NCBI Taxonomy: 13840

Spinulum annotinum (ncbi_taxid: 13840)

found 94 associated metabolites at species taxonomy rank level.

Ancestor: Spinulum

Child Taxonomies: [Lycopodium] annotinum subsp. alpestre, [Lycopodium] annotinum subsp. annotinum

Nicotine

(S)-(-)-NICOTINE; 3-[(2S)-1-METHYL-2-PYRROLIDINYL] PYRIDINE

C10H14N2 (162.1156924)


Nicotine is an alkaloid found in the nightshade family of plants (Solanaceae), predominantly in tobacco and in lower quantities in tomato, potato, eggplant (aubergine), and green pepper. Nicotine alkaloids are also found in the leaves of the coca plant. Nicotine constitutes 0.3 to 5\\\% of the tobacco plant by dry weight, with biosynthesis taking place in the root and accumulation in the leaves. It is a potent neurotoxin with particular specificity to insects; therefore nicotine was widely used as an insecticide in the past and nicotine derivatives such as imidacloprid continue to be widely used. It has been noted that the majority of people diagnosed with schizophrenia smoke tobacco. Estimates for the number of schizophrenics that smoke range from 75\\\% to 90\\\%. It was recently argued that the increased level of smoking in schizophrenia may be due to a desire to self-medicate with nicotine. More recent research has found the reverse: it is a risk factor without long-term benefit, used only for its short-term effects. However, research on nicotine as administered through a patch or gum is ongoing. As nicotine enters the body, it is distributed quickly through the bloodstream and can cross the blood-brain barrier. On average, it takes about seven seconds for the substance to reach the brain. The half-life of nicotine in the body is around 2 hours. The amount of nicotine inhaled with tobacco smoke is a fraction of the amount contained in the tobacco leaves (most of the substance is destroyed by the heat). The amount of nicotine absorbed by the body from smoking depends on many factors, including the type of tobacco, whether the smoke is inhaled, and whether a filter is used. For chewing tobacco, often called dip, snuff, or sinus, which is held in the mouth between the lip and gum, the amount released into the body tends to be much greater than smoked tobacco. The currently available literature indicates that nicotine, on its own, does not promote the development of cancer in healthy tissue and has no mutagenic properties. Its teratogenic properties have not yet been adequately researched, and while the likelihood of birth defects caused by nicotine is believed to be very small or nonexistent, nicotine replacement product manufacturers recommend consultation with a physician before using a nicotine patch or nicotine gum while pregnant or nursing. However, nicotine and the increased acetylcholinic activity it causes have been shown to impede apoptosis, which is one of the methods by which the body destroys unwanted cells (programmed cell death). Since apoptosis helps to remove mutated or damaged cells that may eventually become cancerous, the inhibitory actions of nicotine create a more favourable environment for cancer to develop. Thus, nicotine plays an indirect role in carcinogenesis. It is also important to note that its addictive properties are often the primary motivating factor for tobacco smoking, contributing to the proliferation of cancer. Nicotine is a highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke. Nicotine is a hygroscopic, oily liquid that is miscible with water in its base form. As a nitrogenous base, nicotine forms salts with acids that are usually solid and water soluble. Nicotine easily penetrates the skin. As shown by the physical data, free base nicotine will burn at a temperature below its boiling point, and its vapours will combust at 95 °C in the air despite a low vapour pressure. Because of this, most nicotine is burned when a cigarette is smoked; however, enough is inhaled to provide the desired effects. Nicotine is a stimulant drug that acts as an agonist at nicotinic acetylcholine receptors. These are ionotropic receptors composed of five homomeric or heteromeric subunits. In the brain, nicotine binds to nic... Nicotine appears as a colorless to light yellow or brown liquid. Combustible. Toxic by inhalation and by skin absorption. Produces toxic oxides of nitrogen during combustion. (S)-nicotine is a 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum. It has a role as a phytogenic insecticide, a teratogenic agent, a neurotoxin, an anxiolytic drug, a nicotinic acetylcholine receptor agonist, a biomarker, an immunomodulator, a mitogen, a peripheral nervous system drug, a psychotropic drug, a plant metabolite and a xenobiotic. It is a conjugate base of a (S)-nicotinium(1+). It is an enantiomer of a (R)-nicotine. Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke. Nicotine is a Cholinergic Nicotinic Agonist. Nicotine is a natural alkyloid that is a major component of cigarettes and is used therapeutically to help with smoking cessation. Nicotine has not been associated with liver test abnormalities or with clinically apparent hepatotoxicity. Nicotine is a natural product found in Cyphanthera tasmanica, Nicotiana cavicola, and other organisms with data available. Nicotine is a plant alkaloid, found in the tobacco plant, and addictive central nervous system (CNS) stimulant that causes either ganglionic stimulation in low doses or ganglionic blockage in high doses. Nicotine acts as an agonist at the nicotinic cholinergic receptors in the autonomic ganglia, at neuromuscular junctions, and in the adrenal medulla and the brain. Nicotines CNS-stimulating activities may be mediated through the release of several neurotransmitters, including acetylcholine, beta-endorphin, dopamine, norepinephrine, serotonin, and ACTH. As a result, peripheral vasoconstriction, tachycardia, and elevated blood pressure may be observed with nicotine intake. This agent may also stimulate the chemoreceptor trigger zone, thereby inducing nausea and vomiting. Nicotine is highly toxic alkaloid. It is the prototypical agonist at nicotinic cholinergic receptors where it dramatically stimulates neurons and ultimately blocks synaptic transmission. Nicotine is also important medically because of its presence in tobacco smoke. See also: Tobacco Leaf (part of); Nicotine Polacrilex (related); Menthol; nicotine (component of) ... View More ... Alkaloid from Nicotiana tabacum and other Nicotiana subspecies, Asclepias syriaca, Lycopodium subspecies, and other subspecies (Solanaceae, Asclepiadaceae, Crassulaceae). Rare spread of occurrence between angiosperms and cryptogametes (CCD) A 3-(1-methylpyrrolidin-2-yl)pyridine in which the chiral centre has S-configuration. The naturally occurring and most active enantiomer of nicotine, isolated from Nicotiana tabacum.

