NCBI Taxonomy: 1779162
Suberitida (ncbi_taxid: 1779162)
found 500 associated metabolites at order taxonomy rank level.
Ancestor: Heteroscleromorpha
Child Taxonomies: Suberitidae, Halichondriidae, Stylocordylidae, unclassified Suberitida, Suberitida incertae sedis
Myristic acid
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
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
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
alpha-Carotene
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
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
Eicosapentaenoic acid
Icosapent, also known as icosapentaenoate or (5z,8z,11z,14z,17z)-eicosapentaenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, icosapent is considered to be a fatty acid lipid molecule. Icosapent is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Icosapent can be found in a number of food items such as barley, sacred lotus, white lupine, and rape, which makes icosapent a potential biomarker for the consumption of these food products. Icosapent can be found primarily in blood, feces, sweat, and urine, as well as throughout most human tissues. In humans, icosapent is involved in the alpha linolenic acid and linoleic acid metabolism. Moreover, icosapent is found to be associated with essential hypertension and hypertension. Ethyl eicosapentaenoic acid (E-EPA, icosapent ethyl) is a derivative of the omega-3 fatty acid eicosapentaenoic acid (EPA) that is used in combination with changes in diet to lower triglyceride levels in adults with severe (≥ 500 mg/dL) hypertriglyceridemia. This was the second class of fish oil-based drug to be approved for use as a drug and was approved by the FDA in 2012. These fish oil drugs are similar to fish oil dietary supplements but the ingredients are better controlled and have been tested in clinical trials . The anti-inflammatory, antithrombotic and immunomodulatory actions of EPA is probably due to its role in eicosanoid physiology and biochemistry. Most eicosanoids are produced by the metabolism of omega-3 fatty acids, specifically, arachidonic acid. These eicosanoids, leukotriene B4 (LTB4) and thromboxane A2 (TXA2) stimulate leukocyte chemotaxis, platelet aggregation and vasoconstriction. They are thrombogenic and artherogenic. On the other hand, EPA is metabolized to leukotriene B5 (LTB5) and thromboxane A3 (TXA3), which are eicosanoids that promote vasodilation, inhibit platelet aggregation and leukocyte chemotaxis and are anti-artherogenic and anti-thrombotic. The triglyceride-lowering effect of EPA results from inhibition of lipogenesis and stimulation of fatty acid oxidation. Fatty acid oxidation of EPA occurs mainly in the mitochondria. EPA is a substrate for Prostaglandin-endoperoxide synthase 1 and 2. It also appears to affect the function and bind to the Carbohydrate responsive element binding protein (ChREBP) and to a fatty acid receptor (G-coupled receptor) known as GP40 (DrugBank). Eicosapentaenoic acid (EPA or also icosapentaenoic acid) is an important polyunsaturated fatty acid found in fish oils. It serves as the precursor for the prostaglandin-3 and thromboxane-3 families. A diet rich in eicosapentaenoic acid lowers serum lipid concentration, reduces incidence of cardiovascular disorders, prevents platelet aggregation, and inhibits arachidonic acid conversion into the thromboxane-2 and prostaglandin-2 families. Eicosapentaenoic acid is an omega-3 fatty acid. In physiological literature, it is given the name 20:5(n-3). Its systematic chemical name is all-cis-5,8,11,14,17-icosapentaenoic acid. It also has the trivial name timnodonic acid. Chemically, EPA is a carboxylic acid with a 20-carbon chain and five cis double bonds; the first double bond is located at the third carbon from the omega end. Because of the presence of double bonds, EPS is a polyunsaturated fatty acid. Metabolically it acts as a precursor for prostaglandin-3 (which inhibits platelet aggregation), thromboxane-3, and leukotriene-5 groups. It is found in fish oils of cod liver, herring, mackerel, salmon, menhaden, and sardine. It is also found in human breast milk (Wikipedia). Chemical was purchased from CAY 90110 (Lot. 0443819-6); Diagnostic ions: 301.2, 257.1, 202.9 CONFIDENCE standard compound; INTERNAL_ID 305 Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3]. Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3].
Stearic acid
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.
Palmitoleic acid
Cis-9-palmitoleic acid, also known as palmitoleate or (Z)-9-hexadecenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, cis-9-palmitoleic acid is considered to be a fatty acid lipid molecule. Cis-9-palmitoleic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-9-palmitoleic acid can be found in a number of food items such as mixed nuts, carrot, hedge mustard, and chanterelle, which makes cis-9-palmitoleic acid a potential biomarker for the consumption of these food products. Cis-9-palmitoleic acid can be found primarily in most biofluids, including urine, blood, saliva, and feces, as well as in human adipose tissue, prostate and skeletal muscle tissues. Cis-9-palmitoleic acid exists in all living species, ranging from bacteria to humans. Moreover, cis-9-palmitoleic acid is found to be associated with isovaleric acidemia. Palmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. Present in all tissues, it is generally found in higher concentrations in the liver. Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40\\\\\% respectively. Palmitoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Palmitoleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=373-49-9 (retrieved 2024-07-15) (CAS RN: 373-49-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats. Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.
Arachidate (20:0)
Arachidic acid, also known as icosanoic acid, is a saturated fatty acid with a 20-carbon chain. It is a minor constituent of butter, perilla oil, peanut oil, corn oil, and cocoa butter. It also constitutes 7.08\\\\% of the fats from the fruit of the durian species Durio graveolens. The salts and esters of arachidic acid are known as arachidates. Its name derives from the Latin arachis that means peanut. It can be formed by the hydrogenation of arachidonic acid. The reduction of arachidic acid yields arachidyl alcohol. Arachidic acid is used for the production of detergents, photographic materials and lubricants. Arachidic 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. Arachidic acid is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 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].
3-Methyladenine
3-Methyladenine, also known as 3-ma nucleobase, belongs to the class of organic compounds known as 6-aminopurines. These are purines that carry an amino group at position 6. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring. 3-Methyladenine exists in all living species, ranging from bacteria to humans. 3-Methyladenine has been detected, but not quantified, in several different foods, such as soft-necked garlics, chinese bayberries, burbots, amaranths, and tea. This could make 3-methyladenine a potential biomarker for the consumption of these foods. 3-Methyladenine is one of the purines damaged by alkylation and oxidation which can be recognized and excised by the human 3-methyladenine DNA glycosylase (AAG) (EC: EC3.2.2.21). 3-Methyladenine is one of the purines damaged by alkylation and oxidation which can be recognized and excised by the human 3-methyladenine DNA glycosylase (AAG) (EC: EC 3.2.2.21) [HMDB]. 3-Methyladenine is found in many foods, some of which are sacred lotus, evergreen huckleberry, swamp cabbage, and red rice. Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID M030
Retinal
A carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration. [HMDB]. Retinal is found in many foods, some of which are flaxseed, pepper (c. baccatum), climbing bean, and other soy product. Retinal is a carotenoid constituent of visual pigments. It is the oxidized form of retinol which functions as the active component of the visual cycle. It is bound to the protein opsin forming the complex rhodopsin. When stimulated by visible light, the retinal component of the rhodopsin complex undergoes isomerization at the 11-position of the double bond to the cis-form; this is reversed in "dark" reactions to return to the native trans-configuration. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids CONFIDENCE standard compound; INTERNAL_ID 142
Oleic acid
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].
Pentadecanoic acid
Pentadecanoic acid, also known as pentadecylic acid or C15:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Pentadecanoic acid (its ester is called pentadecanoate) is a saturated fatty acid that has 15 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. Pentadecanoic acid is found in plants and ruminants. Many "odd" length long-chain fatty acids, such as pentadecanoic acid, are derived from the consumption of cattle fats (milk and meat). Pentadecanoic acid constitutes 1.05\\\\% of milk fat and 0.43\\\\% of ruminant meat fat. The content of pentadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID: 9701185; PMID: 11238766). A fatty acid of exogenous (primarily ruminant) origin. Many "odd" length long chain amino acids are derived from the consumption of dairy fats (milk and meat). Pentadecanoic acid constitutes 1.05\\\\% of milk fat and 0.43\\\\% of ruminant meat fat. The content of heptadecanoic acid in the subcutaneous adipose tissue of humans appears to be a good biological marker of long-term milk fat intake in free-living individuals in populations with high consumption of dairy products. (PMID 9701185; PMID 11238766). Pentadecanoic acid is found in many foods, some of which are common bean, coriander, pepper (c. annuum), and hamburger. CONFIDENCE standard compound; INTERNAL_ID 248 Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone.
Lignoceric acid (C24)
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].
2-Hydroxymyristic acid
2-Hydroxymyristic acid is an analog of myristic acid that becomes metabolically activated in cells to form 2-hydroxymyristoyl-CoA, a potent inhibitor of myristoyl-CoA:protein N-myristoyltransferase, the enzyme that catalyzes protein N-myristoylation. Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck. (PMID 8103677) [HMDB] 2-Hydroxymyristic acid is an analog of myristic acid that becomes metabolically activated in cells to form 2-hydroxymyristoyl-CoA, a potent inhibitor of myristoyl-CoA:protein N-myristoyltransferase, the enzyme that catalyzes protein N-myristoylation. Treatment of T cells with 2-hydroxymyristic acid inhibits the myristoylation and alters the stability of p56lck. (PMID 8103677).
Vaccenic acid
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.
