NCBI Taxonomy: 3009

Fucales (ncbi_taxid: 3009)

found 500 associated metabolites at order taxonomy rank level.

Ancestor: Phaeophyceae

Child Taxonomies: Fucaceae, Sargassaceae, Notheiaceae, Hormosiraceae, Durvillaeaceae, Seirococcaceae, Himanthaliaceae, unclassified Fucales, environmental samples

Fucoxanthin

(3S,3′S,5R,5′R,6S,6′R)-3′-(Acetyloxy)-6′,7′-didehydro-5,6-epoxy-5,5′,6,6′,7,8-hexahydro-3,5′-dihydroxy-8-oxo-β,β-carotene

C42H58O6 (658.4233168)


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

(2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-3,4-Dihydroxy-2,(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C12H22O11 (342.1162062)


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).

   

DL-Mannitol

(2R,3R,4R,5R)-hexane-1,2,3,4,5,6-hexol

C6H14O6 (182.0790344)


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

4-[2-(dimethylamino)ethyl]phenol

C10H15NO (165.115358)


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).

   

Campesterol

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,5R)-5,6-dimethylheptan-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C28H48O (400.37049579999996)


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

   

Stigmasterol

(3S,8S,9S,10R,13R,14S,17R)-17-((2R,5S,E)-5-ethyl-6-methylhept-3-en-2-yl)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H48O (412.37049579999996)


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

   

beta-Carotene

1,3,3-trimethyl-2-[(1E,3E,5E,7E,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 (536.4381776)


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-Cryptoxanthin

(1R)-3,5,5-trimethyl-4-[(1E,3E,5E,7E,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-3-en-1-ol

C40H56O (552.4330926)


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

(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-en-1-ol

C40H56O2 (568.4280076)


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

   

Phytol

2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (theta-(theta,theta-(E)))-

C20H40O (296.307899)


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].

   

Dihomo-gamma-linolenic acid

(8Z,11Z,14Z)-Icosa-8,11,14-trienoic acid

C20H34O2 (306.2558664)


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).

   

Glucose

(3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

C6H12O6 (180.0633852)


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.

   

L-Alanine

(2S)-2-aminopropanoic acid

C3H7NO2 (89.0476762)


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.

   

delta-Tocotrienol

(2R)-2,8-Dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol

C27H40O2 (396.302814)


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

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C27H46O (386.3548466)


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

   

Neoxanthin

(1R,3S)-6-[(1M,3E,5E,7E,9E,11E,13E,15Z,17E)-18-[(1S,4S,6R)-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 (600.4178376)


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

(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-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-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

C40H56O4 (600.4178376)


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

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C28H46O (398.3548466)


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

   

Fucosterol

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H48O (412.37049579999996)


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

   

Deoxylapachol

2-Deoxylapachol;1,4-Naphthalenedione, 2-(3-methyl-2-butenyl)-

C15H14O2 (226.09937440000002)


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].

   

Grevillol

5-tridecylbenzene-1,3-diol

C19H32O2 (292.24021719999996)


   

Hexachlorobutadiene

HEXACHLORO-1,3-BUTADIENE

C4Cl6 (257.81311800000003)


D016573 - Agrochemicals D010575 - Pesticides

   

24-Methylenecholesterol

(3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(2R)-6-methyl-5-methylideneheptan-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C28H46O (398.3548466)


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

   

Glucose

(2S,3R,4S,5R,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol

C6H12O6 (180.0633852)


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).

   

Sorbitol

(2R,3R,4R,5S)-Hexane-1,2,3,4,5,6-hexol

C6H14O6 (182.0790344)


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

D-alpha-Aminopropionic acid

C3H7NO2 (89.0476762)


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.

   

DL-2-Aminopropionic acid

2-aminopropanoic acid

C3H7NO2 (89.0476762)


(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].

   

2-Hydroxy-6-tridecylbenzoic acid

Ginkgolic acid (13:0);Ginkgoneolic Acid;6-Tridecylsalicylic acid

C20H32O3 (320.23513219999995)


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:

   

Dihydroactinidiolide

(+/-)-(2,6,6,-TRIMETHYL-2-HYDROXYCYCLOHEXYLIDENE)ACETIC ACID .GAMMA.-LACTONE [FHFI]

C11H16O2 (180.1150236)


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

2,4-Pentadienoic acid, 5-(1-hydroxy-2,6,6-trimethyl-4-oxo-2-cyclohexen-1-yl)-3-methyl-, (Z,E)-(S)-(+)-

C15H20O4 (264.13615200000004)


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].

   

Geranylacetone

trans-6,10-Dimethyl-5,9-undecadien-2-one

C13H22O (194.1670562)


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

   

2-Pentadecanone

Methyl tridecyl ketone

C15H30O (226.22965299999998)


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

(3E,5Z)-undeca-1,3,5-triene

C11H18 (150.1408428)


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

Methyl pentadecyl ketone

C17H34O (254.26095139999998)


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

   

1-Pentadecene

Pentadec-1-ene

C15H30 (210.234738)


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.

   

(-)-alpha-Tocopherol

2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-ol

C29H50O2 (430.38106)


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

2,8-dimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-2H-1-benzopyran-6-ol

C27H40O2 (396.302814)


   

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

2,7,8-trimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-2H-1-benzopyran-6-ol

C28H42O2 (410.3184632)


   

1-Iodopentane

1-Iodopentane

C5H11I (197.9905476)


   

(E,E,E)-Geranylgeranyl alcohol

3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-ol

C20H34O (290.2609514)


   

D-Iditol

hexane-1,2,3,4,5,6-hexol

C6H14O6 (182.0790344)


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

   

Loliolide

(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

C11H16O3 (196.1099386)


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

   

Latoxanthin

(1R,2R,4S)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-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-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol

C40H58O5 (618.4284018)


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.

   

Sargachromanol C

Sargachromanol C

C27H40O3 (412.297729)


   
   
   
   

sitosterol

17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol

C29H50O (414.386145)


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

   

Betaine

2-(trimethylazaniumyl)acetate

C5H11NO2 (117.0789746)


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

Stigmasterol

C29H48O (412.37049579999996)


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

   

Glucose

alpha-D-Glucose

C6H12O6 (180.0633852)


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

methyl icosa-8,11,14-trienoate

C21H36O2 (320.2715156)


   

Fucosterol

(24E)-24-n-propylidenecholesterol;(3beta,24E)-stigmasta-5,24(28)-dien-3-ol;(E)-stigmasta-5,24(28)-dien-3beta-ol;24E-ethylidene-cholest-5-en-3beta-ol;fucosterin;trans-24-ethylidenecholesterol

C29H48O (412.37049579999996)


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

   

Neoxanthin

(1R,3S)-6-[(3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenylidene]-1,5,5-trimethyl-cyclohexane-1,3-diol

C40H56O4 (600.4178376)


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

Yezoquinolide

C27H34O4 (422.24569640000004)


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

   

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

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

C18H30O2 (278.224568)


   
   

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

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

C19H32O3 (308.23513219999995)


   

HEPTADEC-3-EN-2-ONE

HEPTADEC-3-EN-2-ONE

C17H32O (252.2453022)


   
   

Cholesterol

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C27H46O (386.3548466)


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

   

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

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

C18H32O2 (280.2402172)


   

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

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

C17H28O3 (280.2038338)


   
   

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

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

C18H30O2 (278.224568)


   

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

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

C14H18O4 (250.1205028)


   
   
   

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

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

C18H30O2 (278.224568)


   

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

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

C18H30O2 (278.224568)


   

Sorbitol

(2R,3R,4R,5S)-Hexane-1,2,3,4,5,6-hexol

C6H14O6 (182.0790344)


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

ergosta-5,22E-dien-3beta-ol

C28H46O (398.3548466)


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

   

Campesterol

Campesterol

C28H48O (400.37049579999996)


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

   

Abscisic Acid

(+)-Abscisic acid

C15H20O4 (264.13615200000004)


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

L-3-(3,4-dihydroxyphenyl)-Alanine

C9H11NO4 (197.0688046)


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

1-(1,2,3,4,5-Pentahydroxypent-1-yl)-1,2,3,4-tetrahydro-beta-carboline-3-carboxylate

C40H56 (536.4381776)


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

L-alanine

C3H7NO2 (89.0476762)


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.

   

D-Alanine

D-Alanine

C3H7NO2 (89.0476762)


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.

   

Sucrose

Sucrose

C12H22O11 (342.11620619999997)


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

2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (theta-(theta,theta-(E)))-

C20H40O (296.307899)


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

gamma-Tocotrienol

C28H42O2 (410.3184632)


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].

