NCBI Taxonomy: 1162

Palmitic acid

C16H32O2 (256.2402)

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

C40H56 (536.4382)

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

Zeaxanthin

C40H56O2 (568.428)

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

Squalene

C30H50 (410.3912)

Squalene is an unsaturated aliphatic hydrocarbon (carotenoid) with six unconjugated double bonds found in human sebum (5\\\\%), fish liver oils, yeast lipids, and many vegetable oils (e.g. palm oil, cottonseed oil, rapeseed oil). Squalene is a volatile component of the scent material from Saguinus oedipus (cotton-top tamarin monkey) and Saguinus fuscicollis (saddle-back tamarin monkey) (Hawleys Condensed Chemical Reference). Squalene is a component of adult human sebum that is principally responsible for fixing fingerprints (ChemNetBase). It is a natural organic compound originally obtained for commercial purposes primarily from shark liver oil, though there are botanical sources as well, including rice bran, wheat germ, and olives. All higher organisms produce squalene, including humans. It is a hydrocarbon and a triterpene. Squalene is a biochemical precursor to the whole family of steroids. Oxidation of one of the terminal double bonds of squalene yields 2,3-squalene oxide which undergoes enzyme-catalyzed cyclization to afford lanosterol, which is then elaborated into cholesterol and other steroids. Squalene is a low-density compound often stored in the bodies of cartilaginous fishes such as sharks, which lack a swim bladder and must therefore reduce their body density with fats and oils. Squalene, which is stored mainly in the sharks liver, is lighter than water with a specific gravity of 0.855 (Wikipedia) Squalene is used as a bactericide. It is also an intermediate in the manufacture of pharmaceuticals, rubber chemicals, and colouring materials (Physical Constants of Chemical Substances). Trans-squalene is a clear, slightly yellow liquid with a faint odor. Density 0.858 g / cm3. Squalene is a triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. It has a role as a human metabolite, a plant metabolite, a Saccharomyces cerevisiae metabolite and a mouse metabolite. Squalene is originally obtained from shark liver oil. It is a natural 30-carbon isoprenoid compound and intermediate metabolite in the synthesis of cholesterol. It is not susceptible to lipid peroxidation and provides skin protection. It is ubiquitously distributed in human tissues where it is transported in serum generally in association with very low density lipoproteins. Squalene is investigated as an adjunctive cancer therapy. Squalene is a natural product found in Ficus septica, Garcinia multiflora, and other organisms with data available. squalene is a metabolite found in or produced by Saccharomyces cerevisiae. A natural 30-carbon triterpene. See also: Olive Oil (part of); Shark Liver Oil (part of). A triterpene consisting of 2,6,10,15,19,23-hexamethyltetracosane having six double bonds at the 2-, 6-, 10-, 14-, 18- and 22-positions with (all-E)-configuration. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].

Amyrin

C30H50O (426.3861)

Beta-amyrin is a pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. It has a role as a plant metabolite and an Aspergillus metabolite. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an oleanane. beta-Amyrin is a natural product found in Ficus pertusa, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Centaurium erythraea whole (part of). A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

Phytol

C20H40O (296.3079)

Phytol, also known as trans-phytol or 3,7,11,15-tetramethylhexadec-2-en-1-ol, is a member of the class of compounds known as acyclic diterpenoids. Acyclic diterpenoids are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. Thus, phytol is considered to be an isoprenoid lipid molecule. Phytol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Phytol can be found in a number of food items such as salmonberry, rose hip, malus (crab apple), and black raspberry, which makes phytol a potential biomarker for the consumption of these food products. Phytol can be found primarily in human fibroblasts tissue. Phytol is an acyclic diterpene alcohol that can be used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. In ruminants, the gut fermentation of ingested plant materials liberates phytol, a constituent of chlorophyll, which is then converted to phytanic acid and stored in fats. In shark liver it yields pristane . Phytol is a diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. It has a role as a plant metabolite, a schistosomicide drug and an algal metabolite. It is a diterpenoid and a long-chain primary fatty alcohol. Phytol is a natural product found in Elodea canadensis, Wendlandia formosana, and other organisms with data available. Phytol is an acyclic diterpene alcohol and a constituent of chlorophyll. Phytol is commonly used as a precursor for the manufacture of synthetic forms of vitamin E and vitamin K1. Furthermore, phytol also was shown to modulate transcription in cells via transcription factors PPAR-alpha and retinoid X receptor (RXR). Acyclic diterpene used in making synthetic forms of vitamin E and vitamin K1. Phytol is a natural linear diterpene alcohol which is used in the preparation of vitamins E and K1. It is also a decomposition product of chlorophyll. It is an oily liquid that is nearly insoluble in water, but soluble in most organic solvents. -- Wikipedia. A diterpenoid that is hexadec-2-en-1-ol substituted by methyl groups at positions 3, 7, 11 and 15. C1907 - Drug, Natural Product > C28269 - Phytochemical Acquisition and generation of the data is financially supported in part by CREST/JST. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1]. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1].

