NCBI Taxonomy: 2870

Fucoxanthin

C42H58O6 (658.4233)

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

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).

linolenate(18:3)

C18H30O2 (278.2246)

alpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. alpha-Linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. α-Linolenic acid can be obtained by humans only through their diets. Humans lack the desaturase enzymes required for processing stearic acid into A-linoleic acid or other unsaturated fatty acids. Dietary α-linolenic acid is metabolized to stearidonic acid, a precursor to a collection of polyunsaturated 20-, 22-, 24-, etc fatty acids (eicosatetraenoic acid, eicosapentaenoic acid, docosapentaenoic acid, tetracosapentaenoic acid, 6,9,12,15,18,21-tetracosahexaenoic acid, docosahexaenoic acid).[12] Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA.[13] Conversion of ALA to DHA is higher in women than in men.[14] α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.[2] In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds). Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. alpha-Linolenic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Linolenic Acid is a natural product found in Prunus mume, Dipteryx lacunifera, and other organisms with data available. Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group. It is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. A fatty acid that is found in plants and involved in the formation of prostaglandins. Seed oils are the richest sources of α-linolenic acid, notably those of hempseed, chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans. α-Linolenic acid is also obtained from the thylakoid membranes in the leaves of Pisum sativum (pea leaves).[3] Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of ALA, evident as sharp resonances in high-resolution carbon-13 NMR spectra.[4] Some studies state that ALA remains stable during processing and cooking.[5] However, other studies state that ALA might not be suitable for baking as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some ALA may also oxidize at baking temperatures. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

4-Hydroxybenzaldehyde

C7H6O2 (122.0368)

4-Hydroxybenzaldehyde, also known as 4-formylphenol or 4-hydroxybenzenecarbonal, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde exists in all living organisms, ranging from bacteria to humans. 4-Hydroxybenzaldehyde is a sweet, almond, and balsam tasting compound. 4-Hydroxybenzaldehyde is found, on average, in the highest concentration within vinegars and oats. 4-Hydroxybenzaldehyde has also been detected, but not quantified, in several different foods, such as cardoons, colorado pinyons, oyster mushrooms, common chokecherries, and potato. This could make 4-hydroxybenzaldehyde a potential biomarker for the consumption of these foods. 4-hydroxybenzaldehyde is a hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. It has a role as a plant metabolite, a mouse metabolite and an EC 1.14.17.1 (dopamine beta-monooxygenase) inhibitor. 4-Hydroxybenzaldehyde is a natural product found in Ficus septica, Visnea mocanera, and other organisms with data available. Occurs naturally combined in many glycosides. Constituent of vanillin. Isol. in free state from opium poppy (Papaver somniferum) A hydroxybenzaldehyde that is benzaldehyde substituted with a hydroxy group at position C-4. 4-Hydroxybenzaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=123-08-0 (retrieved 2024-07-02) (CAS RN: 123-08-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

DL-Mannitol

C6H14O6 (182.079)

D-mannitol appears as odorless white crystalline powder or free-flowing granules. Sweet taste. (NTP, 1992) D-mannitol is the D-enantiomer of mannitol. It has a role as an osmotic diuretic, a sweetening agent, an antiglaucoma drug, a metabolite, an allergen, a hapten, a food bulking agent, a food anticaking agent, a food humectant, a food stabiliser, a food thickening agent, an Escherichia coli metabolite and a member of compatible osmolytes. Mannitol is an osmotic diuretic that is metabolically inert in humans and occurs naturally, as a sugar or sugar alcohol, in fruits and vegetables. Mannitol elevates blood plasma osmolality, resulting in enhanced flow of water from tissues, including the brain and cerebrospinal fluid, into interstitial fluid and plasma. As a result, cerebral edema, elevated intracranial pressure, and cerebrospinal fluid volume and pressure may be reduced. Mannitol may also be used for the promotion of diuresis before irreversible renal failure becomes established; the promotion of urinary excretion of toxic substances; as an Antiglaucoma agent; and as a renal function diagnostic aid. On October 30, 2020, mannitol was approved by the FDA as add-on maintenance therapy for the control of pulmonary symptoms associated with cystic fibrosis in adult patients and is currently marketed for this indication under the name BRONCHITOL® by Chiesi USA Inc. Mannitol is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Mannitol is an Osmotic Diuretic. The mechanism of action of mannitol is as an Osmotic Activity. The physiologic effect of mannitol is by means of Increased Diuresis. Mannitol is a natural product found in Pavetta indica, Scoparia dulcis, and other organisms with data available. Mannitol is a naturally occurring alcohol found in fruits and vegetables and used as an osmotic diuretic. Mannitol is freely filtered by the glomerulus and poorly reabsorbed from the renal tubule, thereby causing an increase in osmolarity of the glomerular filtrate. An increase in osmolarity limits tubular reabsorption of water and inhibits the renal tubular reabsorption of sodium, chloride, and other solutes, thereby promoting diuresis. In addition, mannitol elevates blood plasma osmolarity, resulting in enhanced flow of water from tissues into interstitial fluid and plasma. D-mannitol is a metabolite found in or produced by Saccharomyces cerevisiae. A diuretic and renal diagnostic aid related to sorbitol. It has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. See also: Mannitol; sorbitol (component of); Mannitol; menthol (component of). Mannitol, or hexan-1,2,3,4,5,6-hexol (C6H8(OH)6), is an alcohol and a sugar (sugar alcohol), or a polyol, it is a stereoisomer of sorbitol and is similar to the C5 xylitol. The structure of mannitol is made of a straight chain of six carbon atoms, each of which is substituted with a hydroxyl group. Mannitol is one of the most abundant energy and carbon storage molecules in nature, it is produced by a wide range of organisms such as bacteria, fungi and plants (PMID: 19578847). In medicine, mannitol is used as a diuretic and renal diagnostic aid. Mannitol has little significant energy value as it is largely eliminated from the body before any metabolism can take place. It can be used to treat oliguria associated with kidney failure or other manifestations of inadequate renal function and has been used for determination of glomerular filtration rate. Mannitol is also commonly used as a research tool in cell biological studies, usually to control osmolarity. Mannitol has a tendency to lose a hydrogen ion in aqueous solutions, which causes the solution to become acidic. For this, it is not uncommon to add a weak base, such as sodium bicarbonate, to the solution to adjust its pH. Mannitol is a non-permeating molecule i.e., it cannot cross biological membranes. Mannitol is an osmotic diuretic agent and a weak renal vasodilator. Mannitol is found to be associated with cytochrome c oxidase deficiency and ribose-5-phosphate isomerase deficiency, which are inborn errors of metabolism. Mannitol is also a microbial metabolite found in Aspergillus, Candida, Clostridium, Gluconobacter, Lactobacillus, Lactococcus, Leuconostoc, Pseudomonas, Rhodobacteraceae, Saccharomyces, Streptococcus, Torulaspora and Zymomonas (PMID: 15240312; PMID: 29480337). Mannitol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=85085-15-0 (retrieved 2024-07-01) (CAS RN: 69-65-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Mannitol is obtained by combining D-mannitol with a sample of Lmannitol obtained by reduction of L-mannono-1, Clactone[1]. DL-Mannitol is obtained by combining D-mannitol with a sample of Lmannitol obtained by reduction of L-mannono-1, Clactone[1]. D-Mannitol (Mannitol) is an oral, resistant sugar widely used in the food and pharmaceutical industries to promote the absorption and retention of calcium and magnesium through cecal fermentation, while acting as a osmotic diuretic to reduce tissue edema. D-Mannitol can enhance brown fat formation, improve insulin effect, reduce blood sugar levels, And through the start the β3-adrenergic receptor (β3-AR), PGC1α and PKA induced by means of white fat cells into brown fat cells[1][2][3][4][5][6][7]. D-Mannitol is an osmotic diuretic with weak renal vasodilatory activity. D-Mannitol (Mannitol) is an oral, resistant sugar widely used in the food and pharmaceutical industries to promote the absorption and retention of calcium and magnesium through cecal fermentation, while acting as a osmotic diuretic to reduce tissue edema. D-Mannitol can enhance brown fat formation, improve insulin effect, reduce blood sugar levels, And through the start the β3-adrenergic receptor (β3-AR), PGC1α and PKA induced by means of white fat cells into brown fat cells[1][2][3][4][5][6][7]. D-Mannitol is an osmotic diuretic with weak renal vasodilatory activity.

Hordenine

C10H15NO (165.1154)

Hordenine is a potent phenylethylamine alkaloid with antibacterial and antibiotic properties produced in nature by several varieties of plants in the family Cactacea. The major source of hordenine in humans is beer brewed from barley. Hordenine in urine interferes with tests for morphine, heroin and other opioid drugs. Hordenine is a biomarker for the consumption of beer Hordenine is a phenethylamine alkaloid. It has a role as a human metabolite and a mouse metabolite. Hordenine is a natural product found in Cereus peruvianus, Mus musculus, and other organisms with data available. See also: Selenicereus grandiflorus stem (part of). Alkaloid from Hordeum vulgare (barley) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2289 Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1]. Hordenine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=539-15-1 (retrieved 2024-10-24) (CAS RN: 539-15-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Galactitol

C6H14O6 (182.079)

Galactitol or dulcitol is a sugar alcohol that is a metabolic breakdown product of galactose. Galactose is derived from lactose in food (such as dairy products). When lactose is broken down by the enzyme lactase it produces glucose and galactose. Galactitol has a slightly sweet taste. It is produced from galactose in a reaction catalyzed by aldose reductase. When present in sufficiently high levels, galactitol can act as a metabotoxin, a neurotoxin, and a hepatotoxin. A neurotoxin is a compound that disrupts or attacks neural cells and neural tissue. A hepatotoxin as a compound that disrupts or attacks liver tissue or liver cells. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Chronically high levels of galactitol are associated with at least two inborn errors of metabolism, including galactosemia and galactosemia type II. Galactosemia is a rare genetic metabolic disorder that affects an individuals ability to metabolize the sugar galactose properly. Excess lactose consumption in individuals with galactose intolerance or galactosemia activates aldose reductase to produce galactitol, thus depleting NADPH and leading to lowered glutathione reductase activity. As a result, hydrogen peroxide or other free radicals accumulate causing serious oxidative damage to various cells and tissues. In individuals with galactosemia, the enzymes needed for the further metabolism of galactose (galactose-1-phosphate uridyltransferase) are severely diminished or missing entirely, leading to toxic levels of galactose 1-phosphate, galactitol, and galactonate. High levels of galactitol in infants are specifically associated with hepatomegaly (an enlarged liver), cirrhosis, renal failure, cataracts, vomiting, seizure, hypoglycemia, lethargy, brain damage, and ovarian failure. Galactitol is an optically inactive hexitol having meso-configuration. It has a role as a metabolite, a human metabolite, an Escherichia coli metabolite and a mouse metabolite. Galactitol is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Galactitol is a natural product found in Elaeodendron croceum, Salacia chinensis, and other organisms with data available. Galactitol is a naturally occurring product of plants obtained following reduction of galactose. It appears as a white crystalline powder with a slight sweet taste. It may form in excess in the lens of the eye in galactosemias a deficiency of galactokinase. A naturally occurring product of plants obtained following reduction of GALACTOSE. It appears as a white crystalline powder with a slight sweet taste. It may form in excess in the lens of the eye in GALACTOSEMIAS, a deficiency of GALACTOKINASE. A naturally occurring product of plants obtained following reduction of galactose. It appears as a white crystalline powder with a slight sweet taste.; Dulcitol (or galactitol) is a sugar alcohol, the reduction product of galactose. Galactitol in the urine is a biomarker for the consumption of milk. Galactitol is found in many foods, some of which are elliotts blueberry, italian sweet red pepper, catjang pea, and green bean. An optically inactive hexitol having meso-configuration. COVID info from COVID-19 Disease Map 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. Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose. Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose.

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).

Campesterol

C28H48O (400.3705)

Campesterol is a phytosterol, meaning it is a steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\\\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. -- Wikipedia. Campesterol is a member of phytosterols, a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid and a C28-steroid. It has a role as a mouse metabolite. It derives from a hydride of a campestane. Campesterol is a natural product found in Haplophyllum bucharicum, Bugula neritina, and other organisms with data available. Campesterol is a steroid derivative that is the simplest sterol, characterized by the hydroxyl group in position C-3 of the steroid skeleton, and saturated bonds throughout the sterol structure, with the exception of the 5-6 double bond in the B ring. Campesterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=474-62-4 (retrieved 2024-07-01) (CAS RN: 474-62-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

Stigmasterol

C29H48O (412.3705)

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

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 .

beta-Carotene

C40H56 (536.4382)

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

beta-Elemene

C15H24 (204.1878)

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

beta-Cryptoxanthin

C40H56O (552.4331)

beta-Cryptoxanthin has been isolated from abalone, fish eggs, and many higher plants. beta-Cryptoxanthin is a major source of vitamin A, often second only to beta-carotene, and is present in fruits such as oranges, tangerines, and papayas (PMID: 8554331). Frequent intake of tropical fruits that are rich in beta-cryptoxanthin is associated with higher plasma beta-cryptoxanthin concentrations in Costa Rican adolescents. Papaya intake was the best food predictor of plasma beta-cryptoxanthin concentrations. Subjects that frequently consumed (i.e. greater or equal to 3 times/day) tropical fruits with at least 50 micro g/100 g beta-cryptoxanthin (e.g. papaya, tangerine, orange, watermelon) had twofold the plasma beta-cryptoxanthin concentrations of those with intakes of less than 4 times/week (PMID: 12368412). A modest increase in beta-cryptoxanthin intake, equivalent to one glass of freshly squeezed orange juice per day, is associated with a reduced risk of developing inflammatory disorders such as rheumatoid arthritis (PMID: 16087992). Higher prediagnostic serum levels of total carotenoids and beta-cryptoxanthin were associated with lower smoking-related lung cancer risk in middle-aged and older men in Shanghai, China (PMID: 11440962). Consistent with inhibition of the lung cancer cell growth, beta-cryptoxanthin induced the mRNA levels of retinoic acid receptor beta (RAR-beta) in BEAS-2B cells, although this effect was less pronounced in A549 cells. Furthermore, beta-cryptoxanthin transactivated the RAR-mediated transcription activity of the retinoic acid response element. These findings suggest a mechanism of anti-proliferative action of beta-cryptoxanthin and indicate that beta-cryptoxanthin may be a promising chemopreventive agent against lung cancer (PMID: 16841329). Cryptoxanthin is a natural carotenoid pigment. It has been isolated from a variety of sources including the petals and flowers of plants in the genus Physalis, orange rind, papaya, egg yolk, butter, apples, and bovine blood serum. In a pure form, cryptoxanthin is a red crystalline solid with a metallic lustre. It is freely soluble in chloroform, benzene, pyridine, and carbon disulfide. In the human body, cryptoxanthin is converted into vitamin A (retinol) and is therefore considered a provitamin A. As with other carotenoids, cryptoxanthin is an antioxidant and may help prevent free radical damage to cells and DNA, as well as stimulate the repair of oxidative damage to DNA. Structurally, cryptoxanthin is closely related to beta-carotene, with only the addition of a hydroxyl group. It is a member of the class of carotenoids known as xanthophylls. Beta-cryptoxanthin is a carotenol that exhibits antioxidant activity. It has been isolated from fruits such as papaya and oranges. It has a role as a provitamin A, an antioxidant, a biomarker and a plant metabolite. It derives from a hydride of a beta-carotene. beta-Cryptoxanthin is a natural product found in Hibiscus syriacus, Cladonia gracilis, and other organisms with data available. A mono-hydroxylated xanthophyll that is a provitamin A precursor. See also: Corn (part of). A carotenol that exhibits antioxidant activity. It has been isolated from fruits such as papaya and oranges. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins Cryptoxanthin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=472-70-8 (retrieved 2024-10-31) (CAS RN: 472-70-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Zeaxanthin

C40H56O2 (568.428)

Zeaxanthin is a carotenoid xanthophyll and is one of the most common carotenoid found in nature. It is the pigment that gives corn, saffron, and many other plants their characteristic color. Zeaxanthin breaks down to form picrocrocin and safranal, which are responsible for the taste and aroma of saffron Carotenoids are among the most common pigments in nature and are natural lipid soluble antioxidants. Zeaxanthin is one of the two carotenoids (the other is lutein) that accumulate in the eye lens and macular region of the retina with concentrations in the macula greater than those found in plasma and other tissues. Lutein and zeaxanthin have identical chemical formulas and are isomers, but they are not stereoisomers. The main difference between them is in the location of a double bond in one of the end rings. This difference gives lutein three chiral centers whereas zeaxanthin has two. A relationship between macular pigment optical density, a marker of lutein and zeaxanthin concentration in the macula, and lens optical density, an antecedent of cataractous changes, has been suggested. The xanthophylls may act to protect the eye from ultraviolet phototoxicity via quenching reactive oxygen species and/or other mechanisms. Some observational studies have shown that generous intakes of lutein and zeaxanthin, particularly from certain xanthophyll-rich foods like spinach, broccoli and eggs, are associated with a significant reduction in the risk for cataract (up to 20\\%) and for age-related macular degeneration (up to 40\\%). While the pathophysiology of cataract and age-related macular degeneration is complex and contains both environmental and genetic components, research studies suggest dietary factors including antioxidant vitamins and xanthophylls may contribute to a reduction in the risk of these degenerative eye diseases. Further research is necessary to confirm these observations. (PMID: 11023002). Zeaxanthin has been found to be a microbial metabolite, it can be produced by Algibacter, Aquibacter, Escherichia, Flavobacterium, Formosa, Gramella, Hyunsoonleella, Kordia, Mesoflavibacter, Muricauda, Nubsella, Paracoccus, Siansivirga, Sphingomonas, Zeaxanthinibacter and yeast (https://reader.elsevier.com/reader/sd/pii/S0924224417302571?token=DE6BC6CC7DCDEA6150497AA3E375097A00F8E0C12AE03A8E420D85D1AC8855E62103143B5AE0B57E9C5828671F226801). It is a marker for the activity of Bacillus subtilis and/or Pseudomonas aeruginosa in the intestine. Higher levels are associated with higher levels of Bacillus or Pseudomonas. (PMID: 17555270; PMID: 12147474) Zeaxanthin is a carotenol. It has a role as a bacterial metabolite, a cofactor and an antioxidant. It derives from a hydride of a beta-carotene. Zeaxanthin is a most common carotenoid alcohols found in nature that is involved in the xanthophyll cycle. As a coexistent isomer of lutein, zeaxanthin is synthesized in plants and some micro-organisms. It gives the distinct yellow color to many vegetables and other plants including paprika, corn, saffron and wolfberries. Zeaxanthin is one of the two primary xanthophyll carotenoids contained within the retina of the eye and plays a predominant component in the central macula. It is available as a dietary supplement for eye health benefits and potential prevention of age-related macular degeneration. Zeaxanthin is also added as a food dye. Zeaxanthin is a natural product found in Bangia fuscopurpurea, Erythrobacter longus, and other organisms with data available. Carotenoids found in fruits and vegetables. Zeaxanthin accumulates in the MACULA LUTEA. See also: Saffron (part of); Corn (part of); Lycium barbarum fruit (part of). D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

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].

