NCBI Taxonomy: 6544

Fucoxanthin

C42H58O6 (658.4233)

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

L-Tyrosine

C9H11NO3 (181.0739)

Tyrosine (Tyr) or L-tyrosine 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-tyrosine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Tyrosine is found in all organisms ranging from bacteria to plants to animals. It is classified as a non-polar, uncharged (at physiological pH) aromatic amino acid. Tyrosine is a non-essential amino acid, meaning the body can synthesize it – usually from phenylalanine. The conversion of phenylalanine to tyrosine is catalyzed by the enzyme phenylalanine hydroxylase, a monooxygenase. This enzyme catalyzes the reaction causing the addition of a hydroxyl group to the end of the 6-carbon aromatic ring of phenylalanine, such that it becomes tyrosine. Tyrosine is found in many high-protein food products such as chicken, turkey, fish, milk, yogurt, cottage cheese, cheese, peanuts, almonds, pumpkin seeds, sesame seeds, soy products, lima beans, avocados and bananas. Tyrosine is one of the few amino acids that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, including thyroid hormones (diiodotyrosine), catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism have been identified, such as hawkinsinuria and tyrosinemia I. The most common feature of these diseases is the increased amount of tyrosine in the blood, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements can help reverse these disease symptoms. Some adults also develop elevated tyrosine in their blood. This typically indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can help aleviate biochemical depression. However, tyrosine may not be good for treating psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-Dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-Dopa (http://www.dcnutrition.com). In addition to its role as a precursor for neurotransmitters, tyrosine plays an important role for the function of many proteins. Within many proteins or enzymes, certain tyrosine residues can be tagged (at the hydroxyl group) with a phosphate group (phosphorylated) by specialized protein kinases. In its phosphorylated form, tyrosine is called phosphotyrosine. Tyrosine phosphorylation is considered to be one of the key steps in signal transduction and regulation of enzymatic activity. Tyrosine (or its precursor phenylalanine) is also needed to synthesize the benzoquinone structure which forms part of coenzyme Q10. L-tyrosine is an optically active form of tyrosine having L-configuration. It has a role as an EC 1.3.1.43 (arogenate dehydrogenase) inhibitor, a nutraceutical, a micronutrient and a fundamental metabolite. It is an erythrose 4-phosphate/phosphoenolpyruvate family amino acid, a proteinogenic amino acid, a tyrosine and a L-alpha-amino acid. It is functionally related to a L-tyrosinal. It is a conjugate base of a L-tyrosinium. It is a conjugate acid of a L-tyrosinate(1-). It is an enantiomer of a D-tyrosine. It is a tautomer of a L-tyrosine zwitterion. Tyrosine is a non-essential amino acid. In animals it is synthesized from [phenylalanine]. It is also the precursor of [epinephrine], thyroid hormones, and melanin. L-Tyrosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). L-Tyrosine is the levorotatory isomer of the aromatic amino acid tyrosine. L-tyrosine is a naturally occurring tyrosine and is synthesized in vivo from L-phenylalanine. It is considered a non-essential amino acid; however, in patients with phenylketonuria who lack phenylalanine hydroxylase and cannot convert phenylalanine into tyrosine, it is considered an essential nutrient. In vivo, tyrosine plays a role in protein synthesis and serves as a precursor for the synthesis of catecholamines, thyroxine, and melanin. Tyrosine is an essential amino acid that readily passes the blood-brain barrier. Once in the brain, it is a precursor for the neurotransmitters dopamine, norepinephrine and epinephrine, better known as adrenalin. These neurotransmitters are an important part of the bodys sympathetic nervous system, and their concentrations in the body and brain are directly dependent upon dietary tyrosine. Tyrosine is not found in large concentrations throughout the body, probably because it is rapidly metabolized. Folic acid, copper and vitamin C are cofactor nutrients of these reactions. Tyrosine is also the precursor for hormones, thyroid, catecholestrogens and the major human pigment, melanin. Tyrosine is an important amino acid in many proteins, peptides and even enkephalins, the bodys natural pain reliever. Valine and other branched amino acids, and possibly tryptophan and phenylalanine may reduce tyrosine absorption. A number of genetic errors of tyrosine metabolism occur. Most common is the increased amount of tyrosine in the blood of premature infants, which is marked by decreased motor activity, lethargy and poor feeding. Infection and intellectual deficits may occur. Vitamin C supplements reverse the disease. Some adults also develop elevated tyrosine in their blood. This indicates a need for more vitamin C. More tyrosine is needed under stress, and tyrosine supplements prevent the stress-induced depletion of norepinephrine and can cure biochemical depression. However, tyrosine may not be good for psychosis. Many antipsychotic medications apparently function by inhibiting tyrosine metabolism. L-dopa, which is directly used in Parkinsons, is made from tyrosine. Tyrosine, the nutrient, can be used as an adjunct in the treatment of Parkinsons. Peripheral metabolism of tyrosine necessitates large doses of tyrosine, however, compared to L-dopa. A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin. Dietary supplement, nutrient. Flavouring ingredient. L-Tyrosine is found in many foods, some of which are blue crab, sweet rowanberry, lemon sole, and alpine sweetvetch. An optically active form of tyrosine having L-configuration. L-Tyrosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=60-18-4 (retrieved 2024-07-01) (CAS RN: 60-18-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

Protodioscin

C51H84O22 (1048.5454)

Protodioscin is a spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc attached to position 3 of 26-(beta-D-glucopyranosyloxy)-3beta,22-dihydroxyfurost-5-ene via a glycosidic linkage. Found in several plant species including yams, asparagus and funugreek. It has a role as a metabolite. It is a steroid saponin, a trisaccharide derivative, a beta-D-glucoside, a pentacyclic triterpenoid and a cyclic hemiketal. It is functionally related to a diosgenin. It derives from a hydride of a spirostan. Protodioscin is a natural product found in Dracaena draco, Borassus flabellifer, and other organisms with data available. See also: Fenugreek seed (part of). Asparasaponin I is found in fenugreek. Asparasaponin I is a bitter principle from white asparagus shoots (Asparagus officinalis) and fenugreek (Trigonella foenum-graecum From Asparagus officinalis (asparagus) Protodioscin, a major steroidal saponin in Trigonella foenum-graecum Linn., has been shown to exhibit multiple biological actions, such as anti-hyperlipidemia, anti-cancer, sexual effects and cardiovascular properties. Protodioscin, a major steroidal saponin in Trigonella foenum-graecum Linn., has been shown to exhibit multiple biological actions, such as anti-hyperlipidemia, anti-cancer, sexual effects and cardiovascular properties.

Ergosterol

C28H44O (396.3392)

Ergosterol is a phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. It has a role as a fungal metabolite and a Saccharomyces cerevisiae metabolite. It is a 3beta-sterol, an ergostanoid, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL. Ergosterol is a natural product found in Gladiolus italicus, Ramaria formosa, and other organisms with data available. ergosterol is a metabolite found in or produced by Saccharomyces cerevisiae. A steroid occurring in FUNGI. Irradiation with ULTRAVIOLET RAYS results in formation of ERGOCALCIFEROL (vitamin D2). See also: Reishi (part of). Ergosterol, also known as provitamin D2, 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, ergosterol is considered to be a sterol lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes. A phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. Ergosterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-87-4 (retrieved 2024-07-12) (CAS RN: 57-87-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

Campesterol

C28H48O (400.3705)

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

Stigmasterol

C29H48O (412.3705)

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

beta-Carotene

C40H56 (536.4382)

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

Lutein

C40H56O2 (568.428)

Lutein is a common carotenoid xanthophyll found in nature. Carotenoids are among the most common pigments in nature and are natural lipid-soluble antioxidants. Lutein is one of the two carotenoids (the other is zeaxanthin) 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 cataracts (up to 20\\\\\%) and 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). Lutein is a carotenol. It has a role as a food colouring and a plant metabolite. It derives from a hydride of a (6R)-beta,epsilon-carotene. Lutein is an xanthophyll and one of 600 known naturally occurring carotenoids. Lutein is synthesized only by plants and like other xanthophylls is found in high quantities in green leafy vegetables such as spinach, kale and yellow carrots. In green plants, xanthophylls act to modulate light energy and serve as non-photochemical quenching agents to deal with triplet chlorophyll (an excited form of chlorophyll), which is overproduced at very high light levels, during photosynthesis. Lutein is a natural product found in Eupatorium cannabinum, Hibiscus syriacus, and other organisms with data available. Lutein is lutein (LOO-teen) is a oxygenated carotenoid found in vegetables and fruits. lutein is found in the macula of the eye, where it is believed to act as a yellow filter. Lutein acts as an antioxidant, protecting cells against the damaging effects of free radicals. A xanthophyll found in the major LIGHT-HARVESTING PROTEIN COMPLEXES of plants. Dietary lutein accumulates in the MACULA LUTEA. See also: Calendula Officinalis Flower (part of); Corn (part of); Chicken; lutein (component of) ... View More ... Pigment from egg yolk and leaves. Found in all higher plants. Nutriceutical with anticancer and antioxidation props. Potentially useful for the treatment of age-related macular degeneration (AMD) of the eye Lutein A. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=127-40-2 (retrieved 2024-07-12) (CAS RN: 127-40-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Lutein (Xanthophyll) is a carotenoid with reported anti-inflammatory properties. A large body of evidence shows that lutein has several beneficial effects, especially on eye health[1]. Lutein exerts its biological activities, including anti-inflammation, anti-oxidase and anti-apoptosis, through effects on reactive oxygen species (ROS)[2][3]. Lutein is able to arrive in the brain and shows antidepressant-like and neuroprotective effects. Lutein is orally active[4]. Lutein (Xanthophyll) is a carotenoid with reported anti-inflammatory properties. A large body of evidence shows that lutein has several beneficial effects, especially on eye health[1]. Lutein exerts its biological activities, including anti-inflammation, anti-oxidase and anti-apoptosis, through effects on reactive oxygen species (ROS)[2][3]. Lutein is able to arrive in the brain and shows antidepressant-like and neuroprotective effects. Lutein is orally active[4].

Astaxanthin

C40H52O4 (596.3865)

Astaxanthin (pronounced as-tuh-zan-thin) is a carotenoid. It belongs to a larger class of phytochemicals known as terpenes. It is classified as a xanthophyll, which means "yellow leaves". Like many carotenoids, it is a colorful, lipid-soluble pigment. Astaxanthin is produced by microalgae, yeast, salmon, trout, krill, shrimp, crayfish, crustaceans, and the feathers of some birds. Professor Basil Weedon was the first to map the structure of astaxanthin.; Astaxanthin is the main carotenoid pigment found in aquatic animals. It is also found in some birds, such as flamingoes, quails, and other species. This carotenoid is included in many well-known seafoods such as salmon, trout, red seabream, shrimp, lobster, and fish eggs. Astaxanthin, similar to other carotenoids, cannot be synthesized by animals and must be provided in the diet. Mammals, including humans, lack the ability to synthesize astaxanthin or to convert dietary astaxanthin into vitamin A. Astaxanthin belongs to the xanthophyll class of carotenoids. It is closely related to beta-carotene, lutein, and zeaxanthin, sharing with them many of the general metabolic and physiological functions attributed to carotenoids. In addition, astaxanthin has unique chemical properties based on its molecular structure. The presence of the hydroxyl (OH) and keto (CdO) moieties on each ionone ring explains some of its unique features, namely, the ability to be esterified and a higher antioxidant activity and a more polar nature than other carotenoids. In its free form, astaxanthin is considerably unstable and particularly susceptible to oxidation. Hence it is found in nature either conjugated with proteins (e.g., salmon muscle or lobster exoskeleton) or esterified with one or two fatty acids (monoester and diester forms), which stabilize the molecule. Various astaxanthin isomers have been characterized on the basis of the configuration of the two hydroxyl groups on the molecule. the geometrical and optical isomers of astaxanthin are distributed selectively in different tissues and that levels of free astaxanthin in the liver are greater than the corresponding concentration in the plasma, suggesting concentrative uptake by the liver. Astaxanthin, similar to other carotenoids, is a very lipophilic compound and has a low oral bioavailability. This criterion has limited the ability to test this compound in well-defined rodent models of human disease. (PMID: 16562856); Astaxanthin is a carotenoid widely used in salmonid and crustacean aquaculture to provide the pink color characteristic of that species. This application has been well documented for over two decades and is currently the major market driver for the pigment. Additionally, astaxanthin also plays a key role as an intermediary in reproductive processes. Synthetic astaxanthin dominates the world market but recent interest in natural sources of the pigment has increased substantially. Common sources of natural astaxanthin are the green algae Haematococcus pluvialis, the red yeast, Phaffia rhodozyma, as well as crustacean byproducts. Astaxanthin possesses an unusual antioxidant activity which has caused a surge in the nutraceutical market for the encapsulated productand is) also, health benefits such as cardiovascular disease prevention, immune system boosting, bioactivity against Helycobacter pylori, and cataract prevention, have been associated with astaxanthin consumption. Research on the health benefits of astaxanthin is very recent and has mostly been performed in vitro or at the pre-clinical level with humans. (PMID: 16431409); Astaxanthin, unlike some carotenoids, does not convert to Vitamin A (retinol) in the human body. Too much Vitamin A is toxic for a human, but astaxanthin is not. However, it is a powerful antioxidant; it is claimed to be 10 times more capable than other carotenoids. However, other sources suggest astaxanthin has slightly lower antioxidant activity than other carotenoids.; While astaxanthin is a natural nutr... Astaxanthin is the main carotenoid pigment found in aquatic animals. It is also found in some birds, such as flamingoes, quails, and other species. This carotenoid is included in many well-known seafoods such as salmon, trout, red seabream, shrimp, lobster, and fish eggs. Astaxanthin, similar to other carotenoids, cannot be synthesized by animals and must be provided in the diet. Mammals, including humans, lack the ability to synthesize astaxanthin or to convert dietary astaxanthin into vitamin A. Astaxanthin belongs to the xanthophyll class of carotenoids. It is closely related to beta-carotene, lutein, and zeaxanthin, sharing with them many of the general metabolic and physiological functions attributed to carotenoids. In addition, astaxanthin has unique chemical properties based on its molecular structure. The presence of the hydroxyl (OH) and keto (CdO) moieties on each ionone ring explains some of its unique features, namely, the ability to be esterified and a higher antioxidant activity and a more polar nature than other carotenoids. In its free form, astaxanthin is considerably unstable and particularly susceptible to oxidation. Hence it is found in nature either conjugated with proteins (e.g. salmon muscle or lobster exoskeleton) or esterified with one or two fatty acids (monoester and diester forms) which stabilize the molecule. Various astaxanthin isomers have been characterized on the basis of the configuration of the two hydroxyl groups on the molecule. The geometrical and optical isomers of astaxanthin are distributed selectively in different tissues and levels of free astaxanthin in the liver are greater than the corresponding concentration in the plasma, suggesting concentrative uptake by the liver. Astaxanthin, similar to other carotenoids, is a very lipophilic compound and has a low oral bioavailability. This criterion has limited the ability to test this compound in well-defined rodent models of human disease (PMID: 16562856). Astaxanthin is a carotenoid widely used in salmonid and crustacean aquaculture to provide the pink colour characteristic of that species. This application has been well documented for over two decades and is currently the major market driver for the pigment. Additionally, astaxanthin also plays a key role as an intermediary in reproductive processes. Synthetic astaxanthin dominates the world market but recent interest in natural sources of the pigment has increased substantially. Common sources of natural astaxanthin are the green algae Haematococcus pluvialis (the red yeast), Phaffia rhodozyma, as well as crustacean byproducts. Astaxanthin possesses an unusual antioxidant activity which has caused a surge in the nutraceutical market for the encapsulated product. Also, health benefits such as cardiovascular disease prevention, immune system boosting, bioactivity against Helicobacter pylori, and cataract prevention, have been associated with astaxanthin consumption. Research on the health benefits of astaxanthin is very recent and has mostly been performed in vitro or at the pre-clinical level with humans (PMID: 16431409). Astaxanthin is used in fish farming to induce trout flesh colouring. Astaxanthin is a carotenone that consists of beta,beta-carotene-4,4-dione bearing two hydroxy substituents at positions 3 and 3 (the 3S,3S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein. It has a role as an anticoagulant, an antioxidant, a food colouring, a plant metabolite and an animal metabolite. It is a carotenone and a carotenol. It derives from a hydride of a beta-carotene. Astaxanthin is a keto-carotenoid in the terpenes class of chemical compounds. It is classified as a xanthophyll but it is a carotenoid with no vitamin A activity. It is found in the majority of aquatic organisms with red pigment. Astaxanthin has shown to mediate anti-oxidant and anti-inflammatory actions. It may be found in fish feed or some animal food as a color additive. Astaxanthin is a natural product found in Ascidia zara, Linckia laevigata, and other organisms with data available. Astaxanthin is a natural and synthetic xanthophyll and nonprovitamin A carotenoid, with potential antioxidant, anti-inflammatory and antineoplastic activities. Upon administration, astaxanthin may act as an antioxidant and reduce oxidative stress, thereby preventing protein and lipid oxidation and DNA damage. By decreasing the production of reactive oxygen species (ROS) and free radicals, it may also prevent ROS-induced activation of nuclear factor-kappa B (NF-kB) transcription factor and the production of inflammatory cytokines such as interleukin-1beta (IL-1b), IL-6 and tumor necrosis factor-alpha (TNF-a). In addition, astaxanthin may inhibit cyclooxygenase-1 (COX-1) and nitric oxide (NO) activities, thereby reducing inflammation. Oxidative stress and inflammation play key roles in the pathogenesis of many diseases, including cardiovascular, neurological, autoimmune and neoplastic diseases. A carotenone that consists of beta,beta-carotene-4,4-dione bearing two hydroxy substituents at positions 3 and 3 (the 3S,3S diastereomer). A carotenoid pigment found mainly in animals (crustaceans, echinoderms) but also occurring in plants. It can occur free (as a red pigment), as an ester, or as a blue, brown or green chromoprotein. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids C308 - Immunotherapeutic Agent > C210 - Immunoadjuvant C2140 - Adjuvant