   

Violaxanthin

(1S,4S,6R)-1-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1S,4S,6R)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-4-ol

C40H56O4 (600.4178376)


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

(all-E)-beta-Cryptoxanthin

C40H56O (552.4330926)


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

(1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(4R)-4-hydroxy-2,6,6-trimethyl-1-cyclohexenyl]-3,7,12,16-tetramethyl-octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethyl-cyclohex-3-en-1-ol

C40H56O2 (568.4280076)


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.

   

Hordenine

N,N-Dimethyl-2-(4-hydroxyphenyl)ethylamine

C10H15NO (165.115358)


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

L-α-Aminopropionic acid

C3H7NO2 (89.0476762)


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.

   

loliolide

2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S-cis)-

C11H16O3 (196.1099386)


A natural product found in Brachystemma calycinum.

   

dihomo-gamma-linolenic acid

cis-8,11,14-Eicosatrienoic Acid

C20H34O2 (306.2558664)


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

   

Fucoxanthin

InChI=1/C42H58O6/c1-29(18-14-19-31(3)22-23-37-38(6,7)26-35(47-33(5)43)27-40(37,10)46)16-12-13-17-30(2)20-15-21-32(4)36(45)28-42-39(8,9)24-34(44)25-41(42,11)48-42/h12-22,34-35,44,46H,24-28H2,1-11H3/b13-12+,18-14+,20-15+,29-16+,30-17+,31-19+,32-21+/t23?,34-

C42H58O6 (658.4233168000001)


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

phloroglucinol

C6H6O3 (126.0316926)


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.

   

Geranylacetone

6,10-Dimethyl-5,9-undecadien-2-one

C13H22O (194.1670562)


   

24-oxocholesterol

24-oxo-cholest-5-en-3beta-ol

C27H44O2 (400.3341124)


   

Dormin

(2E,4E)-5-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)-3-methylpenta-2,4-dienoic acid

C15H20O4 (264.13615200000004)


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].

   

2-Pentadecanone

Methyl tridecyl ketone

C15H30O (226.22965299999998)


   

Dihydroactinidiolide

2-Hydroxy-2,6,6-trimethylcyclohexylidene-1-acetic acid lactone

C11H16O2 (180.1150236)


(±)-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].

   

1-PENTADECENE

1-PENTADECENE

C15H30 (210.234738)


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

   
   
   

Saringosterol

24-vinyl-cholest-5-ene-3beta,24-diol

C29H48O2 (428.36541079999995)


   

2-aminoethanesulfonic acid

2-aminoethanesulfonic acid

C2H7NO3S (125.0146632)


   

D-Sorbitol

(2R,3R,4R,5S)-hexane-1,2,3,4,5,6-hexol

C6H14O6 (182.0790344)


   

D-(1-(13)C)glucitol

(2R,3R,4S,5R)-hexane-1,2,3,4,5,6-hexol

C6H14O6 (182.0790344)


   

(2R)-2-aminopropanoic acid

(2R)-2-aminopropanoic acid

C3H7NO2 (89.0476762)


   

D(+)-Glucose

(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

C6H12O6 (180.0633852)


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

   
   

L-Guluronic acid

L-Guluronic acid

C6H10O7 (194.042651)


   
   

n-trimethyllysine

n-trimethyllysine

C9H21N2O2+ (189.16029460000001)


D050258 - Mitosis Modulators > D008934 - Mitogens

   

tetrachloroethane

1,1,1,2-TETRACHLOROETHANE

C2H2Cl4 (165.89106120000002)


   

maltodextrin

(2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

C6H12O6 (180.0633852)


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

   

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

2,7,8-trimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-3,4-dihydro-2H-1-benzopyran-6-ol

C28H42O2 (410.3184632)


   

Plastoquinone

Plastoquinone-9

C53H80O2 (748.615798)


   

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

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

C28H40O5 (456.28755900000004)


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

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

C28H40O5 (456.28755900000004)


   

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

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

C28H40O5 (456.28755900000004)


   

Plastoquinone 1

Plastoquinone 1

C27H42O4 (430.30829320000004)


A natural product found in Sargassum micracanthum.

   

Plastoquinone 2

Plastoquinone 2

C27H40O4 (428.29264400000005)


A natural product found in Sargassum micracanthum.

   
   
   
   

Hexachlorobutadiene

HEXACHLORO-1,3-BUTADIENE

C4Cl6 (257.81311800000003)


D016573 - Agrochemicals D010575 - Pesticides

   

Dihydrocholesterol

Dihydrocholesterol

C27H48O (388.37049579999996)


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

   

galbanum decatriene

(3E,5Z)-undeca-1,3,5-triene

C11H18 (150.1408428)


   

(S)-Sargachromenol

(S)-Sargachromenol

C27H36O4 (424.2613456)


A natural product found in Botryllus tuberatus.

   

(R)-Sargachromenol

(R)-Sargachromenol

C27H36O4 (424.2613456)


A natural product found in Botryllus tuberatus.

   

Avenasterol

24Z-ethylidene-cholest-7-en-3beta-ol

C29H48O (412.37049579999996)


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

   

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

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

C21H34 (286.2660364)


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

   

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

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 (456.28755900000004)


   

(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

(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 (423.25400680000007)


   

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

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 (1200.2230308)


   

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

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

C18H30O2 (278.224568)


   

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

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 (412.297729)


   

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

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

C28H42O5 (458.30320820000003)


   

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

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

C45H74O5 (694.5535954)


   

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

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 (426.2769948)


   

(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

(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 (446.30320820000003)


   

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

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

C20H34O3 (322.25078140000005)


   

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

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

C20H30O3 (318.21948299999997)


   

(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

(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 (344.13185539999995)


   

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

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 (334.214398)


   

2,4,5-trihydroxy-3-methoxyhexanal

2,4,5-trihydroxy-3-methoxyhexanal

C7H14O5 (178.08411940000002)


   

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

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

C27H44O2 (400.3341124)


   

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

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

C20H32O2 (304.24021719999996)


   

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

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

C27H34O6 (454.2355264)


   

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

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

C20H32O2 (304.24021719999996)


   

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

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

C27H36O4 (424.2613456)


   

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

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 (428.3290274)


   

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

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

C18H30O2 (278.224568)


   

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

(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 (456.28755900000004)


   

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

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 (1586.1776599999998)


   

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

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

C20H34O3 (322.25078140000005)


   

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

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

C28H42O5 (458.30320820000003)


   
   

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

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 (1466.2656818)


   

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

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 (486.2981232)


   

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

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

C14H14O8 (310.0688644)


   

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

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 (442.2719098)


   
   

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

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

C21H34O3 (334.25078140000005)


   

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

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

C18H32O3 (296.2351322)


   

(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

(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 (440.2562606)


   

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

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

C27H38O3 (410.2820798)


   

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

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

C27H38O4 (426.2769948)


   

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

(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 (410.3184632)


   

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

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

C24H18O12 (498.0798228)


   

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

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 (438.2769948)


   

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

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 (870.1279529999999)


   

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

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

C28H40O4 (440.29264400000005)


   

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

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

C11H12O4 (208.0735552)


   

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

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 (428.29264400000005)


   

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

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 (426.2769948)


   

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

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 (410.2820798)


   

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

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

C20H30O4 (334.214398)


   

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

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 (1134.0069962000002)


   

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

(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 (350.209313)


   

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

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

C20H34O3 (322.25078140000005)


   

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

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 (600.4178376)


   

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

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

C15H20N2O3S2 (340.091529)


   
   

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

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

C15H20O4 (264.13615200000004)


   

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

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 (454.2719098)


   

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

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

C25H34O4 (398.24569640000004)


   

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

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

C27H38O3 (410.2820798)


   

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

(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 (472.3188574)


   

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

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 (426.34976159999997)


   

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

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

C27H38O2 (394.28716479999997)


   

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

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 (426.2769948)


   

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

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 (440.2562606)


   

(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

(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 (472.3188574)


   

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

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

C27H38O5 (442.2719098)


   

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

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

C20H28O4 (332.19874880000003)


   

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

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

C27H38O4 (426.2769948)


   

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

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

C18H14O9 (374.06377940000004)


   

(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

(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 (456.3239424)


   

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

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 (426.2769948)


   

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

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 (300.0481302)


   

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

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 (1738.2402567999998)


   

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

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

C17H32O (252.2453022)


   

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

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

C18H32O2 (280.2402172)


   

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

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 (422.24569640000004)


   

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

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

C22H30O4 (358.214398)


   

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

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

C27H38O4 (426.2769948)


   

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

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

C21H36O2 (320.2715156)