Cholesterol
Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50\\\\% of the lipid in the membrane or 60-80\\\\% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with c... Constituent either free or as esters, of fish liver oils, lard, dairy fats, egg yolk and bran Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].
Brassicasterol
Brassicasterol belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, brassicasterol is considered to be a sterol lipid molecule. Brassicasterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Brassicasterol is a potential CSF biomarker for Alzheimer’s disease (PMID: 21585343). C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Constituent of Brassica rapa oil Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].
Lathosterol
Lathosterol is a a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID: 8777839). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O [HMDB] Lathosterol is a a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues, and transported in the blood plasma of all animals. It is used as an indicator of whole-body cholesterol synthesis (PMID 14511438). Plasma lathosterol levels are significantly elevated in patients with bile acid malabsorption (PMID:8777839). Lathosterol oxidase (EC 1.14.21.6) is an enzyme that catalyzes the chemical reaction 5alpha-cholest-7-en-3beta-ol + NAD(P)H + H+ + O2 cholesta-5,7-dien-3beta-ol + NAD(P)+ + 2 H2O. Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis. Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis.
Okadaic acid
Okadaic acid is found in mollusks. Okadaic acid is found in the marine sponges Halichondria okadai and Halichondria melanodocia and shellfish. It is a metabolite of Prorocentrum lima. It is a diarrhetic shellfish toxin. Okadaic acid is a toxin that accumulates in bivalves and causes diarrhetic shellfish poisoning. The molecular formula of okadaic acid, which is a derivative of a C38 fatty acid, is C44H68O13. The IUPAC name of okadaic acid is (2R)-2-hydroxy-3-{(2S,5R,6R,8S)-5-hydroxy-[(1R,2E)-3-((2R,5R,6S,8R,8aS)-8-hydroxy-6-{(1S,3S)-1-hydroxy-3-[(3R,6S)-3-methyl-1,7-dioxaspiro[5.5]undec-2-yl]butyl}-7-methyleneoctahydro-3H,3H-spiro[furan-2,2-pyrano[3,2-b]pyran]-5-yl)-1-methylprop-2-en-1-yl]-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl}-2-methylpropanoic acid. Okadaic acid was named from the marine sponge Halichondria okadai, from which okadaic acid was isolated for the first time. It has also been isolated from another marine sponge, H. malanodocia, as a cytotoxin. The real producer of okadaic acid is a marine dinoflagellate D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins D009676 - Noxae > D002273 - Carcinogens D049990 - Membrane Transport Modulators D004791 - Enzyme Inhibitors D007476 - Ionophores
Fucosterol
Characteristic sterol of seaweeds; isolated from bladderwrack Fucus vesiculosus. Fucosterol is found in lemon grass and coconut. Fucosterol is found in coconut. Characteristic sterol of seaweeds; isolated from bladderwrack Fucus vesiculosu Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1]. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].
Nonadecanoic acid
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].
halichondrin B
D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
Halistanol sulfate
C29H52O12S3 (688.2620751999999)
Cerebronic acid
Constituent of various glycosphingolipids of wheat, corn and other plant subspecies Cerebronic acid is found in peanut and cereals and cereal products. D-Cerebronic acid is found in mushrooms. D-Cerebronic acid is isolated from Polyporus umbellatus (zhu ling).
Hexacosanoic acid
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.
Pentacosanoic acid
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].
Heptadecanoic acid
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, 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.
Isopalmitic acid
Isopalmitic acid is found in milk and milk products. Isopalmitic acid occurs in butterfa Occurs in butterfat. Isopalmitic acid is found in milk and milk products.
Cholesteryl acetate
Cholesteryl acetate is a normal human cholesteryl ester present in diverse fluids and organs. Cholesteryl acetate is also present in foods. Food oxidation affects the quality and safety of the human diet by generating compounds with biological activities that can adversely affect health. In particular the susceptibility of cholesterol to oxidation is well known; certain products of cholesterol oxidation have been reported to produce cytotoxic, angiotoxic and carcinogenic effects. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 10918380, 16458590, 9420339, 3343104, 6721900, 7278520).
15-Methylpalmitate
15-Methylpalmitate, also known as 15-methylhexadecanoate, is a fatty acid methyl ester (FAME). It has an exact mass of 269.25 g/mol and the molecular formula is C17H33O2. Methylpalmitate is a biomarker for the consumption of butte
3-hydroxypentadecanoic acid
3-Hydroxypentadecanoic acid is a long-chain hydroxy fatty acid. In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation.
Halichondrin B
D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents
alpha-Amorphene
Alpha-amorphene, also known as alpha-amorphene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Alpha-amorphene can be found in a number of food items such as pepper (spice), peppermint, sweet basil, and sweet bay, which makes alpha-amorphene a potential biomarker for the consumption of these food products. Alpha-amorphene, also known as α-amorphene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Alpha-amorphene can be found in a number of food items such as pepper (spice), peppermint, sweet basil, and sweet bay, which makes alpha-amorphene a potential biomarker for the consumption of these food products.
C14:0
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 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].
Aaptamine
Aaptamine is a natural product found in Aaptos, Aaptos aaptos, and other organisms with data available.
Aristolone
Aristolone is a natural product found in Litophyton erectum, Aristolochia clematitis, and other organisms with data available. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1]. Aristolone is a sesquiterpene isolated from Aristolochia debilis[1].
(5E)-5-[(6-bromo-1H-indol-3-yl)methylidene]-2-imino-1,3-dimethylimidazolidin-4-one
Palmitic Acid
COVID info from WikiPathways D004791 - Enzyme Inhibitors Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
VACCENIC ACID
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.
13-Methyltetradecanoic acid
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].
3-HYDROXYMYRISTIC ACID
A 3-hydroxy fatty acid that is tetradecanoic (myristic) acid substituted at position 3 by a hydroxy group
sitosterol
A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].
Fucosterol
A 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol can be found in horseradish tree and sunflower, which makes (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol a potential biomarker for the consumption of these food products. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1]. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].
2-hydroxypentadecanoic acid
A 2-hydroxy fatty acid that is pentadecanoic acid substituted by a hydroxy group at position 2.
18-Methylnonadecanoic acid
A methyl-branched fatty acid that is nonadecanoic acid substituted by a methyl group at position 18.
2-Hydroxyheptadecanoic acid
A 2-hydroxy fatty acid that is heptadecanoic acid (margaric acid) substituted by a hydroxy group at position 2.
9(11)-dehydroaxinysterol
A 3beta-sterol having a 5alpha-ergostane skeleton with double bonds at C-6, C-9(11), C-22 and C-25 and a peroxy group between positions 5 and 8. An antineoplastic agent isolated from Okinawan sponge of the genus Axinyssa.
2-Hydroxytricosanoic acid
A 2-hydroxy fatty acid that is tricosanoic acid substituted by a hydroxy group at position 2.
22-methyltetracosanoic acid
A methyl-branched fatty acid that is tetracosanoic acid (lignoceric acid) substituted by a methyl group at position 22.
okadaic acid
D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins D009676 - Noxae > D002273 - Carcinogens D049990 - Membrane Transport Modulators D004791 - Enzyme Inhibitors D007476 - Ionophores A polycyclic ether that is produced by several species of dinoflagellates, and is known to accumulate in both marine sponges and shellfish. A polyketide, polyether derivative of a C38 fatty acid, it is one of the primary causes of diarrhetic shellfish poisoning (DSP). It is a potent inhibitor of specific protein phosphatases and is known to have a variety of negative effects on cells.
Cholesterol
A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group. Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].
2-hydroxypentacosanoic acid
A 2-hydroxy fatty acid that is pentacosanoic acid substituted by a hydroxy group at position 2.
Brassicasterol
An 3beta-sterol that is (22E)-ergosta-5,22-diene substituted by a hydroxy group at position 3beta. It is a phytosterol found in marine algae, fish, and rapeseed oil. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3]. Brassicasterol is a metabolite of Ergosterol and has cardiovascular protective effects. Brassicasterol exerts anticancer effects in prostate cancer through dual targeting of AKT and androgen receptor signaling pathways. Brassicasterol inhibits HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis. Brassicasterol also inhibits sterol δ 24-reductase, slowing the progression of atherosclerosis. Brassicasterol is also a cerebrospinal fluid biomarker for Alzheimer's disease[1][2][3][4][5][6]. Brassicasterol, a metabolite of Ergosterol, plays a role in the inhibitory effect on bladder carcinogenesis promotion via androgen signaling[1]. Brassicasterol shows dual anti-infective properties against HSV-1 (IC50=1.2 μM) and Mycobacterium tuberculosis, and cardiovascular protective effect[2]. Brassicasterol exerts an anti-cancer effect by dual-targeting AKT and androgen receptor signaling in prostate cancer[3].
β-Carotene
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.
3-methyladenine
A methyladenine that is adenine substituted with a methyl group at position N-3.
Lignoceric acid
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].
PENTADECANOIC ACID
A straight-chain saturated fatty acid containing fifteen-carbon atoms. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone. Pentadecylic acid is a saturated fatty acid with a 15-carbon backbone.
Myristic Acid
Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.
Margaric acid
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
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 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
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
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
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.