4-hydroxyphenylacetate

C8H8O3 (152.0473)

p-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-Hydroxy-2-unsubstituted benzenoids are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic.  p-Hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate.  p-Hydroxyphenylacetic acid can be found in numerous foods such as olives, cocoa beans, oats, and mushrooms. p-Hydroxyphenylacetic acid can be found throughout all human tissues and in all biofluids. Within a cell, p-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space. p-Hydroxyphenylacetic acid is also a microbial metabolite produced by Acinetobacter, Clostridium, Klebsiella, Pseudomonas, and Proteus. Higher levels of this metabolite are associated with an overgrowth of small intestinal bacteria from Clostridia species including C. difficile, C. stricklandii, C. lituseburense, C. subterminale, C. putrefaciens, and C. propionicum (PMID: 476929, 12173102). p-Hydroxyphenylacetic acid is detected after the consumption of whole grain. 4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It is functionally related to an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate. 4-Hydroxyphenylacetic acid is a natural product found in Guanomyces polythrix, Forsythia suspensa, and other organisms with data available. 4-Hydroxyphenylacetic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. Constituent of sweet clover (Melilotus officinalis) and yeast Hydroxyphenylacetic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=156-38-7 (retrieved 2024-07-02) (CAS RN: 156-38-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

Phytol

C20H40O (296.3079)

Phytol, also known as trans-phytol or 3,7,11,15-tetramethylhexadec-2-en-1-ol, is a member of the class of compounds known as acyclic diterpenoids. Acyclic diterpenoids are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, phytol is considered to be an isoprenoid lipid molecule. Phytol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Phytol can be found in a number of food items such as salmonberry, rose hip, malus (crab apple), and black raspberry, which makes phytol a potential biomarker for the consumption of these food products. Phytol can be found primarily in human fibroblasts tissue. Phytol is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. In ruminants, the gut fermentation of ingested plant materials liberates phytol, a constituent of chlorophyll, which is then converted to phytanic acid and stored in fats. In shark liver it yields pristane . Phytol is a diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. It has a role as a plant metabolite, a schistosomicide drug and an algal metabolite. It is a diterpenoid and a long-chain primary fatty alcohol. Phytol is a natural product found in Elodea canadensis, Wendlandia formosana, and other organisms with data available. Phytol is an acyclic diterpene alcohol and a constituent of chlorophyll. Phytol is commonly used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. Furthermore, phytol also was shown to modulate transcription in cells via transcription factors PPAR-alpha and retinoid X receptor (RXR). Acyclic diterpene used in making synthetic forms of vitamin E and vitamin K1. Phytol is a natural linear diterpene alcohol which is used in the preparation of vitamins E and K1. It is also a decomposition product of chlorophyll. It is an oily liquid that is nearly insoluble in water, but soluble in most organic solvents. -- Wikipedia. A diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. C1907 - Drug, Natural Product > C28269 - Phytochemical Acquisition and generation of the data is financially supported in part by CREST/JST. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1]. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1].

Geranyl acetate

C12H20O2 (196.1463)

Geranyl acetate is a clear colorless liquid with an odor of lavender. (NTP, 1992) Geranyl acetate is a monoterpenoid that is the acetate ester derivative of geraniol. It has a role as a plant metabolite. It is an acetate ester and a monoterpenoid. It is functionally related to a geraniol. Geranyl acetate is a natural product found in Nepeta nepetella, Xylopia sericea, and other organisms with data available. See also: Lemon oil, cold pressed (part of); Coriander Oil (part of); Java citronella oil (part of). Neryl acetate is found in cardamom. Neryl acetate is found in citrus, kumquat and pummelo peel oils, ginger, cardamon, clary sage, myrtle leaf and myrtle berries. Neryl acetate is a flavouring agent A monoterpenoid that is the acetate ester derivative of geraniol. Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2]. Geranyl acetate, an acyclic monoterpene ester derived from geraniol, is widely used in the cosmetics industry due to its pleasant scent[1]. Geranyl acetate can induces cell apoptosis[2].

Cycloartenol

C30H50O (426.3861)

Cycloartenol is found in alcoholic beverages. Cycloartenol is a constituent of Artocarpus integrifolia fruits and Solanum tuberosum (potato) Cycloartenol is a sterol precursor in photosynthetic organisms and plants. The biosynthesis of cycloartenol starts from the triterpenoid squalene. Its structure is also related to triterpenoid lanosterol Cycloartenol is a pentacyclic triterpenoid, a 3beta-sterol and a member of phytosterols. It has a role as a plant metabolite. It derives from a hydride of a lanostane. Cycloartenol is a natural product found in Euphorbia nicaeensis, Euphorbia boetica, and other organisms with data available. Constituent of Artocarpus integrifolia fruits and Solanum tuberosum (potato)

Benzyl butyl phthalate

C19H20O4 (312.1362)

CONFIDENCE standard compound; INTERNAL_ID 837; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10079; ORIGINAL_PRECURSOR_SCAN_NO 10074 CONFIDENCE standard compound; INTERNAL_ID 837; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10050; ORIGINAL_PRECURSOR_SCAN_NO 10045 CONFIDENCE standard compound; INTERNAL_ID 837; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10050; ORIGINAL_PRECURSOR_SCAN_NO 10048 CONFIDENCE standard compound; INTERNAL_ID 837; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10020; ORIGINAL_PRECURSOR_SCAN_NO 10018 CONFIDENCE standard compound; INTERNAL_ID 837; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 10069; ORIGINAL_PRECURSOR_SCAN_NO 10066 CONFIDENCE standard compound; INTERNAL_ID 837; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9995; ORIGINAL_PRECURSOR_SCAN_NO 9990 CONFIDENCE standard compound; EAWAG_UCHEM_ID 3597 CONFIDENCE standard compound; INTERNAL_ID 8369 D009676 - Noxae > D013723 - Teratogens

Eicosapentaenoic acid

C20H30O2 (302.2246)

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

Dihomo-gamma-linolenic acid

C20H34O2 (306.2559)

8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(n-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acids eicosanoids [HMDB] 8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(n-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acids eicosanoids. Dihomo-γ-linolenic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1783-84-2 (retrieved 2024-07-01) (CAS RN: 1783-84-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

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.

Citrinin

C13H14O5 (250.0841)

Citrinin is a mycotoxin originally isolated from Penicillium citrinum. It has since been found to be produced by a variety of other fungi which are found or used in the production of human foods, such as grain, cheese, sake and red pigments. Citrinin has also been found in commercial red yeast rice supplements, and also in Aspergillus niveus and Aspergillus terreus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987). D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins Citrinin is a mycotoxin which causes contamination in the food and is associated with different toxic effects. Citrinin is usually found together with another nephrotoxic mycotoxin, Ochratoxin A. Citrinin is also reported to possess a broad spectrum of bioactivities, including antibacterial, antifungal, and potential anticancer and neuro-protective effects in vitro[1][2].

Monocrotaline

C16H23NO6 (325.1525)

Hepatotoxin. Causative agent of much seneciosis, e.g. accidental poisoning by S. by weed residues in bread, and characterised by venoocculosive disease Hepatotoxin. Causative agent of much seneciosis, e.g. accidental poisoning by S. by weed residues in bread, and characterised by venoocculosive diseas CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2249 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 131 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 121 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 151 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 141 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 111 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 161 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 171 CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 101 Monocrotaline is an 11-membered macrocyclic pyrrolizidine alkaloid. Monocrotaline inhibits OCT-1 and OCT-2 with IC50s of 36.8 μM and 1.8 mM, respectively. Monocrotaline has antitumor activity and is cytotoxic to hepatocellular carcinoma cells. Monocrotaline is used to induce a model of pulmonary hypertension in rodents. [2][6][8]. Monocrotaline is an 11-membered macrocyclic pyrrolizidine alkaloid. Monocrotaline inhibits OCT-1 and OCT-2 with IC50s of 36.8 μM and 1.8 mM, respectively. Monocrotaline has antitumor activity and is cytotoxic to hepatocellular carcinoma cells. Monocrotaline is used to induce a model of pulmonary hypertension in rodents. [2][6][8].

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].

Glucose

C6H12O6 (180.0634)

Glucose, also known as D-glucose or dextrose, is a member of the class of compounds known as hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moiety. Glucose contains an aldehyde group and is therefore referred to as an aldohexose. The glucose molecule can exist in an open-chain (acyclic) and ring (cyclic) form, the latter being the result of an intramolecular reaction between the aldehyde C atom and the C-5 hydroxyl group to form an intramolecular hemiacetal. In aqueous solution, both forms are in equilibrium and at pH 7 the cyclic one is predominant. Glucose is a neutral, hydrophilic molecule that readily dissolves in water. It exists as a white crystalline powder. Glucose is the primary source of energy for almost all living organisms. As such, it is the most abundant monosaccharide and the most widely used aldohexose in living organisms. When not circulating freely in blood (in animals) or resin (in plants), glucose is stored as a polymer. In plants it is mainly stored as starch and amylopectin and in animals as glycogen. Glucose is produced by plants through the photosynthesis using sunlight, water and carbon dioxide where it is used as an energy and a carbon source Glucose is particularly abundant in fruits and other parts of plants in its free state. Foods that are particularly rich in glucose are honey, agave, molasses, apples (2g/100g), grapes (8g/100g), oranges (8.5g/100g), jackfruit, dried apricots, dates (32 g/100g), bananas (5.8 g/100g), grape juice, sweet corn, Glucose is about 75\\\\% as sweet as sucrose and about 50\\\\% as sweet as fructose. Sweetness is detected through the binding of sugars to the T1R3 and T1R2 proteins, to form a G-protein coupled receptor that is the sweetness receptor in mammals. Glucose was first isolated from raisins in 1747 by the German chemist Andreas Marggraf. It was discovered in grapes by Johann Tobias Lowitz in 1792 and recognized as different from cane sugar (sucrose). Industrially, glucose is mainly used for the production of fructose and in the production of glucose-containing foods. In foods, it is used as a sweetener, humectant, to increase the volume and to create a softer mouthfeel. Various sources of glucose, such as grape juice (for wine) or malt (for beer), are used for fermentation to ethanol during the production of alcoholic beverages. Glucose is found in many plants as glucosides. A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolyzed by purely chemical means or decomposed by fermentation or enzymes. Glucose can be obtained by the hydrolysis of carbohydrates such as milk sugar (lactose), cane sugar (sucrose), maltose, cellulose, and glycogen. Glucose is a building block of the disaccharides lactose and sucrose (cane or beet sugar), of oligosaccharides such as raffinose and of polysaccharides such as starch and amylopectin, glycogen or cellulose. For most animals, while glucose is normally obtained from the diet, it can also be generated via gluconeogenesis. Gluconeogenesis is a metabolic pathway that results in the generation of glucose from certain non-carbohydrate carbon substrates. Gluconeogenesis is a ubiquitous process, present in plants, animals, fungi, bacteria, and other microorganisms. In vertebrates, gluconeogenesis takes place mainly in the liver and, to a lesser extent, in the cortex of the kidneys. In humans the main gluconeogenic precursors are lactate, glycerol (which is a part of the triacylglycerol molecule), alanine and glutamine. B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CA - Tests for diabetes V - Various > V06 - General nutrients > V06D - Other nutrients > V06DC - Carbohydrates COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents CONFIDENCE standard compound; INTERNAL_ID 226 KEIO_ID G002 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS alpha-D-glucose is an endogenous metabolite. alpha-D-glucose is an endogenous metabolite.

Arachidonic acid

C20H32O2 (304.2402)

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

Pentadecanoic acid

C15H30O2 (242.2246)

Pentadecanoic acid, also known as pentadecylic acid or C15:0, 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. Pentadecanoic acid (its ester is called pentadecanoate) is a saturated fatty acid that has 15 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. Pentadecanoic acid is found in plants and ruminants. Many "odd" length long-chain fatty acids, such as pentadecanoic acid, are derived from the consumption of cattle fats (milk and meat). Pentadecanoic acid constitutes 1.05\\\\% of milk fat and 0.43\\\\% of ruminant meat fat. The content of pentadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID: 9701185; PMID: 11238766). A fatty acid of exogenous (primarily ruminant) origin. Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Pentadecanoic acid constitutes 1.05\\\\% of milk fat and 0.43\\\\% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID 9701185; PMID 11238766). Pentadecanoic acid is found in many foods, some of which are common bean, coriander, pepper (c. annuum), and hamburger. CONFIDENCE standard compound; INTERNAL_ID 248 Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone.

D-Xylose

C5H10O5 (150.0528)

Xylose or wood sugar is an aldopentose - a monosaccharide containing five carbon atoms and an aldehyde functional group. It has chemical formula C5H10O5 and is 40\\\\% as sweet as sucrose. Xylose is found in the embryos of most edible plants. The polysaccharide xylan, which is closely associated with cellulose, consists practically entirely of d-xylose. Corncobs, cottonseed hulls, pecan shells, and straw contain considerable amounts of this sugar. Xylose is also found in mucopolysaccharides of connective tissue and sometimes in the urine. Xylose is the first sugar added to serine or threonine residues during proteoglycan type O-glycosylation. Therefore xylose is involved in the biosythetic pathways of most anionic polysaccharides such as heparan sulphate and chondroitin sulphate. In medicine, xylose is used to test for malabsorption by administering a xylose solution to the patient after fasting. If xylose is detected in the blood and/or urine within the next few hours, it has been absorbed by the intestines. Xylose is said to be one of eight sugars which are essential for human nutrition, the others being galactose, glucose, mannose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid. (Wikipedia). Xylose in the urine is a biomarker for the consumption of apples and other fruits. Xylose is a sugar first isolated from wood, and named for it. Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional group. It is the precursor to hemicellulose, one of the main constituents of biomass. D-Xylopyranose is found in flaxseed. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose.

L-Alanine

C3H7NO2 (89.0477)

Alanine (Ala), also known as L-alanine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-alanine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Alanine is found in all organisms ranging from bacteria to plants to animals. It is classified as an aliphatic, non-polar amino acid. In humans, alanine is a non-essential amino acid that can be easily made in the body from either the conversion of pyruvate or the breakdown of the dipeptides carnosine and anserine. Alanine can be also synthesized from branched chain amino acids such as valine, leucine, and isoleucine. Alanine is produced by reductive amination of pyruvate through a two-step process. In the first step, alpha-ketoglutarate, ammonia and NADH are converted by the enzyme known glutamate dehydrogenase to glutamate, NAD+ and water. In the second step, the amino group of the newly-formed glutamate is transferred to pyruvate by an aminotransferase enzyme, regenerating the alpha-ketoglutarate, and converting the pyruvate to alanine. The net result is that pyruvate and ammonia are converted to alanine. In mammals, alanine plays a key role in glucose–alanine cycle between tissues and liver. In muscle and other tissues that degrade amino acids for fuel, amino groups are collected in the form of glutamate by transamination. Glutamate can then transfer its amino group to pyruvate, a product of muscle glycolysis, through the action of alanine aminotransferase, forming alanine and alpha-ketoglutarate. The alanine enters the bloodstream and is transported to the liver. The alanine aminotransferase reaction takes place in reverse in the liver, where the regenerated pyruvate is used in gluconeogenesis, forming glucose which returns to the muscles through the circulation system. Alanine is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (branched-chain amino acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as a regulator of glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine is reduced in both severe hypoglycemia and the ketosis of diabetes. Alanine is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine, and glycine, is an inhibitory neurotransmitter in the brain (http://www.dcnutrition.com/AminoAcids/). L-Alanine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-41-7 (retrieved 2024-07-01) (CAS RN: 56-41-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

Choline

[C5H14NO]+ (104.1075)

Choline is a basic constituent of lecithin that is found in many plants and animal organs. It is important as a precursor of acetylcholine, as a methyl donor in various metabolic processes, and in lipid metabolism. Choline is now considered to be an essential vitamin. While humans can synthesize small amounts (by converting phosphatidylethanolamine to phosphatidylcholine), it must be consumed in the diet to maintain health. Required levels are between 425 mg/day (female) and 550 mg/day (male). Milk, eggs, liver, and peanuts are especially rich in choline. Most choline is found in phospholipids, namely phosphatidylcholine or lecithin. Choline can be oxidized to form betaine, which is a methyl source for many reactions (i.e. conversion of homocysteine into methionine). Lack of sufficient amounts of choline in the diet can lead to a fatty liver condition and general liver damage. This arises from the lack of VLDL, which is necessary to transport fats away from the liver. Choline deficiency also leads to elevated serum levels of alanine amino transferase and is associated with increased incidence of liver cancer. Nutritional supplement. Occurs free and combined in many animal and vegetable foods with highest concentrations found in egg yolk, meat, fish, milk, cereaks and legumes Choline. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=62-49-7 (retrieved 2024-06-29) (CAS RN: 62-49-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Ophthalmic acid

C11H19N3O6 (289.1274)

Ophthalmic acid, also known as ophthalmate, belongs to the class of organic compounds known as oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds. Ophthalmic acid is a very strong basic compound (based on its pKa). Ophthalmic acid is an L-glutamine derivative in which L-glutamine is substituted by a 1--1-oxobutan-2-yl at the terminal amino nitrogen atom. Ophthalmic acid is an analogue of glutathione isolated from crystalline lens. Ophthalmic acid is an analogue of glutathione isolated from crystalline lens. [HMDB]

Stearidonic acid

C18H28O2 (276.2089)

Steridonic acid, also known as (6z,9z,12z,15z)-octadecatetraenoic acid or stearidonate, belongs to lineolic acids and derivatives class of compounds. Those are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Thus, steridonic acid is considered to be a fatty acid lipid molecule. Steridonic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Steridonic acid can be found in borage, which makes steridonic acid a potential biomarker for the consumption of this food product. Steridonic acid can be found primarily in blood and feces. In humans, steridonic acid is involved in the alpha linolenic acid and linoleic acid metabolism. Stearidonic acid is found in dietary plant oils which are metabolized to longer-chain, more unsaturated (n-3) PUFA. These oils appear to possess hypotriglyceridemic properties typically associated with fish oils.(PMID: 15173404). Stearidonic acid may be used as a precursor to increase the EPA content of human lipids and that combinations of gamma-linolenic acid and stearidonic acid eicosapentaenoic acid can be used to manipulate the fatty acid compositions of lipid pools in subtle ways. Such effects may offer new strategies for manipulation of cell composition in order to influence cellular responses and functions in desirable ways. (PMID: 15120716).