beta-Elemene

C15H24 (204.1878)

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

alpha-Carotene

C40H56 (536.4382)

alpha-Carotene belongs to the class of organic compounds known as carotenes. These are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They 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. alpha-Carotene is considered to be an isoprenoid lipid molecule. alpha-Carotene is one of the primary isomers of carotene. Plasma levels of alpha-carotene are positively associated with the detection rate of AFB1-DNA adducts in a dose-dependent manner, whereas plasma lycopene level was inversely related to the presence of the adducts in urine (PMID: 9214602). (6R)-beta,epsilon-carotene is an alpha-carotene. It is an enantiomer of a (6S)-beta,epsilon-carotene. alpha-Carotene is a natural product found in Hibiscus syriacus, Scandix stellata, and other organisms with data available. Widespread carotenoid, e.g. in carrots and palm oil. Has vitamin A activity but less than that of b-Carotene A cyclic carotene with a beta- and an epsilon-ring at opposite ends respectively. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Zeaxanthin

C40H56O2 (568.428)

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

Sugiol

C20H28O2 (300.2089)

Sugiol is an abietane diterpenoid that is ferruginol in which the methylene group para to the phenolic hydroxy group has been substituted by an oxo group. It has a role as a plant metabolite, an antiviral agent, an antineoplastic agent, an antioxidant and a radical scavenger. It is an abietane diterpenoid, a carbotricyclic compound, a meroterpenoid, a member of phenols and a cyclic terpene ketone. It is functionally related to a ferruginol. Sugiol is a natural product found in Austrocedrus chilensis, Libocedrus bidwillii, and other organisms with data available. An abietane diterpenoid that is ferruginol in which the methylene group para to the phenolic hydroxy group has been substituted by an oxo group.

L-Arginine

C6H14N4O2 (174.1117)

Arginine (Arg), also known as L-argninine, belongs to the class of organic compounds known as L-alpha-amino acids. These are alpha amino acids which have the L-configuration of the alpha-carbon atom. 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-asparagine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Arginine is found in all organisms ranging from bacteria to plants to animals. Arginine is an essential amino acid that is physiologically active in the L-form. It is classified as a charged, basic, aliphatic amino acid. Arginine is considered to be a basic amino acid as it has a strongly basic guanidinium group. With a pKa of 12.48, the guanidinium group is positively charged in neutral, acidic, and even most basic environments. Because of the conjugation between the double bond and the nitrogen lone pairs, the positive charge is delocalized. This group is able to form multiple H-bonds. In mammals, arginine is formally classified as a semi-essential or conditionally essential amino acid, depending on the developmental stage and health status of the individual. Infants are unable to effectively synthesize arginine, making it nutritionally essential for infants. Adults, however, are able to synthesize arginine in the urea cycle. L-Arginine is an amino acid that has numerous functions in the body. It helps dispose of ammonia, is used to make compounds such as nitric oxide, creatine, L-glutamate, and L-proline, and it can be converted into glucose and glycogen if needed. Arginine also plays an important role in cell division, immunity and wound healing. Arginine is the immediate precursor of nitric oxide (NO), an important signaling molecule which can act as a second messenger, as well as an intercellular messenger which regulates vasodilation, and also has functions in the immune systems reaction to infection. Nitric oxide is made via the enzyme nitric oxide synthase (PMID 10690324). Arginine is also a precursor for several important nitrogen-containing compounds including urea, ornithine, and agmatine. Arginine is necessary for the synthesis of creatine and can be used for the synthesis of polyamines (mainly through ornithine and to a lesser degree through agmatine, citrulline, and glutamate.) The presence of asymmetric dimethylarginine (ADMA) in serum or plasma, a close relative of argninine, inhibits the nitric oxide synthase reaction. ADMA is considered a marker for vascular disease, just as L-arginine is considered a sign of a healthy endothelium. In large doses, L-arginine also stimulates the release of the hormones growth hormone and prolactin. Arginine is a known inducer of mTOR (mammalian target of rapamycin) and is responsible for inducing protein synthesis through the mTOR pathway. mTOR inhibition by rapamycin partially reduces arginine-induced protein synthesis (PMID: 20841502). Catabolic disease states such as sepsis, injury, and cancer cause an increase in arginine utilization, which can exceed normal body production, leading to arginine depletion. Arginine also activates AMP kinase (AMPK) which then stimulates skeletal muscle fatty acid oxidation and muscle glucose uptake, thereby increasing insulin secretion by pancreatic beta-cells (PMID: 21311355). Arginine is found in plant and animal proteins, such as dairy products, meat, poultry, fish, and nuts. The ratio of L-arginine to lysine is also important: soy and other plant proteins have more L-arginine than animal sources of protein. [Spectral] L-Arginine (exact mass = 174.11168) and L-Histidine (exact mass = 155.06948) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. L-Arginine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=74-79-3 (retrieved 2024-06-29) (CAS RN: 74-79-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

Morphine

C17H19NO3 (285.1365)

Morphine, also known as (-)-morphine or morphine sulfate, is a member of the class of compounds known as morphinans. Morphinans are polycyclic compounds with a four-ring skeleton with three condensed six-member rings forming a partially hydrogenated phenanthrene moiety, one of which is aromatic while the two others are alicyclic. Morphine is soluble (in water) and a very weakly acidic compound (based on its pKa). Morphine can be synthesized from morphinan. Morphine is also a parent compound for other transformation products, including but not limited to, myrophine, heroin, and codeine. Morphine can be found in a number of food items such as nanking cherry, eggplant, millet, and common hazelnut, which makes morphine a potential biomarker for the consumption of these food products. Morphine can be found primarily in blood and urine, as well as in human kidney and liver tissues. In humans, morphine is involved in several metabolic pathways, some of which include heroin action pathway, morphine metabolism pathway, heroin metabolism pathway, and codeine metabolism pathway. Morphine is a non-carcinogenic (not listed by IARC) potentially toxic compound. Morphine is a drug which is used for the relief and treatment of severe pain. The primary source of morphine is isolation from poppy straw of the opium poppy. In 2013, an estimated 523 000 kg of morphine were produced. About 45 000 kg were used directly for pain, a four-time increase over the last twenty years. Most use for this purpose was in the developed world. About 70\\% of morphine is used to make other opioids such as hydromorphone, oxymorphone, and heroin. It is a Schedule II drug in the United States, Class A in the United Kingdom, and Schedule I in Canada. It is on the World Health Organizations List of Essential Medicines, the most effective and safe medicines needed in a health system. Morphine is sold under many trade names . Primarily hepatic (90\\%), converted to dihydromorphinone and normorphineand is) also converted to morphine-3-glucuronide (M3G) and morphine-6-glucuronide. Virtually all morphine is converted to glucuronide metabolites; only a small fraction (less than 5\\%) of absorbed morphine is demethylated (DrugBank). In the treatment of morphine overdosage, primary attention should be given to the re- establishment of a patent airway and institution of assisted or controlled ventilation. Supportive measures (including oxygen, vasopressors) should be employed in the management of circulatory shock and pulmonary edema accompanying overdose as indicated. Cardiac arrest or arrhythmias may require cardiac massage or defibrillation. The pure opioid antagonists, such as naloxone, are specific antidotes against respiratory depression which results from opioid overdose. Naloxone should be administered intravenously; however, because its duration of action is relatively short, the patient must be carefully monitored until spontaneous respiration is reliably re-established. If the response to naloxone is suboptimal or not sustained, additional naloxone may be administered, as needed, or given by continuous infusion to maintain alertness and respiratory function; however, there is no information available about the cumulative dose of naloxone that may be safely administered (L1712) (T3DB). Morphine is the principal alkaloid in opium and the prototype opiate analgesic and narcotic. In 2017, morphine was the 155th most commonly prescribed medication in the United States, with more than four million prescriptions. Morphine is used primarily to treat both acute and chronic severe pain. Its duration of analgesia is about three to seven hours. A large overdose of morphine can cause asphyxia and death by respiratory depression if the person does not receive medical attention immediately. Morphine is naturally produced by several plants (such as the opium poppy) and animals (PMID: 22578954). Morphine was first isolated between 1803 and 1805 by Friedrich Sertürner. Sertürner originally named the substance morphium after the Greek god of dreams, Morpheus, as it has a tendency to cause sleep. The primary source of morphine is isolation from poppy straw of the opium poppy. Morphine is also endogenously produced by humans. In the mid 2000s it was found morphine can be synthesized by white blood cells (PMID 22578954). CYP2D6, a cytochrome P450 isoenzyme, catalyzes the biosynthesis of morphine from codeine and dopamine from tyramine. The morphine biosynthetic pathway in humans occurs as follows: L-tyrosine -> para-tyramine or L-DOPA -> dopamine -> (S)-norlaudanosoline -> (S)-reticuline -> 1,2-dehydroretinulinium -> (R)-reticuline -> salutaridine -> salutaridinol -> thebaine -> neopinone -> codeinone -> codeine -> morphine. (S)-Norlaudanosoline (also known as tetrahydropapaveroline) which is an important intermediate in the WBC biosynthesis of morphine can also be synthesized from 3,4-dihydroxyphenylacetaldehyde (DOPAL), a metabolite of L-DOPA and dopamine. Morphine has widespread effects in the central nervous system and on smooth muscle (PMID: 4582903). The precise mechanism of the analgesic action of morphine is not fully known. However, specific CNS opiate receptors have been identified and likely play a role in the induction of analgesic effects. Morphine first acts on the mu-opioid receptors. The mechanism of respiratory depression involves a reduction in the responsiveness of the brain stem respiratory centers to increases in carbon dioxide tension and electrical stimulation. It has been shown that morphine binds to and inhibits GABA inhibitory interneurons. These interneurons normally inhibit the descending pain inhibition pathway. So, without the inhibitory signals, pain modulation can proceed downstream. When the dose of morphine is reduced after long-term use, opioid withdrawal symptoms such as drowsiness, vomiting, and constipation may also occur (PMID: 23244430). Morphine is only found in easily detectable quantities in individuals that have used or taken this drug. D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist > C1657 - Opiate N - Nervous system > N02 - Analgesics > N02A - Opioids > N02AA - Natural opium alkaloids relative retention time with respect to 9-anthracene Carboxylic Acid is 0.056 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics CONFIDENCE standard compound; EAWAG_UCHEM_ID 2744 CONFIDENCE standard compound; INTERNAL_ID 1580

Morphine-6-glucuronide

C23H27NO9 (461.1686)

Morphine-6-glucuronide (M6G) is a major active metabolite of morphine, and as such is the molecule responsible for much of the pain-relieving effects of morphine (and thus heroin). M6G is formed from morphine by the enzyme UDP-Glucuronosyltransferase-2B7 (UGT2B7). M6G can accumulate to toxic levels in kidney failure. D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist > C1657 - Opiate

Cyanidin 3-glucoside

[C21H21O11]+ (449.1084)

Cyanidin 3-glucoside, also known as chrysanthenin or cyanidin 3-glucoside chloride (CAS: 7084-24-4), belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in redcurrants, strawberries, and sweet oranges. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as common pea, peaches, Tartary buckwheats, soft-necked garlic, and fats and oils. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods. Cyanidin (and its glycosides) is the most commonly occurring of the anthocyanins, a widespread group of pigments responsible for the red-blue colour of many fruits and vegetables (PMID: 14711454). BioTransformer predicts that cyanidin 3-​glucoside is a product of cyanidin 3-​sophoroside metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by the EC.3.2.1.X enzyme (PMID: 30612223). Acquisition and generation of the data is financially supported in part by CREST/JST. Found in many plants and fruits, e.g. cherries, olives and grapes

Cholesterol

C27H46O (386.3548)

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

Violaxanthin

C40H56O4 (600.4178)

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

Canthaxanthin

C40H52O2 (564.3967)

