Potency is thought to correlate to tissue permeability as the more lipophilic statins such as lovastatin are thought to enter endothelial cells by passive diffusion, as opposed to hydrophilic statins such as [pravastatin] and [rosuvastatin] which are taken up into hepatocytes through OATP1B1 (org... Lovastatin is a cholesterol-lowering agent that belongs to the class of medications called statins. It was the second agent of this class discovered. It was discovered by Alfred Alberts and his team at Merck in 1978 after screening only 18 compounds over 2 weeks. The agent, also known as mevinolin, was isolated from the fungi Aspergillus terreus. Research on this compound was suddenly shut down in 1980 and the drug was not approved until 1987. Interesting, Akira Endo at Sankyo Co. (Japan) patented lovastatin isolated from Monascus ruber four months before Merck. Lovastatin was found to be 2 times more potent than its predecessor, mevastatin, the first discovered statin. Like mevastatin, lovastatin is structurally similar to hydroxymethylglutarate (HMG), a substituent of HMG-Coenzyme A (HMG-CoA), a substrate of the cholesterol biosynthesis pathway via the mevalonic acid pathway. Lovastatin is a competitive inhibitor of HMG-CoA reductase with a binding affinity 20,000 times greater than HMG-CoA. Lovastatin differs structurally from mevastatin by a single methyl group at the 6 position. Lovastatin is a prodrug that is activated by in vivo hydrolysis of the lactone ring. It, along with mevastatin, has served as one of the lead compounds for the development of the synthetic compounds used today. A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain > C10AA - Hmg coa reductase inhibitors D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor D009676 - Noxae > D000963 - Antimetabolites CONFIDENCE standard compound; EAWAG_UCHEM_ID 3139 CONFIDENCE standard compound; INTERNAL_ID 2212 Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol. Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.

Maleic acid

C4H4O4 (116.011)

Maleic acid is a colorless crystalline solid having a faint odor. It is combustible though it may take some effort to ignite. It is soluble in water. It is used to make other chemicals and for dyeing and finishing naturally occurring fibers. Maleic acid is a butenedioic acid in which the double bond has cis- (Z)-configuration. It has a role as a plant metabolite, an algal metabolite and a mouse metabolite. It is a conjugate acid of a maleate(1-) and a maleate. Maleic acid is a natural product found in Populus tremula, Ardisia crenata, and other organisms with data available. Maleic Acid is an organic salt or ester of maleic acid that could be conjugated to free base compounds/drugs to improve the physiochemical properties including stability, solubility and dissolution rate. (NCI) Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions. See also: Surfomer (monomer of); Ferropolimaler (monomer of). Maleic acid is an industrial raw material for the production of glyoxylic acid by ozonolysis. Maleic acid is an organic compound which is a dicarboxylic acid (molecule with two carboxyl groups). The molecule consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 degree centigrade) is also much lower than that of fumaric acid (287 degree centigrade). Both properties of maleic acid can be explained on account of the intramolecular hydrogen bonding that takes place at the expense of intermolecular interactions. Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. It reacts with thionyl chloride or phosphorus pentachloride to give the maleic acid chloride (it is not possible to isolate the mono acid chloride). Maleic acid is a reactant in many Diels-Alder reactions. [HMDB]. Maleic acid is found in many foods, some of which are cocoa bean, lovage, roselle, and corn. Maleic acid is a dicarboxylic acid, a molecule with two carboxyl groups. It consists of an ethylene group flanked by two carboxylic acid groups. Maleic acid is the cis isomer of butenedioic acid, whereas fumaric acid is the trans isomer. The cis isomer is the less stable one of the two; the difference in heat of combustion is 22.7 kJ/mol. The physical properties of maleic acid are very different from that of fumaric acid. Maleic acid is soluble in water whereas fumaric acid is not and the melting point of maleic acid (130 - 131 oC) is also much lower than that of fumaric acid (287 oC). Maleic acid is converted into maleic anhydride by dehydration, to malic acid by hydration, and to succinic acid by hydrogenation. Maleic acid is used in making polyesters for fibre-reinforced laminated moldings and paint vehicles. More specifically it is used in the manufacture of phthalic-type alkyd and polyester resins, surface coatings, copolymers, plasticizers, lubricant additives and agricultural chemicals. It is also found in adhesives and sealants and as a preservative for oils and fats. In the natural world, maleic acid has been identified in ginseng, pineapple, cacao plants, sour cherries and corn. A large number of microbes are able to convert maleic acid to D-malate using the enzyme maleate hydratase (PMID: 1444397). A butenedioic acid in which the double bond has cis- (Z)-configuration. Maleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=110-16-7 (retrieved 2024-06-29) (CAS RN: 110-16-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Maleic Acid is a Glutamate Decarboxylase (GAD) inhibitor of E. coli and L. monocytogenes. Maleic Acid is a Glutamate Decarboxylase (GAD) inhibitor of E. coli and L. monocytogenes.

Fumaric acid

C4H4O4 (116.011)

Fumaric acid appears as a colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses. Fumaric acid is a butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle. It has a role as a food acidity regulator, a fundamental metabolite and a geroprotector. It is a conjugate acid of a fumarate(1-). Fumaric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. Fumarate has recently been recognized as an oncometabolite. (A15199). As a food additive, fumaric acid is used to impart a tart taste to processed foods. It is also used as an antifungal agent in boxed foods such as cake mixes and flours, as well as tortillas. Fumaric acid is also added to bread to increase the porosity of the final baked product. It is used to impart a sour taste to sourdough and rye bread. In cake mixes, it is used to maintain a low pH and prevent clumping of the flours used in the mix. In fruit drinks, fumaric acid is used to maintain a low pH which, in turn, helps to stabilize flavor and color. Fumaric acid also prevents the growth of E. coli in beverages when used in combination with sodium benzoate. When added to wines, fumaric acid helps to prevent further fermentation and yet maintain low pH and eliminate traces of metallic elements. In this fashion, it helps to stabilize the taste of wine. Fumaric acid can also be added to dairy products, sports drinks, jams, jellies and candies. Fumaric acid helps to break down bonds between gluten proteins in wheat and helps to create a more pliable dough. Fumaric acid is used in paper sizing, printer toner, and polyester resin for making molded walls. Fumaric acid is a dicarboxylic acid. It is a precursor to L-malate in the Krebs tricarboxylic acid (TCA) cycle. It is formed by the oxidation of succinic acid by succinate dehydrogenase. Fumarate is converted by the enzyme fumarase to malate. Fumaric acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by fumarate. Fumaric acid is found to be associated with fumarase deficiency, which is an inborn error of metabolism. It is also a metabolite of Aspergillus. Produced industrially by fermentation of Rhizopus nigricans, or manufactured by catalytic or thermal isomerisation of maleic anhydride or maleic acid. Used as an antioxidant, acidulant, leavening agent and flavouring agent in foods. Present in raw lean fish. Dietary supplement. Used in powdered products since fumaric acid is less hygroscopic than other acids. A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase (wikipedia). Fumaric acid is also found in garden tomato, papaya, wild celery, and star fruit. Fumaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=110-17-8 (retrieved 2024-07-01) (CAS RN: 110-17-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite. Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