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].

Neoxanthin

C40H56O4 (600.4178)

Neoxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Xanthophylls arise by oxygenation of the carotene backbone. Neoxanthin is an intermediate in the synthesis of abscisic acid from violaxanthin. Neoxanthin has been detected, but not quantified in, several different foods, such as apples, paprikas, Valencia oranges, kiwis, globe artichokes, sparkleberries, hard wheat, and cinnamon. This could make neoxanthin a potential biomarker for the consumption of these foods. Neoxanthin has been shown to exhibit apoptotic and anti-proliferative functions (PMID: 15333710, 15333710). Neoxanthin is a carotenoid and xanthophyll. In plants, it is an intermediate in the biosynthesis of the plant hormone abscisic acid. It is produced from violaxanthin by the action of neoxanthin synthase. It is a major xanthophyll found in green leafy vegetables such as spinach. [Wikipedia] D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Violaxanthin

C40H56O4 (600.4178)

Violaxanthin belongs to the class of organic compounds known as xanthophylls. These are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Xanthophylls arise by oxygenation of the carotene backbone. Thus, violaxanthin is considered to be an isoprenoid lipid molecule. Violaxanthin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Violaxanthin is an orange-coloured pigment that is found in brown algae and various plants (e.g. pansies). It is biosynthesized from the epoxidation of zeaxanthin. Violaxanthin is a food additive that is only approved for use in Australia and New Zealand (INS: 161e) (PMID: 29890662). 3 (violaxanthin, zeaxanthin and antheraxanthin) participate in series of photo-induced interconversions known as violaxanthin cycle; Xanthophyll; a carotene epoxide that is precursor to capsanthin; cleavage of 9-cis-epoxycarotenoids (violaxanthin) to xanthoxin, catalyzed by 9-cis-epoxycarotenoid dioxygenase, is the key regulatory step of abscisic acid biosynthesis; one of 3 xanthophylls involved in evolution of plastids of green plants (oxygen evolution). (all-E)-Violaxanthin is found in many foods, some of which are orange bell pepper, passion fruit, pepper (c. annuum), and italian sweet red pepper. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Brassicasterol

C28H46O (398.3548)

Brassicasterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, brassicasterol is considered to be a sterol lipid molecule. Brassicasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Brassicasterol is a potential CSF biomarker for Alzheimer’s disease (PMID: 21585343). C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Constituent of Brassica rapa oil Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].

Epicubenol

C15H26O (222.1984)

1alpha-4-Cadinen-1-ol is found in cloves. 1alpha-4-Cadinen-1-ol is a constituent of oil of cubeb pepper (Piper cubeba). Constituent of cubeb pepper (Piper cubeba) oil. Epicubenol is found in herbs and spices.

Desmosterol

C27H44O (384.3392)

Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is found in many foods, some of which are fig, sago palm, mexican groundcherry, and pepper (c. frutescens). Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1]. Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1].

Pentadecanal

C15H30O (226.2297)

Isolated from essential oil of Cinnamomum micranthum and from lemon oil (Citrus limon). Pentadecanal is found in many foods, some of which are lemon, herbs and spices, citrus, and coriander. Pentadecanal is found in citrus. Pentadecanal is isolated from essential oil of Cinnamomum micranthum and from lemon oil (Citrus limon

Hexanal

C6H12O (100.0888)

Hexanal is an alkyl aldehyde found in human biofluids. Human milk samples collected from women contains hexanal. Among mediators of oxidative stress, highly reactive secondary aldehydic lipid peroxidation products can initiate the processes of spontaneous mutagenesis and carcinogenesis and can also act as a growth-regulating factors and signaling molecules. In specimens obtained from adult patients with brain astrocytomas, lower levels of n-hexanal are associated with poorer patient prognosis. Hexanal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). Hexanal is a volatile compound that has been associated with the development of undesirable flavours. The content of hexanal, which is a major breakdown product of linoleic acid (LA, n - 6 PUFA) oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods, and have been proposed as one potential marker of milk quality. A "cardboard-like" off-flavour is frequently associated with dehydrated milk products. This effect is highly correlated with the headspace concentration of hexanal. (Food Chemistry. Volume 107, Issue 1, 1 March 2008, Pages 558-569, PMID:17934948, 17487452). Constituent of many foodstuffs. A production of aerobic enzymatic transformations of plant constits. It is used in fruit flavours and in perfumery D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D010575 - Pesticides > D007306 - Insecticides D016573 - Agrochemicals

Pentadecane

C15H32 (212.2504)

Pentadecane, also known as ch3-[ch2]13-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, pentadecane is considered to be a hydrocarbon lipid molecule. Pentadecane is an alkane and waxy tasting compound and can be found in a number of food items such as dill, papaya, yellow bell pepper, and pepper (c. annuum), which makes pentadecane a potential biomarker for the consumption of these food products. Pentadecane can be found primarily in saliva. Pentadecane is a non-carcinogenic (not listed by IARC) potentially toxic compound. Pentadecane is an alkane hydrocarbon with the chemical formula C15H32 . Pentadecane belongs to the family of Acyclic Alkanes. These are acyclic hydrocarbons consisting only of n carbon atoms and m hydrogen atoms where m=2*n + 2

Fucosterol

C29H48O (412.3705)

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

Acutilol A

C20H32O2 (304.2402)

Germacrene

C15H24 (204.1878)

Germacrene, also known as (e,e)-germacra-1(10),4,7(11)-triene, is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Thus, germacrene is considered to be an isoprenoid lipid molecule. Germacrene can be found in turmeric, which makes germacrene a potential biomarker for the consumption of this food product. Germacrenes are a class of volatile organic hydrocarbons, specifically, sesquiterpenes. Germacrenes are typically produced in a number of plant species for their antimicrobial and insecticidal properties, though they also play a role as insect pheromones. Two prominent molecules are germacrene A and germacrene D .

Deoxylapachol

C15H14O2 (226.0994)

2-demethylmenaquinone is a naphthoquinone and a member of p-quinones. It has a role as an Escherichia coli metabolite. Deoxylapachol is a natural product found in Tectona grandis, Handroanthus impetiginosus, and other organisms with data available. Deoxylapachol is a major cytotoxic component of New Zealand brown alga, Landsburgia quercifolia. Deoxylapachol has antifungal and anti-cancer activity[1]. Deoxylapachol is a major cytotoxic component of New Zealand brown alga, Landsburgia quercifolia. Deoxylapachol has antifungal and anti-cancer activity[1].

Apiole

C12H14O4 (222.0892)

Apiole is found in dill. Apiole occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill) Apiol is an organic chemical compound, also known as parsley apiol, apiole or parsley camphor. It is found in celery, parsley seeds, and the essential oil of parsley. Heinrich Christoph Link, an apothecary in Leipzig, discovered the substance in 1715 as greenish crystals reduced by steam from oil of parsley. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation. In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders. It is an irritant and in high doses it is toxic and can cause liver and kidney damage. Occurs in Sassafras albidum (sassafras) and Anethum graveolens (dill)

Grevillol

C19H32O2 (292.2402)

Hexachlorobutadiene

C4Cl6 (257.8131)

D016573 - Agrochemicals D010575 - Pesticides

24-Methylenecholesterol

C28H46O (398.3548)

24-Methylenecholesterol, also known as chalinasterol or ostreasterol, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, 24-methylenecholesterol is considered to be a sterol lipid molecule. 24-Methylenecholesterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 24-Methylenecholesterol is involved in the biosynthesis of steroids. 24-Methylenecholesterol is converted from 5-dehydroepisterol by 7-dehydrocholesterol reductase (EC 1.3.1.21). 24-Methylenecholesterol is converted into campesterol by delta24-sterol reductase (EC 1.3.1.72). 24-methylenecholesterol is a 3beta-sterol having the structure of cholesterol with a methylene group at C-24. It has a role as a mouse metabolite. It is a 3beta-sterol and a 3beta-hydroxy-Delta(5)-steroid. It is functionally related to a cholesterol. 24-Methylenecholesterol is a natural product found in Echinometra lucunter, Ulva fasciata, and other organisms with data available. A 3beta-sterol having the structure of cholesterol with a methylene group at C-24. Constituent of clams and oysters 24-Methylenecholesterol (Ostreasterol), a natural marine sterol, stimulates cholesterol acyltransferase in human macrophages. 24-Methylenecholesterol possess anti-aging effects in yeast. 24-methylenecholesterol enhances honey bee longevity and improves nurse bee physiology[1][2][3].

Nonadecanoic acid

C19H38O2 (298.2872)

Nonadecanoic acid, also known as n-nonadecanoic acid or nonadecylic acid or C19:0, 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, with nonadecanoic acid (its ester is called nonadecanoate) having 19 carbon atoms. Nonadecanoic acid is a very hydrophobic molecule, practically insoluble (in water). It is a solid with a melting point of 69.4°C. It can be found in bacteria, plants, and animals (including animal milk) (Nature 176:882; PMID: 14168161). It is secreted by termites (Rhinotermes marginalis) as part of its defence mechanism (Comp. Biochem. Physiol. B 71:731). Nonadecanoic acid is a C19 straight-chain fatty acid of plant or bacterial origin. An intermediate in the biodegradation of n-icosane, it has been shown to inhibit cancer growth. It has a role as a fungal metabolite. It is a straight-chain saturated fatty acid and a long-chain fatty acid. It is a conjugate acid of a nonadecanoate. Nonadecanoic acid is a natural product found in Staphisagria macrosperma, Malva sylvestris, and other organisms with data available. An odd-numbered long chain fatty acid, likely derived from bacterial or plant sources. Nonadecanoic acid has been found in ox fats and vegetable oils. It is also used by certain insects as a phermone. [HMDB]. A C19 straight-chain fatty acid of plant or bacterial origin. An intermediate in the biodegradation of n-icosane, it has been shown to inhibit cancer growth. Nonadecanoic acid is a 19-carbon long saturated fatty acid. Nonadecanoic acid is the major constituent of the substance secreted by Rhinotermes marginalis to defence[1]. Nonadecanoic acid is a 19-carbon long saturated fatty acid. Nonadecanoic acid is the major constituent of the substance secreted by Rhinotermes marginalis to defence[1].

Pachydictyol A

C20H32O (288.2453)

Lanosol

C7H6Br2O3 (295.8684)

Glucose

C6H12O6 (180.0634)

D-Galactose (CAS: 59-23-4) is an aldohexose that occurs naturally in the D-form in lactose, cerebrosides, gangliosides, and mucoproteins. D-Galactose is an energy-providing nutrient and also a necessary basic substrate for the biosynthesis of many macromolecules in the body. Metabolic pathways for D-galactose are important not only for the provision of these pathways but also for the prevention of D-galactose metabolite accumulation. The main source of D-galactose is lactose in the milk of mammals, but it can also be found in some fruits and vegetables. Utilization of D-galactose in all living cells is initiated by the phosphorylation of the hexose by the enzyme galactokinase (E.C. 2.7.1.6) (GALK) to form D-galactose-1-phosphate. In the presence of D-galactose-1-phosphate uridyltransferase (E.C. 2.7.7.12) (GALT) D-galactose-1-phosphate is exchanged with glucose-1-phosphate in UDP-glucose to form UDP-galactose. Glucose-1-phosphate will then enter the glycolytic pathway for energy production. Deficiency of the enzyme GALT in galactosemic patients leads to the accumulation of D-galactose-1-phosphate. Classic galactosemia, a term that denotes the presence of D-galactose in the blood, is the rare inborn error of D-galactose metabolism, diagnosed by the deficiency of the second enzyme of the D-galactose assimilation pathway, GALT, which, in turn, is caused by mutations at the GALT gene (PMID: 15256214, 11020650, 10408771). Galactose in the urine is a biomarker for the consumption of milk. Alpha-D-Pyranose-form of the compound Galactose [CCD]. alpha-D-Galactose is found in many foods, some of which are kelp, fig, spelt, and rape. Galactose. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=59-23-4 (retrieved 2024-07-16) (CAS RN: 59-23-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

L-Fucose

C6H12O5 (164.0685)

Fucose (CAS: 2438-80-4) is a hexose deoxy sugar with the chemical formula C6H12O5. L-Fucose (6-deoxy-L-galactose) is a monosaccharide that is a common component of many N- and O-linked glycans and glycolipids produced by mammalian cells. It is the fundamental subunit of the fucoidan polysaccharide. As a free sugar, L-fucose is normally found at very low levels in mammals. It is unique in that it is the only levorotatory sugar synthesized and utilized by mammals. Fucose polymers are synthesized by fucosyltransferases. All fucosyltransferases utilize a nucleotide-activated form of fucose, GDP-fucose, as a fucose donor in the construction of fucosylated oligosaccharides. The ABO blood group antigens are among the most well known fucosylated glycans. The alpha-1->3 linked core fucose is a suspected carbohydrate antigen for IgE-mediated allergy. Two structural features distinguish fucose from other six-carbon sugars present in mammals: the lack of a hydroxyl group on the carbon at the 6-position (C-6) and the L-configuration. In fucose-containing glycan structures, fucosylated glycans, fucose can exist as a terminal modification or serve as an attachment point for adding other sugars. Fucose is metabolized by an enzyme called alpha-fucosidase. Fucose is secreted in urine when the liver is damaged. Free L-fucose in serum and urine can be used as a marker for cancer, cirrhosis, alcoholic liver disease and gastric ulcers (PMID: 2311216, 8488966). Elevated levels of serum fucose have been reported in breast cancer, ovarian cancer, lung cancer, liver cancer, diabetes, and cardiovascular disease. It has been shown that feeding rats a diet high in L-fucose induces neuropathy similar to that seen in diabetics. A constituent of the polysaccharides obtained from gum tragacanthand is) also found in glycoproteins obtained from milk (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.

Sorbitol

C6H14O6 (182.079)

Sorbitol is a polyhydric alcohol with about half the sweetness of sucrose. Sorbitol occurs naturally and is also produced synthetically from glucose. It was formerly used as a diuretic and may still be used as a laxative and in irrigating solutions for some surgical procedures. It is also used in many manufacturing processes, as a pharmaceutical aid, and in several research applications. Ascorbic acid fermentation; in solution form for moisture-conditioning of cosmetic creams and lotions, toothpaste, tobacco, gelatin; bodying agent for paper, textiles, and liquid pharmaceuticals; softener for candy; sugar crystallization inhibitor; surfactants; urethane resins and rigid foams; plasticizer, stabilizer for vinyl resins; food additive (sweetener, humectant, emulsifier, thickener, anticaking agent); dietary supplement. (Hawleys Condensed Chemical Dictionary) Biological Source: Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus species Use/Importance: Used for manufacturing of sorbose, propylene glycol, ascorbic acid, resins, plasticizers and as antifreeze mixtures with glycerol or glycol. Tablet diluent, sweetening agent and humectant, other food uses. Sorbitol is used in photometric determination of Ru(VI) and Ru(VIII); in acid-base titration of borate (Dictionary of Organic Compounds). Occurs widely in plants ranging from algae to the higher orders. Fruits of the plant family Rosaceae, which include apples, pears, cherries, apricots, contain appreciable amounts. Rich sources are the fruits of the Sorbus and Crataegus subspecies Sweetening agent and humectant and many other food uses. D-Glucitol is found in many foods, some of which are common salsify, other bread, wild rice, and common chokecherry. A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AD - Osmotically acting laxatives A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AG - Enemas B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CC - Tests for bile duct patency Acquisition and generation of the data is financially supported in part by CREST/JST. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D005765 - Gastrointestinal Agents > D002400 - Cathartics D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1]. D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1].

D-Alanine

C3H7NO2 (89.0477)

Alanine is a nonessential amino acid made in the body from the conversion of the carbohydrate pyruvate or the breakdown of DNA and the dipeptides carnosine and anserine. It is highly concentrated in muscle and is one of the most important amino acids released by muscle, functioning as a major energy source. Plasma alanine is often decreased when the BCAA (Branched Chain Amino Acids) are deficient. This finding may relate to muscle metabolism. Alanine is highly concentrated in meat products and other high-protein foods like wheat germ and cottage cheese. Alanine is an important participant as well as regulator in glucose metabolism. Alanine levels parallel blood sugar levels in both diabetes and hypoglycemia, and alanine reduces both severe hypoglycemia and the ketosis of diabetes. It is an important amino acid for lymphocyte reproduction and immunity. Alanine therapy has helped dissolve kidney stones in experimental animals. Normal alanine metabolism, like that of other amino acids, is highly dependent upon enzymes that contain vitamin B6. Alanine, like GABA, taurine and glycine, is an inhibitory neurotransmitter in the brain. Alanine can be found in some Gram-positive bacteria (PMID:24752840). Amino acids are one of the most important molecules in living organisms, and most of them have a chiral carbon at a -position. In the higher animals, a large part of the naturally occurring amino acids is the L-form, and the stereoisomers (D-amino acids) had been believed to be rare. However, several D-amino acids have been found in mammals including humans, and their distributions, functions and origins have gradually been clarified. The D-alanine (D-Ala) amounts have also been reported to change in the case of diseases. Proteins of the frontal lobe white and gray matter of human brains, both normal and Alzheimer subjects, contain D-alanine at concentrations between 0.50 and 1.28 mumol/g of wet tissue, 50-70-times lower than the concentration of L-alanine. D-Alanine have been detected in the sera of both normal subjects and patients with renal dysfunction, and their concentrations were higher in the patients than in the normal subjects. (PMID: 16141519, 1450921, 8535409, 1426150, 1933416) [HMDB] KEIO_ID A011 D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR.