Canthaxanthin, also known as Cantaxanthin, Cantaxanthine, or Canthaxanthine is a keto-carotenoid, a pigment widely distributed in nature. Carotenoids belong to a larger class of phytochemicals known as terpenoids. Canthaxanin is also classified as a xanthophyll. Xanthophylls are yellow pigments and form one of two major divisions of the carotenoid group; the other division is formed by the carotenes. Both are carotenoids. Xanthophylls and carotenes are similar in structure, but xanthophylls contain oxygen atoms while carotenes are purely hydrocarbons, which do not contain oxygen. Their content of oxygen causes xanthophylls to be more polar (in molecular structure) than carotenes and causes their separation from carotenes in many types of chromatography. (Carotenes are usually more orange in color than xanthophylls. Canthaxanthin is naturally found in bacteria, algae and some fungi. Canthaxanthin is associated with E number E161g and is approved for use as a food coloring agent in different countries, including the United States and the EU. Canthaxanthin is used as poultry feed additive to yield red color in skin and yolks. The European Union permits the use of canthaxanthin in feedstuff at a maximum content of 25 mg/kg of final feedstuff while the United States allows the use of this pigment in broiler chicken and salmonid fish feeds. Canthoxanthin was first isolated in edible chanterelle mushroom (Cantharellus cinnabarinus), from which it derived its name. It has also been found in green algae, bacteria, archea (a halophilic archaeon called Haloferax alexandrines), fungi and bioaccumulates in tissues and egg yolk from wild birds and at low levels in crustaceans and fish such as carp, golden grey mullet, and seabream. Canthaxanthin is not found in wild Atlantic Salmon, but is a minor carotenoid in Pacific Salmon. Canthaxanthin is used in farm-raised trout to give a red/orange color to their flesh similar to wild trout. Canthaxanthin has been used as a food additive for egg yolk, in cosmetics and as a pigmenting agent for human skin applications. It has also been used as a feed additive in fish and crustacean farms. Canthaxanthin is a potent lipid-soluble antioxidant (PMID: 2505240). Canthaxanthin increases resistance to lipid peroxidation primarily by enhancing membrane alpha-tocopherol levels and secondarily by providing weak direct antioxidant activity. Canthaxanthin biosynthesis in bacteria and algae proceeds from beta-carotene via the action of an enzyme known as a beta-carotene ketolase, that is able to add a carbonyl group to carbon 4 and 4 of the beta carotene molecule. Food colouring. Constituent of the edible mushroom (Cantharellus cinnabarinus), sea trout, salmon and brine shrimp. It is used in broiler chicken feed to enhance the yellow colour of chicken skin D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

echinenone

C40H54O (550.4174)

A carotenone that is beta-carotene in which the 4 position has undergone formal oxidation to afford the corresponding ketone. Isolated as orange-red crystals, it is widely distributed in marine invertebrates. 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.

alpha-Selinene

C15H24 (204.1878)

Occurs in celery oil and hop (Humulus lupulus) oil. alpha-Selinene is found in many foods, some of which are ginger, lovage, sweet bay, and allspice. alpha-Selinene is found in alcoholic beverages. alpha-Selinene occurs in celery oil and hop (Humulus lupulus) oi

Longifolene

C15H24 (204.1878)

Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily Liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73¬∞. The other enantiomer (optical rotation ‚àí42.73¬∞) is found in small amounts in certain fungi and liverworts . Longifolene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Longifolene is a sweet, fir needle, and medical tasting compound found in corn, mandarin orange (clementine, tangerine), rosemary, and star anise, which makes longifolene a potential biomarker for the consumption of these food products. Longifolene is the common (or trivial) chemical name of a naturally occurring, oily liquid hydrocarbon found primarily in the high-boiling fraction of certain pine resins. The name is derived from that of a pine species from which the compound was isolated, Pinus longifolia (obsolete name for Pinus roxburghii Sarg.) Chemically, longifolene is a tricyclic sesquiterpene. This molecule is chiral, and the enantiomer commonly found in pines and other higher plants exhibits a positive optical rotation of +42.73°. The other enantiomer (optical rotation −42.73°) is found in small amounts in certain fungi and liverworts . (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1]. (+)-Longifolene is a sesquiterpenoid and a metabolite in rabbits. (+)-Longifolen is converted to primary, secondary or tertiary alcohols in rabbits, among which the primary alcohol is predominant[1].

7-Dehydrocholesterol

C27H44O (384.3392)

7-Dehydrocholesterol (7-DHC), also known as provitamin D3 or 5,7-cholestadien-3-b-ol, belongs to the class of organic compounds known as cholesterols and derivatives. Cholesterols and derivatives are compounds containing a 3-hydroxylated cholestane core. Thus, 7-dehydrocholesterol is also classified as a sterol. 7-Dehydrocholesterol is known as a zoosterol, meaning that it is a sterol isolated from animals (to distinguish those sterols isolated from plants which are called phytosterols). 7-DHC functions in the serum as a cholesterol precursor and is photochemically converted to vitamin D3 in the skin. Therefore 7-DHC functions as provitamin-D3. The presence of 7-DHC in human skin enables humans and other mammals to manufacture vitamin D3 (cholecalciferol) from ultraviolet rays in the sun light, via an intermediate isomer pre-vitamin D3. 7-DHC absorbs UV light most effectively at wavelengths between 290 and 320 nm and, thus, the production of vitamin D3 will occur primarily at those wavelengths (PMID: 9625080). The two most important factors that govern the generation of pre-vitamin D3 are the quantity (intensity) and quality (appropriate wavelength) of the UVB irradiation reaching the 7-dehydrocholesterol deep in the stratum basale and stratum spinosum (PMID: 9625080). 7-DHC is also found in the milk of several mammalian species, including cows (PMID: 10999630; PMID: 225459). It was discovered by Nobel-laureate organic chemist Adolf Windaus. 7-DHC can be produced by animals and plants via different pathways (PMID: 23717318). It is not produced by fungi in significant amounts. 7-DHC is made by some algae and can also be produced by some bacteria. 7-Dehydrocholesterol is a zoosterol (a sterol produced by animals rather than plants). It is a provitamin-D. The presence of this compound in skin enables humans to manufacture vitamin D3 from ultra-violet rays in the sun light, via an intermediate isomer provitamin D3. It is also found in breast milk. [HMDB] D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins 7-Dehydrocholesterol is biosynthetic precursor of cholesterol and vitamin D3. 7-Dehydrocholesterol is biosynthetic precursor of cholesterol and vitamin D3.

Desmosterol

C27H44O (384.3392)

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

Okadaic acid

C44H68O13 (804.466)

Okadaic acid is found in mollusks. Okadaic acid is found in the marine sponges Halichondria okadai and Halichondria melanodocia and shellfish. It is a metabolite of Prorocentrum lima. It is a diarrhetic shellfish toxin. Okadaic acid is a toxin that accumulates in bivalves and causes diarrhetic shellfish poisoning. The molecular formula of okadaic acid, which is a derivative of a C38 fatty acid, is C44H68O13. The IUPAC name of okadaic acid is (2R)-2-hydroxy-3-{(2S,5R,6R,8S)-5-hydroxy-[(1R,2E)-3-((2R,5R,6S,8R,8aS)-8-hydroxy-6-{(1S,3S)-1-hydroxy-3-[(3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl}-7-methyleneoctahydro-3H,3H-spiro[furan-2,2-pyrano[3,2-b]pyran]-5-yl)-1-methylprop-2-en-1-yl]-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl}-2-methylpropanoic acid. Okadaic acid was named from the marine sponge Halichondria okadai, from which okadaic acid was isolated for the first time. It has also been isolated from another marine sponge, H. malanodocia, as a cytotoxin. The real producer of okadaic acid is a marine dinoflagellate D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins D009676 - Noxae > D002273 - Carcinogens D049990 - Membrane Transport Modulators D004791 - Enzyme Inhibitors D007476 - Ionophores

3-Epicycloeucalenol

C30H50O (426.3861)

3-Epicycloeucalenol is found in fruits. 3-Epicycloeucalenol is a constituent of Musa sapientum (banana) fruit peel Constituent of Musa sapientum (banana) fruit peel. 3-Epicycloeucalenol is found in fruits.

arcaine

C6H16N6 (172.1436)

D007004 - Hypoglycemic Agents > D001645 - Biguanides

Cyclokievitone

C20H18O6 (354.1103)

Isolated from pods of Phaseolus vulgaris (kidney bean) and from other Phaseolus subspecies Cyclokievitone is found in many foods, some of which are green bean, common bean, pulses, and mung bean. Cyclokievitone is found in common bean. Cyclokievitone is isolated from pods of Phaseolus vulgaris (kidney bean) and from other Phaseolus species.

Domoic acid

C15H21NO6 (311.1369)

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

24-Methylenecholesterol

C28H46O (398.3548)

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

Yessotoxin

C55H82O21S2 (1142.479)

Yessotoxin is found in mollusks. Toxic constituent of scallops (Patinopecten yessoensis). Toxic constituent of scallops (Patinopecten yessoensis). Yessotoxin is found in mollusks. D009676 - Noxae > D011042 - Poisons > D008978 - Mollusk Venoms D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins D009676 - Noxae > D011042 - Poisons > D014688 - Venoms

Azaspiracid

C47H71NO12 (841.4976)

D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins

Diadinoxanthin

C40H54O3 (582.4073)

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

D-Tyrosine

C9H11NO3 (181.0739)

Poriferasterol

C29H48O (412.3705)

Alloxanthin

C40H52O2 (564.3967)

Alloxanthin is found in channel catfish. Alloxanthin is a constituent of many shellfish including the giant scallop (Pecten maximus) and edible mussel (Mytilus edulis). Constituent of many shellfish including the giant scallop (Pecten maximus) and edible mussel (Mytilus edulis). Alloxanthin is found in channel catfish and mollusks.

Mytiloxanthin

C40H54O4 (598.4022)

Mytiloxanthin is found in blue mussel. Mytiloxanthin is isolated from the mussels Mytilus edulis. Isolated from the mussels Mytilus edulis. Mytiloxanthin is found in blue mussel and mollusks.

Sugiol

C20H28O2 (300.2089)

Sugiol is found in fruits. Sugiol is a constituent of Juniperus communis (juniper). Constituent of Juniperus communis (juniper). Sugiol is found in fruits.

Azaspiracid

C47H71NO12 (841.4976)

Azaspiracid is found in mollusks. Azaspiracid is an alkaloid from Mytilus edulis (blue mussel). Shellfish toxin. Alkaloid from Mytilus edulis (blue mussel). Shellfish toxin. Azaspiracid is found in mollusks.

Spirolide D

C43H65NO7 (707.4761)

Spirolide D is found in mollusks. Spirolide D is isolated from Mytilus edulis (blue mussel

Dinophysistoxin 2

C44H68O13 (804.466)

Dinophysistoxin 2 is found in mollusks. Dinophysistoxin 2 is a metabolite of Dinophysis species. Metabolite of Dinophysis subspecies Dinophysistoxin 2 is found in mollusks. D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins

alpha-Caryophyllene

C15H24 (204.1878)

α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1]. α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1].

1-Palmitoylphosphatidylcholine

C24H50NO7P (495.3325)

Peridinin

C39H50O7 (630.3556)

Poriferasterol

C29H48O (412.3705)

Arginine

C6H14N4O2 (174.1117)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

Halocynthiaxanthin

C40H54O4 (598.4022)

D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids 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. This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.

Pinnatoxin A

C41H61NO9 (711.4346)

Pectenolone

C40H52O3 (580.3916)

Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan.

Astaxanthin

C40H52O4 (596.3865)

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. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids C308 - Immunotherapeutic Agent > C210 - Immunoadjuvant C2140 - Adjuvant

Stigmasterol

C29H48O (412.3705)

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

Cyclokievitone

C20H18O6 (354.1103)

Peridinin

C39H50O7 (630.3556)

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

4-Ketoalloxanthin

C40H50O3 (578.376)

Yessotoxin

C55H82O21S2 (1142.479)

Pectenol B

C40H54O3 (582.4073)

okadaic acid

C44H68O13 (804.466)

D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins D009676 - Noxae > D002273 - Carcinogens D049990 - Membrane Transport Modulators D004791 - Enzyme Inhibitors D007476 - Ionophores A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.

5-(hydroxymethyl)-2-methoxybenzene-1,3-diol

C8H10O4 (170.0579)

Cholesterol

C27H46O (386.3548)

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

3,3-DIMETHYLPENTANE

C7H16 (100.1252)

Arginine

C6H14N4O2 (174.1117)

An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.047 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.045 Acquisition and generation of the data is financially supported by the Max-Planck-Society L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

Campesterol

C28H48O (400.3705)

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

Ergosterol

C28H44O (396.3392)

Indicator of fungal contamination, especies in cereals. Occurs in yeast and fungi. The main fungal steroidand is also found in small amts. in higher plant prods., e.g. palm oil [DFC]. D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins 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. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

β-Carotene

C40H56 (536.4382)

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

L-Arginine

C6H14N4O2 (174.1117)

An L-alpha-amino acid that is the L-isomer of arginine. MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; ODKSFYDXXFIFQN-BYPYZUCNSA-N_STSL_0099_L-Arginine_8000fmol_180506_S2_LC02_MS02_67; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2]. L-Arginine ((S)-(+)-Arginine) is the substrate for the endothelial nitric oxide synthase (eNOS) to generate NO. L-Arginine is transported into vascular smooth muscle cells by the cationic amino acid transporter family of proteins where it is metabolized to nitric oxide (NO), polyamines, or L-proline[1][2].

L-Tyrosine

C9H11NO3 (181.0739)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OUYCCCASQSFEME-QMMMGPOBSA-N_STSL_0110_L-Tyrosine_0500fmol_180506_S2_LC02_MS02_57; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex. L-Tyrosine is a non-essential amino acid which can inhibit citrate synthase activity in the posterior cortex.

Agmatine

C5H14N4 (130.1218)

Cyanidin 3-glucoside

[C21H21O11]+ (449.1084)

Violaxanthin

C40H56O4 (600.4178)

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

Zeaxanthin

C40H56O2 (568.428)

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

α-Carotene

C40H56 (536.4382)

Domoic acid

C15H21NO6 (311.1369)

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

7-Dehydrocholesterol

C27H44O (384.3392)

D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins 7-Dehydrocholesterol is biosynthetic precursor of cholesterol and vitamin D3. 7-Dehydrocholesterol is biosynthetic precursor of cholesterol and vitamin D3.

Fucoxanthin

C42H58O6 (658.4233)

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

Lysophosphatidylcholines, egg

C24H50NO7P (495.3325)

Alloxanthin

C40H52O2 (564.3967)

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.

Desmosterol

C27H44O (384.3392)

caryophyllene

C15H24 (204.1878)

A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

pyrrhoxanthin

C39H48O6 (612.3451)

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

Mytiloxanthin

C40H54O4 (598.4022)

Pectenol A/ (Pectenol)

C40H54O3 (582.4073)

Amarouciaxanthin B/ Sidnyaxanthin

C40H52O4 (596.3865)

Loroxanthin/ 19-Hydroxylutein

C40H56O3 (584.4229)

a-Selinene

C15H24 (204.1878)

Beta-Elemene

C15H24 (204.1878)

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

canthaxanthin

C40H52O2 (564.3967)

A carotenone that consists of beta,beta-carotene bearing two oxo substituents at positions 4 and 4. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

(R,R)-Astaxanthin

C40H52O4 (596.3865)

2-aminoethanesulfonic acid

C2H7NO3S (125.0147)

2-amino-3-(4-hydroxyphenyl)propanoic acid

C9H11NO3 (181.0739)

Elemene

C15H24 (204.1878)

(-)-beta-elemene, also known as elemene or 2,4-diisopropenyl-1-methyl-1-vinylcyclohexane, is a member of the class of compounds known as elemane sesquiterpenoids. Elemane sesquiterpenoids are sesquiterpenoids with a structure based on the elemane skeleton. Elemane is a monocyclic compound consisting of a cyclohexane ring substituted with a methyl group, an ethyl group, and two 1-methylethyl groups at the 1-, 1-, 2-, and 4-position, respectively (-)-beta-elemene can be found in herbs and spices and root vegetables, which makes (-)-beta-elemene a potential biomarker for the consumption of these food products.