   

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

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

C45H76O5 (696.5692445999999)


   

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

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 (466.2719098)


   

(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

(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 (428.29264400000005)


   

(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

(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 (428.29264400000005)


   

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

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

C29H44O5 (472.3188574)


   

(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

(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 (428.29264400000005)


   

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

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 (746.1119096)


   

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

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

C20H32O3 (320.23513219999995)


   

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

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 (454.2719098)


   

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

(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 (350.209313)


   

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

(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 (442.2719098)


   

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

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 (1242.1760832)


   

(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

(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 (440.2562606)


   

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

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

C20H34O3 (322.25078140000005)


   

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

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

C19H36O2 (296.2715156)


   

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

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

C18H22O3 (286.15688620000003)


   

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

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 (1142.2175516)


   

(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

(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 (444.36032579999994)


   

(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

(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 (442.2719098)


   

(2e,6e,10e,13e)-3,7,11,15-tetramethylhexadeca-2,6,10,13-tetraene-1,15-diol

(2e,6e,10e,13e)-3,7,11,15-tetramethylhexadeca-2,6,10,13-tetraene-1,15-diol

C20H34O2 (306.2558664)


   

(2r,3r,4r,5r)-6-{[(2r,3r,4s,5s)-5-[(dimethylarsoryl)methyl]-3,4-dihydroxyoxolan-2-yl]oxy}hexane-1,2,3,4,5-pentol

(2r,3r,4r,5r)-6-{[(2r,3r,4s,5s)-5-[(dimethylarsoryl)methyl]-3,4-dihydroxyoxolan-2-yl]oxy}hexane-1,2,3,4,5-pentol

C13H27AsO10 (418.0820102)


   

5-[(5z,8z,11z,14z)-heptadeca-5,8,11,14-tetraen-1-yl]benzene-1,3-diol

5-[(5z,8z,11z,14z)-heptadeca-5,8,11,14-tetraen-1-yl]benzene-1,3-diol

C23H32O2 (340.24021719999996)


   

(2z,6e,10e)-12-(2,5-dihydroxy-3-methylphenyl)-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

(2z,6e,10e)-12-(2,5-dihydroxy-3-methylphenyl)-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

C27H38O4 (426.2769948)


   

(5e,9e,13r)-13,14-dihydroxy-6,10,14-trimethylpentadeca-5,9-dien-2-one

(5e,9e,13r)-13,14-dihydroxy-6,10,14-trimethylpentadeca-5,9-dien-2-one

C18H32O3 (296.2351322)


   

13-(furan-3-yl)-2,6,10-trimethyltrideca-2,6,10-trien-4-ol

13-(furan-3-yl)-2,6,10-trimethyltrideca-2,6,10-trien-4-ol

C20H30O2 (302.224568)


   

(2e,6e,10e)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraenal

(2e,6e,10e)-3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraenal

C20H30O2 (302.224568)


   

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

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

C48H34O28 (1058.1236564)


   

3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraenoic acid

3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraenoic acid

C20H30O3 (318.21948299999997)


   

(4s,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

(4s,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 (446.30320820000003)


   

methyl 2-(5-hydroxy-2-{[(6e,10e,13s)-13-hydroxy-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,10,14-tetraen-3-yl]oxy}phenyl)acetate

methyl 2-(5-hydroxy-2-{[(6e,10e,13s)-13-hydroxy-3,7,11,15-tetramethyl-12-oxohexadeca-1,6,10,14-tetraen-3-yl]oxy}phenyl)acetate

C29H40O6 (484.28247400000004)


   

(5e,10e,14r)-14-hydroxy-2,6,10-trimethylpentadeca-2,5,10-trien-4-one

(5e,10e,14r)-14-hydroxy-2,6,10-trimethylpentadeca-2,5,10-trien-4-one

C18H30O2 (278.224568)


   

3-(acetyloxy)-5-[4-(acetyloxy)-2-{[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy}-6-{[2,2',4,4',6'-pentakis(acetyloxy)-6-[2,4,6-tris(acetyloxy)phenoxy]-[1,1'-biphenyl]-3-yl]oxy}phenoxy]phenyl acetate

3-(acetyloxy)-5-[4-(acetyloxy)-2-{[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy}-6-{[2,2',4,4',6'-pentakis(acetyloxy)-6-[2,4,6-tris(acetyloxy)phenoxy]-[1,1'-biphenyl]-3-yl]oxy}phenoxy]phenyl acetate

C76H64O38 (1584.3075444)


   

2-[(2e,6e)-10-[(3z,6r)-6-(2-hydroxypropan-2-yl)-2-oxooxan-3-ylidene]-3,7-dimethyldeca-2,6-dien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

2-[(2e,6e)-10-[(3z,6r)-6-(2-hydroxypropan-2-yl)-2-oxooxan-3-ylidene]-3,7-dimethyldeca-2,6-dien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

C27H36O5 (440.2562606)


   

(5e,10r)-6,10,14-trimethylpentadec-5-ene-2,12-dione

(5e,10r)-6,10,14-trimethylpentadec-5-ene-2,12-dione

C18H32O2 (280.2402172)


   

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

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

C42H30O24 (918.112698)


   

(6e,10e,14s)-14-hydroxy-2,6,10-trimethylpentadeca-6,10-dien-4-one

(6e,10e,14s)-14-hydroxy-2,6,10-trimethylpentadeca-6,10-dien-4-one

C18H32O2 (280.2402172)


   

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

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

C25H34O4 (398.24569640000004)


   

(2r)-1-[(1s,4's,5s,6r,7s)-4'-hydroxy-1,5,5',5'-tetramethylspiro[bicyclo[3.2.0]heptane-6,2'-oxolan]-7-yl]-2-[(2-hydroxy-5-methoxy-3-methylphenyl)methyl]-3-methylbut-3-en-1-one

(2r)-1-[(1s,4's,5s,6r,7s)-4'-hydroxy-1,5,5',5'-tetramethylspiro[bicyclo[3.2.0]heptane-6,2'-oxolan]-7-yl]-2-[(2-hydroxy-5-methoxy-3-methylphenyl)methyl]-3-methylbut-3-en-1-one

C28H40O5 (456.28755900000004)


   

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

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

C42H30O23 (902.117783)


   

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

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

C27H40O4 (428.29264400000005)


   

3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene-1,13-diol

3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene-1,13-diol

C20H34O2 (306.2558664)


   

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

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

C29H46O (410.3548466)


   

(4e)-1-[(1r,2r)-2-[(2e)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl]-6-(2-hydroxy-5-methoxy-3-methylphenyl)-4-methylhex-4-en-2-one

(4e)-1-[(1r,2r)-2-[(2e)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl]-6-(2-hydroxy-5-methoxy-3-methylphenyl)-4-methylhex-4-en-2-one

C28H40O5 (456.28755900000004)


   

2-iodobenzene-1,3,5-triol

2-iodobenzene-1,3,5-triol

C6H5IO3 (251.928345)


   

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

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

C27H38O4 (426.2769948)


   

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

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

C24H18O14 (530.0696528)


   

(2z,6e)-2-[(3r)-3-chloro-4-methylpent-4-en-1-yl]-9-[(2r)-6-hydroxy-2,8-dimethylchromen-2-yl]-6-methylnona-2,6-dienoic acid

(2z,6e)-2-[(3r)-3-chloro-4-methylpent-4-en-1-yl]-9-[(2r)-6-hydroxy-2,8-dimethylchromen-2-yl]-6-methylnona-2,6-dienoic acid

C27H35ClO4 (458.22237400000006)


   

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

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

C24H18O12 (498.0798228)


   

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

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

C27H38O4 (426.2769948)


   

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

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

C28H40O5 (456.28755900000004)


   

5-[2-(3,5-dihydroxyphenoxy)-3,5-dihydroxyphenoxy]benzene-1,2,3-triol

5-[2-(3,5-dihydroxyphenoxy)-3,5-dihydroxyphenoxy]benzene-1,2,3-triol

C18H14O9 (374.06377940000004)


   

(2e,6e,10e,12e)-3,7,11,15-tetramethylhexadeca-2,6,10,12,14-pentaen-1-ol

(2e,6e,10e,12e)-3,7,11,15-tetramethylhexadeca-2,6,10,12,14-pentaen-1-ol

C20H32O (288.24530219999997)


   

2-(10-hydroxy-9-methoxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

2-(10-hydroxy-9-methoxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

C28H42O4 (442.30829320000004)


   

