NCBI Taxonomy: 703253

Quercitrin

C21H20O11 (448.1006)

Quercitrin, also known as quercimelin or quercitronic acid, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. A quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. Quercitrin exists in all living organisms, ranging from bacteria to humans. Quercitrin is found, on average, in the highest concentration within a few different foods, such as lingonberries, american cranberries, and olives and in a lower concentration in common beans, tea, and welsh onions. Quercitrin has also been detected, but not quantified, in several different foods, such as guava, bilberries, common pea, apricots, and spearmints. Quercitrin is a quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. It has a role as an antioxidant, an antileishmanial agent, an EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a monosaccharide derivative, a tetrahydroxyflavone, an alpha-L-rhamnoside and a quercetin O-glycoside. It is a conjugate acid of a quercitrin-7-olate. Quercitrin is a natural product found in Xylopia emarginata, Lotus ucrainicus, and other organisms with data available. Quercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose. It is a constituent of the dye quercitron. Quercitrin is found in many foods, some of which are garden tomato (variety), kiwi, italian sweet red pepper, and guava. A quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. [Raw Data] CBA03_Quercitrin_pos_10eV.txt [Raw Data] CBA03_Quercitrin_pos_20eV.txt [Raw Data] CBA03_Quercitrin_neg_50eV.txt [Raw Data] CBA03_Quercitrin_neg_30eV.txt [Raw Data] CBA03_Quercitrin_neg_10eV.txt [Raw Data] CBA03_Quercitrin_neg_40eV.txt [Raw Data] CBA03_Quercitrin_neg_20eV.txt [Raw Data] CBA03_Quercitrin_pos_50eV.txt [Raw Data] CBA03_Quercitrin_pos_30eV.txt [Raw Data] CBA03_Quercitrin_pos_40eV.txt Quercitrin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=522-12-3 (retrieved 2024-07-09) (CAS RN: 522-12-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2]. Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2]. Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2].

Catechin

C15H14O6 (290.079)

Catechin, also known as cyanidanol or catechuic acid, belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Catechin also belongs to the group of compounds known as flavan-3-ols (or simply flavanols), part of the chemical family of flavonoids. Catechin is one of the 4 catechin known diastereoisomers. Two of the isomers are in trans configuration and are called catechin and the other two are in cis configuration and are called epicatechin. The most common catechin isomer is the (+)-catechin. The other stereoisomer is (-)-catechin or ent-catechin. The most common epicatechin isomer is (-)-epicatechin. Catechin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Catechin is a bitter tasting compound and is associated with the bitterness in tea. Catechin is a plant secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Catechin is an antioxidant flavonoid, occurring especially in woody plants as both Catechin and (-)-Catechin (cis) forms. Outside of the human body, Catechin is found, on average, in the highest concentration in foods, such as blackcurrants (Ribes nigrum), evergreen blackberries (Rubus laciniatus), and blackberries (Rubus) and in a lower concentration in dills (Anethum graveolens), hot chocolates, and medlars (Mespilus germanica). Catechin has also been detected, but not quantified in, several different foods, such as rice (Oryza sativa), apple ciders, peanuts (Arachis hypogaea), fruit juices, and red teas. This could make catechin a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Catechin. (+)-catechin is the (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite. It has a role as an antioxidant and a plant metabolite. It is an enantiomer of a (-)-catechin. An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Cianidanol is a natural product found in Visnea mocanera, Salacia chinensis, and other organisms with data available. Catechin is a metabolite found in or produced by Saccharomyces cerevisiae. An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. See also: Gallocatechin (related); Crofelemer (monomer of); Bilberry (part of) ... View More ... Present in red wine. Widespread in plants; found in a variety of foodstuffs especies apricots, broad beans, cherries, chocolate, grapes, nectarines, red wine, rhubarb, strawberries and tea The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite. Catechin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=154-23-4 (retrieved 2024-07-12) (CAS RN: 154-23-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (±)-Catechin (rel-Cianidanol) is the racemate of Catechin. (±)-Catechin has two steric forms of (+)-Catechin and its enantiomer (-)-Catechin. (+)-Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Anticancer, anti-obesity, antidiabetic, anticardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects[1]. (±)-Catechin (rel-Cianidanol) is the racemate of Catechin. (±)-Catechin has two steric forms of (+)-Catechin and its enantiomer (-)-Catechin. (+)-Catechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Anticancer, anti-obesity, antidiabetic, anticardiovascular, anti-infectious, hepatoprotective, and neuroprotective effects[1]. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

Sucrose

C12H22O11 (342.1162)

Sucrose is a nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane (Saccharum officinarum), sugar beet (Beta vulgaris), and other plants and used extensively as a food and a sweetener. Sucrose is derived by crushing and extracting sugarcane with water or by extracting sugar beet with water, evaporating, and purifying with lime, carbon, and various liquids. Sucrose is also obtainable from sorghum. Sucrose occurs in low percentages in honey and maple syrup. Sucrose is used as a sweetener in foods and soft drinks, in the manufacture of syrups, in invert sugar, confectionery, preserves and jams, demulcent, pharmaceutical products, and caramel. Sucrose is also a chemical intermediate for detergents, emulsifying agents, and other sucrose derivatives. Sucrose is widespread in the seeds, leaves, fruits, flowers, and roots of plants, where it functions as an energy store for metabolism and as a carbon source for biosynthesis. The annual world production of sucrose is in excess of 90 million tons mainly from the juice of sugar cane (20\\\%) and sugar beet (17\\\%). In addition to its use as a sweetener, sucrose is used in food products as a preservative, antioxidant, moisture control agent, stabilizer, and thickening agent. BioTransformer predicts that sucrose is a product of 6-O-sinapoyl sucrose metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme (PMID: 30612223). Sucrose appears as white odorless crystalline or powdery solid. Denser than water. Sucrose is a glycosyl glycoside formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose. It has a role as an osmolyte, a sweetening agent, a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. A nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane, sugar beet (beta vulgaris), and other plants and used extensively as a food and a sweetener. Sucrose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Sucrose is a natural product found in Haplophyllum ramosissimum, Cyperus esculentus, and other organisms with data available. Sucrose is a metabolite found in or produced by Saccharomyces cerevisiae. A nonreducing disaccharide composed of GLUCOSE and FRUCTOSE linked via their anomeric carbons. It is obtained commercially from SUGARCANE, sugar beet (BETA VULGARIS), and other plants and used extensively as a food and a sweetener. See also: Anise; ferrous disulfide; sucrose (component of); Phosphoric acid; sucrose (component of); Sucrose caramel (related) ... View More ... In chemistry, sugar loosely refers to a number of carbohydrates, such as monosaccharides, disaccharides, or oligosaccharides. In food, sugar refers to a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose characterized by a sweet flavor. Other sugars are used in industrial food preparation, but are usually known by more specific names - glucose, fructose or fruit sugar, high fructose corn syrup, etc. Sugars is found in many foods, some of which are ucuhuba, butternut squash, common walnut, and miso. A glycosyl glycoside formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose. Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula C 12H 22O 11. For human consumption, sucrose is extracted and refined from either sugarcane or sugar beet. Sugar mills – typically located in tropical regions near where sugarcane is grown – crush the cane and produce raw sugar which is shipped to other factories for refining into pure sucrose. Sugar beet factories are located in temperate climates where the beet is grown, and process the beets directly into refined sugar. The sugar-refining process involves washing the raw sugar crystals before dissolving them into a sugar syrup which is filtered and then passed over carbon to remove any residual colour. The sugar syrup is then concentrated by boiling under a vacuum and crystallized as the final purification process to produce crystals of pure sucrose that are clear, odorless, and sweet. Sugar is often an added ingredient in food production and recipes. About 185 million tonnes of sugar were produced worldwide in 2017.[6] Sucrose is particularly dangerous as a risk factor for tooth decay because Streptococcus mutans bacteria convert it into a sticky, extracellular, dextran-based polysaccharide that allows them to cohere, forming plaque. Sucrose is the only sugar that bacteria can use to form this sticky polysaccharide.[7] Sucrose. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=8030-20-4 (retrieved 2024-06-29) (CAS RN: 57-50-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Gallic acid

C7H6O5 (170.0215)

Gallic acid is an odorless white solid. Sinks in water. (USCG, 1999) Gallic acid is a trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. It has a role as an astringent, a cyclooxygenase 2 inhibitor, a plant metabolite, an antioxidant, an antineoplastic agent, a human xenobiotic metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an apoptosis inducer and a geroprotector. It is a conjugate acid of a gallate. Gallic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Gallic Acid is a natural product found in Visnea mocanera, Ardisia paniculata, and other organisms with data available. Gallic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A colorless or slightly yellow crystalline compound obtained from nutgalls. It is used in photography, pharmaceuticals, and as an analytical reagent. See also: Gallic acid monohydrate (active moiety of); Paeonia lactiflora root (part of); Galium aparine whole (part of) ... View More ... Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3CO2H. Gallic acid is widely distributed in plants and is found both free and as part of tannins. It is commonly used in the pharmaceutical industry. Gallic acid can also be used to synthesize the hallucinogenic alkaloid mescaline, also known as 3,4,5-trimethoxyphenethylamine. Salts and esters of gallic acid are termed gallates. Gallic acid has been found to be s metabolite of Aspergillus (PMID:24031294). A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. Present in red wine. Japan approved food antioxidant additive Gallic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=149-91-7 (retrieved 2024-07-01) (CAS RN: 149-91-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2]. Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2].

Protocatechuic acid

C7H6O4 (154.0266)

Protocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate. Protocatechuic acid is a drug. In the analogous hardening of the cockroach ootheca, the phenolic substance concerned is protocatechuic acid. Protocatechuic acid is a mild, balsamic, and phenolic tasting compound. Outside of the human body, protocatechuic acid is found, on average, in the highest concentration in a few different foods, such as garden onions, cocoa powders, and star anises and in a lower concentration in lentils, liquors, and red raspberries. Protocatechuic acid has also been detected, but not quantified in several different foods, such as cloud ear fungus, american pokeweeds, common mushrooms, fruits, and feijoa. This could make protocatechuic acid a potential biomarker for the consumption of these foods. It is also found in Allium cepa (17,540 ppm). It is a major metabolite of antioxidant polyphenols found in green tea. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells. In vitro testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection in vivo was measured by chemical markers and histological assessment. 3,4-dihydroxybenzoic acid, also known as protocatechuic acid or 4-carboxy-1,2-dihydroxybenzene, belongs to hydroxybenzoic acid derivatives class of compounds. Those are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxybenzoic acid can be synthesized from benzoic acid. 3,4-dihydroxybenzoic acid is also a parent compound for other transformation products, including but not limited to, methyl 3,4-dihydroxybenzoate, ethyl 3,4-dihydroxybenzoate, and 1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose. 3,4-dihydroxybenzoic acid is a mild, balsamic, and phenolic tasting compound and can be found in a number of food items such as white mustard, grape wine, abalone, and asian pear, which makes 3,4-dihydroxybenzoic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxybenzoic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and testes tissues. 3,4-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies . 3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as a human xenobiotic metabolite, a plant metabolite, an antineoplastic agent, an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor and an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor. It is a member of catechols and a dihydroxybenzoic acid. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate. 3,4-Dihydroxybenzoic acid is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. Protocatechuic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Vaccinium myrtillus Leaf (part of); Menyanthes trifoliata leaf (part of) ... View More ... A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. Protocatechuic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-50-3 (retrieved 2024-06-29) (CAS RN: 99-50-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

Ursolic acid

C30H48O3 (456.3603)

Ursolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040, 17516235, 17213663). Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane. Ursolic acid is a natural product found in Gladiolus italicus, Freziera, and other organisms with data available. Ursolic Acid is a pentacyclic triterpenoid found in various fruits, vegetables and medicinal herbs, with a variety of potential pharmacologic activities including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities. Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms. This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities. See also: Holy basil leaf (part of); Jujube fruit (part of); Lagerstroemia speciosa leaf (part of). D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent Found in wax of apples, pears and other fruits. V. widely distributed in plants D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C26170 - Protective Agent > C275 - Antioxidant D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

Quercetin

C15H10O7 (302.0427)

Quercetin appears as yellow needles or yellow powder. Converts to anhydrous form at 203-207 °F. Alcoholic solutions taste very bitter. (NTP, 1992) Quercetin is a pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. It has a role as an antibacterial agent, an antioxidant, a protein kinase inhibitor, an antineoplastic agent, an EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor, a plant metabolite, a phytoestrogen, a radical scavenger, a chelator, an Aurora kinase inhibitor and a geroprotector. It is a pentahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a quercetin-7-olate. Quercetin is a flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. Quercetin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Quercetin is a flavonoid found in many foods and herbs and is a regular component of a normal diet. Extracts of quercetin have been used to treat or prevent diverse conditions including cardiovascular disease, hypercholesterolemia, rheumatic diseases, infections and cancer but have not been shown to be effective in clinical trials for any medical condition. Quercetin as a nutritional supplement is well tolerated and has not been linked to serum enzyme elevations or to episodes of clinically apparent liver injury. Quercetin is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Quercetin is a polyphenolic flavonoid with potential chemopreventive activity. Quercetin, ubiquitous in plant food sources and a major bioflavonoid in the human diet, may produce antiproliferative effects resulting from the modulation of either EGFR or estrogen-receptor mediated signal transduction pathways. Although the mechanism of action of action is not fully known, the following effects have been described with this agent in vitro: decreased expression of mutant p53 protein and p21-ras oncogene, induction of cell cycle arrest at the G1 phase and inhibition of heat shock protein synthesis. This compound also demonstrates synergy and reversal of the multidrug resistance phenotype, when combined with chemotherapeutic drugs, in vitro. Quercetin also produces anti-inflammatory and anti-allergy effects mediated through the inhibition of the lipoxygenase and cyclooxygenase pathways, thereby preventing the production of pro-inflammatory mediators. Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercitin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adju... Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercetin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions (PMID:17015250). Quercetin is isolated from many plants, especially fruits, such as Helichrysum, Euphorbia and Karwinskia spp. Present in the Solanaceae, Rhamnaceae, Passifloraceae and many other families. For example detected in almost all studied Umbelliferae. Nutriceutical with antiinflammatory props. and a positive influence on the blood lipid profile. Found in a wide variety of foods especially apples, bee pollen, blackcurrants, capers, cocoa, cranberries, dock leaves, elderberries, fennel, lovage, red onions, ancho peppers, dill weed and tarragon. A pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4014; ORIGINAL_PRECURSOR_SCAN_NO 4012 INTERNAL_ID 298; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4019; ORIGINAL_PRECURSOR_SCAN_NO 4018 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4017; ORIGINAL_PRECURSOR_SCAN_NO 4016 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4096; ORIGINAL_PRECURSOR_SCAN_NO 4094 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4024; ORIGINAL_PRECURSOR_SCAN_NO 4023 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB109_Quercetin_pos_30eV_CB000041.txt IPB_RECORD: 1761; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_pos_10eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_20eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_40eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_50eV_CB000041.txt IPB_RECORD: 161; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_neg_40eV_000027.txt [Raw Data] CB109_Quercetin_neg_50eV_000027.txt [Raw Data] CB109_Quercetin_neg_20eV_000027.txt [Raw Data] CB109_Quercetin_neg_30eV_000027.txt [Raw Data] CB109_Quercetin_neg_10eV_000027.txt CONFIDENCE standard compound; INTERNAL_ID 124 CONFIDENCE standard compound; ML_ID 54 Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

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].