Dehydrovomifoliol

C13H18O3 (222.1256)

Isolated from rice husks (Oryza sativa L. cv Koshihikari). Dehydrovomifoliol is found in tea, cereals and cereal products, and common grape. Dehydrovomifoliol is found in cereals and cereal products. Dehydrovomifoliol is isolated from rice husks (Oryza sativa L. cv Koshihikari).

DL-2-Aminopropionic acid

C3H7NO2 (89.0477)

(alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein), also known as ALA or 2-Aminopropanoic acid, is classified as an alanine or an Alanine derivative. Alanines are compounds containing alanine or a derivative thereof resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein) is considered to be soluble (in water) and acidic. (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein) can be synthesized from propionic acid. (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein) can be synthesized into alanine derivative. (alpha-D-mannosyl)7-beta-D-mannosyl-diacetylchitobiosyl-L-asparagine, isoform A (protein) is an odorless tasting compound found in Green bell peppers, Green zucchinis, Italian sweet red peppers, and Red bell peppers Dietary supplement, nutrient, sweetening flavour enhancer in pickling spice mixts. DL-alanine, an amino acid, is the racemic compound of L- and D-alanine. DL-alanine is employed both as a reducing and a capping agent, used with silver nitrate aqueous solutions for the production of nanoparticles. DL-alanine can be used for the research of transition metals chelation, such as Cu(II), Zn(II), Cd(11). DL-alanine, a sweetener, is classed together with glycine, and sodium saccharin. DL-alanine plays a key role in the glucose-alanine cycle between tissues and liver[1][2][3][4][5][6].

3-Bromo-4-hydroxybenzoic acid

C7H5BrO3 (215.9422)

A monohydroxybenzoic acid that is 4-hydroxybenzoic acid carrying an additional bromo substituent at position 3.

(+)-germacrene D

C15H24 (204.1878)

3-bromo-4,5-Dihydroxybenzoic acid

C7H5BrO4 (231.9371)

A dihydroxybenzoic acid that is 4,5-dihydroxybenzoic acid carrying an additional bromo substituent at position 3.

2-Hydroxy-6-tridecylbenzoic acid

C20H32O3 (320.2351)

2-Hydroxy-6-tridecylbenzoic acid is a hydroxybenzoic acid. It is functionally related to a salicylic acid. 2-Hydroxy-6-tridecylbenzoic acid is a natural product found in Ginkgo biloba and Caulocystis cephalornithos with data available. 2-Hydroxy-6-tridecylbenzoic acid is found in fats and oils. 2-Hydroxy-6-tridecylbenzoic acid is isolated from pistachio shells. 2-Hydroxy-6-tridecylbenzoic acid is isolated from Ginkgo biloba (ginkgo). Isolated from pistachio shells. Isolated from Ginkgo biloba (ginkgo). 2-Hydroxy-6-tridecylbenzoic acid is found in fats and oils and nuts. D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates Ginkgolic Acid (C13:0) is a natural anticariogenic agent in that it exhibits antimicrobial activity against S. mutans and suppresses the specific virulence factors associated with its cariogenicity. IC50 value: Inhibiting the biofilm formation of S. mutans (MBIC (50) = 4 μg/mL); reduced 1-day-developed biofilm of S. mutans by 50 \\% or more at low concentration (MBRC (50) = 32 μg/mL). Target: In vitro: Ginkgolic Acid (C13:0) inhibited not only the growth of S. mutans planktonic cells at minimum inhibitory concentration (MIC) of 4 μg/mL and minimum bactericidal concentration (MBC) of 8 μg/mL but also the acid production and adherence to saliva-coated hydroxyapatite of S. mutans at sub-MIC concentration. In addition, this agent was effective in inhibiting the biofilm formation of S. mutans (MBIC (50) = 4 μg/mL), and it reduced 1-day-developed biofilm of S. mutans by 50 \\% or more at low concentration (MBRC (50) = 32 μg/mL). Furthermore Ginkgolic Acid (C13:0) disrupted biofilm integrity effectively [1]. In vivo: Ginkgolic Acid (C13:0) is a natural anticariogenic agent in that it exhibits antimicrobial activity against S. mutans and suppresses the specific virulence factors associated with its cariogenicity. IC50 value: Inhibiting the biofilm formation of S. mutans (MBIC (50) = 4 μg/mL); reduced 1-day-developed biofilm of S. mutans by 50 \% or more at low concentration (MBRC (50) = 32 μg/mL). Target: In vitro: Ginkgolic Acid (C13:0) inhibited not only the growth of S. mutans planktonic cells at minimum inhibitory concentration (MIC) of 4 μg/mL and minimum bactericidal concentration (MBC) of 8 μg/mL but also the acid production and adherence to saliva-coated hydroxyapatite of S. mutans at sub-MIC concentration. In addition, this agent was effective in inhibiting the biofilm formation of S. mutans (MBIC (50) = 4 μg/mL), and it reduced 1-day-developed biofilm of S. mutans by 50 \% or more at low concentration (MBRC (50) = 32 μg/mL). Furthermore Ginkgolic Acid (C13:0) disrupted biofilm integrity effectively [1]. In vivo:

Spathulenol

C15H24O (220.1827)

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

Dihydroactinidiolide

C11H16O2 (180.115)

Dihydroactinidiolide is a member of the class of compounds known as benzofurans. Benzofurans are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Dihydroactinidiolide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Dihydroactinidiolide is a red fruit, ripe apricot, and woody tasting compound found in coffee and coffee products, fruits, and tea, which makes dihydroactinidiolide a potential biomarker for the consumption of these food products. Dihydroactinidiolide exists in all eukaryotes, ranging from yeast to humans. Dihydroactinidiolide is a volatile terpene. It has a sweet, tea-like odor and is used as a fragrance. Dihydroactinidiolide occurs naturally in black tea, fenugreek, fire ants, mangos, silver vine (Actinidia polygama), and tobacco. It has also been prepared synthetically . Dihydroactinidiolide is found in coffee and coffee products. Dihydroactinidiolide has been isolated from tea, coffee and fruits. Dihydroactinidiolide is an important aroma constituent of tea. Dihydroactinidiolide is a member of benzofurans. Dihydroactinidiolide is a natural product found in Tagetes lucida, Cucumis melo, and other organisms with data available. (±)-Dihydroactinidiolide, an important aroma compound of black tea and tobacco, has been isolated from several plants. (±)-Dihydroactinidiolide can be formation from β-Carotene by the treatment of polyphenoloxidase, the lipoxygenase, and the xanthine oxidase[1][2]. (±)-Dihydroactinidiolide, an important aroma compound of black tea and tobacco, has been isolated from several plants. (±)-Dihydroactinidiolide can be formation from β-Carotene by the treatment of polyphenoloxidase, the lipoxygenase, and the xanthine oxidase[1][2].

Abscisic acid

C15H20O4 (264.1362)

Abscisic acid is found in american cranberry. Abscisic acid is used to regulate ripening of fruit Abscisic acid (ABA) is an isoprenoid plant hormone, which is synthesized in the plastidal 2-C-methyl-d-erythritol-4-phosphate (MEP) pathway; unlike the structurally related sesquiterpenes, which are formed from the mevalonic acid-derived precursor farnesyl diphosphate (FDP), the C15 backbone of ABA is formed after cleavage of C40 carotenoids in MEP. Zeaxanthin is the first committed ABA precursor; a series of enzyme-catalyzed epoxidations and isomerizations, and final cleavage of the C40 carotenoid by a dioxygenation reaction yields the proximal ABA precursor, xanthoxin, which is then further oxidized to ABA. Abamine has been patented by the Japanese researchers Shigeo Yoshida and Tadao Asami, which are very reluctant to make this substance available in general, neither commercially nor for research purposes. Abscisic acid (ABA), also known as abscisin II and dormin, is a plant hormone. It functions in many plant developmental processes, including bud dormancy 2-trans-abscisic acid is an abscisic acid in which the two acyclic double bonds both have trans-geometry. It is a conjugate acid of a 2-trans-abscisate. 2-cis,4-trans-Abscisic acid is a natural product found in Axinella polypoides, Phaseolus vulgaris, and Vernicia fordii with data available. Abscission-accelerating plant growth substance isolated from young cotton fruit, leaves of sycamore, birch, and other plants, and from potatoes, lemons, avocados, and other fruits. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D006133 - Growth Substances > D010937 - Plant Growth Regulators It is used to regulate ripening of fruit Abscisic acid ((S)-(+)-Abscisic acid), an orally active phytohormone in fruits and vegetables, is an endogenously produced mammalian hormone. Abscisic acid is a growth inhibitor and can regulate many aspects of plant growth and development. Abscisic acid inhibits proton pump (H+-ATPase) and leads to the plasma membrane depolarization in a Ca2+-dependent manner. Abscisic acid, a LANCL2 natural ligand, is a potent insulin-sensitizing compound and has the potential for pre-diabetes, type 2 diabetes and metabolic syndrome[1][2]. Abscisic acid ((S)-(+)-Abscisic acid), an orally active phytohormone in fruits and vegetables, is an endogenously produced mammalian hormone. Abscisic acid is a growth inhibitor and can regulate many aspects of plant growth and development. Abscisic acid inhibits proton pump (H+-ATPase) and leads to the plasma membrane depolarization in a Ca2+-dependent manner. Abscisic acid, a LANCL2 natural ligand, is a potent insulin-sensitizing compound and has the potential for pre-diabetes, type 2 diabetes and metabolic syndrome[1][2].

Nonanal

C9H18O (142.1358)

Nonanal, also known as nonyl aldehyde or pelargonaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, nonanal is considered to be a fatty aldehyde lipid molecule. Nonanal acts synergistically with carbon dioxide in that regard. Nonanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Nonanal exists in all eukaryotes, ranging from yeast to humans. Nonanal is an aldehydic, citrus, and fat tasting compound. nonanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and gingers and in a lower concentration in sweet oranges, carrots, and limes. nonanal has also been detected, but not quantified, in several different foods, such as olives, cereals and cereal products, chinese cinnamons, common grapes, and oats. This could make nonanal a potential biomarker for the consumption of these foods. Nonanal has been identified as a compound that attracts Culex mosquitoes. Nonanal is a potentially toxic compound. Nonanal has been found to be associated with several diseases such as pervasive developmental disorder not otherwise specified, autism, crohns disease, and ulcerative colitis; also nonanal has been linked to the inborn metabolic disorders including celiac disease. Nonanal, also called nonanaldehyde, pelargonaldehyde or Aldehyde C-9, is an alkyl aldehyde. Although it occurs in several natural oils, it is produced commercially by hydroformylation of 1-octene. A colourless, oily liquid, nonanal is a component of perfumes. Nonanal is a clear brown liquid characterized by a rose-orange odor. Insoluble in water. Found in at least 20 essential oils, including rose and citrus oils and several species of pine oil. Nonanal is a saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. It has a role as a human metabolite and a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. It is functionally related to a nonanoic acid. Nonanal is a natural product found in Teucrium montanum, Eupatorium cannabinum, and other organisms with data available. Nonanal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.Nonanal belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms. Found in various plant sources including fresh fruits, citrus peels, cassava (Manihot esculenta), rice (Oryza sativa). Flavouring ingredient A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1]. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1].

Heptadecanoic acid

C17H34O2 (270.2559)

Heptadecanoic acid, or margaric acid, is a saturated fatty acid. It occurs as a trace component of the fat and milkfat of ruminants, but it does not occur in any natural animal or vegetable fat at concentrations over half a percent. Salts and esters of heptadecanoic acid are called heptadecanoates (Wikipedia). Heptadecanoic acid is found in many foods, some of which are dandelion, potato, ginger, and green bean. Heptadecanoic acid is a constituent of Erythrina crista-galli trunkwood and bark. Common constituent of lipids, e.g. present in Physalia physalis (Portuguese-man-of-war). Heptadecanoic acid is a fatty acid of exogenous (primarily ruminant) origin. Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Heptadecanoic acid constitutes 0.61\\\\% of milk fat and 0.83\\\\% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID 9701185). Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1]. Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1].

Geranylacetone

C13H22O (194.1671)

Constituent of many essential oils including peppermint (Mentha piperita) and Carolina vanilla (Carphephorus odoratissimus). It is used in food flavouring. Geranylacetone is found in many foods, some of which are corn, pepper (c. frutescens), herbs and spices, and watermelon. Geranylacetone is found in carrot. Geranylacetone is a constituent of many essential oils including peppermint (Mentha piperita) and Carolina vanilla (Carphephorus odoratissimus). Geranylacetone is used in food flavouring

1-Penten-3-ol

C5H10O (86.0732)

1-Penten-3-ol, also known as fema 3584, belongs to the class of organic compounds known as secondary alcohols. Secondary alcohols are compounds containing a secondary alcohol functional group, with the general structure HOC(R)(R) (R,R=alkyl, aryl). 1-Penten-3-ol exists in all eukaryotes, ranging from yeast to humans. 1-Penten-3-ol is a bitter and fruity tasting compound. 1-Penten-3-ol is found, on average, in the highest concentration within a few different foods, such as tea, milk (cow), and safflowers and in a lower concentration in kohlrabis. 1-Penten-3-ol has also been detected, but not quantified, in several different foods, such as mung beans, rabbiteye blueberries, pomes, cauliflowers, and evergreen blackberries. Isolated from soya (Glycine max), banana, orange juice or peel oil, raspberries, asparagus, shallot, crispbread, smoked fatty fish, scallops, roasted peanut, black and green tea (Thea sinensis) and other foods. Flavouring ingredient. 1-Penten-3-ol is found in many foods, some of which are pulses, sweet bay, blackcurrant, and kohlrabi.

(E)-Calamene

C15H22 (202.1721)

Calamene is a metabolite of plant Turnera diffusa. Turnera diffusa (Damiana, Mexican holly, Old Womans Broom) is a small shrub of the family Tuneraceae. T. diffusa is native to both Central and South America and now commercially cultivated in Bolivia and Mexico. The leaf includes volatile oils (1,8-cineole, p-cymene, alpha- and beta-pinene, thymol, alpha-copaene, and calamene); luteolin; tannins, flavonoids (arbutin, acacetin, apigenin and pinocembrin), beta-sitosterol, damianin, and the cyanogenic glycoside tetraphyllin B. (www.globinmed.com) (e)-calamene is also known as calamenene or 1,6-dimethyl-4-isopropyltetralin. (e)-calamene can be found in a number of food items such as guava, lovage, summer savory, and rosemary, which makes (e)-calamene a potential biomarker for the consumption of these food products (e)-calamene can be found primarily in urine.

delta-Amorphene

C15H24 (204.1878)

1(10),4-Cadinadiene is a cadinene (FDB009046) of the delta-serie [FooDB]. A cadinene (FDB009046) of the delta-serie [FooDB]

Tridecanal

C13H26O (198.1984)

Volatile flavour component of coriander leafand is also in lemon and cucumber oils. Tridecanal is found in many foods, some of which are herbs and spices, lemon, corn, and citrus. Tridecanal is found in citrus. Tridecanal is a volatile flavour component of coriander leaf. Also in lemon and cucumber oil

2-Pentadecanone

C15H30O (226.2297)

2-Pentadecanone is found in cereals and cereal products. 2-Pentadecanone is isolated from hop (Humulus lupulus), coconut (Cocos nucifera) and other oils. Also found in American cranberry, feijoa fruit, quince, asparagus, ginger, wheat bread, soybean, cooked rice and cheeses. 2-Pentadecanone is a flavouring ingredien Isolated from hop (Humulus lupulus), coconut (Cocos nucifera) and other oilsand is also found in American cranberry, feijoa fruit, quince, asparagus, ginger, wheat bread, soybean, cooked rice and cheeses. Flavouring ingredient.

Cystophorene

C11H18 (150.1408)

Cystophorene is found in herbs and spices. Cystophorene is a food additive listed in the EAFUS food Additive Database (Jan. 2001). Cystophorene occurs in Galbanum extract (Ferula galbaniflua Food additive listed in the EAFUS Food Additive Database (Jan. 2001). Occurs in Galbanum extract (Ferula galbaniflua). Cystophorene is found in herbs and spices.

2-Heptadecanone

C17H34O (254.261)

2-Heptadecanone is a constituent of aroma compounds of white bread

gamma1-Cadinene

C15H24 (204.1878)

gamma1-Cadinene is found in fats and oils. gamma1-Cadinene is a constituent of citronella oil (Cymbopogon nardus). gamma1-Cadinene is a mixture of cadinene isomers from various essential oils is used as a flavouring agent/flavour modifier. Constituent of citronella oil (Cymbopogon nardus). A mixture of cadinene isomers from various essential oils is used as a flavouring agent/flavour modifier. gamma1-Cadinene is found in fats and oils and herbs and spices.

Cadalene

C15H18 (198.1408)

Cadalene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, cadalene is considered to be an isoprenoid lipid molecule. Cadalene can be found in a number of food items such as cloves, sugar apple, rosemary, and fig, which makes cadalene a potential biomarker for the consumption of these food products. Cadalene can be found primarily in saliva and urine. Cadalene exists in all eukaryotes, ranging from yeast to humans. Cadalene or cadalin (4-isopropyl-1,6-dimethylnaphthalene) is a polycyclic aromatic hydrocarbon with a chemical formula C15H18 and a cadinane skeleton. It is derived from generic sesquiterpenes, and ubiquitous in essential oils of many higher plants . Cadalene (4-isopropyl-1,6-dimethylnaphthalene) is a polycyclic aromatic hydrocarbon with a chemical formula C15H18 and a cadinane skeleton. It is derived from generic sesquiterpenes, and ubiquitous in essential oils of many higher plants. Cadalene, together with retene, simonellite and ip-iHMN, is a biomarker of higher plants, which makes it useful for paleobotanic analysis of rock sediments. The ratio of retene to cadalene in sediments can reveal the ratio of the genus Pinaceae in the biosphere. (Wikipedia)

1-Pentadecene

C15H30 (210.2347)

1-Pentadecene, also known as pentadec-1-ene, belongs to the class of organic compounds known as unsaturated aliphatic hydrocarbons. These are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. 1-Pentadecene is an unbranched fifteen-carbon alkene with one double bond between C-1 and C-2. These compounds contain one or more double or triple bonds. Thus, 1-pentadecene is considered to be a hydrocarbon lipid molecule. 1-Pentadecene is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 1-Pentadecene is found, on average, in the highest concentration within safflowers. 1-Pentadecene has also been detected, but not quantified, in burdocks and watermelons. This could make 1-pentadecene a potential biomarker for the consumption of these foods. Occurs in beef and oakmoss oleoresin. 1-Pentadecene is found in many foods, some of which are animal foods, burdock, safflower, and watermelon.