Dinophysistoxin 2

C44H68O13 (804.466)

A ketal that is a rare marine toxin structurally related to okadaic acid. Found yearly along with okadaic acid in Portuguese shellfish, its presence has been correlated with the occurrence of Dinophysis acta. D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins

Ovothiol B

C8H13N3O2S (215.0728)

A L-histidine derivative that is N-methyl-L-histidine substituted at positions N3 and C5 on the imidazole ring by methyl and mercapto groups respectively.

Humulene

C15H24 (204.1878)

α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1]. α-Humulene is a main constituent of Tanacetum vulgare L. (Asteraceae) essential oil with anti-inflammation (IC50=15±2 μg/mL). α-Humulene inhibits COX-2 and iNOS expression[1].

Caryophyllene oxide

C15H24O (220.1827)

Constituent of oil of cloves (Eugenia caryophyllata)and is) also in oils of Betula alba, Mentha piperita (peppermint) and others. Caryophyllene alpha-oxide is found in many foods, some of which are spearmint, cloves, ceylon cinnamon, and herbs and spices. Caryophyllene beta-oxide is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Caryophyllene beta-oxide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, caryophyllene beta-oxide is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1]. Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1].

Cyanidin 3-glucoside

C21H21O11+ (449.1084)

Cyanidin 3-glucoside, also known as chrysanthenin or cyanidin 3-glucoside chloride (CAS: 7084-24-4), belongs to the class of organic compounds known as pyranones and derivatives. Pyranones and derivatives are compounds containing a pyran ring which bears a ketone. Cyanidin 3-glucoside is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, cyanidin 3-glucoside is found, on average, in the highest concentration within a few different foods, such as black elderberries, rubus (blackberry, raspberry), and bilberries and in a lower concentration in redcurrants, strawberries, and sweet oranges. Cyanidin 3-glucoside has also been detected, but not quantified in, several different foods, such as common pea, peaches, Tartary buckwheats, soft-necked garlic, and fats and oils. This could make cyanidin 3-glucoside a potential biomarker for the consumption of these foods. Cyanidin (and its glycosides) is the most commonly occurring of the anthocyanins, a widespread group of pigments responsible for the red-blue colour of many fruits and vegetables (PMID: 14711454). BioTransformer predicts that cyanidin 3-​glucoside is a product of cyanidin 3-​sophoroside metabolism via a glycoside-hydrolysis reaction occurring in human gut microbiota and catalyzed by the EC.3.2.1.X enzyme (PMID: 30612223). Found in many plants and fruits, e.g. cherries, olives and grapes

Protodioscin

C51H84O22 (1048.5454)

Protodioscin is a spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc attached to position 3 of 26-(beta-D-glucopyranosyloxy)-3beta,22-dihydroxyfurost-5-ene via a glycosidic linkage. Found in several plant species including yams, asparagus and funugreek. It has a role as a metabolite. It is a steroid saponin, a trisaccharide derivative, a beta-D-glucoside, a pentacyclic triterpenoid and a cyclic hemiketal. It is functionally related to a diosgenin. It derives from a hydride of a spirostan. Protodioscin is a natural product found in Dracaena draco, Borassus flabellifer, and other organisms with data available. See also: Fenugreek seed (part of). A spirostanyl glycoside that consists of the trisaccharide alpha-L-Rha-(1->4)-[alpha-L-Rha-(1->2)]-beta-D-Glc attached to position 3 of 26-(beta-D-glucopyranosyloxy)-3beta,22-dihydroxyfurost-5-ene via a glycosidic linkage. Found in several plant species including yams, asparagus and funugreek. Protodioscin, a major steroidal saponin in Trigonella foenum-graecum Linn., has been shown to exhibit multiple biological actions, such as anti-hyperlipidemia, anti-cancer, sexual effects and cardiovascular properties. Protodioscin, a major steroidal saponin in Trigonella foenum-graecum Linn., has been shown to exhibit multiple biological actions, such as anti-hyperlipidemia, anti-cancer, sexual effects and cardiovascular properties.

Morphine

C17H19NO3 (285.1365)

A morphinane alkaloid that is a highly potent opiate analgesic psychoactive drug. Morphine acts directly on the central nervous system (CNS) to relieve pain but has a high potential for addiction, with tolerance and both physical and psychological dependence developing rapidly. Morphine is the most abundant opiate found in Papaver somniferum (the opium poppy). D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D009294 - Narcotics D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist > C1657 - Opiate N - Nervous system > N02 - Analgesics > N02A - Opioids > N02AA - Natural opium alkaloids D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics

Morphine-6-glucuronide

C23H27NO9 (461.1686)

D002492 - Central Nervous System Depressants > D009294 - Narcotics > D053610 - Opiate Alkaloids C78272 - Agent Affecting Nervous System > C67413 - Opioid Receptor Agonist > C1657 - Opiate

Dihydrocholesterol

C27H48O (388.3705)

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

19'-Hexanoyloxyfucoxanthinol

C46H66O7 (730.4808)

(1r,5r,6r,9s,10s,13s,15s)-6-[(2r,5r)-5,6-dimethylheptan-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-yl acetate

C31H50O2 (454.3811)

(2s,3s,4s)-4-[(2e,4z,6r)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid

C15H21NO6 (311.1369)

(3as,4r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate

C10H17N7O5 (315.1291)

(1r,3r,6s,7s,8r,11r,12s,15r,16r)-15-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C33H56O2 (484.428)

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

C40H56 (536.4382)

(3r,11r,14s,23r,24s,31s,32s,33s,34r,35r)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-diene-29-carboxylic acid

C41H61NO9 (711.4346)

(2z,4e,6e,8e,10e,12e,14e,16e)-19-[(2r,4s)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-3-hydroxy-1-[(1r,4s)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

C40H56O5 (616.4128)

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

C29H48O2 (428.3654)

(2s,3s)-2-({[(3s,6s,9s,12s,15r)-3-[(acetyloxy)methyl]-2,5,11,14-tetrahydroxy-6-[2-(4-hydroxyphenyl)ethyl]-12-(2-methanesulfinylethyl)-7-methyl-8-oxo-9-(2-phenylethyl)-1,4,7,10,13-pentaazacyclononadeca-1,4,10,13-tetraen-15-yl]-c-hydroxycarbonimidoyl}amino)-3-methylpentanoic acid

C44H63N7O12S (913.4255)

(2r)-2-amino-3-{[(1r)-1-[(1r,3r,7r,10r,11r,14s,23r,24s,26r,31s,32s,33r,34r,35r)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]-2-hydroxyethyl]sulfanyl}propanoic acid

C45H70N2O10S (830.4751)

1-(5-isopropyl-6-methylhept-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

C30H50O (426.3861)

(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-2-en-1-ol

C40H56O2 (568.428)

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

C10H19AsO8 (342.0296)

(2,3,5,6,7,15-hexachloropentadec-14-en-4-yl)oxysulfonic acid

C15H24Cl6O4S (509.9526)

(3r,8ar)-1-hydroxy-3-isopropyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one

C10H16N2O2 (196.1212)

(5z)-5-[(2e,4e)-9-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)-7-methylnona-2,4,6,8-tetraen-1-ylidene]-3-(2-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}ethenyl)furan-2-one

C34H44O6 (548.3138)

14-methylpentadec-6-enoic acid

C16H30O2 (254.2246)

(2z,4e,6e,8e,10e,12e,14e,16e,18e)-19-[(3r,4s)-3,4-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3-hydroxy-1-[(1r,4s)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

C40H56O5 (616.4128)

(4r,6e,10e,12e,14e,16e,18e,20e,22e)-4-hydroxy-25-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-6,7,10,14,19,23-hexamethylpentacosa-6,10,12,14,16,18,20,22-octaen-24-yne-2,9-dione

C40H54O4 (598.4022)

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

C29H48O2 (428.3654)

6-[(9e,11e,13e,15e)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15-octaen-17-yn-1-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

C40H54O3 (582.4073)

(1r,5r,6r,9s,10s,13s,15s)-6-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C30H48O (424.3705)

(1r,5r,6r,9s,10s,13s,15s)-6-[(2r,5r)-5,6-dimethylheptan-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H48O (412.3705)

(1r)-4-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(1s)-6,6-dimethyl-2-methylidenecyclohex-3-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

C40H54O (550.4174)

(1r,4r,6s,10s)-4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecane

C15H24O (220.1827)

7-ethenyl-12-ethyl-21-hydroxy-6,11,27,28-tetramethyl-20-oxa-2,16,29,30-tetraazaheptacyclo[15.8.1.1³,²⁵.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²¹,²⁶]triaconta-1,3,5,7,9,11,13(29),14,17(26),18(28)-decaene-19,22-dione

C33H32N4O4 (548.2423)

6-(5-ethyl-6-methylhept-3-en-2-yl)-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C30H48O (424.3705)

(1r,5r,6r,9s,10s,13s,15r)-6-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H46O (410.3548)

(2e,5r,6r,9r,12r,13r,16r)-9-(4-carbamimidamidobutyl)-2-ethylidene-3,7,10,14-tetrahydroxy-12-[(1e,3z,5s,6r)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-19-oxo-1,4,8,11,15-pentaazacyclononadeca-3,7,10,14-tetraene-5,16-dicarboxylic acid

C42H62N8O10 (838.4589)

[(3as,4r,10as)-10,10-dihydroxy-2,6-diimino-hexahydro-1h-pyrrolo[1,2-c]purin-4-yl]methoxycarboximidic acid

C10H17N7O4 (299.1342)

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-isopropyl-6-methylhept-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

C30H50O (426.3861)

(1r,5r,6r,9s,10s,13s,15r)-6-[(2r,5r)-5,6-dimethylheptan-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H48O (412.3705)

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

C42H54O3 (606.4073)

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

C40H54O2 (566.4124)

(1r,2r,4s)-1-[(1e,3e,5e,7e,9e,11e,13e,15e)-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-octaen-17-yn-1-yl]-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-2-ol

C40H54O3 (582.4073)

15-(5-ethyl-6-methylheptan-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl benzoate

C38H58O2 (546.4437)

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

C30H50O (426.3861)

2-{2-[(5-{1-[5-(6-{5-[2-(hexadecanoyloxy)-3-hydroxy-4-methyloxan-2-yl]-3-hydroxyoxolan-2-yl}-2,4-dimethylhexa-3,5-dien-1-yl)-5-methyloxolan-2-yl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl}-2-methyl-4-oxooxolan-2-yl)(hydroxy)methyl]-1,6-dioxaspiro[4.5]decan-7-yl}propanoic acid

C63H102O16 (1114.7167)

[(1s,3r,5s,7r,9s,11s,12s,14r,15r,16s,18r,19s,22s,24r,27s,29r,31s,33r,35s,36r,38s,40r,42s,44r)-11,15-dihydroxy-14,19,22,24,36-pentamethyl-12-(sulfooxy)-36-[2-(sulfooxy)ethyl]-4,8,13,17,23,28,32,37,41,45-decaoxadecacyclo[22.21.0.0³,²².0⁵,¹⁸.0⁷,¹⁶.0⁹,¹⁴.0²⁷,⁴⁴.0²⁹,⁴².0³¹,⁴⁰.0³³,³⁸]pentatetracontan-35-yl]oxidanesulfonic acid

C42H66O24S3 (1050.3106)

2-[(2e,4e,6e,8e)-17-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14-heptaen-16-yn-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol

C40H54O3 (582.4073)

4-(18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3,7,12,16-tetramethyl-17-oxooctadeca-3,5,7,9,11,13,15-heptaen-1-yn-1-yl)-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C42H56O5 (640.4128)

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

C40H56O4 (600.4178)

(5z)-3-[(2r,6s,7ar)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-5-[(2e,4e,6e,8e)-11-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-2,9-dimethylundeca-2,4,6,8-tetraen-10-yn-1-ylidene]furan-2-one

C37H46O5 (570.3345)

(1r)-4-[(3e,5e,7e,9e,11e,13e,15e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-3,5,7,9,11,13,15-heptaen-1-yn-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C42H56O5 (640.4128)

(5s)-5-[(1r,4s,6r,7r,9s,10e,12s,17s,20r,29s,32r)-9,32-dihydroxy-6,10,13,20,32-pentamethyl-27-methylidene-33,34,35-trioxa-22-azahexacyclo[27.3.1.1¹,⁴.1⁴,⁷.0¹²,¹⁷.0¹⁷,²³]pentatriaconta-10,13,22-trien-14-yl]-3-methyloxolan-2-one

C42H63NO7 (693.4604)

5-[(4e,6e,8e)-11-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-2,9-dimethylundeca-2,4,6,8-tetraen-10-yn-1-ylidene]-3-(6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)furan-2-one

C37H46O5 (570.3345)

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

C30H52O2 (444.3967)

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

C10H21AsO9S (392.0122)

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-3-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

[C22H23O11]+ (463.124)

(5z)-3-[(1e)-2-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]-5-[(2e,4e,6e)-9-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-7-methylnona-2,4,6-trien-8-yn-1-ylidene]furan-2-one

C34H42O5 (530.3032)

2-(6-aminopurin-9-yl)-5-[(dimethylarsoryl)methyl]oxolane-3,4-diol

C12H18AsN5O4 (371.0575)

(4e,6e,8e,10e,12e,14e)-2-{2-[4-(acetyloxy)-2-hydroxy-2,6,6-trimethylcyclohexylidene]ethenyl}-17-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl hexanoate

C48H68O8 (772.4914)

hexahydroxy-[5,5'-bipyrimidine]-2,2'-dione

C8H6N4O8 (286.0186)

(2s)-2-amino-3-{[(1s)-1-[(1s,7s,10r,11s,14r,23s,24r,26r,31r,32s,33r,34r,35s)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]-2-hydroxyethyl]sulfanyl}propanoic acid

C45H70N2O10S (830.4751)

(8e,10e,12e,14e,16e,18e,20e,22e,24e)-6,6,10,14,19,23-hexamethyl-25-[(1r)-2,6,6-trimethylcyclohex-2-en-1-yl]pentacosa-8,10,12,14,16,18,20,22,24-nonaene-2,7-dione

C40H56O2 (568.428)

1-(5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C30H52O2 (444.3967)

1-[2,3-dimethyl-5-(2-oxopropyl)oxolan-2-yl]-18-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15,17-octaen-2-one

C40H56O5 (616.4128)