Myristic acid

C14H28O2 (228.2089)

Tetradecanoic acid is an oily white crystalline solid. (NTP, 1992) Tetradecanoic acid is a straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetradecanoate. Myristic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Myristic acid is a natural product found in Gladiolus italicus, Staphisagria macrosperma, and other organisms with data available. Myristic Acid is a saturated long-chain fatty acid with a 14-carbon backbone. Myristic acid is found naturally in palm oil, coconut oil and butter fat. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). Myristic acid is also commonly added to a penultimate nitrogen terminus glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. this is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell.(wikipedia). myristic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed) See also: Cod Liver Oil (part of); Saw Palmetto (part of). Myristic acid, also known as tetradecanoic acid or C14:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Myristic acid (its ester is called myristate) is a saturated fatty acid that has 14 carbons; as such, it is a very hydrophobic molecule that is practically insoluble in water. It exists as an oily white crystalline solid. Myristic acid is found in all living organisms ranging from bacteria to plants to animals, and is found in most animal and vegetable fats, particularly butterfat, as well as coconut, palm, and nutmeg oils. Industrially, myristic acid is used to synthesize a variety of flavour compounds and as an ingredient in soaps and cosmetics (Dorland, 28th ed). Within eukaryotic cells, myristic acid is also commonly conjugated to a penultimate N-terminal glycine residue in receptor-associated kinases to confer membrane localization of these enzymes (a post-translational modification called myristoylation via the enzyme N-myristoyltransferase). Myristic acid has a high enough hydrophobicity to allow the myristoylated protein to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of eukaryotic cells. Also, this fatty acid is known because it accumulates as fat in the body; however, its consumption also impacts positively on cardiovascular health (see, for example, PMID: 15936650). Myristic acid is named after the scientific name for nutmeg, Myristica fragrans, from which it was first isolated in 1841 by Lyon Playfair. Myristic acid, also known as 14 or N-tetradecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, myristic acid is considered to be a fatty acid lipid molecule. Myristic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Myristic acid can be found in a number of food items such as strawberry, barley, nutmeg, and soy bean, which makes myristic acid a potential biomarker for the consumption of these food products. Myristic acid can be found primarily in most biofluids, including cerebrospinal fluid (CSF), blood, saliva, and feces, as well as throughout most human tissues. Myristic acid exists in all living species, ranging from bacteria to humans. In humans, myristic acid is involved in the fatty acid biosynthesis. Moreover, myristic acid is found to be associated with schizophrenia. Myristic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Myristic acid (IUPAC systematic name: 1-tetradecanoic acid) is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. Its salts and esters are commonly referred to as myristates. It is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair . A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. Nutmeg butter has 75\\\% trimyristin, the triglyceride of myristic acid and a source from which it can be synthesised.[13] Besides nutmeg, myristic acid is found in palm kernel oil, coconut oil, butterfat, 8–14\\\% of bovine milk, and 8.6\\\% of breast milk as well as being a minor component of many other animal fats.[9] It is found in spermaceti, the crystallized fraction of oil from the sperm whale. It is also found in the rhizomes of the Iris, including Orris root.[14][15] Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.

Palmitic acid

C16H32O2 (256.2402)

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

Nervonic acid

C24H46O2 (366.3498)

Nervonic acid is a long chain unsaturated fatty acid that is enriched in sphingomyelin. It consists of choline, sphingosine, phosphoric acid, and fatty acid. Nervonic acid may enhance the brain functions and prevent demyelination (Chemical Land21). Research shows that there is negative relationship between nervonic acid and obesity-related risk factors (PMID:16394593). Demyelination in adrenoleukodystrophy (ALD) is associated with an accumulation of very long chain saturated fatty acids stemming from a genetic defect in the peroxisomal beta oxidation system responsible for the chain shortening of these fatty acids. Sphingolipids from post mortem ALD brain have decreased levels of nervonic acid, 24:1(n-9), and increased levels of stearic acid, 18:0. (PMID:8072429). (15Z)-tetracosenoic acid is a tetracosenoic acid having a cis-double bond at position 15. It is a conjugate acid of a (15Z)-tetracosenoate. Nervonic acid is a natural product found in Tropaeolum speciosum, Calophyllum inophyllum, and other organisms with data available. Nervonic Acid is a monounsaturated fatty acid with a 24-carbon backbone and the sole double bond originating from the 9th carbon from the methyl end, with this bond in the cis- configuration. See also: Borage Seed Oil (part of). A tetracosenoic acid having a cis-double bond at position 15. Present in fish and rape seed oils Nervonic acid is a monounsaturated fatty acid important in the biosynthesis of myelin. Nervonic acid is a monounsaturated fatty acid important in the biosynthesis of myelin.

Stigmasterol

C29H48O (412.3705)

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

Taraxerol

C30H50O (426.3861)

Taraxerol is a pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15. It has a role as a metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. Taraxerol is a natural product found in Diospyros morrisiana, Liatris acidota, and other organisms with data available. See also: Myrica cerifera root bark (part of). Constituent of Taraxacum officinale (dandelion). Taraxerol is found in many foods, some of which are kiwi, scarlet bean, prairie turnip, and grapefruit/pummelo hybrid. Taraxerol is found in alcoholic beverages. Taraxerol is a constituent of Taraxacum officinale (dandelion)

Lupeol

C30H50O (426.3861)

Lupeol is a pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. It has a role as an anti-inflammatory drug and a plant metabolite. It is a secondary alcohol and a pentacyclic triterpenoid. It derives from a hydride of a lupane. Lupeol has been investigated for the treatment of Acne. Lupeol is a natural product found in Ficus auriculata, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

Friedelin

C30H50O (426.3861)

Friedelin is a pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. It has a role as an anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and a plant metabolite. It is a pentacyclic triterpenoid and a cyclic terpene ketone. Friedelin is a natural product found in Diospyros eriantha, Salacia chinensis, and other organisms with data available. A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. Friedelin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Friedelin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Friedelin can be found in a number of food items such as pomegranate, sugar apple, apple, and mammee apple, which makes friedelin a potential biomarker for the consumption of these food products. Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant .

Betulin

C30H50O2 (442.3811)

Betulin is found in black elderberry. Betulin is a constituent of Corylus avellana (filbert) and Vicia faba. Betulin (lup-20(29)-ene-3 ,28-diol) is an abundant naturally occurring triterpene. It is commonly isolated from the bark of birch trees and forms up to 30\\\\\% of the dry weight of the extractive. The purpose of the compound in the bark is not known. It can be converted to betulinic acid (the alcohol group replaced by a carboxylic acid group), which is biologically more active than betulin itself. Chemically, betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28 Betulin is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents. It has a role as a metabolite, an antiviral agent, an analgesic, an anti-inflammatory agent and an antineoplastic agent. It is a pentacyclic triterpenoid and a diol. It derives from a hydride of a lupane. Betulin is a natural product found in Diospyros morrisiana, Euonymus carnosus, and other organisms with data available. A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents. Constituent of Corylus avellana (filbert) and Vicia faba Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.

Betulinic acid

C30H48O3 (456.3603)

Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane. Betulinic Acid has been used in trials studying the treatment of Dysplastic Nevus Syndrome. Betulinic acid is a natural product found in Ficus auriculata, Gladiolus italicus, and other organisms with data available. Betulinic Acid is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Although originally thought to exhibit specific cytotoxicity against melanoma cells, this agent has been found to be cytotoxic against non-melanoma tumor cell types including neuroectodermal and brain tumor cells. A lupane-type triterpene derivative of betulin which was originally isolated from BETULA or birch tree. It has anti-inflammatory, anti-HIV and antineoplastic activities. See also: Jujube fruit (part of); Paeonia lactiflora root (part of). Betulinic acid is found in abiyuch. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53 A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. C308 - Immunotherapeutic Agent > C2139 - Immunostimulant Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Epibetulinic acid exhibits potent inhibitory effects on NO and prostaglandin E2 (PGE2) production in mouse macrophages (RAW 264.7) stimulated with bacterial endotoxin with IC50s of 0.7 and 0.6 μM, respectively. Anti-inflammatory activity[1].

Oleanolic acid

C30H48O3 (456.3603)

Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619, 15522132, 15994040). Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane. Oleanolic acid is a natural product found in Ophiopogon japonicus, Freziera, and other organisms with data available. A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. See also: Holy basil leaf (part of); Jujube fruit (part of); Paeonia lactiflora root (part of) ... View More ... Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. [Raw Data] CBA90_Oleanolic-acid_neg_50eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_20eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_10eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_30eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_40eV.txt Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

Squalene

C30H50 (410.3912)

Squalene is an unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds found in human sebum (5\\\\%), fish liver oils, yeast lipids, and many vegetable oils (e.g. palm oil, cottonseed oil, rapeseed oil). Squalene is a volatile component of the scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey) (Hawleys Condensed Chemical Reference). Squalene is a component of adult human sebum that is principally responsible for fixing fingerprints (ChemNetBase). It is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanical sources as well, including rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. Squalene is a biochemical precursor to the whole family of steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. Squalene is a low-density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the sharks liver, is lighter than water with a specific gravity of 0.855 (Wikipedia) Squalene is used as a bactericide. It is also an intermediate in the manufacture of pharmaceuticals, rubber chemicals, and colouring materials (Physical Constants of Chemical Substances). Trans-squalene is a clear, slightly yellow liquid with a faint odor. Density 0.858 g / cm3. Squalene is a triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. It has a role as a human metabolite, a plant metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. Squalene is originally obtained from shark liver oil. It is a natural 30-carbon isoprenoid compound and intermediate metabolite in the synthesis of cholesterol. It is not susceptible to lipid peroxidation and provides skin protection. It is ubiquitously distributed in human tissues where it is transported in serum generally in association with very low density lipoproteins. Squalene is investigated as an adjunctive cancer therapy. Squalene is a natural product found in Ficus septica, Garcinia multiflora, and other organisms with data available. squalene is a metabolite found in or produced by Saccharomyces cerevisiae. A natural 30-carbon triterpene. See also: Olive Oil (part of); Shark Liver Oil (part of). A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].

6-Deoxyjacareubin

C18H14O5 (310.0841)

6-Deoxyjacareubin is a member of pyranoxanthones. 6-Deoxyjacareubin is a natural product found in Mourera fluviatilis, Hypericum brasiliense, and other organisms with data available.

Amyrin

C30H50O (426.3861)

Beta-amyrin is a pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. It has a role as a plant metabolite and an Aspergillus metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an oleanane. beta-Amyrin is a natural product found in Ficus pertusa, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

Mesuaxanthone A

C14H10O5 (258.0528)

Mesuaxanthone A is a member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at bpositions 1 and 5 and a methoxy group at position 3. It has a role as a plant metabolite. It is a member of xanthones, a polyphenol and an aromatic ether. Mesuaxanthone A is a natural product found in Calophyllum inophyllum, Hypericum chinense, and other organisms with data available. A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at bpositions 1 and 5 and a methoxy group at position 3.

Erucic acid

C22H42O2 (338.3185)

Before genetic engineering, plant breeders were aiming to produce a less-bitter-tasting multi-purpose oil from rapeseed that would appeal to a larger market by making it more palatable for cattle and other livestock. While it was possible to breed out much of the pungent-tasting glucosinolates, one of the dominant erucic acid genes would get stripped out of the genome as well, greatly reducing its valuable erucic acid content. Studies on rats show lipodosis problems when fed high quantities of erucic acid, however, so this did not hinder saleability. Later trials showed that rats had the same problems with other vegetable fatty acids, because rats are poor at metabolising some fats. The plant breeding industry later changed "low erucic acid" to be its unique selling proposition over that of its competitors.; Erucic acid is a monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Its ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:ln9) and erucic acid (22:1n9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid.; Erucic acid is a monounsaturated omega-9 fatty acid, denoted 22:1 ?-9. It is prevalent in rapeseed, wallflower seed, and mustard seed, making up 40-50\\% of their oils. Erucic acid is also known as cis-13-docosenoic acid and the trans isomer is known as brassidic acid.; The name erucic means: of or pertaining to eruca; which is a genus of flowering plants in the family Brassicaceae. It is also the Latin for coleworth, which today is better known as kale. Erucic acid is produced naturally (together with other fatty acids) across a great range of green plants, but especially so in members of the brassica family. It is highest in some of the rapeseed varieties of brassicas, kale and mustard being some of the highest, followed by Brussels spouts and broccoli. For industrial purposes, a High-Erucic Acid Rapeseed (HEAR) has been developed. These cultivars can yield 40\\% to 60\\% of the total oil recovered as erucic acid. Erucic acid is a 22-carbon, monounsaturated omega-9 fatty acid found mainly in the Brassica family of plants such as canola, rapeseed, wallflower seed, mustard seed as well as Brussels spouts and broccoli. Some Brassica cultivars can have up to 40 to 50 percent of their oil recovered as erucic acid. Erucic acid is also known as cis-13-docosenoic acid. The trans isomer is known as brassidic acid. Erucic acid occurs in nature only along with bitter-tasting compounds. Erucic acid has many of the same uses as mineral oils but with the advantage that it is more readily bio-degradable. Its high tolerance to temperature makes it suitable for transmission oil. Erucic acid’s ability to polymerize and dry means it can be - and is - used as a binder for oil paints. Increased levels of eicosenoic acid (20:Ln9) and erucic acid (22:1N9) have been found in the red blood cell membranes of autistic subjects with developmental regression (PMID: 16581239 ). Erucic acid is broken down long-chain acyl-coenzyme A (CoA) dehydrogenase, which is produced in the liver. This enzyme breaks this long chain fatty acid into shorter-chain fatty acids. Human infants have relatively low amounts of this enzyme and because of this, babies should not be given foods high in erucic acid. Food-grade rapeseed oil (also known as canola oil) is regulated to a maximum of 2\\% erucic acid by weight in the US and 5\\% in the EU, with special regulations for infant food. Canola was bred from rapeseed cultivars of B. napus and B. rapa at the University of Manitoba, Canada. Canola oil is derived from a variety of rapeseed that is low in erucic acid. Erucic acid is a docosenoic acid having a cis- double bond at C-13. It is found particularly in brassicas - it is a major component of mustard and rapeseed oils and is produced by broccoli, Brussels sprouts, kale, and wallflowers. It is a conjugate acid of an erucate. Erucic acid is a natural product found in Dipteryx lacunifera, Myrtus communis, and other organisms with data available. Erucic Acid is a monounsaturated very long-chain fatty acid with a 22-carbon backbone and a single double bond originating from the 9th position from the methyl end, with the double bond in the cis- configuration. See also: Cod Liver Oil (part of). A docosenoic acid having a cis- double bond at C-13. It is found particularly in brassicas - it is a major component of mustard and rapeseed oils and is produced by broccoli, Brussels sprouts, kale, and wallflowers.

Stearic acid

C18H36O2 (284.2715)

Stearic acid, also known as stearate or N-octadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, stearic acid is considered to be a fatty acid lipid molecule. Stearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Stearic acid can be synthesized from octadecane. Stearic acid is also a parent compound for other transformation products, including but not limited to, 3-oxooctadecanoic acid, (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid, and 16-methyloctadecanoic acid. Stearic acid can be found in a number of food items such as green bell pepper, common oregano, ucuhuba, and babassu palm, which makes stearic acid a potential biomarker for the consumption of these food products. Stearic acid can be found primarily in most biofluids, including urine, feces, cerebrospinal fluid (CSF), and sweat, as well as throughout most human tissues. Stearic acid exists in all living species, ranging from bacteria to humans. In humans, stearic acid is involved in the plasmalogen synthesis. Stearic acid is also involved in mitochondrial beta-oxidation of long chain saturated fatty acids, which is a metabolic disorder. Moreover, stearic acid is found to be associated with schizophrenia. Stearic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin . Stearic acid, also known as octadecanoic acid or C18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‚Äòtallow‚Äô or ‚Äòhard fat‚Äô. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Palmitoleic acid

C16H30O2 (254.2246)

Cis-9-palmitoleic acid, also known as palmitoleate or (Z)-9-hexadecenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, cis-9-palmitoleic acid is considered to be a fatty acid lipid molecule. Cis-9-palmitoleic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-9-palmitoleic acid can be found in a number of food items such as mixed nuts, carrot, hedge mustard, and chanterelle, which makes cis-9-palmitoleic acid a potential biomarker for the consumption of these food products. Cis-9-palmitoleic acid can be found primarily in most biofluids, including urine, blood, saliva, and feces, as well as in human adipose tissue, prostate and skeletal muscle tissues. Cis-9-palmitoleic acid exists in all living species, ranging from bacteria to humans. Moreover, cis-9-palmitoleic acid is found to be associated with isovaleric acidemia. Palmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. Present in all tissues, it is generally found in higher concentrations in the liver. Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40\\\\\% respectively. Palmitoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Palmitoleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=373-49-9 (retrieved 2024-07-15) (CAS RN: 373-49-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats. Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.

Oleic acid

C18H34O2 (282.2559)

Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70\\\\%). Oleic acid triglycerides also make up 59–75\\\\% of pecan oil, 61\\\\% of canola oil, 36–67\\\\% of peanut oil, 60\\\\% of macadamia oil, 20–80\\\\% of sunflower oil, 15–20\\\\% of grape seed oil, sea buckthorn oil, 40\\\\% of sesame oil, and 14\\\\% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80\\\\%) and canola oil (70\\\\%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Major constituent of plant oils e.g. olive oil (ca. 80\\\\%), almond oil (ca. 80\\\\%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods CONFIDENCE standard compound; INTERNAL_ID 290 COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

Rhamnetin

C16H12O7 (316.0583)

Acquisition and generation of the data is financially supported in part by CREST/JST. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1]. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1]. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1].