Eicosapentaenoic acid
Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3]. Eicosapentaenoic Acid (EPA) is an orally active Omega-3 long-chain polyunsaturated fatty acid (ω-3 LC-PUFA). Eicosapentaenoic Acid exhibits a DNA demethylating action that promotes the re-expression of the tumor suppressor gene CCAAT/enhancer-binding protein δ (C/EBPδ). Eicosapentaenoic Acid activates RAS/ERK/C/EBPβ pathway through H-Ras intron 1 CpG island demethylation in U937 leukemia cells. Eicosapentaenoic Acid can promote relaxation of vascular smooth muscle cells and vasodilation[1][2][3].
Arachidic acid
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].
Pentacosylic acid
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].
Octadecanoic acid
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.
14-methyl Palmitic Acid
A methyl-branched fatty acid that is hexadecanoic acid (palmitic acid) substituted by a methyl group at position 14.
2-Hydroxymyristic acid
A derivative of myristic acid having a hydroxy substituent at C-2.
C20:0
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].
C23:0
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.
Lathosterol
Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis. Lathosterol is a cholesterol-like molecule. Serum Lathosterol concentration is an indicator of whole-body cholesterol synthesis.
tubercidin
An N-glycosylpyrrolopyrimidine that is adenosine in which the in the 5-membered ring that is not attached to the ribose moiety is replaced by a carbon. Tubercidin is produced in the culture broth of Streptomyces tubericidus. C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite D009676 - Noxae > D000963 - Antimetabolites D000970 - Antineoplastic Agents Tubercidin (7-Deazaadenosine) is an antibiotic obtained from Streptomyces tubercidicus. Tubercidin inhibits the growth of Streptococcus faecalis (8043) with an IC50 of 0.02 μM[1]. Tubercidin inhibits polymerases by incorporating DNA or RNA, thereby inhibiting DNA replication, RNA and protein synthesis[2]. Tubercidin is a weak inhibitor of adenosine phosphorylase, and interferes with the phosphorylation of adenosine and AMP[1]. Tubercidin has antiviral activity[2]. Tubercidin (7-Deazaadenosine) is an antibiotic obtained from Streptomyces tubercidicus. Tubercidin inhibits the growth of Streptococcus faecalis (8043) with an IC50 of 0.02 μM[1]. Tubercidin inhibits polymerases by incorporating DNA or RNA, thereby inhibiting DNA replication, RNA and protein synthesis[2]. Tubercidin is a weak inhibitor of adenosine phosphorylase, and interferes with the phosphorylation of adenosine and AMP[1]. Tubercidin has antiviral activity[2].
Hamacanthin B
An optically active form of hamacanthin A having S-configuration. It is an antifungal drug isolated from deep water marine sponge Hamacantha sp.
2-Hydroxyoctacosanoic acid
A 2-hydroxy fatty acid that is the 2-hydroxy derivative of octacosanoic acid.
WLN: QV19
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].
Crodacid
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.
AI3-36481
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].
143-25-9
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.
Cholesteryl acetate
A cholesterol ester obtained by formal acylation of the hydroxy group of cholesterol by acetic acid. Cholesteryl acetate is a normal human cholesteryl ester present in diverse fluids and organs. Cholesteryl acetate is also present in foods. Food oxidation affects the quality and safety of the human diet by generating compounds with biological activities that can adversely affect health. In particular the susceptibility of cholesterol to oxidation is well known; certain products of cholesterol oxidation have been reported to produce cytotoxic, angiotoxic and carcinogenic effects. Cholesteryl ester (CE) is the major transport and storage form of cholesterol in lipoprotein particles and most cell types. Molecular composition of CE species is of high interest for arteriosclerosis research, i.e., as components of lipoprotein subclasses or in studies investigating the mechanisms involved in the generation of lipid laden foam cells. Thus, it has been shown that CE species in circulating plasma are strongly correlated with development of coronary heart disease. This may be related to specific CE species profiles generated by enzymes involved in lipoprotein metabolism like lecithin:cholesterol acyltransferase (EC 2.3.1.43, LCAT), acyl-coenzyme A:cholesterol acyltransferase 2 (EC 2.3.1.26, ACAT2) or cholesteryl ester transfer protein (CETP). The cholesteryl ester transfer protein has a key role in the metabolism of high-density lipoprotein (HDL), mediating the exchange of lipids between lipoproteins, resulting in the net transfer of cholesteryl ester from HDL to other lipoproteins and in the subsequent uptake of cholesterol by hepatocytes. By increasing the cholesteryl ester content of low-density and very-low-density lipoproteins, CETP promotes the atherogenicity of these lipoproteins. In addition, high plasma concentrations of CETP are associated with reduced concentrations of HDL cholesterol. (PMID: 10918380, 16458590, 9420339, 3343104, 6721900, 7278520) [HMDB]
alpha-Amorphene
Alpha-amorphene, also known as alpha-amorphene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Alpha-amorphene can be found in a number of food items such as pepper (spice), peppermint, sweet basil, and sweet bay, which makes alpha-amorphene a potential biomarker for the consumption of these food products. Alpha-amorphene, also known as α-amorphene, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Alpha-amorphene can be found in a number of food items such as pepper (spice), peppermint, sweet basil, and sweet bay, which makes alpha-amorphene a potential biomarker for the consumption of these food products.
Cerebronic acid
A very long-chain hydroxy fatty acid composed of lignoceric acid having a 2-hydroxy substituent.
Coprostanol
A member of the class of phytosterols that is 5beta-cholestane carrying a hydroxy substituent at the 3beta-position.
Hexadec-9-enoic acid
A hexadecenoic acid in which the double bond is located at position 9.
14-Methylpentadecanoic acid
A methyl-branched fatty acid that is pentadecanoic acid substituted by a methyl group at position 14. It is a biomarker for rheumatoid arthritis.
Dihydrocholesterol
5α-Cholestan-3β-ol is a derivitized steroid compound. 5α-Cholestan-3β-ol is a derivitized steroid compound.
16-methyloctadecanoic acid
A methyl-branched fatty acid that is octadecanoic acid substituted by a methyl group at position 16.
18-methylicosanoic acid
A methyl-branched fatty acid that is arachidic acid substituted by a methyl group at position 18.
Hexadecenoate
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.
hamacanthin A
A member of the class of pyrazinones that is 5,6-dihydropyrazin-2(1H)-one substituted at positions 3 and 6 by 6-bromo-1H-indol-3-yl groups. It is an antifungal drug isolated from deep water marine sponge Hamacantha sp.
Halistanol sulfonic acid G
A steroid sulfate that is 5alpha-ergostane substituted by sulfate groups at positions 2, 3 and 6 (the (2beta,3alpha,6alpha stereoisomer).
Icosanoic acid
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.
2-hydroxycerotic acid
A very long-chain fatty acid that is cerotic (hexacosanoic) acid substituted at position 2 by a hydroxy group.