6-hydroxy-3-[(9e,11e,13e,15e)-18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-1,17-diyn-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

C40H48O4 (592.3552)

(1s,4s,9s,10s,13r)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane

C20H32 (272.2504)

1-(5-ethyl-6-methylheptan-2-yl)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C31H54O2 (458.4124)

2-[(26-{1-[3,14-dimethyl-12-oxo-5-(tetradecanoyloxy)-2,7,11-trioxatricyclo[8.4.0.0³,⁸]tetradec-13-en-6-yl]propan-2-yl}-8-hydroxy-7,20,30,32-tetramethyl-27-oxo-2,6,11,15,21,25,31-heptaoxaheptacyclo[18.13.0.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²²,³².0²⁴,³⁰]tritriacont-17-en-10-yl)methyl]prop-2-enoic acid

C64H96O17 (1136.6647)

6-(5-isopropyl-6-methylhept-6-en-2-yl)-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C31H50O (438.3861)

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

C31H54O2 (458.4124)

(2z,4e,6e,8e,10e,12e,14z,16e,18e)-19-[(3r,4s)-3,4-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3-hydroxy-1-[(1r,4s)-4-hydroxy-1,2,2-trimethylcyclopentyl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

C40H56O5 (616.4128)

15-(5-isopropylhept-5-en-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C33H54O2 (482.4124)

3-hydroxy-4-{11-[4-(2-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}ethenyl)-5-oxofuran-2-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate

C39H50O7 (630.3556)

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

C29H48O2 (428.3654)

(1r,3r,6s,7s,8r,11r,12s,15r,16r)-7,12,16-trimethyl-15-[(2r)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C32H52O2 (468.3967)

(1r)-4-[(3e,5e,7e,9e)-11-[(2z)-4-[(1e)-2-[(1r,2r,4s)-2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]ethenyl]-5-oxofuran-2-ylidene]-3,10-dimethylundeca-3,5,7,9-tetraen-1-yn-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C39H48O6 (612.3451)

6-hydroxy-3-[(9e,11e,13e,15e,17e)-18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

C40H52O4 (596.3865)

(1r,2s,5s,7s,8z,10e,12s,14r,16s,19s,20r,24r,27r,28r,29s,32s,33s,35r)-14-[(2r,3s,4s)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-5,7,9,19,29-pentamethyl-18,31-dioxo-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-35-carbaldehyde

C47H68O15 (872.4558)

(1s,5s,9r,12s,15s)-1,5,9,13,13-pentamethyltetracyclo[7.5.1.0⁴,¹⁵.0¹²,¹⁵]pentadec-3-ene

C20H32 (272.2504)

3-{4-[(2r,3r,6s)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile

C22H21N3O4 (391.1532)

(1r,3as,3br,5as,7s,9as,9bs,11as)-9a,11a-dimethyl-1-[(2s)-5-methylhex-3-en-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C28H46O2 (414.3498)

(2s)-2-amino-3-{[(2s)-2-[(1s,7s,10r,11s,14r,23s,24r,26r,31r,32s,33r,34r,35s)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]-2-hydroxyethyl]sulfanyl}propanoic acid

C45H70N2O10S (830.4751)

18-(3,4-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-1-[2,3-dimethyl-5-(2-oxopropyl)oxolan-2-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15,17-octaen-2-one

C40H56O5 (616.4128)

(8z,10e)-14-(2,3-dihydroxy-4-methyloxan-2-yl)-28-hydroxy-5,7,9,19,29-pentamethyl-18,31-dioxo-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-35-carboxylic acid

C47H68O16 (888.4507)

(2z,4e,6e,8e,10e)-19-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)-3-hydroxy-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

C40H56O5 (616.4128)

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

C28H44O2 (412.3341)

(1s,2r,5r,7r,8z,10e,12r,14s,16r,19r,20s,24s,27s,28s,29r,32r,33r,35s)-14-[(2s,3r,4r)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-35-(hydroxymethyl)-5,7,9,19,29-pentamethyl-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-18,31-dione

C47H70O15 (874.4714)

(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 (412.3705)

2-hydroxy-3-{5-hydroxy-8-[(3e)-4-[8'-hydroxy-6'-(1-hydroxy-3-{11-methyl-1,7-dioxaspiro[5.5]undecan-2-yl}butyl)-7'-methylidene-hexahydrospiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl}-2-methylpropanoic acid

C44H68O13 (804.466)

4-[(1r,3r,4r,5r,7s,10s,11s,14r,23s,24r,26s,31r,32r,33s,35r)-4,11-dihydroxy-5,11,23,24,35-pentamethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]-4-oxobutanoic acid

C45H67NO10 (781.4765)

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

C30H48O (424.3705)

(1r)-3,4,5,5-tetramethylcyclohex-3-en-1-ol

C10H18O (154.1358)

(1r,3z)-1-[(2s,5s,7r,8r)-2-[(2s)-2-hydroxyhept-6-en-1-yl]-8-methyl-1,6-dioxaspiro[4.5]decan-7-yl]hex-3-ene-1,6-diol

C22H38O5 (382.2719)

(1s,2r,4s)-2,6,6-trimethyl-1-[(1e,3e,5e,7e,9z,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohexane-1,2,4-triol

C40H60O6 (636.439)

(2s,6s,7ar)-2-[(2e,4e,6e,8e,10e,12e,14e,16e)-17-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-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

C40H56O3 (584.4229)

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

C30H52O (428.4018)

(s)-amino[(1s,7s,10r,11s,14r,23s,24r,26r,31r,32s,33r,34r,35s)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]acetic acid

C42H64N2O9 (740.4612)

(2r,6s,7ar)-2-[(2e,4e,6e,8e,10e,12e,14e)-17-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14-heptaen-16-yn-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol

C40H54O3 (582.4073)

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

C28H48O (400.3705)

(1r,2s,5s,8z,10e,12s,14r,16s,19r,20s,24s,27r,28r,29r,32r,33s,35s)-14-[(2r)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-35-(hydroxymethyl)-5,7,9,19,29-pentamethyl-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-18,31-dione

C47H70O15 (874.4714)

6-[(9e,11e,13e,15e,17e)-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-yl]-1,5,5-trimethyl-7-oxabicyclo[4.1.0]heptan-3-ol

C40H56O4 (600.4178)

4-ethyl-6-oxa-13-azatricyclo[8.2.1.0²,⁷]tridec-4-en-3-one

C13H19NO2 (221.1416)

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

C40H54O3 (582.4073)

(5z)-5-[(2e,4e,6e)-11-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)-2,9-dimethylundeca-2,4,6,8,10-pentaen-1-ylidene]-3-(6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)furan-2-one

C37H48O6 (588.3451)

(1s)-4-[(3e,5e,7e,9e,11e)-12-[(2r)-4-[(1e)-2-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]-5-oxo-2h-furan-2-yl]-3,10-dimethyldodeca-3,5,7,9,11-pentaen-1-yn-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C40H50O6 (626.3607)

α-echinenone/ phoenicopterone

C40H54O (550.4174)

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

C40H50O4 (594.3709)

3-hydroxy-4-(18-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-3-(hydroxymethyl)-7,12,16-trimethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene)-3,5,5-trimethylcyclohexyl acetate

C42H58O7 (674.4182)

(e)-2-epi-β-caryophyllene

C15H24 (204.1878)

9-(4-carbamimidamidobutyl)-2-ethylidene-3,7,10,14-tetrahydroxy-12-(6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl)-1,6,13-trimethyl-19-oxo-1,4,8,11,15-pentaazacyclononadeca-3,7,10,14-tetraene-5,16-dicarboxylic acid

C42H62N8O10 (838.4589)

amino({11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl})acetic acid

C42H64N2O9 (740.4612)

(2r,4s)-1-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(2r,4s)-2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-2-ol

C40H56O4 (600.4178)

(1r,5r,6r,9s,10s,13s,15r)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H46O (410.3548)

(2r)-2-[(2s,5r,7s)-2-[(s)-[(2r,5r)-5-[(1s,3r,5s)-1-[(2r,5r)-5-[(2r,3e,5e)-6-[(2r,3r,5s)-5-[(2r,3r,4r)-2-(hexadecanoyloxy)-3-hydroxy-4-methyloxan-2-yl]-3-hydroxyoxolan-2-yl]-2,4-dimethylhexa-3,5-dien-1-yl]-5-methyloxolan-2-yl]-5-methyl-2,8-dioxabicyclo[3.2.1]octan-3-yl]-2-methyl-4-oxooxolan-2-yl](hydroxy)methyl]-1,6-dioxaspiro[4.5]decan-7-yl]propanoic acid

C63H102O16 (1114.7167)

(2s,5s,6s)-5-(hydroxymethyl)-6-(4-hydroxyphenyl)-2-(1h-indol-3-yl)-5,6-dihydro-2h-1,4-oxazin-3-ol

C19H18N2O4 (338.1267)

17-methyloctadec-8-enoic acid

C19H36O2 (296.2715)

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

C10H19AsO8 (342.0296)

(1s,3r)-3-hydroxy-4-[(3e,5e,7e,9e)-11-[(2z)-4-[(1e)-2-[(1s)-1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl]ethenyl]-5-oxofuran-2-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetate

C39H48O7 (628.34)

4-hydroxy-4-[18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-yl]-3,3,5-trimethylcyclohexan-1-one

C40H54O4 (598.4022)

icos-7-enoic acid

C20H38O2 (310.2872)

(1r)-4-[(3e,5e,7e,9e)-11-[(2z)-4-[(2r,6s,7ar)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-5-oxofuran-2-ylidene]-3,10-dimethylundeca-3,5,7,9-tetraen-1-yn-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C39H48O6 (612.3451)

15-(5-isopropyl-6-methylhept-6-en-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C32H54O (454.4174)

(1s,3r)-4-[(3e,5e,7e,9e)-3,10-dimethyl-11-[(2z)-5-oxo-4-[(1e)-2-[(1s,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]ethenyl]furan-2-ylidene]undeca-1,3,5,7,9-pentaen-1-ylidene]-3-hydroxy-3,5,5-trimethylcyclohexyl acetate

C39H52O8 (648.3662)

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

C28H44O (396.3392)

6-hydroxy-3-[(3e,5e,7e,9e)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-1,17-diyn-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

C40H50O3 (578.376)

(1s,3s,7s,10r,11s,14s,23s,24r,26r,31r,32s,33s,34r,35s)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-diene-29-carboxylic acid

C41H61NO9 (711.4346)

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

C30H52O (428.4018)

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

C30H48O2 (440.3654)

(5z)-5-[(2e,4e,6e)-11-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)-2,9-dimethylundeca-2,4,6,8,10-pentaen-1-ylidene]-3-(2-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}ethenyl)furan-2-one

C37H48O6 (588.3451)

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

C28H46O (398.3548)

(1s,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-ethyl-6-methylhept-3-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 (412.3705)

(2r)-3-[(2s,5r,6r,8s)-8-[(2r,3e)-4-[(2r,4'ar,5r,6's,8'r)-6'-[(1s,3s)-3-[(3r,6r,11r)-3,11-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl]-1-hydroxybutyl]-8'-hydroxy-7'-methylidene-hexahydrospiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoic acid

C45H70O13 (818.4816)

(3r,8ar)-3-benzyl-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one

C14H16N2O2 (244.1212)

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

C28H44O (396.3392)

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

C40H54O2 (566.4124)

(2s,3as,7as)-n-(5-carbamimidamido-1-hydroxypentan-2-yl)-6-hydroxy-1-[(2s)-2-[(1-hydroxybutylidene)amino]-3-(4-hydroxyphenyl)propanoyl]-octahydroindole-2-carboximidic acid

C28H44N6O6 (560.3322)

3-hydroxy-4-(11-{4-[2-(1-hydroxy-2,6,6-trimethyl-4-oxocyclohex-2-en-1-yl)ethenyl]-5-oxofuran-2-ylidene}-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene)-3,5,5-trimethylcyclohexyl acetate

C39H48O7 (628.34)

4-{18-[2,3-dimethyl-5-(2-oxopropyl)oxolan-2-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-3,5,7,9,11,13,15-heptaen-1-yn-1-yl}-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C42H56O5 (640.4128)

[(2r,3s,4r,5s,6s,7r,14e)-2,3,5,6,7,15-hexachloropentadec-14-en-4-yl]oxysulfonic acid

C15H24Cl6O4S (509.9526)

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

C30H48O (424.3705)

4-[18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-1,17-diyn-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C42H54O3 (606.4073)

(1s,2r,5r,7r,8z,10e,12r,14s,16r,19r,20s,24r,27s,28s,29r,32r,33r,35s)-14-[(2s,3r,4r)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-5,7,9,19,29-pentamethyl-18,31-dioxo-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-35-carboxylic acid

C47H68O16 (888.4507)

4-[18-(3,4-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene]-3-hydroxy-3,5,5-trimethylcyclohexyl acetate

C42H58O5 (642.4284)

(1r,3r,6s,7s,8r,11r,12s,15r,16r)-15-[(2r,5r)-5-ethyl-6-methylheptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl benzoate

C38H58O2 (546.4437)

(1r,3as,3br,5as,7s,9as,9bs,11as)-9a,11a-dimethyl-1-[(2s,3e)-6-methylhept-3-en-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C29H48O2 (428.3654)

2-amino-3-[(1-{11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl}-2-hydroxyethyl)sulfanyl]propanoic acid

C45H70N2O10S (830.4751)

4-[(3e,5e,7e,9e,11e,13e,15e)-18-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15,17-octaen-1-yl]-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one

C40H54O5 (614.3971)

(1r,2r,7r,8r)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁸]undec-9-ene

C15H24 (204.1878)

[(3as,4r,9r)-5,10,10-trihydroxy-2,6-diimino-9-(sulfooxy)-hexahydropyrrolo[1,2-c]purin-4-yl]methoxycarboximidic acid

C10H17N7O9S (411.0808)

(4e,6e,8e,10e,12e,14e)-17-(1-hydroxy-2,2,6-trimethyl-4-oxocyclohexyl)-2-[2-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)ethynyl]-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl hexanoate

C46H64O6 (712.4703)

β-caryophyllene oxide

C15H24O (220.1827)

(4e,6e,8e,10e,12e,14e)-2-[2-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)ethenyl]-17-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl hexanoate

C46H66O7 (730.4808)

4-{11-[4-(6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-5-oxofuran-2-ylidene]-3,10-dimethylundeca-3,5,7,9-tetraen-1-yn-1-yl}-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C39H48O6 (612.3451)

1-[2,3-dimethyl-5-(2-oxopropyl)oxolan-2-yl]-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one

C40H54O4 (598.4022)

(2s,4s)-n-(5-carbamimidamido-1-hydroxypentan-2-yl)-1-[(2s)-2-[(1-hydroxyhexylidene)amino]-3-(4-hydroxyphenyl)propanoyl]-4-methylpyrrolidine-2-carboximidic acid

C27H44N6O5 (532.3373)

19'-hexanoyloxyfucoxanthin

C48H68O8 (772.4914)

6-(5,6-dimethylheptan-2-yl)-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H48O (412.3705)