(2r,2's,4s,6s,7s,10s,12s)-2',12,17-trihydroxy-6-methyl-3,8-dioxaspiro[hexacyclo[11.8.0.0²,⁴.0²,¹⁰.0⁶,¹⁰.0¹⁴,¹⁹]henicosane-7,3'-oxolane]-1(13),14,16,18-tetraene-5',20-dione

(2r,2's,4s,6s,7s,10s,12s)-2',12,17-trihydroxy-6-methyl-3,8-dioxaspiro[hexacyclo[11.8.0.0²,⁴.0²,¹⁰.0⁶,¹⁰.0¹⁴,¹⁹]henicosane-7,3'-oxolane]-1(13),14,16,18-tetraene-5',20-dione

C23H22O8 (426.1314612)


   

2-(10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl)-6-methylcyclohexa-2,5-diene-1,4-dione

2-(10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl)-6-methylcyclohexa-2,5-diene-1,4-dione

C27H40O4 (428.29264400000005)


   

cholest-4-ene-3,6-dione

cholest-4-ene-3,6-dione

C27H42O2 (398.3184632)


   

3-({5-[(dimethylarsoryl)methyl]-3,4-dihydroxyoxolan-2-yl}oxy)-2-hydroxypropane-1-sulfonic acid

3-({5-[(dimethylarsoryl)methyl]-3,4-dihydroxyoxolan-2-yl}oxy)-2-hydroxypropane-1-sulfonic acid

C10H21AsO9S (392.01221960000004)


   

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

(7s,9ar,11ar)-1-[(2r,5r)-5-hydroperoxy-5-isopropylhept-6-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 (444.36032579999994)


   

2-[(2e,6e)-3,7-dimethyl-10-[(3z,6r)-2-oxo-6-(prop-1-en-2-yl)oxan-3-ylidene]deca-2,6-dien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

2-[(2e,6e)-3,7-dimethyl-10-[(3z,6r)-2-oxo-6-(prop-1-en-2-yl)oxan-3-ylidene]deca-2,6-dien-1-yl]-6-methylcyclohexa-2,5-diene-1,4-dione

C27H34O4 (422.24569640000004)


   

12-(2-hydroxy-3,5-dimethylphenyl)-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

12-(2-hydroxy-3,5-dimethylphenyl)-6,10-dimethyl-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

C28H40O3 (424.297729)


   

2-[(3-pentyloxiran-2-yl)methyl]-3-(undeca-2,5,10-trien-1-yl)oxirane

2-[(3-pentyloxiran-2-yl)methyl]-3-(undeca-2,5,10-trien-1-yl)oxirane

C21H34O2 (318.2558664)


   

3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10-trienoic acid

3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10-trienoic acid

C20H32O3 (320.23513219999995)


   

2',4,4',6,6'-pentakis(acetyloxy)-3'-chloro-[1,1'-biphenyl]-2-yl acetate

2',4,4',6,6'-pentakis(acetyloxy)-3'-chloro-[1,1'-biphenyl]-2-yl acetate

C24H21ClO12 (536.0721496000001)


   

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

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

C27H38O4 (426.2769948)


   

2-methyl-6-[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

2-methyl-6-[(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione

C27H44O2 (400.3341124)


   

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-{2-[(2z)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl}-4-methylhex-4-en-2-one

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-{2-[(2z)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl}-4-methylhex-4-en-2-one

C27H38O5 (442.2719098)


   

(2s)-n-[(2s)-1-(acetyloxy)-3-phenylpropan-2-yl]-2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanimidic acid

(2s)-n-[(2s)-1-(acetyloxy)-3-phenylpropan-2-yl]-2-{[hydroxy(phenyl)methylidene]amino}-3-phenylpropanimidic acid

C27H28N2O4 (444.20489680000003)


   

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

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

C27H38O4 (426.2769948)


   
   

(1r,4ar,7ar)-3-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-4'-ol

(1r,4ar,7ar)-3-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-oxolan]-4'-ol

C28H40O5 (456.28755900000004)


   

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

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

C28H40O6 (472.28247400000004)


   

(2r)-2-[(3e,7e,9r)-10-hydroxy-4,8-dimethyl-9-(2-methylprop-1-en-1-yl)deca-3,7-dien-1-yl]-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

(2r)-2-[(3e,7e,9r)-10-hydroxy-4,8-dimethyl-9-(2-methylprop-1-en-1-yl)deca-3,7-dien-1-yl]-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

C27H40O3 (412.297729)


   

(1r,3s)-6-[(3e,5e,7e,9e,11e,13e,15z)-16-[(6s,7ar)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,3-diol

(1r,3s)-6-[(3e,5e,7e,9e,11e,13e,15z)-16-[(6s,7ar)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-3,7,12-trimethylheptadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-1,5,5-trimethylcyclohexane-1,3-diol

C40H56O4 (600.4178376)


   

(1r,4r,5s)-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

(1r,4r,5s)-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 (334.214398)


   

(3e,6r,10e,12r,14e)-16-(2,5-dimethoxy-3-methylphenyl)-2,12-dihydroxy-2,6,10,14-tetramethylhexadeca-3,10,14-trien-5-one

(3e,6r,10e,12r,14e)-16-(2,5-dimethoxy-3-methylphenyl)-2,12-dihydroxy-2,6,10,14-tetramethylhexadeca-3,10,14-trien-5-one

C29H44O5 (472.3188574)


   

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

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

C28H40O6 (472.28247400000004)


   

(1r,3as,3bs,5r,9ar,9bs,11ar)-5-hydroxy-1-[(2r,5e)-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

(1r,3as,3bs,5r,9ar,9bs,11ar)-5-hydroxy-1-[(2r,5e)-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 (426.34976159999997)


   

(2e,6e,10e,12s)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene-1,12-diol

(2e,6e,10e,12s)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene-1,12-diol

C20H34O2 (306.2558664)


   

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

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

C20H34O3 (322.25078140000005)


   

3-(acetyloxy)-5-[4-(acetyloxy)-2,6-bis[2,6-bis(acetyloxy)-4-[2,4,6-tris(acetyloxy)phenoxy]phenoxy]phenoxy]phenyl acetate

3-(acetyloxy)-5-[4-(acetyloxy)-2,6-bis[2,6-bis(acetyloxy)-4-[2,4,6-tris(acetyloxy)phenoxy]phenoxy]phenoxy]phenyl acetate

C62H52O31 (1292.2492442)


   

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

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

C27H38O3 (410.2820798)


   

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

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

C29H46O4 (458.3395916)


   

(4z)-6-(2,5-dihydroxy-3-methylphenyl)-1-[(1s,2s)-2-[(2e)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl]-4-methylhex-4-en-2-one

(4z)-6-(2,5-dihydroxy-3-methylphenyl)-1-[(1s,2s)-2-[(2e)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl]-4-methylhex-4-en-2-one

C27H38O5 (442.2719098)


   

(5e,9e,13r)-13-hydroxy-14-methoxy-6,10,14-trimethylpentadeca-5,9-dien-2-one

(5e,9e,13r)-13-hydroxy-14-methoxy-6,10,14-trimethylpentadeca-5,9-dien-2-one

C19H34O3 (310.25078140000005)


   

1-(2,5-dihydroxy-3-methylphenyl)-3,7,11-trimethyldodeca-2,6,10-trien-5-one

1-(2,5-dihydroxy-3-methylphenyl)-3,7,11-trimethyldodeca-2,6,10-trien-5-one

C22H30O3 (342.21948299999997)


   

(4r,5s,6e,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

(4r,5s,6e,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 (446.30320820000003)


   

(3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol

(3as,4r,7ar)-5-(2-hydroxy-2-methylpropyl)-6-[(2e)-4-(2-hydroxy-5-methoxy-3-methylphenyl)-2-methylbut-2-en-1-yl]-3a,7a-dimethyl-2,3,4,7-tetrahydro-1h-inden-4-ol

C28H42O4 (442.30829320000004)


   

2-methyl-6-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]cyclohexa-2,5-diene-1,4-dione

2-methyl-6-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]cyclohexa-2,5-diene-1,4-dione

C27H38O2 (394.28716479999997)


   

(5e,9e)-6,10,14-trimethylpentadeca-5,9,13-triene-2,12-dione

(5e,9e)-6,10,14-trimethylpentadeca-5,9,13-triene-2,12-dione

C18H28O2 (276.2089188)


   

3,7,11,15-tetramethylhexadeca-2,6,10,13,15-pentaen-1-ol

3,7,11,15-tetramethylhexadeca-2,6,10,13,15-pentaen-1-ol

C20H32O (288.24530219999997)


   

6-(2,5-dihydroxy-3-methylphenyl)-1-{2-[2-(3,3-dimethyloxiran-2-yl)acetyl]-1,2-dimethylcyclopentyl}-4-methylhex-4-en-2-one