Lignoceric acid (C24)

C24H48O2 (368.3654)

Lignoceric acid, also known as N-tetracosanoic acid or tetraeicosanoate, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, lignoceric acid is considered to be a fatty acid lipid molecule. Lignoceric acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Lignoceric acid can be found in a number of food items such as hazelnut, cheese, rye bread, and cetacea (dolphin, porpoise, whale), which makes lignoceric acid a potential biomarker for the consumption of these food products. Lignoceric acid can be found primarily in blood and feces, as well as in human fibroblasts tissue. Lignoceric acid exists in all eukaryotes, ranging from yeast to humans. In humans, lignoceric acid is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Lignoceric acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. Lignoceric acid, or tetracosanoic acid, is the saturated fatty acid with formula C23H47COOH. It is found in wood tar, various cerebrosides, and in small amounts in most natural fats. The fatty acids of peanut oil contain small amounts of lignoceric acid (1.1\\\\% – 2.2\\\\%). This fatty acid is also a byproduct of lignin production . Tetracosanoic acid is a C24 straight-chain saturated fatty acid. It has a role as a volatile oil component, a plant metabolite, a human metabolite and a Daphnia tenebrosa metabolite. It is a very long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetracosanoate. Tetracosanoic acid, also known as N-tetracosanoate or lignoceric acid, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tetracosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tetracosanoic acid is a potentially toxic compound. Acquisition and generation of the data is financially supported in part by CREST/JST. Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid, which is synthesized in the developing brain. Lignoceric acid is also a by-product of lignin production. Lignoceric acid can be used for Zellweger cerebro‐hepato‐renal syndrome and adrenoleukodystrophy research[1][2]. Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid, which is synthesized in the developing brain. Lignoceric acid is also a by-product of lignin production. Lignoceric acid can be used for Zellweger cerebro‐hepato‐renal syndrome and adrenoleukodystrophy research[1][2].

3,4-Dihydroxybenzaldehyde

C7H6O3 (138.0317)

Protocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus . 3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia). D006401 - Hematologic Agents > D000925 - Anticoagulants Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

11Z-Eicosenoic acid（20:1）

C20H38O2 (310.2872)

11Z-Eicosenoic acid, also known as gondoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. 11Z-Eicosenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). More specifically, 11Z-Eicosenoic acid is a monounsaturated omega-9 fatty acid found in a variety of nuts and plant oils. It is not produced by humans and comes from the diet. It has been found in the red blood cell membrane with increased concentrations in children with regressive autism (PMID: 16581239 ). (11Z)-icos-11-enoic acid is an icosenoic acid having a cis- double bond at position 11. It has a role as a plant metabolite and a human metabolite. It is a conjugate acid of a gondoate. cis-11-Eicosenoic acid is a natural product found in Delphinium fissum, Calophyllum inophyllum, and other organisms with data available. Gondoic Acid is a monounsaturated long-chain fatty acid with a 20-carbon backbone and the sole double bond originating from the 9th position from the methyl end, with the bond in the cis- configuration. See also: Cod Liver Oil (part of). Constituent of rape oil and fish oils as glycerideand is also in other plant oils, e.g. false flax (Camelina sativa), and swede (Brassica napobrassica) cis-11-Eicosenoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=5561-99-9 (retrieved 2024-07-15) (CAS RN: 5561-99-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Gondoic acid (cis-11-Eicosenoic acid), a monounsaturated long-chain fatty acid, is contained in a variety of plant oils and nuts[1]. Gondoic acid (cis-11-Eicosenoic acid), a monounsaturated long-chain fatty acid, is contained in a variety of plant oils and nuts[1].

Amentoflavone

C30H18O10 (538.09)

Amentoflavone is a biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-3 of the hydroxyphenyl ring and C-8 of the chromene ring. A natural product found particularly in Ginkgo biloba and Hypericum perforatum. It has a role as a cathepsin B inhibitor, an antiviral agent, an angiogenesis inhibitor, a P450 inhibitor and a plant metabolite. It is a biflavonoid, a hydroxyflavone and a ring assembly. Amentoflavone is a natural product found in Podocarpus elongatus, Austrocedrus chilensis, and other organisms with data available. A biflavonoid that is obtained by oxidative coupling of two molecules of apigenin resulting in a bond between positions C-3 of the hydroxyphenyl ring and C-8 of the chromene ring. A natural product found particularly in Ginkgo biloba and Hypericum perforatum. D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065688 - Cytochrome P-450 CYP2C9 Inhibitors D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065692 - Cytochrome P-450 CYP3A Inhibitors Amentoflavone is found in fruits. Amentoflavone is obtained from Viburnum prunifolium (black haw Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4].

delta-Tocotrienol

C27H40O2 (396.3028)

delta-Tocotrienol, also known as 8-methyltocotrienol, belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. They differ from tocopherols that contain a saturated trimethyltridecyl chain. Thus, delta-tocotrienol is considered to be a quinone lipid molecule. delta-Tocotrienol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. delta-Tocotrienol is found in American cranberry and palm oil. It is a nutriceutical with anticancer properties and a positive influence on the blood lipid profile. Constituent of palm oil. Nutriceutical with anticancer props. and a positive influence on the blood lipid profile. d-Tocotrienol is found in many foods, some of which are fennel, caraway, coconut, and lichee. Acquisition and generation of the data is financially supported in part by CREST/JST.

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].

Behenic acid

C22H44O2 (340.3341)

Behenic acid, also known as docosanoate or 1-docosanoic acid, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, behenic acid is considered to be a fatty acid lipid molecule. Behenic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Behenic acid can be found in a number of food items such as rice, opium poppy, pepper (c. frutescens), and gram bean, which makes behenic acid a potential biomarker for the consumption of these food products. Behenic acid can be found primarily in blood, feces, and urine. Behenic acid (also docosanoic acid) is a carboxylic acid, the saturated fatty acid with formula C21H43COOH. In appearance, it consists of white to cream color crystals or powder with a melting point of 80 °C and boiling point of 306 °C . Behenic acid, also docosanoic acid, is a normal carboxylic acid, a fatty acid with formula C21H43COOH. It is an important constituent of the behen oil extracted from the seeds of the Ben-oil tree, and it is so named from the Persian month Bahman when the roots of this tree were harvested. Behenic acid has been identified in the human placenta (PMID:32033212). Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans.

2,6-Dimethoxy-1,4-benzoquinone

C8H8O4 (168.0423)

2,6-Dimethoxy-1,4-benzoquinone is a natural product found in Diospyros eriantha, Iris milesii, and other organisms with data available. 2,6-Dimethoxyquinone is a methoxy-substituted benzoquinone and bioactive compound found in fermented wheat germ extracts, with potential antineoplastic and immune-enhancing activity. 2,6-Dimethoxyquinone (2,6-DMBQ) inhibits anaerobic glycolysis thereby preventing cellular metabolism and inducing apoptosis. As cancer cells use the anaerobic glycolysis pathway to metabolize glucose and cancer cells proliferate at an increased rate as compared to normal, healthy cells, this agent is specifically cytotoxic towards cancer cells. In addition, 2,6-DMBQ exerts immune-enhancing effects by increasing natural killer (NK) cell and T-cell activity against cancer cells. See also: Acai fruit pulp (part of). 2,6-Dimethoxy-1,4-benzoquinone is found in common wheat. 2,6-Dimethoxy-1,4-benzoquinone is a constituent of bark of Phyllostachys heterocycla var. pubescens (moso bamboo) Constituent of bark of Phyllostachys heterocycla variety pubescens (moso bamboo). 2,6-Dimethoxy-1,4-benzoquinone is found in green vegetables and common wheat. 2,6-Dimethoxy-1,4-benzoquinone, a natural phytochemical, is a known haustorial inducing factor. 2,6-Dimethoxy-1,4-benzoquinone exerts anti-cancer, anti-inflammatory, anti-adipogenic, antibacterial, and antimalaria effects[1]. 2,6-Dimethoxy-1,4-benzoquinone, a natural phytochemical, is a known haustorial inducing factor. 2,6-Dimethoxy-1,4-benzoquinone exerts anti-cancer, anti-inflammatory, anti-adipogenic, antibacterial, and antimalaria effects[1].

Mammeisin

C25H26O5 (406.178)

Mammeisin is found in fruits. Mammeisin is a constituent of Mammea americana (mamey) Constituent of Mammea americana (mamey). Mammeisin is found in fruits.

Calophyllin B

C18H16O4 (296.1049)

A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1 and 5 and a prenyl group at position 6.

Dehydrocycloguanandin

C18H14O4 (294.0892)

Euxanthone

C13H8O4 (228.0423)

Occurs in Mammea americana (mamey), Platonia insignis (bakuri) and Mangifera indica (mango). Euxanthone is found in fruits and mammee apple. Euxanthone is found in fruits. Euxanthone occurs in Mammea americana (mamey), Platonia insignis (bakuri) and Mangifera indica (mango

Gentiacaulein

C15H12O6 (288.0634)

Gentisein

C13H8O5 (244.0372)

Gentisein is a member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7. It has a role as a plant metabolite. It is a member of xanthones and a polyphenol. Gentisein is a natural product found in Hypericum scabrum, Cratoxylum formosum, and other organisms with data available. A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 3 and 7. Gentisein is found in alcoholic beverages. Gentisein is isolated from Gentiana lutea (yellow gentian Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2]. Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2]. Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2].

Gentisin

C14H10O5 (258.0528)

Gentisin is found in alcoholic beverages. Gentisin is a pigment from root of Gentiana lutea (yellow gentian

Jacareubin

C18H14O6 (326.079)

Macluraxanthone

C23H22O6 (394.1416)

Mesuaxanthone B

C13H8O5 (244.0372)

A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1, 5 and 6.

1,3,5-Trihydroxyxanthone

C13H8O5 (244.0372)

A member of the class of xanthones that is xanthone substituted by hydroxy groups at positions 1, 3 and 5. It has been isolated from Anaxagorea luzonensis.

Domoic acid

C15H21NO6 (311.1369)

D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents > D009466 - Neuromuscular Blocking Agents Isodomoic acid F is found in mollusks. Isodomoic acid F is isolated from mussels. Isolated from mussels. Isodomoic acid F is found in mollusks.

simiarenol

C30H50O (426.3861)

(-)-Epiafzelechin

C15H14O5 (274.0841)

(-)-Epiafzelechin is found in fruits. (-)-Epiafzelechin is a constituent of Actinidia chinensis (kiwi fruit) and Juniperus communis (juniper) Constituent of Actinidia chinensis (kiwi fruit) and Juniperus communis (juniper). (-)-Epiafzelechin is found in kiwi, tea, and fruits.

Coal tar

C15H10O4 (254.0579)

4-Phenyl-7,8-dihydroxycoumarin is a coumarin derivative and can be used for bronchiectasiss research[1].

Xanthone

C13H8O2 (196.0524)

Xanthone is the parent compound of the xanthone class consisting of xanthene bearing a single oxo substituent at position 9. It has a role as an insecticide. Xanthone is a natural product found in Harungana madagascariensis, Garcinia dulcis, and other organisms with data available. Xanthone is isolated from Mangosteen and is known to control cell division and growth, apoptosis, inflammation, and metastasis in different stages of carcinogenesis. Xanthone has anti-oxidant, anti-tumor, anti-allergic, anti-inflammatory, anti-bacterial, anti-fungal, and anti-viral activities[1]. Xanthone is isolated from Mangosteen and is known to control cell division and growth, apoptosis, inflammation, and metastasis in different stages of carcinogenesis. Xanthone has anti-oxidant, anti-tumor, anti-allergic, anti-inflammatory, anti-bacterial, anti-fungal, and anti-viral activities[1].

Mammea A/BA

C25H26O5 (406.178)

Mammea A/BA is a neoflavonoid. It has a role as a metabolite. Mammea A/BA is a natural product found in Mammea americana, Mesua ferrea, and Calophyllum brasiliense with data available. Constituent of Mammea americana (mamey) seeds. Mammea A/BA is found in fruits and mammee apple. Mammea A/BA is found in fruits. Mammea A/BA is a constituent of Mammea americana (mamey) seeds A natural product found in Mammea americana.

Isovanillic acid

C8H8O4 (168.0423)

Isovanillic acid is a metabolite of isovanillin. Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin. It is a selective inhibitor of aldehyde oxidase. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid. (Wikipedia) Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid isolated from isolated from Scrophularia ningpoensis, with Anti-inflammatory activity[1]. Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid isolated from isolated from Scrophularia ningpoensis, with Anti-inflammatory activity[1].

3,5-Dimethoxybenzoic acid

C9H10O4 (182.0579)

3,5-Dimethoxybenzoic acid, isolated from Melia azedarach L. leaves with antifungal activity, is an intermediate in organic synthesis[1]. 3,5-Dimethoxybenzoic acid, isolated from Melia azedarach L. leaves with antifungal activity, is an intermediate in organic synthesis[1].

Demethylcalabaxanthone

C23H22O5 (378.1467)

Demethylcalabaxanthone is found in fruits. Demethylcalabaxanthone is a constituent of Garcinia mangostana (mangosteen) Constituent of Garcinia mangostana (mangosteen). Demethylcalabaxanthone is found in fruits and purple mangosteen.

6-Hydroxy-9,9-dimethyl-5-(3-methyl-1-oxobutyl)-1-propyl-3H,9H-[1,2]-dioxolo[3',4':4,5]furo[2,3-f][1]benzopyran-3-one

C22H26O7 (402.1678)

6-Hydroxy-9,9-dimethyl-5-(3-methyl-1-oxobutyl)-1-propyl-3H,9H-[1,2]-dioxolo[3,4:4,5]furo[2,3-f][1]benzopyran-3-one is found in fruits. 6-Hydroxy-9,9-dimethyl-5-(3-methyl-1-oxobutyl)-1-propyl-3H,9H-[1,2]-dioxolo[3,4:4,5]furo[2,3-f][1]benzopyran-3-one is isolated from Mammea americana (mamey). 6-Hydroxy-9,9-dimethyl-5-(3-methyl-1-oxobutyl)-1-propyl-3H,9H-[1,2]-dioxolo[3,4:4,5]furo[2,3-f][1]benzopyran-3-one is an oxidation produced of Mammein.

Mammea A/AC cyclo F

C24H24O6 (408.1573)

Mammea A/AC cyclo F is found in fruits. Mammea A/AC cyclo F is a constituent of Mammea americana (mamey). Constituent of Mammea americana (mamey). Mammea A/AC cyclo F is found in fruits.

Mammeigin

C25H24O5 (404.1624)

Constituent of Mammea americana (mamey). Mammeigin is found in fruits and mammee apple. Mammeigin is found in fruits. Mammeigin is a constituent of Mammea americana (mamey)

Mammea A/BB

C25H26O5 (406.178)

Constituent of Mammea americana (mamey) seeds. Mammea A/BB is found in fruits and mammee apple. Mammea A/BB is found in fruits. Mammea A/BB is a constituent of Mammea americana (mamey) seeds

Mammea E/BB

C24H30O7 (430.1991)

Mammea E/BB is found in fruits. Mammea E/BB is isolated from seeds of Mammea americana (mamey

Mammea B/BA

C22H28O5 (372.1937)

Mammea B/BA is found in fruits. Mammea B/BA is a constituent of Mammea americana (mamey) seeds

Mammea B/AC cyclo D

C21H24O5 (356.1624)

Mammea B/AC cyclo D is found in fruits. Mammea B/AC cyclo D is isolated from Mammea americana (mamey). Isolated from Mammea americana (mamey). Mammea B/AC cyclo D is found in fruits.

Mesuagin

C24H22O5 (390.1467)

Constituent of seeds of Mammea americana (mamey). Mesuagin is found in fruits and mammee apple. Mesuagin is found in fruits. Mesuagin is a constituent of seeds of Mammea americana (mamey)

Alloathyriol

C14H10O6 (274.0477)

Alloathyriol is found in fruits. Alloathyriol is a constituent of Garcinia dulcis (mundu). Constituent of Garcinia dulcis (mundu). Alloathyriol is found in fruits.

Calabaxanthone

C24H24O5 (392.1624)

Calabaxanthone is found in fruits. Calabaxanthone is a constituent of Garcinia mangostana (mangosteen)

Garcinone B

C23H22O6 (394.1416)

Constituent of Garcinia mangostana (mangosteen). Garcinone B is found in fruits and purple mangosteen. Garcinone B is found in fruits. Garcinone B is a constituent of Garcinia mangostana (mangosteen)

(S)-Neomammein

C22H28O5 (372.1937)

(S)-Neomammein is found in fruits. (S)-Neomammein is a constituent of Mammea americana (mamey) seeds. Constituent of Mammea americana (mamey) seeds. (S)-Neomammein is found in fruits.