[(3as,4r,10as)-5,10,10-trihydroxy-2,6-diimino-hexahydropyrrolo[1,2-c]purin-4-yl]methoxycarboximidic acid

C10H17N7O5 (315.1291)

(1s,2r)-4-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3r,4s)-3,4-dihydroxy-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-ene-1,2-diol

C40H56O4 (600.4178)

(1r,3r,6s,7s,8r,11r,12s,15r,16r)-15-[(2r,5z)-5-isopropylhept-5-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C33H54O2 (482.4124)

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

C40H56O6 (632.4077)

(2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methyl-n-(2-sulfoethyl)but-2-enimidic acid

C25H41ClN2O6S (532.2374)

3-[(22s,23s)-17-ethenyl-12-ethyl-13,18,22,27-tetramethyl-3,5-dioxo-4-oxa-8,24,25,26-tetraazahexacyclo[19.2.1.1⁶,⁹.1¹¹,¹⁴.1¹⁶,¹⁹.0²,⁷]heptacosa-1(24),2(7),6(27),8,10,12,14,16,18,20-decaen-23-yl]propanoic acid

C33H32N4O5 (564.2373)

(1r)-2,4,4-trimethyl-3-[(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-2-en-1-ol

C40H56O (552.4331)

5-[(4-hydroxyphenyl)methyl]-2-(1h-indol-3-yl)-5,6-dihydro-2h-1,4-oxazin-3-ol

C19H18N2O3 (322.1317)

3-hydroxy-4-{11-[4-(6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl)-5-oxofuran-2-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate

C39H50O7 (630.3556)

(5z)-5-[(2e,4e,6e,8e)-11-[(2r,4s)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-2,9-dimethylundeca-2,4,6,8,10-pentaen-1-ylidene]-3-[(1e)-2-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]furan-2-one

C37H48O6 (588.3451)

(1s,3r,6s,7s,8r,11r,12s,15r,16r)-7,12,16-trimethyl-15-[(2r)-6-methyl-5-methylideneheptan-2-yl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C30H50O (426.3861)

[(3as,4r,9r,10as)-10,10-dihydroxy-2,6-diimino-9-(sulfooxy)-hexahydro-1h-pyrrolo[1,2-c]purin-4-yl]methoxycarboximidic acid

C10H17N7O8S (395.0859)

(1r,3as,3br,5as,7s,9as,9bs,11as)-9a,11a-dimethyl-1-[(2s,3e)-5-methylhex-3-en-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C28H46O2 (414.3498)

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

C30H50O (426.3861)

(1s,2r,5r,7r,8z,10e,12r,14s,16r,19r,20s,24r,27s,28s,29r,32r,33r,35s)-14-[(2s,3r,4r)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-5,7,9,19,29,35-hexamethyl-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-18,31-dione

C47H70O14 (858.4765)

(3r,7r,8ar)-3-benzyl-1,7-dihydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one

C14H16N2O3 (260.1161)

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

C10H21AsO10S (408.0071)

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

C28H46O (398.3548)

(2r,5s,6s)-5-(hydroxymethyl)-6-(4-hydroxyphenyl)-2-(1h-indol-3-yl)-5,6-dihydro-2h-1,4-oxazin-3-ol

C19H18N2O4 (338.1267)

14-(2,3-dihydroxy-4-methyloxan-2-yl)-28-hydroxy-35-(hydroxymethyl)-5,7,9,19,29-pentamethyl-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-18,31-dione

C47H70O15 (874.4714)

(1s,3as,3bs,7s,9ar,9br,11as)-9a,11a-dimethyl-1-[(2s,3e)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C29H46O2 (426.3498)

4-hydroxy-4-[(3e,5e,7e,9e)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one

C40H52O4 (596.3865)

(2s)-2-{[(2s)-2-({2-[(2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-4-methylpentanoic acid

C28H37N5O7 (555.2693)

(4s,6e,10e,12e,14e,16e,18e,20e,22e)-4-hydroxy-25-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-6,7,10,14,19,23-hexamethylpentacosa-6,10,12,14,16,18,20,22-octaen-24-yne-2,9-dione

C40H54O4 (598.4022)

(1r,3r,6s,7s,8r,11r,12s,15r,16r)-15-[(2r,5r)-5-isopropyl-6-methylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C34H56O2 (496.428)

(2r,5s,6s)-5-(hydroxymethyl)-2-(1h-indol-3-yl)-6-(4-propoxyphenyl)-5,6-dihydro-2h-1,4-oxazin-3-ol

C22H24N2O4 (380.1736)

(2r)-2-{[(2r)-2-({2-[(2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-4-(methylsulfanyl)butanoic acid

C27H35N5O7S (573.2257)

(1r,5r,6r,9s,10s,13s,15s)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-yl acetate

C31H48O2 (452.3654)

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

C40H52O2 (564.3967)

(2z,4e,6e,8e,10e)-3-hydroxy-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-19-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

C40H56O5 (616.4128)

(1r)-4-[(3e,5e,7e,9e,11e,13e,15e)-18-[(2s,3r,5r)-2,3-dimethyl-5-(2-oxopropyl)oxolan-2-yl]-3,7,12,16-tetramethyl-17-oxooctadeca-3,5,7,9,11,13,15-heptaen-1-yn-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C42H56O5 (640.4128)

(1r,4z,9r)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

C15H24 (204.1878)

2-{[(1r,3s,5r,7s,8s,10r,12r,14s,16r,17z,20s,22r,24s,26r,30r,32s)-26-[(2r)-1-[(1r,3s,5r,6s,8r,10s)-5-(hexadecanoyloxy)-3,14-dimethyl-12-oxo-2,7,11-trioxatricyclo[8.4.0.0³,⁸]tetradec-13-en-6-yl]propan-2-yl]-8-hydroxy-7,20,30,32-tetramethyl-27-oxo-2,6,11,15,21,25,31-heptaoxaheptacyclo[18.13.0.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²²,³².0²⁴,³⁰]tritriacont-17-en-10-yl]methyl}prop-2-enoic acid

C66H100O17 (1164.696)

(5z)-3-[(2r,6s,7ar)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-5-[(2e,4e,6e,8e)-11-[(2r,4s)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-2,9-dimethylundeca-2,4,6,8,10-pentaen-1-ylidene]furan-2-one

C37H48O6 (588.3451)

3-hydroxy-4-{9-[4-(2-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}ethenyl)-5-oxofuran-2-ylidene]-3-methylnona-1,3,5,7-tetraen-1-ylidene}-3,5,5-trimethylcyclohexyl acetate

C36H46O7 (590.3243)

2,4,4-trimethyl-3-[(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-2-en-1-ol

C40H56O (552.4331)

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

C40H56O5 (616.4128)

(3s)-3-(2,4-dihydroxyphenyl)-5-hydroxy-8,8-dimethyl-2h,3h-pyrano[2,3-f]chromen-4-one

C20H18O6 (354.1103)

3-{4-[(2s,3s,6r)-5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile

C22H21N3O4 (391.1532)

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

C30H48O2 (440.3654)

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

C40H54O3 (582.4073)

4-(3,10-dimethyl-11-{5-oxo-4-[2-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)ethenyl]furan-2-ylidene}undeca-1,3,5,7,9-pentaen-1-ylidene)-3-hydroxy-3,5,5-trimethylcyclohexyl acetate

C39H52O8 (648.3662)

6-(5,6-dimethylhept-3-en-2-yl)-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-yl acetate

C31H48O2 (452.3654)

[({[(2s,3r,4s,5s)-5-[(dimethylarsoryl)methyl]-3,4-dihydroxyoxolan-2-yl]oxy}(hydroxy)methylidene)amino]acetic acid

C10H18AsNO8 (355.0248)

(1s,2r)-4-[(1e,3e,5e,7e,9e,11e,13e,15e)-18-[(2r,4s)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-ene-1,2-diol

C40H56O4 (600.4178)

(6r)-6-hydroxy-3-[(3e,5e,7e,9e,11e,13e,15e)-18-[(4r)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-1,17-diyn-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

C40H48O4 (592.3552)

(1s,3as,3bs,7s,9ar,9br,11as)-9a,11a-dimethyl-1-[(2s,3e)-5-methylhex-3-en-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C28H44O2 (412.3341)

(2s,3as,7as)-n-(5-carbamimidamido-1-hydroxypentan-2-yl)-6-hydroxy-1-[(2s)-2-[(1-hydroxyethylidene)amino]-3-(4-hydroxyphenyl)propanoyl]-octahydroindole-2-carboximidic acid

C26H40N6O6 (532.3009)

(2r,3r,4s,5s)-2-[(2r)-2,3-dihydroxypropoxy]-5-[(dimethylarsoryl)methyl]oxolane-3,4-diol

C10H21AsO7 (328.0503)

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

C10H21AsO9S (392.0122)

(7r,8r,9s)-2,6,6,9-tetramethyltricyclo[5.4.0.0²,⁹]undecan-8-yl acetate

C17H28O2 (264.2089)

6-hydroxy-3-[(13e,15e,17e)-18-(4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)-3,7,11,15-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

C40H52O4 (596.3865)

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

C10H21AsO9S (392.0122)

2,6,6-trimethyl-1-[(9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohexane-1,2,4-triol

C40H60O6 (636.439)

(1s,3as,3bs,7s,9ar,9br,11as)-9a,11a-dimethyl-1-[(2s)-6-methylhept-3-en-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C29H46O2 (426.3498)

3-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2r,3s,4s,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1λ⁴-chromen-1-ylium

[C26H29O16]+ (597.1456)

(1s,2r,7r,10r)-4-ethyl-6-oxa-13-azatricyclo[8.2.1.0²,⁷]tridec-4-en-3-one

C13H19NO2 (221.1416)

ossipurinolo

C5H4N4O2 (152.0334)

4-hydroxy-25-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-6,7,10,14,19,23-hexamethylpentacosa-6,10,12,14,16,18,20,22-octaen-24-yne-2,9-dione

C40H54O4 (598.4022)

(1r,2s,5s,7s,8e,10z,12s,14r,16s,19s,20r,27r,28r,29s,32s,33s,35r)-14-[(2r,3s,4s)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-5,7,9,19,29-pentamethyl-18,31-dioxo-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-35-carbaldehyde

C47H68O15 (872.4558)

(1s,2r,5r,7r,8z,10e,12r,14s,16r,19r,20s,24s,27s,28s,29r,32r,33r,35s)-14-[(2s,3r,4r)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-5,7,9,19,29-pentamethyl-18,31-dioxo-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-35-carboxylic acid

C47H68O16 (888.4507)

(1r,2r,4s)-1-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(1r,2r,4s)-2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-2-ol

C40H56O4 (600.4178)

(3r,8ar)-1-hydroxy-3-(2-methylpropyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one

C11H18N2O2 (210.1368)

(5z)-3-(2-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}ethenyl)-5-[(2e,4e)-9-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-7-methylnona-2,4,6-trien-8-yn-1-ylidene]furan-2-one

C34H42O5 (530.3032)

(2s,7s)-3,3,7-trimethyl-8-methylidenetricyclo[5.4.0.0²,⁹]undecane

C15H24 (204.1878)

(2s)-2-{[(2s)-2-({2-[(2-{[(2s)-2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-4-(methylsulfanyl)butanoic acid

C27H35N5O7S (573.2257)

(3e,5e,7e,9e,11e,13e,15e,17e)-1-[(2s,3r,5r)-2,3-dimethyl-5-(2-oxopropyl)oxolan-2-yl]-18-[(1r,2r,4s)-2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15,17-octaen-2-one

C40H56O5 (616.4128)

4-{11-[4-(2-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}ethenyl)-5-oxofuran-2-ylidene]-3,10-dimethylundeca-3,5,7,9-tetraen-1-yn-1-yl}-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C39H48O6 (612.3451)

7,12,16-trimethyl-15-(6-methyl-5-methylideneheptan-2-yl)pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C32H52O2 (468.3967)

(3s,4s)-4-ethenyl-1-isopropyl-4-methyl-3-(prop-1-en-2-yl)cyclohex-1-ene

C15H24 (204.1878)

15-(5-ethyl-6-methylhept-3-en-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C31H52O (440.4018)

(5z)-5-[(2e,4e,6e)-11-(3,4-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-2,9-dimethylundeca-2,4,6,8,10-pentaen-1-ylidene]-3-(2-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}ethenyl)furan-2-one

C37H48O6 (588.3451)

(2r)-2-amino-3-{[(1s)-1-[(1r,3r,7r,10r,11r,14s,23r,24s,26r,31s,32s,33r,34r,35r)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]-2-hydroxyethyl]sulfanyl}propanoic acid

C45H70N2O10S (830.4751)

(4s)-4-[(3e,5e,7e,9e,11e,13e,15e)-18-[(2r,4s)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15,17-octaen-1-yl]-4-hydroxy-3,5,5-trimethylcyclohex-2-en-1-one

C40H54O5 (614.3971)

(8e,10e,12z,14e,16e,18e,20e,22e,24e)-6,6,10,14,19,23,27,27-octamethyldotriaconta-8,10,12,14,16,18,20,22,24-nonaene-2,7,26,31-tetrone

C40H56O4 (600.4178)

(2s,5s)-5-[(4-hydroxyphenyl)methyl]-2-(1h-indol-3-yl)-5,6-dihydro-2h-1,4-oxazin-3-ol

C19H18N2O3 (322.1317)

[(3ar,9r,10as)-10,10-dihydroxy-2,6-diimino-9-(sulfooxy)-hexahydro-1h-pyrrolo[1,2-c]purin-4-yl]methoxycarboximidic acid

C10H17N7O8S (395.0859)

15-(5-isopropyl-6-methylhept-6-en-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C34H56O2 (496.428)

11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-diene-29-carboxylic acid

C41H61NO9 (711.4346)

(4as,4br,7s,8ar)-7-ethenyl-1,1,4b,7-tetramethyl-3,4,4a,5,6,8,8a,9-octahydro-2h-phenanthrene

C20H32 (272.2504)

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

C40H54O2 (566.4124)

3-[(21s,22s)-16-ethenyl-11-ethyl-4-hydroxy-12,17,21,26-tetramethyl-7,23,24,25-tetraazahexacyclo[18.2.1.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²,⁶]hexacosa-1,4,6,8(26),9,11,13(25),14,16,18(24),19-undecaen-22-yl]propanoic acid

C33H34N4O3 (534.2631)

4-{11-[4-(2-{2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl}ethenyl)-5-oxofuran-2-ylidene]-3,10-dimethylundeca-3,5,7,9-tetraen-1-yn-1-yl}-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C39H48O6 (612.3451)

1-(5-isopropyl-6-methylhepta-3,6-dien-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C30H48O (424.3705)

(1r,3r,6s,7s,8r,11r,12s,15r,16r)-15-[(2r,5r)-5,6-dimethylheptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C32H54O2 (470.4124)

[(1r,3s,5r,7s,9r,11s,13r,14s,16r,18s,20r,22s,25r,27s,30r,31r,33s,34r,35r,37s,40s,42r,44s,46r,48s)-34-hydroxy-40-[(2r,3e)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulfooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0³,²⁵.0⁵,²².0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³¹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]nonatetracontan-14-yl]oxidanesulfonic acid