Retinal

C20H28O (284.214)

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

Nodularin

C41H60N8O10 (824.4432)

CONFIDENCE standard compound; EAWAG_UCHEM_ID 3252

gamma-Glutamylcysteine

C8H14N2O5S (250.0623)

gamma-Glutamylcysteine is a dipeptide composed of gamma-glutamate and cysteine, and is a proteolytic breakdown product of larger proteins. It belongs to the family of N-acyl-alpha amino acids and derivatives. These are compounds containing an alpha amino acid which bears an acyl group at its terminal nitrogen atom. gamma-Glutamylcysteine is an incomplete breakdown product of protein digestion or protein catabolism. Some dipeptides are known to have physiological or cell-signaling effects although most are simply short-lived intermediates on their way to specific amino acid degradation pathways following further proteolysis. gamma-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in the glutamate metabolism pathway (KEGG). G-Glutamylcysteine is a product of enzyme glutamate-cysteine ligase [EC 6.3.2.2] and a substrate of enzyme glutathione synthase [EC 6.3.2.3] in glutamate metabolism pathway (KEGG). gamma-Glutamyl-cysteine is found in many foods, some of which are cardamom, hyacinth bean, oil palm, and pak choy. Acquisition and generation of the data is financially supported in part by CREST/JST. Gamma-glutamylcysteine (γ-Glutamylcysteine), a dipeptide containing cysteine and glutamic acid, is a precursor to glutathione (GSH). Gamma-glutamylcysteine is a cofactor for glutathione peroxidase (GPx) to increase GSH levels[1].

Cholesterol

C27H46O (386.3548)

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

Canthaxanthin

C40H52O2 (564.3967)

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

Dehydroabietic acid

C20H28O2 (300.2089)

Dehydroabietic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. Dehydroabietic acid possesses antiviral activity[1]. Dehydroabietic acid possesses antiviral activity[1].

Nostoxanthin

C40H56O4 (600.4178)

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.

echinenone

C40H54O (550.4174)

A carotenone that is beta-carotene in which the 4 position has undergone formal oxidation to afford the corresponding ketone. Isolated as orange-red crystals, it is widely distributed in marine invertebrates. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids Window width for selecting the precursor ion was 3 Da.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 16HP2005 to the Mass Spectrometry Society of Japan.

Myxol

C40H56O3 (584.4229)

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

Brassicasterol

C28H46O (398.3548)

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].

Heptadecane

C17H36 (240.2817)

Heptadecane, also known as CH3-[CH2]15-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Heptadecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, heptadecane is considered to be a hydrocarbon lipid molecule. Heptadecane is an organic compound, an alkane hydrocarbon with the chemical formula C17H36. The most compact and branched isomer would be tetra-tert-butylmethane, but its existence is believed to be impossible due to steric hindrance. The name may refer to any of 24894 theoretically possible structural isomers, or to a mixture thereof. Heptadecane is an alkane tasting compound. heptadecane has been detected, but not quantified, in several different foods, such as lemon balms, coconuts, orange bell peppers, allspices, and pepper (c. annuum). This could make heptadecane a potential biomarker for the consumption of these foods. In the IUPAC nomenclature, the name of this compound is simply heptadecane, since the other isomers are viewed and named as alkyl-substituted versions of smaller alkanes. The unbranched isomer is normal or n-heptadecane, CH3(CH2)15CH3. Indeed, it is believed to be the smallest "impossible" alkane. Heptadecane, also known as ch3-[ch2]15-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, heptadecane is considered to be a hydrocarbon lipid molecule. Heptadecane is an alkane tasting compound and can be found in a number of food items such as papaya, orange bell pepper, pepper (spice), and red bell pepper, which makes heptadecane a potential biomarker for the consumption of these food products. Heptadecane can be found primarily in saliva. The unbranched isomer is normal or n-heptadecane, CH3(CH2)15CH3. In the IUPAC nomenclature, the name of this compound is simply heptadecane, since the other isomers are viewed and named as alkyl-substituted versions of smaller alkanes .