Succinic acid

C4H6O4 (118.0266)

Succinic acid appears as white crystals or shiny white odorless crystalline powder. pH of 0.1 molar solution: 2.7. Very acid taste. (NTP, 1992) Succinic acid is an alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle. It has a role as a nutraceutical, a radiation protective agent, an anti-ulcer drug, a micronutrient and a fundamental metabolite. It is an alpha,omega-dicarboxylic acid and a C4-dicarboxylic acid. It is a conjugate acid of a succinate(1-). A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawleys Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851) Succinic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Succinic acid is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. Succinic acid is created as a byproduct of the fermentation of sugar. It lends to fermented beverages such as wine and beer a common taste that is a combination of saltiness, bitterness and acidity. Succinate is commonly used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. Succinate plays a role in the citric acid cycle, an energy-yielding process and is metabolized by succinate dehydrogenase to fumarate. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle. Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e.g. malate. (A3509) Mutations in the four genes encoding the subunits of succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntingtons disease. (A3510). Succinate also acts as an oncometabolite. Succinate inhibits 2-oxoglutarate-dependent histone and DNA demethylase enzymes, resulting in epigenetic silencing that affects neuroendocrine differentiation. A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawleys Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851) Succinic acid (succinate) is a dicarboxylic acid. It is an important component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain. Succinate is found in all living organisms ranging from bacteria to plants to mammals. In eukaryotes, succinate is generated in the mitochondria via the tricarboxylic acid cycle (TCA). Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate (PMID 16143825). Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space. Succinate has multiple biological roles including roles as a metabolic intermediate and roles as a cell signalling molecule. Succinate can alter gene expression patterns, thereby modulating the epigenetic landscape or it can exhibit hormone-like signaling functions (PMID: 26971832). As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. Succinate can be broken down or metabolized into fumarate by the enzyme succinate dehydrogenase (SDH), which is part of the electron transport chain involved in making ATP. Dysregulation of succinate synthesis, and therefore ATP synthesis, can happen in a number of genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome. Succinate has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Succinic acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by succinate. In humans, urinary succinic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis (PMID: 22292465). Succinic acid is also found in Actinobacillus, Anaerobiospirillum, Mannheimia, Corynebacterium and Basfia (PMID: 22292465; PMID: 18191255; PMID: 26360870). Succinic acid is widely distributed in higher plants and produced by microorganisms. It is found in cheeses and fresh meats. Succinic acid is a flavouring enhancer, pH control agent [DFC]. Succinic acid is also found in yellow wax bean, swamp cabbage, peanut, and abalone. An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID S004 Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2]. Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2].

Hyoscyamine

C17H23NO3 (289.1678)

(S)-atropine is an atropine with a 2S-configuration. It is functionally related to a (S)-tropic acid. It is a conjugate base of a (S)-atropinium. Hyoscyamine is a tropane alkaloid and the levo-isomer of [atropine]. It is commonly extracted from plants in the Solanaceae or nightshade family. Research into the action of hyoscyamine in published literature dates back to 1826. Hyoscyamine is used for a wide variety of treatments and therapeutics due to its antimuscarinic properties. Although hyoscyamine is marketed in the United States, it is not FDA approved. Hyoscyamine as a natural plant alkaloid derivative and anticholinergic that is used to treat mild to moderate nausea, motion sickness, hyperactive bladder and allergic rhinitis. Hyoscyamine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury. L-Hyoscyamine is a natural product found in Datura ferox, Crenidium spinescens, and other organisms with data available. Hyoscyamine is a belladonna alkaloid derivative and the levorotatory form of racemic atropine isolated from the plants Hyoscyamus niger or Atropa belladonna, which exhibits anticholinergic activity. Hyoscyamine functions as a non-selective, competitive antagonist of muscarinic receptors, thereby inhibiting the parasympathetic activities of acetylcholine on the salivary, bronchial, and sweat glands, as well as the eye, heart, bladder, and gastrointestinal tract. These inhibitory effects cause a decrease in saliva, bronchial mucus, gastric juices, and sweat. Furthermore, its inhibitory action on smooth muscle prevents bladder contraction and decreases gastrointestinal motility. The 3(S)-endo isomer of atropine. Hyoscyamine is a chemical compound, a tropane alkaloid it is the levo-isomer to atropine. It is a secondary metabolite of some plants, particularly henbane (Hyoscamus niger.). Hyoscyamine is used to provide symptomatic relief to various gastrointestinal disorders including spasms, peptic ulcers, irritable bowel syndrome, pancreatitis, colic and cystitis. It has also been used to relieve some heart problems, control some of the symptoms of Parkinsons disease, as well as for control of respiratory secretions in end of life care. A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03B - Belladonna and derivatives, plain > A03BA - Belladonna alkaloids, tertiary amines C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2269 D002491 - Central Nervous System Agents KEIO_ID H045; [MS2] KO008998 KEIO_ID H045 L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2]. L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2]. L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2].

beta-Carotene

C40H56 (536.4382)