Cubenol

C15H26O (222.1984)

Cubenol belongs to the family of Sesquiterpenes. These are terpenes with three consecutive isoprene units

(-)-alpha-Tocopherol

C29H50O2 (430.3811)

α-tocopherol is a member of the class of compounds known as tocopherols. Tocopherols are vitamin E derivatives containing a saturated trimethyltridecyl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocotrienols that contain an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain. α-tocopherol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). α-tocopherol can be found in a number of food items such as lime, rowanberry, horseradish tree, and pineappple sage, which makes α-tocopherol a potential biomarker for the consumption of these food products. α-tocopherol is a form of vitamin E that is preferentially absorbed and accumulated in humans. The measurement of "vitamin E" activity in international units (IU) was based on fertility enhancement by the prevention of spontaneous abortions in pregnant rats relative to α-tocopherol .

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

C27H40O2 (396.3028)

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

C28H42O2 (410.3185)

1-Iodopentane

C5H11I (197.9905)

5,8,11,14-Icosatetraenoic Acid

C20H32O2 (304.2402)

Octadeca-6,9,12,15-tetraenoic acid

C18H28O2 (276.2089)

Octadeca-6,9,12,15-tetraenoic acid, also known as 6,9,12,15-octadecatetraenoic acid, belongs to lineolic acids and derivatives class of compounds. Those are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. Octadeca-6,9,12,15-tetraenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Octadeca-6,9,12,15-tetraenoic acid can be found in borage, which makes octadeca-6,9,12,15-tetraenoic acid a potential biomarker for the consumption of this food product.

Squalen

C30H50 (410.3912)

(E,E,E)-Geranylgeranyl alcohol

C20H34O (290.261)

beta-Jonone

C13H20O (192.1514)

D-Iditol

C6H14O6 (182.079)

Permitted bulk sweetener for foods. Sweetening agent. Food additive, used as anticaking agent, lubricant, for stabiliser and thickener, and for other uses in food processing

Dieckol

C36H22O18 (742.0806)

Dieckol, is a naturally occurring phlorotannin found in some brown algal species. Dieckol has anti-bacterial, anti-cancer, anti-oxidant, anti-aging, anti-diabetic, neuroprotective actions[1]. Dieckol, is a naturally occurring phlorotannin found in some brown algal species. Dieckol has anti-bacterial, anti-cancer, anti-oxidant, anti-aging, anti-diabetic, neuroprotective actions[1].

Eckol

C18H12O9 (372.0481)

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 .

Muurolol

C15H26O (222.1984)

Muurolol is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Muurolol is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Muurolol can be found in mugwort, which makes muurolol a potential biomarker for the consumption of this food product.

Loliolide

C11H16O3 (196.1099)

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

Latoxanthin

C40H58O5 (618.4284)

Latoxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Latoxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Latoxanthin can be found in a number of food items such as red bell pepper, yellow bell pepper, orange bell pepper, and pepper (c. annuum), which makes latoxanthin a potential biomarker for the consumption of these food products.

delta-Cadinol

C15H26O (222.1984)

Delta-cadinol, also known as delta-cadinol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Delta-cadinol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Delta-cadinol is a herbal tasting compound and can be found in a number of food items such as cloves, parsley, lemon balm, and common sage, which makes delta-cadinol a potential biomarker for the consumption of these food products. Delta-cadinol, also known as δ-cadinol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Delta-cadinol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Delta-cadinol is a herbal tasting compound and can be found in a number of food items such as cloves, parsley, lemon balm, and common sage, which makes delta-cadinol a potential biomarker for the consumption of these food products.

Germacrene A

C15H24 (204.1878)

Germacrene a is a member of the class of compounds known as germacrane sesquiterpenoids. Germacrane sesquiterpenoids are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Germacrene a can be found in sweet basil, which makes germacrene a a potential biomarker for the consumption of this food product.

1-S-cis-Calamenene

C15H22 (202.1721)

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

Zonarene

C15H24 (204.1878)

Zonarene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Zonarene can be found in allspice, cloves, and ginger, which makes zonarene a potential biomarker for the consumption of these food products.

7E, 9E-Octadecadienoic acid

C15H24 (204.1878)

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.

C17:0

C17H34O2 (270.2559)

Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1]. Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1].

PHENYLACETIC ACID

C8H8O2 (136.0524)

D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents

Choline

[C5H14NO]+ (104.1075)

D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D008082 - Lipotropic Agents D002491 - Central Nervous System Agents > D018697 - Nootropic Agents D009676 - Noxae > D000963 - Antimetabolites D005765 - Gastrointestinal Agents

Monocrotaline

C16H23NO6 (325.1525)

Monocrotaline is a pyrrolizidine alkaloid. Monocrotaline is a natural product found in Crotalaria novae-hollandiae, Crotalaria recta, and other organisms with data available. A pyrrolizidine alkaloid and a toxic plant constituent that poisons livestock and humans through the ingestion of contaminated grains and other foods. The alkaloid causes pulmonary artery hypertension, right ventricular hypertrophy, and pathological changes in the pulmonary vasculature. Significant attenuation of the cardiopulmonary changes are noted after oral magnesium treatment. Origin: Plant; SubCategory_DNP: Alkaloids derived from ornithine, Pyrrolizidine alkaloids relative retention time with respect to 9-anthracene Carboxylic Acid is 0.154 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.142 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.145 Monocrotaline is an 11-membered macrocyclic pyrrolizidine alkaloid. Monocrotaline inhibits OCT-1 and OCT-2 with IC50s of 36.8 μM and 1.8 mM, respectively. Monocrotaline has antitumor activity and is cytotoxic to hepatocellular carcinoma cells. Monocrotaline is used to induce a model of pulmonary hypertension in rodents. [2][6][8]. Monocrotaline is an 11-membered macrocyclic pyrrolizidine alkaloid. Monocrotaline inhibits OCT-1 and OCT-2 with IC50s of 36.8 μM and 1.8 mM, respectively. Monocrotaline has antitumor activity and is cytotoxic to hepatocellular carcinoma cells. Monocrotaline is used to induce a model of pulmonary hypertension in rodents. [2][6][8].

Sargachromanol C

C27H40O3 (412.2977)

Sargachromanol B

C22H32O3 (344.2351)

Sargachromanol A

C22H30O3 (342.2195)

Sargachromanol F

C28H42O4 (442.3083)

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

4-Hydroxyphenylacetic acid

C8H8O3 (152.0473)

4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

Moroctic acid

C18H28O2 (276.2089)

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].

Betaine

C5H11NO2 (117.079)

Betaine or trimethylglycine is a methylated derivative of glycine. It functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. The donation of methyl groups is important to proper liver function, cellular replication, and detoxification reactions. Betaine also plays a role in the manufacture of carnitine and serves to protect the kidneys from damage. Betaine has also been of interest for its role in osmoregulation. As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances. (From Martindale, The Extra Pharmacopoeia, 30th Ed, p1341). Betaine is found in many foods, some of which are potato puffs, poppy, hazelnut, and garden cress. Betaine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=107-43-7 (retrieved 2024-06-28) (CAS RN: 107-43-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

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.

Glucose

C6H12O6 (180.0634)

B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CA - Tests for diabetes V - Various > V06 - General nutrients > V06D - Other nutrients > V06DC - Carbohydrates COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS alpha-D-glucose is an endogenous metabolite. alpha-D-glucose is an endogenous metabolite.

methyl icosa-8,11,14-trienoate

C21H36O2 (320.2715)

Dehydrovomifoliol

C13H18O3 (222.1256)

Fucosterol

C29H48O (412.3705)

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

Arachidonic acid

C20H32O2 (304.2402)

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

Colpol

C17H16Br2O4 (441.9415)

An organobromine compound that is 2-bromobenzene-1,3-diol substituted at position 5 by a (2Z)-4-(4-bromo-2-hydroxy-5-methoxyphenyl)but-2-en-1-yl group. It is isolated from the Red Sea alga Colpomenia sinuosa and exhibits cytotoxicity towards P388, A549, HT-29 and CV-1 tumor cells.

Neoxanthin

C40H56O4 (600.4178)

9-cis-neoxanthin is a neoxanthin in which all of the double bonds have trans geometry except for that at the 9 position, which is cis. It is a 9-cis-epoxycarotenoid and a neoxanthin. Neoxanthin is a natural product found in Hibiscus syriacus, Cladonia rangiferina, and other organisms with data available. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Yezoquinolide

C27H34O4 (422.2457)

A natural product found particularly in Sargassum serratifolium and Botryllus tuberatus.

Cycloartenol

C30H50O (426.3861)

4-(3,7-dimethylocta-1,6-dien-3-yl)phenol

C16H22O (230.1671)

7-Phloroeckol

C24H16O12 (496.0642)

A phlorotannin that is eckol in which the hydroxy group at position 7 is replaced by a 2,4,6-trihydroxyphenoxy group. Isolated from the marine brown alga, Ecklonia cava, it exhibits antioxidant activity.

15-hydroxy-6,10,14-trimethylpentadeca-5,9,13-trien-2-one

C18H30O2 (278.2246)

Stypotriol

C27H40O4 (428.2926)

fucodiphloroethol G

C24H18O12 (498.0798)

A phlorotannin that consists of biphenyl-2,2,4,4,6-pentol substituted by a 2,4-dihydroxy-6-(2,4,6-trihydroxyphenoxy)phenoxy substituent at position 6. Isolated from the marine brown alga Ecklonia cava, it exhibits anti-allergic, antioxidant and hypoglycemic activities.

Bifuhalol

C12H10O7 (266.0427)

3,4-dibromo-5-(methoxymethyl)benzene-1,2-diol

C8H8Br2O3 (309.884)

methyl 3-bromo-4,5-dihydroxybenzoate

C8H7BrO4 (245.9528)

Spathulenol

C15H24O (220.1827)

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

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].

Dieckol

C36H22O18 (742.0806)

A phlorotannin isolated from a brown alga Ecklonia cava which exhibits antioxidant, hepatoprotective and anticoagulant activities. Dieckol, is a naturally occurring phlorotannin found in some brown algal species. Dieckol has anti-bacterial, anti-cancer, anti-oxidant, anti-aging, anti-diabetic, neuroprotective actions[1]. Dieckol, is a naturally occurring phlorotannin found in some brown algal species. Dieckol has anti-bacterial, anti-cancer, anti-oxidant, anti-aging, anti-diabetic, neuroprotective actions[1].

ethyl 9-(3-methyl-5-propylfuran-2-yl)nonanoate

C19H32O3 (308.2351)

ophthalmic acid

C11H19N3O6 (289.1274)

A L-glutamine derivative that is L-glutamine substituted by a 1-[(carboxymethyl)amino]-1-oxobutan-2-yl at the terminal amino nitrogen atom. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; JCMUOFQHZLPHQP-BQBZGAKWSA-N_STSL_0170_Ophthalmic acid_0500fmol_180425_S2_LC02_MS02_88; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I.

HEPTADEC-3-EN-2-ONE

C17H32O (252.2453)

3,4-Dibromo-5-(ethoxymethyl)benzene-1,2-diol

C9H10Br2O3 (323.8997)

2-Chlorobenzene-1,3,5-triol

C6H5ClO3 (159.9927)

Comosusol C

C16H22O2 (246.162)

A natural product found in Sporochnus comosus.

comosusol B

C16H22O3 (262.1569)

A natural product found in Sporochnus comosus.

comosusol A

C16H22O3 (262.1569)

A natural product found in Sporochnus comosus.

Comosusol D

C16H24O5 (296.1624)

A natural product found in Sporochnus comosus.

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].

6,10,14-trimethylpentadec-5-ene-2,12-dione

C18H32O2 (280.2402)

ethyl 9-(3,5-dimethylfuran-2-yl)nonanoate

C17H28O3 (280.2038)

Tetraphlorethol C

C24H18O12 (498.0798)

6,10,14-Trimethylpentadeca-5,10-diene-2,12-dione

C18H30O2 (278.2246)

Eckol

C18H12O9 (372.0481)

Eckol is a phlorotannin that is oxanthrene-1,3,6,8-tetrol substituted by a 3,5-dihydroxyphenoxy moiety at position 4. Isolated from the marine brown alga, Ecklonia cava, it exhibits antioxidant activity. It has a role as a metabolite and an antioxidant. It is functionally related to a phloroglucinol. Eckol is a natural product found in Ecklonia cava, Ecklonia maxima, and Eisenia bicyclis with data available. A phlorotannin that is oxanthrene-1,3,6,8-tetrol substituted by a 3,5-dihydroxyphenoxy moiety at position 4. Isolated from the marine brown alga, Ecklonia cava, it exhibits antioxidant activity.

1-(5-acetyl-2-hydroxy-4-methoxyphenyl)-3-methylbutan-1-one

C14H18O4 (250.1205)

nothoapiole

C13H16O5 (252.0998)

Phlorofucofuroeckol A

C30H18O14 (602.0697)

Diphlorethol

C12H10O6 (250.0477)

2,3-Dibromo-4,5-dihydroxybenzaldehyde

C7H4Br2O3 (293.8527)

2-bromobenzene-1,3,5-triol

C6H5BrO3 (203.9422)

3-tridecylphenol

C19H32O (276.2453)

6,10,14-trimethylpentadeca-5,9-diene-2,12-dione

C18H30O2 (278.2246)

6,10,14-TRIMETHYLPENTADECA-5,9-DIENE-2,13-DIONE

C18H30O2 (278.2246)

7-methylcycloocta-1,3,5-triene

C9H12 (120.0939)

2-bromo-4,5-dihydroxybenzaldehyde

C7H5BrO3 (215.9422)

Choline

[C5H14NO]+ (104.1075)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OEYIOHPDSNJKLS_STSL_0152_Choline_0125fmol_180430_S2_LC02_MS02_80; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D008082 - Lipotropic Agents D002491 - Central Nervous System Agents > D018697 - Nootropic Agents IPB_RECORD: 922; CONFIDENCE confident structure D009676 - Noxae > D000963 - Antimetabolites D005765 - Gastrointestinal Agents

Sorbitol

C6H14O6 (182.079)

A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AD - Osmotically acting laxatives A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AG - Enemas B - Blood and blood forming organs > B05 - Blood substitutes and perfusion solutions > B05C - Irrigating solutions V - Various > V04 - Diagnostic agents > V04C - Other diagnostic agents > V04CC - Tests for bile duct patency D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D005765 - Gastrointestinal Agents > D002400 - Cathartics CONFIDENCE standard compound; INTERNAL_ID 229 Acquisition and generation of the data is financially supported by the Max-Planck-Society D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1]. D-Sorbitol (Sorbitol) is a six-carbon sugar alcohol and can used as a sugar substitute. D-Sorbitol can be used as a stabilizing excipient and/or isotonicity agent, sweetener, humectant, thickener and dietary supplement[1].

Brassicasterol

C28H46O (398.3548)

An 3beta-sterol that is (22E)-ergosta-5,22-diene substituted by a hydroxy group at position 3beta. It is a phytosterol found in marine algae, fish, and rapeseed oil. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].

Campesterol

C28H48O (400.3705)

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. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects. Campesterol is a plant sterol with cholesterol lowering and anticarcinogenic effects.

Citrinin

C13H14O5 (250.0841)

CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 11 D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE Citrinin is a mycotoxin which causes contamination in the food and is associated with different toxic effects. Citrinin is usually found together with another nephrotoxic mycotoxin, Ochratoxin A. Citrinin is also reported to possess a broad spectrum of bioactivities, including antibacterial, antifungal, and potential anticancer and neuro-protective effects in vitro[1][2].

Abscisic Acid

C15H20O4 (264.1362)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.880 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.877 Abscisic acid ((S)-(+)-Abscisic acid), an orally active phytohormone in fruits and vegetables, is an endogenously produced mammalian hormone. Abscisic acid is a growth inhibitor and can regulate many aspects of plant growth and development. Abscisic acid inhibits proton pump (H+-ATPase) and leads to the plasma membrane depolarization in a Ca2+-dependent manner. Abscisic acid, a LANCL2 natural ligand, is a potent insulin-sensitizing compound and has the potential for pre-diabetes, type 2 diabetes and metabolic syndrome[1][2]. Abscisic acid ((S)-(+)-Abscisic acid), an orally active phytohormone in fruits and vegetables, is an endogenously produced mammalian hormone. Abscisic acid is a growth inhibitor and can regulate many aspects of plant growth and development. Abscisic acid inhibits proton pump (H+-ATPase) and leads to the plasma membrane depolarization in a Ca2+-dependent manner. Abscisic acid, a LANCL2 natural ligand, is a potent insulin-sensitizing compound and has the potential for pre-diabetes, type 2 diabetes and metabolic syndrome[1][2].

Levodopa

C9H11NO4 (197.0688)

relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.052

β-Carotene

C40H56 (536.4382)

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

L-alanine

C3H7NO2 (89.0477)

The L-enantiomer of alanine. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

Galactitol

C6H14O6 (182.079)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose. Dulcite is a sugar alcohol with a slightly sweet taste which is a metabolic breakdown product of galactose.

D-Alanine

C3H7NO2 (89.0477)

The D-enantiomer of alanine. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR.

PHENYLACETIC ACID

C8H8O2 (136.0524)

A monocarboxylic acid that is toluene in which one of the hydrogens of the methyl group has been replaced by a carboxy group. D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents

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

Phytol

C20H40O (296.3079)

Phytol is a key acyclic diterpene alcohol that is a precursor for vitamins E and K1. Phytol is an extremely common terpenoid, found in all plants esterified to Chlorophyll to confer lipid solubility[citation needed].; Phytol is a natural linear diterpene alcohol which is used in the preparation of vitamins E and K1. It is also a decomposition product of chlorophyll. It is an oily liquid that is nearly insoluble in water, but soluble in most organic solvents. -- Wikipedia C1907 - Drug, Natural Product > C28269 - Phytochemical Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1]. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1].

