NCBI Taxonomy: 178475

Niphatidae (ncbi_taxid: 178475)

found 500 associated metabolites at family taxonomy rank level.

Ancestor: Haplosclerida

Child Taxonomies: Aka, Niphates, Gelliodes, Microxina, Amphimedon, Hemigellius, Dasychalina, Pachychalina, Cribrochalina, unclassified Niphatidae

Fucoxanthin

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

C42H58O6 (658.4233168)


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

   

Tryptamine

2-(1H-indol-3-yl)ethan-1-amine

C10H12N2 (160.1000432)


Tryptamine, also known as TrpN, is a catabolite of tryptophan converted by the gut microbiota. After absorption through the intestinal epithelium, tryptophan catabolites enter the bloodstream and are later excreted in the urine. Both Clostridium sp. and Ruminococcus sp. have been found to convert tryptophan into tryptamine (PMID: 30120222). Tryptamine is a monoamine compound that is a common precursor molecule to many hormones and neurotransmitters. Biosynthesis generally proceeds from the amino acid tryptophan, with tryptamine acting as a precursor for other compounds. Substitutions to the tryptamine molecule give rise to a group of compounds collectively known as tryptamines. The most well-known tryptamines are serotonin, an important neurotransmitter, and melatonin, a hormone involved in regulating the sleep-wake cycle. Tryptamine has been detected, but not quantified in, several different foods, such as onion-family vegetables, acerola, Japanese walnuts, custard apples, and green zucchinis. This could make tryptamine a potential biomarker for the consumption of these foods. Tryptamine is an aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. It has a role as a human metabolite, a plant metabolite and a mouse metabolite. It is an aminoalkylindole, an indole alkaloid, an aralkylamino compound and a member of tryptamines. It is a conjugate base of a tryptaminium. Tryptamine is a natural product found in Mus musculus, Prosopis glandulosa, and other organisms with data available. Occurs widely in plants, especies Lens esculenta (lentil) and the fungi Coprinus micaceus (glistening ink cap) An aminoalkylindole consisting of indole having a 2-aminoethyl group at the 3-position. KEIO_ID T031

   

Myristic acid

tetradecanoic acid

C14H28O2 (228.20891880000002)


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

   

Palmitic acid

hexadecanoic acid

C16H32O2 (256.2402172)


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

   

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

   

Astaxanthin

3,3-Dihydroxy-beta,beta-carotene-4,4-dione;(S)-6-hydroxy-3-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-((S)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-enyl)-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl)-2,4,4-trimethylcyclohex-2-enone;

C40H52O4 (596.3865392)


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

   

alpha-Carotene

(6R)-1,5,5-trimethyl-6-[(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)


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

(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

   

Octacosanoic acid

Octacosanoic acid, puriss., synthetic, >=98.5\\% (GC)

C28H56O2 (424.4280076)


Octacosanoic acid is a very-long-chain fatty acid found in human brain and visceral organs (PMID:2474624). Octacosanoic acid is a higher aliphatic primary acids purified from sugar-cane (Saccharum officinarum L.) wax that has been shown to inhibit platelet aggregation induced ex vivo by addition of agonists to platelet-rich plasma (PRP) of rats, guinea pigs, and healthy human volunteers. (PMID:5099499). Octacosanoic acid is formed from octacosanol via beta-oxidation. (PMID:15847942). Octacosanoic acid is a straight-chain saturated fatty acid that is octacosane in which one of the terminal methyl groups has been oxidised to the corresponding carboxy group. It has a role as a plant metabolite. It is a straight-chain saturated fatty acid and an ultra-long-chain fatty acid. It is a conjugate acid of an octacosanoate. Octacosanoic acid is a natural product found in Lysimachia patungensis, Rhizophora apiculata, and other organisms with data available. A straight-chain saturated fatty acid that is octacosane in which one of the terminal methyl groups has been oxidised to the corresponding carboxy group. Octacosanoic acid is a very-long-chain fatty acid found in human brain and visceral organs (PMID: 2474624)

   

Pregnenolone

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

C21H32O2 (316.24021719999996)


Pregnenolone is a derivative of cholesterol, the product of cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1. This reaction consists of three consecutive monooxygenations, a 22-hydroxylation, a 20-hydroxylation, and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum, and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted into pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell, angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and many steps in the transport to the inner membrane. Thus, it exerts a powerful control over the use of cholesterol for aldosterone production (PMID: 17222962, 15823613, 16632873, 15134809). C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3]. Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

   

Stearic acid

1-Heptadecanecarboxylic acid

C18H36O2 (284.2715156)


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

   

Oleic acid

Emersol 221 low titer white oleic acid

C18H34O2 (282.2558664)


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

   

Lignoceric acid (C24)

Tetracosanoic acid

C24H48O2 (368.3654108)


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

   

Vaccenic acid

11-Octadecenoic acid, (e)-isomer

C18H34O2 (282.2558664)


Vaccenic acid is a naturally occurring trans fatty acid. It is the predominant kind of trans-fatty acid found in human milk, in the fat of ruminants, and in dairy products such as milk, butter, and yogurt. Trans fat in human milk may depend on trans fat content in food. Its IUPAC name is (11E)-11-octadecenoic acid, and its lipid shorthand name is 18:1 trans-11. The name was derived from the Latin vacca (cow). Vaccenic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Vaccenic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Occurs in small proportions in ruminant fats (e.g., butter) via biohydrogenation of dietary polyene acids. Vaccenic acid is found in many foods, some of which are almond, romaine lettuce, butter, and pak choy. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

   

Behenic acid

Docosanoic acid from Rapeseed

C22H44O2 (340.3341124)


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

   

Canthaxanthin

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

C40H52O2 (564.3967092)


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

Echinenone/ (Myxoxanthin)

C40H54O (550.4174434)


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.

   

Spheroidenone

(3E)-1-methoxy-3,4-didehydro-1,2,7,8-tetrahydro- , -caroten-2-one

C41H58O2 (582.4436568)


The carotenone that is the 2-oxo derivative of (3E)-1-methoxy-3,4-didehydro-1,2,7,8-tetrahydro-psi,psi-carotene. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

24-Methylenecholesterol

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

C28H46O (398.3548466)


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

   

Nonadecanoic acid

nonadecanoic acid

C19H38O2 (298.28716479999997)


Nonadecanoic acid, also known as n-nonadecanoic acid or nonadecylic acid or C19:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms, with nonadecanoic acid (its ester is called nonadecanoate) having 19 carbon atoms. Nonadecanoic acid is a very hydrophobic molecule, practically insoluble (in water). It is a solid with a melting point of 69.4°C. It can be found in bacteria, plants, and animals (including animal milk) (Nature 176:882; PMID: 14168161). It is secreted by termites (Rhinotermes marginalis) as part of its defence mechanism (Comp. Biochem. Physiol. B 71:731). Nonadecanoic acid is a C19 straight-chain fatty acid of plant or bacterial origin. An intermediate in the biodegradation of n-icosane, it has been shown to inhibit cancer growth. It has a role as a fungal metabolite. It is a straight-chain saturated fatty acid and a long-chain fatty acid. It is a conjugate acid of a nonadecanoate. Nonadecanoic acid is a natural product found in Staphisagria macrosperma, Malva sylvestris, and other organisms with data available. An odd-numbered long chain fatty acid, likely derived from bacterial or plant sources. Nonadecanoic acid has been found in ox fats and vegetable oils. It is also used by certain insects as a phermone. [HMDB]. A C19 straight-chain fatty acid of plant or bacterial origin. An intermediate in the biodegradation of n-icosane, it has been shown to inhibit cancer growth. Nonadecanoic acid is a 19-carbon long saturated fatty acid. Nonadecanoic acid is the major constituent of the substance secreted by Rhinotermes marginalis to defence[1]. Nonadecanoic acid is a 19-carbon long saturated fatty acid. Nonadecanoic acid is the major constituent of the substance secreted by Rhinotermes marginalis to defence[1].