Beta-carotene is a cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. It has a role as a biological pigment, a provitamin A, a plant metabolite, a human metabolite, a mouse metabolite, a cofactor, a ferroptosis inhibitor and an antioxidant. It is a cyclic carotene and a carotenoid beta-end derivative. Beta-carotene, with the molecular formula C40H56, belongs to the group of carotenoids consisting of isoprene units. The presence of long chains of conjugated double bonds donates beta-carotene with specific colors. It is the most abundant form of carotenoid and it is a precursor of the vitamin A. Beta-carotene is composed of two retinyl groups. It is an antioxidant that can be found in yellow, orange and green leafy vegetables and fruits. Under the FDA, beta-carotene is considered as a generally recognized as safe substance (GRAS). Beta-Carotene is a natural product found in Epicoccum nigrum, Lonicera japonica, and other organisms with data available. Beta-Carotene is a naturally-occurring retinol (vitamin A) precursor obtained from certain fruits and vegetables with potential antineoplastic and chemopreventive activities. As an anti-oxidant, beta carotene inhibits free-radical damage to DNA. This agent also induces cell differentiation and apoptosis of some tumor cell types, particularly in early stages of tumorigenesis, and enhances immune system activity by stimulating the release of natural killer cells, lymphocytes, and monocytes. (NCI04) beta-Carotene is a metabolite found in or produced by Saccharomyces cerevisiae. A carotenoid that is a precursor of VITAMIN A. Beta carotene is administered to reduce the severity of photosensitivity reactions in patients with erythropoietic protoporphyria (PORPHYRIA, ERYTHROPOIETIC). See also: Lycopene (part of); Broccoli (part of); Lycium barbarum fruit (part of). Beta-Carotene belongs to the class of organic compounds known as carotenes. These are a type of polyunsaturated hydrocarbon molecules containing eight consecutive isoprene units. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Beta-carotene is therefore considered to be an isoprenoid lipid molecule. Beta-carotene is a strongly coloured red-orange pigment abundant in fungi, plants, and fruits. It is synthesized biochemically from eight isoprene units and therefore has 40 carbons. Among the carotenes, beta-carotene is distinguished by having beta-rings at both ends of the molecule. Beta-Carotene is biosynthesized from geranylgeranyl pyrophosphate. It is the most common form of carotene in plants. In nature, Beta-carotene is a precursor (inactive form) to vitamin A. Vitamin A is produed via the action of beta-carotene 15,15-monooxygenase on carotenes. In mammals, carotenoid absorption is restricted to the duodenum of the small intestine and dependent on a class B scavenger receptor (SR-B1) membrane protein, which is also responsible for the absorption of vitamin E. One molecule of beta-carotene can be cleaved by the intestinal enzyme Beta-Beta-carotene 15,15-monooxygenase into two molecules of vitamin A. Beta-Carotene contributes to the orange color of many different fruits and vegetables. Vietnamese gac and crude palm oil are particularly rich sources, as are yellow and orange fruits, such as cantaloupe, mangoes, pumpkin, and papayas, and orange root vegetables such as carrots and sweet potatoes. Excess beta-carotene is predominantly stored in the fat tissues of the body. The most common side effect of excessive beta-carotene consumption is carotenodermia, a physically harmless condition that presents as a conspicuous orange skin tint arising from deposition of the carotenoid in the outermost layer of the epidermis. Yellow food colour, dietary supplement, nutrient, Vitamin A precursor. Nutriceutical with antioxidation props. beta-Carotene is found in many foods, some of which are summer savory, gram bean, sunburst squash (pattypan squash), and other bread product. A cyclic carotene obtained by dimerisation of all-trans-retinol. A strongly-coloured red-orange pigment abundant in plants and fruit and the most active and important provitamin A carotenoid. D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BB - Protectives against uv-radiation for systemic use A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins

Hyoscyamine

C17H23NO3 (289.1678)

Atropine is a racemate composed of equimolar concentrations of (S)- and (R)-atropine. It is obtained from deadly nightshade (Atropa belladonna) and other plants of the family Solanaceae. It has a role as a muscarinic antagonist, an anaesthesia adjuvant, an anti-arrhythmia drug, a mydriatic agent, a parasympatholytic, a bronchodilator agent, a plant metabolite, an antidote to sarin poisoning and a oneirogen. It contains a (S)-atropine and a (R)-atropine. Atropine is an alkaloid originally synthesized from Atropa belladonna. It is a racemic mixture of d-and l-hyoscyamine, of which only l-hyoscyamine is pharmacologically active. Atropine is generally available as a sulfate salt and can be administered by intravenous, subcutaneous, intramuscular, intraosseous, endotracheal and ophthalmic methods. Oral atropine is only available in combination products. Atropine is a competitive, reversible antagonist of muscarinic receptors that blocks the effects of acetylcholine and other choline esters. It has a variety of therapeutic applications, including pupil dilation and the treatment of anticholinergic poisoning and symptomatic bradycardia in the absence of reversible causes. Atropine is a relatively inexpensive drug and is included in the World Health Organization List of Essential Medicines. Atropine is an Anticholinergic and Cholinergic Muscarinic Antagonist. The mechanism of action of atropine is as a Cholinergic Antagonist and Cholinergic Muscarinic Antagonist. Hyoscyamine as a natural plant alkaloid derivative and anticholinergic that is used to treat mild to moderate nausea, motion sickness, hyperactive bladder and allergic rhinitis. Hyoscyamine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury. Atropine is a natural product found in Cyphanthera tasmanica, Anthocercis ilicifolia, and other organisms with data available. Atropine Sulfate is the sulfate salt of atropine, a naturally-occurring alkaloid isolated from the plant Atropa belladonna. Atropine functions as a sympathetic, competitive antagonist of muscarinic cholinergic receptors, thereby abolishing the effects of parasympathetic stimulation. This agent may induce tachycardia, inhibit secretions, and relax smooth muscles. (NCI04) Atropine is a synthetically-derived form of the endogenous alkaloid isolated from the plant Atropa belladonna. Atropine functions as a sympathetic, competitive antagonist of muscarinic cholinergic receptors, thereby abolishing the effects of parasympathetic stimulation. This agent may induce tachycardia, inhibit secretions, and relax smooth muscles. (NCI04) Hyoscyamine is a belladonna alkaloid derivative and the levorotatory form of racemic atropine isolated from the plants Hyoscyamus niger or Atropa belladonna, which exhibits anticholinergic activity. Hyoscyamine functions as a non-selective, competitive antagonist of muscarinic receptors, thereby inhibiting the parasympathetic activities of acetylcholine on the salivary, bronchial, and sweat glands, as well as the eye, heart, bladder, and gastrointestinal tract. These inhibitory effects cause a decrease in saliva, bronchial mucus, gastric juices, and sweat. Furthermore, its inhibitory action on smooth muscle prevents bladder contraction and decreases gastrointestinal motility. An alkaloid, originally from Atropa belladonna, but found in other plants, mainly SOLANACEAE. Hyoscyamine is the 3(S)-endo isomer of atropine. A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03B - Belladonna and derivatives, plain > A03BA - Belladonna alkaloids, tertiary amines S - Sensory organs > S01 - Ophthalmologicals > S01F - Mydriatics and cycloplegics > S01FA - Anticholinergics C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2292 INTERNAL_ID 2292; CONFIDENCE Reference Standard (Level 1) CONFIDENCE standard compound; EAWAG_UCHEM_ID 3334 D002491 - Central Nervous System Agents KEIO_ID A080; [MS2] KO008864 KEIO_ID A080 Atropine (Tropine tropate) is a competitive muscarinic acetylcholine receptor (mAChR) antagonist with IC50 values of 0.39 and 0.71 nM for Human mAChR M4 and Chicken mAChR M4, respectively. Atropine inhibits ACh-induced relaxations in human pulmonary veins. Atropine can be used for research of anti-myopia and bradycardia[1][2][3][4]. Atropine (Tropine tropate) is a competitive muscarinic acetylcholine receptor (mAChR) antagonist with IC50 values of 0.39 and 0.71 nM for Human mAChR M4 and Chicken mAChR M4, respectively. Atropine inhibits ACh-induced relaxations in human pulmonary veins. Atropine can be used for research of anti-myopia and bradycardia[1][2][3][4]. Atropine (Tropine tropate) is a competitive muscarinic acetylcholine receptor (mAChR) antagonist with IC50 values of 0.39 and 0.71 nM for Human mAChR M4 and Chicken mAChR M4, respectively. Atropine inhibits ACh-induced relaxations in human pulmonary veins. Atropine can be used for research of anti-myopia and bradycardia[1][2][3][4]. L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2]. L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2]. L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2].