(2r)-n-{[(2r,3r,4s,6s)-3,4-dihydroxy-6-(hydroxymethyl)-5,5-dimethyloxan-2-yl]methyl}-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid
(1r,4r,4ar,6s)-4-isopropyl-6-isothiocyanato-1,6-dimethyl-2,3,4,4a,5,7-hexahydro-1h-naphthalene
(3z,5e,7s,10e)-7-ethoxy-3,7,11,15-tetramethylhexadeca-1,3,5,10,14-pentaene
7-isopropyl-2-isothiocyanato-2,10-dimethylspiro[4.5]dec-6-ene
(2s,5r,10s)-7-isopropyl-2-isothiocyanato-2,10-dimethylspiro[4.5]dec-6-ene
(5s)-5-methoxy-5-[(11e)-tetradeca-2,5,8,11-tetraen-1-yl]furan-2-one
(6e,10r,11e,13z)-10-ethoxy-2,6,10,14-tetramethylhexadeca-2,6,11,13,15-pentaen-4-one
(1s,2r,5r,6r,9r,10r,13s,15s)-6,10-dimethyl-5-[(2r,4s,5r)-4,5,6-trimethylheptan-2-yl]-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol
(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5s)-5-ethyl-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
(1r,3as,3bs,4r,7s,9ar,9bs,11ar)-1-[(2r)-5-tert-butyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol
7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene
(1as,4r,7s,7as,7br)-4-hydroperoxy-1,1,7,7a-tetramethyl-1ah,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalen-2-one
3-[(3s,9s,12s,15s,18s,21s,24s)-9,18-dibenzyl-11,14,17,20,23-pentahydroxy-21-(c-hydroxycarbonimidoylmethyl)-15-isopropyl-2,8-dioxo-1,7,10,13,16,19,22-heptaazatricyclo[22.3.0.0³,⁷]heptacosa-10,13,16,19,22-pentaen-12-yl]propanoic acid
(1s,2s,4ar,8as)-1-isothiocyanato-4a-methyl-8-methylidene-2-(prop-1-en-2-yl)-octahydronaphthalene
(2e,4e,6r)-n-[(1s,2s,3s,5s,9r)-1,7-dichloro-2,5-dihydroxy-9-methoxy-8-oxobicyclo[3.3.1]non-6-en-3-yl]-4,6-dimethyldodeca-2,4-dienimidic acid
C24H35Cl2NO5 (487.18921600000004)
(1ar,2s,7s,7as,7br)-1,1,2,7,7a-pentamethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene
(1s,7s,10s,16s,19s,22s,25s,28s)-19,22,25-tris[(2s)-butan-2-yl]-8,17,20,23,26-pentahydroxy-10-[(1r)-1-hydroxyethyl]-28-(2-methylpropyl)-3,9,12,18,21,24,27,30-octaazatetracyclo[28.3.0.0³,⁷.0¹²,¹⁶]tritriaconta-8,17,20,23,26-pentaene-2,11,29-trione
(5e)-2-imino-5-(1h-indol-3-ylmethylidene)-3-methylimidazolidin-4-one
C13H12N4O (240.10110619999998)
2,12-dimethoxy-7,11-diazatricyclo[6.4.1.0⁴,¹³]trideca-1,3,5,8(13),9,11-hexaene
2-(ethylimino)-5-(1h-indol-3-ylmethylidene)-1,3-dimethylimidazolidin-4-one
4-(5-{18-[5-(4-hydroxy-2-methylbut-2-en-1-yl)-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl}-4,6,6-trimethylcyclohex-3-en-1-yl)-3-methylbut-2-en-1-ol
(3s,6r,12s,14e,16r,18s)-6-[(3-chloro-4-hydroxyphenyl)methyl]-5,11-dihydroxy-3,7,12,14,16,18-hexamethyl-1-oxa-4,7,10-triazacyclooctadeca-4,10,14-triene-2,8-dione
(2r,4as,4br,8as,9r,10as)-2-hydroxy-4b,8,8,10a-tetramethyl-2-[(1s)-4-methyl-5-oxocyclohex-3-en-1-yl]-decahydrophenanthren-9-yl acetate
(5r)-3-(6-bromo-1h-indol-3-yl)-5-(1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one
(2r)-n-[(2s,3s,4r)-1-{[(2r,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-15-methylhexadecan-2-yl]-2-hydroxytricosanimidic acid
(3r,4s)-1,4-dimethyl-4-[(1e)-4-[(1r)-4-methylcyclohex-3-en-1-yl]penta-1,3-dien-1-yl]-3-{2-[(1r)-4-methylcyclohex-3-en-1-yl]prop-1-en-1-yl}cyclohex-1-ene
(1s,2s,5s,6s,9r,11s)-2-(2-hydroxypropan-2-yl)-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol
C16H25NO4S (327.15042100000005)
(1r,3as,3br,5as,7s,9as,9bs,11ar)-1-[(2r,5r)-5,6-dimethylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate
(3s,6s,9s,15s,18s,21s,24s)-3-benzyl-15,21-bis[(2s)-butan-2-yl]-5,8,17,20,23-pentahydroxy-18-(hydroxymethyl)-6-(2-methylpropyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione
C40H61N7O8 (767.4581386000001)
2-methyl-5-[(2e)-6-methylhepta-2,5-dien-2-yl]benzene-1,4-diol
7,8-bis(acetyloxy)-1-(5-isopropyl-6-methylheptan-2-yl)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-5-yl acetate
n-{7,9-dibromo-10-hydroxy-2-methoxy-8-oxo-1-oxaspiro[4.5]dec-6-en-3-yl}-4,6-dimethyldodeca-2,4-dienimidic acid
C24H35Br2NO5 (575.0881820000001)
(1s,2s,4r,12s,13r,15r,16s)-2-bromo-8-[(2r,3s)-1,1-dichloro-3-hydroxy-3-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]propan-2-yl]-16-hydroxy-9,13-dimethyl-18-oxapentacyclo[13.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰]octadeca-5(10),6,8-triene-11,17-dione
3-formyl-4-[3-(3-hydroxy-4-methylphenyl)-3-oxopropyl]-3,4a,8,8-tetramethyl-hexahydro-1h-naphthalen-1-yl acetate
n-{1,7-dichloro-2,5-dihydroxy-9-methoxy-8-oxobicyclo[3.3.1]non-6-en-3-yl}-4,6-dimethyldodeca-2,4-dienimidic acid
C24H35Cl2NO5 (487.18921600000004)
(3s,6r,9s,12s,14e,16r,18s)-5,11-dihydroxy-6-[(4-hydroxy-3-iodophenyl)methyl]-3-[(1r)-1-hydroxyethyl]-7,9,12,14,16,18-hexamethyl-1-oxa-4,7,10-triazacyclooctadeca-4,10,14-triene-2,8-dione
C29H42IN3O7 (671.2067372000001)
(2e,4e,6r)-n-[(1r,2s,4r,6s,7s,8s,10s)-6-chloro-1,7,10-trihydroxy-5-oxo-3-oxatricyclo[4.3.1.0²,⁴]decan-8-yl]-4,6-dimethyldodeca-2,4-dienimidic acid
C23H34ClNO6 (455.2074534000001)
2,6-diazatricyclo[7.3.1.0⁵,¹³]trideca-1(12),3,5(13),6,8,10-hexaene-11,12-diol
(6z,9s)-9-[(1e)-2-[(2r,3s)-3-[(2z)-oct-2-en-1-yl]oxiran-2-yl]ethenyl]-4,5,8,9-tetrahydro-3h-oxonin-2-one
n-(2-hydroxy-4,5,6,7-tetrahydro-3h-azepin-3-yl)-2-(n-methyloctanamido)-3-phenylpropanimidic acid
(2e,4e,6r)-n-[(1s,2r,3s,5s,9s)-1,7-dichloro-2,5-dihydroxy-9-methoxy-8-oxobicyclo[3.3.1]non-6-en-3-yl]-4,6-dimethyldodeca-2,4-dienimidic acid
C24H35Cl2NO5 (487.18921600000004)
1-(5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate
(2r)-n-[(3r)-2-hydroxy-3,4,5,6-tetrahydropyridin-3-yl]-2-(n-methyldec-9-enamido)-3-phenylpropanimidic acid
3-{1,4-dihydroxy-7-oxo-3h,6h,9h,10h,11h,11ah-pyrrolo[1,2-a][1,4,7]triazonin-3-yl}propanoic acid
(2r)-n-[(2s,3r,4r)-1-{[(2r,3r,4s,5r,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-15-methylhexadecan-2-yl]-2-hydroxydocosanimidic acid
(2z,5e)-5-(1h-indol-3-ylmethylidene)-1,3-dimethyl-2-(methylimino)imidazolidin-4-one
(2e,4e,6r)-n-[(2r,3s,5r,9r,10s)-7,9-dibromo-10-hydroxy-2-methoxy-8-oxo-1-oxaspiro[4.5]dec-6-en-3-yl]-4,6-dimethyldodeca-2,4-dienimidic acid
C24H35Br2NO5 (575.0881820000001)
(5r)-5-methoxy-5-(tetradeca-2,5,8,11-tetraen-1-yl)furan-2-one
2-bromo-4-[(4e)-5-hydroxy-2-imino-3h-imidazol-4-ylidene]-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one
(2s)-n-[(1s)-1-{[(3r,9r,12s,15s,16r)-9-benzyl-5,8,11-trihydroxy-12-[2-(c-hydroxycarbonimidoyl)ethyl]-3-(c-hydroxycarbonimidoylmethyl)-13,16-dimethyl-2,14-dioxo-1-oxa-4,7,10,13-tetraazacyclohexadeca-4,7,10-trien-15-yl]-c-hydroxycarbonimidoyl}-2-sulfoethyl]-2-{[(2r)-2-{[(2s)-2-{[(2r)-2-({[(2s)-1-[(2s)-3-(4-bromophenyl)-2-{[(2r)-1-hydroxy-2-[(hydroxymethylidene)amino]propylidene]amino}propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-5-carbamimidamidopentanimidic acid