   

Halistanol sulfate

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

C29H52O12S3 (688.2620751999999)


   

Manzamine A

Keramamine A

C36H44N4O (548.3514934)


An alkaloid of the class of beta-carbolines isolated from Haliclona and Acanthostrongylophora. It exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).

   

Hexacosanoic acid

Hexacosanoate (N-C26:0)

C26H52O2 (396.3967092)


Hexacosanoic acid, also known as N-hexacosanoate or c26:0, is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Thus, hexacosanoic acid is considered to be a fatty acid lipid molecule. Hexacosanoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Hexacosanoic acid can be found in a number of food items such as dandelion, potato, cottonseed, and sugar apple, which makes hexacosanoic acid a potential biomarker for the consumption of these food products. Hexacosanoic acid can be found primarily in blood, as well as in human adrenal gland and fibroblasts tissues. Hexacosanoic acid exists in all eukaryotes, ranging from yeast to humans. In humans, hexacosanoic acid is involved in a couple of metabolic pathways, which include adrenoleukodystrophy, x-linked and beta oxidation of very long chain fatty acids. Hexacosanoic acid is also involved in carnitine-acylcarnitine translocase deficiency, which is a metabolic disorder. Moreover, hexacosanoic acid is found to be associated with adrenomyeloneuropathy, peroxisomal biogenesis defect, and adrenoleukodystrophy, neonatal. Hexacosanoic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Cerotic acid is also a type of very long chain fatty acid that is often associated with the disease adrenoleukodystrophy, which involves the excessive saturation of unmetabolized fatty acid chains, including cerotic acid, in the peroxisome. [In the chem box it is shown folded only because of lack of space. In fact, it is a straight-chain, saturated fatty acid.] . Treatment options for adrenoleukodystrophy (ALD) are limited. Dietary treatment is with Lorenzos oil. For the childhood cerebral form, stem cell transplant and gene therapy are options if the disease is detected early in the clinical course. Adrenal insufficiency in ALD patients can be successfully treated (T3DB). Hexacosanoic acid, or cerotic acid, is a 26-carbon long-chain saturated fatty acid with the chemical formula CH3(CH2)24COOH. It is most commonly found in beeswax and carnauba wax, and is a white crystalline solid. Cerotic acid is also a type of very long chain fatty acid that is often associated with the disease adrenoleukodystrophy, which involves the excessive saturation of unmetabolized fatty acid chains, including cerotic acid, in the peroxisome. Hexacosanoic acid, also known as C26:0 or N-hexacosanoate, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Hexacosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Hexacosanoic acid is a potentially toxic compound.

   

Hexadecenoic acid

2-hexadecenoic acid

C16H30O2 (254.224568)


A C16 straight-chain monounsaturated fatty acid having one C=C double bond.

   

Pentacosanoic acid

P-NITROPHENYLPHOSPHATETRISBUFFERSALT

C25H50O2 (382.38106)


Pentacosanoic acid, also known as pentacosanoate or hyenate, is a straight-chain saturated fatty acid and a very long-chain fatty acid. It is a conjugate acid of a pentacosanoate. Pentacosanoic acid belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Pentacosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Pentacosanoic acid is a potentially toxic compound. Pentacosanoic acid is a straight-chain saturated fatty acid and a very long-chain fatty acid. It is a conjugate acid of a pentacosanoate. Pentacosanoic acid is a natural product found in Staphisagria macrosperma, Rhizophora apiculata, and other organisms with data available. Isolated from Citrus bergamia (bergamot orange) Pentacosanoic acid is a 25-carbon long-chain saturated fatty acid. Pentacosanoic is a conjugate acid of a pentacosanoate[1]. Pentacosanoic acid is a 25-carbon long-chain saturated fatty acid. Pentacosanoic is a conjugate acid of a pentacosanoate[1].

   

Heneicosanoic acid

N-Heneicosanoic acid

C21H42O2 (326.3184632)


Henicosanoic acid, also known as N-heneicosanoate or 21:0,is a long-chain fatty acid that is henicosane in which one of the methyl groups has been oxidised to give the corresponding carboxylic acid. It is a straight-chain saturated fatty acid and a long-chain fatty acid. It is a conjugate acid of a henicosanoate. Heneicosanoic acid belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Heneicosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heneicosanoic acid is a potentially toxic compound. Isolated from olive oil (Olea europaea) Heneicosanoic acid is a long-chain saturated fatty acid which is found in plants and animals[1][2][3]. Heneicosanoic acid is a long-chain saturated fatty acid which is found in plants and animals[1][2][3].

   

Heptadecanoic acid

heptadecanoic acid

C17H34O2 (270.2558664)


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

   

Tricosanoic acid

Tricosanoic acid, aluminum salt

C23H46O2 (354.34976159999997)


Tricosanoic acid, also known as N-tricosanoate or 22FA, belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. Tricosanoic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Tricosanoic acid is a potentially toxic compound. Constituent of Citrus bergamia (bergamot orange) oil Tricosanoic acid is a long-chain fatty acid and shown to be a hair growth stimulant. Tricosanoic acid is a long-chain fatty acid and shown to be a hair growth stimulant.

   

Alloxanthin

4-[(3E,5E,7E,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 (564.3967092)


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.

   

Idoxanthin

3-[(1E,3Z,5Z,7Z,9E,11E,13Z,15Z,17E)-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-yl]-6-hydroxy-2,4,4-trimethylcyclohex-2-en-1-one

C40H54O4 (598.4021884)


Idoxanthin is found in common carp. Idoxanthin is isolated from Japanese sandfish and marine fish-eggs. Postulated metabolite produced of Astaxanthin LMC61-X in mackerel eggs. Isolated from Japanese sandfish and marine fish-eggs. Postulated metabolite production of Astaxanthin LMC61-X in mackerel eggs. Idoxanthin is found in common carp and fishes.

   

Manzamine A

25-{9H-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

C36H44N4O (548.3514934)


   

Eicosatetraenoic acid

icosa-2,4,6,8-tetraenoic acid

C20H32O2 (304.24021719999996)


   

Octadeca-2,4-dienoic acid

Octadeca-2,4-dienoic acid

C18H32O2 (280.2402172)


   

Sapienic acid

hexadec-6-enoic acid

C16H30O2 (254.224568)


   

Tricosanal

choline magnesium trisalicylate

C23H46O (338.3548466)


   

15-Docosenoic acid

docos-15-enoic acid

C22H42O2 (338.3184632)


15-docosenoic acid is a member of the class of compounds known as very long-chain fatty acids. Very long-chain fatty acids are fatty acids with an aliphatic tail that contains at least 22 carbon atoms. 15-docosenoic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). 15-docosenoic acid can be found in peanut, which makes 15-docosenoic acid a potential biomarker for the consumption of this food product.