Oxoglutaric acid

C5H6O5 (146.0215)

Oxoglutaric acid, also known as alpha-ketoglutarate, alpha-ketoglutaric acid, AKG, or 2-oxoglutaric acid, is classified as a gamma-keto acid or a gamma-keto acid derivative. gamma-Keto acids are organic compounds containing an aldehyde substituted with a keto group on the C4 carbon atom. alpha-Ketoglutarate is considered to be soluble (in water) and acidic. alpha-Ketoglutarate is a key molecule in the TCA cycle, playing a fundamental role in determining the overall rate of this important metabolic process (PMID: 26759695). In the TCA cycle, AKG is decarboxylated to succinyl-CoA and carbon dioxide by AKG dehydrogenase, which functions as a key control point of the TCA cycle. Additionally, AKG can be generated from isocitrate by oxidative decarboxylation catalyzed by the enzyme known as isocitrate dehydrogenase (IDH). In addition to these routes of production, AKG can be produced from glutamate by oxidative deamination via glutamate dehydrogenase, and as a product of pyridoxal phosphate-dependent transamination reactions (mediated by branched-chain amino acid transaminases) in which glutamate is a common amino donor. AKG is a nitrogen scavenger and a source of glutamate and glutamine that stimulates protein synthesis and inhibits protein degradation in muscles. In particular, AKG can decrease protein catabolism and increase protein synthesis to enhance bone tissue formation in skeletal muscles (PMID: 26759695). Interestingly, enteric feeding of AKG supplements can significantly increase circulating plasma levels of hormones such as insulin, growth hormone, and insulin-like growth factor-1 (PMID: 26759695). It has recently been shown that AKG can extend the lifespan of adult C. elegans by inhibiting ATP synthase and TOR (PMID: 24828042). In combination with molecular oxygen, alpha-ketoglutarate is required for the hydroxylation of proline to hydroxyproline in the production of type I collagen. A recent study has shown that alpha-ketoglutarate promotes TH1 differentiation along with the depletion of glutamine thereby favouring Treg (regulatory T-cell) differentiation (PMID: 26420908). alpha-Ketoglutarate has been found to be associated with fumarase deficiency, 2-ketoglutarate dehydrogenase complex deficiency, and D-2-hydroxyglutaric aciduria, which are all inborn errors of metabolism (PMID: 8338207). Oxoglutaric acid has been found to be a metabolite produced by Corynebacterium and yeast (PMID: 27872963) (YMDB). [Spectral] 2-Oxoglutarate (exact mass = 146.02152) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] 2-Oxoglutarate (exact mass = 146.02152) and (S)-Malate (exact mass = 134.02152) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Flavouring ingredient

Scopolamine

C17H21NO4 (303.1471)

Scopolamine, also known as hyoscine, is a tropane alkaloid drug obtained from plants of the family Solanaceae (nightshades), such as henbane or jimson weed (Datura species). It is part of the secondary metabolites of plants. Scopolamine is used criminally as a date rape drug and as an aid to robbery, the most common act being the clandestine drugging of a victims drink. It is preferred because it induces retrograde amnesia, or an inability to recall events prior to its administration. Victims of this crime are often admitted to a hospital in police custody, under the assumption that the patient is experiencing a psychotic episode. A telltale sign is a fever accompanied by a lack of sweat. An alkaloid from Solanaceae, especially Datura metel L. and Scopola carniolica. Scopolamine and its quaternary derivatives act as antimuscarinics like atropine, but may have more central nervous system effects. Among the many uses are as an anesthetic premedication, in urinary incontinence, in motion sickness, as an antispasmodic, and as a mydriatic and cycloplegic. Scopolamine, also known as hyoscine, is a tropane alkaloid drug obtained from plants of the family Solanaceae (nightshades), such as henbane or jimson weed (Datura species). It is part of the secondary metabolites of plants. A - Alimentary tract and metabolism > A04 - Antiemetics and antinauseants > A04A - Antiemetics and antinauseants S - Sensory organs > S01 - Ophthalmologicals > S01F - Mydriatics and cycloplegics > S01FA - Anticholinergics C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics C78283 - Agent Affecting Organs of Special Senses > C29706 - Mydriatic Agent N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives D005765 - Gastrointestinal Agents > D000932 - Antiemetics D002491 - Central Nervous System Agents KEIO_ID S040; [MS2] KO009233 KEIO_ID S040

Cholesterol

C27H46O (386.3548)

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

Hygrine

C8H15NO (141.1154)

Hygrine, also known as (+)-hygrine or (+)-N-methyl-2-acetonylpyrrolidine, belongs to alkaloids and derivatives class of compounds. Those are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic propertiesand is also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus. Hygrine is soluble (in water) and an extremely weak acidic compound (based on its pKa). Hygrine can be found in pomegranate, which makes hygrine a potential biomarker for the consumption of this food product. Hygrine is a pyrrolidine alkaloid, found mainly in coca leaves (0.2\\%). It was first isolated by Carl Liebermann in 1889 (along with a related compound cuscohygrine) as an alkaloid accompanying cocaine in coca. Hygrine is extracted as a thick yellow oil, having a pungent taste and odor .

Diadinoxanthin

C40H54O3 (582.4073)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

trans-Aconitic acid

C6H6O6 (174.0164)

trans-Aconitic acid, also known as trans-aconitate or (e)-aconitic acid, belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. trans-Aconitic acid exists in all living species, ranging from bacteria to humans. trans-Aconitic acid is a dry, musty, and nut tasting compound. Outside of the human body, trans-aconitic acid has been detected, but not quantified in several different foods, such as garden tomato fruits, root vegetables, soy beans, and rices. trans-Aconitic acid is normally present in human urine, and it has been suggested that is present in larger amounts with Reyes syndrome and organic aciduria. trans-Aconitic acid in the urine is a biomarker for the consumption of soy products. trans-Aconitic acid is a substrate of enzyme trans-Aconitic acid 2-methyltransferase (EC2.1.1.144). Isolated from Asarum europaeum, from cane-sugar molasses, roasted chicory root, roasted malt barley, passion fruit, sorghum root and sugar beet. Flavouring agent used in fruit flavours and alcoholic beverages. Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerisation of citrate to isocitrate in the citric acid cycle. It is acted upon by aconitase. Trans-aconitate in the urine is a biomarker for the consumption of soy products. (E)-Aconitic acid is found in many foods, some of which are cereals and cereal products, rice, garden tomato (variety), and root vegetables. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID A117 trans-Aconitic acid is present in normal human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid is a substrate of enzyme trans-aconitate 2-methyltransferase. trans-Aconitic acid is present in normal human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid is a substrate of enzyme trans-aconitate 2-methyltransferase.

trans-beta-Terpineol

C10H18O (154.1358)

trans-beta-Terpineol is found in rosemary. Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. (Wikipedia). Terpineol is a naturally occurring monoterpene alcohol that has been isolated from a variety of sources such as cajuput oil, pine oil, and petitgrain oil. There are three isomers, alpha-, beta-, and gamma-terpineol, the last two differing only by the location of the double bond. Terpineol is usually a mixture of these isomers with alpha-terpineol as the major constituent. trans-beta-Terpineol is found in rosemary.