Pentadecane

C15H32 (212.2504)

Pentadecane, also known as ch3-[ch2]13-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, pentadecane is considered to be a hydrocarbon lipid molecule. Pentadecane is an alkane and waxy tasting compound and can be found in a number of food items such as dill, papaya, yellow bell pepper, and pepper (c. annuum), which makes pentadecane a potential biomarker for the consumption of these food products. Pentadecane can be found primarily in saliva. Pentadecane is a non-carcinogenic (not listed by IARC) potentially toxic compound. Pentadecane is an alkane hydrocarbon with the chemical formula C15H32 . Pentadecane belongs to the family of Acyclic Alkanes. These are acyclic hydrocarbons consisting only of n carbon atoms and m hydrogen atoms where m=2*n + 2

Echinone

C19H20O6 (344.126)

Nostopeptolide A1

C53H80N10O14 (1080.5855)

Nostocyclopeptide A1

C37H56N8O9 (756.417)

Nostocyclopeptide A3

C41H56N8O9 (804.417)

caloxanthin

C40H56O3 (584.4229)

cryptophycin

C35H43ClN2O8 (654.2708)

C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C273 - Antimitotic Agent

D-Arabinose

C5H10O5 (150.0528)

CONFIDENCE standard compound; INTERNAL_ID 233 Arabinose is an endogenous metabolite. Arabinose is an endogenous metabolite. D-Arabinose, a monosaccharide, shows strong growth inhibition against the Caenorhabditis elegans with an IC50 of 7.5 mM[1]. D-Arabinose, a monosaccharide, shows strong growth inhibition against the Caenorhabditis elegans with an IC50 of 7.5 mM[1]. D-arabinose is an endogenous metabolite. D-arabinose is an endogenous metabolite.

nostocyclopeptide A2

C40H54N8O9 (790.4014)

Isozeaxanthin

C40H56O2 (568.428)

Isozeaxanthin is found in fishes. Isozeaxanthin is widespread in marine animals. Additive for salmon feed. Widespread in marine animals. Additive for salmon feed. Isozeaxanthin is found in fishes.

D-Homophenylalanine

C10H13NO2 (179.0946)

1-Heptadecene

C17H34 (238.266)

1-heptadecene is a member of the class of compounds known as unsaturated aliphatic hydrocarbons. Unsaturated aliphatic hydrocarbons are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. These compounds contain one or more double or triple bonds. Thus, 1-heptadecene is considered to be a hydrocarbon lipid molecule. 1-heptadecene can be found in burdock and safflower, which makes 1-heptadecene a potential biomarker for the consumption of these food products.

Dehydroabietic acid

C20H28O2 (300.2089)

Dehydroabietic acid is an abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group. It has a role as a metabolite and an allergen. It is an abietane diterpenoid, a monocarboxylic acid and a carbotricyclic compound. It is functionally related to an abietic acid. It is a conjugate acid of a dehydroabietate. Dehydroabietic acid is a natural product found in Nostoc, Relhania corymbosa, and other organisms with data available. Dehydroabietic acid belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. An abietane diterpenoid that is abieta-8,11,13-triene substituted at position 18 by a carboxy group. Dehydroabietic acid possesses antiviral activity[1]. Dehydroabietic acid possesses antiviral activity[1].

β-Amyrin

C30H50O (426.3861)

Beta-amyrin, also known as amyrin or (3beta)-olean-12-en-3-ol, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Thus, beta-amyrin is considered to be an isoprenoid lipid molecule. Beta-amyrin is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Beta-amyrin can be synthesized from oleanane. Beta-amyrin is also a parent compound for other transformation products, including but not limited to, erythrodiol, glycyrrhetaldehyde, and 24-hydroxy-beta-amyrin. Beta-amyrin can be found in a number of food items such as thistle, pepper (c. baccatum), wakame, and endive, which makes beta-amyrin a potential biomarker for the consumption of these food products. The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C30H50O. They are widely distributed in nature and have been isolated from a variety of plant sources such as epicuticular wax. In plant biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato fruit. α-Amyrin is found in dandelion coffee . β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1]. β-Amyrin, an ingredient of Celastrus hindsii, blocks amyloid β (Aβ)-induced long-term potentiation (LTP) impairment. β-amyrin is a promising candidate of treatment for AD[1].