   

C14:0

Tetradecanoic acid

C14H28O2 (228.20891880000002)


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

   

C17:0

HEPTADECANOIC ACID

C17H34O2 (270.2558664)


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

   
   

Palmitic Acid

n-Hexadecanoic acid

C16H32O2 (256.2402172)


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

   

VACCENIC ACID

trans-Vaccenic acid

C18H34O2 (282.2558664)


An octadecenoic acid having a double bond at position 11; and which can occur in cis- or trans- configurations. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

   
   

12-Methyltetradecanoic acid

12-Methyltetradecanoic acid

C15H30O2 (242.224568)


   

13-Methyltetradecanoic acid

13-Methyltetradecanoic acid

C15H30O2 (242.224568)


13-Methyltetradecanoic acid (13-MTD), a saturated branched-chain fatty acid with potent anticancer effects. 13-Methyltetradecanoic acid induces apoptosis in many types of human cancer cells[1][2]. 13-Methyltetradecanoic acid (13-MTD), a saturated branched-chain fatty acid with potent anticancer effects. 13-Methyltetradecanoic acid induces apoptosis in many types of human cancer cells[1][2].

   

9-Hexadecenoic acid

Hexadec-9-enoic acid

C16H30O2 (254.224568)


   

Astaxanthin

beta,beta-Carotene-4,4-dione, 3,3-dihydroxy-, (3S,3S)-

C40H52O4 (596.3865392)


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

   

8-Hydroxymanzamine A

8-Hydroxymanzamine A

C36H44N4O2 (564.3464084)


An alkaloid that is manzamine A with a hydroxy substituent at position 8. Isolated from Pachypellina and Acanthostrongylophora, it exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).

   
   
   

2-Hydroxytricosanoic acid

2-hydroxy Tricosanoic Acid

C23H46O3 (370.34467659999996)


A 2-hydroxy fatty acid that is tricosanoic acid substituted by a hydroxy group at position 2.

   
   
   

HEPTADEC-8-ENOIC ACID

HEPTADEC-8-ENOIC ACID

C17H32O2 (268.2402172)


   

1-(hydroxymethyl)-7-methoxy-6-methylisoquinoline-5,8-dione

1-(hydroxymethyl)-7-methoxy-6-methylisoquinoline-5,8-dione

C12H11NO4 (233.0688046)


   
   
   
   

Pregnenolone

3beta-hydroxypregn-5-en-20-one

C21H32O2 (316.24021719999996)


A 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20. C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Pregnenolone is a derivative of cholesterol, the product of Cytochrome P450 side-chain cleavage (EC 1.14.15.6, CYP11A1); this reaction consists of three consecutive monooxygenations; a 22-hydroxylation, 20-hydroxylation and the cleavage of the C20-C22 bond, yielding pregnenolone. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. This reaction occurs in steroid hormone-producing tissues such as the adrenal cortex, corpus luteum and placenta. The most notable difference between the placenta and other steroidogenic tissues is that electron supply to CYP11A1 limits the rate at which cholesterol is converted to pregnenolone in the placenta. The limiting component for electron delivery to CYP11A1 is the concentration of adrenodoxin reductase in the mitochondrial matrix which is insufficient to maintain the adrenodoxin pool in a fully reduced state. Pregnenolone is also a neurosteroid, and is produced in the spinal cord; CYP11A1 is the key enzyme catalyzing the conversion of cholesterol into pregnenolone, the rate-limiting step in the biosynthesis of all classes of steroids, and has been localized in sensory networks of the spinal cord dorsal horn. In the adrenal glomerulosa cell angiotensin II, one of the major physiological regulators of mineralocorticoid synthesis, appears to affect most of the cholesterol transfer to the mitochondrial outer membrane and transport to the inner membrane steps and thus to exerts a powerful control over the use of cholesterol for aldosterone production. (PMID: 17222962, 15823613, 16632873, 15134809) [HMDB]. Pregnenolone is found in many foods, some of which are common wheat, yellow bell pepper, oval-leaf huckleberry, and fenugreek. Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3]. Pregnenolone (3β-Hydroxy-5-pregnen-20-one) is a powerful neurosteroid, the main precursor of various steroid hormones including steroid ketones. Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors. Pregnenolone can protect the brain from cannabis intoxication[1][2]. Pregnenolone is also a TRPM3 channel activator, and also can weakly activate TRPM1 channels[3].

   

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.

   

Tryptamine

5-22-10-00045 (Beilstein Handbook Reference)

C10H12N2 (160.1000432)


   

Lignoceric acid

Tetracosanoic acid

C24H48O2 (368.36541079999995)


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

   

Myristic Acid

Tetradecanoic acid

C14H28O2 (228.20891880000002)


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

   

Behenic acid

Docosanoic acid

C22H44O2 (340.3341124)


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

   

Margaric acid

HEPTADECANOIC ACID

C17H34O2 (270.2558664)


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

   

TRICOSANOIC ACID

TRICOSANOIC ACID

C23H46O2 (354.34976159999997)


A very long-chain fatty acid that is tricosane in which one of the methyl groups has been oxidised to the corresponding carboxylic acid. Tricosanoic acid is a long-chain fatty acid and shown to be a hair growth stimulant. Tricosanoic acid is a long-chain fatty acid and shown to be a hair growth stimulant.

   

stearic acid

stearic acid

C18H36O2 (284.2715156)


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

   

Oleic acid

cis-9-Octadecenoic acid

C18H34O2 (282.2558664)


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

   

trans-Vaccenic acid

(11E)-octadec-11-enoic acid

C18H34O2 (282.2558664)


The trans- isomer of vaccenic acid. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

   

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.

   

Arachidic acid

Arachidic acid

C20H40O2 (312.302814)


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

   

Cerotic acid

HEXACOSANOIC ACID

C26H52O2 (396.3967092)


A 26-carbon, straight-chain, saturated fatty acid.

   

Pentacosylic acid

Pentacosanoic acid

C25H50O2 (382.38106)


Pentacosanoic acid is a 25-carbon long-chain saturated fatty acid. Pentacosanoic is a conjugate acid of a pentacosanoate[1]. Pentacosanoic acid is a 25-carbon long-chain saturated fatty acid. Pentacosanoic is a conjugate acid of a pentacosanoate[1].

   

Fucoxanthin

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

C42H58O6 (658.4233168000001)


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

   

HENEICOSANOIC ACID

HENEICOSANOIC ACID

C21H42O2 (326.3184632)


   

HEPTADECANOIC ACID

HEPTADECANOIC ACID

C17H34O2 (270.2558664)


   

Alloxanthin

4-[(3E,5E,7E,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 (564.3967092)


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.

   

HEXACOSANOIC ACID

HEXACOSANOIC ACID

C26H52O2 (396.3967092)


   

Hexadecanoic acid

Hexadecanoic acid

C16H32O2 (256.2402172)


   

Octadecanoic acid

Octadecanoic acid

C18H36O2 (284.2715156)


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

   
   

2-hydroxy behenic

2-hydroxy-docosanoic acid

C22H44O3 (356.3290274)


   

Idoxanthin

3-[(1E,3Z,5Z,7Z,9E,11E,13Z,15Z,17E)-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-yl]-6-hydroxy-2,4,4-trimethylcyclohex-2-en-1-one

C40H54O4 (598.4021884)


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

   

C22:0

Docosanoic acid

C22H44O2 (340.3341124)


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

   

C23:0

TRICOSANOIC ACID

C23H46O2 (354.34976159999997)


Tricosanoic acid is a long-chain fatty acid and shown to be a hair growth stimulant. Tricosanoic acid is a long-chain fatty acid and shown to be a hair growth stimulant.