C73H100BrN19O20S (1673.6295740000003)
10-{[2-(4-hydroxyphenyl)ethyl]imino}-7-methyl-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),3,8-trien-11-one
C19H19N3O2 (321.14771939999997)
n-[(2s,3s,4r)-1-{[(2s,3s,4r,5r,6s)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-16-methylheptadecan-2-yl]docosanimidic acid
2-methoxy-3,5-dimethyl-6-(5-methyl-6-oxoheptyl)pyran-4-one
(2s)-n-[(2r,3s,4s)-1-{[(2r,3r,4r,5s,6s)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-14-methylpentadecan-2-yl]-2-hydroxydocosanimidic acid
C46H90N2O10 (830.6595120000001)
(1r,5as,7s,9as,9bs,11ar)-1-[(2r)-5-ethyl-6-methylheptan-2-yl]-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol
n-[1-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-3,4-dihydroxy-15-methylhexadecan-2-yl]-2-hydroxytricosanimidic acid
2',6-dimethyl-3,5'-bis(6-methylhept-5-en-2-yl)-[1,1'-biphenyl]-2,4'-diol
7-isopropyl-4-isothiocyanato-1,4-dimethyl-2,3,3a,5,6,8a-hexahydro-1h-azulene
2-hydroxy-3-(5-hydroxy-8-{4-[8'-hydroxy-6'-(1-hydroxy-3-{3-methyl-1,7-dioxaspiro[5.5]undecan-2-yl}butyl)-7'-methylidene-hexahydrospiro[oxolane-2,2'-pyrano[3,2-b]pyran]-5-yl]but-3-en-2-yl}-10-methyl-1,7-dioxaspiro[5.5]undec-10-en-2-yl)-2-methylpropanoic acid
6-bromo-3-[(4r)-2-(6-bromo-1h-indole-3-carbonyl)-4,5-dihydro-1h-imidazol-4-yl]-1h-indole
1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol
2-methoxy-3,5-dimethyl-6-[(5r)-5-methyl-6-oxoheptyl]pyran-4-one
(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5s)-5-tert-butyl-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
3-[2-(6-bromo-1h-indole-3-carbonyl)-4,5-dihydro-1h-imidazol-4-yl]-1h-indole
(2r)-n-[(2s,3s,4r)-1-{[(2r,3r,4s,5r,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-14-methylpentadecan-2-yl]-2-hydroxytricosanimidic acid
(2e,4e,6r)-n-[(2s,3s,4ar,8s,8as)-6,8-dichloro-4a-hydroxy-2-methoxy-7-oxo-3,4,8,8a-tetrahydro-2h-1-benzopyran-3-yl]-4,6-dimethyldodeca-2,4-dienimidic acid
C24H35Cl2NO5 (487.18921600000004)
(1s,1''s,2's,3r,3''s,3'as,6''s,7r,7's,7'as,9s,9''s,11r,12''s,13s,14''r,16''r,18''s,20''s,22''r,26''r,28''s,29''s,30''r,34''r,37''s,39''r,40''s,41''r,43''r,44''s)-5-(1,2-dihydroxyethyl)-7',13,14'',29''-tetramethyl-8'',15''-dimethylidene-tetrahydro-3'h-dispiro[2,6,10-trioxatricyclo[7.4.0.0³,⁷]tridecane-11,5'-furo[3,2-b]pyran-2',24''-[2,19,23,27,31,38,42,45,47,48,49]undecaoxundecacyclo[32.9.2.1³,⁴⁰.1³,⁴¹.1⁶,⁹.1¹²,¹⁶.0¹⁸,³⁰.0²⁰,²⁸.0²²,²⁶.0³⁷,⁴⁴.0³⁹,⁴³]nonatetracontan]-32''-one
(3s,6s,12s,15s,21s,24s,27s)-21-benzyl-24-[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-isopropyl-3-(2-methylpropyl)-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione
(1s,3as,8ar)-1-(2-hydroxy-6-methylhept-5-en-2-yl)-3a,6-dimethyl-1,2,3,4,8,8a-hexahydroazulen-5-one
2-{[(5z)-5-{3-[(4,5-dibromo-1h-pyrrol-2-yl)formamido]-2-hydroxypropylidene}-2-iminoimidazolidin-4-ylidene]amino}ethanesulfonic acid
n-[(1z)-2-[(4as,6s,8ar)-6-chloro-5,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethenyl]-1-chloromethanecarbonimidoyl chloride
C16H22Cl3N (333.08177420000004)
(1s,2s,4ar,8as)-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-amine
1-(5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate
(4r)-1-methyl-4-[(2e,4e)-6-methylhepta-2,4,6-trien-2-yl]cyclohex-1-ene
2-[(3r,6s,9r,15s,18r,21s,24s)-21-benzyl-5,8,17,20,23-pentahydroxy-6,15,18-triisopropyl-2,14-dioxo-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaen-3-yl]ethanimidic acid
(1r,3ar,7s,9as,11ar)-7-hydroxy-9a,11a-dimethyl-1-[(2s,3e,5s)-5-methylhept-3-en-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-4-one
(3s,6s,12s,15s,21s,24s)-21-benzyl-3,24-bis[(2s)-butan-2-yl]-5,14,23,26-tetrahydroxy-12-[(4-hydroxyphenyl)methyl]-1,4,10,13,19,22,25-heptaazatetracyclo[25.3.0.0⁶,¹⁰.0¹⁵,¹⁹]triaconta-4,13,22,25-tetraene-2,11,20-trione
C45H61N7O8 (827.4581386000001)
(1r,2r,4as,8ar)-2-isopropyl-1-isothiocyanato-4a-methyl-8-methylidene-octahydronaphthalene
9-bromo-2,7-diazatricyclo[6.3.1.0⁴,¹²]dodeca-1(12),3,8-triene-10,11-dione
6-bromo-3-[4-(1h-indol-3-yl)-3h-imidazol-2-yl]-1h-indole
(1s,2r,5r,6r,9r,10r,13s,15s)-6,10-dimethyl-5-[(2r,5r)-5-[(1r,2r)-2-methylcyclopropyl]hexan-2-yl]-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol
3-[5-(3,6-dioxocyclohexa-1,4-dien-1-yl)-3-methylpent-3-en-1-yl]-6-hydroxy-2,4-dimethylbenzaldehyde
(1ar,4r,4ar,7r,7ar,7bs)-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulen-4-amine
(1r,3as,3bs,4r,7s,9ar,9bs,11ar)-1-[(2r,3e)-5-tert-butyl-6-methylhepta-3,6-dien-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol
11-methoxy-2,6-diazatricyclo[7.3.1.0⁵,¹³]trideca-1(13),2,4,6,8,10-hexaen-12-one
(3s,6s,9s,15s,18s,21s,24s)-3,18-dibenzyl-6,21-bis[(2r)-butan-2-yl]-5,8,17,20,23-pentahydroxy-15-(hydroxymethyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione
C43H59N7O8 (801.4424894000001)
n-{2-[(2s,4ar,8s)-4a,8-dimethyl-3,4,5,6,7,8-hexahydro-2h-naphthalen-2-yl]propan-2-yl}carboximidic acid
(1r,3as,3bs,4s,7s,9ar,9bs,11ar)-1-[(2r,3e)-5-isopropyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol
1-isothiocyanato-1,4a-dimethyl-7-(prop-1-en-2-yl)-octahydronaphthalene
[(1r,3as,3bs,5s,5as,7s,8s,9ar,9bs,11ar)-9a,11a-dimethyl-7,8-bis(sulfooxy)-1-[(2r,4e)-5,6,6,7-tetramethyloct-4-en-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-5-yl]oxidanesulfonic acid
(1s,8ar)-4-isopropyl-1-isothiocyanato-1,6-dimethyl-3,7,8,8a-tetrahydro-2h-naphthalene
(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5r)-5-ethyl-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
(1r,3as,3bs,7s,9ar,9bs,11ar)-7-hydroxy-1-[(2s,3e)-5-isopropyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one
[(3s,6r,9r,15s,18r,21s,24s)-15-[(2s)-butan-2-yl]-5,8,17,20,23-pentahydroxy-6-[(4-hydroxyphenyl)methyl]-18-methyl-21-(2-methylpropyl)-2,14-dioxo-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaen-3-yl]acetic acid
(3s,6s,12s,15s,21s,24s,30s,33s,36s,39s)-21,36-dibenzyl-5,14,23,32,35,38-hexahydroxy-3-[(1r)-1-hydroxyethyl]-12-[(4-hydroxyphenyl)methyl]-30,33-bis(2-methylpropyl)-1,4,10,13,19,22,28,31,34,37-decaazapentacyclo[37.3.0.0⁶,¹⁰.0¹⁵,¹⁹.0²⁴,²⁸]dotetraconta-4,13,22,31,34,37-hexaene-2,11,20,29-tetrone
4-isothiocyanato-1,1,4,7-tetramethyl-octahydro-1ah-cyclopropa[e]azulene
n-[(2s,3s,4r)-1-{[(2r,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-16-methylheptadecan-2-yl]docosanimidic acid