Aconitic acid

C6H6O6 (174.0164)

But-2-enedioic acid

C4H4O4 (116.011)

Monascin

C21H26O5 (358.178)

Tropine

C8H15NO (141.1154)

Pseudotropine, also known as tropine hydrochloride, (endo)-isomer or tropine, (exo)-isomer, is a member of the class of compounds known as tropane alkaloids. Tropane alkaloids are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Pseudotropine is soluble (in water) and an extremely weak acidic compound (based on its pKa). Pseudotropine can be found in a number of food items such as winter savory, japanese chestnut, blackcurrant, and black walnut, which makes pseudotropine a potential biomarker for the consumption of these food products. Pseudotropine (3β-tropanol, ψ-tropine, 3-pseudotropanol or PTO) is a derivative of tropane and an isomer of tropine . Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2]. Tropine is a secondary metabolite of Solanaceae plants, is an anticholinergic agent[1]. Tropine is a common intermediate in the synthesis of a variety of bioactive alkaloids, including hyoscyamine and scopolamine[2].

Scopolamine

C17H21NO4 (303.1471)

A - Alimentary tract and metabolism > A04 - Antiemetics and antinauseants > A04A - Antiemetics and antinauseants S - Sensory organs > S01 - Ophthalmologicals > S01F - Mydriatics and cycloplegics > S01FA - Anticholinergics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics N - Nervous system > N05 - Psycholeptics > N05C - Hypnotics and sedatives D005765 - Gastrointestinal Agents > D000932 - Antiemetics D002491 - Central Nervous System Agents Scopolamine hydrobromide appears as colorless crystals or white powder or solid. Has no odor. pH (of 5\\% solution): 4-5.5. Slightly efflorescent in dry air. Bitter, acrid taste. (NTP, 1992) Scopolamine is a tropane alkaloid that is the (S)-tropic acid ester of 6beta,7beta-epoxy-1alphaH,5alphaH-tropan-3alpha-ol. It has a role as a muscarinic antagonist, an antiemetic, an adjuvant, a mydriatic agent, an antispasmodic drug, an anaesthesia adjuvant, an antidepressant and a metabolite. It is a propanoate ester, an epoxide, a tertiary amino compound and a tropane alkaloid. It is functionally related to a (S)-tropic acid. It is a conjugate base of a scopolamine(1+). Scopolamine is a tropane alkaloid isolated from members of the Solanaceae family of plants, similar to [atropine] and [hyoscyamine], all of which structurally mimic the natural neurotransmitter [acetylcholine]. Scopolamine was first synthesized in 1959, but to date, synthesis remains less efficient than extracting scopolamine from plants. As an acetylcholine analogue, scopolamine can antagonize muscarinic acetylcholine receptors (mAChRs) in the central nervous system and throughout the body, inducing several therapeutic and adverse effects related to alteration of parasympathetic nervous system and cholinergic signalling. Due to its dose-dependent adverse effects, scopolamine was the first drug to be offered commercially as a transdermal delivery system, Scopoderm TTS®, in 1981. As a result of its anticholinergic effects, scopolamine is being investigated for diverse therapeutic applications; currently, it is approved for the prevention of nausea and vomiting associated with motion sickness and surgical procedures. Scopolamine was first approved by the FDA on December 31, 1979, and is currently available as both oral tablets and a transdermal delivery system. Scopolamine is an Anticholinergic. The mechanism of action of scopolamine is as a Cholinergic Antagonist. Hyoscine is a natural product found in Duboisia leichhardtii, Duboisia myoporoides, and other organisms with data available. Scopolamine is a tropane alkaloid derived from plants of the nightshade family (Solanaceae), specifically Hyoscyamus niger and Atropa belladonna, with anticholinergic, antiemetic and antivertigo properties. Structurally similar to acetylcholine, scopolamine antagonizes acetylcholine activity mediated by muscarinic receptors located on structures innervated by postganglionic cholinergic nerves as well as on smooth muscles that respond to acetylcholine but lack cholinergic innervation. The agent is used to cause mydriasis, cycloplegia, to control the secretion of saliva and gastric acid, to slow gut motility, and prevent vomiting. An alkaloid from SOLANACEAE, especially DATURA and SCOPOLIA. Scopolamine and its quaternary derivatives act as antimuscarinics like ATROPINE, but may have more central nervous system effects. Its many uses include an anesthetic premedication, the treatment of URINARY INCONTINENCE and MOTION SICKNESS, an antispasmodic, and a mydriatic and cycloplegic. A tropane alkaloid that is the (S)-tropic acid ester of 6beta,7beta-epoxy-1alphaH,5alphaH-tropan-3alpha-ol. C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent C78283 - Agent Affecting Organs of Special Senses > C29706 - Mydriatic Agent CONFIDENCE standard compound; INTERNAL_ID 1149; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5225; ORIGINAL_PRECURSOR_SCAN_NO 5222 CONFIDENCE standard compound; INTERNAL_ID 1149; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5230; ORIGINAL_PRECURSOR_SCAN_NO 5228 CONFIDENCE standard compound; INTERNAL_ID 1149; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5252; ORIGINAL_PRECURSOR_SCAN_NO 5251 CONFIDENCE standard compound; INTERNAL_ID 1149; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5243; ORIGINAL_PRECURSOR_SCAN_NO 5241 CONFIDENCE standard compound; INTERNAL_ID 1149; DATASET 20200303_ENTACT_RP_MIX503; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5254; ORIGINAL_PRECURSOR_SCAN_NO 5252 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2318 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.290 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.274 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.276

Monascin

C21H26O5 (358.178)

Monascin is an organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours. It has a role as an antineoplastic agent, a PPARgamma agonist, an antilipemic drug and a fungal metabolite. It is an organic heterotricyclic compound, a gamma-lactone, an alpha,beta-unsaturated ketone and a polyketide. Monascin is a natural product found in Monascus kaoliang, Monascus purpureus, and Monascus pilosus with data available. An organic heterotricyclic compound that is 3a,4,8,9a-tetrahydro-2H-furo[3,2-g][2]benzopyran-2,9(3H)-dione that is substituted at positions 3, 6, and 9a by hexanoyl, (1E)-prop-1-en-1-yl and methyl groups, respectively (the 3S,3aR,9aR diastereoisomer). One of the azaphilonoid pigments in extracts of Monascus pilosus-fermented rice (red-mould rice), it is a potent inhibitor of carcinogenesis measured against chemical- or UV-initiated, phorbol-promoted mouse skin tumours.