   

C26:0

HEXACOSANOIC ACID

C26H52O2 (396.3967092)


   

FA 28:3

(11S)-10,11-methylene-5Z,9E-heptacosadienoic acid

C28H50O2 (418.38106)


   

canthaxanthin

canthaxanthin

C40H52O2 (564.3967092)


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

   

Tricosanal

Tricosanal

C23H46O (338.3548466)


D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D018501 - Antirheumatic Agents

   

2-Methyltetradecanoic acid

2-Methyltetradecanoic acid

C15H30O2 (242.224568)


   

143-25-9

(11E)-octadec-11-enoic acid

C18H34O2 (282.2558664)


trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level. trans-Vaccenic acid is a precursor for the synthesis of saturated fatty acid in the rumen and of conjugated linoleic acid (CLA) at the tissue level.

   

Liphagal

Liphagal

C22H28O4 (356.19874880000003)


A meroterpenoid isolated from the marine sponge Aka coralliphaga and has been shown to exhibit inhibitory activity against phosphatidylinositol-3-OH kinase.

   

6-hydroxymanzamine A

6-hydroxymanzamine A

C36H44N4O2 (564.3464084)


An alkaloid that is manzamine A with a hydroxy substituent at position 6. Isolated from Haliclona and Acanthostrongylophora, it exhibits inhibitory activity against Glycogen Synthase Kinase-3 (EC 2.7.11.26).

   
   

Hexadec-9-enoic acid

Hexadec-9-enoic acid

C16H30O2 (254.224568)


A hexadecenoic acid in which the double bond is located at position 9.

   

Hexadecenoate

Hexadecenoate

C16H29O2 (253.2167434)


A long-chain unsaturated fatty acid anion that is the conjugate base of hexadecenoic acid, obtained by deprotonation of the carboxy group; major species at pH 7.3.

   

Henicosanoic acid

Henicosanoic acid

C21H42O2 (326.3184632)


A long-chain fatty acid that is henicosane in which one of the methyl groups has been oxidised to give the corresponding carboxylic acid.

   

Icosanoic acid

Icosanoic acid

C20H40O2 (312.302814)


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

   

(4z,6z,8z,12r,13r,29s,31s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹³,³¹]tetratriaconta-4,6,8-trien-3-ol

(4z,6z,8z,12r,13r,29s,31s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹³,³¹]tetratriaconta-4,6,8-trien-3-ol

C32H54N2O (482.42359139999996)


   

(3r,4e)-16-methylicos-4-en-1-yn-3-ol

(3r,4e)-16-methylicos-4-en-1-yn-3-ol

C21H38O (306.2922498)


   

tricos-16-enoic acid

tricos-16-enoic acid

C23H44O2 (352.3341124)


   

methyl (2r)-2-methoxyhexadecanoate

methyl (2r)-2-methoxyhexadecanoate

C18H36O3 (300.26643060000004)


   

3-{8-[(3s,3as,6ar)-1-[(4z)-13-(pyridin-3-yl)tridec-4-en-1-yl]-hexahydrocyclopenta[c][1,2]oxazol-3-yl]octyl}pyridine

3-{8-[(3s,3as,6ar)-1-[(4z)-13-(pyridin-3-yl)tridec-4-en-1-yl]-hexahydrocyclopenta[c][1,2]oxazol-3-yl]octyl}pyridine

C37H57N3O (559.4501392)


   

(2s)-2-amino-n-[(1s,11s,14s,17s,20s,23s,33s)-23-benzyl-12,15,18-trihydroxy-14-methyl-17-(2-methylpropyl)-21,24-dioxo-2,13,16,19,22,25-hexaazaheptacyclo[18.11.1.1¹,²².1²,⁹.0³,⁸.0²⁶,³¹.0²⁵,³³]tetratriaconta-3,5,7,9(34),12,15,18,26,28,30-decaen-11-yl]-3-phenylpropanimidic acid

(2s)-2-amino-n-[(1s,11s,14s,17s,20s,23s,33s)-23-benzyl-12,15,18-trihydroxy-14-methyl-17-(2-methylpropyl)-21,24-dioxo-2,13,16,19,22,25-hexaazaheptacyclo[18.11.1.1¹,²².1²,⁹.0³,⁸.0²⁶,³¹.0²⁵,³³]tetratriaconta-3,5,7,9(34),12,15,18,26,28,30-decaen-11-yl]-3-phenylpropanimidic acid

C49H52N8O6 (848.4009612)


   

(3e)-docosa-3,15-dien-1-yne

(3e)-docosa-3,15-dien-1-yne

C22H38 (302.2973348)


   

1,18λ⁵-diazatricyclo[30.3.1.1¹⁴,¹⁸]heptatriaconta-14(37),15,17,32,34-pentaen-18-ylium-35-ide

1,18λ⁵-diazatricyclo[30.3.1.1¹⁴,¹⁸]heptatriaconta-14(37),15,17,32,34-pentaen-18-ylium-35-ide

C35H58N2 (506.4599748)


   

(4e,6z,19z,22z,29s,30r)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,6,12,14,19,22-hexaen-34-yl

(4e,6z,19z,22z,29s,30r)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,6,12,14,19,22-hexaen-34-yl

C32H47N2 (459.37390419999997)


   

(3z,5e,15e,24z)-20-[(1z)-but-1-en-1-yl]-17,18-dihydroxy-9-methoxy-3,6,19,24-tetramethyl-7-methylidene-21,26-dioxa-16-azabicyclo[13.10.3]octacosa-3,5,15(28),16,24-pentaene-22,27-dione

(3z,5e,15e,24z)-20-[(1z)-but-1-en-1-yl]-17,18-dihydroxy-9-methoxy-3,6,19,24-tetramethyl-7-methylidene-21,26-dioxa-16-azabicyclo[13.10.3]octacosa-3,5,15(28),16,24-pentaene-22,27-dione

C35H51NO7 (597.3665336)


   

hexacos-19-enoic acid

hexacos-19-enoic acid

C26H50O2 (394.38106)


   

11-amino-12,21,30,33-tetrahydroxy-38-[(4-hydroxyphenyl)methyl]-23-isopropyl-14,32-bis(sec-butyl)-2,13,16,22,25,31,34,37,40-nonaazanonacyclo[33.11.1.1¹,³⁷.1²,⁹.0³,⁸.0¹⁶,²⁰.0²⁵,²⁹.0⁴¹,⁴⁶.0⁴⁰,⁴⁸]nonatetraconta-3,5,7,9(49),12,21,30,33,41,43,45-undecaene-15,24,36,39-tetrone

11-amino-12,21,30,33-tetrahydroxy-38-[(4-hydroxyphenyl)methyl]-23-isopropyl-14,32-bis(sec-butyl)-2,13,16,22,25,31,34,37,40-nonaazanonacyclo[33.11.1.1¹,³⁷.1²,⁹.0³,⁸.0¹⁶,²⁰.0²⁵,²⁹.0⁴¹,⁴⁶.0⁴⁰,⁴⁸]nonatetraconta-3,5,7,9(49),12,21,30,33,41,43,45-undecaene-15,24,36,39-tetrone

C58H72N10O9 (1052.5483462)


   

7-amino-1,6-dimethylisoquinoline-5,8-dione

7-amino-1,6-dimethylisoquinoline-5,8-dione

C11H10N2O2 (202.07422400000002)


   

(4e,12r,14r,19z,22z,29r,30s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,19,22-triene

(4e,12r,14r,19z,22z,29r,30s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,19,22-triene

C32H54N2 (466.4286764)


   