6,6'-dimethyl-3,3'-bis[(2s)-6-methylhept-5-en-2-yl]-[1,1'-biphenyl]-2,2'-diol
2-bromo-8-[1,1-dichloro-3-hydroxy-3-(4-methyl-5-oxooxolan-2-yl)propan-2-yl]-18-hydroxy-9,13-dimethyl-17,19-dioxapentacyclo[13.3.1.0¹,¹³.0⁴,¹².0⁵,¹⁰]nonadeca-5(10),6,8-trien-11-one
6-(2-hydroxy-4-methylphenyl)-2-methylheptane-2,3-diol
7-[(3-bromo-4-hydroxyphenyl)methyl]-6,12-dihydroxy-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadeca-5,11,15-triene-2,9-dione
C34H44BrN3O7 (685.2362453999999)
n-[(1s,2s,4ar,8as)-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalen-1-yl]methoxycarboximidic acid
1-(5-ethyl-5,6-dimethylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
2-bromo-4-[(4z)-2,5-dihydroxyimidazol-4-ylidene]-1h,5h,6h,7h-pyrrolo[2,3-c]azepin-8-one
5-(1h-indol-3-ylmethylidene)-1,3-dimethyl-2-(methylimino)imidazolidin-4-one
(1r,3ar,3bs,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r)-6-methyl-5-methylideneheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol
5-[(6-bromo-1h-indol-3-yl)methylidene]imidazole-2,4-diol
(2r,3s,5e,8s)-10-{[(1e,5s,6s,8r,9r,13r,14s,16e)-8,14-dimethoxy-1-{4-[4-(methoxycarbonyl)-1,3-oxazol-2-yl]-1,3-oxazol-2-yl}-5,9,13-trimethyl-17-(n-methylformamido)-12-oxoheptadeca-1,16-dien-6-yl]oxy}-8-hydroxy-2-methoxy-3-methyl-4,10-dioxodec-5-enimidic acid
(3s,6s,9s,15s,18s,21s,24s)-3,18-dibenzyl-6,21-bis[(2s)-butan-2-yl]-5,8,17,20,23-pentahydroxy-15-(hydroxymethyl)-1,4,7,13,16,19,22-heptaazatricyclo[22.3.0.0⁹,¹³]heptacosa-4,7,16,19,22-pentaene-2,14-dione
C43H59N7O8 (801.4424894000001)
(1r,4r)-1-methyl-4-[(2z,4e)-6-methylhepta-2,4-dien-2-yl]cyclohexane-1-carbonitrile
(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e)-5-isopropyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
(1'r,4r,5s,5's,14's,15's,16's,18's)-15'-(aminomethyl)-16'-chloro-5-hydroxy-2,3'-diimino-2',4',6',12'-tetraazaspiro[imidazolidine-4,17'-pentacyclo[10.6.0.0¹,⁵.0⁶,¹⁰.0¹⁴,¹⁸]octadecane]-7',9'-dien-11'-one
(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-isopropyl-6-methylhepta-3,6-dien-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
(3r,6s,12s,15r,18s,24s,27s,30r)-5,14,17,26,29-pentahydroxy-12-[(1r)-1-hydroxyethyl]-27-(1h-indol-3-ylmethyl)-24-isopropyl-3,15-bis(2-methylpropyl)-1,4,10,13,16,22,25,28-octaazatetracyclo[28.3.0.0⁶,¹⁰.0¹⁸,²²]tritriaconta-4,13,16,25,28-pentaene-2,11,23-trione
(5r)-5-(6-bromo-1h-indol-3-yl)-3-(1h-indol-3-yl)-5,6-dihydro-1h-pyrazin-2-one
(2e,4e,6r)-n-[(2r,3s,5r,6s,7r,9s,10s)-7,9-dibromo-6,10-dihydroxy-2-methoxy-8-oxo-1-oxaspiro[4.5]decan-3-yl]-4,6-dimethyldodeca-2,4-dienimidic acid
8-isothiocyanato-4a,8-dimethyl-2-(prop-1-en-2-yl)-hexahydro-1h-naphthalen-2-ol
(3s,6r,12s,14e,16r,18s)-5,11-dihydroxy-6-[(4-hydroxy-3-iodophenyl)methyl]-3-[(1r)-1-hydroxyethyl]-7,12,14,16,18-pentamethyl-1-oxa-4,7,10-triazacyclooctadeca-4,10,14-triene-2,8-dione
(3r,3ar,5r,8s,11br)-3-[(2s,3e,5s)-5,6-dimethylhept-3-en-2-yl]-3a,6-dimethyl-1h,2h,3h,4h,5h,7h,8h,9h,10h,11bh-cyclopenta[a]anthracene-5,8-diol
7-isothiocyanato-1,1,3a,7-tetramethyl-octahydrocyclopropa[a]naphthalene
1,5,5-trimethyl-6-[(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
(1s,2s,4ar,8as)-1-isocyano-2-isopropyl-4a-methyl-8-methylidene-octahydronaphthalene
1-(5-isopropyl-6-methylheptan-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
5,11-dihydroxy-6-[(4-hydroxy-3-iodophenyl)methyl]-3-(1-hydroxyethyl)-9-(hydroxymethyl)-7,12,14,16,18-pentamethyl-1-oxa-4,7,10-triazacyclooctadeca-4,10,14-triene-2,8-dione
C29H42IN3O8 (687.2016522000001)
(6z,9s)-9-[(1e)-2-[(2r,3s)-3-[(2z,5z)-octa-2,5-dien-1-yl]oxiran-2-yl]ethenyl]-4,5,8,9-tetrahydro-3h-oxonin-2-one
(1s,2s,4r,12s,13r,15r,18r)-2-bromo-8-[(2r,3s)-1,1-dichloro-3-hydroxy-3-[(2r,4r)-4-methyl-5-oxooxolan-2-yl]propan-2-yl]-18-hydroxy-9,13-dimethyl-17,19-dioxapentacyclo[13.3.1.0¹,¹³.0⁴,¹².0⁵,¹⁰]nonadeca-5(10),6,8-trien-11-one
(18z,29e)-tritriaconta-18,29-dien-2,4,20,32-tetrayne-1,6,31-triol
(2e,4e,6r)-n-[(2r)-3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]-4,6-dimethyldodeca-2,4-dienimidic acid
C24H35NO4 (401.25659500000006)
(6z,9s)-9-[(1e,3r,4s,6z)-3,4-dihydroxydodeca-1,6-dien-1-yl]-4,5,8,9-tetrahydro-3h-oxonin-2-one
(1s,4s,4as,8ar)-4-isopropyl-1-isothiocyanato-1,6-dimethyl-3,4,4a,7,8,8a-hexahydro-2h-naphthalene
n-[(1s,2r,3r,5s,6r,8r)-5-isopropyl-2,8-dimethyltricyclo[4.3.1.0³,⁸]decan-2-yl]carboximidic acid
n-[(1e)-11-[(24e)-16-hydroxy-10-methoxy-11,21-dimethyl-12,18-dioxo-3,7,19,27-tetraoxa-29,30,31-triazatetracyclo[24.2.1.1²,⁵.1⁶,⁹]hentriaconta-1(28),2(31),4,6(30),8,24,26(29)-heptaen-20-yl]-4,10-dimethoxy-5,9-dimethyl-6-oxoundec-1-en-1-yl]-n-methylformamide
(3s,6s,12s,15s,18s,21s,24s)-15-benzyl-3,18-bis[(2s)-butan-2-yl]-5,14,17,20,23-pentahydroxy-12-(hydroxymethyl)-21-(2-methylpropyl)-1,4,10,13,16,19,22-heptaazatricyclo[22.3.0.0⁶,¹⁰]heptacosa-4,13,16,19,22-pentaene-2,11-dione
C40H61N7O8 (767.4581386000001)
n-[1-({4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl}oxy)-3,4-dihydroxy-17-methyloctadecan-2-yl]tricosanimidic acid
C50H98N2O9 (870.7271938000001)
(2r,5s,7r,9s,10s,12r,15r,16r)-15-[(2s,3e,5s)-5,6-dimethylhept-3-en-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-1(11)-ene-5,10-diol
(1s,2r,5s,7r,9s,10s,15r,16r)-15-[(2s,3e,5s)-5,6-dimethylhept-3-en-2-yl]-2,16-dimethyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-11-ene-5,10-diol
5-methyl-4-{5-methyl-2-[(2s)-6-methylhept-5-en-2-yl]phenoxy}-2-[(2s)-6-methylhept-5-en-2-yl]phenol
(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate
3-[(3r,6s,12s,15s)-12-(2-carboxyethyl)-5,14-dihydroxy-2,11-dioxo-1,4,10,13-tetraazatricyclo[13.3.0.0⁶,¹⁰]octadeca-4,13-dien-3-yl]propanoic acid
3-[(3s,11as)-1,4-dihydroxy-7-oxo-3h,6h,9h,10h,11h,11ah-pyrrolo[1,2-a][1,4,7]triazonin-3-yl]propanoic acid
3-[5-(2,5-dihydroxyphenyl)-3-methylpent-3-en-1-yl]-5,6-dihydroxy-2,4-dimethylbenzaldehyde
15-benzyl-5,14,17,20,23-pentahydroxy-18-(hydroxymethyl)-3-(1h-indol-2-ylmethyl)-12-isopropyl-21-(sec-butyl)-1,4,10,13,16,19,22-heptaazatricyclo[22.3.0.0⁶,¹⁰]heptacosa-4,13,16,19,22-pentaene-2,11-dione
6,9,9,12b-tetramethyl-5,6,7,8,8a,10,11,12-octahydro-oxatetraphen-3-ol
1-[1-({7-isopropyl-2,10-dimethylspiro[4.5]dec-1-en-6-yl}-c-hydroxycarbonimidoyl)-1-methylethyl]-5-oxopyrrolidine-2-carboxylic acid
(1z,5e,7r,9r,10s,13r,14r,16z,18e,24s,25s)-2,20,24,27-tetrahydroxy-10-methyl-21,26-diazatetracyclo[23.2.1.0⁷,¹⁴.0⁹,¹³]octacosa-1,5,11,16,18,20,26-heptaen-28-one
C27H34N2O5 (466.24675940000003)