C55H82O21S2 (1142.479)

4-[(1r,3r,4r,5r,7r,10s,11s,14r,23s,24r,26s,31r,32r,33s,35r)-4,11-dihydroxy-5,11,23,24,35-pentamethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]-4-oxobutanoic acid

C45H67NO10 (781.4765)

n-[(2s,3r,4s)-4-(hexadeca-6,9,12-trienoyloxy)-5-(hexadecanoyloxy)-1,3-dihydroxypentan-2-yl]dodecanimidic acid

C49H89NO7 (803.6639)

(5z)-5-[(2e,4e,6e,8e,10e)-11-[(3r,4s)-3,4-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-2,9-dimethylundeca-2,4,6,8,10-pentaen-1-ylidene]-3-[(1e)-2-[(1r,2r,4s)-2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]ethenyl]furan-2-one

C37H48O6 (588.3451)

(6s)-6-hydroxy-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-18-[(4s)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl]-4,8,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

C40H52O4 (596.3865)

(1r,2s,5s,7s,8e,10z,12s,14r,16s,19s,20r,24r,27s,28s,29s,32s,33s,35r)-14-[(2r,3s,4s)-2,3-dihydroxy-4-methyloxan-2-yl]-27-hydroxy-35-(hydroxymethyl)-5,7,9,19,29-pentamethyl-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁸.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-18,31-dione

C47H70O15 (874.4714)

{[({5-[(dimethylarsoryl)methyl]-3,4-dihydroxyoxolan-2-yl}oxy)(hydroxy)methylidene]amino}acetic acid

C10H18AsNO8 (355.0248)

(2r,3r,4s,5s)-2-(6-aminopurin-9-yl)-5-[(dimethylarsoryl)methyl]oxolane-3,4-diol

C12H18AsN5O4 (371.0575)

(1s,2s)-4-[(3e,5e,7e,9e,11e,13e,15e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-1,17-diyn-1-yl]-3,5,5-trimethylcyclohex-3-ene-1,2-diol

C40H52O3 (580.3916)

(1r,3as,3br,9as,9bs,11as)-9a,11a-dimethyl-1-(6-methylhepta-2,4,6-trien-2-yl)-tetradecahydro-1h-cyclopenta[a]phenanthrene

C27H42 (366.3286)

4-{12-[4-(2-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}ethenyl)-5-oxo-2h-furan-2-yl]-3,10-dimethyldodeca-3,5,7,9,11-pentaen-1-yn-1-yl}-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C40H50O6 (626.3607)

(5z)-5-[(2e,4e,6e)-9-[(2r,4s)-2,4-dihydroxy-2,6,6-trimethylcyclohexylidene]-7-methylnona-2,4,6,8-tetraen-1-ylidene]-3-[(1e)-2-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]furan-2-one

C34H44O6 (548.3138)

3-{4-[5-hydroxy-3-(hydroxymethyl)-6-(1h-indol-3-yl)-3,6-dihydro-2h-1,4-oxazin-2-yl]phenoxy}propanenitrile

C22H21N3O4 (391.1532)

(5z)-3-[(1e)-2-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]-5-[(2e,4e,6e,8e)-11-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-2,9-dimethylundeca-2,4,6,8-tetraen-10-yn-1-ylidene]furan-2-one

C37H46O5 (570.3345)

(r)-amino[(1r,3r,7r,10r,11r,14s,23r,24s,26r,31s,32s,33r,34r,35r)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]acetic acid

C42H64N2O9 (740.4612)

4-{4,11-dihydroxy-5,11,23,24,35-pentamethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl}-4-oxobutanoic acid

C45H67NO10 (781.4765)

5-(hydroxymethyl)-6-(4-hydroxyphenyl)-2-(1h-indol-3-yl)-5,6-dihydro-2h-1,4-oxazin-3-ol

C19H18N2O4 (338.1267)

(2z,5r,6s,9s,12s,13s,16r)-9-(4-carbamimidamidobutyl)-2-ethylidene-3,7,10,14-tetrahydroxy-12-[(1e,3e,5s,6s)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,6,13-trimethyl-19-oxo-1,4,8,11,15-pentaazacyclononadeca-3,7,10,14-tetraene-5,16-dicarboxylic acid

C42H62N8O10 (838.4589)

3-{8-[(3e)-4-[6'-(3-{3,11-dimethyl-1,7-dioxaspiro[5.5]undecan-2-yl}-1-hydroxybutyl)-8'-hydroxy-7'-methylidene-hexahydrospiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl}-2-hydroxy-2-methylpropanoic acid

C45H70O13 (818.4816)

(1s,3r)-4-[(3e,5e,7e,9e)-11-[(2z)-4-[(2r,6s,7ar)-6-hydroxy-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-2-yl]-5-oxofuran-2-ylidene]-3,10-dimethylundeca-1,3,5,7,9-pentaen-1-ylidene]-3-hydroxy-3,5,5-trimethylcyclohexyl acetate

C39H50O7 (630.3556)

(1as,4ar,7as,7br)-1,1,7-trimethyl-4-methylidene-octahydro-1ah-cyclopropa[e]azulene

C15H24 (204.1878)

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

C40H54O (550.4174)

2-(2,3-dihydroxypropoxy)-5-[(dimethylarsoryl)methyl]oxolane-3,4-diol

C10H21AsO7 (328.0503)

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

C28H46O (398.3548)

methyl 3-[(22s,23s)-17-ethenyl-12-ethyl-13,18,22,27-tetramethyl-3,5-dioxo-4-oxa-8,24,25,26-tetraazahexacyclo[19.2.1.1⁶,⁹.1¹¹,¹⁴.1¹⁶,¹⁹.0²,⁷]heptacosa-1,6,9(27),10,12,14(26),15,17,19(25),20-decaen-23-yl]propanoate

C34H34N4O5 (578.2529)

9a,11a-dimethyl-1-(5-methylhexan-2-yl)-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C28H48O2 (416.3654)

[(3as,4r,9s,10as)-10,10-dihydroxy-2,6-diimino-9-(sulfooxy)-hexahydro-1h-pyrrolo[1,2-c]purin-4-yl]methoxycarboximidic acid

C10H17N7O8S (395.0859)

(4e)-5-[(2r,3as,5r,5'r,6s,6''s,7as)-2-[(s)-hydroxy[(2r,3r,5s,6s)-2-hydroxy-3,5-dimethyl-6-{3-[(1'r,2r,2's,3r,5s,6's,8's,10'r)-3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecan]-8'-yl]prop-1-en-2-yl}oxan-2-yl]methyl]-6-methyl-2,3,3a,5'',6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl]pent-4-enoic acid

C47H71NO12 (841.4976)

(1s,2s,4s)-2,6,6-trimethyl-1-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1s,2s,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohexane-1,2,4-triol

C40H60O6 (636.439)

3-[(22s,23s)-17-ethenyl-12-ethyl-13,18,22,27-tetramethyl-3,5-dioxo-4-oxa-8,24,25,26-tetraazahexacyclo[19.2.1.1⁶,⁹.1¹¹,¹⁴.1¹⁶,¹⁹.0²,⁷]heptacosa-1,6,9(27),10,12,14(26),15,17,19(25),20-decaen-23-yl]propanoic acid

C33H32N4O5 (564.2373)

2,2,4-trimethyl-3-[(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-one

C40H54O (550.4174)

(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3r,4s)-3,4-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-1-[(2s,3r,5r)-2,3-dimethyl-5-(2-oxopropyl)oxolan-2-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15,17-octaen-2-one

C40H56O5 (616.4128)

n-[(2s,3r,4s)-4-[(6z,9z,12z)-hexadeca-6,9,12-trienoyloxy]-5-(hexadecanoyloxy)-1,3-dihydroxypentan-2-yl]dodecanimidic acid

C49H89NO7 (803.6639)

(1r,2r,7r,10s)-4-ethyl-6-oxa-13-azatricyclo[8.2.1.0²,⁷]tridec-4-en-3-one

C13H19NO2 (221.1416)

(20r,24s,26s)-7-ethenyl-12-ethyl-19,20-dihydroxy-6,11,26,27-tetramethyl-2,16,28,29-tetraazaheptacyclo[15.7.1.1³,²⁴.1⁵,⁸.1¹⁰,¹³.1¹⁵,¹⁸.0²⁰,²⁵]nonacosa-1(25),3,5(29),6,8,10(28),11,13,15(27),16,18-undecaen-21-one

C33H32N4O3 (532.2474)

2-amino-3-({1-[(1r,3r,7r,10r,11r,14s,23r,24s,26r,31s,32s,33r,34r,35r)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]-2-hydroxyethyl}sulfanyl)propanoic acid

C45H70N2O10S (830.4751)

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

C10H19AsO8 (342.0296)

stigmast-5-en-3-ol, (3β)-

C29H50O (414.3861)

2-{[(1r,3s,5r,7s,8s,10r,12r,14s,16r,17z,20s,22r,24s,26r,30r,32s)-26-[(2r)-1-[(1r,3s,5r,6s,8r,10s)-3,14-dimethyl-12-oxo-5-(tetradecanoyloxy)-2,7,11-trioxatricyclo[8.4.0.0³,⁸]tetradec-13-en-6-yl]propan-2-yl]-8-hydroxy-7,20,30,32-tetramethyl-27-oxo-2,6,11,15,21,25,31-heptaoxaheptacyclo[18.13.0.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²²,³².0²⁴,³⁰]tritriacont-17-en-10-yl]methyl}prop-2-enoic acid

C64H96O17 (1136.6647)

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

C40H56O5 (616.4128)

14-(2,3-dihydroxy-4-methyloxan-2-yl)-28-hydroxy-5,7,9,19,29-pentamethyl-18,31-dioxo-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-35-carbaldehyde

C47H68O15 (872.4558)

(1r,3s)-6-[(3e,5e,7e,9e,11e,13e,15e)-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-octaen-17-yn-1-ylidene]-1,5,5-trimethylcyclohexane-1,3-diol

C40H54O3 (582.4073)

5-(2-{hydroxy[2-hydroxy-3,5-dimethyl-6-(3-{3,5,10'-trimethyl-3',7',12'-trioxaspiro[piperidine-2,4'-tricyclo[6.3.1.0²,⁶]dodecan]-8'-yl}prop-1-en-2-yl)oxan-2-yl]methyl}-6-methyl-2,3,3a,5'',6,6'',7,7a-octahydrodispiro[furo[3,2-b]pyran-5,2'-oxolane-5',2''-pyran]-6''-yl)pent-4-enoic acid

C47H71NO12 (841.4976)

(5z)-5-[(2e,4e,6e)-9-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-7-methylnona-2,4,6-trien-8-yn-1-ylidene]-3-[(1e)-2-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]ethenyl]furan-2-one

C34H44O6 (548.3138)

n-[(2s,3r,4s)-1,3-dihydroxy-5-(tetradecanoyloxy)-4-(undeca-4,7-dienoyloxy)pentan-2-yl]dodecanimidic acid

C42H77NO7 (707.57)

15-(5-ethyl-6-methylheptan-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C33H56O2 (484.428)

(4z)-4-[(3e,5e,7e,9e,11e,13e,15e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-ylidene]-3,5,5-trimethylcyclohex-2-en-1-one

C40H50O3 (578.376)

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

C40H54O (550.4174)

15-(5,6-dimethylheptan-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C32H54O2 (470.4124)

(s)-amino[(1r,3r,7r,10r,11r,14s,23r,24s,26r,31s,32s,33r,34r,35r)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]acetic acid

C42H64N2O9 (740.4612)

(1r,5r,6r,9s,10s,13s,15s)-6-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H46O (410.3548)

(2e,6e,8e)-33-amino-4,10,12,19,22-pentahydroxy-2,6,9,19,31,32-hexamethyl-5,24,29-trimethylidene-15,18,28-trioxotritriaconta-2,6,8-trienoic acid

C42H67NO10 (745.4765)

(1s,2r,5r,7r,8z,10e,12r,14s,16r,19r,20s,24r,27s,28s,29r,32r,33r,35s)-14-[(2s,3r,4r)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-35-(hydroxymethyl)-5,7,9,19,29-pentamethyl-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-18,31-dione

C47H70O15 (874.4714)

24-α-methylcholesterol

C28H48O (400.3705)

(3r,8ar)-3-[(2r)-butan-2-yl]-1-hydroxy-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one

C11H18N2O2 (210.1368)

1-[7-(5-hydroxypent-2-en-1-yl)-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]dec-9-ene-3,5-diol

C22H38O5 (382.2719)

(4r,5r)-4-hydroxy-4-[(3e,5e,7e,9e,11e,13e,15e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-yl]-3,3,5-trimethylcyclohexan-1-one

C40H54O4 (598.4022)

(1s,3r,6s,7s,8r,11r,12s,15r,16r)-15-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C31H52O (440.4018)

(1s,3r,6s,7s,8r,11r,12s,15r,16r)-15-[(2r,5r)-5-isopropyl-6-methylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C32H54O (454.4174)

(1r)-4-[(3e,5e,7e,9e)-11-[(2z)-4-[(1e)-2-[(1r,2r)-2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]ethenyl]-5-oxofuran-2-ylidene]-3,10-dimethylundeca-3,5,7,9-tetraen-1-yn-1-yl]-3,5,5-trimethylcyclohex-3-en-1-yl acetate

C39H48O6 (612.3451)

(4e,6e,8e,10e,12e,14e)-17-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-2,6,11,15-tetramethylheptadeca-2,4,6,8,10,12,14-heptaen-16-ynal

C30H38O2 (430.2872)

2-[(26-{1-[5-(hexadecanoyloxy)-3,14-dimethyl-12-oxo-2,7,11-trioxatricyclo[8.4.0.0³,⁸]tetradec-13-en-6-yl]propan-2-yl}-8-hydroxy-7,20,30,32-tetramethyl-27-oxo-2,6,11,15,21,25,31-heptaoxaheptacyclo[18.13.0.0³,¹⁶.0⁵,¹⁴.0⁷,¹².0²²,³².0²⁴,³⁰]tritriacont-17-en-10-yl)methyl]prop-2-enoic acid

C66H100O17 (1164.696)

(2e)-4-[(1r,5s,7r)-1-[(2s,3e,5r,6z)-7-chloro-5,9-dihydroxynona-3,6-dien-2-yl]-6-azaspiro[4.5]decan-7-yl]-2-methylbut-2-enoic acid

C23H36ClNO4 (425.2333)

(3s,5s)-1-[(1r,2r,5r,7r)-7-[(2z)-5-hydroxypent-2-en-1-yl]-2-methyl-6,8-dioxabicyclo[3.2.1]octan-5-yl]dec-9-ene-3,5-diol

C22H38O5 (382.2719)

1-[2-(2-hydroxyhept-6-en-1-yl)-8-methyl-1,6-dioxaspiro[4.5]decan-7-yl]hex-3-ene-1,6-diol

C22H38O5 (382.2719)

2-{[2-({2-[(2-{[2-amino-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxy-3-phenylpropylidene]amino}-4-methylpentanoic acid

C28H37N5O7 (555.2693)

2-amino-3-[(2-{11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl}-2-hydroxyethyl)sulfanyl]propanoic acid