(3r,13e,15z)-16-chlorohexadeca-13,15-dien-9,11-diyn-3-yl acetate

(3r,13e,15z)-16-chlorohexadeca-13,15-dien-9,11-diyn-3-yl acetate

C18H23ClO2 (306.1386488)


   

(7-methoxy-6-methyl-5,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate

(7-methoxy-6-methyl-5,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate

C17H17NO5 (315.1106672)


   

7-methylhexadec-6-enoic acid

7-methylhexadec-6-enoic acid

C17H32O2 (268.2402172)


   

(2e,4e,6e,8e,10e,12e,14e,16e,18e,20e,22e)-23-(4-hydroxy-2,3,3-trimethyl-6-oxocyclohex-1-en-1-yl)-4,8,12,17,21-pentamethyltricosa-2,4,6,8,10,12,14,16,18,20,22-undecaenal

(2e,4e,6e,8e,10e,12e,14e,16e,18e,20e,22e)-23-(4-hydroxy-2,3,3-trimethyl-6-oxocyclohex-1-en-1-yl)-4,8,12,17,21-pentamethyltricosa-2,4,6,8,10,12,14,16,18,20,22-undecaenal

C37H46O3 (538.3446766)


   

(3r,4e,6e,8z,12r,13r,29s,31s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹³,³¹]tetratriaconta-4,6,8-trien-3-ol

(3r,4e,6e,8z,12r,13r,29s,31s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹³,³¹]tetratriaconta-4,6,8-trien-3-ol

C32H54N2O (482.42359139999996)


   
   

(4e,6z,14r,18r,19z,21e,29s,30r)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,6,12,19,21-pentaen-18-ol

(4e,6z,14r,18r,19z,21e,29s,30r)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,6,12,19,21-pentaen-18-ol

C32H50N2O (478.392293)


   

methoxy[16-(pyridin-3-yl)hexadec-5-yn-1-yl]amine

methoxy[16-(pyridin-3-yl)hexadec-5-yn-1-yl]amine

C22H36N2O (344.2827486)


   

(1s,2r,4r,8e,10z,12e,15e,17r,18s)-5,20-diazapentacyclo[18.12.1.1¹,⁵.0²,¹⁸.0⁴,¹⁶]tetratriaconta-8,10,12,15-tetraen-17-ol

(1s,2r,4r,8e,10z,12e,15e,17r,18s)-5,20-diazapentacyclo[18.12.1.1¹,⁵.0²,¹⁸.0⁴,¹⁶]tetratriaconta-8,10,12,15-tetraen-17-ol

C32H50N2O (478.392293)


   

(1r,2r,8z,12r,13s,21e,26s,27s)-27-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]-25-oxa-3,16-diazapentacyclo[11.11.3.1¹²,¹⁶.0¹,²⁶.0²,¹²]octacosa-8,21-diene

(1r,2r,8z,12r,13s,21e,26s,27s)-27-[(1r)-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]-25-oxa-3,16-diazapentacyclo[11.11.3.1¹²,¹⁶.0¹,²⁶.0²,¹²]octacosa-8,21-diene

C36H50N4O (554.398441)


   

3-(12-{3-[8-(pyridin-3-yl)octyl]-hexahydrocyclopenta[c][1,2]oxazol-1-yl}dodecyl)pyridine

3-(12-{3-[8-(pyridin-3-yl)octyl]-hexahydrocyclopenta[c][1,2]oxazol-1-yl}dodecyl)pyridine

C36H57N3O (547.4501392)


   

(2r)-n-[(2s,3s,4r,6e)-1-{[(2r,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxyoctadec-6-en-2-yl]-2-hydroxydocosanimidic acid

(2r)-n-[(2s,3s,4r,6e)-1-{[(2r,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxyoctadec-6-en-2-yl]-2-hydroxydocosanimidic acid

C48H92N2O10 (856.6751612)


   

16-chlorohexadeca-13,15-dien-9,11-diyn-3-yl acetate

16-chlorohexadeca-13,15-dien-9,11-diyn-3-yl acetate

C18H23ClO2 (306.1386488)


   

(2s,7z,13e,15e)-16-chlorohexadeca-7,13,15-trien-9,11-diyn-2-ol

(2s,7z,13e,15e)-16-chlorohexadeca-7,13,15-trien-9,11-diyn-2-ol

C16H19ClO (262.1124354)


   

6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e,19e,21e,23e)-3,7,12,16,20-pentamethyl-25-oxohexacosa-1,3,5,7,9,11,13,15,17,19,21,23-dodecaen-1-yl]cyclohex-2-en-1-one

6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e,19e,21e,23e)-3,7,12,16,20-pentamethyl-25-oxohexacosa-1,3,5,7,9,11,13,15,17,19,21,23-dodecaen-1-yl]cyclohex-2-en-1-one

C40H50O3 (578.3759749999999)


   

tricos-17-enoic acid

tricos-17-enoic acid

C23H44O2 (352.3341124)


   

n-methyl-n-[14-(pyridin-3-yl)tetradec-9-yn-1-yl]hydroxylamine

n-methyl-n-[14-(pyridin-3-yl)tetradec-9-yn-1-yl]hydroxylamine

C20H32N2O (316.25145019999997)


   

(1s,2r,10z,16s,23z,27r)-5,18-diazapentacyclo[12.12.1.1¹,⁵.0²,¹⁶.0¹⁸,²⁷]octacosa-10,14,23-triene

(1s,2r,10z,16s,23z,27r)-5,18-diazapentacyclo[12.12.1.1¹,⁵.0²,¹⁶.0¹⁸,²⁷]octacosa-10,14,23-triene

C26H40N2 (380.319132)


   

(2z)-2-[(6e,10e)-13-(furan-3-yl)-2,6,10-trimethyltrideca-6,10-dien-1-ylidene]-5-hydroxy-4-methylfuran-3-one

(2z)-2-[(6e,10e)-13-(furan-3-yl)-2,6,10-trimethyltrideca-6,10-dien-1-ylidene]-5-hydroxy-4-methylfuran-3-one

C25H34O4 (398.24569640000004)


   

methoxy[16-(pyridin-3-yl)hexadec-7-yn-1-yl]amine

methoxy[16-(pyridin-3-yl)hexadec-7-yn-1-yl]amine

C22H36N2O (344.2827486)


   

(3r,4z,6z,8z,12r,13s,29s,31r)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹³,³¹]tetratriaconta-4,6,8-trien-3-ol

(3r,4z,6z,8z,12r,13s,29s,31r)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹³,³¹]tetratriaconta-4,6,8-trien-3-ol

C32H54N2O (482.42359139999996)


   

(1r,2r,4r,12r,13s,16e)-25-{3h,4h,9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

(1r,2r,4r,12r,13s,16e)-25-{3h,4h,9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

C36H46N4O (550.3671426)


   

(18,20,21-trihydroxy-3-{[hydroxy(methoxy)phosphoryl]oxy}-8,10,14-trimethyl-6-(3-methylbutan-2-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosan-17-yl)oxidanesulfonic acid

(18,20,21-trihydroxy-3-{[hydroxy(methoxy)phosphoryl]oxy}-8,10,14-trimethyl-6-(3-methylbutan-2-yl)-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosan-17-yl)oxidanesulfonic acid

C29H51O12PS (654.2838696)


   

(3s,7z,13e,15e)-16-chlorohexadeca-7,13,15-trien-9,11-diyn-3-ol

(3s,7z,13e,15e)-16-chlorohexadeca-7,13,15-trien-9,11-diyn-3-ol

C16H19ClO (262.1124354)