Afzelechin

C15H14O5 (274.0841)

Afzelechin is a flavan-3-ol, a type of flavonoid. It exists as at least 2 major epimers (afzelechin and epi-afzelechin). It is produced through the transformation of cis-3,4lecuopelargonidin through the action of (2R,3S)-catechin:NADP+ 4-oxidoreductase. Afzelechin can be found in many plants native to Asia such as: Astilbe rivularis (also known as waterside astilbe), Bergenia ligulate (also known as Paashaanbhed in Ayurveda traditional Indian medicine), and Wisteria floribunda (Japanese wisteria). Afzelechin also occurs in barley and rye as a member of the proanthocyanidins found in these crop plants. Afzelechin exhibits moderate inhibitory effects on tumor necrosis factor alpha (TNF-α) induced nuclear factor kappa-B (NF-kB) activation in HepG2 cells (PMID: 21985227). Afzelechin is only found in individuals who have consumed barley/rye or taken certain herbal medicines containing this compound.

Carissic acid

C30H48O3 (456.3603)

Ustiloxin E is found in cereals and cereal products. Ustiloxin E is isolated from the false smut balls caused by Ustilaginoidea virens on rice. Constituent of Carissa carandas (karanda). Carissic acid is found in beverages and fruits.

(2R)-2,5,8-Trimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol

C28H42O2 (410.3185)

(2R)-2,8-Dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)-3,4-dihydrochromen-6-ol

C27H40O2 (396.3028)

alpha-Amyrin

C30H50O (426.3861)

Epi-alpha-amyrin, also known as epi-α-amyrin, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Epi-alpha-amyrin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Epi-alpha-amyrin can be found in herbs and spices, pomes, and rosemary, which makes epi-alpha-amyrin a potential biomarker for the consumption of these food products.

beta-Amyrin

C30H50O (426.3861)

Beta-amryin, also known as B-amryin, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Beta-amryin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amryin can be found in pigeon pea, which makes beta-amryin a potential biomarker for the consumption of this food product.

Calanolide A

C22H26O5 (370.178)

Epi-Friedelanol

C30H52O (428.4018)

Friedelin

C30H50O (426.3861)

Friedelin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Friedelin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Friedelin can be found in a number of food items such as apple, pear, mammee apple, and sugar apple, which makes friedelin a potential biomarker for the consumption of these food products. Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant .

kainic acid

C10H15NO4 (213.1001)

Lupenone

C30H48O (424.3705)

1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-one belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. 1,2,5,14,18,18-hexamethyl-8-(prop-1-en-2-yl)pentacyclo[11.8.0.0²,¹⁰.0⁵,⁹.0¹⁴,¹⁹]henicosan-17-one is an extremely weak basic (essentially neutral) compound (based on its pKa). This compound has been identified in human blood as reported by (PMID: 31557052 ). Lupenone is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Lupenone is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources.

Mesuol

C24H24O5 (392.1624)

Morelloflavone

C30H20O11 (556.1006)

Taraxerone

C30H48O (424.3705)

XANTHONE

C13H8O2 (196.0524)

Xanthone is isolated from Mangosteen and is known to control cell division and growth, apoptosis, inflammation, and metastasis in different stages of carcinogenesis. Xanthone has anti-oxidant, anti-tumor, anti-allergic, anti-inflammatory, anti-bacterial, anti-fungal, and anti-viral activities[1]. Xanthone is isolated from Mangosteen and is known to control cell division and growth, apoptosis, inflammation, and metastasis in different stages of carcinogenesis. Xanthone has anti-oxidant, anti-tumor, anti-allergic, anti-inflammatory, anti-bacterial, anti-fungal, and anti-viral activities[1].

Simiarenol

C30H50O (426.3861)

Simiarenol belongs to steroids and steroid derivatives class of compounds. Those are compounds based on the cyclopenta[a]phenanthrene carbon skeleton, partially or completely hydrogenated; there are usually methyl groups at C-10 and C-13, and often an alkyl group at C-17. By extension, one or more bond scissions, ring expansions and/or ring contractions of the skeleton may have occurred. Simiarenol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Simiarenol can be found in soy bean, which makes simiarenol a potential biomarker for the consumption of this food product.

C14:0

C14H28O2 (228.2089)

Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.

3,4-Dihydroxybenzaldehyde

C7H6O3 (138.0317)

Protocatechualdehyde, also known as rancinamycin iv or 1,2-dihydroxy-4-formylbenzene, is a member of the class of compounds known as hydroxybenzaldehydes. Hydroxybenzaldehydes are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Protocatechualdehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Protocatechualdehyde is an almond, bitter, and dry tasting compound and can be found in a number of food items such as plains prickly pear, mugwort, silver linden, and cardamom, which makes protocatechualdehyde a potential biomarker for the consumption of these food products. Protocatechualdehyde can be found primarily in urine. This molecule can be used as a precursor in the vanillin synthesis by biotransformation by cell cultures of Capsicum frutescens, a type of Chili pepper. It is also found in the mushroom Phellinus linteus . 3,4-dihydroxybenzaldehyde is a dihydroxybenzaldehyde. Also known as protocatechuic aldehyde, protocatechualdehyde is a naturally-occuring phenolic aldehyde that is found in barley, green cavendish bananas, grapevine leaves and root of the herb S. miltiorrhiza. Protocatechualdehyde possesses antiproliferative and pro-apoptotic properties against human breast cancer cells and colorectal cancer cells by reducing the expression of pro-oncogenes β-catenin and cyclin D1. 3,4-Dihydroxybenzaldehyde is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. See also: Black Cohosh (part of). 3,4-Dihydroxybenzaldehyde, also known as protocatechuic aldehyde, is a phenolic aldehyde, a compound released from cork stoppers into wine. This molecule can be used as a precursor in vanillin synthesis via biotransformation by cell cultures of Capsicum frutescens, a type of chili pepper. It is also found in the mushroom Phellinus linteus (Wikipedia). D006401 - Hematologic Agents > D000925 - Anticoagulants Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

Gentisin

C14H10O5 (258.0528)

Gentisin is a member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1 and 7 and a methoxy group at position 3. It has a role as a plant metabolite. It is a member of xanthones, a polyphenol and an aromatic ether. Gentisin is a natural product found in Pterocarpus santalinus, Gentiana orbicularis, and other organisms with data available. See also: Menyanthes trifoliata leaf (part of). A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 1 and 7 and a methoxy group at position 3. Gentisin is found in alcoholic beverages. Gentisin is a pigment from root of Gentiana lutea (yellow gentian

Apetalic acid

C22H28O6 (388.1886)

Ochrocarpinone C

C33H42O5 (518.3032)

A beta-diketone isolated from Ochrocarpos punctatus and has been shown to exhibit antineoplastic activity.

Inophyllolide chromanol

C25H24O5 (404.1624)

Ursolic Acid

C30H48O3 (456.3603)

Origin: Plant; SubCategory_DNP: Triterpenoids relative retention time with respect to 9-anthracene Carboxylic Acid is 1.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.640 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.638 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.642 Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

Ochrocarpinone B

C33H42O5 (518.3032)

A beta-diketone isolated from Ochrocarpos punctatus and has been shown to exhibit antineoplastic activity.

OCHROCARPINONE A

C33H42O6 (534.2981)

A beta-diketone isolated from Ochrocarpos punctatus and has been shown to exhibit antineoplastic activity.

Calophyllic acid

C25H24O6 (420.1573)

Ochrocarpin G

C24H30O8 (446.1941)

A furanocoumarin that is 8,9-dihydro-2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, a 2-hydroxypropan-2-yl group at position 8, 2-methylbutanoyl group at position 6 and a (1R)-1-(acetyloxy)propyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.

Pinetoric acid I

C23H30O6 (402.2042)

OCHROCARPIN E

C24H24O6 (408.1573)

A furanocoumarin that is 2,3-dihydro-7H-furo[2,3-f]chromen-7-one substituted by a hydroxy group at position 4, a 2-hydroxypropan-2-yl group at position 2, a 2-methylpropanoyl group at position 5 and a phenyl group at position 9. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.

brasixanthone C

C23H22O7 (410.1365)

A member of the class of pyranoxanthones that is 2H,6H-pyrano[3,2-b]xanthen-6-one substituted by a 2-hydroperoxy-3-methylbut-3-en-1-yl moiety at position 12, hydroxy groups at positions 5 and 8 and geminal methyl groups at position 2. It is isolated from the stem bark of Calophyllum brasiliense and exhibits significant inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate induced Epstein-Barr virus early antigen activation in Raji cells.

Pinetoxanthone

C23H24O5 (380.1624)

Cudraxanthone G

C24H26O5 (394.178)

β-Amyrin

C30H50O (426.3861)

Beta-amyrin, also known as amyrin or (3beta)-olean-12-en-3-ol, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, beta-amyrin is considered to be an isoprenoid lipid molecule. Beta-amyrin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amyrin can be synthesized from oleanane. Beta-amyrin is also a parent compound for other transformation products, including but not limited to, erythrodiol, glycyrrhetaldehyde, and 24-hydroxy-beta-amyrin. Beta-amyrin can be found in a number of food items such as thistle, pepper (c. baccatum), wakame, and endive, which makes beta-amyrin a potential biomarker for the consumption of these food products. The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee . β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

Palmitic Acid

C16H32O2 (256.2402)

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

isovanillic acid

C8H8O4 (168.0423)

Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid isolated from isolated from Scrophularia ningpoensis, with Anti-inflammatory activity[1]. Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid isolated from isolated from Scrophularia ningpoensis, with Anti-inflammatory activity[1].

Isoapetalic acid

C22H28O6 (388.1886)

N-Benzyl-L-prolineethylester is a natural product found in Calophyllum blancoi and Calophyllum calaba with data available.

Calolongic acid

C22H28O6 (388.1886)

4-Methoxysalicylic acid

C8H8O4 (168.0423)

2-hydroxy-4-methoxybenzoic acid belongs to P-methoxybenzoic acids and derivatives class of compounds. Those are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. 2-hydroxy-4-methoxybenzoic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 2-hydroxy-4-methoxybenzoic acid can be found in evening primrose, which makes 2-hydroxy-4-methoxybenzoic acid a potential biomarker for the consumption of this food product. 2-Hydroxy-4-methoxybenzoic acid is a derivative of methoxybenzoic. 2-Hydroxy-4-methoxybenzoic is a potential biomarker. 2-Hydroxy-4-methoxybenzoic acid is a derivative of methoxybenzoic. 2-Hydroxy-4-methoxybenzoic is a potential biomarker.

Mesuaxanthone A

C14H10O5 (258.0528)

Pancixanthone B

C18H16O5 (312.0998)

A member of the class of xanthones that is a tetracyclic compound 1,2-dihydro-6H-furo[2,3-c]xanthen-6-one substituted by hydroxy groups at positions 5 and 10 and methyl groups at positions 1,1 and 2. It has been isolated from Calophyllum pauciflorum and Garcinia vieillardii.

sitosterol

C29H50O (414.3861)

A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

Mesuol

C24H24O5 (392.1624)

Mesuol is a neoflavonoid. Mesuol is a natural product found in Mesua ferrea and Mammea siamensis with data available.

Stigmasterol

C29H48O (412.3705)

Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong.

Apetalolide

C26H24O5 (416.1624)

Mesuagin

C24H22O5 (390.1467)

Quercitrin

C21H20O11 (448.1006)

Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2]. Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2]. Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2].

Quercetin

C15H10O7 (302.0427)

Annotation level-1 COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials relative retention time with respect to 9-anthracene Carboxylic Acid is 0.898 D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.902 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 1981; CONFIDENCE confident structure IPB_RECORD: 3301; CONFIDENCE confident structure IPB_RECORD: 3283; CONFIDENCE confident structure Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

TRIBUTYL CITRATE

C18H32O7 (360.2148)

Xanthone

C13H8O2 (196.0524)

CONFIDENCE standard compound; INTERNAL_ID 198; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9192; ORIGINAL_PRECURSOR_SCAN_NO 9189 CONFIDENCE standard compound; INTERNAL_ID 198; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9263; ORIGINAL_PRECURSOR_SCAN_NO 9262 CONFIDENCE standard compound; INTERNAL_ID 198; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9233; ORIGINAL_PRECURSOR_SCAN_NO 9231 CONFIDENCE standard compound; INTERNAL_ID 198; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9258; ORIGINAL_PRECURSOR_SCAN_NO 9255 CONFIDENCE standard compound; INTERNAL_ID 198; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9245; ORIGINAL_PRECURSOR_SCAN_NO 9242 CONFIDENCE standard compound; INTERNAL_ID 198; DATASET 20200303_ENTACT_RP_MIX501; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9280; ORIGINAL_PRECURSOR_SCAN_NO 9279 Xanthone is isolated from Mangosteen and is known to control cell division and growth, apoptosis, inflammation, and metastasis in different stages of carcinogenesis. Xanthone has anti-oxidant, anti-tumor, anti-allergic, anti-inflammatory, anti-bacterial, anti-fungal, and anti-viral activities[1]. Xanthone is isolated from Mangosteen and is known to control cell division and growth, apoptosis, inflammation, and metastasis in different stages of carcinogenesis. Xanthone has anti-oxidant, anti-tumor, anti-allergic, anti-inflammatory, anti-bacterial, anti-fungal, and anti-viral activities[1].

4-Methoxy-9H-xanthen-9-one

C14H10O3 (226.063)

3,6-Dihydroxy-2-methoxybenzoic acid

C8H8O5 (184.0372)

lupeol

C30H50O (426.3861)

D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

OCHROCARPIN C

C24H22O6 (406.1416)

A furanocoumarin that is 2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, 2-hydroxypropan-2-yl group at position 8, a 2-methylpropanoyl group at position 6 and a phenyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.

OCHROCARPIN B

C25H24O6 (420.1573)

A furanocoumarin that is 2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, 2-hydroxypropan-2-yl group at position 8, a 3-methylbutanoyl group at position 6 and a phenyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.

blancoxanthone

C23H22O5 (378.1467)

A member of the class of pyranoxanthones that is 2H,6H-pyrano[3,2-b]xanthen-6-one substituted by hydroxy groups at positions 5 and 10, geminal methyl groups at position 2 and a 2-methylbut-3-en-2-yl group at position 12. It is isolated from the roots of Calophyllum blancoi and exhibits antiviral activity against coronavirus.

Squalene

C30H50 (410.3912)

Squalene, also known as (e,e,e,e)-squalene or all-trans-squalene, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Squalene can be found in a number of food items such as apricot, savoy cabbage, peach (variety), and bitter gourd, which makes squalene a potential biomarker for the consumption of these food products. Squalene can be found primarily in blood, feces, and sweat, as well as throughout most human tissues. In humans, squalene is involved in several metabolic pathways, some of which include risedronate action pathway, steroid biosynthesis, alendronate action pathway, and fluvastatin action pathway. Squalene is also involved in several metabolic disorders, some of which include cholesteryl ester storage disease, CHILD syndrome, hyper-igd syndrome, and wolman disease. Squalene is a natural 30-carbon organic compound originally obtained for commercial purposes primarily from shark liver oil (hence its name, as Squalus is a genus of sharks), although plant sources (primarily vegetable oils) are now used as well, including amaranth seed, rice bran, wheat germ, and olives. Yeast cells have been genetically engineered to produce commercially useful quantities of "synthetic" squalene . COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].

1,3-dihydroxy-5,6-dimethoxyxanthen-9-one

C15H12O6 (288.0634)

3-hydroxy-2-methoxyxanthen-9-one

C14H10O4 (242.0579)

Lupenone

C30H48O (424.3705)

Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2]. Lupenone is an orally active lupine-type triterpenoid that can be isolated from Musa basjoo. Lupenone Lupenone plays a role through the PI3K/Akt/mTOR and NF-κB signaling pathways. Lupenone has anti-inflammatory, antiviral, antidiabetic and anticancer activities[1][2][3]. Lupenone, isolated from Musa basjoo, belongs to lupane type triterpenoids. Lupenone shows various pharmacological activities including anti-inflammatory, anti-virus, anti-diabetes, anti-cancer, improving Chagas disease without major toxicity[1][2].