6-(2,5-dihydroxy-3-methylphenyl)-1-{2-[2-(3,3-dimethyloxiran-2-yl)acetyl]-1,2-dimethylcyclopentyl}-4-methylhex-4-en-2-one

C27H38O5 (442.2719098)


   

(9ar,11ar)-1-[(2r,5r)-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

(9ar,11ar)-1-[(2r,5r)-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 (456.3239424)


   

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

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

C42H30O24 (918.112698)


   

(2r)-2-[(3e,7e,9s,10r)-10-hydroxy-9-methoxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

(2r)-2-[(3e,7e,9s,10r)-10-hydroxy-9-methoxy-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

C28H42O4 (442.30829320000004)


   

2-[(2e,5r,6e,10e,14z)-5,16-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-6-methylbenzene-1,4-diol

2-[(2e,5r,6e,10e,14z)-5,16-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-6-methylbenzene-1,4-diol

C27H40O4 (428.29264400000005)


   

(6z,9z,12z)-1-(2,4,6-trihydroxyphenyl)octadeca-6,9,12-trien-1-one

(6z,9z,12z)-1-(2,4,6-trihydroxyphenyl)octadeca-6,9,12-trien-1-one

C24H34O4 (386.24569640000004)


   

(6e,11e)-10-hydroxy-12-(5-hydroxy-2-methoxy-3-methylphenyl)-6,10-dimethyldodeca-6,11-diene-2,8-dione

(6e,11e)-10-hydroxy-12-(5-hydroxy-2-methoxy-3-methylphenyl)-6,10-dimethyldodeca-6,11-diene-2,8-dione

C22H30O5 (374.209313)


   

6-(2,5-dihydroxy-3-methylphenyl)-1-[2-(4-hydroxy-4-methylpent-2-enoyl)-1,2-dimethylcyclopentyl]-4-methylhex-4-en-2-one

6-(2,5-dihydroxy-3-methylphenyl)-1-[2-(4-hydroxy-4-methylpent-2-enoyl)-1,2-dimethylcyclopentyl]-4-methylhex-4-en-2-one

C27H38O5 (442.2719098)


   

3-(acetyloxy)-5-[2,4-bis(acetyloxy)-6-{[2,2',4,4',6'-pentakis(acetyloxy)-6-[2,4,6-tris(acetyloxy)phenoxy]-[1,1'-biphenyl]-3-yl]oxy}phenoxy]phenyl acetate

3-(acetyloxy)-5-[2,4-bis(acetyloxy)-6-{[2,2',4,4',6'-pentakis(acetyloxy)-6-[2,4,6-tris(acetyloxy)phenoxy]-[1,1'-biphenyl]-3-yl]oxy}phenoxy]phenyl acetate

C54H46O27 (1126.2226366)


   

2-{7-[3-(pent-2-en-1-yl)oxiran-2-yl]hepta-2,5-dien-1-yl}-3-(pent-4-en-1-yl)oxirane

2-{7-[3-(pent-2-en-1-yl)oxiran-2-yl]hepta-2,5-dien-1-yl}-3-(pent-4-en-1-yl)oxirane

C21H32O2 (316.24021719999996)


   

2-{2-[4-(3,5-dihydroxyphenoxy)-3,5-dihydroxyphenoxy]-3,5-dihydroxyphenoxy}benzene-1,3,5-triol

2-{2-[4-(3,5-dihydroxyphenoxy)-3,5-dihydroxyphenoxy]-3,5-dihydroxyphenoxy}benzene-1,3,5-triol

C24H18O12 (498.0798228)


   

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-[(1r,2r)-2-[(2e)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl]-4-methylhex-4-en-2-one

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-[(1r,2r)-2-[(2e)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl]-4-methylhex-4-en-2-one

C27H38O5 (442.2719098)


   

methyl 2-{3-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dihydroxyphenyl}acetate

methyl 2-{3-[(2e,6e,10e,12r,13s)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]-2,5-dihydroxyphenyl}acetate

C29H42O6 (486.2981232)


   

5-[2,6-dihydroxy-4-(2,4,6-trihydroxyphenoxy)phenoxy]benzene-1,2,3,4-tetrol

5-[2,6-dihydroxy-4-(2,4,6-trihydroxyphenoxy)phenoxy]benzene-1,2,3,4-tetrol

C18H14O11 (406.0536094)


   

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

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

C27H38O4 (426.2769948)


   

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

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

C28H40O4 (440.29264400000005)


   

(2s)-9-[(2r)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnon-6-enoic acid

(2s)-9-[(2r)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-2,6-dimethylnon-6-enoic acid

C22H32O4 (360.2300472)


   

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

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5s)-5-hydroperoxy-5-isopropylhept-6-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 (444.36032579999994)


   

1-(5-acetyl-2,4-dihydroxyphenyl)-3-methylbutan-1-one

1-(5-acetyl-2,4-dihydroxyphenyl)-3-methylbutan-1-one

C13H16O4 (236.10485359999998)


   

13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-triene-4,5-diol

13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,6,10-triene-4,5-diol

C27H40O4 (428.29264400000005)


   

2-{4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-furan]-3-ylmethyl}-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

2-{4a,5',5',7a-tetramethyl-6,7-dihydro-5h-spiro[cyclopenta[c]pyran-1,2'-furan]-3-ylmethyl}-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

C27H36O4 (424.2613456)


   

(3e,9r)-9-hydroxy-1-(6-methoxy-2,8-dimethylchromen-2-yl)-4,8,12-trimethyltrideca-3,11-diene-2,10-dione

(3e,9r)-9-hydroxy-1-(6-methoxy-2,8-dimethylchromen-2-yl)-4,8,12-trimethyltrideca-3,11-diene-2,10-dione

C28H38O5 (454.2719098)


   

13-(3,3-dimethyloxiran-2-yl)-3,7,11-trimethyltrideca-2,6,10-trienal

13-(3,3-dimethyloxiran-2-yl)-3,7,11-trimethyltrideca-2,6,10-trienal

C20H32O2 (304.24021719999996)


   

(1s,4r,5r)-4-[(3e,7e)-4,8,12-trimethyl-10-oxotrideca-3,7,11-trien-1-yl]-2,6-dioxabicyclo[3.1.0]hexan-3-one

(1s,4r,5r)-4-[(3e,7e)-4,8,12-trimethyl-10-oxotrideca-3,7,11-trien-1-yl]-2,6-dioxabicyclo[3.1.0]hexan-3-one

C20H28O4 (332.19874880000003)


   

7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}heptane-1,2,3,4,5,6-hexol

7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}heptane-1,2,3,4,5,6-hexol

C13H26O12 (374.14241960000004)


   

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

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

C28H40O6 (472.28247400000004)


   

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

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

C78H66O42 (1674.3028536000002)


   

2-[(2e,6e,10s,11s)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylbenzene-1,4-diol

2-[(2e,6e,10s,11s)-10,11-dihydroxy-3,7,11,15-tetramethylhexadeca-2,6,14-trien-1-yl]-6-methylbenzene-1,4-diol

C27H42O4 (430.30829320000004)


   

(9ar,11ar)-5-hydroxy-1-[(2r,5e)-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

(9ar,11ar)-5-hydroxy-1-[(2r,5e)-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 (426.34976159999997)


   

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

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

C44H38O23 (934.1803798000001)


   

5-(2-hydroxy-2-methylpropyl)-6-[(6-methoxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-3a,7a-dimethyl-1,2,3,7-tetrahydroinden-4-one

5-(2-hydroxy-2-methylpropyl)-6-[(6-methoxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)methyl]-3a,7a-dimethyl-1,2,3,7-tetrahydroinden-4-one

C28H40O4 (440.29264400000005)


   

2-(5-methoxy-5-methyloxolan-2-yl)-6,10-dimethylundeca-5,9-dien-2-ol

2-(5-methoxy-5-methyloxolan-2-yl)-6,10-dimethylundeca-5,9-dien-2-ol

C19H34O3 (310.25078140000005)


   

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

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

C20H28O4 (332.19874880000003)


   

11-(4-hydroxy-5,5-dimethyloxolan-2-yl)-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate

11-(4-hydroxy-5,5-dimethyloxolan-2-yl)-1-(2-hydroxy-5-methoxy-3-methylphenyl)-3,7-dimethyldodeca-2,6,10-trien-5-yl acetate

C30H44O6 (500.3137724)


   

6-(2,5-dimethoxy-3-methylphenyl)-1-{2,4-dimethoxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-4-methylhex-4-en-2-one