   

(1r,2r,8z,12r,13s,21z,26s,27r)-27-{9h-pyrido[3,4-b]indol-1-yl}-25-oxa-3,16-diazapentacyclo[11.11.3.1¹²,¹⁶.0¹,²⁶.0²,¹²]octacosa-8,21-diene

(1r,2r,8z,12r,13s,21z,26s,27r)-27-{9h-pyrido[3,4-b]indol-1-yl}-25-oxa-3,16-diazapentacyclo[11.11.3.1¹²,¹⁶.0¹,²⁶.0²,¹²]octacosa-8,21-diene

C36H46N4O (550.3671426)


   

1,16λ⁵-diazatricyclo[28.3.1.1¹²,¹⁶]pentatriaconta-12(35),13,15,30,32-pentaen-16-ylium-33-ide

1,16λ⁵-diazatricyclo[28.3.1.1¹²,¹⁶]pentatriaconta-12(35),13,15,30,32-pentaen-16-ylium-33-ide

C33H54N2 (478.4286764)


   
   

(1r,2r,4r,5z,12r,13s,16z)-13-hydroxy-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-triene-25-carbaldehyde

(1r,2r,4r,5z,12r,13s,16z)-13-hydroxy-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-triene-25-carbaldehyde

C26H38N2O2 (410.29331279999997)


   

(2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid

(2r)-n-[(2s,3s,4r,6e)-3,4-dihydroxy-1-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl]-2-hydroxydocosanimidic acid

C52H99NO15 (977.7014343999999)


   

(3r,13e,15z)-16-chlorohexadeca-13,15-dien-9,11-diyn-3-ol

(3r,13e,15z)-16-chlorohexadeca-13,15-dien-9,11-diyn-3-ol

C16H21ClO (264.1280846)


   

(3r,4e,15e)-docosa-4,15-dien-1-yn-3-ol

(3r,4e,15e)-docosa-4,15-dien-1-yn-3-ol

C22H38O (318.2922498)


   

heptacos-20-enoic acid

heptacos-20-enoic acid

C27H52O2 (408.3967092)


   

1,13,27,37-tetraazaoctacyclo[20.16.2.1⁹,¹³.0⁹,⁴⁰.0¹⁰,²⁴.0²⁵,³⁷.0²⁶,³⁴.0²⁸,³³]hentetraconta-5,18,26(34),28,30,32-hexaene-22,23-diol

1,13,27,37-tetraazaoctacyclo[20.16.2.1⁹,¹³.0⁹,⁴⁰.0¹⁰,²⁴.0²⁵,³⁷.0²⁶,³⁴.0²⁸,³³]hentetraconta-5,18,26(34),28,30,32-hexaene-22,23-diol

C37H52N4O2 (584.4090052)


   

2-amino-n-[23-benzyl-12,15,18-trihydroxy-14-methyl-17-(2-methylpropyl)-21,24-dioxo-2,13,16,19,22,25-hexaazaheptacyclo[18.11.1.1¹,²².1²,⁹.0³,⁸.0²⁶,³¹.0²⁵,³³]tetratriaconta-3,5,7,9(34),12,15,18,26,28,30-decaen-11-yl]-3-phenylpropanimidic acid

2-amino-n-[23-benzyl-12,15,18-trihydroxy-14-methyl-17-(2-methylpropyl)-21,24-dioxo-2,13,16,19,22,25-hexaazaheptacyclo[18.11.1.1¹,²².1²,⁹.0³,⁸.0²⁶,³¹.0²⁵,³³]tetratriaconta-3,5,7,9(34),12,15,18,26,28,30-decaen-11-yl]-3-phenylpropanimidic acid

C49H52N8O6 (848.4009612)


   

n-methyl-n-[13-(pyridin-3-yl)tridecyl]hydroxylamine

n-methyl-n-[13-(pyridin-3-yl)tridecyl]hydroxylamine

C19H34N2O (306.2670994)


   

3-{13-[(3s,3as,6ar)-3-[8-(pyridin-3-yl)octyl]-hexahydrocyclopenta[c][1,2]oxazol-1-yl]tridecyl}pyridine

3-{13-[(3s,3as,6ar)-3-[8-(pyridin-3-yl)octyl]-hexahydrocyclopenta[c][1,2]oxazol-1-yl]tridecyl}pyridine

C37H59N3O (561.4657884)


   

2-methoxyhexadec-5-enoic acid

2-methoxyhexadec-5-enoic acid

C17H32O3 (284.2351322)


   

(2s)-2-amino-n-[(1s,11s,14s,17s,20s,23s,33r)-23-benzyl-17-[(2s)-butan-2-yl]-12,15,18-trihydroxy-14-methyl-21,24-dioxo-2,13,16,19,22,25-hexaazaheptacyclo[18.11.1.1¹,²².1²,⁹.0³,⁸.0²⁶,³¹.0²⁵,³³]tetratriaconta-3,5,7,9(34),12,15,18,26,28,30-decaen-11-yl]-3-phenylpropanimidic acid

(2s)-2-amino-n-[(1s,11s,14s,17s,20s,23s,33r)-23-benzyl-17-[(2s)-butan-2-yl]-12,15,18-trihydroxy-14-methyl-21,24-dioxo-2,13,16,19,22,25-hexaazaheptacyclo[18.11.1.1¹,²².1²,⁹.0³,⁸.0²⁶,³¹.0²⁵,³³]tetratriaconta-3,5,7,9(34),12,15,18,26,28,30-decaen-11-yl]-3-phenylpropanimidic acid

C49H52N8O6 (848.4009612)


   

(5z)-9-[(1e,2s)-2-[(9z)-hexadec-9-en-1-yl]cyclopropylidene]non-5-enoic acid

(5z)-9-[(1e,2s)-2-[(9z)-hexadec-9-en-1-yl]cyclopropylidene]non-5-enoic acid

C28H48O2 (416.36541079999995)


   

3-[(7z)-10-(pyridin-3-yl)dec-7-en-1-yl]-1-[(9z)-11-(pyridin-3-yl)undec-9-en-1-yl]pyridin-1-ium

3-[(7z)-10-(pyridin-3-yl)dec-7-en-1-yl]-1-[(9z)-11-(pyridin-3-yl)undec-9-en-1-yl]pyridin-1-ium

[C36H50N3]+ (524.400452)


   

2-amino-3-{[2-(butanoyloxy)-3-(propanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid

2-amino-3-{[2-(butanoyloxy)-3-(propanoyloxy)propoxy(hydroxy)phosphoryl]oxy}propanoic acid

C13H24NO10P (385.1137774)


   

(5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid

(5z)-9-[(1e,2s)-2-hexadecylcyclopropylidene]non-5-enoic acid

C28H50O2 (418.38106)


   

(2e,4e,6e,8e,10e,12e,14e,16e,18e,20e,22z)-23-[(4r)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl]-4,8,12,17,21-pentamethyltricosa-2,4,6,8,10,12,14,16,18,20,22-undecaenal

(2e,4e,6e,8e,10e,12e,14e,16e,18e,20e,22z)-23-[(4r)-4-hydroxy-2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl]-4,8,12,17,21-pentamethyltricosa-2,4,6,8,10,12,14,16,18,20,22-undecaenal

C37H46O3 (538.3446766)


   

n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl)-2-hydroxydocosanimidic acid

n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}octadec-6-en-2-yl)-2-hydroxydocosanimidic acid

C52H99NO15 (977.7014343999999)


   