1-(5-ethyl-5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
(4as,4br,8as,9r,10ar)-2-[(1r,2r)-2-hydroxy-4-methyl-5-oxocyclohex-3-en-1-yl]-4b,8,8,10a-tetramethyl-4,4a,5,6,7,8a,9,10-octahydro-1h-phenanthren-9-yl acetate
[(2r)-6-methyl-2-[(1r)-4-methylcyclohex-3-en-1-yl]hept-5-en-2-yl]sulfanylcarbonitrile
(4ar,5r,8r,8ar)-5-isopropyl-8-isothiocyanato-3,8-dimethyl-1,4a,5,6,7,8a-hexahydronaphthalen-2-one
(1r,2r,4r,5z,12r,13s,16e)-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
n-[(1e)-2-[(4as,6r,7s,8ar)-6-chloro-7-hydroxy-5,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-2-yl]ethenyl]-1-chloromethanecarbonimidoyl chloride
C16H22Cl3NO (349.07668920000003)
2-bromo-8-[1,1-dichloro-3-hydroxy-3-(4-methyl-5-oxooxolan-2-yl)propan-2-yl]-16-hydroxy-9,13-dimethyl-18-oxapentacyclo[13.2.1.0¹,¹³.0⁴,¹².0⁵,¹⁰]octadeca-5(10),6,8-triene-11,17-dione
n-{1,1,3a,7-tetramethyl-octahydrocyclopropa[a]naphthalen-7-yl}-n'-(2-phenylethyl)carbamimidothioic acid
(1s,2r,4ar,5r)-8-isopropyl-2,5-dimethyl-5-(sulfanylideneamino)-1,3,4,4a,6,7-hexahydronaphthalene-1,2-diol
1-chloro-n-[2-(6-chloro-5,5,8a-trimethyl-3,4,4a,6,7,8-hexahydronaphthalen-2-yl)ethenyl]methanecarbonimidoyl chloride
C16H22Cl3N (333.08177420000004)
(6e,10r,11e,13z)-10-hydroxy-2,6,10,14-tetramethylhexadeca-2,6,11,13,15-pentaen-4-one
4-bromo-n-[3-(2-imino-3-methyl-1h-imidazol-4-yl)prop-2-en-1-yl]-1h-pyrrole-2-carboxamide
(3s,6r,9s,12s,14e,16r,18s)-6-[(3-chloro-4-hydroxyphenyl)methyl]-5,11-dihydroxy-3-[(1r)-1-hydroxyethyl]-7,9,12,14,16,18-hexamethyl-1-oxa-4,7,10-triazacyclooctadeca-4,10,14-triene-2,8-dione
C29H42ClN3O7 (579.2711132000001)
3-[(4s)-2-(6-bromo-1h-indole-3-carbonyl)-4,5-dihydro-1h-imidazol-4-yl]-1h-indole
(1s,4ar,7s)-7-(2-isothiocyanatopropan-2-yl)-1,4a-dimethyl-2,3,4,5,6,7-hexahydro-1h-naphthalene
6-bromo-3-[2-(6-bromo-1h-indole-3-carbonyl)-4,5-dihydro-1h-imidazol-4-yl]-1h-indole
(2r)-n-[(4s,4ar,6s,8s,8ar)-6-(hydroxymethyl)-8-methoxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid
2-(2-hydroxypropan-2-yl)-5-isothiocyanato-5,9-dimethyl-10,12-dioxatricyclo[7.2.1.0¹,⁶]dodecan-11-ol
C16H25NO4S (327.15042100000005)
(1as,4r,7s,7as,7br)-4-hydroxy-1,1,7,7a-tetramethyl-1ah,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalen-2-one
3-[4-(6-bromo-1h-indol-3-yl)-1h-imidazole-2-carbonyl]-1h-indol-6-ol
(2r,5r,6r,10r,13s,15s)-6,10-dimethyl-5-[(2s,3e,5r)-5-methylhept-3-en-2-yl]-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadeca-8,18-dien-13-ol
9a,11a-dimethyl-1-(6-methyl-5-methylideneheptan-2-yl)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate
(2s,5s,10s)-7-isopropyl-2-isothiocyanato-2,10-dimethylspiro[4.5]dec-6-ene
(2r)-n-[(4s,4ar,6r,8s,8ar)-6-[(2s)-2,3-dihydroxypropyl]-8-hydroxy-7,7-dimethyl-hexahydropyrano[3,2-d][1,3]dioxin-4-yl]-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]ethanimidic acid
2-[(2s)-6-hydroxy-6-methylheptan-2-yl]-5-methylphenol
4-isopropyl-6-isothiocyanato-1,6-dimethyl-2,3,4,4a,5,7-hexahydro-1h-naphthalene
(5as,7ar,11as,11br)-5a,8,8,11a-tetramethyl-6,7,7a,9,10,11,11b,12-octahydro-5-oxatetraphen-2-ol
12-benzyl-11,14,23,26-tetrahydroxy-21-(1-hydroxyethyl)-9-isopropyl-24-methyl-1,7,10,13,19,22,25-heptaazatetracyclo[25.3.0.0³,⁷.0¹⁵,¹⁹]triaconta-10,13,22,25-tetraene-2,8,20-trione
C36H51N7O8 (709.3798926000001)
(3s,5r,9s)-5-hydroxy-1,7-diazatricyclo[7.3.0.0³,⁷]dodecane-2,8-dione
methyl 2-[(1e,5s,6s,8s,9s,13s,14r,16e)-6-{[(3s,5e,8r,9r)-9-(2-carbamoyl-1,3-oxazol-4-yl)-3-hydroxy-9-methoxy-8-methyl-7-oxonon-5-enoyl]oxy}-8,14-dimethoxy-5,9,13-trimethyl-17-(n-methylformamido)-12-oxoheptadeca-1,16-dien-1-yl]-1,3-oxazole-4-carboxylate
(4r,7r,10s,13s,15e,17r,19s)-7-[(3-chloro-4-hydroxyphenyl)methyl]-6,12-dihydroxy-4-(4-hydroxyphenyl)-8,10,13,15,17,19-hexamethyl-1-oxa-5,8,11-triazacyclononadeca-5,11,15-triene-2,9-dione
1-chloro-n-[(6e)-2-chloro-9-(3,3-dimethyloxiran-2-yl)-7-methyl-3-methylidenenon-6-en-1-yl]methanecarbonimidoyl chloride
(3e,5e,7r,10e)-7-ethoxy-3,7,11,15-tetramethylhexadeca-1,3,5,10,14-pentaene
n-[3-(4-hydroxyphenyl)-1-methoxy-1-oxopropan-2-yl]-4,6-dimethyldodeca-2,4-dienimidic acid
C24H35NO4 (401.25659500000006)
(1as,7s,7as,7br)-1,1,7,7a-tetramethyl-1ah,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalen-2-one
(5e)-5-[(6-bromo-1h-indol-3-yl)methylidene]-2-imino-3-methylimidazolidin-4-one
C13H11BrN4O (318.01161759999997)
(1ar,2s,7s,7as,7br)-1,1,7,7a-tetramethyl-1ah,2h,4h,5h,6h,7h,7bh-cyclopropa[a]naphthalene-2-carbonitrile
(2r,4ar,4br,8as,9r,10as)-2-hydroxy-2-[(1r,2r)-2-hydroxy-4-methyl-5-oxocyclohex-3-en-1-yl]-4b,8,8,10a-tetramethyl-decahydrophenanthren-9-yl acetate
n-[(2s,3s,4r)-1-{[(2r,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-17-methyloctadecan-2-yl]tricosanimidic acid
C50H98N2O9 (870.7271938000001)
2-(6-hydroxy-5-methylheptyl)-6-methoxy-3,5-dimethylpyran-4-one
1-(5-isopropylhept-5-en-2-yl)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-7-yl acetate
5-hydroxy-1,7-diazatricyclo[7.3.0.0³,⁷]dodecane-2,8-dione
(1r,3ar,5ar,7s,9ar,9br,11ar)-5a,7,9b-trihydroxy-9a,11a-dimethyl-1-[(2r,5r)-5-[(1r,2r)-2-methylcyclopropyl]hexan-2-yl]-1h,2h,3h,3ah,6h,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-5-one
(1s,4r,4ar,7r)-1-isopropyl-4,7-dimethyl-4-(sulfanylideneamino)-3,4a,5,6-tetrahydro-2h-naphthalene-1,7-diol
1-(5,6-dimethylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate
(1r,3as,3bs,4s,7s,9ar,9bs,11ar)-1-[(2r,3e)-5-tert-butyl-6-methylhepta-3,6-dien-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol
(1r,4ar,8as)-8a-isocyano-1,4a-dimethyl-7-propyl-1,2,3,4,5,6-hexahydronaphthalene
n-[(2s,5s,10s)-7-isopropyl-2,10-dimethylspiro[4.5]dec-6-en-2-yl]carboximidic acid
(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,3e,5s)-5-tert-butyl-6-methylhepta-3,6-dien-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
4-bromo-n-[3-(2,5-dihydroxyimidazol-4-ylidene)propyl]-1h-pyrrole-2-carboxamide
(3s,6s,12s,15s,18s,21s,24s)-15-benzyl-21-[(2s)-butan-2-yl]-5,14,17,20,23-pentahydroxy-18-(hydroxymethyl)-3-(1h-indol-2-ylmethyl)-12-isopropyl-1,4,10,13,16,19,22-heptaazatricyclo[22.3.0.0⁶,¹⁰]heptacosa-4,13,16,19,22-pentaene-2,11-dione
(3s,7r,8ar)-1,7-dihydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one
(1r,3as,3bs,4r,7s,9ar,9bs,11ar)-1-[(2r,3z)-5-isopropyl-6-methylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol
8-isothiocyanato-4a,8-dimethyl-2-(prop-1-en-2-yl)-hexahydro-1h-naphthalene-2-peroxol