C45H70N2O10S (830.4751)

4-(dimethylarsoryl)-n-(2-sulfoethyl)butanimidic acid

C8H18AsNO5S (315.0122)

3-(2-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}ethenyl)-5-[(4e,6e,8e)-11-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-2,9-dimethylundeca-2,4,6,8-tetraen-10-yn-1-ylidene]furan-2-one

C37H46O5 (570.3345)

(1s,3ar,3br,7r,9as,9br,11ar)-9a,11a-dimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C30H48O2 (440.3654)

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

C40H52O2 (564.3967)

1,1,7-trimethyl-4-methylidene-octahydro-1ah-cyclopropa[e]azulene

C15H24 (204.1878)

(2s,6r,7as)-2-[(2e,4e,6e,8e,10e,12e,14e)-17-[(4s)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-6,11,15-trimethylheptadeca-2,4,6,8,10,12,14-heptaen-16-yn-2-yl]-4,4,7a-trimethyl-2,5,6,7-tetrahydro-1-benzofuran-6-ol

C40H54O3 (582.4073)

(1s,3r)-3-hydroxy-4-[(3e,5e,7e)-9-[(2z)-4-[(1e)-2-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]ethenyl]-5-oxofuran-2-ylidene]-3-methylnona-1,3,5,7-tetraen-1-ylidene]-3,5,5-trimethylcyclohexyl acetate

C36H46O7 (590.3243)

(1r,5r,6r,9s,10s,13s,15s)-6-[(2r,5s)-5,6-dimethylheptan-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H48O (412.3705)

[(1r,3s,5r,7s,9r,11s,13r,14s,16r,18s,20r,22s,25r,27s,30s,31r,33s,34r,35r,37s,40s,42r,44s,46r,48s)-34-hydroxy-40-[(2r,3e)-2-hydroxy-5-methylideneocta-3,7-dien-2-yl]-13,25,27,30,35-pentamethyl-39-methylidene-13-[3-(sulfooxy)propyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0³,²⁵.0⁵,²².0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³¹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]nonatetracontan-14-yl]oxidanesulfonic acid

C56H84O21S2 (1156.4946)

6-(5,6-dimethylhept-3-en-2-yl)-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H46O (410.3548)

(1s,3as,3bs,7s,9ar,9br,11as)-1-[(2s,3e,5s)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C30H48O2 (440.3654)

(3e,5e,7e,9e,11e,13e,15e)-1-[(2s,3r,5r)-2,3-dimethyl-5-(2-oxopropyl)oxolan-2-yl]-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one

C40H54O4 (598.4022)

(1s,2r,5r,7r,8z,10e,12s,14r,16r,19r,20s,24s,27s,28s,29r,33r,35r)-14-[(2r,3r)-2,3-dihydroxy-4-methyloxan-2-yl]-27-hydroxy-5,7,9,19,29-pentamethyl-18,31-dioxo-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁸.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-35-carboxylic acid

C47H68O16 (888.4507)

(1r,3ar,3bs,5as,7s,9as,9bs,11as)-9a,11a-dimethyl-1-[(2s,3e,5s)-5-methylhept-3-en-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C29H48O2 (428.3654)

4-[(3e,5e,7e,9e)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyl-2-oxooctadeca-3,5,7,9,11,13,15-heptaen-17-yn-1-ylidene]-3,5,5-trimethylcyclohex-2-en-1-one

C40H50O3 (578.376)

3-{[(2s,3s,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5s)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

[C26H29O15]+ (581.1506)

(2z,4e,6e,8e,10e)-19-(3,4-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3-hydroxy-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

C40H56O5 (616.4128)

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

C10H21AsO10S (408.0071)

(1r,2r,4s)-1-[(1e,3e,5e,7e,9e,11e,13e,15z,17e)-18-[(1r,2r,4s)-2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-2-ol

C40H56O4 (600.4178)

(2z,4e,6e,8e,10e,12e,14e)-17-[(1r,6r)-1-hydroxy-2,2,6-trimethyl-4-oxocyclohexyl]-2-{2-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]ethynyl}-6,11,15-trimethyl-16-oxoheptadeca-2,4,6,8,10,12,14-heptaen-1-yl hexanoate

C46H64O6 (712.4703)

6-(5,6-dimethylheptan-2-yl)-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-yl acetate

C31H50O2 (454.3811)

(1s,2r,4s)-1-[(1e,3e,5e,7e,9e,11e,13e,15e)-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-octaen-17-yn-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol

C40H56O4 (600.4178)

(1r,5r,6r,9s,10s,13s,15r)-6-[(2r,5s)-5,6-dimethylheptan-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H48O (412.3705)

(5-methoxy-5-oxopentyl)trimethylazanium

[C9H20NO2]+ (174.1494)

(1ar,4as,7r,7ar,7bs)-1,1,7-trimethyl-4-methylidene-octahydro-1ah-cyclopropa[e]azulene

C15H24 (204.1878)

15-(5-ethyl-6-methylhept-3-en-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C33H54O2 (482.4124)

(8e,10e,12e,14e,16e,18e,20e,22e,24e)-6,6,10,14,19,23,27,27-octamethyldotriaconta-8,10,12,14,16,18,20,22,24-nonaene-2,7,26,31-tetrone

C40H56O4 (600.4178)

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

C40H54O (550.4174)

4-[(9e,11e,13e,15e)-18-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]-3,5,5-trimethylcyclohex-3-ene-1,2-diol

C40H56O4 (600.4178)

(2r,5r,7r,8z,10e,12r,14s,19r,20s,27s,28s,29r,32r,33r,35r)-14-[(2s,3r,4r)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-35-(hydroxymethyl)-5,7,9,19,29-pentamethyl-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-18,31-dione

C47H70O15 (874.4714)

(1s,3r)-3-hydroxy-4-[(3z,5e,7e,9e,11e,13e,15e)-18-[(1s,4s,6r)-4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl]-3-(hydroxymethyl)-7,12,16-trimethyl-17-oxooctadeca-1,3,5,7,9,11,13,15-octaen-1-ylidene]-3,5,5-trimethylcyclohexyl acetate

C42H58O7 (674.4182)

(2r)-2-amino-3-{[(2s)-2-[(1r,3r,7r,10r,11r,14s,23r,24s,26r,31s,32s,33r,34r,35r)-11,34-dihydroxy-11,23,24,35-tetramethyl-16-methylidene-37,38,39,40,41-pentaoxa-21-azaoctacyclo[30.4.1.1¹,³³.1³,⁷.1⁷,¹⁰.1¹⁰,¹⁴.0²⁰,²⁶.0²⁶,³¹]hentetraconta-20,29-dien-29-yl]-2-hydroxyethyl]sulfanyl}propanoic acid

C45H70N2O10S (830.4751)

[(1r,3s,5r,7s,9r,11s,13r,14r,16s,18r,20s,22r,25s,27s,30s,31r,33r,34s,35r,37r,40s,42r,44s,46s,48r)-40-[(2s,3z)-2,6-dihydroxy-5-methylideneocta-3,7-dien-2-yl]-34-hydroxy-13,25,27,30,35-pentamethyl-39-methylidene-13-[2-(sulfooxy)ethyl]-4,8,12,17,21,26,32,36,41,45,49-undecaoxaundecacyclo[25.22.0.0³,²⁵.0⁵,²².0⁷,²⁰.0⁹,¹⁸.0¹¹,¹⁶.0³¹,⁴⁸.0³³,⁴⁶.0³⁵,⁴⁴.0³⁷,⁴²]nonatetracontan-14-yl]oxidanesulfonic acid

C55H82O22S2 (1158.4739)

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

C40H50O4 (594.3709)

(1r,3r,6s,7s,8r,11r,12s,15r,16r)-15-[(2r,5r)-5,6-dimethylheptan-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C30H52O (428.4018)

(1r,3as,3br,5as,7r,9ar,9br,11ar)-9a,11a-dimethyl-1-[(2r)-5-methylhexan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C28H48O2 (416.3654)

4-ethenyl-1-isopropyl-4-methyl-3-(prop-1-en-2-yl)cyclohex-1-ene

C15H24 (204.1878)

(3e,5e,7e,9e)-1-{4-hydroxy-2,2,6-trimethyl-7-oxabicyclo[4.1.0]heptan-1-yl}-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-17-yn-2-one

C40H54O4 (598.4022)

(1r,5r,6r,9s,10s,13s,15s)-6-[(2r,3e,5s)-5,6-dimethylhept-3-en-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C29H46O (410.3548)

(2e,4e,6e,8e,10e,12e,14e)-17-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-2,6,11,15-tetramethylheptadeca-2,4,6,8,10,12,14-heptaen-16-ynal

C30H38O2 (430.2872)

(1r,2s,5s,7s,8e,10z,12s,14r,16s,19s,20r,24r,27r,28r,29s,32s,33s,35r)-14-[(2r,3s,4s)-2,3-dihydroxy-4-methyloxan-2-yl]-28-hydroxy-5,7,9,19,29-pentamethyl-18,31-dioxo-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-35-carboxylic acid

C47H68O16 (888.4507)

(1r,3as,3br,5as,7s,9as,9bs,11as)-9a,11a-dimethyl-1-[(2s)-6-methylhept-3-en-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate

C29H48O2 (428.3654)

(1r,2r,4s)-1-[(1e,3e,5e,7e,9e,11e,13e,15e)-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-octaen-17-yn-1-yl]-2,6,6-trimethylcyclohexane-1,2,4-triol

C40H56O4 (600.4178)

(5z)-5-[(2e,4e)-9-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-7-methylnona-2,4,6-trien-8-yn-1-ylidene]-3-[2-(1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl)ethenyl]furan-2-one

C34H44O6 (548.3138)

(1s,3r)-4-[(3e,5e,7e,9e,11e,13e,15e,17e)-18-[(3r,4s)-3,4-dihydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-ylidene]-3-hydroxy-3,5,5-trimethylcyclohexyl acetate

C42H58O5 (642.4284)

(1s,3r,6s,7s,8s,11s,12s,15s,16r)-15-[(2r,5r)-5-isopropyl-6-methylhept-6-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C32H54O (454.4174)

(2z,4e,6e,8e,10e,12e,14e,16e,18e)-3-hydroxy-1-[(1r,4s)-4-hydroxy-1,2,2-trimethylcyclopentyl]-19-[(1r,2r,4s)-2-hydroxy-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-1-yl]-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16,18-nonaen-1-one

C40H56O5 (616.4128)

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

C40H56O6 (632.4077)

15-(5,6-dimethylheptan-2-yl)-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-ol

C30H52O (428.4018)

(5z)-5-[(2e,4e,6e,8e)-11-[(4s)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-2,9-dimethylundeca-2,4,6,8-tetraen-10-yn-1-ylidene]-3-[(1e)-2-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]ethenyl]furan-2-one

C37H48O6 (588.3451)

(1r,5r,6r,9s,10s,13s,15s)-6-[(2r,5r)-5-isopropyl-6-methylhept-6-en-2-yl]-5,9-dimethylpentacyclo[11.4.1.0¹,¹³.0²,¹⁰.0⁵,⁹]octadec-2-en-15-ol

C31H50O (438.3861)

n-[(2s,3r,4s)-1,3-dihydroxy-5-(tetradecanoyloxy)-4-[(4z,7z)-undeca-4,7-dienoyloxy]pentan-2-yl]dodecanimidic acid

C42H77NO7 (707.57)

3-{[(2s,3r,4s,5s,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

[C27H31O16]+ (611.1612)

(2r)-3-[(2s,5r,6r,8s)-8-[(2r,3e)-4-[(2r,4'ar,5r,6's,8'r,8'as)-8'-hydroxy-6'-[(1s,3s)-1-hydroxy-3-[(2s,3r,6r)-3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl]butyl]-7'-methylidene-hexahydrospiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl]-5-hydroxy-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl]-2-hydroxy-2-methylpropanoic acid

C44H68O13 (804.466)

(2s,3s,4s)-4-[(2z,4z,6r)-6-carboxy-6-methylhexa-2,4-dien-2-yl]-3-(carboxymethyl)pyrrolidine-2-carboxylic acid

C15H21NO6 (311.1369)

methyl (7s,28s)-14-ethenyl-19-ethyl-3,4-dihydroxy-13,18,23,28-tetramethyl-9,25,26,27-tetraazahexacyclo[20.2.1.1⁷,¹⁰.1¹²,¹⁵.1¹⁷,²⁰.0²,⁸]octacosa-1(25),2(8),3,9,11,13,15(27),16,18,20(26),21,23-dodecaene-24-carboxylate

C34H34N4O4 (562.258)

(1r,3r,6s,7s,8r,11r,12s,15r,16r)-15-[(2r,3e,5s)-5-ethyl-6-methylhept-3-en-2-yl]-7,12,16-trimethylpentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl acetate

C33H54O2 (482.4124)

(1s,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-isopropyl-6-methylhept-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

C30H50O (426.3861)

(1s,2r,4s)-2,6,6-trimethyl-1-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-[(1r,2r,4s)-1,2,4-trihydroxy-2,6,6-trimethylcyclohexyl]octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohexane-1,2,4-triol

C40H60O6 (636.439)

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

C40H54O4 (598.4022)

(2z,4e,6e,8e,10e)-3-hydroxy-1-(4-hydroxy-1,2,2-trimethylcyclopentyl)-19-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-4,8,13,17-tetramethylnonadeca-2,4,6,8,10,12,14,16-octaen-18-yn-1-one

C40H54O4 (598.4022)

(2z,4e,6e,8e,10e,12e,14e,16z)-3-hydroxy-1-[(1r,4s)-4-hydroxy-1,2,2-trimethylcyclopentyl]-19-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-17-(hydroxymethyl)-4,8,13-trimethylnonadeca-2,4,6,8,10,12,14,16-octaen-18-yn-1-one

C40H54O5 (614.3971)

(1s,2r)-4-[(3e,5e,7e,9e,11e,13e,15e)-18-[(4r)-4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl]-3,7,12,16-tetramethyloctadeca-3,5,7,9,11,13,15-heptaen-1,17-diyn-1-yl]-3,5,5-trimethylcyclohex-3-ene-1,2-diol

C40H52O3 (580.3916)

1-[(9e,11e,13e,15e)-18-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15-octaen-17-yn-1-yl]-2,6,6-trimethyl-7-oxabicyclo[2.2.1]heptan-2-ol

C40H54O3 (582.4073)

14-(2,3-dihydroxy-4-methyloxan-2-yl)-28-hydroxy-5,7,9,19,29-pentamethyl-18,31-dioxo-13,17,38,39,40,41,42,43-octaoxaoctacyclo[31.4.1.1¹,³⁵.1²,⁵.1²⁰,²⁴.1²⁴,²⁷.1²⁹,³².0¹²,¹⁶]tritetraconta-8,10-diene-35-carboxylic acid

C47H68O16 (888.4507)

(2s)-5-carbamimidamido-2-({[(2s,4s)-1-[(2r)-2-{[(2r)-1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-(4-hydroxyphenyl)butanoyl]-4-methylpyrrolidin-2-yl](hydroxy)methylidene}amino)pentanoic acid

C31H42N6O8 (626.3064)