γ-Tocotrienol

C28H42O2 (410.3185)

γ-Tocotrienol is an active form of vitamin E. γ-tocotrienol reverses the multidrug resistance (MDR) of breast cancer cells through the signaling pathway of NF-κB and P-gp. γ-Tocotrienol is also a novel radioprotector agent, can mitigate bone marrow radiation damage during targeted radionuclide treatment[1][2][3]. γ-Tocotrienol is an active form of vitamin E. γ-tocotrienol reverses the multidrug resistance (MDR) of breast cancer cells through the signaling pathway of NF-κB and P-gp. γ-Tocotrienol is also a novel radioprotector agent, can mitigate bone marrow radiation damage during targeted radionuclide treatment[1][2][3].

PENTADECANOIC ACID

C15H30O2 (242.2246)

A straight-chain saturated fatty acid containing fifteen-carbon atoms. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone.

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.

Margaric acid

C17H34O2 (270.2559)

A C17 saturated fatty acid and trace component of fats in ruminants. Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1]. Heptadecanoic acid is an odd chain saturated fatty acid (OCS-FA). Heptadecanoic acid is associated with several diseases, including the incidence of coronary heart disease, prediabetes and type 2 diabetes as well as multiple sclerosis[1].

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.

Violaxanthin

C40H56O4 (600.4178)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Cucurbitachrome 1 is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Cucurbitachrome 1 is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cucurbitachrome 1 can be found in a number of food items such as italian sweet red pepper, herbs and spices, fruits, and red bell pepper, which makes cucurbitachrome 1 a potential biomarker for the consumption of these food products. (all-e)-violaxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone (all-e)-violaxanthin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (all-e)-violaxanthin can be found in a number of food items such as orange bell pepper, green bell pepper, passion fruit, and yellow bell pepper, which makes (all-e)-violaxanthin a potential biomarker for the consumption of these food products.

Cryptoxanthin

C40H56O (552.4331)

Isolated from papaya (Carica papaya) and many other higher plants, also from fish eggs [DFC]. beta-Cryptoxanthin is found in many foods, some of which are smelt, soy yogurt, common carp, and rose hip.

Zeaxanthin

C40H56O2 (568.428)

Meso-zeaxanthin (3R,3´S-zeaxanthin) is a xanthophyll carotenoid, as it contains oxygen and hydrocarbons, and is one of the three stereoisomers of zeaxanthin. Of the three stereoisomers, meso-zeaxanthin is the second most abundant in nature after 3R,3´R-zeaxanthin, which is produced by plants and algae. To date, meso-zeaxanthin has been identified in specific tissues of marine organisms and in the macula lutea, also known as the "yellow spot", of the human retina . Meso-zeaxanthin is a member of the class of compounds known as xanthophylls. Xanthophylls are carotenoids containing an oxygenated carotene backbone. Carotenes are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Xanthophylls arise by oxygenation of the carotene backbone. Meso-zeaxanthin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Meso-zeaxanthin can be found in channel catfish, crustaceans, and fishes, which makes meso-zeaxanthin a potential biomarker for the consumption of these food products. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Window width for selecting the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 16HP2005 to the Mass Spectrometry Society of Japan.

p-Hydroxybenzaldehyde

C7H6O2 (122.0368)

p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

Hordenine

C10H15NO (165.1154)

Annotation level-1 Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1]. Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1].

Alanine

C3H7NO2 (89.0477)

An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2. Alanine (symbol Ala or A),[4] or α-alanine, is an α-amino acid that is used in the biosynthesis of proteins. It contains an amine group and a carboxylic acid group, both attached to the central carbon atom which also carries a methyl group side chain. Consequently it is classified as a nonpolar, aliphatic α-amino acid. Under biological conditions, it exists in its zwitterionic form with its amine group protonated (as −NH + 3 ) and its carboxyl group deprotonated (as −CO − 2 ). It is non-essential to humans as it can be synthesized metabolically and does not need to be present in the diet. It is encoded by all codons starting with GC (GCU, GCC, GCA, and GCG). The L-isomer of alanine (left-handed) is the one that is incorporated into proteins. L-alanine is second only to L-leucine in rate of occurrence, accounting for 7.8\\\\\% of the primary structure in a sample of 1,150 proteins.[5] The right-handed form, D-alanine, occurs in peptides in some bacterial cell walls[6]: 131  (in peptidoglycan) and in some peptide antibiotics, and occurs in the tissues of many crustaceans and molluscs as an osmolyte. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. D-Alanine is a weak GlyR (inhibitory glycine receptor) and PMBA agonist, with an EC50 of 9 mM for GlyR. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system. L-Alanine is a non-essential amino acid, involved in sugar and acid metabolism, increases immunity, and provides energy for muscle tissue, brain, and central nervous system.

Eicosapentaenoic acid

C20H30O2 (302.2246)

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

loliolide

C11H16O3 (196.1099)

A natural product found in Brachystemma calycinum.

D-Xylose

C5H10O5 (150.0528)

D-Xylose is a flavouring ingredient; sweetener. It is found in straw, corncobs, pecan shells, carrot, dandelion, german camomile, and sweet orange. D-Xylose is a sugar first isolated from wood, and named for it. D-Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional group. It is the precursor to hemicellulose, one of the main constituents of biomass (Wikipedia). Xylose in the urine is a biomarker for the consumption of fruits. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose.

α-Linolenic acid

C18H30O2 (278.2246)

α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

VITAMIN E

C29H50O2 (430.3811)

Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 40 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants D018977 - Micronutrients > D014815 - Vitamins 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 15 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. DL-alpha-Tocopherol is a synthetic vitamin E, with antioxidation effect. DL-alpha-Tocopherol protects human skin fibroblasts against the cytotoxic effect of UVB[1]. DL-alpha-Tocopherol is a synthetic vitamin E, with antioxidation effect. DL-alpha-Tocopherol protects human skin fibroblasts against the cytotoxic effect of UVB[1]. rel-α-Vitamin E (rel-D-α-Tocopherol) is a vitamin with antioxidant properties and also a mixture[1]. α-Vitamin E ((+)-α-Tocopherol), a naturally occurring vitamin E form, is a potent antioxidant[1][2]. α-Vitamin E ((+)-α-Tocopherol), a naturally occurring vitamin E form, is a potent antioxidant[1][2].

dihomo-gamma-linolenic acid

C20H34O2 (306.2559)

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

4-Hydroxybenzaldehyde

C7H6O2 (122.0368)

p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations. p-Hydroxybenzaldehyde is a one of the major components in vanilla aroma, with antagonistic effect on GABAA receptor of the α1β2γ2S subtype at high concentrations.

Fucoxanthin

C42H58O6 (658.4233)

Fucoxanthin is an epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties. It has a role as an algal metabolite, a CFTR potentiator, a food antioxidant, a neuroprotective agent, a hypoglycemic agent, an apoptosis inhibitor, a hepatoprotective agent, a marine metabolite and a plant metabolite. It is an epoxycarotenol, an acetate ester, a secondary alcohol, a tertiary alcohol and a member of allenes. Fucoxanthin is a natural product found in Aequipecten opercularis, Ascidia zara, and other organisms with data available. An epoxycarotenol that is found in brown seaweed and which exhibits anti-cancer, anti-diabetic, anti-oxidative and neuroprotective properties. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Window width to select the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Window width for selecting the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 16HP2005 to the Mass Spectrometry Society of Japan. Fucoxanthin (all-trans-Fucoxanthin) is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities[1][2][3][4][5][6][7][8][9]. Fucoxanthin is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities. Fucoxanthin (all-trans-Fucoxanthin) is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities[1][2][3][4][5][6][7][8][9]. Fucoxanthin is a marine carotenoid and shows anti-obesity, anti-diabetic, anti-oxidant, anti-inflammatory and anticancer activities.

phloroglucinol

C6H6O3 (126.0317)

A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03A - Drugs for functional gastrointestinal disorders D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents A benzenetriol with hydroxy groups at position 1, 3 and 5.

HEPTADECANOIC ACID

C17H34O2 (270.2559)

3-Hydroxybutanoic acid

C4H8O3 (104.0473)

L-Fucose

C6H12O5 (164.0685)

(-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.

Hexadecanoic acid

C16H32O2 (256.2402)

Tetradecanoic acid

C14H28O2 (228.2089)

Choline

C5H14NO (104.1075)

Desmosterol

C27H44O (384.3392)

Fucose

C6H12O5 (164.0685)

(-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions. (-)-Fucose is classified as a member of the hexoses, plays a role in A and B blood group antigen substructure determination, selectin-mediated leukocyte-endothelial adhesion, and host-microbe interactions.

Choline

C5H14NO+ (104.1075)

A choline that is the parent compound of the cholines class, consisting of ethanolamine having three methyl substituents attached to the amino function. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D008082 - Lipotropic Agents D002491 - Central Nervous System Agents > D018697 - Nootropic Agents D009676 - Noxae > D000963 - Antimetabolites D005765 - Gastrointestinal Agents

Geranylacetone

C13H22O (194.1671)

Choline

C5H13NO (103.0997)

Nonanal

C9H18O (142.1358)

Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1]. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1].

24-oxocholesterol

C27H44O2 (400.3341)

Dormin

C15H20O4 (264.1362)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids D006133 - Growth Substances > D010937 - Plant Growth Regulators (±)-Abscisic acid is an orally active plant hormone that is present also in animals. (±)-Abscisic acid (ABA) contributes to the regulation of glycemia in mammals[1]. (±)-Abscisic acid is an orally active plant hormone that is present also in animals. (±)-Abscisic acid (ABA) contributes to the regulation of glycemia in mammals[1]. Abscisic acid ((S)-(+)-Abscisic acid), an orally active phytohormone in fruits and vegetables, is an endogenously produced mammalian hormone. Abscisic acid is a growth inhibitor and can regulate many aspects of plant growth and development. Abscisic acid inhibits proton pump (H+-ATPase) and leads to the plasma membrane depolarization in a Ca2+-dependent manner. Abscisic acid, a LANCL2 natural ligand, is a potent insulin-sensitizing compound and has the potential for pre-diabetes, type 2 diabetes and metabolic syndrome[1][2]. Abscisic acid ((S)-(+)-Abscisic acid), an orally active phytohormone in fruits and vegetables, is an endogenously produced mammalian hormone. Abscisic acid is a growth inhibitor and can regulate many aspects of plant growth and development. Abscisic acid inhibits proton pump (H+-ATPase) and leads to the plasma membrane depolarization in a Ca2+-dependent manner. Abscisic acid, a LANCL2 natural ligand, is a potent insulin-sensitizing compound and has the potential for pre-diabetes, type 2 diabetes and metabolic syndrome[1][2].

1-OCTEN-3-OL

C8H16O (128.1201)

Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2]. Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2].

CADALENE

C15H18 (198.1408)

(-)-Amijiol

C20H32O2 (304.2402)

(-)-Isoamijiol

C20H32O2 (304.2402)

Spatol

C20H30O3 (318.2195)

PENTADECANAL

C15H30O (226.2297)

A long-chain fatty aldehyde that is pentadecane carrying an oxo substituent at position 1. It is a component of essential oils from plants like Solanum erianthum and Cassia siamea.

D-Amorphene

C15H24 (204.1878)

2-Pentadecanone

C15H30O (226.2297)

Dihydroactinidiolide

C11H16O2 (180.115)

(±)-Dihydroactinidiolide, an important aroma compound of black tea and tobacco, has been isolated from several plants. (±)-Dihydroactinidiolide can be formation from β-Carotene by the treatment of polyphenoloxidase, the lipoxygenase, and the xanthine oxidase[1][2]. (±)-Dihydroactinidiolide, an important aroma compound of black tea and tobacco, has been isolated from several plants. (±)-Dihydroactinidiolide can be formation from β-Carotene by the treatment of polyphenoloxidase, the lipoxygenase, and the xanthine oxidase[1][2].

Beta-Elemene

C15H24 (204.1878)

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

Yatansin

C15H24 (204.1878)

1-Epibicyclosesquiphellandrene

C15H24 (204.1878)

epicubenol

C15H26O (222.1984)

g-Muurolene

C15H24 (204.1878)

β-Cyclocitral

C10H16O (152.1201)

A monoterpenoid formally derived from citral by cyclisation. It is a volatile compound produced by a cyanobacteria.

1,2-Di-O-palmitoyl-3-O-(6-sulfoquinovopyranosyl)glycerol

C41H78O12S (794.5214)

FAL 13:0

C13H26O (198.1984)

Pentadecane

C15H32 (212.2504)

A straight-chain alkane with 15 carbon atoms. It is a component of volatile oils isolated from plants species like Scandix balansae.

1-PENTADECENE

C15H30 (210.2347)

An unbranched fifteen-carbon alkene with one double bond between C-1 and C-2.

Heptadecan-2-one

C17H34O (254.261)

Pentadecan-2-one

C15H30O (226.2297)

Saringosterol

C29H48O2 (428.3654)

2-aminoethanesulfonic acid

C2H7NO3S (125.0147)

D-Sorbitol

C6H14O6 (182.079)

D-(1-(13)C)glucitol

C6H14O6 (182.079)

(2R)-2-aminopropanoic acid

C3H7NO2 (89.0477)

D(+)-Glucose

C6H12O6 (180.0634)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents

N-(2-Hydroxyethyl)glycine

C4H9NO3 (119.0582)

piperidine-2-carboxylic acid

C6H11NO2 (129.079)

1-Bromopentane

C5H11Br (150.0044)

L-Guluronic acid

C6H10O7 (194.0427)

Phenol, 3-tridecyl-

C19H32O (276.2453)

n-trimethyllysine

C9H21N2O2+ (189.1603)

D050258 - Mitosis Modulators > D008934 - Mitogens

β-Ionone

C13H20O (192.1514)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids β-Ionone is effective in the induction of apoptosis in gastric adenocarcinoma SGC7901 cells. Anti-cancer activity[1]. β-Ionone is effective in the induction of apoptosis in gastric adenocarcinoma SGC7901 cells. Anti-cancer activity[1].

tetrachloroethane

C2H2Cl4 (165.8911)

Fructon

C6H12O6 (180.0634)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents D-Fructose (D(-)-Fructose) is a naturally occurring monosaccharide found in many plants. D-Fructose (D(-)-Fructose) is a naturally occurring monosaccharide found in many plants.

CHEBI:15385

C15H24 (204.1878)

Hexanol

C6H14O (102.1045)

D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists

maltodextrin

C6H12O6 (180.0634)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents

Dodecanal

C12H24O (184.1827)

Apiol

C12H14O4 (222.0892)

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

C28H42O2 (410.3185)

Plastoquinone

C53H80O2 (748.6158)

(-)-Germacrene A

C15H24 (204.1878)

Comosone A

C16H24O2 (248.1776)

A natural product found in Sporochnus comosus.

dilopholide

C22H32O4 (360.23)

A diterpenoid isolated from the brown alga Dilophus ligulatus and has been shown to exhibit cytotoxic activity.

(2E,6Z)-13-hydroxy-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,14-triene-5,12-dione

C28H40O5 (456.2876)

A meroterpenoid that is hexadeca-2,6,14-triene-5,12-dione substituted by a hydroxy group at position 13, a 2-hydroxy-5-methoxy-3-methylphenyl group at position 1 and methyl groups at positions 3, 7, 11 and 15. Isolated from Halidrys siliquosa, it exhibits antibacterial and antifouling activities.

(10E,14E)-5-hydroxy-16-(2-hydroxy-5-methoxy-3-methylphenyl)-2,6,10,14-tetramethylhexadeca-2,10,14-triene-4,12-dione

C28H40O5 (456.2876)

(2E,6E)-13-Hydroxy-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,14-triene-5,12-dione

C28H40O5 (456.2876)

Plastoquinone 1

C27H42O4 (430.3083)

A natural product found in Sargassum micracanthum.

Plastoquinone 2

C27H40O4 (428.2926)

A natural product found in Sargassum micracanthum.

Epicubebol methyl ether

C16H28O (236.214)

A natural product found in Neolitsea daibuensis.

Dehydrovomifoliol

C13H18O3 (222.1256)

(6S)-dehydrovomifoliol is a dehydrovomifoliol that has S-configuration at the chiral centre. It has a role as a plant metabolite. It is an enantiomer of a (6R)-dehydrovomifoliol. Dehydrovomifoliol is a natural product found in Psychotria correae, Dendrobium loddigesii, and other organisms with data available.

1,1,2,2-TETRACHLOROETHANE

C2H2Cl4 (165.8911)

(+)-gamma-cadinene

C15H24 (204.1878)

A member of the cadinene family of sesquiterpenes in which the isopropyl group is cis to the hydrogen at the adjacent bridgehead carbon (the 1S,4aR,8aR enantiomer).

Ectocarpene

C11H16 (148.1252)

2-HEPTADECANONE

C17H34O (254.261)

MESITYL OXIDE

C6H10O (98.0732)

Hexachlorobutadiene

C4Cl6 (257.8131)

D016573 - Agrochemicals D010575 - Pesticides

Dihydrocholesterol

C27H48O (388.3705)

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

1-PENTEN-3-OL

C5H10O (86.0732)

galbanum decatriene

C11H18 (150.1408)

delta-Cadinol

C15H26O (222.1984)

Antimycin

C13H14O5 (250.0841)

Eckstolonol

C18H10O9 (370.0325)

A phlorotannin that is [1,4]benzodioxino[2,3-a]oxanthrene substituted by hydroxy groups at positions 1, 3, 6, 9 and 11. Isolated from the brown alga Ecklonia stolonifera, it exhibits radical scavenging activity.

Dolabellane analog-8

C20H32O (288.2453)

A natural product found in Dilophus spiralis.

(S)-Sargachromenol

C27H36O4 (424.2613)

A natural product found in Botryllus tuberatus.

(R)-Sargachromenol

C27H36O4 (424.2613)

A natural product found in Botryllus tuberatus.