[(3s,6s,9s,12s,15s,18s,21r,26as)-15-(4-aminobutyl)-9-benzyl-1,4,7,10,13,16,19-heptahydroxy-3-[(4-hydroxyphenyl)methyl]-12-(1h-indol-3-ylmethyl)-21-isopropyl-18-methyl-22-oxo-3h,6h,9h,12h,15h,18h,21h,24h,25h,26h,26ah-pyrrolo[1,2-a]1,4,7,10,13,16,19,22-octaazacyclotetracosan-6-yl]acetic acid
C52H66N10O11 (1006.4912286000001)
(2s)-n-[(1s)-1-{[(3s,6s,9r,12s,15s,16s)-9-benzyl-2,5,8,11-tetrahydroxy-12-[2-(c-hydroxycarbonimidoyl)ethyl]-3-(c-hydroxycarbonimidoylmethyl)-6-[(1r)-1-hydroxyethyl]-13,16-dimethyl-14,18-dioxo-1,4,7,10,13-pentaazacyclononadeca-1,4,7,10-tetraen-15-yl]-c-hydroxycarbonimidoyl}-2-sulfoethyl]-2-{[(2s)-2-{[(2s)-2-{[(2r)-2-({[(2s)-1-[(2s)-3-(4-bromophenyl)-2-{[(2r)-1-hydroxy-2-[(hydroxymethylidene)amino]propylidene]amino}propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3,3-dimethylbutylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-5-carbamimidamidopentanimidic acid
C79H111BrN20O21S (1786.7136336)
(1r,4r,4as,6s)-4-isopropyl-6-isothiocyanato-1,6-dimethyl-2,3,4,4a,5,7-hexahydro-1h-naphthalene
1-(5-isopropylhept-5-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
(6z,9s)-9-[(1e,3r,4r,6z,9z)-3,4-dihydroxydodeca-1,6,9-trien-1-yl]-4,5,8,9-tetrahydro-3h-oxonin-2-one
6-[(3-bromo-4-hydroxyphenyl)methyl]-5,11-dihydroxy-3-(1-hydroxyethyl)-7,9,12,14,16,18-hexamethyl-1-oxa-4,7,10-triazacyclooctadeca-4,10,14-triene-2,8-dione
1,7-dihydroxy-3-methyl-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one
(2r,5r,10s)-7-isopropyl-2-isothiocyanato-2,10-dimethylspiro[4.5]dec-6-ene
methyl 3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)pent-2-enoate
[(1r,5s,7s,8s,9ar,11ar)-9a,11a-dimethyl-7,8-bis(sulfooxy)-1-[(2r)-5,6,6-trimethylheptan-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-5-yl]oxidanesulfonic acid
C29H52O12S3 (688.2620751999999)
(1r,3as,3br,5as,7s,9as,9bs,11ar)-9a,11a-dimethyl-1-[(2r,3e)-5-methylhex-3-en-2-yl]-tetradecahydro-1h-cyclopenta[a]phenanthren-7-ol
[(1r,3as,3bs,5s,7s,8s,9ar,9bs,11ar)-1-[(2r,3z)-5-isopropyl-6-methylhepta-3,6-dien-2-yl]-9a,11a-dimethyl-7,8-bis(sulfooxy)-tetradecahydro-1h-cyclopenta[a]phenanthren-5-yl]oxidanesulfonic acid
(2r)-n-[(2s,3s,4r)-1-{[(2r,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-17-methyloctadecan-2-yl]-2-hydroxydocosanimidic acid
1-chloro-n-[(6e)-2-chloro-10,11-dihydroxy-7,11-dimethyl-3-methylidenedodec-6-en-1-yl]methanecarbonimidoyl chloride
C16H26Cl3NO2 (369.10290260000005)
3,3a-dihydroxy-1,1,7,7a-tetramethyl-hexahydro-1ah-cyclopropa[a]naphthalen-2-one
2-hydroxy-4b,8,8,10a-tetramethyl-2-(4-methyl-5-oxocyclohex-3-en-1-yl)-decahydrophenanthren-9-yl acetate
n-{1,7-dichloro-2,5-dihydroxy-8-oxobicyclo[3.3.1]non-6-en-3-yl}-4,6-dimethyldodeca-2,4-dienimidic acid
C23H33Cl2NO4 (457.17865180000007)
3-[1,4,7-trihydroxy-9-(hydroxymethyl)-10-oxo-3h,6h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-3-yl]propanoic acid
n-[(2r,5r,10s)-7-isopropyl-2,10-dimethylspiro[4.5]dec-6-en-2-yl]carboximidic acid
1-chloro-n-{2-chloro-2-[4-chloro-5-hydroxy-3-methyl-3-(4-methylpent-3-en-1-yl)cyclohexylidene]ethyl}methanecarbonimidoyl chloride
(5s)-5-hydroxy-5-(tetradeca-2,5,8-trien-1-yl)furan-2-one
(3e)-6-[(1s,3as,8ar)-3a,6-dimethyl-2,3,4,7,8,8a-hexahydro-1h-azulen-1-yl]-2-methylhept-3-ene-2,6-diol
2-[5-(4-methoxy-2,3,6-trimethylphenyl)-3-methylpent-2-en-1-yl]cyclohexa-2,5-diene-1,4-dione
6-bromo-3-[2-(1h-indole-3-carbonyl)-1h-imidazol-4-yl]-1h-indole
6-bromo-3-[(4s)-2-(1h-indole-3-carbonyl)-4,5-dihydro-1h-imidazol-4-yl]-1h-indole
5,11-dihydroxy-6-[(4-hydroxy-3-iodophenyl)methyl]-3-(1-hydroxyethyl)-7,9,12,14,16,18-hexamethyl-1-oxa-4,7,10-triazacyclooctadeca-4,10,14-triene-2,8-dione
C29H42IN3O7 (671.2067372000001)
(3s,6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylheptan-1-ol
(3s,6r,9s,12s,14e,16r,18s)-5,11-dihydroxy-6-[(4-hydroxy-3-iodophenyl)methyl]-3-[(1r)-1-hydroxyethyl]-9-(hydroxymethyl)-7,12,14,16,18-pentamethyl-1-oxa-4,7,10-triazacyclooctadeca-4,10,14-triene-2,8-dione
C29H42IN3O8 (687.2016522000001)
5-methoxy-2-[18-(4-methoxy-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]-1,3,3-trimethylcyclohex-1-ene
(10s,11r,12s,14s,16r,20r,21r,22s)-16-[(s)-amino(hydroxy)methoxy]-12-hydroxy-20-[(2r,3r,7r,8s,9r,10e)-11-[(hydroxymethyl)(methyl)amino]-2,8-dimethoxy-3,7,9-trimethyl-6-oxoundec-10-en-1-yl]-10,22-dimethoxy-11,14,21-trimethyl-3,7,19,27-tetraoxa-29,30,31-triazatetracyclo[24.2.1.1²,⁵.1⁶,⁹]hentriaconta-1(28),2(31),4,6(30),8,24,26(29)-heptaen-18-one
1-(5-isopropyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol
1-(5-ethyl-6-methylhept-3-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate
3-[2-(6-bromo-1h-indole-3-carbonyl)-1h-imidazol-4-yl]-1h-indole
4-bromo-n-[(2z)-3-(2-imino-3-methyl-1h-imidazol-4-yl)prop-2-en-1-yl]-1h-pyrrole-2-carboxamide
8-isopropyl-5-isothiocyanato-2,5-dimethyl-1,3,4,4a,6,7-hexahydronaphthalene-1,2-diol
3-[(3r,9s,14as)-1,4,7-trihydroxy-9-(hydroxymethyl)-10-oxo-3h,6h,9h,12h,13h,14h,14ah-pyrrolo[1,2-a]1,4,7,10-tetraazacyclododecan-3-yl]propanoic acid
n-[(2r,3r,4r)-1-{[(2s,3s,4r,5r,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-17-methyloctadecan-2-yl]docosanimidic acid
(1s,4s,4ar,7r)-7-hydroxy-1-isopropyl-4-isothiocyanato-4,7-dimethyl-3,4a,5,6-tetrahydro-2h-naphthalene-1-carboxylic acid
C17H25NO3S (323.15550600000006)
(2s)-n-[(2r,3r,4s)-1-{[(2s,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-15-methylhexadecan-2-yl]-2-hydroxytricosanimidic acid
11-ethyl-7,24,27,28-tetrahydroxy-10-methyl-21,26-diazatetracyclo[23.2.1.0⁸,¹⁵.0⁹,¹³]octacosa-1(28),3,5,16,18,26-hexaene-2,20-dione
(2r)-n-[(2s,3s,4r)-1-{[(2r,3r,4r,5s,6r)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydroxy-14-methylpentadecan-2-yl]-2-hydroxydocosanimidic acid
C46H90N2O10 (830.6595120000001)
3-[(3e)-5-(3,6-dioxocyclohexa-1,4-dien-1-yl)-3-methylpent-3-en-1-yl]-6-hydroxy-2,4-dimethylbenzaldehyde
(14z)-5,11-dihydroxy-6-[(4-hydroxy-3-iodophenyl)methyl]-3,7,12,14,16,18-hexamethyl-1-oxa-4,7,10-triazacyclooctadeca-4,10,14-triene-2,8-dione
(2s)-2-[(2s,3r)-2-{[(2s)-2-{[(2s)-2-{[(2r)-2-{[(2s)-2-{[(2r)-2-({[(2s)-1-[(2s)-3-(4-bromophenyl)-2-{[(2r)-1-hydroxy-2-[(hydroxymethylidene)amino]propylidene]amino}propanoyl]pyrrolidin-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-methylbutylidene]amino}-1-hydroxy-3,3-dimethylbutylidene]amino}-1-hydroxy-3-(1h-indol-3-yl)propylidene]amino}-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxy-3-sulfopropylidene]amino}-3-hydroxy-n-methylbutanamido]-n-[(1r)-1-(c-hydroxycarbonimidoyl)-2-phenylethyl]pentanediimidic acid
C68H96BrN17O17S (1533.6073826)