   

beta-Carotene

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

C40H56 (536.4381776)


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

   

Lutein

(1R,4R)-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 (568.4280076)


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].

   

beta-Cryptoxanthin

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

C40H56O (552.4330926)


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

   

Zeaxanthin

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

C40H56O2 (568.4280076)


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

   

Neoxanthin

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

C40H56O4 (600.4178376)


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

   

Violaxanthin

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

C40H56O4 (600.4178376)


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

   

Lutein 5,6-epoxide

(1R,3S,6S)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-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

C40H56O3 (584.4229226)


Lutein; 5,6-Epoxide is found in common grape. Paprika oleoresin (also known as paprika extract) is an oil soluble extract from the fruits of Capsicum Annum Linn or Capsicum Frutescens(Indian red chillies), and is primarily used as a colouring and/or flavouring in food products. It is composed of capsaicin, the main flavouring compound giving pungency in higher concentrations, and capsanthin and capsorubin, the main colouring compounds (among other carotenoids). Isolated from a variety of higher plants and from algae. Taraxanthin was a mixture with lutein epoxide as the main component. [CCD]. Lutein 5,6-epoxide is found in many foods, some of which are rice, swamp cabbage, garden tomato (variety), and common grape.

   

Rhodoxanthin

DTXSID10275904

C40H50O2 (562.3810599999999)


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

   

Piperideine

1-Piperideine

C5H9N (83.0734954)


   

Acrifoline

Alkaloid L27

C16H23NO2 (261.1728698)


A quinolizidine alkaloid that is lycopodine having a C=C double bond at the 11-position, a keto substituent at the 8-position and the keto group at position 5 replaced by a beta-hydroxy group.

   

Annofoline

Annofoline; (15R)-5beta-Hydroxy-15-methyllycopodan-8-one

C16H25NO2 (263.188519)


   

Lycodine

1H-5,10b-Propano-1,7-phenanthroline, lycodine deriv.