Taraxerone

C30H48O (424.3705)

Taraxerol

C30H50O (426.3861)

Taraxerol is a pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15. It has a role as a metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. Taraxerol is a natural product found in Diospyros morrisiana, Liatris acidota, and other organisms with data available. See also: Myrica cerifera root bark (part of). A pentacyclic triterpenoid that is oleanan-3-ol lacking the methyl group at position 14, with an alpha-methyl substituent at position 13 and a double bond between positions 14 and 15.

betulinic acid

C30H48O3 (456.3603)

Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4].

Amentoflavone

C30H18O10 (538.09)

D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065688 - Cytochrome P-450 CYP2C9 Inhibitors D004791 - Enzyme Inhibitors > D065607 - Cytochrome P-450 Enzyme Inhibitors > D065692 - Cytochrome P-450 CYP3A Inhibitors Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 4341; CONFIDENCE confident structure Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4]. Amentoflavone (Didemethyl-ginkgetin) is a potent and orally active GABA(A) negative modulator. Amentoflavone also shows anti-inflammatory, antioxidative, anti-viral, anti-tumor, anti-radiation, anti-fungal, antibacterial activity. Amentoflavone induces apoptosis and cell cycle arrest at sub-G1 phase[1][2][3][4].

1,2,8-trimethoxy-9h-xanthen-9-one

C16H14O5 (286.0841)

Mammea C/AA

C24H32O5 (400.225)

A natural product found in Mammea americana.

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].

Oleanolic Acid

C30H48O3 (456.3603)

8-acetyl-5-hydroxy-6-(3-methylbutanoyl)-4-phenyl-2H-furo[2,3-h]chromen-2-one

C24H20O6 (404.126)

2,7-Dihydroxy-1,8-dimethoxy-9H-xanthen-9-one

C15H12O6 (288.0634)

pyranojacareubin

C23H20O6 (392.126)

An organic heteropentacyclic compound that is 2H,6H,10H-dipyrano[3,2-b:2,3-i]xanthene substituted by hydroxy groups at positions 5 and 12, geminal methyl groups at positions 2 and 10 and an oxo group at position 6. Isolated from Calophyllum blancoi it exhibits antiviral activity.

2,3-dimethoxyxanthen-9-one

C15H12O4 (256.0736)

6-hydroxy-1-methoxy-9H-xanthen-9-one

C14H10O4 (242.0579)

3-hydroxy-1,2-dimethoxy-9H-xanthen-9-one

C15H12O5 (272.0685)

brasixanthone B

C23H22O5 (378.1467)

A member of the class of pyranoxanthones that is 2H,6H-pyrano[3,2-b]xanthen-6-one substituted by hydroxy, geminal methyl and a prenyl group at positions 5, 8, 2 and 12 respectively. It is isolated from the stem bark of Calophyllum brasiliense and exhibits significant inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate induced Epstein-Barr virus early antigen activation in Raji cells.

Nervonic acid

C24H46O2 (366.3498)

Nervonic acid is a monounsaturated fatty acid important in the biosynthesis of myelin. Nervonic acid is a monounsaturated fatty acid important in the biosynthesis of myelin.

7,8-dihydroxy-4-phenyl-2H-chromen-2-one

C15H10O4 (254.0579)

Morelloflavone

C30H20O11 (556.1006)

(+)-morelloflavone is a biflavonoid found in Rheedia edulis and Garcinia livingstonei. It has a role as a plant metabolite. It is a biflavonoid, a hydroxyflavone and a hydroxyflavanone. (+)-Morelloflavone is a natural product found in Garcinia multiflora, Garcinia intermedia, and other organisms with data available. A biflavonoid found in Rheedia edulis and Garcinia livingstonei.

Kainic acid

C10H15NO4 (213.1001)

Kainic acid is a dicarboxylic acid, a pyrrolidinecarboxylic acid, a L-proline derivative and a non-proteinogenic L-alpha-amino acid. It has a role as an antinematodal drug and an excitatory amino acid agonist. It is a conjugate acid of a kainate(1-). (2S-(2 alpha,3 beta,4 beta))-2-Carboxy-4-(1-methylethenyl)-3-pyrrolidineacetic acid. Ascaricide obtained from the red alga Digenea simplex. It is a potent excitatory amino acid agonist at some types of excitatory amino acid receptors and has been used to discriminate among receptor types. Like many excitatory amino acid agonists it can cause neurotoxicity and has been used experimentally for that purpose. D018377 - Neurotransmitter Agents > D018683 - Excitatory Amino Acid Agents > D018690 - Excitatory Amino Acid Agonists D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics C254 - Anti-Infective Agent > C276 - Antiparasitic Agent > C250 - Antihelminthic Agent Kainic acid is a potent excitotoxic agent. Kainic acid hydrate also is an agonist for a subtype of ionotropic glutamate receptor. Kainic acid induces seizures[1][2]. Kainic acid is a potent excitotoxic agent. Kainic acid hydrate also is an agonist for a subtype of ionotropic glutamate receptor. Kainic acid induces seizures[1][2].

Euxanthone

C13H8O4 (228.0423)

Euxanthone is a member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1 and 7 and an oxo group at position 9. It has been isolated from Cratoxylum cochinchinense. It has a role as a plant metabolite and a metabolite. It is a member of xanthones and a member of phenols. Euxanthone is a natural product found in Garcinia oblongifolia, Hypericum scabrum, and other organisms with data available. A member of the class of xanthones that is 9H-xanthene substituted by hydroxy group at positions 1 and 7 and an oxo group at position 9. It has been isolated from Cratoxylum cochinchinense. Occurs in Mammea americana (mamey), Platonia insignis (bakuri) and Mangifera indica (mango). Euxanthone is found in fruits and mammee apple. Euxanthone is found in fruits. Euxanthone occurs in Mammea americana (mamey), Platonia insignis (bakuri) and Mangifera indica (mango

Rhamnetin

C16H12O7 (316.0583)

Rhamnetin is a monomethoxyflavone that is quercetin methylated at position 7. It has a role as a metabolite, an antioxidant and an anti-inflammatory agent. It is a monomethoxyflavone and a tetrahydroxyflavone. It is functionally related to a quercetin. It is a conjugate acid of a rhamnetin-3-olate. Rhamnetin is a natural product found in Ageratina altissima, Ammannia auriculata, and other organisms with data available. A monomethoxyflavone that is quercetin methylated at position 7. 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one, also known as 7-methoxyquercetin or quercetin 7-methyl ether, is a member of the class of compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one can be found in a number of food items such as tea, apple, sweet orange, and parsley, which makes 2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7-methoxy-4h-chromen-4-one a potential biomarker for the consumption of these food products. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1]. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1]. Rhamnetin is a quercetin derivative found in Coriandrum sativum, inhibits secretory phospholipase A2, with antioxidant and anti-inflammatory activity[1].

Erucic acid

C22H42O2 (338.3185)

Sucrose

C12H22O11 (342.1162)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Catechol

C15H14O6 (290.079)

Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

Lignoceric acid

C24H48O2 (368.3654)

A C24 straight-chain saturated fatty acid. Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid, which is synthesized in the developing brain. Lignoceric acid is also a by-product of lignin production. Lignoceric acid can be used for Zellweger cerebro‐hepato‐renal syndrome and adrenoleukodystrophy research[1][2]. Lignoceric acid (Tetracosanoic acid) is a 24-carbon saturated (24:0) fatty acid, which is synthesized in the developing brain. Lignoceric acid is also a by-product of lignin production. Lignoceric acid can be used for Zellweger cerebro‐hepato‐renal syndrome and adrenoleukodystrophy research[1][2].

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].

protocatechuic aldehyde

C7H6O3 (138.0317)

Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1]. Protocatechualdehyde (Catechaldehyde), a natural polyphenol compound isolated from the roots of radix Salviae Miltiorrhizae, is associated with a wide variety of biological activities and has been widely used in medicine as an antioxidant, anti-aging, an antibacterial and anti-inflammatory agent[1].

Myristic Acid

C14H28O2 (228.2089)

Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.

Behenic acid

C22H44O2 (340.3341)

A straight-chain, C22, long-chain saturated fatty acid. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans.

stearic acid

C18H36O2 (284.2715)

Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Oleic acid

C18H34O2 (282.2559)

An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry. Oleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=112-80-1 (retrieved 2024-07-16) (CAS RN: 112-80-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

Palmitoleic acid

C16H30O2 (254.2246)

A hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration. In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. Trans-hexa-dec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-hexa-dec-2-enoic acid converted from (R)-3-Hydroxy-hexadecanoic acid via two enzymes; fatty-acid Synthase and 3- Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61). [HMDB] Cis-9-palmitoleic acid, also known as palmitoleate or (Z)-9-hexadecenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, cis-9-palmitoleic acid is considered to be a fatty acid lipid molecule. Cis-9-palmitoleic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-9-palmitoleic acid can be found in a number of food items such as red huckleberry, highbush blueberry, butternut, and macadamia nut (m. tetraphylla), which makes cis-9-palmitoleic acid a potential biomarker for the consumption of these food products. Cis-9-palmitoleic acid can be found primarily in most biofluids, including blood, saliva, feces, and urine, as well as in human adipose tissue, prostate and skeletal muscle tissues. Cis-9-palmitoleic acid exists in all living species, ranging from bacteria to humans. Moreover, cis-9-palmitoleic acid is found to be associated with isovaleric acidemia. CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5949; ORIGINAL_PRECURSOR_SCAN_NO 5948 INTERNAL_ID 900; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5959; ORIGINAL_PRECURSOR_SCAN_NO 5958 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5959; ORIGINAL_PRECURSOR_SCAN_NO 5958 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5926; ORIGINAL_PRECURSOR_SCAN_NO 5924 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5944; ORIGINAL_PRECURSOR_SCAN_NO 5943 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5997; ORIGINAL_PRECURSOR_SCAN_NO 5996 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5943; ORIGINAL_PRECURSOR_SCAN_NO 5941 Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats. Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.

1,6-dihydroxy-5-methoxyxanthen-9-one

C14H10O5 (258.0528)

3-hydroxy-4-methoxyxanthen-9-one

C14H10O4 (242.0579)

Betulin

C30H50O2 (442.3811)

Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.

Domoic acid

C15H21NO6 (311.1369)

An L-proline derivative that is L-proline substituted by a carboxymethyl group at position 3 and a 6-carboxyhepta-2,4-dien-2-yl group at position 4. It is produced by the diatomic algal Pseudo-nitzschia. It is an analogue of kainic acid and a neurotoxin which causes amnesic shellfish poisoning (ASP). D018373 - Peripheral Nervous System Agents > D009465 - Neuromuscular Agents > D009466 - Neuromuscular Blocking Agents

Arachidic acid

C20H40O2 (312.3028)

Arachidonic acid (Icosanoic acid), a long-chain fatty acid, is present in all mammalian cells, typically esterified to membrane phospholipids, and is one of the most abundant polyunsaturated fatty acids present in human tissue[1][2]. Arachidonic acid (Icosanoic acid), a long-chain fatty acid, is present in all mammalian cells, typically esterified to membrane phospholipids, and is one of the most abundant polyunsaturated fatty acids present in human tissue[1][2].

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266)

Kainic acid

C10H15NO4 (213.1001)

Annotation level-1

Hexadecanoic acid

C16H32O2 (256.2402)

Octadecanoic acid

C18H36O2 (284.2715)

A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.

Tetradecanoic acid

C14H28O2 (228.2089)

shikimate

C7H10O5 (174.0528)

Shikimic acid, also known as shikimate or 3,4,5-trihydroxy-1-cyclohexenecarboxylic acid, is a member of the class of compounds known as shikimic acids and derivatves. Shikimic acids and derivatves are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. Shikimic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Shikimic acid can be found in a number of food items such as date, rocket salad, redcurrant, and poppy, which makes shikimic acid a potential biomarker for the consumption of these food products. Shikimic acid can be found primarily in blood and urine. Shikimic acid exists in all living species, ranging from bacteria to humans. Shikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical metabolite in plants and microorganisms. Its name comes from the Japanese flower shikimi (シキミ, the Japanese star anise, Illicium anisatum), from which it was first isolated in 1885 by Johan Fredrik Eykman. The elucidation of its structure was made nearly 50 years later . Shikimic acid is a key metabolic intermediate of the aromatic amino acid biosynthesis pathway, found in microbes and plants. Shikimic acid is a key metabolic intermediate of the aromatic amino acid biosynthesis pathway, found in microbes and plants.

3,4-dihydroxybenzaldehyde

C7H6O3 (138.0317)

3-Hydroxy-4-methoxybenzoic acid

C8H8O4 (168.0423)

Mammea A/BA

C25H26O5 (406.178)

Mammea A/BB

C25H26O5 (406.178)

Mammeigin

C25H24O5 (404.1624)

garcinone B

C23H22O6 (394.1416)

Calabaxanthone

C24H24O5 (392.1624)

demethylcalabaxanthone

C23H22O5 (378.1467)

8-Desoxygartanin

C23H24O5 (380.1624)

8-Deoxygartanin, a prenylated xanthones from G. mangostana, is a selective inhibitor of butyrylcholinesterase (BChE)[1]. 8-Deoxygartanin exhibits antiplasmodial activity with an IC50 of 11.8 μM for the W2 strain of Plasmodium falciparum[2]. 8-Deoxygartanin inhibits NF-κB (p65) activation with an IC50 of 11.3 μM[3]. 8-Deoxygartanin, a prenylated xanthones from G. mangostana, is a selective inhibitor of butyrylcholinesterase (BChE)[1]. 8-Deoxygartanin exhibits antiplasmodial activity with an IC50 of 11.8 μM for the W2 strain of Plasmodium falciparum[2]. 8-Deoxygartanin inhibits NF-κB (p65) activation with an IC50 of 11.3 μM[3].

Mammea E/BB

C24H30O7 (430.1991)

A natural product found in Mammea americana.

Mammea E/BA

C24H30O7 (430.1991)

Pyranomammea C

C22H28O6 (388.1886)

Epi-a-amyrin

C30H50O (426.3861)

Carissic acid

C30H48O3 (456.3603)

alloathyriol

C14H10O6 (274.0477)

(S)-Neomammein

C22H28O5 (372.1937)

1,3,6-Trihydroxy-5-methoxyxanthone

C14H10O6 (274.0477)

C22:0

C22H44O2 (340.3341)

Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans. Docosanoic acid is poorly absorbed, and a cholesterol-raising saturated fatty acid in humans.

Mammeisin

C25H26O5 (406.178)

Soulattrolide

C25H24O5 (404.1624)

A member of the class of coumarins that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2,3-h]chromen-2-one substituted by a phenyl group at position 4, methyl groups at positions 6, 6, 10 and 11 and a hydroxy group at position 12 (the 10S,11R,12S stereoisomer). Isolated from Calophyllum brasiliense and Calophyllum soulattri, it exhibits anti-HIV activity.

Calanolide F

C22H26O5 (370.178)

A natural product found in Calophyllum lanigerum var austrocoriaceum and Calophyllum teysmannii var inophylloide. D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents

Friedelane

C30H52 (412.4069)

A triterpene that is docosahydropicene substituted by 8 methyl groups at positions 2, 2, 4a, 6a, 8a, 9, 12b and 14a.

Dihydrobetulinic acid

C30H50O3 (458.376)

A pentacyclic triterpenoid that is lupane having a 3beta-hydroxy and 28-carboxy substituents. Isolated from the leaves of Syzygium claviflorum, it exhibits anti-HIV and antileishmanial activity.

GALOP

C7H6O5 (170.0215)

C26170 - Protective Agent > C275 - Antioxidant Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2]. Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2].

Gentisin

C14H10O5 (258.0528)

Gentisein

C13H8O5 (244.0372)

Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2]. Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2]. Gentisein (NSC 329491), the major metabolite of Mangiferin, shows the most potent serotonin uptake inhibition with an IC50 value of 4.7 μM[1][2].

Euxanthone

C13H8O4 (228.0423)

A natural product found in Cratoxylum cochinchinense.

Gentiacaulein

C15H12O6 (288.0634)

A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy groups at positions 2 and 8 and methoxy groups at positions 1 and 6.

Ochrocarpin A

C25H24O6 (420.1573)

A furanocoumarin that is 2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, 2-hydroxypropan-2-yl group at position 8, a 2-methylbutanoyl group at position 6 and a phenyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.

Mammea F/BB, (-)-

C24H32O6 (416.2199)

A natural product found in Mammea americana.

Mammea A/BB, (-)-

C25H26O5 (406.178)

A natural product found in Mammea americana.

Ochrocarpin D

C26H26O6 (434.1729)

A furanocoumarin that is 2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, 2-methoxypropan-2-yl group at position 8, a 2-methylbutanoyl group at position 6 and a phenyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.