Cephamonine

C20H25NO5 (359.1733)

Maleic Acid

C4H4O4 (116.011)

D004791 - Enzyme Inhibitors Maleic Acid is a Glutamate Decarboxylase (GAD) inhibitor of E. coli and L. monocytogenes. Maleic Acid is a Glutamate Decarboxylase (GAD) inhibitor of E. coli and L. monocytogenes.

20-Hydroxyecdysone

C27H44O7 (480.3087)

Berberine

C20H17NO4 (335.1158)

Cholesterol

C27H46O (386.3548)

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

Berberine

[C20H18NO4]+ (336.1236)

Origin: Plant; SubCategory_DNP: Isoquinoline alkaloids, Benzylisoquinoline alkaloids COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2521; CONFIDENCE confident structure IPB_RECORD: 821; CONFIDENCE confident structure

Lovastatin

C24H36O5 (404.2563)

C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain > C10AA - Hmg coa reductase inhibitors D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor CONFIDENCE standard compound; INTERNAL_ID 2212 D009676 - Noxae > D000963 - Antimetabolites relative retention time with respect to 9-anthracene Carboxylic Acid is 1.415 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.416 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.421 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.419 Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol. Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.

β-Carotene

C40H56 (536.4382)

The novel carbohydrate-derived b-carboline, 1-pentahydroxypentyl-1,2,3,4-tetrahydro-b-carboline-3-carboxylic acid, was identified in fruit- and vegetable-derived products such as juices, jams, and tomato sauces. This compound occurred as two diastereoisomers, a cis isomer (the major compound) and a trans isomer, ranging from undetectable amounts to 6.5 ug/g. Grape, tomato, pineapple, and tropical juices exhibited the highest amount of this alkaloid (up to 3.8 mg/L), whereas apple, banana, and peach juices showed very low or nondetectable levels. This tetrahydro-b-carboline was also found in jams (up to 0.45 ug/g), and a relative high amount was present in tomato concentrate (6.5 ug/g) and sauce (up to 1.8 ug/g). This b-carboline occurred in fruit-derived products as a glycoconjugate from a chemical condensation of d-glucose and l-tryptophan that is highly favored at low pH values and high temperature. Production, processing treatments, and storage of fruit juices and jams can then release this b-carboline. Fruit-derived products and other foods containing this compound might be an exogenous dietary source of this glucose-derived tetrahydro-b-carboline.(PMID: 12137498) [HMDB] Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE is 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. D - Dermatologicals > D02 - Emollients and protectives > D02B - Protectives against uv-radiation > D02BB - Protectives against uv-radiation for systemic use A - Alimentary tract and metabolism > A11 - Vitamins > A11C - Vitamin a and d, incl. combinations of the two > A11CA - Vitamin a, plain D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE is 10 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.

Succinic acid

C4H6O4 (118.0266)

Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2]. Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2].

trans-Aconitic acid

C6H6O6 (174.0164)

The trans-isomer of aconitic acid. trans-Aconitic acid is present in normal human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid is a substrate of enzyme trans-aconitate 2-methyltransferase. trans-Aconitic acid is present in normal human urine, and it has been suggested that is present in larger amounts with Reye's syndrome and organic aciduria. trans-Aconitic acid is a substrate of enzyme trans-aconitate 2-methyltransferase.

Fumaric Acid

C4H4O4 (116.011)

Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite. Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

Fucoxanthin

C42H58O6 (658.4233)

Fucoxanthin is an epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties. It has a role as an algal metabolite, a CFTR potentiator, a food antioxidant, a neuroprotective agent, a hypoglycemic agent, an apoptosis inhibitor, a hepatoprotective agent, a marine metabolite and a plant metabolite. It is an epoxycarotenol, an acetate ester, a secondary alcohol, a tertiary alcohol and a member of allenes. Fucoxanthin is a natural product found in Aequipecten opercularis, Ascidia zara, and other organisms with data available. An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties. 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 for selecting the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 16HP2005 to the Mass Spectrometry Society of Japan. Fucoxanthin (all-trans-Fucoxanthin) is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities[1][2][3][4][5][6][7][8][9]. Fucoxanthin is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities. Fucoxanthin (all-trans-Fucoxanthin) is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities[1][2][3][4][5][6][7][8][9]. Fucoxanthin is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities.

Aconitic acid

C6H6O6 (174.0164)

Aconitic acid is an organic acid. The two isomers are cis-aconitic acid and trans-aconitic acid. The conjugate base of cis-aconitic acid, cis-aconitate is an intermediate in the isomerisation of citrate to isocitrate in the citric acid cycle. It is acted upon by aconitase. Aconitic acid is found in many foods, some of which are oat, barley, red beetroot, and sunflower. Annotation level-2

Hyoscyamine

C17H23NO3 (289.1678)

(S)-atropine is an atropine with a 2S-configuration. It is functionally related to a (S)-tropic acid. It is a conjugate base of a (S)-atropinium. Hyoscyamine is a tropane alkaloid and the levo-isomer of [atropine]. It is commonly extracted from plants in the Solanaceae or nightshade family. Research into the action of hyoscyamine in published literature dates back to 1826. Hyoscyamine is used for a wide variety of treatments and therapeutics due to its antimuscarinic properties. Although hyoscyamine is marketed in the United States, it is not FDA approved. Hyoscyamine as a natural plant alkaloid derivative and anticholinergic that is used to treat mild to moderate nausea, motion sickness, hyperactive bladder and allergic rhinitis. Hyoscyamine has not been implicated in causing liver enzyme elevations or clinically apparent acute liver injury. L-Hyoscyamine is a natural product found in Datura ferox, Crenidium spinescens, and other organisms with data available. Hyoscyamine is a belladonna alkaloid derivative and the levorotatory form of racemic atropine isolated from the plants Hyoscyamus niger or Atropa belladonna, which exhibits anticholinergic activity. Hyoscyamine functions as a non-selective, competitive antagonist of muscarinic receptors, thereby inhibiting the parasympathetic activities of acetylcholine on the salivary, bronchial, and sweat glands, as well as the eye, heart, bladder, and gastrointestinal tract. These inhibitory effects cause a decrease in saliva, bronchial mucus, gastric juices, and sweat. Furthermore, its inhibitory action on smooth muscle prevents bladder contraction and decreases gastrointestinal motility. The 3(S)-endo isomer of atropine. A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03B - Belladonna and derivatives, plain > A03BA - Belladonna alkaloids, tertiary amines C78272 - Agent Affecting Nervous System > C66880 - Anticholinergic Agent > C29704 - Antimuscarinic Agent D019141 - Respiratory System Agents > D018927 - Anti-Asthmatic Agents > D001993 - Bronchodilator Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D010276 - Parasympatholytics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D009184 - Mydriatics D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D002491 - Central Nervous System Agents An atropine with a 2S-configuration. Annotation level-1 L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2]. L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2]. L-Hyoscyamine (Daturine), a natural plant tropane alkaloid, is a potent and competitive muscarinic receptor (MR) antagonist. L-Hyoscyamine is a levo-isomer to Atropine (HY-B1205)[1][2].