C16H22N2 (242.1782892)


   

Lycopodine

12-Epilycopodine

C16H25NO (247.193604)


   
   

5-Aminopentanal

5-Amino-pentanal

C5H11NO (101.0840596)


The aminoaldehydes 5-aminopentanal, derived from the oxidation of the diamines putrescine and cadaverine,is produced utilizing a copper amine oxidase (CAO) from Euphorbia characias latex and tested with in vitro cultivation of Leishmania infantum promastigotes.Whereas the aminoaldehydes derived from the oxidation of the diamines were stimulating factors for growth of Leishmania infantum promastigotes, the aldehydes derived from polyamines oxidation had a drastic inhibitory effect on the vitality and growth of these parasites. Thus, a double scenario arises, showing the use of aldehydes from diamines to obtain a large number of organisms of Leishmania infantum promastigotes to use in serological studies, whereas the aldehydes derived from polyamines could be used as a new strategy for therapeutic treatment against these parasites. [HMDB]. 5-Aminopentanal is found in many foods, some of which are watermelon, sorrel, medlar, and cornmint. The aminoaldehydes 5-aminopentanal, derived from the oxidation of the diamines putrescine and cadaverine,is produced utilizing a copper amine oxidase (CAO) from Euphorbia characias latex and tested with in vitro cultivation of Leishmania infantum promastigotes.Whereas the aminoaldehydes derived from the oxidation of the diamines were stimulating factors for growth of Leishmania infantum promastigotes, the aldehydes derived from polyamines oxidation had a drastic inhibitory effect on the vitality and growth of these parasites. Thus, a double scenario arises, showing the use of aldehydes from diamines to obtain a large number of organisms of Leishmania infantum promastigotes to use in serological studies, whereas the aldehydes derived from polyamines could be used as a new strategy for therapeutic treatment against these parasites.

   

(R)-Pelletierine

1-[(2R)-piperidin-2-yl]propan-2-one

C8H15NO (141.115358)


(R)-Pelletierine is found in fruits. (R)-Pelletierine is an alkaloid from pomegranat Alkaloid from pomegranate. (R)-Pelletierine is found in fruits and pomegranate.

   

Lycodine

(4aR,12R)-2,3,4,4abeta,5,6-Hexahydro-12-methyl-1H-5beta,10bbeta-propano-1,7-phenanthroline

C16H22N2 (242.1782892)


   

Nicotine

L-(-)-Nicotine

C10H14N2 (162.1156924)


N - Nervous system > N07 - Other nervous system drugs > N07B - Drugs used in addictive disorders > N07BA - Drugs used in nicotine dependence D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D005731 - Ganglionic Stimulants C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist > C73579 - Nicotinic Agonist D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials CONFIDENCE standard compound; EAWAG_UCHEM_ID 3008 D000077444 - Smoking Cessation Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Neoxanthin

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

C40H56O4 (600.4178376)


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

   

Nicotine

(S)-(-)-NICOTINE, 3-[(2S)-1-METHYL-2-PYRROLIDINYL] PYRIDINE

C10H14N2 (162.1156924)


An N-alkylpyrrolidine that consists of N-methylpyrrolidine bearing a pyridin-3-yl substituent at position 2. It has been isolated from Nicotiana tabacum. N - Nervous system > N07 - Other nervous system drugs > N07B - Drugs used in addictive disorders > N07BA - Drugs used in nicotine dependence D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D005731 - Ganglionic Stimulants C78272 - Agent Affecting Nervous System > C47796 - Cholinergic Agonist > C73579 - Nicotinic Agonist D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018679 - Cholinergic Agonists COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D000077444 - Smoking Cessation Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2264 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053

   

β-Carotene

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

C40H56 (536.4381776)


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

   
   

Violaxanthin

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

C40H56O4 (600.4178376)


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

   

Cryptoxanthin

(all-E)-beta-Cryptoxanthin

C40H56O (552.4330926)


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

   

Zeaxanthin

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

C40H56O2 (568.4280076)


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

   

(R)-Pelletierine

1-[(2R)-piperidin-2-yl]propan-2-one

C8H15NO (141.115358)


   

5-Aminopentanal

5-Aminopentanal

C5H11NO (101.0840596)


An omega-aminoaldehyde that is pentanal which is substituted at position 5 by an amino group. It is an intermediate in the biosynthesis of L-lysine derived alkaloids.