Mammea B/BB, (-)-

C22H28O5 (372.1937)

A natural product found in Mammea americana.

Ochrocarpin F

C24H30O8 (446.1941)

A furanocoumarin that is 8,9-dihydro-2H-furo[2,3-h]chromen-2-one substituted by a hydroxy group at position 5, a 2-hydroxypropan-2-yl group at position 8, 2-methylbutanoyl group at position 6 and a (1S)-1-(acetyloxy)propyl group at position 4. Isolated from the bark of Ochrocarpos punctatus, it exhibits cytotoxicity against the A2780 ovarian cancer cell line.

Mammea A/AB, (-)-

C25H26O5 (406.178)

A natural product found in Mammea americana.

Mammea C/BB, (-)-

C24H32O5 (400.225)

A natural product found in Mammea americana.

Mammea F/BA, (-)-

C24H32O6 (416.2199)

A natural product found in Mammea americana.

Brasixanthone D

C24H24O7 (424.1522)

A member of the class of pyranoxanthones that is 2H,6H-pyrano[3,2-b]xanthen-6-one substituted by a 2-[(2S)-3,3-dimethyloxiran-2-yl]-2-hydroxyethyl group at position 12, hydroxy groups at positions 5 and 8 and geminal methyl groups at position 2. It is isolated from the stem bark of Calophyllum brasiliense and exhibits significant inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate induced Epstein-Barr virus early antigen activation in Raji cells.

Mammea C/AB, (-)-

C24H32O5 (400.225)

A natural product found in Mammea americana.

Mammea B/AB, (-)-

C22H28O5 (372.1937)

A natural product found in Mammea americana.

Calanolide A

C22H26O5 (370.178)

D000890 - Anti-Infective Agents > D000998 - Antiviral Agents > D044966 - Anti-Retroviral Agents

Aucuparin

C14H14O3 (230.0943)

3,5-dihydroxy-p-anisic acid

C8H8O5 (184.0372)

Mammea B/BA

C22H28O5 (372.1937)

A natural product found in Mammea americana.

2-(4-hydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,5,7-triol

C15H14O5 (274.0841)

3-Hydroxy-4-methoxyxanthen-9-one

C14H10O4 (242.0579)

(-)-calanolide B

C22H26O5 (370.178)

An organic heterotetracyclic compound that is 11,12-dihydro-2H,6H,10H-dipyrano[2,3-f:2,3-h]chromen-2-one substituted by a hydroxy group at position 12, methyl groups at positions 6, 6, 10 and 11 and a propyl group at position 4 (the 10S,11R,12S stereoisomer). Isolated from Calophyllum lanigerum var austrocoriaceum and Calophyllum brasiliense, it exhibits potent activity against HIV-1 reverse transcriptase.

Icosanoic acid

C20H40O2 (312.3028)

A C20 striaght-chain saturated fatty acid which forms a minor constituent of peanut (L. arachis) and corn oils. Used as an organic thin film in the production of liquid crystals for a wide variety of technical applications.

(11Z)-icos-11-enoic acid

C20H38O2 (310.2872)

An icosenoic acid having a cis- double bond at position 11.

shikimate

C7H9O5 (173.045)

A cyclohexenecarboxylate that is the conjugate base of shikimic acid.

3-[(7r,8s)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]-3-phenylpropanoic acid

C25H26O6 (422.1729)

9-hydroxy-5a-({[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-5b,8,8,11a-tetramethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

C39H54O6 (618.392)

(1s)-1-[8-butanoyl-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-2-oxochromen-4-yl]propyl acetate

C23H28O7 (416.1835)

(3s,4r,4as,6as,6br,8as,12as,12bs,14as,14bs)-8a-(hydroxymethyl)-4,4a,6b,11,11,12b,14a-heptamethyl-hexadecahydropicen-3-ol

C30H52O2 (444.3967)

(3s)-3-[(2r,3r,8s)-5-hydroxy-2,3-dimethyl-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-8-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-6-yl]hexanoic acid

C32H46O6 (526.3294)

(2r,3r,4s)-2,3,10,10-tetramethyl-6-oxo-8-phenyl-3,4-dihydro-2h-1,5,9-trioxatriphenylen-4-yl acetate

C27H26O6 (446.1729)

3-[(2r,3r)-5-hydroxy-2,3-dimethyl-8-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-8-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-6-yl]-3-phenylpropanoic acid

C35H44O6 (560.3138)

(10r,11r,12s)-12-(4-bromobenzoyl)-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C32H27BrO5 (570.1042)

(3r)-3-[(2r,3r,6r)-6-{[(1s,3s)-2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl]methyl}-5-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-8-yl]hexanoic acid

C32H46O6 (526.3294)

(2r,3r)-7,9-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-3-(hydroxymethyl)-12-methoxy-2,3-dihydro-1,4,5-trioxatetraphen-10-one

C25H22O11 (498.1162)

1-{6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(2-methylbutanoyl)-2-oxochromen-4-yl}propyl acetate

C29H38O7 (498.2617)

(5r,15s,16r,17r)-15-hydroxy-4,4,16,17-tetramethyl-9-phenyl-6,12,18-trioxapentacyclo[12.4.0.0²,⁷.0³,⁵.0⁸,¹³]octadeca-1,7,9,13-tetraen-11-one

C25H24O5 (404.1624)

5,9-dihydroxy-10-methoxy-1,1,2-trimethyl-7-(3-methylbut-2-en-1-yl)-2h-furo[2,3-c]xanthen-6-one

C24H26O6 (410.1729)

1,3,6-trihydroxy-2-[(2r)-2-hydroxy-3-methylbut-3-en-1-yl]-5-methoxy-7-(3-methylbut-2-en-1-yl)xanthen-9-one

C24H26O7 (426.1678)

6-butanoyl-5-hydroxy-4-phenylfuro[2,3-h]chromen-2-one

C21H16O5 (348.0998)

(2s)-4-hydroxy-2-(2-hydroxypropan-2-yl)-5-[(2s)-2-methylbutanoyl]-9-phenyl-2h,3h-furo[2,3-f]chromen-7-one

C25H26O6 (422.1729)

(6r,7r)-6,7,10,10-tetramethyl-4-phenyl-6,7-dihydro-1,5,9-trioxatriphenylene-2,8-dione

C25H22O5 (402.1467)

6-butanoyl-5-hydroxy-10-(1-hydroxypropyl)-2-methyl-2-(4-methylpent-3-en-1-yl)pyrano[2,3-h]chromen-8-one

C26H32O6 (440.2199)

6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-[(2r)-2-methylbutanoyl]-4-phenylchromen-2-one

C30H34O5 (474.2406)

2-hydroxy-1,8-dimethoxyxanthen-9-one

C15H12O5 (272.0685)

(2s)-4-hydroxy-2-(2-hydroxypropan-2-yl)-9-[(1s)-1-hydroxypropyl]-5-[(2s)-2-methylbutanoyl]-2h,3h-furo[2,3-f]chromen-7-one

C22H28O7 (404.1835)

5-methoxy-2,2-dimethyl-6-(2-methylbut-2-enoyl)-10-propylpyrano[2,3-h]chromen-8-one

C23H26O5 (382.178)

1,5-dihydroxy-6,7-dimethoxyxanthen-9-one

C15H12O6 (288.0634)

(1s,5r,7r)-1-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-6,6-dimethyl-5,7-bis(3-methylbut-2-en-1-yl)bicyclo[3.3.1]nonane-2,4,9-trione

C31H46O3 (466.3447)

(8r,9s)-5-hydroxy-8,9-dimethyl-6-(3-methylbut-2-en-1-yl)-4-phenyl-8h,9h-pyrano[2,3-h]chromene-2,10-dione

C25H24O5 (404.1624)

5,8,9-trihydroxy-2,2-dimethyl-10-(3-methylbut-2-en-1-yl)-1,11-dioxatetracen-6-one

C23H22O6 (394.1416)

(3r)-3-[(7r,8s)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]octanoic acid

C24H32O6 (416.2199)

methyl 3-[(2r,3r)-5-methoxy-2,3-dimethyl-6-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-6-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-8-yl]hexanoate

C34H50O6 (554.3607)

(1s,3as,3br,7s,9as,9bs,11ar)-1-[(2r,5r)-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)

2,3,8-trihydroxy-1,7-dimethoxyxanthen-9-one

C15H12O7 (304.0583)

8-butanoyl-5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-4-phenylchromen-2-one

C24H24O5 (392.1624)

4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

C34H30O7 (550.1991)

methyl (3r)-3-[(7s,8r)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]-3-phenylpropanoate

C26H28O6 (436.1886)

1,3,5-trihydroxy-2-methoxyxanthen-9-one

C14H10O6 (274.0477)

1,3,6-trihydroxy-2-methoxyxanthen-9-one

C14H10O6 (274.0477)

8a-(hydroxymethyl)-4,4a,6b,11,11,12b,14a-heptamethyl-hexadecahydropicen-3-ol

C30H52O2 (444.3967)

1,3,6-trihydroxy-5-methoxy-2,7-bis(3-methylbut-2-en-1-yl)xanthen-9-one

C24H26O6 (410.1729)

6,11-dihydroxy-2,2-dimethyl-12-(2-methylbut-3-en-2-yl)-1,5-dioxatetraphen-10-one

C23H22O5 (378.1467)

8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-4-(1-hydroxypropyl)-6-(3-methylbutanoyl)chromen-2-one

C27H36O6 (456.2512)

(2s)-5,9-dihydroxy-10-methoxy-1,1,2-trimethyl-7-(3-methylbut-2-en-1-yl)-2h-furo[2,3-c]xanthen-6-one

C24H26O6 (410.1729)

(3r)-3-[(2r,3r,6s)-6-decyl-5-hydroxy-2,3-dimethyl-4,7-dioxo-6-pentyl-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid

C35H50O6 (566.3607)

(2r,4r,4ar,6as,6br,8as,12as,12bs,14as,14br)-2-hydroxy-8a-(hydroxymethyl)-4,4a,6b,11,11,12b,14a-heptamethyl-tetradecahydro-1h-picen-3-one

C30H50O3 (458.376)

(3r)-3-[(2r,3s)-5-hydroxy-7-methoxy-2,3-dimethyl-8-(3-methylbut-2-en-1-yl)-4-oxo-2,3-dihydro-1-benzopyran-6-yl]hexanoic acid

C23H32O6 (404.2199)

5,9,10-trihydroxy-2,2-dimethyl-8,12-bis(3-methylbut-2-en-1-yl)-1,11-dioxatetracen-6-one

C28H30O6 (462.2042)

5-hydroxy-6-[(2r)-2-methylbutanoyl]-4-phenylfuro[2,3-h]chromen-2-one

C22H18O5 (362.1154)

(8r,9r)-5-methoxy-8,9-dimethyl-6-(3-methylbut-2-en-1-yl)-4-phenyl-8h,9h-pyrano[2,3-h]chromene-2,10-dione

C26H26O5 (418.178)

5,7-dihydroxy-8-(3-methylbutanoyl)-4-pentylchromen-2-one

C19H24O5 (332.1624)

canophyllol

C30H50O2 (442.3811)

(2s)-5,9,10-trihydroxy-1,1,2-trimethyl-2h-furo[2,3-c]xanthen-6-one

C18H16O6 (328.0947)

methyl 3-[(2r,3r)-6-{[2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl]methyl}-5-methoxy-2,3-dimethyl-6-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-8-yl]nonanoate

C37H56O6 (596.4077)

5-hydroxy-8-methyl-8-(4-methylpent-3-en-1-yl)-6-(2-methylpropanoyl)-4-phenylpyrano[2,3-f]chromen-2-one

C29H30O5 (458.2093)

(2s)-4-{5-hydroxy-8,8-dimethyl-2-oxo-4-propylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl (2e)-3-phenylprop-2-enoate

C31H32O7 (516.2148)

12-methoxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C23H28O5 (384.1937)

6,8-dihydroxy-1,1,7-tris(3-methylbut-2-en-1-yl)xanthene-2,9-dione

C28H32O5 (448.225)

(3r)-3-[(7r,8s)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]hexanoic acid

C22H28O6 (388.1886)

6,11-dihydroxyfuro[3,2-b]xanthen-5-one

C15H8O5 (268.0372)

3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1,12-dioxatetraphen-7-one

C18H16O5 (312.0998)

5,7-dihydroxy-4-[(1s)-1-hydroxypropyl]-6-(3-methylbut-2-en-1-yl)-8-(2-methylpropanoyl)chromen-2-one

C21H26O6 (374.1729)

6-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-8-(3-methylbutanoyl)-4-phenylchromen-2-one

C30H34O5 (474.2406)

3-[(2s,3r)-7-hydroxy-2,3-dimethyl-6-(3-methylbut-3-en-1-yl)-6-(2-methylprop-1-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid

C29H34O6 (478.2355)

(8r)-5-hydroxy-8-methyl-8-(4-methylpent-3-en-1-yl)-6-(2-methylpropanoyl)-4-phenylpyrano[2,3-f]chromen-2-one

C29H30O5 (458.2093)

(3s,4as,6ar,6bs,8ar,11r,12s,12as,14ar,14br)-4,4,6a,6b,8a,11,12,14b-octamethyl-2,3,4a,5,6,7,8,9,10,11,12,12a,14,14a-tetradecahydro-1h-picen-3-ol

C30H50O (426.3861)

6-hydroxy-1,2-dimethoxyxanthen-9-one

C15H12O5 (272.0685)

5-hydroxy-7,8-dimethyl-10-(3-methylbut-2-en-1-yl)-4-phenyl-7h,8h-pyrano[3,2-g]chromene-2,6-dione

C25H24O5 (404.1624)

(3r)-3-[(2s,3r,6r)-5-hydroxy-2,3-dimethyl-6-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-5-en-1-yl]-6-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-8-yl]hexanoic acid

C32H46O6 (526.3294)

(5r,5as,7as,7br,9as,13as,13bs,15ar,15bs)-9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one

C30H50O3 (458.376)

3-[(7r,8r)-2,2,7,8-tetramethyl-6h,7h,8h-pyrano[3,2-g]chromen-10-yl]heptanoic acid

C23H32O4 (372.23)

(3s)-3-[(2r,3s,8s)-5-hydroxy-2,3-dimethyl-8-[(2s)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-8-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-6-yl]-3-phenylpropanoic acid

C35H44O6 (560.3138)

(10r,11r,12s)-12-hydroxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C25H24O5 (404.1624)

(3r)-3-[(2s,3r)-5-hydroxy-2,3,8,8-tetramethyl-4-oxo-2h,3h-pyrano[2,3-f]chromen-6-yl]hexanoic acid

C22H28O6 (388.1886)

(3r)-3-[(2r,3r,6s)-4-hydroxy-2,3-dimethyl-6-[(2r)-5-methyl-2-(2-methylprop-1-en-1-yl)hex-5-en-1-yl]-6-(3-methylbut-2-en-1-yl)-5,7-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid

C36H46O6 (574.3294)

4-[5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-2-oxo-4-phenylchromen-6-yl]-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

C34H32O7 (552.2148)

(3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]-3-phenylpropanoic acid

C35H46O6 (562.3294)

1,3,7-trihydroxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one

C18H16O5 (312.0998)

8-hydroxy-1,2-dimethoxyxanthen-9-one

C15H12O5 (272.0685)

3a,5a,5b,8,8,11a-hexamethyl-1-(prop-1-en-2-yl)-tetradecahydro-1h-cyclopenta[a]chrysen-9-one

C30H48O (424.3705)

(1r)-1-[5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-8-(2-methylpropanoyl)-2-oxochromen-4-yl]propyl acetate

C23H28O7 (416.1835)

(2s)-4-{5-hydroxy-8,8-dimethyl-2-oxo-4-phenylpyrano[2,3-f]chromen-6-yl}-2-methyl-4-oxobutyl (2e)-3-phenylprop-2-enoate

C34H30O7 (550.1991)

1,3,6,8-tetrahydroxy-2-methoxyxanthen-9-one

C14H10O7 (290.0427)

10-butanoyl-5-hydroxy-4-(1-hydroxypropyl)-8,8-dimethylpyrano[3,2-g]chromen-2-one

C21H24O6 (372.1573)

4,4,16,17-tetramethyl-9-phenyl-6,12,18-trioxapentacyclo[12.4.0.0²,⁷.0³,⁵.0⁸,¹³]octadeca-1,7,9,13-tetraene-11,15-dione

C25H22O5 (402.1467)

epicholestrol

C27H46O (386.3548)