Oxoglutarate

C5H6O5 (146.0215)

Berberine

C20H18NO4+ (336.1236)

eudesmic acid

C10H12O5 (212.0685)

3,4,5-Trimethoxybenzoic acid (Eudesmic acid;Trimethylgallic Acid) is a benzoic acid derivative. A building block in medicine and organic synthesis. 3,4,5-Trimethoxybenzoic acid (Eudesmic acid;Trimethylgallic Acid) is a benzoic acid derivative. A building block in medicine and organic synthesis.

Berberine

C20H18NO4+ (336.1236)

Berberine is an organic heteropentacyclic compound, an alkaloid antibiotic, a botanical anti-fungal agent and a berberine alkaloid. It has a role as an antilipemic drug, a hypoglycemic agent, an antioxidant, a potassium channel blocker, an antineoplastic agent, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor, an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor, an EC 1.21.3.3 (reticuline oxidase) inhibitor, an EC 2.1.1.116 [3-hydroxy-N-methyl-(S)-coclaurine 4-O-methyltransferase] inhibitor, an EC 3.1.1.4 (phospholipase A2) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 2.7.11.10 (IkappaB kinase) inhibitor, an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor, a geroprotector and a metabolite. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. Berberine is a quaternary ammonia compound found in many botanical products, including goldenseal, barberry and Oregon grape, which is used for its purported antioxidant and antimicrobial properties for a host of conditions, including obesity, diabetes, hyperlipidemia, heart failure, H. pylori infection and colonic adenoma prevention. Berberine has not been linked to serum aminotransferase elevations during therapy nor to instances of clinically apparent liver injury. Berberine is a natural product found in Berberis poiretii, Thalictrum delavayi, and other organisms with data available. Berberine is a quaternary ammonium salt of an isoquinoline alkaloid and active component of various Chinese herbs, with potential antineoplastic, radiosensitizing, anti-inflammatory, anti-lipidemic and antidiabetic activities. Although the mechanisms of action through which berberine exerts its effects are not yet fully elucidated, upon administration this agent appears to suppress the activation of various proteins and/or modulate the expression of a variety of genes involved in tumorigenesis and inflammation, including, but not limited to transcription factor nuclear factor-kappa B (NF-kB), myeloid cell leukemia 1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), B-cell lymphoma-extra large (Bcl-xl), cyclooxygenase (COX)-2, tumor necrosis factor (TNF), interleukin (IL)-6, IL-12, inducible nitric oxide synthase (iNOS), intercellular adhesion molecule-1 (ICAM-1), E-selectin, monocyte chemoattractant protein-1 (MCP-1), C-X-C motif chemokine 2 (CXCL2), cyclin D1, activator protein (AP-1), hypoxia-inducible factor 1 (HIF-1), signal transducer and activator of transcription 3 (STAT3), peroxisome proliferator-activated receptor (PPAR), arylamine N-acetyltransferase (NAT), and DNA topoisomerase I and II. The modulation of gene expression may induce cell cycle arrest and apoptosis, and inhibit cancer cell proliferation. In addition, berberine modulates lipid and glucose metabolism. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. See also: Goldenseal (part of); Berberis aristata stem (part of). Berberine is a quaternary ammonium salt that belongs to the protoberberine group of benzylisoquinoline alkaloids. Chemically, berberine is classified as an isoquinoline alkaloid. More specifically, berberine is a plant alkaloid derived from tyrosine through a complex 8 step biosynthetic process. Berberine is found in plants such as Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape) and Hydrastis canadensis (goldenseal). Two other known berberine-containing plants are Phellodendron chinense and Phellodendron amurense. Berberine is usually found in the roots, rhizomes, stems, and bark of Berberis plants. Due to berberines intense yellow color, plants that contain berberine were traditionally used to dye wool, leather, and wood. Under ultraviolet light, berberine shows a strong yellow fluorescence, making it useful in histology for staining heparin in mast cells. Berberine is a bioactive plant compound that has been frequently used in traditional medicine. Among the known physiological effects or bioactivities are: 1) Antimicrobial action against bacteria, fungi, protozoa, viruses, helminthes, and Chlamydia; 2) Antagonism against the effects of cholera and E coli heat-stable enterotoxin; 3) Inhibition of intestinal ion secretion and of smooth muscle contraction; 4) Reduction of inflammation and 5) Stimulation of bile secretion and bilirubin discharge (PMID:32335802). Berberine can inhibit bacterial growth in the gut, including Helicobacter pylori, protect the intestinal epithelial barrier from injury, and ameliorate liver injury. Currently, berberine is sold as an Over-the-Counter (OTC) drug for treating gastrointestinal infections in China (PMID:18442638). Berberine also inhibits the proliferation of various types of cancer cells and impedes invasion and metastasis (PMID:32335802). Recent evidence has also confirmed that berberine improves the efficacy and safety of both chemo and radiotherapies for cancer treatment (PMID:32335802). Berberine has also been shown to regulate glucose and lipid metabolism in vitro and in vivo (PMID:18442638). In fact, berberine is the main active component of an ancient Chinese herb Coptis chinensis French, which has been used to treat diabetes for thousands of years. As an anti-diabetic, berberine increases glucose uptake by muscle fibers independent of insulin levels. It triggers AMPK activation and increases glycolysis, leading to decreased insulin resistance and decreased oxygen respiration. The same mechanism leads to a reduction in gluconeogenesis in the liver. AMPK activation by berberine also leads to an antiatherosclerotic effect in mice. Berberines AMPK activation may also underlie berberines anti-obesity effects and favorable influence on weight loss (PMID:18442638). While its use as a medication is widely touted, it is important to remember that berberine inhibits CYP2D6 and CYP3A4 enzymes, both of which are involved in the metabolism of many endogenous substances and xenobiotics, including a number of prescription drugs. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. [HMDB] COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

hygrine

C8H15NO (141.1154)

A 1-(1-methylpyrrolidin-2-yl)acetone that has R configuration. It is a pyrrolidine alkaloid found in the coca plant, Erythroxylum coca.