Palmitic Acid

C16H32O2 (256.2402)

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

Squalene

C30H50 (410.3912)

Squalene, also known as (e,e,e,e)-squalene or all-trans-squalene, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Squalene can be found in a number of food items such as apricot, savoy cabbage, peach (variety), and bitter gourd, which makes squalene a potential biomarker for the consumption of these food products. Squalene can be found primarily in blood, feces, and sweat, as well as throughout most human tissues. In humans, squalene is involved in several metabolic pathways, some of which include risedronate action pathway, steroid biosynthesis, alendronate action pathway, and fluvastatin action pathway. Squalene is also involved in several metabolic disorders, some of which include cholesteryl ester storage disease, CHILD syndrome, hyper-igd syndrome, and wolman disease. Squalene is a natural 30-carbon organic compound originally obtained for commercial purposes primarily from shark liver oil (hence its name, as Squalus is a genus of sharks), although plant sources (primarily vegetable oils) are now used as well, including amaranth seed, rice bran, wheat germ, and olives. Yeast cells have been genetically engineered to produce commercially useful quantities of "synthetic" squalene . COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Window width to select the precursor ion was 3 Da.; CONE_VOLTAGE was 20 V.; This record was created by the financial support of MEXT/JSPS KAKENHI Grant Number 19HP8024 to the Mass Spectrometry Society of Japan. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2]. Squalene is an intermediate product in the synthesis of cholesterol, and shows several pharmacological properties such as hypolipidemic, hepatoprotective, cardioprotective, antioxidant, and antitoxicant activity. Squalene also has anti-fungal activity and can be used for the research of Trichophyton mentagrophytes research[2].

Cholesterol

C27H46O (386.3548)

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

7-METHYLHEPTADECANE

C18H38 (254.2973)

Norharmane

C11H8N2 (168.0687)

D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens IPB_RECORD: 2981; CONFIDENCE confident structure Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6]. Norharmane (Norharman), a β-carboline alkaloid, is a potent and reversible monoamine oxidase inhibitor, with IC50 values of 6.5 and 4.7 μM for MAO-A and MAO-B, respectively. Norharmane causes antidepressant responses. Norharmane is also a prospective anti-cancer photosensitizer. Norharmane alters polar auxin transport (PAT) by inhibiting PIN2, PIN3 and PIN7 transport proteins, thus causing a significant inhibitory effect on the growth of Arabidopsis thaliana seedlings[1][2][3][4][5][6].

Brassicasterol

C28H46O (398.3548)

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

C40H56 (536.4382)

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

Phytol

C20H40O (296.3079)

Phytol is a key acyclic diterpene alcohol that is a precursor for vitamins E and K1. Phytol is an extremely common terpenoid, found in all plants esterified to Chlorophyll to confer lipid solubility[citation needed].; Phytol is a natural linear diterpene alcohol which is used in the preparation of vitamins E and K1. It is also a decomposition product of chlorophyll. It is an oily liquid that is nearly insoluble in water, but soluble in most organic solvents. -- Wikipedia C1907 - Drug, Natural Product > C28269 - Phytochemical Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1]. Phytol ((E)?-?Phytol), a diterpene alcohol from chlorophyll widely used as a food additive and in medicinal fields, possesses promising antischistosomal properties. Phytol has antinociceptive and antioxidant activitiesas well as anti-inflammatory and antiallergic effects. Phytol has antimicrobial activity against Mycobacterium tuberculosis and Staphylococcus aureus[1].

Zeaxanthin

C40H56O2 (568.428)

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

Gamma-glutamylcysteine

C8H14N2O5S (250.0623)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; RITKHVBHSGLULN_STSL_0116_5-Glutamylcysteine_8000fmol_180506_S2_LC02_MS02_219; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. Gamma-glutamylcysteine (γ-Glutamylcysteine), a dipeptide containing cysteine and glutamic acid, is a precursor to glutathione (GSH). Gamma-glutamylcysteine is a cofactor for glutathione peroxidase (GPx) to increase GSH levels[1].

Arabinose

C5H10O5 (150.0528)

Arabinose is an aldopentose – a monosaccharide containing five carbon atoms, and including an aldehyde (CHO) functional group. Arabinose is found in many foods, some of which are arabica coffee, olive, soy bean, and apple. Arabinose is an endogenous metabolite. Arabinose is an endogenous metabolite. D-arabinose is an endogenous metabolite. D-arabinose is an endogenous metabolite.