6-(2,5-dimethoxy-3-methylphenyl)-1-{2,4-dimethoxy-6,7,9,9-tetramethylbicyclo[4.2.1]nona-2,4-dien-7-yl}-4-methylhex-4-en-2-one

C31H44O5 (496.3188574)


   

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

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

C29H46O4 (458.3395916)


   

(2e,6e,10e)-12-(2,5-dihydroxy-3-methylphenyl)-6,10-dimethyl-2-(4-methyl-3-oxopent-4-en-1-yl)dodeca-2,6,10-trienoic acid

(2e,6e,10e)-12-(2,5-dihydroxy-3-methylphenyl)-6,10-dimethyl-2-(4-methyl-3-oxopent-4-en-1-yl)dodeca-2,6,10-trienoic acid

C27H36O5 (440.2562606)


   

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

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

C18H14O9 (374.06377940000004)


   

3-(acetyloxy)-5-[4-(acetyloxy)-2,6-bis({[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy})phenoxy]phenyl acetate

3-(acetyloxy)-5-[4-(acetyloxy)-2,6-bis({[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy})phenoxy]phenyl acetate

C66H56O33 (1376.2703726)


   

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-{2-[(2e)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl}-4-methylhex-4-en-2-one

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-{2-[(2e)-4-hydroxy-4-methylpent-2-enoyl]-1,2-dimethylcyclopentyl}-4-methylhex-4-en-2-one

C27H38O5 (442.2719098)


   

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

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

C36H26O21 (794.0966546)


   

(2e,7e)-10-[(2r)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-3,7-dimethyl-2-(2-methylprop-1-en-1-yl)deca-2,7-dienal

(2e,7e)-10-[(2r)-6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]-3,7-dimethyl-2-(2-methylprop-1-en-1-yl)deca-2,7-dienal

C27H38O3 (410.2820798)


   

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

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

C54H46O28 (1142.2175516)


   

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

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

C18H34O16 (506.1846764)


   
   

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

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

C27H40O4 (428.29264400000005)


   

3-(acetyloxy)-5-[2,6-bis(acetyloxy)-4-[4-(acetyloxy)-2,6-bis[2,4,6-tris(acetyloxy)phenoxy]phenoxy]phenoxy]phenyl acetate

3-(acetyloxy)-5-[2,6-bis(acetyloxy)-4-[4-(acetyloxy)-2,6-bis[2,4,6-tris(acetyloxy)phenoxy]phenoxy]phenoxy]phenyl acetate

C52H44O26 (1084.2120724000001)


   

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

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

C27H38O4 (426.2769948)


   

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

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

C24H18O12 (498.0798228)


   

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

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

C29H48O (412.37049579999996)


   

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

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

C29H46O3 (442.34467659999996)


   

(6e,10e,14r)-14-hydroxy-2,6,10-trimethylpentadeca-2,6,10-trien-4-one

(6e,10e,14r)-14-hydroxy-2,6,10-trimethylpentadeca-2,6,10-trien-4-one

C18H30O2 (278.224568)


   

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

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

C27H38O4 (426.2769948)


   

(2r)-2-[(3e,7e)-10-hydroxy-4,8-dimethyl-9-(2-methylprop-1-en-1-yl)deca-3,7-dien-1-yl]-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

(2r)-2-[(3e,7e)-10-hydroxy-4,8-dimethyl-9-(2-methylprop-1-en-1-yl)deca-3,7-dien-1-yl]-2,8-dimethyl-3,4-dihydro-1-benzopyran-6-ol

C27H40O3 (412.297729)


   

(2e,6e,10e)-6,10-dimethyl-12-(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

(2e,6e,10e)-6,10-dimethyl-12-(5-methyl-3,6-dioxocyclohexa-1,4-dien-1-yl)-2-(4-methylpent-3-en-1-yl)dodeca-2,6,10-trienoic acid

C27H36O4 (424.2613456)


   

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

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

C28H42O5 (458.30320820000003)


   

5-(acetyloxy)-3-{[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy}-2-[3,4,5-tris(acetyloxy)phenoxy]phenyl acetate

5-(acetyloxy)-3-{[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy}-2-[3,4,5-tris(acetyloxy)phenoxy]phenyl acetate

C46H40O24 (976.1909440000001)


   

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

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

C42H30O24 (918.112698)


   

2-[3,4-dihydroxy-5-(3,4,5-trihydroxyphenoxy)phenoxy]benzene-1,3,5-triol

2-[3,4-dihydroxy-5-(3,4,5-trihydroxyphenoxy)phenoxy]benzene-1,3,5-triol

C18H14O10 (390.05869440000004)


   

(4r,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

(4r,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 (428.29264400000005)


   

(3r,6r)-1,4-dimethyl-3-[(4-{[(1e)-3-methylbut-1-en-1-yl]oxy}phenyl)methyl]-3,6-bis(methylsulfanyl)piperazine-2,5-dione

(3r,6r)-1,4-dimethyl-3-[(4-{[(1e)-3-methylbut-1-en-1-yl]oxy}phenyl)methyl]-3,6-bis(methylsulfanyl)piperazine-2,5-dione

C20H28N2O3S2 (408.15412580000003)


   

(4r,10e)-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

(4r,10e)-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 (428.29264400000005)


   

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

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

C20H34O2 (306.2558664)


   

3-[7-(6-hydroxy-2,8-dimethylchromen-2-yl)-4-methylhept-4-en-1-ylidene]-6-(2-hydroxypropan-2-yl)oxan-2-one

3-[7-(6-hydroxy-2,8-dimethylchromen-2-yl)-4-methylhept-4-en-1-ylidene]-6-(2-hydroxypropan-2-yl)oxan-2-one

C27H36O5 (440.2562606)


   

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

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

C27H38O3 (410.2820798)


   

(7s,10r)-12-[(2z)-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

(7s,10r)-12-[(2z)-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 (442.2719098)


   

(6s,7s,9z)-nonadeca-9,18-diene-6,7-diol

(6s,7s,9z)-nonadeca-9,18-diene-6,7-diol

C19H36O2 (296.2715156)


   

(1s,3as,3bs,7s,9ar,9bs,11as)-7-hydroxy-1-[(2s)-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

(1s,3as,3bs,7s,9ar,9bs,11as)-7-hydroxy-1-[(2s)-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 (428.3290274)


   

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

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

C13H28AsO12P (482.05342780000007)


   

14-hydroxy-2,6,10-trimethylpentadec-10-en-4-one

14-hydroxy-2,6,10-trimethylpentadec-10-en-4-one

C18H34O2 (282.2558664)


   

(3r,4as,5r)-5,8-dihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-2-benzopyran-1-one

(3r,4as,5r)-5,8-dihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-2-benzopyran-1-one

C10H14O4 (198.0892044)


   

(2e,7s,10e,12r)-3,7,11,15-tetramethylhexadeca-2,10,14-triene-1,7,12-triol

(2e,7s,10e,12r)-3,7,11,15-tetramethylhexadeca-2,10,14-triene-1,7,12-triol

C20H36O3 (324.26643060000004)


   

8-(5-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-6-methyloct-5-en-2-one

8-(5-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-6-methyloct-5-en-2-one

C18H30O2 (278.224568)


   

(10e)-9-hydroxy-1-(2,4,6-trihydroxyphenyl)octadeca-6,10,12,15-tetraen-1-one

(10e)-9-hydroxy-1-(2,4,6-trihydroxyphenyl)octadeca-6,10,12,15-tetraen-1-one

C24H32O5 (400.2249622)


   

henicosa-1,6,9,12,15,18-hexaene

henicosa-1,6,9,12,15,18-hexaene

C21H32 (284.2503872)


   

(3ar,7ar)-5-(2-hydroxy-2-methylpropyl)-6-{[(2r)-6-methoxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]methyl}-3a,7a-dimethyl-1,2,3,7-tetrahydroinden-4-one

(3ar,7ar)-5-(2-hydroxy-2-methylpropyl)-6-{[(2r)-6-methoxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]methyl}-3a,7a-dimethyl-1,2,3,7-tetrahydroinden-4-one

C28H40O4 (440.29264400000005)


   

(4r,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

(4r,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 (428.29264400000005)


   

3,7-dimethyl-11-oxododeca-2,6-dien-1-yl acetate

3,7-dimethyl-11-oxododeca-2,6-dien-1-yl acetate

C16H26O3 (266.1881846)


   

methyl 2-(2-{[(3r,6e,11r,12s,13r)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-1,6,14-trien-3-yl]oxy}-5-hydroxyphenyl)acetate

methyl 2-(2-{[(3r,6e,11r,12s,13r)-12,13-dihydroxy-3,7,11,15-tetramethylhexadeca-1,6,14-trien-3-yl]oxy}-5-hydroxyphenyl)acetate