(2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]propanoic acid

C26H31NO6 (453.2151)

(2s)-2-[(5e,7e)-dodeca-5,7-dien-3-yn-1-yl]-1-ethylpyrrolidine

C18H29N (259.23)

(1r,5r)-8-methyl-8-azabicyclo[3.2.1]octan-3-ol

C8H15NO (141.1154)

4-(2-hydroxypropan-2-yl)-2,3-dihydro-1-benzopyran-4-carboximidic acid

C13H17NO3 (235.1208)

(1s,2r,4s,5s,7r)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl 3-hydroxy-2-phenylpropanoate

C17H21NO4 (303.1471)

9-hexanoyl-6a-methyl-3-[(1e)-prop-1-en-1-yl]-9h,9ah-furo[2,3-h]isochromene-6,8-dione

C21H24O5 (356.1624)

(2s,3s,4as,5s,8ar)-2-methyl-5-[(1e,3e)-octa-1,3-dien-1-yl]-decahydroquinolin-3-ol

C18H31NO (277.2406)

(2s)-2-[(9ar)-3-hexanoyl-9a-methyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]propanoic acid

C24H27NO6 (425.1838)

(1r,2r,4r,5s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl 2-phenylprop-2-enoate

C17H19NO3 (285.1365)

(2s)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid

C27H31NO8 (497.205)

4-hydroxy-5-(1-hydroxyhexyl)oxolan-2-one

C10H18O4 (202.1205)

2-({2-[(2-amino-1-hydroxyethylidene)amino]-1-hydroxy-3-phenylpropylidene}amino)-n-(4-carbamimidamido-1-{[1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}butyl)-3-methylpentanimidic acid

C32H47N9O5 (637.37)

(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl acetate

C10H17NO2 (183.1259)

(2r)-2-[(1r,3ar,5ar,9as,11ar)-7-hydroxy-3a,6,6,9a,11a-pentamethyl-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-1-yl]-6-methyl-5-methylideneheptanoic acid

C31H50O3 (470.376)

(2s)-2-[(2-amino-1-hydroxyethylidene)amino]-n-[(1s)-1-{[(1s)-1-{[(1s)-4-carbamimidamido-1-{[(1s)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-c-hydroxycarbonimidoyl}-2-phenylethyl]butanediimidic acid

C39H51N11O7 (785.3973)

2-[3-hexanoyl-9a-methyl-2,9-dioxo-6-(prop-1-en-1-yl)furo[3,2-g]isoquinolin-7-yl]butanedioic acid

C25H27NO8 (469.1737)

(2r)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid

C27H31NO8 (497.205)

(1r,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-methylpropanoate

C12H21NO2 (211.1572)

2-[3-hexanoyl-9a-methyl-2,9-dioxo-6-(prop-1-en-1-yl)furo[3,2-g]isoquinolin-7-yl]propanoic acid

C24H27NO6 (425.1838)

(2s,3r,4r,6r)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),16,20(27),21(26),22,24-decaen-16-ol

C28H26N4O3 (466.2005)

6a-methyl-9-octanoyl-3-(prop-1-en-1-yl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione

C23H28O5 (384.1937)

24-α-ethylcholesterol

C29H50O (414.3861)

9-hexanoyl-6a-methyl-3-(prop-1-en-1-yl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione

C21H24O5 (356.1624)

(2s)-2-[(9ar)-9a-methyl-3-octanoyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]propanoic acid

C26H31NO6 (453.2151)

(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-ethyl-2-methylheptan-1-ol

C29H52O (416.4018)

(3e,5e,7e,9e,11e,13e,15e)-18-[(2r,4s)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-1-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15,17-octaen-2-one

C40H56O5 (616.4128)

(3ar,3br,9ar,9bs,11ar)-1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H50O (414.3861)

(2s,3s,4s,6r)-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),16,20(27),21(26),22,24-decaene-3,11,16-triol

C27H24N4O4 (468.1797)

(4r,5s)-4-hydroxy-5-[(1s)-1-hydroxyhexyl]oxolan-2-one

C10H18O4 (202.1205)

(1r)-4-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15,17-octaen-1-yn-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

C40H54O2 (566.4124)

(2r,4s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl 3-hydroxy-2-phenylpropanoate

C17H21NO4 (303.1471)

(2s,3s,4s,6r)-4-amino-3-methoxy-2-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),16,20(27),21(26),22,24-decaen-16-ol

C27H24N4O3 (452.1848)

(1r,5r,6r,7r,9s,11s,13s,14r)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1016)

(1r,5r,6s,7s,9s,11s,12s,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1016)

(1r,5r,6r,7r,9s,11s,12r,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1016)

24-α-methylcholesterol

C28H48O (400.3705)

8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2s)-2-methylbutanoate

C13H23NO2 (225.1729)

(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-1-ol

C27H48O (388.3705)

(1r,3as,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol

C27H48O (388.3705)

6a-methyl-9-octanoyl-3-[(1e)-prop-1-en-1-yl]-9h,9ah-furo[2,3-h]isochromene-6,8-dione

C23H28O5 (384.1937)

(6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-2,3-dimethylheptan-1-ol

C28H50O (402.3861)

2-[9a-methyl-3-octanoyl-2,9-dioxo-6-(prop-1-en-1-yl)furo[3,2-g]isoquinolin-7-yl]propanoic acid

C26H31NO6 (453.2151)

(2s)-3-methoxy-2-methyl-4-(methylamino)-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),16,20(27),21(26),22,24-decaen-16-ol

C28H26N4O3 (466.2005)

(2r)-2-[(9ar)-3-hexanoyl-9a-methyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]propanoic acid

C24H27NO6 (425.1838)

(11s,13s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1016)

(2r)-2-[(9ar)-3-hexanoyl-9a-methyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid

C25H27NO8 (469.1737)

(1s,5s)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl (2s)-3-hydroxy-2-phenylpropanoate

C17H23NO3 (289.1678)

2-methyl-5-(octa-1,3-dien-1-yl)-decahydroquinolin-3-yl 2-hydroxyacetate

C20H33NO3 (335.246)

(1r,5r,6r,7s,9r,11s,13s,14s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol

C11H17N3O8 (319.1016)

(2s)-2-[(9ar)-3-hexanoyl-9a-methyl-2,9-dioxo-6-[(1e)-prop-1-en-1-yl]furo[3,2-g]isoquinolin-7-yl]butanedioic acid

C25H27NO8 (469.1737)

2-[9a-methyl-3-octanoyl-2,9-dioxo-6-(prop-1-en-1-yl)furo[3,2-g]isoquinolin-7-yl]butanedioic acid

C27H31NO8 (497.205)

(2r,4s)-9-methyl-3-oxa-9-azatricyclo[3.3.1.0²,⁴]nonan-7-yl (2r)-3-hydroxy-2-phenylpropanoate

C17H21NO4 (303.1471)