Avenasterol

C29H48O (412.3705)

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

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

C20H32O2 (304.2402)

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

delta-Cadinene

C15H24 (204.1878)

A member of the cadinene family of sesquiterpenes in which the double bonds are located at the 4-4a and 7-8 positions, and in which the isopropyl group at position 1 is cis to the hydrogen at the adjacent bridgehead carbon (position 8a).

(6Z,9Z,12Z,15Z)-henicosa-1,6,9,12,15-pentaene

C21H34 (286.266)

An alkapentaene that is henicos-1-ene with 4 cis double bonds at positions 6,9,12 and 15.

(6Z,9Z,12Z,15Z)-tricosa-1,6,9,12,15-pentaene

C23H38 (314.2973)

An alkapentaene that is tricos-1-ene with 4 cis double bonds at positions 6,9,12 and 15.

D-Fructopyranose

C6H12O6 (180.0634)

A fructopyranose having D-configuration.

keto-D-fructose

C6H12O6 (180.0634)

The open-chain form of D-fructose.

Hexan-1-ol

C6H14O (102.1045)

A primary alcohol that is hexane substituted by a hydroxy group at position 1.

aldehydo-L-fucose

C6H12O5 (164.0685)

Dolabellane analog-7

C20H30O2 (302.2246)

A natural product found in Dilophus spiralis.

Oct-1-en-3-ol

C8H16O (128.1201)

An alkenyl alcohol with a structure based on a C8 unbranched chain with the hydroxy group at C-2 and unsaturation at C-1-C-2. It is a major volatile compound present in many mushrooms and fungi.

(4ar,5r,8s,8ar)-4a-hydroxy-8-isopropyl-5-methyl-4,5,6,7,8,8a-hexahydro-3h-naphthalene-2-carbaldehyde

C15H24O2 (236.1776)

(1s,3ar,4ar,8s,8as,10as)-3a,8a-dimethyl-5-methylidene-1-(prop-1-en-2-yl)-decahydro-1h-cyclohexa[f]azulen-8-ol

C20H32O (288.2453)

2-[4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-4-(2-hydroxypropan-2-yl)-6a,9a-dimethyl-4h,5h,7h,8h,9h-cyclopenta[d]oxocin-6-one

C28H40O5 (456.2876)

(4e,7s)-n-[(2e)-3-chloro-2-[(5s)-2,5-dimethyl-6-oxocyclohex-1-en-1-yl]prop-2-en-1-yl]-7-methoxydodec-4-enimidic acid

C24H38ClNO3 (423.254)

3,5-bis(acetyloxy)-2-[3,5-bis(acetyloxy)-4-[3,4,5-tris(acetyloxy)-2-[3,5-bis(acetyloxy)-4-[3,4,5-tris(acetyloxy)phenoxy]phenoxy]phenoxy]phenoxy]phenyl acetate

C56H48O30 (1200.223)

1,3,3-trimethyl-2-[(9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohex-1-ene

C40H56 (536.4382)

(5e)-8-[(1r,5s)-5-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-6-methyloct-5-en-2-one

C18H30O2 (278.2246)

2-[(2e,6e,9e,11s)-11-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,9,14-tetraen-1-yl]-6-methylbenzene-1,4-diol

C27H40O3 (412.2977)

(10e,14e)-4,12-dihydroxy-16-(2-hydroxy-5-methoxy-3-methylphenyl)-2,6,10,14-tetramethylhexadeca-2,10,14-trien-5-one

C28H42O5 (458.3032)

3-(14,15-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10-trien-1-yl)-4-hydroxy-5-methylphenyl octadec-9-enoate

C45H74O5 (694.5536)

10-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-3,7-dimethyl-2-(2-methylprop-1-en-1-yl)deca-3,7-dienoic acid

C27H38O4 (426.277)

(4r,5s,10s)-13-[(2r)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,6-diene-4,5,10-triol

C27H42O5 (446.3032)

2-methoxy-11-methyl-7-(4-methylpent-3-en-1-yl)-3,5-dioxatricyclo[6.6.1.0⁴,¹⁵]pentadeca-1(14),11-diene

C21H32O3 (332.2351)

(6e,10e,14e)-2,16-dihydroxy-2,6,10,14-tetramethylhexadeca-6,10,14-trien-4-one

C20H34O3 (322.2508)

9-hydroxy-6,10-dimethyl-10-(4-methyl-3-oxopentyl)-2-methylidene-12-oxatricyclo[7.2.1.0¹,⁶]dodecan-5-yl acetate

C22H34O5 (378.2406)

(6e,14e)-16-hydroxy-2,6,14-trimethyl-10-methylidenehexadeca-2,6,14-triene-4,11-dione

C20H30O3 (318.2195)

(2r,3r,4r,5r)-6-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexane-1,2,3,4,5-pentol

C12H24O11 (344.1319)

4-[(3e,7e,10s)-10-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,6-dioxabicyclo[3.1.0]hexan-3-one

C20H30O4 (334.2144)

3-(acetyloxy)-5-{[4,7,9-tris(acetyloxy)-2-[2,4,6-tris(acetyloxy)phenoxy]oxanthren-1-yl]oxy}phenyl acetate

C40H32O20 (832.1487)

2,4,5-trihydroxy-3-methoxyhexanal

C7H14O5 (178.0841)

(4e,8e,12e,16e)-4,8,13,17,21-pentamethyldocosa-4,8,12,16,20-pentaenoic acid

C27H44O2 (400.3341)

12-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenal

C20H32O2 (304.2402)

2-{7-[6-(2-hydroxypropan-2-yl)-2-oxooxan-3-ylidene]-4-methylhept-3-en-1-yl}-2,6-dimethylchromene-5,8-dione

C27H34O6 (454.2355)

[(1r,2e,5e,9r)-2-formyl-6-methyl-9-[(2s)-6-methylhept-5-en-2-yl]cyclonona-2,5-dien-1-yl]methyl acetate

C22H34O3 (346.2508)

2-[(1r,3ar,6r,7r,8r,12s,12as)-7,8,12-tris(acetyloxy)-3a,6,10-trimethyl-1h,2h,3h,6h,7h,8h,11h,12h,12ah-cyclopenta[11]annulen-1-yl]propan-2-yl acetate

C28H42O8 (506.288)

(5e,10e,14e)-16-hydroxy-2,6,10,14-tetramethylhexadeca-2,5,10,14-tetraen-4-one

C20H32O2 (304.2402)

17-ethyl-13,18-dioxatricyclo[12.4.0.0²,¹⁶]octadeca-3,6-dien-12-one

C18H26O3 (290.1882)

3-{5-[(2,5-dihydroxy-3-methylphenyl)methyl]-5,6,8a-trimethyl-2-oxo-hexahydro-1h-naphthalen-1-yl}propanoic acid

C24H34O5 (402.2406)

(3r,3as,7r,7as)-7-hydroxy-7a-methyl-3-[(2s)-6-methylhept-5-en-2-yl]-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde

C20H30O3 (318.2195)

(1r,2z,5e,9r)-2,6-dimethyl-9-[(2r)-6-methylhept-5-en-2-yl]cyclonona-2,5-diene-1-carboxylic acid

C20H32O2 (304.2402)

2,8-dimethyl-5-(3,6,7-trihydroxy-6-methylhepta-1,4-dien-2-yl)tricyclo[5.3.0.0²,⁶]decan-3-one

C20H30O4 (334.2144)

6-(4-hydroxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydro-1h-azulen-5-yl)-2-methylhept-2-en-4-yl acetate

C22H34O3 (346.2508)

(2r,3as,6s,7as)-2,3a-dihydroxy-4,4,7a-trimethyl-3-oxo-tetrahydro-1-benzofuran-6-yl acetate

C13H20O6 (272.126)

3-{5-[(2-hydroxy-5-methoxy-3-methylphenyl)methyl]-5,6,8a-trimethyl-2-oxo-hexahydro-1h-naphthalen-1-yl}propanoic acid

C25H36O5 (416.2563)

(1s,2r,3r,5r,6r,7r,8r)-5-[(4e)-6-hydroxy-6-methylhepta-1,4-dien-2-yl]-2,8-dimethyltricyclo[5.3.0.0²,⁶]decan-3-ol

C20H32O2 (304.2402)

16-(2,5-dihydroxy-3-methylphenyl)-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraene-4,12-dione

C27H36O4 (424.2613)

(2e)-7-hydroxy-5-methyl-2-[(4z,7z,10z,13z,16z)-nonadeca-4,7,10,13,16-pentaen-1-ylidene]-3h-1-benzopyran-4-one

C29H36O3 (432.2664)

3-{[(1r,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxybenzoic acid

C22H30O3 (342.2195)

1,3-dimethoxy-7-methyl-4-(6-methylhept-5-en-2-yl)-1h,3h,3ah,4h,5h,6h,9h-cyclonona[c]furan

C22H36O3 (348.2664)

7-hydroxy-1-(2-hydroxy-6-methyl-5-methylideneheptan-2-yl)-9a,11a-dimethyl-1h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-2-one

C28H44O3 (428.329)

(4as,12bs)-4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione

C21H24O2 (308.1776)

(3ar,4as,8r,8as)-8a-(hydroxymethyl)-1-isopropyl-3a-methyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h,10h-cyclohexa[f]azulene-4a,8-diol

C20H32O3 (320.2351)

(1s,3ar,4ar,8s,8as,10as)-3a,5,8a-trimethyl-1-(prop-1-en-2-yl)-1h,2h,3h,4h,4ah,7h,8h,9h,10h,10ah-cyclohexa[f]azulen-8-ol

C20H32O (288.2453)

13-hydroxy-6,10,14-trimethylpentadeca-5,9,14-trien-2-one

C18H30O2 (278.2246)

(1r,2s,5r,6r,7s,8s)-1,5,8-trimethyl-8-[(2z)-6-methylhepta-2,5-dien-2-yl]tricyclo[5.3.0.0²,⁶]decane

C21H34 (286.266)

(2e,6z,13e)-15-hydroxy-1-(5-hydroxy-2-methoxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,13-triene-5,12-dione

C28H40O5 (456.2876)

5-[2,6-dihydroxy-4-(2,4,6-trihydroxyphenoxy)phenoxy]-4-{4-[2-(4-{2-[4-(2-{3,5-dihydroxy-4-[3,4,5-trihydroxy-2-(3,4,5-trihydroxyphenoxy)phenoxy]phenoxy}-3,4,5-trihydroxyphenoxy)-3,5-dihydroxyphenoxy]-3,4,5-trihydroxyphenoxy}-2,3-dihydroxyphenoxy)-3,4,5-trihydroxyphenoxy]-3,5-dihydroxyphenoxy}benzene-1,2,3-triol

C72H50O42 (1586.1777)

(1r,3as,4r,5s,8ar)-3-methyl-5-[(2r)-6-methylhept-5-en-2-yl]-8-methylidene-3a,4,5,6,7,8a-hexahydro-1h-azulene-1,4-diol

C20H32O2 (304.2402)

2,3-dihydroxypropoxy(3-({5-[(dimethylarsoryl)methyl]-3,4-dihydroxyoxolan-2-yl}oxy)-2-hydroxypropyl)phosphinic acid

C13H28AsO11P (466.0585)

10-hydroxy-1,1,4a,6a,8,12b-hexamethyl-3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthen-2-one

C27H38O3 (410.2821)

2,16-dihydroxy-2,6,10,14-tetramethylhexadeca-6,10,14-trien-4-one

C20H34O3 (322.2508)

4-(6-hydroxy-3,7-dimethylocta-1,7-dien-3-yl)phenol

C16H22O2 (246.162)

(3r,3as,7s,7as)-7-hydroxy-3-[(2s,5r)-5-hydroxy-6-methylhept-6-en-2-yl]-7a-methyl-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde

C20H30O4 (334.2144)

(2's,4'ar,4'bs,7's,8'ar)-2',4'b,7,8',8',10'a-hexamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthrene]-4,5,7'-triol

C27H40O4 (428.2926)

(3ar,6r,7as)-3a,6-dihydroxy-4,4,7a-trimethyl-tetrahydro-1-benzofuran-2-one

C11H18O4 (214.1205)

4,12-dihydroxy-16-(2-hydroxy-5-methoxy-3-methylphenyl)-2,6,10,14-tetramethylhexadeca-2,10,14-trien-5-one

C28H42O5 (458.3032)

sargachromanol d

C27H40O4 (428.2926)

(1r,3ar,4as,8r,8ar)-1,4a-dihydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate

C22H34O4 (362.2457)

3,5-bis(acetyloxy)-2-[3,4,5-tris(acetyloxy)-2-[3,5-bis(acetyloxy)-4-[3,4,5-tris(acetyloxy)-2-[3,5-bis(acetyloxy)-4-[3,4,5-tris(acetyloxy)phenoxy]phenoxy]phenoxy]phenoxy]phenoxy]phenyl acetate

C68H58O37 (1466.2657)

methyl 2-(5-hydroxy-2-{[(6e,13r)-13-hydroxy-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,14-trien-3-yl]oxy}phenyl)acetate

C29H42O6 (486.2981)

(4ar,5r,8s)-4a-hydroxy-8-isopropyl-5-methyl-3,4,5,6,7,8-hexahydronaphthalen-2-one

C14H22O2 (222.162)

3-[(6-carboxy-3,4-dihydroxyoxan-2-yl)oxy]-4,5,6-trihydroxyoxane-2-carboxylic acid

C12H18O12 (354.0798)

2,3,5-tris(acetyloxy)phenyl acetate

C14H14O8 (310.0689)

12-[(2e)-4-(2,5-dihydroxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-10-hydroxy-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodec-1(12)-en-2-one

C27H38O5 (442.2719)

sargachromanol

C22H30O3 (342.2195)

methyl 12-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoate

C21H34O3 (334.2508)

13,14-dihydroxy-6,10,14-trimethylpentadeca-5,9-dien-2-one

C18H32O3 (296.2351)

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-[(1r,6r,7s)-2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl]-4-methylhex-4-en-2-one

C27H36O5 (440.2563)

(1s,14as,15r,16r,17ar)-16-chloro-1-ethyl-15-hydroxy-1h,4h,5h,6h,9h,12h,14ah,15h,16h,17h,17ah-cyclopenta[c]oxacyclohexadecan-3-one

C20H29ClO3 (352.1805)

methyl 3-[(1s,4ar,5s,6s,8ar)-5-[(2,5-dihydroxy-3-methylphenyl)methyl]-5,6,8a-trimethyl-2-(propan-2-ylidene)-hexahydro-1h-naphthalen-1-yl]propanoate

C28H42O4 (442.3083)

(6z,9z)-10-[(1r,3r,4r,6r,7s)-6-chloro-3-ethyl-2-oxabicyclo[2.2.1]heptan-7-yl]deca-6,9-dienoic acid

C18H27ClO3 (326.1649)

2-(6-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-2,8-dimethylchromen-6-ol

C27H38O3 (410.2821)

(2e,10e)-1-(2,5-dihydroxy-3-methylphenyl)-16-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one

C27H38O4 (426.277)

(2s)-6-methoxy-2,8-dimethyl-2-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-1-benzopyran

C28H42O2 (410.3185)

4,4'-bis(2,4,6-trihydroxyphenoxy)-[1,1'-biphenyl]-2,2',6,6'-tetrol

C24H18O12 (498.0798)

(3s,9r,12as)-3,9-dihydroxy-3-isopropyl-6,10,12a-trimethyl-1h,2h,3ah,4h,8h,9h,12h-cyclopenta[11]annulen-5-one

C20H32O3 (320.2351)

5'-[(2e)-4-(5-hydroxy-2-methoxy-3-methylphenyl)but-2-en-2-yl]-3'a,5,5,7'a-tetramethyl-2',3',5',7'-tetrahydro-1'h-spiro[furan-2,4'-inden]-6'-one

C28H38O4 (438.277)

10-{6-chloro-3-ethyl-2-oxabicyclo[2.2.1]heptan-7-yl}deca-6,9-dienoic acid

C18H27ClO3 (326.1649)

3-[4-(2-{4-[2-(3,5-dihydroxyphenoxy)-3,5-dihydroxyphenoxy]-3,5-dihydroxyphenoxy}-3,5-dihydroxyphenoxy)-3,5-dihydroxyphenoxy]-[1,1'-biphenyl]-2,2',4,4',6,6'-hexol

C42H30O21 (870.128)

(2e,6e,11r)-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,14-triene-5,12-dione

C28H40O4 (440.2926)

5-(but-2-enoyl)-4-methoxy-6-methylpyran-2-one

C11H12O4 (208.0736)

3,8-dimethyl-5-(6-methylhept-5-en-2-yl)-1,3a,4,5,6,8a-hexahydroazulen-4-ol

C20H32O (288.2453)

2-[(2e,6e,10e,12s)-12-hydroxy-11-(hydroxymethyl)-3,7,15-trimethylhexadeca-2,6,10,14-tetraen-1-yl]-6-methylbenzene-1,4-diol

C27H40O4 (428.2926)

(1s,5e,9s)-6-methyl-2-methylidene-9-(prop-1-en-2-yl)cyclodec-5-en-1-ol

C15H24O (220.1827)

2-[(2z,6e,9r,10e)-8,9-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

C27H38O4 (426.277)

2-[(2e,6e,9r,10e)-9-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

C27H38O3 (410.2821)

5-(10-hydroxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-2,6-dioxabicyclo[3.1.0]hexan-3-one

C20H30O4 (334.2144)

3-[(5-{[6-carboxy-4,5-dihydroxy-3-(sulfooxy)oxan-2-yl]oxy}-6-(hydroxymethyl)-3-(sulfoamino)-4-(sulfooxy)oxan-2-yl)oxy]-6-({4,6-dihydroxy-5-[(1-hydroxyethylidene)amino]-2-[(sulfooxy)methyl]oxan-3-yl}oxy)-4-hydroxy-5-(sulfooxy)oxane-2-carboxylic acid

C26H42N2O37S5 (1134.007)

3,4,7,8-tetrabromo-9,10-dimethoxy-9,10-dihydroanthracene-1,2,5,6-tetrol

C16H12Br4O6 (615.7367)

(3s,4r,5r)-4,5-dihydroxy-3-[(3e,7e)-4,8,12-trimethyl-10-oxotrideca-3,7,11-trien-1-yl]oxolan-2-one

C20H30O5 (350.2093)