   

(±)-nicotine

3-(1-methylpyrrolidin-2-yl)pyridine

C10H14N2 (162.1156924)


An N-alkylpyrrolidine that consists of N-methylpyrrolidine bearing a pyridin-3-yl substituent at position 2.

   

1-[(2R)-piperidin-2-yl]propan-2-one

1-[(2R)-piperidin-2-yl]propan-2-one

C8H15NO (141.115358)


   

methyl 8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-10-ene-10-carboxylate

methyl 8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-10-ene-10-carboxylate

C17H25NO3 (291.18343400000003)


   

(1r,2r,10s,11r,13s,14s,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl acetate

(1r,2r,10s,11r,13s,14s,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl acetate

C18H29NO3 (307.2147324)


   

(1s,10s,13s,14r,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-one

(1s,10s,13s,14r,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-one

C16H23NO2 (261.1728698)


   

(1r,2r,10s,11r,13s,14r,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

(1r,2r,10s,11r,13s,14r,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C26H35NO5 (441.25151000000005)


   

methyl (1s,7s,8r,12r,14s)-8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-10-ene-10-carboxylate

methyl (1s,7s,8r,12r,14s)-8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-10-ene-10-carboxylate

C17H25NO3 (291.18343400000003)


   

(1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene

(1r,9r,10r,16r)-16-methyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-triene

C16H22N2 (242.1782892)


   

(1s,10s,11s,12s,13r,15r)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,12-diol

(1s,10s,11s,12s,13r,15r)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,12-diol

C16H25NO2 (263.188519)


   

(1s,10s,11r,13s,14s,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

(1s,10s,11r,13s,14s,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C26H33NO5 (439.23586080000007)


   

n-[(1s,2r,7r,13r,15s)-15-methyl-7-(2-oxopropyl)-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-10-en-11-yl]ethanimidic acid

n-[(1s,2r,7r,13r,15s)-15-methyl-7-(2-oxopropyl)-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-10-en-11-yl]ethanimidic acid

C21H32N2O2 (344.24636519999996)


   

2-[(2e,4e,6e,8e,10e,12e,14e,16e)-17-(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

2-[(2e,4e,6e,8e,10e,12e,14e,16e)-17-(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 (584.4229226)


   

(1r,9s,10r,16r)-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-5-ol

(1r,9s,10r,16r)-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-5-ol

C17H24N2O (272.18885339999997)


   

2,3-dihydroxy-14-methyl-11-oxa-5-azapentacyclo[7.4.3.1¹⁰,¹³.0¹,¹⁶.0⁵,¹⁶]heptadecan-12-one

2,3-dihydroxy-14-methyl-11-oxa-5-azapentacyclo[7.4.3.1¹⁰,¹³.0¹,¹⁶.0⁵,¹⁶]heptadecan-12-one

C16H23NO4 (293.1626998)


   

(1s,10r,11s,13s,14s,15s)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,14-diol

(1s,10r,11s,13s,14s,15s)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,14-diol

C16H25NO2 (263.188519)


   

14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-one

14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-one

C16H23NO2 (261.1728698)


   

15-methyl-3,12-dioxa-6-azahexacyclo[8.4.3.1¹¹,¹⁴.0¹,¹⁷.0²,⁴.0⁶,¹⁷]octadecan-13-one

15-methyl-3,12-dioxa-6-azahexacyclo[8.4.3.1¹¹,¹⁴.0¹,¹⁷.0²,⁴.0⁶,¹⁷]octadecan-13-one

C16H21NO3 (275.1521356)


   

15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,12-diol

15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,12-diol

C16H25NO2 (263.188519)