(2s)-9-[(2r)-butan-2-yl]-4-hydroxy-5-[(3s)-4-hydroxy-3-methylbutanoyl]-2-(2-hydroxypropan-2-yl)-2h,3h-furo[2,3-f]chromen-7-one

C23H30O7 (418.1991)

5-hydroxy-6-(4-hydroxy-3-methylbutanoyl)-8,8-dimethyl-4-phenylpyrano[2,3-f]chromen-2-one

C25H24O6 (420.1573)

2,3,4-trimethoxyxanthen-9-one

C16H14O5 (286.0841)

(3r)-3-[(2r,3s,8r)-5-hydroxy-2,3-dimethyl-8-[(2r)-5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-8-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-6-yl]hexanoic acid

C32H46O6 (526.3294)

5,7-dihydroxy-4-(1-hydroxypropyl)-6-(3-methylbut-2-en-1-yl)-8-(2-methylbutanoyl)chromen-2-one

C22H28O6 (388.1886)

3,4-dihydroxy-2,2-dimethyl-3,4-dihydro-1,12-dioxatetraphen-7-one

C18H16O5 (312.0998)

(1r,5r,9r,11s)-9-benzoyl-5-hydroperoxy-4,4,10,10-tetramethyl-1,11-bis(3-methylbut-2-en-1-yl)-3-oxatricyclo[7.3.1.0²,⁷]tridec-2(7)-ene-8,13-dione

C33H42O6 (534.2981)

3-{5-hydroxy-2,3-dimethyl-8-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-8-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-6-yl}hexanoic acid

C32H46O6 (526.3294)

(2r,4r,4ar,6as,6br,8ar,12ar,12bs,14as,14br)-2-hydroxy-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-3-one

C30H50O2 (442.3811)

5,7-dihydroxy-4-[(1s)-1-hydroxypropyl]-8-(3-methylbut-2-en-1-yl)-6-(3-methylbutanoyl)chromen-2-one

C22H28O6 (388.1886)

8-[(2r,3s)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxychromen-4-one

C30H20O12 (572.0955)

12-hydroxy-4,6,6,10,11-pentamethyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C20H22O5 (342.1467)

5,7-dihydroxy-4-(1-hydroxypropyl)-6-(3-methylbut-2-en-1-yl)-8-(3-methylbutanoyl)chromen-2-one

C22H28O6 (388.1886)

(3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid

C32H48O6 (528.3451)

3-{5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl}-3-phenylpropanoic acid

C25H26O6 (422.1729)

10-hydroxy-7-(2-hydroxypropan-2-yl)-17,17-dimethyl-2,6,18-trioxapentacyclo[11.8.0.0³,¹¹.0⁵,⁹.0¹⁴,¹⁹]henicosa-1(21),3,5(9),10,13,15,19-heptaen-12-one

C23H22O6 (394.1416)

5-hydroxy-6-[(2r,3s)-3-hydroxy-2-methylbutanoyl]-2,2-dimethyl-10-phenyl-9h,10h-pyrano[2,3-h]chromen-8-one

C25H26O6 (422.1729)

(8s)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-(2-methylpropanoyl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one

C24H24O6 (408.1573)

(8r)-5-hydroxy-8-(2-hydroxypropan-2-yl)-6-[(2r)-2-methylbutanoyl]-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one

C25H26O6 (422.1729)

4-{5-hydroxy-8,8-dimethyl-2-oxo-4-propylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

C31H32O7 (516.2148)

12-hydroxy-6,6,10,11-tetramethyl-4-(sec-butyl)-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C23H28O5 (384.1937)

(3r)-3-[(7s,8s)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]hexanoic acid

C22H28O6 (388.1886)

(5s,6s)-5,9,14-trihydroxy-6-(2-hydroxypropan-2-yl)-18,18-dimethyl-2,7,19-trioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁵,²⁰]henicosa-1(21),3,8,10,13,15(20),16-heptaen-12-one

C23H22O8 (426.1315)

6,8-dihydroxy-1,1,7-tris(3-methylbut-2-en-1-yl)-3,4-dihydroxanthene-2,9-dione

C28H34O5 (450.2406)

2-hydroxy-9-xanthenone

C13H8O3 (212.0473)

methyl 3-[(2r,3r)-5-methoxy-2,3-dimethyl-6-[5-methyl-2-(prop-1-en-2-yl)hex-5-en-1-yl]-6-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-8-yl]hexanoate

C34H50O6 (554.3607)

(10r)-5-hydroxy-6-[(2r,3s)-3-hydroxy-2-methylbutanoyl]-2,2,10-trimethyl-9h,10h-pyrano[2,3-h]chromen-8-one

C20H24O6 (360.1573)

1,3-dihydroxy-2,8-bis(3-methylbut-2-en-1-yl)-7-[(2-methylbut-3-en-2-yl)oxy]xanthen-9-one

C28H32O5 (448.225)

3-(6-decyl-5-hydroxy-2,3-dimethyl-4,7-dioxo-6-pentyl-2,3-dihydro-1-benzopyran-8-yl)-3-phenylpropanoic acid

C35H50O6 (566.3607)

1,8-dihydroxy-3-methyl-6-[(3-methylbut-2-en-1-yl)oxy]xanthen-9-one

C19H18O5 (326.1154)

(2,2,6a,8a,9,12b,14a-heptamethyl-10-oxo-tetradecahydro-1h-picen-4a-yl)methyl acetate

C32H52O3 (484.3916)

(1r,2s,4as,4br,6as,10as,10bs,12as)-1-(2-carboxyethyl)-2-ethyl-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysene-6a-carboxylic acid

C30H50O4 (474.3709)

6,8-dihydroxy-1,1-bis(3-methylbut-2-en-1-yl)-3,4-dihydroxanthene-2,9-dione

C23H26O5 (382.178)

(1s)-1-[5-hydroxy-2,2-dimethyl-6-(3-methylbutanoyl)-8-oxopyrano[2,3-f]chromen-10-yl]propyl acetate

C24H28O7 (428.1835)

2,7-dihydroxy-1-methoxyxanthen-9-one

C14H10O5 (258.0528)

5,9-dihydroxy-7-[(2s)-2-hydroxy-3-methylbut-3-en-1-yl]-10-methoxy-1,1,2,2-tetramethylfuro[2,3-c]xanthen-6-one

C25H28O7 (440.1835)

(1s,5s,9s,11r)-9-benzoyl-5-hydroperoxy-4,4,10,10-tetramethyl-1,11-bis(3-methylbut-2-en-1-yl)-3-oxatricyclo[7.3.1.0²,⁷]tridec-2(7)-ene-8,13-dione

C33H42O6 (534.2981)

(2r,3s)-5-hydroxy-2,3,8,8-tetramethyl-6-(1-phenylethenyl)-2h,3h-pyrano[2,3-f]chromen-4-one

C24H24O4 (376.1675)

(3r)-3-[(2r,3r)-5-hydroxy-2,3,8,8-tetramethyl-4-oxo-2h,3h-pyrano[2,3-f]chromen-6-yl]octanoic acid

C24H32O6 (416.2199)

3-[(2s,3r)-6-{[(1s,3s)-2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl]methyl}-7-hydroxy-2,3-dimethyl-6-(3-methylbut-2-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid

C35H44O6 (560.3138)

2-(2-butoxy-2-oxoethyl)-2-hydroxybutanedioic acid

C10H16O7 (248.0896)

(2r,3r,4r)-2,3,10,10-tetramethyl-6-oxo-8-phenyl-3,4-dihydro-2h-1,5,9-trioxatriphenylen-4-yl acetate

C27H26O6 (446.1729)

12-methoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C26H26O5 (418.178)

(1as,4s,7br)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol

C15H26O (222.1984)

(2s)-4-hydroxy-2-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-5-(3-methylbutanoyl)-9-phenyl-2h,3h-furo[2,3-f]chromen-7-one

C30H34O6 (490.2355)

5,6-dihydroxy-1,3-dimethoxyxanthen-9-one

C15H12O6 (288.0634)

3-{5-hydroxy-2,3,8,8-tetramethyl-4-oxo-2h,3h-pyrano[2,3-f]chromen-10-yl}hexanoic acid

C22H28O6 (388.1886)

6-butanoyl-8-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-4-[(1s)-1-hydroxypropyl]chromen-2-one

C26H34O6 (442.2355)

(4r,4ar,6as,6br,8as,12as,12bs,14as,14br)-8a-(hydroxymethyl)-4,4a,6b,11,11,12b,14a-heptamethyl-tetradecahydro-1h-picen-3-one

C30H50O2 (442.3811)

(4as,10r,11s,12br)-6,6,10,11-tetramethyl-4-phenyl-4a,10,11,12b-tetrahydro-1,5,9-trioxatriphenylene-2,12-dione

C25H24O5 (404.1624)

methyl 7-methoxy-9-oxoxanthene-3-carboxylate

C16H12O5 (284.0685)

1-hydroxy-2-methoxyxanthen-9-one

C14H10O4 (242.0579)

(4r,4as,6as,6bs,8ar,12ar,12bs,14as,14bs)-4,4a,6b,8a,11,11,12b,14a-octamethyl-tetradecahydro-1h-picen-3-one

C30H50O (426.3861)

12-[(2s)-2-hydroperoxy-3-methylbut-3-en-1-yl]-5,8-dihydroxy-2,2-dimethyl-1,11-dioxatetracen-6-one

C23H22O7 (410.1365)

6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-8-(2-methylpropanoyl)-4-phenylchromen-2-one

C29H32O5 (460.225)

(2s)-4-{5-hydroxy-2,2-dimethyl-8-oxo-10-phenylpyrano[2,3-h]chromen-6-yl}-2-methyl-4-oxobutyl (2e)-3-phenylprop-2-enoate

C34H30O7 (550.1991)

2-bromo-4-[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]benzene-1,3,5-triol

C13H9Br3O5 (481.8)

5-hydroxy-8-(2-methoxypropan-2-yl)-6-(2-methylbutanoyl)-4-phenylfuro[2,3-h]chromen-2-one

C26H26O6 (434.1729)

3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(2-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]hexanoic acid

C32H48O6 (528.3451)

8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(3-methylbutanoyl)-4-phenylchromen-2-one

C30H34O5 (474.2406)

9a-(hydroxymethyl)-5,5a,7b,12,12,13b,15a-heptamethyl-tetradecahydro-1h-chryseno[2,1-c]oxepin-3-one

C30H50O3 (458.376)

methyl 3-{5-hydroxy-2,3-dimethyl-8-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-8-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-6-yl}-3-phenylpropanoate

C36H46O6 (574.3294)

5,7-dihydroxy-8-[(3s)-4-hydroxy-3-methylbutanoyl]-6-(3-methylbut-2-en-1-yl)-4-phenylchromen-2-one

C25H26O6 (422.1729)

4-{5-hydroxy-8,8-dimethyl-2-oxo-4-phenylpyrano[2,3-f]chromen-6-yl}-2-methyl-4-oxobutyl 3-phenylprop-2-enoate

C34H30O7 (550.1991)

1-hydroxy-7-methoxy-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}xanthen-9-one

C20H20O10 (420.1056)

5-hydroxy-10-[(1s)-1-hydroxypropyl]-2,2-dimethyl-6-(3-methylbutanoyl)pyrano[2,3-f]chromen-8-one

C22H26O6 (386.1729)

5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-6-[(2r)-2-methylbutanoyl]-4-propylchromen-2-one

C22H28O5 (372.1937)

3-(6-{[2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl]methyl}-5-hydroxy-2,3-dimethyl-6-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-8-yl)-3-phenylpropanoic acid

C35H44O6 (560.3138)

14a-[(acetyloxy)methyl]-10-hydroxy-2,2,6a,8a,9,12b-hexamethyl-hexadecahydropicene-4a-carboxylic acid

C32H52O5 (516.3815)

22-hydroxy-7,7,18,18-tetramethyl-8,13,17-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3,5,9,11,14,16(21),19-octaen-2-one

C23H20O5 (376.1311)

(1r,3ar,3br,7s,9ar,9br,11ar)-1-[(2r,5r)-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)

8-benzoyl-7-hydroxy-5-methoxy-4-phenylchromen-2-one

C23H16O5 (372.0998)

4-hydroxy-2-(2-hydroxy-5-methylhexan-2-yl)-2-methyl-5-(3-methylbutanoyl)-9-phenyl-3h-furo[2,3-f]chromen-7-one

C30H36O6 (492.2512)

10-benzoyl-5-hydroxy-8,8-dimethyl-4-phenylpyrano[3,2-g]chromen-2-one

C27H20O5 (424.1311)

5-hydroxy-6-(1-hydroxy-2-oxo-1-phenylpropyl)-2,3-dimethyl-8-[5-methyl-2-(propan-2-ylidene)hex-4-en-1-yl]-8-(3-methylbut-2-en-1-yl)-2,3,4a,8a-tetrahydro-1-benzopyran-4,7-dione

C35H46O6 (562.3294)

5-hydroxy-6-(3-methylbutanoyl)-4-phenyl-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one

C25H24O5 (404.1624)

3-[(2r,3s)-6-{[(1s,3s)-2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl]methyl}-7-hydroxy-2,3-dimethyl-6-(3-methylbut-2-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]-3-phenylpropanoic acid

C35H44O6 (560.3138)

(10r,11r,12s)-12-methoxy-6,6,10,11-tetramethyl-4-propyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C23H28O5 (384.1937)

(2r)-2-[(1e)-dec-1-en-1-yl]tetradecanoic acid

C24H46O2 (366.3498)

5,8,9-trihydroxy-2,2-dimethyl-1,11-dioxatetracen-6-one

C18H14O6 (326.079)

(3r)-3-[(7r,8r)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]hexanoic acid

C22H28O6 (388.1886)

6,8-dihydroxy-1,1-bis(3-methylbut-2-en-1-yl)xanthene-2,9-dione

C23H24O5 (380.1624)

3-(6-{[2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl]methyl}-4-hydroxy-2,3-dimethyl-6-(3-methylbut-2-en-1-yl)-5,7-dioxo-2,3-dihydro-1-benzopyran-8-yl)-3-phenylpropanoic acid

C35H44O6 (560.3138)

(2s)-2-[(1e)-2-(1,3-dihydroxy-5-methoxy-9-oxoxanthen-2-yl)ethenyl]-7,9-dihydroxy-12-methoxy-2-methyl-3h-1,4,5-trioxatetraphen-10-one

C33H24O12 (612.1268)

(2r)-5-hydroxy-2-methyl-6-[(2r)-2-methylbutanoyl]-2-(4-methylpent-3-en-1-yl)-10-phenylpyrano[2,3-h]chromen-8-one

C30H32O5 (472.225)

(2r)-4-hydroxy-2-(2-hydroxypropan-2-yl)-5-(2-methylpropanoyl)-9-phenyl-2h,3h-furo[2,3-f]chromen-7-one

C24H24O6 (408.1573)

5-benzoyl-4-hydroxy-2-(2-hydroxypropan-2-yl)-9-phenyl-2h,3h-furo[2,3-f]chromen-7-one

C27H22O6 (442.1416)

7-hydroxy-4-(4-hydroxyphenyl)-6,8-dimethoxychromen-2-one

C17H14O6 (314.079)

6-butanoyl-5,7-dihydroxy-8-[(2r)-2-hydroxy-3-methylbut-3-en-1-yl]-4-phenylchromen-2-one

C24H24O6 (408.1573)

8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-6-(2-methylbutanoyl)-4-phenylchromen-2-one

C30H34O5 (474.2406)

4-hydroxy-5-(3-methylbutanoyl)-9-phenylfuro[2,3-f]chromen-7-one

C22H18O5 (362.1154)

2,8-dihydroxy-1-methoxyxanthen-9-one

C14H10O5 (258.0528)

5,7-dihydroxy-8-(2-hydroxy-3-methylbut-3-en-1-yl)-6-(2-methylbutanoyl)-4-phenylchromen-2-one

C25H26O6 (422.1729)

1,5-dihydroxy-6-[(3s)-4-hydroxy-3-methylbutyl]xanthen-9-one

C18H18O5 (314.1154)

1-hydroxy-5-methoxyxanthen-9-one

C14H10O4 (242.0579)

8-butanoyl-5,7-dihydroxy-4-[(1s)-1-hydroxypropyl]-6-(3-methylbut-2-en-1-yl)chromen-2-one

C21H26O6 (374.1729)

(3s,4ar,6ar,8ar,12ar,12bs,14as,14br)-4,4,6a,8a,11,11,12b,14b-octamethyl-1,2,3,4a,5,6,8,9,10,12,12a,13,14,14a-tetradecahydropicen-3-ol