Hexadecanoic acid

C16H32O2 (256.2402)

24-methylene-cycloartanol

C31H52O (440.4018)

Erlose

C18H32O16 (504.169)

g-Muurolene

C15H24 (204.1878)

Pentadecane

C15H32 (212.2504)

A straight-chain alkane with 15 carbon atoms. It is a component of volatile oils isolated from plants species like Scandix balansae.

canthaxanthin

C40H52O2 (564.3967)

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

Isozeaxanthin

C40H56O2 (568.428)

D-Homophenylalanine

C10H13NO2 (179.0946)

Heptadecene

C17H34 (238.266)

Retinal

C20H28O (284.214)

An enal that consists of 3,7-dimethyl-9-nona-2,4,6,8-tetraenal (double bond geometry unspecified) carrying a 2,6,6-trimethylcyclohex-1-en-1-yl group at the 9-position. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

Porphyra 334

C14H22N2O8 (346.1376)

Apo-8-lycopenal

C30H40O (416.3079)

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

(2S)-2-amino-3-(methylamino)propanoate

C4H10N2O2 (118.0742)

(+)-gamma-cadinene

C15H24 (204.1878)

A member of the cadinene family of sesquiterpenes in which the isopropyl group is cis to the hydrogen at the adjacent bridgehead carbon (the 1S,4aR,8aR enantiomer).

Dihydrocholesterol

C27H48O (388.3705)

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

Avenasterol

C29H48O (412.3705)

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

(2s)-n-[(1s,5r,7s,11s,13s,23s,26r,29s,32s,39r)-29-[(2s)-butan-2-yl]-5,24,27,30,33,39-hexahydroxy-35-(hydroxymethyl)-32-[(4-hydroxyphenyl)methyl]-11-methyl-26-(2-methylpropyl)-2,8,14,18,36-pentaoxo-15-oxa-3,9,19,25,28,31,34,37-octaazapentacyclo[35.3.0.0³,⁷.0⁹,¹³.0¹⁹,²³]tetraconta-24,27,30,33-tetraen-17-yl]-2-(n-methylacetamido)-3-phenylpropanimidic acid

C60H84N10O16 (1200.6066)

2-[(3,27-dihydroxyoctacosyl)oxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C34H68O8 (604.4914)

{[(2r,3s,8r,13r,14s,19r)-8,19-bis(4,4-dibromobutyl)-10,21,24,26-tetrahydroxy-13-(c-hydroxycarbonimidoyloxy)-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaen-2-yl]oxy}methanimidic acid

C38H54Br4N2O8 (982.0613)

n-[2-(1-carbamimidoyl-2,5-dihydropyrrol-3-yl)ethyl]-10-{[3-(hexanoyloxy)-5-hydroxy-4-(c-hydroxycarbonimidoyloxy)-6-(hydroxymethyl)oxan-2-yl]oxy}-3,12-dihydroxy-7-(2-{[1-hydroxy-2-methoxy-3-(sulfooxy)propylidene]amino}-4-methylpentanoyl)-2-oxa-4,7-diazatricyclo[6.3.1.0¹,⁵]dodec-3-ene-6-carboximidic acid

C40H64N8O19S (992.4008)

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

C44H65N7O9S2 (899.4285)

2-({[3-benzyl-2,5,11,14-tetrahydroxy-6,7-dimethyl-8-oxo-9-(2-phenylethyl)-12-(sec-butyl)-1,4,7,10,13-pentaazacyclononadeca-1,4,10,13-tetraen-15-yl]-c-hydroxycarbonimidoyl}amino)-3-methylbutanoic acid

C41H59N7O8 (777.4425)

(2s,3s)-3-{[(1s)-1-[bis(4-aminobutyl)carbamoyl]-3-methylbutyl]-c-hydroxycarbonimidoyl}oxirane-2-carboxylic acid

C18H34N4O5 (386.2529)

3-[(3r,4r,7s,13s,16s,19s,22r,25s,28s,33as)-10-ethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-28-(c-hydroxycarbonimidoylmethyl)-13,16-bis[(1r)-1-hydroxyethyl]-7-isopropyl-25-[(1r)-1-methoxyethyl]-22,27-dimethyl-26,29-dioxo-3-[(2s)-13-oxohexadecan-2-yl]-3h,4h,7h,13h,16h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-19-yl]propanimidic acid

C59H100N12O17 (1248.7329)