   

methyl (2s)-3-[(8r,9s,13s)-8-hydroxy-1-azatricyclo[7.3.1.0⁵,¹³]trideca-3,5-dien-13-yl]-2-methylpropanoate

methyl (2s)-3-[(8r,9s,13s)-8-hydroxy-1-azatricyclo[7.3.1.0⁵,¹³]trideca-3,5-dien-13-yl]-2-methylpropanoate

C17H25NO3 (291.18343400000003)


   

16-methyl-14-oxa-6-azatetracyclo[8.7.0.0¹,⁶.0²,¹³]heptadeca-8,10-dien-15-one

16-methyl-14-oxa-6-azatetracyclo[8.7.0.0¹,⁶.0²,¹³]heptadeca-8,10-dien-15-one

C16H21NO2 (259.1572206)


   

(1r,9s,10r,16s)-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-5-ol

(1r,9s,10r,16s)-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-5-ol

C17H24N2O (272.18885339999997)


   
   

(1s,2r,7r,10s,11r,13r,15s)-15-methyl-7-(2-oxopropyl)-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

(1s,2r,7r,10s,11r,13r,15s)-15-methyl-7-(2-oxopropyl)-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C29H39NO5 (481.2828084)


   

(1r,9s,10r,13s,14r,16s)-14-methyl-11-oxa-5-azapentacyclo[7.4.3.1¹⁰,¹³.0¹,¹⁶.0⁵,¹⁶]heptadec-3-ene-2,12-dione

(1r,9s,10r,13s,14r,16s)-14-methyl-11-oxa-5-azapentacyclo[7.4.3.1¹⁰,¹³.0¹,¹⁶.0⁵,¹⁶]heptadec-3-ene-2,12-dione

C16H19NO3 (273.13648639999997)


   

n-[15-methyl-7-(2-oxopropyl)-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-10-en-11-yl]ethanimidic acid

n-[15-methyl-7-(2-oxopropyl)-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-10-en-11-yl]ethanimidic acid

C21H32N2O2 (344.24636519999996)


   

(1s,2s,13r,16s)-16-methyl-14-oxa-6-azatetracyclo[8.7.0.0¹,⁶.0²,¹³]heptadeca-8,10-dien-15-one

(1s,2s,13r,16s)-16-methyl-14-oxa-6-azatetracyclo[8.7.0.0¹,⁶.0²,¹³]heptadeca-8,10-dien-15-one

C16H21NO2 (259.1572206)


   

(1r,2r,4r,6s,9r)-2-hydroxy-4-methyl-13-azatetracyclo[7.7.0.0¹,⁶.0²,¹³]hexadecan-8-one

(1r,2r,4r,6s,9r)-2-hydroxy-4-methyl-13-azatetracyclo[7.7.0.0¹,⁶.0²,¹³]hexadecan-8-one

C16H25NO2 (263.188519)


   

(1r,12s,16r)-14-methyl-10-oxo-5-azatricyclo[10.4.0.0⁵,¹⁶]hexadecan-5-ium-5-olate

(1r,12s,16r)-14-methyl-10-oxo-5-azatricyclo[10.4.0.0⁵,¹⁶]hexadecan-5-ium-5-olate

C16H27NO2 (265.20416819999997)


   

14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C26H33NO5 (439.23586080000007)


   

(1r,2s,4r,10s,11r,14s,15r,17s)-15-methyl-3,12-dioxa-6-azahexacyclo[8.4.3.1¹¹,¹⁴.0¹,¹⁷.0²,⁴.0⁶,¹⁷]octadecan-13-one

(1r,2s,4r,10s,11r,14s,15r,17s)-15-methyl-3,12-dioxa-6-azahexacyclo[8.4.3.1¹¹,¹⁴.0¹,¹⁷.0²,⁴.0⁶,¹⁷]octadecan-13-one

C16H21NO3 (275.1521356)


   

14-methyl-11-oxa-5-azapentacyclo[7.4.3.1¹⁰,¹³.0¹,¹⁶.0⁵,¹⁶]heptadec-3-ene-2,12-dione