1-[(2s)-2,3-dihydroxypropoxy]octadec-6-en-5-one

1-[(2s)-2,3-dihydroxypropoxy]octadec-6-en-5-one

C21H40O4 (356.29264400000005)


   

n-methyl-n-[(9e)-16-(pyridin-3-yl)hexadec-9-en-11-yn-1-yl]hydroxylamine

n-methyl-n-[(9e)-16-(pyridin-3-yl)hexadec-9-en-11-yn-1-yl]hydroxylamine

C22H34N2O (342.2670994)


   

(2s,7z,13e,15z)-16-chlorohexadeca-7,13,15-trien-9,11-diyn-2-yl acetate

(2s,7z,13e,15z)-16-chlorohexadeca-7,13,15-trien-9,11-diyn-2-yl acetate

C18H21ClO2 (304.1229996)


   

n-[1-({6-[({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-3,4-dihydroxyoctadec-6-en-2-yl]-2-hydroxydocosanimidic acid

n-[1-({6-[({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-3,4-dihydroxyoctadec-6-en-2-yl]-2-hydroxydocosanimidic acid

C54H102N2O15 (1018.7279822)


   

(4z,12r,14r,19z,22z,29r,30s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,19,22-triene

(4z,12r,14r,19z,22z,29r,30s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,19,22-triene

C32H54N2 (466.4286764)


   

1,16λ⁵-diazatricyclo[29.3.1.1¹²,¹⁶]hexatriaconta-12(36),13,15,31,33-pentaen-16-ylium-34-ide

1,16λ⁵-diazatricyclo[29.3.1.1¹²,¹⁶]hexatriaconta-12(36),13,15,31,33-pentaen-16-ylium-34-ide

C34H56N2 (492.4443256)


   

(3r)-16-methylicos-1-yn-3-ol

(3r)-16-methylicos-1-yn-3-ol

C21H40O (308.307899)


   

(4z,18z)-29-oxa-10,24-diazahexacyclo[22.3.1.1¹²,¹⁵.0¹,¹¹.0³,¹⁰.0¹³,²⁷]nonacosa-4,12,14,18-tetraene

(4z,18z)-29-oxa-10,24-diazahexacyclo[22.3.1.1¹²,¹⁵.0¹,¹¹.0³,¹⁰.0¹³,²⁷]nonacosa-4,12,14,18-tetraene

C26H36N2O (392.2827486)


   
   

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

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

C29H48O (412.37049579999996)


   

(3s,7z,13z,15z)-16-chlorohexadeca-7,13,15-trien-9,11-diyn-3-ol

(3s,7z,13z,15z)-16-chlorohexadeca-7,13,15-trien-9,11-diyn-3-ol

C16H19ClO (262.1124354)


   

n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-6-en-2-yl)-2-hydroxydocosanimidic acid

n-(3,4-dihydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadec-6-en-2-yl)-2-hydroxydocosanimidic acid

C46H89NO10 (815.6486134)


   

[6-methyl-7-(methylamino)-5,8-dioxoisoquinolin-1-yl]methyl (2z)-2-methylbut-2-enoate

[6-methyl-7-(methylamino)-5,8-dioxoisoquinolin-1-yl]methyl (2z)-2-methylbut-2-enoate

C17H18N2O4 (314.1266508)


   

16-chlorohexadeca-7,13,15-trien-9,11-diyn-2-ol

16-chlorohexadeca-7,13,15-trien-9,11-diyn-2-ol

C16H19ClO (262.1124354)


   

(3r,4e)-19-methylicos-4-en-1-yn-3-ol

(3r,4e)-19-methylicos-4-en-1-yn-3-ol

C21H38O (306.2922498)


   

(1r,2r,4r,12r,13s,16e)-25-{6-hydroxy-3h,4h,9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

(1r,2r,4r,12r,13s,16e)-25-{6-hydroxy-3h,4h,9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

C36H46N4O2 (566.3620576)


   

(1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

(1r,2r,4r,5z,12r,13r,16z)-25-{9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

C36H44N4O (548.3514934)


   

(z)-methoxy[16-(pyridin-3-yl)hexadec-7-yn-1-ylidene]amine

(z)-methoxy[16-(pyridin-3-yl)hexadec-7-yn-1-ylidene]amine

C22H34N2O (342.2670994)


   

(z)-methoxy[14-(pyridin-3-yl)tetradec-11-yn-1-ylidene]amine

(z)-methoxy[14-(pyridin-3-yl)tetradec-11-yn-1-ylidene]amine

C20H30N2O (314.235801)


   

9-ethoxy-3,8-dimethylimidazo[4,3-a]isoquinoline-7,10-dione

9-ethoxy-3,8-dimethylimidazo[4,3-a]isoquinoline-7,10-dione

C15H14N2O3 (270.10043740000003)


   

methoxy[14-(pyridin-3-yl)tetradec-11-yn-1-yl]amine

methoxy[14-(pyridin-3-yl)tetradec-11-yn-1-yl]amine

C20H32N2O (316.25145019999997)


   

(1r,2r,4r,5z,12r,13s,16e)-25-{6-hydroxy-3h,4h,9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

(1r,2r,4r,5z,12r,13s,16e)-25-{6-hydroxy-3h,4h,9h-pyrido[3,4-b]indol-1-yl}-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-trien-13-ol

C36H46N4O2 (566.3620576)


   

(3z,5e,15e,24z)-17,18-dihydroxy-9-methoxy-3,6,19,24-tetramethyl-20-[(1z)-3-methylbut-1-en-1-yl]-7-methylidene-21,26-dioxa-16-azabicyclo[13.10.3]octacosa-3,5,15(28),16,24-pentaene-22,27-dione

(3z,5e,15e,24z)-17,18-dihydroxy-9-methoxy-3,6,19,24-tetramethyl-20-[(1z)-3-methylbut-1-en-1-yl]-7-methylidene-21,26-dioxa-16-azabicyclo[13.10.3]octacosa-3,5,15(28),16,24-pentaene-22,27-dione

C36H53NO7 (611.3821828)


   

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

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

C29H48O (412.37049579999996)


   

(3s,13e,15z)-16-chlorohexadeca-13,15-dien-9,11-diyn-3-ol

(3s,13e,15z)-16-chlorohexadeca-13,15-dien-9,11-diyn-3-ol

C16H21ClO (264.1280846)


   

3-[(7e)-10-(pyridin-3-yl)dec-7-en-1-yl]-1-[(8e)-10-(pyridin-3-yl)dec-8-en-1-yl]pyridin-1-ium

3-[(7e)-10-(pyridin-3-yl)dec-7-en-1-yl]-1-[(8e)-10-(pyridin-3-yl)dec-8-en-1-yl]pyridin-1-ium

[C35H48N3]+ (510.3848028)


   

(1s,11s,14s,17s,20s,23s,33r)-11-amino-23-benzyl-17-[(2r)-butan-2-yl]-12,15,18-trihydroxy-14-methyl-2,13,16,19,22,25-hexaazaheptacyclo[18.11.1.1¹,²².1²,⁹.0³,⁸.0²⁶,³¹.0²⁵,³³]tetratriaconta-3,5,7,9(34),12,15,18,26,28,30-decaene-21,24-dione

(1s,11s,14s,17s,20s,23s,33r)-11-amino-23-benzyl-17-[(2r)-butan-2-yl]-12,15,18-trihydroxy-14-methyl-2,13,16,19,22,25-hexaazaheptacyclo[18.11.1.1¹,²².1²,⁹.0³,⁸.0²⁶,³¹.0²⁵,³³]tetratriaconta-3,5,7,9(34),12,15,18,26,28,30-decaene-21,24-dione