C29H44O6 (488.3137724)


   

8-(5-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-6-methyloct-5-en-2-one

8-(5-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-6-methyloct-5-en-2-one

C18H30O2 (278.224568)


   

methyl 1-hydroxy-4-methoxy-2-oxocyclopent-3-ene-1-carboxylate

methyl 1-hydroxy-4-methoxy-2-oxocyclopent-3-ene-1-carboxylate

C8H10O5 (186.052821)


   

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

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

C27H38O5 (442.2719098)


   

(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(2s,3z)-2-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione

(1s,3as,3bs,5as,9ar,9bs,11as)-1-[(2s,3z)-2-hydroxy-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-dodecahydro-1h-cyclopenta[a]phenanthrene-5,7-dione

C27H42O3 (414.3133782)


   

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

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

C48H34O24 (994.1439964)


   

2-methyl-6-[3,7,11-trimethyl-12-(4-methylfuran-2-yl)-5-oxododeca-2,6,10-trien-1-yl]cyclohexa-2,5-diene-1,4-dione

2-methyl-6-[3,7,11-trimethyl-12-(4-methylfuran-2-yl)-5-oxododeca-2,6,10-trien-1-yl]cyclohexa-2,5-diene-1,4-dione

C27H32O4 (420.2300472)


   

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

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

C27H40O4 (428.29264400000005)


   

2-methyl-6-(3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)cyclohexa-2,5-diene-1,4-dione

2-methyl-6-(3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl)cyclohexa-2,5-diene-1,4-dione

C27H38O2 (394.28716479999997)


   

2-(4-{4'-hydroxy-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-methylbenzene-1,4-diol

2-(4-{4'-hydroxy-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-methylbenzene-1,4-diol

C27H38O5 (442.2719098)


   

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

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

C28H40O5 (456.28755900000004)


   

3-(acetyloxy)-5-[4-(acetyloxy)-2-[2,6-bis(acetyloxy)-4-[2,4,6-tris(acetyloxy)phenoxy]phenoxy]-6-[2,6-bis(acetyloxy)-4-{[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy}phenoxy]phenoxy]phenyl acetate

3-(acetyloxy)-5-[4-(acetyloxy)-2-[2,6-bis(acetyloxy)-4-[2,4,6-tris(acetyloxy)phenoxy]phenoxy]-6-[2,6-bis(acetyloxy)-4-{[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy}phenoxy]phenoxy]phenyl acetate

C74H62O37 (1542.2969802)


   

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

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

C20H32O2 (304.24021719999996)


   

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

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

C20H32O3 (320.23513219999995)


   

(2r)-6-methoxy-2,5,8-trimethyl-2-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-1-benzopyran

(2r)-6-methoxy-2,5,8-trimethyl-2-[(3e,7e)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-1-benzopyran

C29H44O2 (424.3341124)


   

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

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

C60H42O30 (1242.1760832)


   

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

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

C18H30O2 (278.224568)


   

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

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

C27H42O4 (430.30829320000004)


   

(4s,6ar,9ar)-2-[(2e)-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

(4s,6ar,9ar)-2-[(2e)-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 (456.28755900000004)


   

(3as,7ar)-5-(2-hydroxy-2-methylpropyl)-6-{[(2s)-6-methoxy-2,8-dimethylchromen-2-yl]methyl}-3a,7a-dimethyl-1,2,3,7-tetrahydroinden-4-one

(3as,7ar)-5-(2-hydroxy-2-methylpropyl)-6-{[(2s)-6-methoxy-2,8-dimethylchromen-2-yl]methyl}-3a,7a-dimethyl-1,2,3,7-tetrahydroinden-4-one

C28H38O4 (438.2769948)


   

5-[(3s)-3-hydroxybutanoyl]-4-methoxy-6-methylpyran-2-one

5-[(3s)-3-hydroxybutanoyl]-4-methoxy-6-methylpyran-2-one

C11H14O5 (226.08411940000002)


   

4-[(2r,3s)-3-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-3-methyloxiran-2-yl]butan-2-one

4-[(2r,3s)-3-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-3-methyloxiran-2-yl]butan-2-one

C18H30O2 (278.224568)


   

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

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

C27H40O3 (412.297729)


   

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

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

C28H40O6 (472.28247400000004)


   

nonadeca-1,10,13,16-tetraene

nonadeca-1,10,13,16-tetraene

C19H32 (260.2503872)


   

1-(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

1-(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 (444.36032579999994)


   

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

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

C48H33ClO24 (1028.1050248000001)


   

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

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

C28H40O6 (472.28247400000004)


   

14-hydroxy-2,6,10-trimethylpentadeca-5,10-dien-4-one

14-hydroxy-2,6,10-trimethylpentadeca-5,10-dien-4-one

C18H32O2 (280.2402172)


   

(2s,3s,5s)-5-[(1s)-1-hydroxydec-9-en-1-yl]-2-pentyloxolan-3-ol

(2s,3s,5s)-5-[(1s)-1-hydroxydec-9-en-1-yl]-2-pentyloxolan-3-ol

C19H36O3 (312.26643060000004)


   

methyl 2-{2,5-dihydroxy-3-[(2e,6e,10e,13s)-13-hydroxy-3,7,11,15-tetramethyl-12-oxohexadeca-2,6,10,14-tetraen-1-yl]phenyl}acetate

methyl 2-{2,5-dihydroxy-3-[(2e,6e,10e,13s)-13-hydroxy-3,7,11,15-tetramethyl-12-oxohexadeca-2,6,10,14-tetraen-1-yl]phenyl}acetate

C29H40O6 (484.28247400000004)


   

4-[2-(5-bromo-2-oxo-1h-indol-3-ylidene)hydrazin-1-yl]benzenesulfonamide

4-[2-(5-bromo-2-oxo-1h-indol-3-ylidene)hydrazin-1-yl]benzenesulfonamide

C14H11BrN4O3S (393.97351960000003)


   

2-methyl-6-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzene-1,4-diol

2-methyl-6-[(2e,6e,10e)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]benzene-1,4-diol

C27H40O2 (396.302814)


   

4-[5-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2-methylpent-2-en-1-yl]-2-methyl-5-(2-methylprop-1-en-1-yl)cyclopent-2-en-1-one

4-[5-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2-methylpent-2-en-1-yl]-2-methyl-5-(2-methylprop-1-en-1-yl)cyclopent-2-en-1-one

C27H36O3 (408.26643060000004)


   

2-[(2z,4e,6e,8e,10e,12e,14e,16e)-17-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol

2-[(2z,4e,6e,8e,10e,12e,14e,16e)-17-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14,16-octaen-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol

C40H56O4 (600.4178376)


   

5,8-dihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-2-benzopyran-1-one

5,8-dihydroxy-3-methyl-3,4,4a,5,6,7-hexahydro-2-benzopyran-1-one

C10H14O4 (198.0892044)


   

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

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

C48H34O24 (994.1439964)


   

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

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

C42H30O21 (870.1279529999999)


   

3-(acetyloxy)-5-[2,6-bis(acetyloxy)-4-[2,4-bis(acetyloxy)-6-[2,4,6-tris(acetyloxy)phenoxy]phenoxy]phenoxy]phenyl acetate

3-(acetyloxy)-5-[2,6-bis(acetyloxy)-4-[2,4-bis(acetyloxy)-6-[2,4,6-tris(acetyloxy)phenoxy]phenoxy]phenoxy]phenyl acetate

C42H36O21 (876.1749006)


   

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

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

C27H38O3 (410.2820798)


   

10-(5,5-dimethyloxolan-2-yl)-6-methylundeca-5,9-dien-2-one

10-(5,5-dimethyloxolan-2-yl)-6-methylundeca-5,9-dien-2-one

C18H30O2 (278.224568)


   

(5z,10e,14s)-14-hydroxy-2,6,10-trimethylpentadeca-5,10-dien-4-one

(5z,10e,14s)-14-hydroxy-2,6,10-trimethylpentadeca-5,10-dien-4-one

C18H32O2 (280.2402172)


   

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

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

C30H22O15 (622.0958662)


   

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

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

C28H44O2 (412.3341124)


   

(2s,3s,5r)-5-[(1s)-1-hydroxydec-9-en-1-yl]-2-pentyloxolan-3-yl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate

(2s,3s,5r)-5-[(1s)-1-hydroxydec-9-en-1-yl]-2-pentyloxolan-3-yl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate

C39H66O4 (598.4960836)


   

2-methyl-6-[(2e,6z,10e)-3,7,11-trimethyl-12-(4-methylfuran-2-yl)-5-oxododeca-2,6,10-trien-1-yl]cyclohexa-2,5-diene-1,4-dione

2-methyl-6-[(2e,6z,10e)-3,7,11-trimethyl-12-(4-methylfuran-2-yl)-5-oxododeca-2,6,10-trien-1-yl]cyclohexa-2,5-diene-1,4-dione

C27H32O4 (420.2300472)


   

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

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

C30H22O17 (654.0856962)


   

(3e,7e)-10-[(2r)-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

(3e,7e)-10-[(2r)-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 (426.2769948)


   

(2e,6e)-2-(3-chloro-4-methylpent-4-en-1-yl)-9-(6-hydroxy-2,8-dimethylchromen-2-yl)-6-methylnona-2,6-dienoic acid

(2e,6e)-2-(3-chloro-4-methylpent-4-en-1-yl)-9-(6-hydroxy-2,8-dimethylchromen-2-yl)-6-methylnona-2,6-dienoic acid

C27H35ClO4 (458.22237400000006)


   

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

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

C48H34O24 (994.1439964)


   

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

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

C45H74O5 (694.5535954)


   

(2e,6z,10e)-1-(2,5-dihydroxy-3-methylphenyl)-3,7,11-trimethyl-12-(4-methylfuran-2-yl)dodeca-2,6,10-trien-5-one

(2e,6z,10e)-1-(2,5-dihydroxy-3-methylphenyl)-3,7,11-trimethyl-12-(4-methylfuran-2-yl)dodeca-2,6,10-trien-5-one

C27H34O4 (422.24569640000004)


   

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-{2-[2-(3,3-dimethyloxiran-2-yl)acetyl]-1,2-dimethylcyclopentyl}-4-methylhex-4-en-2-one

(4e)-6-(2,5-dihydroxy-3-methylphenyl)-1-{2-[2-(3,3-dimethyloxiran-2-yl)acetyl]-1,2-dimethylcyclopentyl}-4-methylhex-4-en-2-one

C27H38O5 (442.2719098)


   

13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,10-diene-6,7-diol

13-(6-hydroxy-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl)-2,6,10-trimethyltrideca-2,10-diene-6,7-diol

C27H42O4 (430.30829320000004)


   

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

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

C60H42O35 (1322.1506582000002)


   

(3e,5z)-octa-1,3,5-triene

(3e,5z)-octa-1,3,5-triene

C8H12 (108.09389519999999)


   

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

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

C54H38O27 (1118.1600398)


   

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

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

C30H22O17 (654.0856962)


   

(4as,6ar,8s,10as,10br)-3,4a,7,7,10a-pentamethyl-1h,5h,6h,6ah,8h,9h,10h,10bh-cyclohexa[f]chromen-8-ol

(4as,6ar,8s,10as,10br)-3,4a,7,7,10a-pentamethyl-1h,5h,6h,6ah,8h,9h,10h,10bh-cyclohexa[f]chromen-8-ol

C18H30O2 (278.224568)


   

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

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

C36H26O19 (762.1068246)


   

methyl 2-(5-hydroxy-2-{[(6e,13e)-12-hydroxy-3,7,11,15-tetramethylhexadeca-1,6,13,15-tetraen-3-yl]oxy}phenyl)acetate

methyl 2-(5-hydroxy-2-{[(6e,13e)-12-hydroxy-3,7,11,15-tetramethylhexadeca-1,6,13,15-tetraen-3-yl]oxy}phenyl)acetate

C29H42O5 (470.30320820000003)


   

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

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

C27H42O4 (430.30829320000004)


   

[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]acetic acid

[(1r)-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]acetic acid

C11H16O3 (196.1099386)


   

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

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

C60H42O30 (1242.1760832)


   

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

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

C27H38O2 (394.28716479999997)


   

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

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

C27H38O4 (426.2769948)


   

3,4a,7,7,10a-pentamethyl-1h,5h,6h,6ah,8h,9h,10h,10bh-cyclohexa[f]chromen-8-ol

3,4a,7,7,10a-pentamethyl-1h,5h,6h,6ah,8h,9h,10h,10bh-cyclohexa[f]chromen-8-ol

C18H30O2 (278.224568)


   

3-(acetyloxy)-5-{[2,2',4,4',6'-pentakis(acetyloxy)-6-[2,6-bis(acetyloxy)-4-{[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy}phenoxy]-[1,1'-biphenyl]-3-yl]oxy}phenyl acetate

3-(acetyloxy)-5-{[2,2',4,4',6'-pentakis(acetyloxy)-6-[2,6-bis(acetyloxy)-4-{[2,2',4,4',6,6'-hexakis(acetyloxy)-[1,1'-biphenyl]-3-yl]oxy}phenoxy]-[1,1'-biphenyl]-3-yl]oxy}phenyl acetate

C66H56O33 (1376.2703726)


   

2-methyl-6-[(2e,5e)-3-methyl-7-oxoocta-2,5-dien-1-yl]cyclohexa-2,5-diene-1,4-dione

2-methyl-6-[(2e,5e)-3-methyl-7-oxoocta-2,5-dien-1-yl]cyclohexa-2,5-diene-1,4-dione

C16H18O3 (258.1255878)


   

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

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

C36H26O18 (746.1119096)


   

3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraenal

3,7,11,15-tetramethyl-13-oxohexadeca-2,6,10,14-tetraenal

C20H30O2 (302.224568)


   

6-amino-6-carboxy-2-(trimethylammonio)hexanoate

6-amino-6-carboxy-2-(trimethylammonio)hexanoate

C10H20N2O4 (232.1423)


   

(2e,6e,10e,13e)-3,7,11,15-tetramethylhexadeca-2,6,10,13,15-pentaen-1-ol

(2e,6e,10e,13e)-3,7,11,15-tetramethylhexadeca-2,6,10,13,15-pentaen-1-ol

C20H32O (288.24530219999997)


   

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

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

C20H34O2 (306.2558664)


   

(1r,3r,3as,4's,6ar)-3-{2-[(2s)-6-(acetyloxy)-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]acetyl}-3a,5',5',6a-tetramethyl-tetrahydrospiro[cyclopenta[c]furan-1,2'-oxolan]-4'-yl acetate

(1r,3r,3as,4's,6ar)-3-{2-[(2s)-6-(acetyloxy)-2,8-dimethyl-3,4-dihydro-1-benzopyran-2-yl]acetyl}-3a,5',5',6a-tetramethyl-tetrahydrospiro[cyclopenta[c]furan-1,2'-oxolan]-4'-yl acetate

C31H42O8 (542.2879532000001)


   

(3as,7ar)-5-(2-hydroxy-2-methylpropyl)-3a,6,7a-trimethyl-1,2,3,7-tetrahydroinden-4-one

(3as,7ar)-5-(2-hydroxy-2-methylpropyl)-3a,6,7a-trimethyl-1,2,3,7-tetrahydroinden-4-one

C16H26O2 (250.1932696)


   

3,5-bis(acetyloxy)-2-chlorophenyl acetate

3,5-bis(acetyloxy)-2-chlorophenyl acetate

C12H11ClO6 (286.0244136)


   

2',4,4',6,6'-pentakis(acetyloxy)-3'-[3,4,5-tris(acetyloxy)-2-[3,5-bis(acetyloxy)-4-[3,4,5-tris(acetyloxy)phenoxy]phenoxy]phenoxy]-[1,1'-biphenyl]-2-yl acetate

2',4,4',6,6'-pentakis(acetyloxy)-3'-[3,4,5-tris(acetyloxy)-2-[3,5-bis(acetyloxy)-4-[3,4,5-tris(acetyloxy)phenoxy]phenoxy]phenoxy]-[1,1'-biphenyl]-2-yl acetate

C58H50O31 (1242.233595)


   

3-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-methoxy-5-methylphenol

3-[(2e)-3,7-dimethylocta-2,6-dien-1-yl]-4-methoxy-5-methylphenol

C18H26O2 (274.1932696)


   

(4e)-1-[(1r,2r)-1,2-dimethyl-2-(4-methylpent-3-enoyl)cyclopentyl]-6-(5-hydroxy-2-methoxy-3-methylphenyl)-4-methylhex-4-en-2-one

(4e)-1-[(1r,2r)-1,2-dimethyl-2-(4-methylpent-3-enoyl)cyclopentyl]-6-(5-hydroxy-2-methoxy-3-methylphenyl)-4-methylhex-4-en-2-one

C28H40O4 (440.29264400000005)