14-methyl-11-oxa-5-azapentacyclo[7.4.3.1¹⁰,¹³.0¹,¹⁶.0⁵,¹⁶]heptadec-3-ene-2,12-dione

C16H19NO3 (273.13648639999997)


   

methyl 8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-11(15)-ene-10-carboxylate

methyl 8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-11(15)-ene-10-carboxylate

C17H25NO3 (291.18343400000003)


   

2-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-one

2-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-one

C16H25NO2 (263.188519)


   

(2s)-2-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-one

(2s)-2-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-one

C16H25NO2 (263.188519)


   

(1r,9s,10r,13s,14s)-14-propyl-11-oxa-5-azatetracyclo[7.4.1.1¹⁰,¹³.0⁵,¹⁴]pentadec-3-ene-2,12-dione

(1r,9s,10r,13s,14s)-14-propyl-11-oxa-5-azatetracyclo[7.4.1.1¹⁰,¹³.0⁵,¹⁴]pentadec-3-ene-2,12-dione

C16H21NO3 (275.1521356)


   

14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl acetate

14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl acetate

C18H29NO3 (307.2147324)


   

15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,14-diol

15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,14-diol

C16H25NO2 (263.188519)


   

(1r,2s,4r,10s,11r,14s,15s,17s)-15-methyl-3,12-dioxa-6-azahexacyclo[8.4.3.1¹¹,¹⁴.0¹,¹⁷.0²,⁴.0⁶,¹⁷]octadecan-13-one

(1r,2s,4r,10s,11r,14s,15s,17s)-15-methyl-3,12-dioxa-6-azahexacyclo[8.4.3.1¹¹,¹⁴.0¹,¹⁷.0²,⁴.0⁶,¹⁷]octadecan-13-one

C16H21NO3 (275.1521356)


   

(7s,8r,10s,12s,14s)-8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-11(15)-ene-10-carboxylic acid

(7s,8r,10s,12s,14s)-8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-11(15)-ene-10-carboxylic acid

C16H23NO3 (277.1677848)


   

n-[(1r,2r,7r,13s,15r)-15-methyl-7-(2-oxopropyl)-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-10-en-11-yl]ethanimidic acid

n-[(1r,2r,7r,13s,15r)-15-methyl-7-(2-oxopropyl)-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-10-en-11-yl]ethanimidic acid

C21H32N2O2 (344.24636519999996)


   

14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol

14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol

C17H26N2O (274.2045026)


   

(1s,10s,11r,13s,14r,15s)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,14-diol

(1s,10s,11r,13s,14r,15s)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,14-diol

C16H25NO2 (263.188519)


   

(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

(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 (584.4229226)


   

15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-one

15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-one

C16H25NO (247.193604)


   

methyl 3-{8-hydroxy-1-azatricyclo[7.3.1.0⁵,¹³]trideca-3,5-dien-13-yl}-2-methylpropanoate

methyl 3-{8-hydroxy-1-azatricyclo[7.3.1.0⁵,¹³]trideca-3,5-dien-13-yl}-2-methylpropanoate

C17H25NO3 (291.18343400000003)


   

14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-5-ol

14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2,4,6-trien-5-ol

C17H24N2O (272.18885339999997)


   

methyl (1s,7s,8r,10s,12s)-8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-11(15)-ene-10-carboxylate

methyl (1s,7s,8r,10s,12s)-8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-11(15)-ene-10-carboxylate

C17H25NO3 (291.18343400000003)


   

(1r,2s,3s,9s,10r,13s,14r,16s)-2,3-dihydroxy-14-methyl-11-oxa-5-azapentacyclo[7.4.3.1¹⁰,¹³.0¹,¹⁶.0⁵,¹⁶]heptadecan-12-one

(1r,2s,3s,9s,10r,13s,14r,16s)-2,3-dihydroxy-14-methyl-11-oxa-5-azapentacyclo[7.4.3.1¹⁰,¹³.0¹,¹⁶.0⁵,¹⁶]heptadecan-12-one