C40H43N7O5 (701.3325507999999)


   

(5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate

(5-hydroxy-6-methyl-7,8-dioxoisoquinolin-1-yl)methyl (2z)-2-methylbut-2-enoate

C16H15NO5 (301.095018)


   

1-[(2s)-2,3-dihydroxypropoxy]octadec-4-en-6-one

1-[(2s)-2,3-dihydroxypropoxy]octadec-4-en-6-one

C21H40O4 (356.29264400000005)


   

(1r,11s,14r,20r,23r,26r,29s,32r,42r)-11-amino-14,32-dibenzyl-12,21,24,27-tetrahydroxy-23-[(4-hydroxyphenyl)methyl]-26-methyl-2,13,16,22,25,28,31,34-octaazaoctacyclo[27.11.1.1¹,³¹.1²,⁹.0³,⁸.0¹⁶,²⁰.0³⁵,⁴⁰.0³⁴,⁴²]tritetraconta-3,5,7,9(43),12,21,24,27,35,37,39-undecaene-15,30,33-trione

(1r,11s,14r,20r,23r,26r,29s,32r,42r)-11-amino-14,32-dibenzyl-12,21,24,27-tetrahydroxy-23-[(4-hydroxyphenyl)methyl]-26-methyl-2,13,16,22,25,28,31,34-octaazaoctacyclo[27.11.1.1¹,³¹.1²,⁹.0³,⁸.0¹⁶,²⁰.0³⁵,⁴⁰.0³⁴,⁴²]tritetraconta-3,5,7,9(43),12,21,24,27,35,37,39-undecaene-15,30,33-trione

C57H57N9O8 (995.4329882)


   

(4as,6as,11ar,11bs)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-1h,2h,3h,4ah,5h,6h,11h,11ah-cyclohexa[a]fluorene-9,10-diol

(4as,6as,11ar,11bs)-7-(methoxymethyl)-4,4,6a,11b-tetramethyl-1h,2h,3h,4ah,5h,6h,11h,11ah-cyclohexa[a]fluorene-9,10-diol

C23H34O3 (358.25078140000005)


   

(3r,4e)-14-methyldocos-4-en-1-yn-3-ol

(3r,4e)-14-methyldocos-4-en-1-yn-3-ol

C23H42O (334.3235482)


   
   

15,16-dihydroxy-2,6,6,10-tetramethyl-12-oxatetracyclo[9.7.0.0²,⁷.0¹³,¹⁸]octadeca-1(11),13,15,17-tetraene-14-carbaldehyde

15,16-dihydroxy-2,6,6,10-tetramethyl-12-oxatetracyclo[9.7.0.0²,⁷.0¹³,¹⁸]octadeca-1(11),13,15,17-tetraene-14-carbaldehyde

C22H28O4 (356.19874880000003)


   

1,17λ⁵-diazatricyclo[30.3.1.1¹³,¹⁷]heptatriaconta-13(37),14,16,32,34-pentaen-17-ylium-35-ide

1,17λ⁵-diazatricyclo[30.3.1.1¹³,¹⁷]heptatriaconta-13(37),14,16,32,34-pentaen-17-ylium-35-ide

C35H58N2 (506.4599748)


   

(1r,2r,4r,5z,13s,16z)-13-hydroxy-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-triene-25-carbaldehyde

(1r,2r,4r,5z,13s,16z)-13-hydroxy-11,22-diazapentacyclo[11.11.2.1²,²².0²,¹².0⁴,¹¹]heptacosa-5,16,25-triene-25-carbaldehyde

C26H38N2O2 (410.29331279999997)


   

6-imino-1,3-dimethyl-9h-purin-2-one

6-imino-1,3-dimethyl-9h-purin-2-one

C7H9N5O (179.0807064)


   

1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,19,22-triene

1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,19,22-triene

C32H54N2 (466.4286764)


   

(4z,6z,14s,19z,21z,29s,30s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,6,12,19,21-pentaene

(4z,6z,14s,19z,21z,29s,30s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,6,12,19,21-pentaene

C32H50N2 (462.397378)


   

hexacos-19-enal

hexacos-19-enal

C26H50O (378.386145)


   

7-ethoxy-2,6-dimethylisoquinoline-3,5,8-trione

7-ethoxy-2,6-dimethylisoquinoline-3,5,8-trione

C13H13NO4 (247.0844538)


   

(8z,10z,12e,15z,17r)-5,20-diazapentacyclo[18.12.1.1¹,⁵.0²,¹⁸.0⁴,¹⁶]tetratriaconta-8,10,12,15-tetraen-17-ol

(8z,10z,12e,15z,17r)-5,20-diazapentacyclo[18.12.1.1¹,⁵.0²,¹⁸.0⁴,¹⁶]tetratriaconta-8,10,12,15-tetraen-17-ol

C32H50N2O (478.392293)


   

(3z,5e,15z,24z)-20-[(1z)-but-1-en-1-yl]-17,18-dihydroxy-9-methoxy-3,6,19,24-tetramethyl-7-methylidene-21,26-dioxa-16-azabicyclo[13.10.3]octacosa-3,5,15(28),16,24-pentaene-22,27-dione

(3z,5e,15z,24z)-20-[(1z)-but-1-en-1-yl]-17,18-dihydroxy-9-methoxy-3,6,19,24-tetramethyl-7-methylidene-21,26-dioxa-16-azabicyclo[13.10.3]octacosa-3,5,15(28),16,24-pentaene-22,27-dione

C35H51NO7 (597.3665336)


   

[6-methyl-7-(methylamino)-5,8-dioxoisoquinolin-1-yl]methyl 2-methylbut-2-enoate

[6-methyl-7-(methylamino)-5,8-dioxoisoquinolin-1-yl]methyl 2-methylbut-2-enoate

C17H18N2O4 (314.1266508)


   

2-[(8-hydroxy-7-methylpurin-6-yl)amino]ethanesulfonic acid

2-[(8-hydroxy-7-methylpurin-6-yl)amino]ethanesulfonic acid

C8H11N5O4S (273.0531726)


   
   

docos-17-enoic acid

docos-17-enoic acid

C22H42O2 (338.3184632)


   

(4z,14r,19z,21z,29r,30s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,19,21-trien-18-ol

(4z,14r,19z,21z,29r,30s)-1,16-diazatetracyclo[27.3.1.1¹²,¹⁶.0¹⁴,³⁰]tetratriaconta-4,19,21-trien-18-ol

C32H54N2O (482.42359139999996)


   
   

n-[1-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-3,4-dihydroxyoctadec-6-en-2-yl]-2-hydroxydocosanimidic acid

n-[1-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-3,4-dihydroxyoctadec-6-en-2-yl]-2-hydroxydocosanimidic acid

C48H92N2O10 (856.6751612)


   

(1r,2r,14z,21r,22r,27e,29z,31s)-18,24-diazapentacyclo[16.14.1.1³,²².0¹,²¹.0²,²⁴]tetratriaconta-3(34),14,27,29-tetraen-31-ol

(1r,2r,14z,21r,22r,27e,29z,31s)-18,24-diazapentacyclo[16.14.1.1³,²².0¹,²¹.0²,²⁴]tetratriaconta-3(34),14,27,29-tetraen-31-ol

C32H50N2O (478.392293)


   

tetracos-17-enal

tetracos-17-enal

C24H46O (350.3548466)