9-hydroxy-6,10-dimethyl-10-(4-methyl-3-oxopentyl)-2-methylidene-12-oxatricyclo[7.2.1.0¹,⁶]dodecan-5-one

C20H30O4 (334.2144)

1-ethyl-13-hydroxy-14-iodo-1h,4h,5h,6h,7h,10h,12ah,13h,14h,15h,15ah-cyclopenta[c]oxacyclotetradecan-3-one

C18H27IO3 (418.1005)

(2e,6r,10e,13r)-3,11,15-trimethyl-7-methylidenehexadeca-2,10,14-triene-1,6,13-triol

C20H34O3 (322.2508)

9-(3,5-dihydroxyphenoxy)-8-(2,4,6-trihydroxyphenoxy)oxanthrene-1,3,6-triol

C24H16O12 (496.0642)

6-[(3e,5e,7e,9e)-18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,3-diol

C40H56O4 (600.4178)

6,10,12a-trimethyl-3-(prop-1-en-2-yl)-2h,3h,3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one

C20H30O (286.2297)

(2r,5r,6r,8r)-5-[(4s)-4-hydroxy-6-methylhepta-1,5-dien-2-yl]-2,8-dimethyltricyclo[5.3.0.0²,⁶]decan-3-ol

C20H32O2 (304.2402)

3-[(4-hydroxyphenyl)methyl]-1,4-dimethyl-3,6-bis(methylsulfanyl)piperazine-2,5-dione

C15H20N2O3S2 (340.0915)

tetrafucol a

C24H18O12 (498.0798)

1,5-dimethyl-8-(prop-1-en-2-yl)cyclodeca-1,5-diene

C15H24 (204.1878)

(4s,4ar,5s,11ar)-5-hydroxy-7-methyl-4-(4-methylpent-3-en-1-yl)-1-oxo-3h,4h,4ah,5h,6h,9h,11ah-cyclonona[c]pyran-11-carbaldehyde

C20H28O4 (332.1987)

(3ar,8r,8as)-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,6h,7h,8h,9h,10h-cyclohexa[f]azulen-8-ol

C20H30O (286.2297)

(4e)-5-[(1s)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]-3-methylpenta-2,4-dienoic acid

C15H20O4 (264.1362)

2-[(4e,8e)-10-(5-hydroxy-2-methoxy-3-methylphenyl)-4,8-dimethyl-6-oxodeca-4,8-dien-1-yl]-2,6,6-trimethylpyran-3-one

C28H38O5 (454.2719)

1-(2,6-dihydroxy-4-methoxyphenyl)octadeca-6,9,12,15-tetraen-1-one

C25H34O4 (398.2457)

1-(2,5-dihydroxy-3-methylphenyl)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one

C27H38O3 (410.2821)

(4e)-6-(2,5-dimethoxy-3-methylphenyl)-1-[(1s,2s)-2-(4-hydroxy-4-methylpentanoyl)-1,2-dimethylcyclopentyl]-4-methylhex-4-en-2-one

C29H44O5 (472.3189)

(1r,3r,3ar,4r)-1,3-dimethoxy-7-methyl-4-[(2r)-6-methylhept-5-en-2-yl]-1h,3h,3ah,4h,5h,6h,9h-cyclonona[c]furan

C22H36O3 (348.2664)

7-methyl-4-(6-methylhept-5-en-2-yl)-4h,5h,6h,9h,10h-cyclonona[c]furan

C20H30O (286.2297)

5-hydroxy-1-(5-isopropylhept-5-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

C29H46O2 (426.3498)

(2r)-2,8-dimethyl-2-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]chromen-6-ol

C27H38O2 (394.2872)

(6z,8e,10s,12z,15z)-10-hydroxyoctadeca-6,8,12,15-tetraenoic acid

C18H28O3 (292.2038)

(3s,3as,12ar)-6,10,12a-trimethyl-3-(prop-1-en-2-yl)-2h,3h,3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-one

C20H30O (286.2297)

2-[(2e,6e,8r,9r,10e)-8,9-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

C27H38O4 (426.277)

1-[(1r,6s,7r)-2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl]-3-[(2r)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]propan-2-one

C27H36O5 (440.2563)

(3as,4ar,8s,8as)-1-isopropyl-3a,8a-dimethyl-5-methylidene-2h,3h,4h,6h,7h,8h,9h,10h-cyclohexa[f]azulene-4a,8-diol

C20H32O2 (304.2402)

(3e,7e,11e)-13-(2,5-dimethoxy-3-methylphenyl)-1-(3,3-dimethyloxiran-2-yl)-3,7,11-trimethyltrideca-3,7,11-triene-2,9-diol

C29H44O5 (472.3189)

(1r,2s,3r)-3-[(1s,5r)-2-formyl-5-[(2z)-6-methylhepta-2,5-dien-2-yl]cyclopent-2-en-1-yl]-2-methyl-4-oxocyclopentyl acetate

C22H30O4 (358.2144)

7-hydroxy-7a-methyl-3-(6-methylhept-5-en-2-yl)-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde

C20H30O3 (318.2195)

(2r,3e,5r)-2,5-dihydroxy-6-[(1r,2r,3r,5s,6r,7s,10r)-5-hydroxy-6,10-dimethyltricyclo[5.3.0.0²,⁶]decan-3-yl]-2-methylhepta-3,6-dien-1-yl acetate

C22H34O5 (378.2406)

(2e,6e,13e)-1-(2,5-dihydroxy-3-methylphenyl)-15-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,13-triene-5,12-dione

C27H38O5 (442.2719)

(5r)-5-hydroxy-4-[(3e,7e)-4,8,12-trimethyl-10-oxotrideca-3,7,11-trien-1-yl]-5h-furan-2-one

C20H28O4 (332.1987)

1-(6-hydroxy-2,8-dimethylchromen-2-yl)-4,8,12-trimethyltrideca-3,7,11-triene-5,6-diol

C27H38O4 (426.277)

2-[(2-hydroxy-2,5,5,8a-tetramethyl-hexahydro-1h-naphthalen-1-yl)methyl]benzene-1,4-diol

C21H32O3 (332.2351)

6'-(2,4,6-trihydroxyphenoxy)-[1,1'-biphenyl]-2,2',4,4',6-pentol

C18H14O9 (374.0638)

[5-(acetyloxy)-2-(2-methyl-5-oxocyclopent-3-en-1-yl)-3-(6-methylhepta-2,5-dien-2-yl)cyclopentyl]methyl acetate

C24H34O5 (402.2406)

[(1z,5e,8r,11s)-6-methyl-11-[(2s)-6-methylhept-5-en-2-yl]-10-oxo-9-oxabicyclo[6.2.1]undeca-1,5-dien-2-yl]methyl acetate

C22H32O4 (360.23)

(9ar,11ar)-1-[(2r)-5-hydroperoxy-5-isopropylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-dione

C29H44O4 (456.3239)

2-[(2e,6e,10e)-15-hydroxy-3,7,11,15-tetramethyl-14-oxohexadeca-2,6,10-trien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

C27H38O4 (426.277)

5-(1,2-dihydroxyethyl)-2,6,10,12-tetrahydroxy-4,7-dioxatricyclo[6.4.0.0²,⁶]dodeca-1(12),8,10-trien-3-one

C12H12O9 (300.0481)

4,4,12b-trimethyl-1,2,3,4a,5,6-hexahydrotetraphene-8,11-dione

C21H24O2 (308.1776)

3-(3-{[1,1'-biphenyl]-2,2',4,4',6,6'-hexyloxy}-2-[4-(3-{4-[2,6-bis({[1,1'-biphenyl]-2,2',4,4',6,6'-hexyloxy})-4-hydroxyphenoxy]-2,6-dihydroxyphenoxy}-2-(3,5-dihydroxyphenoxy)-5-hydroxyphenoxy)-3,5-dihydroxyphenoxy]-5-hydroxyphenoxy)-[1,1'-biphenyl]-2,2',4,4',6,6'-hexol

C84H58O42 (1738.2403)

3-methyl-5-(6-methylhept-5-en-2-yl)-8-methylidene-3a,4,5,6,7,8a-hexahydro-1h-azulen-4-ol

C20H32O (288.2453)

(2r,3r)-2-(dec-9-en-1-yl)-3-pentyloxirane

C17H32O (252.2453)

ethyl (10z,13z)-hexadeca-10,13-dienoate

C18H32O2 (280.2402)

2-(4-{4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-furan]-3-yl}-3-methylbut-2-en-1-yl)-6-methylcyclohexa-2,5-diene-1,4-dione

C27H34O4 (422.2457)

10,12-dihydroxy-5-methyl-8-(6-methylhept-5-en-2-yl)-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-7-yl acetate

C22H34O5 (378.2406)

3,4-dibromo-5-(3-hydroxy-2-methylpropyl)benzene-1,2-diol

C10H12Br2O3 (337.9153)

(6e,10e)-12-(5-hydroxy-2-methoxy-3-methylphenyl)-6,10-dimethyldodeca-6,10-diene-2,8-dione

C22H30O4 (358.2144)

1-(2,5-dihydroxy-3-methylphenyl)-13-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-5-one

C27H38O4 (426.277)

methyl (8e,11e,14e)-icosa-8,11,14-trienoate

C21H36O2 (320.2715)

6-(4-hydroxy-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydro-1h-azulen-5-yl)-2-methylheptan-3-one

C20H32O2 (304.2402)

(2s,6s,7s,8s)-1,3-dimethyl-8-[(2s)-6-methylhept-5-en-2-yl]tricyclo[4.4.0.0²,⁷]dec-3-ene

C20H32 (272.2504)

(1s,10s,10as)-7-methyl-10-[(2r)-6-methylhept-5-en-2-yl]-3-oxo-1h,5h,8h,9h,10h,10ah-cyclonona[c]furan-1-yl acetate

C22H32O4 (360.23)

3-(14,15-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10-trien-1-yl)-4-hydroxy-5-methylphenyl octadecanoate

C45H76O5 (696.5692)

methyl 2-(5-hydroxy-2-{[(6e)-3-methyl-7-{[(1r,5r)-3-methyl-5-(2-methylprop-1-en-1-yl)-4-oxocyclopent-2-en-1-yl]methyl}octa-1,6-dien-3-yl]oxy}phenyl)acetate

C29H38O5 (466.2719)

(3as,4r,5s,8ar)-5-[(2r,5r)-5-hydroxy-6-methylhept-6-en-2-yl]-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydro-1h-azulen-4-ol

C20H32O2 (304.2402)

1,1,5,10-tetraoxo-2h,3h,4h,6h,7h-1λ⁶-[1,4]thiazino[2,3-g]quinoline-7-carboxylic acid

C12H10N2O6S (310.026)

(4r,6r,7z,10e)-4-hydroxy-13-[(2r)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-7,10-dien-5-one

C27H40O4 (428.2926)

(2s,4ar,4br,6ar,12as,12br,14ar)-1,1,4a,6a,8,12b-hexamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-2,10-diol

C27H40O3 (412.2977)

(4r)-4-hydroxy-13-[(2r)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-2,10-dien-5-one

C27H40O4 (428.2926)

2-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}cyclohexa-2,5-diene-1,4-dione

C21H28O2 (312.2089)

6-(2,5-dimethoxy-3-methylphenyl)-1-[2-(4-hydroxy-4-methylpentanoyl)-1,2-dimethylcyclopentyl]-4-methylhex-4-en-2-one

C29H44O5 (472.3189)

(4r,6s,7z,10e)-4-hydroxy-13-[(2r)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6,10-trimethyltrideca-7,10-dien-5-one

C27H40O4 (428.2926)

3-(3-{[1,1'-biphenyl]-2,2',4,4',6,6'-hexyloxy}-2-(3,5-dihydroxyphenoxy)-5-hydroxyphenoxy)-[1,1'-biphenyl]-2,2',4,4',6,6'-hexol

C36H26O18 (746.1119)

(2r)-2,8-dimethyl-2-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]chromen-6-yl acetate

C29H40O3 (436.2977)

(7z)-5-methoxy-8-methyl-11-(6-methylhept-5-en-2-yl)-13-oxa-2-azatricyclo[8.2.1.0⁴,¹²]trideca-2,4(12),7-trien-3-ol

C21H31NO3 (345.2304)

(1r,2s,5r,6s,7s,8r)-2,8-dimethyl-5-[(2z)-6-methylhepta-2,5-dien-2-yl]tricyclo[5.3.0.0²,⁶]decan-1-ol

C20H32O (288.2453)

(2e,6e,10e,12s)-12-hydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraenoic acid

C20H32O3 (320.2351)

3a,5,8a-trimethyl-1-(prop-1-en-2-yl)-decahydro-1h-cyclohexa[f]azulene-5,8-diol

C20H34O2 (306.2559)

2-[(2e)-4-[(1s,4'r,4as,7as)-4'-methoxy-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-3-yl]-3-methylbut-2-en-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

C28H38O5 (454.2719)

(3s,4s,5s)-4,5-dihydroxy-3-[(3e,7e)-4,8,12-trimethyl-10-oxotrideca-3,7,11-trien-1-yl]oxolan-2-one

C20H30O5 (350.2093)

(4s,6r,9r,10r,11r)-11,13-dimethoxy-6-methyl-9-[(2s)-6-methylhept-5-en-2-yl]-5,12-dioxatricyclo[8.3.0.0⁴,⁶]tridec-1-ene

C22H36O4 (364.2613)

(7r,8s)-10,12-dihydroxy-5-methyl-8-(6-methylhept-5-en-2-yl)-11-oxatricyclo[7.3.0.0²,⁴]dodec-1(9)-en-7-yl acetate

C22H34O5 (378.2406)

(6e,10e,14e)-16-(2,5-dihydroxy-3-methylphenyl)-1,12-dihydroxy-2,6,10,14-tetramethylhexadeca-2,6,10,14-tetraen-4-one

C27H38O5 (442.2719)

(3as,4ar,8s,8as)-4a-hydroxy-1-isopropyl-3a,8a-dimethyl-5-methylidene-3h,4h,6h,7h,8h,9h-cyclohexa[f]azulen-8-yl acetate

C22H32O3 (344.2351)

5-(acetyloxy)-2',4'b,7,8',8',10'a-hexamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-7'-yl acetate

C31H44O5 (496.3189)

3-[2-(4-{[5-(3,5-dihydroxyphenoxy)-[1,1'-biphenyl]-2',4,4',6,6'-pentyl]oxy}-3,5-dihydroxyphenoxy)-5-hydroxy-3-{[6-(2,4,6-trihydroxyphenoxy)-[1,1'-biphenyl]-2,2',4,4',6'-pentyl]oxy}phenoxy]-[1,1'-biphenyl]-2,2',4,4',6,6'-hexol

C60H42O30 (1242.1761)

(1s,3ar,4r,7ar)-7,7a-diformyl-3a-methyl-1-[(2s)-6-methylhept-5-en-2-yl]-2,3,4,5-tetrahydro-1h-inden-4-yl acetate

C22H32O4 (360.23)

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-[(1s,6r,7r)-2,4-dihydroxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl]-4-methylhex-4-en-2-one

C27H36O5 (440.2563)

(1r,2e,5e,9r)-6-methyl-9-[(2s)-6-methylhept-5-en-2-yl]cyclonona-2,5-diene-1,2-dicarbaldehyde

C20H30O2 (302.2246)

(2s,4as,4bs,6as,11as,11bs,13ar)-2-hydroxy-1,1,4a,6a,9,11b-hexamethyl-2h,3h,4h,4bh,5h,6h,11h,11ah,12h,13h,13ah-indeno[2,1-a]phenanthrene-7,10-dione

C27H38O3 (410.2821)

(3r,3as,7as)-7a-methyl-3-[(2s)-6-methylhept-5-en-2-yl]-2,3,6,7-tetrahydro-1h-indene-3a,4-dicarbaldehyde

C20H30O2 (302.2246)

(6e,11r,14e)-11,16-dihydroxy-2,6,14-trimethyl-10-methylidenehexadeca-6,14-dien-4-one

C20H34O3 (322.2508)

nonadeca-9,18-diene-6,7-diol

C19H36O2 (296.2715)

4,10-dimethyl-7-(6-methylhepta-2,5-dien-2-yl)tricyclo[4.4.0.0¹,⁵]decan-10-ol

C20H32O (288.2453)

(3ar,4s,5r,8as)-5-[(2s,5r)-6-chloro-5-hydroxy-6-methylheptan-2-yl]-3-methyl-8-methylidene-3a,4,5,6,7,8a-hexahydro-1h-azulen-4-ol

C20H33ClO2 (340.2169)

(2e)-5-(6-methoxy-2,8-dimethylchromen-2-yl)-2-methylpent-2-enal

C18H22O3 (286.1569)

3,5-bis(acetyloxy)-2-[3,5-bis(acetyloxy)-4-[3,5-bis(acetyloxy)-2-[3,5-bis(acetyloxy)-4-[3,4,5-tris(acetyloxy)phenoxy]phenoxy]phenoxy]phenoxy]phenyl acetate

C54H46O28 (1142.2176)

(2s,4ar,4br,6as,12as,12br,14ar)-1,1,4a,6a,8,12b-hexamethyl-2h,3h,4h,4bh,5h,6h,12h,12ah,13h,14h,14ah-naphtho[2,1-a]xanthene-2,10-diol

C27H40O3 (412.2977)

(7s,9ar,11ar)-1-[(2r,5e)-7-hydroperoxy-5-isopropylhept-5-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H48O3 (444.3603)

4,5-bis(acetyloxy)-2',4'b,7,8',8',10'a-hexamethyl-2',3',4',4'a,5',6',7',8'a,9',10'-decahydro-3h-spiro[1-benzofuran-2,1'-phenanthren]-7'-yl acetate

C33H46O7 (554.3243)

6,10,12a-trimethyl-3-(prop-1-en-2-yl)-1h,2h,3h,3ah,4h,5h,8h,9h,12h-cyclopenta[11]annulen-1-yl acetate

C22H34O2 (330.2559)

6-methyl-11-(6-methylhept-5-en-2-yl)-9-oxabicyclo[6.2.1]undec-5-ene-2,10-dione

C19H28O3 (304.2038)

(7s,10r)-10-hydroxy-12-{[(2s)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]methyl}-6,6,9,9-tetramethyl-8-oxabicyclo[5.4.1]dodec-1(12)-en-2-one

C27H38O5 (442.2719)