C16H23NO4 (293.1626998)


   

10-hydroxy-16-methyl-14-oxa-6-azapentacyclo[8.7.0.0¹,⁶.0²,¹³.0¹¹,¹⁶]heptadec-8-en-15-one

10-hydroxy-16-methyl-14-oxa-6-azapentacyclo[8.7.0.0¹,⁶.0²,¹³.0¹¹,¹⁶]heptadec-8-en-15-one

C16H21NO3 (275.1521356)


   

11-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-14-one

11-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-14-one

C16H23NO2 (261.1728698)


   

(1s,2s,13r)-16-methyl-14-oxa-6-azatetracyclo[8.7.0.0¹,⁶.0²,¹³]heptadeca-8,10-dien-15-one

(1s,2s,13r)-16-methyl-14-oxa-6-azatetracyclo[8.7.0.0¹,⁶.0²,¹³]heptadeca-8,10-dien-15-one

C16H21NO2 (259.1572206)


   

(1s,2s,10s,11r,13r,16r)-10-hydroxy-16-methyl-14-oxa-6-azapentacyclo[8.7.0.0¹,⁶.0²,¹³.0¹¹,¹⁶]heptadec-8-en-15-one

(1s,2s,10s,11r,13r,16r)-10-hydroxy-16-methyl-14-oxa-6-azapentacyclo[8.7.0.0¹,⁶.0²,¹³.0¹¹,¹⁶]heptadec-8-en-15-one

C16H21NO3 (275.1521356)


   

(1r,2r,10s,11r,13s,14s,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

(1r,2r,10s,11r,13s,14s,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C26H35NO5 (441.25151000000005)


   

(1s,2s,10s,13s,15r)-2-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-one

(1s,2s,10s,13s,15r)-2-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-one

C16H25NO2 (263.188519)


   

(1s,10s,11r,13s,14r,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

(1s,10s,11r,13s,14r,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C26H33NO5 (439.23586080000007)


   

methyl (1s,7s,8r,10s,12s,14s)-8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-11(15)-ene-10-carboxylate

methyl (1s,7s,8r,10s,12s,14s)-8-hydroxy-14-methyl-3-azatetracyclo[9.3.1.0³,¹².0⁷,¹²]pentadec-11(15)-ene-10-carboxylate

C17H25NO3 (291.18343400000003)


   

14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl 3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C26H35NO5 (441.25151000000005)


   

(1r,9s,10r,16r)-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol

(1r,9s,10r,16r)-14,16-dimethyl-6,14-diazatetracyclo[7.5.3.0¹,¹⁰.0²,⁷]heptadeca-2(7),5-dien-5-ol

C17H26N2O (274.2045026)


   

11-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-14-one

11-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-14-one

C16H25NO2 (263.188519)


   

(1r,2s,3s,9s,10r,13s,14s)-2,3-dihydroxy-14-propyl-11-oxa-5-azatetracyclo[7.4.1.1¹⁰,¹³.0⁵,¹⁴]pentadecan-12-one

(1r,2s,3s,9s,10r,13s,14s)-2,3-dihydroxy-14-propyl-11-oxa-5-azatetracyclo[7.4.1.1¹⁰,¹³.0⁵,¹⁴]pentadecan-12-one

C16H25NO4 (295.178349)


   

(1s,10s,11r,13s,15r)-15-methyl-14-oxo-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-yl acetate

(1s,10s,11r,13s,15r)-15-methyl-14-oxo-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-en-11-yl acetate

C18H25NO3 (303.18343400000003)


   

(1s,10s,11r,13s,14s,15s)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,14-diol

(1s,10s,11r,13s,14s,15s)-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadec-2-ene-11,14-diol

C16H25NO2 (263.188519)


   

(1r,2r,10s,11r,13s,14r,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl acetate

(1r,2r,10s,11r,13s,14r,15s)-14-hydroxy-15-methyl-6-azatetracyclo[8.6.0.0¹,⁶.0²,¹³]hexadecan-11-yl acetate

C18H29NO3 (307.2147324)