C30H50O (426.3861)

(10r,11s,12r)-12-methoxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C26H26O5 (418.178)

1,5-dihydroxy-6-methoxyxanthen-9-one

C14H10O5 (258.0528)

22-hydroxy-6,6,18,18-tetramethyl-15-(3-methylbut-2-en-1-yl)-5,13,17-trioxapentacyclo[12.8.0.0³,¹².0⁴,⁹.0¹⁶,²¹]docosa-1(22),3,7,9,11,14,16(21),19-octaen-2-one

C28H28O5 (444.1937)

methyl (3r)-3-[(7s,8r)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]hexanoate

C23H30O6 (402.2042)

(8s)-5-hydroxy-6-(3-methylbutanoyl)-4-phenyl-8-(prop-1-en-2-yl)-8h,9h-furo[2,3-h]chromen-2-one

C25H24O5 (404.1624)

10-hydroxy-2,2,6a,8a,9,12b,14a-heptamethyl-hexadecahydropicene-4a-carboxylic acid

C30H50O3 (458.376)

5,7-dihydroxy-8-(3-methylbutanoyl)-4-phenylchromen-2-one

C20H18O5 (338.1154)

(4as,6ar,6bs,8as,9r,12as,12bs,14as,14bs)-2,2,6a,8a,9,12b,14a-heptamethyl-10-oxo-tetradecahydro-1h-picene-4a-carbaldehyde

C30H48O2 (440.3654)

3-(6-{[2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl]methyl}-7-hydroxy-2,3-dimethyl-6-(3-methylbut-2-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl)hexanoic acid

C32H46O6 (526.3294)

(2z)-3-{7-hydroxy-5-methoxy-2,2-dimethyl-6-[(2e)-2-methylbut-2-enoyl]chromen-8-yl}-3-phenylprop-2-enoic acid

C26H26O6 (434.1729)

(3r)-3-[(7r,8s)-5-hydroxy-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]butanoic acid

C20H24O6 (360.1573)

4,4-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)-5-(2-methylbutanoyl)-6-oxabicyclo[3.2.1]octane-7,8-dione

C24H36O4 (388.2613)

(2r)-6-{[(2r)-2,8-dimethyl-2-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-1-benzopyran-6-yl]peroxy}-2,8-dimethyl-2-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-1-benzopyran

C54H78O4 (790.59)

(6s,7s)-6,7,10,10-tetramethyl-4-propyl-6,7-dihydro-1,5,9-trioxatriphenylene-2,8-dione

C22H24O5 (368.1624)

1-hydroxy-5,6-dimethoxyxanthen-9-one

C15H12O5 (272.0685)

2,6-dihydroxy-1,8-dimethoxyxanthen-9-one

C15H12O6 (288.0634)

5,9,10-trihydroxy-1,1,2-trimethyl-2h-furo[2,3-c]xanthen-6-one

C18H16O6 (328.0947)

3,8-dihydroxy-1,2,4-trimethoxyxanthen-9-one

C16H14O7 (318.0739)

3-{7-hydroxy-2,3-dimethyl-6-[5-methyl-2-(prop-1-en-2-yl)hex-5-en-1-yl]-6-(3-methylbut-2-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl}hexanoic acid

C32H46O6 (526.3294)

methyl 3-[(2r,3r)-6-{[2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl]methyl}-5-methoxy-2,3-dimethyl-6-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-8-yl]hexanoate

C34H50O6 (554.3607)

10-butanoyl-5-hydroxy-4-[(1s)-1-hydroxypropyl]-8,8-dimethylpyrano[2,3-f]chromen-2-one

C21H24O6 (372.1573)

4-hydroxy-2-(2-hydroxy-6-methylhept-5-en-2-yl)-5-(3-methylbutanoyl)-9-phenyl-2h,3h-furo[2,3-f]chromen-7-one

C30H34O6 (490.2355)

5-hydroxy-8-(2-methoxypropan-2-yl)-6-[(2r)-2-methylbutanoyl]-4-phenylfuro[2,3-h]chromen-2-one

C26H26O6 (434.1729)

3-[2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-(3-methylbutanoyl)-4-oxo-5,6-dihydrochromen-8-yl]-3-phenylpropanoic acid

C35H46O6 (562.3294)

(1as,4s,7r,7br)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-ol

C15H26O (222.1984)

7-[(2s)-2,3-dihydroxy-3-methylbutyl]-5,9-dihydroxy-10-methoxy-1,1,2,2-tetramethylfuro[2,3-c]xanthen-6-one

C25H30O8 (458.1941)

5-hydroxy-8,8-dimethyl-6-[(2r)-2-methylbutanoyl]-4-phenylpyrano[2,3-f]chromen-2-one

C25H24O5 (404.1624)

(10s,11r,12s)-12-hydroxy-4,6,6,10,11-pentamethyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C20H22O5 (342.1467)

(2r)-4-(4-methoxy-9-oxoxanthen-3-yl)-2-methylbutanoic acid

C19H18O5 (326.1154)

(10r,11s,12s)-12-hydroxy-4,6,6,10,11-pentamethyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C20H22O5 (342.1467)

8-[5-(5,7-dihydroxy-4-oxochromen-2-yl)-2-hydroxyphenyl]-5,7-dihydroxy-6-(2-hydroxy-3-methylbut-3-en-1-yl)-2-(4-hydroxyphenyl)chromen-4-one

C35H26O11 (622.1475)

5-methoxy-2,2,10-trimethyl-6-[(2e)-2-methylbut-2-enoyl]pyrano[2,3-h]chromen-8-one

C21H22O5 (354.1467)

methyl 3-(6-{[2,2-dimethyl-3-(prop-1-en-2-yl)cyclobutyl]methyl}-5-methoxy-2,3-dimethyl-6-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-8-yl)nonanoate

C37H56O6 (596.4077)

3-[(2r,3r)-5-hydroxy-2,3-dimethyl-8-[5-methyl-2-(prop-1-en-2-yl)hex-4-en-1-yl]-8-(3-methylbut-2-en-1-yl)-4,7-dioxo-2,3-dihydro-1-benzopyran-6-yl]hexanoic acid

C32H46O6 (526.3294)

(3r)-3-[(7r,8s)-5-(acetyloxy)-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]hexanoic acid

C24H30O7 (430.1991)

(4r,5r,14r)-8-hydroxy-4,5-dimethyl-9-(3-methylbut-2-en-1-yl)-14-propyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-triene-6,12-dione

C22H28O5 (372.1937)

6,8-dihydroxy-2,2-dimethyl-7,9-bis(3-methylbut-2-en-1-yl)-1,10-dioxatetraphen-5-one

C28H30O5 (446.2093)

6-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-4-(1-hydroxypropyl)-8-(2-methylbutanoyl)chromen-2-one

C27H36O6 (456.2512)

8-[(2s,3r)-5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-3-yl]-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one

C30H20O10 (540.1056)

(10r,11r,12s)-12-hydroxy-4-isopropyl-6,6,10,11-tetramethyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C22H26O5 (370.178)

(11s)-6-chloro-11-methyl-10-(3-methylbut-2-en-1-yl)-1,3,10-triazatricyclo[6.4.1.0⁴,¹³]trideca-2,4,6,8(13)-tetraene-2-thiol

C16H20ClN3S (321.1066)

(1s,4r,8s,10r)-8-benzoyl-4-(2-hydroxypropan-2-yl)-9,9-dimethyl-1,10-bis(3-methylbut-2-en-1-yl)-3-oxatricyclo[6.3.1.0²,⁶]dodec-2(6)-ene-7,12-dione

C33H42O5 (518.3032)

5,7-dihydroxy-6-(2-hydroxy-3-methylbut-3-en-1-yl)-8-(2-methylbutanoyl)-4-phenylchromen-2-one

C25H26O6 (422.1729)

3-[(2r,3r)-7-hydroxy-2,3-dimethyl-6,6-bis(3-methylbut-2-en-1-yl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl]hexanoic acid

C27H38O6 (458.2668)

5,10-dihydroxy-2-(2-hydroxypropan-2-yl)-4-methoxy-1h,2h-furo[2,3-c]xanthen-6-one

C19H18O7 (358.1052)

(4r,5s)-8-hydroxy-4,5-dimethyl-9-(3-methylbut-2-en-1-yl)-14-propyl-3,11-dioxatricyclo[8.4.0.0²,⁷]tetradeca-1,7,9-triene-6,12-dione

C22H28O5 (372.1937)

(3s)-3-[(2s,3r)-5-hydroxy-2,3,8,8-tetramethyl-4-oxo-2h,3h-pyrano[2,3-f]chromen-6-yl]heptanoic acid

C23H30O6 (402.2042)

(2r)-4-hydroxy-2-(2-hydroxypropan-2-yl)-5-(3-methylbutanoyl)-9-phenyl-2h,3h-furo[2,3-f]chromen-7-one

C25H26O6 (422.1729)

(2r,3r)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-12-methoxy-2,3-dihydro-1,4,5-trioxatetraphen-10-one

C24H20O8 (436.1158)

(3s)-3-[(4as,6s)-2-hydroxy-7,7-dimethyl-4a,6-bis(3-methylbut-2-en-1-yl)-3-[(2r)-2-methylbutanoyl]-4-oxo-5,6-dihydrochromen-8-yl]-3-phenylpropanoic acid

C35H46O6 (562.3294)

(3s)-3-(5,7-dihydroxy-2,2-dimethyl-3,4-dihydro-1-benzopyran-8-yl)-3-phenylpropanoic acid

C20H22O5 (342.1467)

4-hydroxy-2h-[1,3]dioxolo[4,5-b]xanthen-10-one

C14H8O5 (256.0372)

(3r)-6-methoxy-3,7-dimethyl-3,4-dihydro-1h-2-benzopyran-8-ol

C12H16O3 (208.1099)

2-[(1e)-2-(1,3-dihydroxy-5-methoxy-9-oxoxanthen-2-yl)ethenyl]-7,9-dihydroxy-12-methoxy-2-methyl-3h-1,4,5-trioxatetraphen-10-one

C33H24O12 (612.1268)

9,10-dihydroxy-5-methoxy-2,2-dimethyl-1,11-dioxatetracen-6-one

C19H16O6 (340.0947)

(10s)-5-hydroxy-6-[(2s,3s)-3-hydroxy-2-methylbutanoyl]-10-isopropyl-2,2-dimethyl-9h,10h-pyrano[2,3-h]chromen-8-one

C22H28O6 (388.1886)

(2e)-3-{7-hydroxy-5-methoxy-2,2-dimethyl-6-[(2e)-2-methylbut-2-enoyl]chromen-8-yl}-3-phenylprop-2-enoic acid

C26H26O6 (434.1729)

2,2,4a,6a,8a,9,12b,14a-octamethyl-hexadecahydropicene

C30H52 (412.4069)

(8s)-6-butanoyl-5-hydroxy-8-(2-hydroxypropan-2-yl)-4-phenyl-8h,9h-furo[2,3-h]chromen-2-one

C24H24O6 (408.1573)

1,3,6-trihydroxy-2-(3-methylbut-2-en-1-yl)xanthen-9-one

C18H16O5 (312.0998)

5,7-dihydroxy-8-(3-methylbut-2-en-1-yl)-6-[(2r)-2-methylbutanoyl]-4-pentylchromen-2-one

C24H32O5 (400.225)

6,6,10,11-tetramethyl-4-phenyl-4a,10,11,12b-tetrahydro-1,5,9-trioxatriphenylene-2,12-dione

C25H24O5 (404.1624)

1-[5,7-dihydroxy-6-(3-methylbut-2-en-1-yl)-8-(2-methylpropanoyl)-2-oxochromen-4-yl]propyl acetate

C23H28O7 (416.1835)

1,5-dihydroxy-6-(4-hydroxy-3-methylbutyl)xanthen-9-one

C18H18O5 (314.1154)

2,4,8-trihydroxy-1-methoxyanthracene-9,10-dione

C15H10O6 (286.0477)

1-(2-carboxyethyl)-2-ethyl-2,4b,9,9,10b,12a-hexamethyl-dodecahydrochrysene-6a-carboxylic acid

C30H50O4 (474.3709)

3-{6-[(3e)-3,7-dimethylocta-3,6-dien-1-yl]-7-hydroxy-2,3-dimethyl-6-(3-methylbutyl)-4,5-dioxo-2,3-dihydro-1-benzopyran-8-yl}-3-phenylpropanoic acid

C35H46O6 (562.3294)

6,11-dihydroxy-12-methoxy-2,2-dimethyl-1,5-dioxatetraphen-10-one

C19H16O6 (340.0947)

(10r,11r)-6,6,10,11-tetramethyl-4-phenyl-10,11-dihydro-1,5,9-trioxatriphenylene-2,12-dione

C25H22O5 (402.1467)

2-bromo-4,6-bis[(2,3-dibromo-4,5-dihydroxyphenyl)methyl]benzene-1,3,5-triol

C20H13Br5O7 (759.6578)

(2s,3s)-3,4-dihydroxy-2-(2-hydroxypropan-2-yl)-5-(3-methylbutanoyl)-9-propyl-2h,3h-furo[2,3-f]chromen-7-one

C22H28O7 (404.1835)

8-(3,7-dimethylocta-2,6-dien-1-yl)-5,7-dihydroxy-4-(1-hydroxypropyl)-6-(2-methylbutanoyl)chromen-2-one

C27H36O6 (456.2512)

(10r,11s,12r)-12-hydroxy-6,6,10,11-tetramethyl-4-phenyl-11,12-dihydro-10h-1,5,9-trioxatriphenylen-2-one

C25H24O5 (404.1624)

3-[5-(acetyloxy)-2,2,7,8-tetramethyl-6-oxo-7h,8h-pyrano[3,2-g]chromen-10-yl]hexanoic acid

C24H30O7 (430.1991)

8-butanoyl-5,7-dihydroxy-6-(2-hydroxy-3-methylbut-3-en-1-yl)-4-phenylchromen-2-one

C24H24O6 (408.1573)

5,7,10-trihydroxy-2,2-dimethyl-12-(3-methylbut-2-en-1-yl)-1,11-dioxatetracen-6-one

C23H22O6 (394.1416)

(1s,3s,5s)-4,4-dimethyl-1,3-bis(3-methylbut-2-en-1-yl)-5-[(2s)-2-methylbutanoyl]-6-oxabicyclo[3.2.1]octane-7,8-dione

C24H36O4 (388.2613)

8-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-5,7-dihydroxy-4-[(1s)-1-hydroxypropyl]-6-(3-methylbutanoyl)chromen-2-one

C27H36O6 (456.2512)

2,3-dihydroxy-1-methoxyxanthen-9-one

C14H10O5 (258.0528)

2-hydroxy-1-methoxyxanthen-9-one

C14H10O4 (242.0579)

5-methoxy-2,2-dimethyl-6-[(2e)-2-methylbut-2-enoyl]-10-propylpyrano[2,3-h]chromen-8-one

C23H26O5 (382.178)

1-hydroxy-7-methoxyxanthen-9-one

C14H10O4 (242.0579)

5-hydroxy-2-{3-[5-hydroxy-8-(4-hydroxyphenyl)-2,2-dimethyl-6-oxopyrano[3,2-g]chromen-10-yl]-4-methoxyphenyl}-7-methoxychromen-4-one

C37H28O10 (632.1682)

3-hydroxy-1,5,6-trimethoxyxanthen-9-one

C16H14O6 (302.079)

(11r,15s)-9-hydroxy-14,14-dimethyl-8-(3-methylbutanoyl)-3-propyl-6,12,13,16-tetraoxatetracyclo[8.6.0.0²,⁷.0¹¹,¹⁵]hexadeca-1,3,7,9-tetraen-5-one

C22H26O7 (402.1678)

(3r)-3,8-dihydroxy-2,2-dimethyl-3,4-dihydro-1,12-dioxatetraphen-7-one

C18H16O5 (312.0998)

2,2-dimethyl-6h-1,11-dioxatetracene-5,9,10-triol

C18H16O5 (312.0998)

3-[(2r,3s)-2,3,8,8-tetramethyl-4-oxo-2h,3h-pyrano[2,3-f]chromen-6-yl]hexanoic acid

C22H28O5 (372.1937)

9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid

C30H48O3 (456.3603)

(4as,6ar,6bs,8as,9r,12as,12bs,14ar,14bs)-14a-({[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}methyl)-2,2,6a,8a,9,12b-hexamethyl-10-oxo-tetradecahydro-1h-picene-4a-carboxylic acid

C39H54O6 (618.392)