3-[(3r,6s,9r,13s,16r,19s,22r,25s,28s,31r,34s,39as)-13,28-bis[(2s)-butan-2-yl]-9-heptyl-1,4,7,11,14,17,20,23,29,32-decahydroxy-16,22-bis[(1s)-1-hydroxy-2-methylpropyl]-19-(2-hydroxyethyl)-6,34-bis[(1r)-1-hydroxyethyl]-31-(hydroxymethyl)-3-[(4-hydroxyphenyl)methyl]-27-methyl-26,35-dioxo-3h,6h,9h,10h,13h,16h,19h,22h,25h,28h,31h,34h,37h,38h,39h,39ah-pyrrolo[2,1-i]1,4,7,10,13,16,19,22,25,28,31,34-dodecaazacycloheptatriacontan-25-yl]propanimidic acid

C69H115N13O20 (1445.8381)

n-{2-benzyl-6,13,16,21-tetrahydroxy-5-[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-15-(2-methylpropyl)-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-2-[(1-hydroxyethylidene)amino]pentanediimidic acid

C46H64N8O12 (920.4643)

2-[({3-benzyl-2,5,11,14-tetrahydroxy-9-[2-(4-hydroxyphenyl)ethyl]-12-isopropyl-6,7-dimethyl-8-oxo-1,4,7,10,13-pentaazacyclononadeca-1,4,10,13-tetraen-15-yl}-c-hydroxycarbonimidoyl)amino]-3-(4-hydroxyphenyl)propanoic acid

C44H57N7O10 (843.4167)

(13e)-10-[(3-chloro-4-methoxyphenyl)methyl]-16-(3,4-dihydroxy-4-phenylbutan-2-yl)-9,12-dihydroxy-6-methyl-3-(2-methylpropyl)-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C35H45ClN2O9 (672.2813)

10-[(3-chloro-4-methoxyphenyl)methyl]-9,12-dihydroxy-6-methyl-3-(2-methylpropyl)-16-(3-phenylprop-2-en-1-yl)-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C34H41ClN2O7 (624.2602)

3-[(10e)-3-(12-chlorotetradecan-2-yl)-10-ethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-28-(c-hydroxycarbonimidoylmethyl)-13-(1-hydroxyethyl)-7,16-diisopropyl-25-(1-methoxyethyl)-27-methyl-26,29-dioxo-3h,4h,7h,13h,16h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-19-yl]propanimidic acid

C57H97ClN12O15 (1224.6885)

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

C44H57N7O10 (843.4167)

(3s,6r,9r,12s,15r,18s,28s,31e,35r,36as)-6-benzyl-31-ethylidene-24-heptyl-1,4,7,10,13,16,19,22,26,29,35-undecahydroxy-3,28-bis(2-hydroxyethyl)-9,18-bis(2-methylpropyl)-12,15-bis(sec-butyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,28h,34h,35h,36h,36ah-pyrrolo[1,2-g]1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotetratriacontan-32-one

C62H101N11O14 (1223.7529)

(13e)-10-[(3-chloro-4-methoxyphenyl)methyl]-9,12-dihydroxy-6-methyl-3-(2-methylpropyl)-16-[(3e)-4-phenylbut-3-en-2-yl]-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C35H43ClN2O7 (638.2759)

(2s)-3-{[(2r)-3-(3-chloro-4-methoxyphenyl)-1-hydroxy-2-{[(2e,5s,6r)-1-hydroxy-5-{[(2s)-2-hydroxy-4-methylpentanoyl]oxy}-6-[(2s,3r)-3-phenyloxiran-2-yl]hept-2-en-1-ylidene]amino}propylidene]amino}-2-methylpropanoic acid

C35H45ClN2O9 (672.2813)

(2s,3s)-2-[(1-hydroxybutylidene)amino]-3-methyl-n-[(3s,7s,13s,16s,22s,27s,30s,32s)-15,18,21,24,29-pentahydroxy-16-(c-hydroxycarbonimidoylmethyl)-13-[(4-hydroxyphenyl)methyl]-32-methyl-22,27-bis(2-methylpropyl)-2,6,12,26-tetraoxo-5-oxa-1,11,14,17,20,23,28-heptaazatricyclo[28.3.0.0⁷,¹¹]tritriaconta-14,17,20,23,28-pentaen-3-yl]pentanimidic acid

C53H80N10O14 (1080.5855)

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

C43H62N8O9 (834.464)

2-hydroxy-3-{[3-(n-hydroxyacetamido)propyl]-c-hydroxycarbonimidoyl}-2-({[3-(n-hydroxyacetamido)propyl]-c-hydroxycarbonimidoyl}methyl)propanoic acid

C16H28N4O9 (420.1856)

(2s)-n-(5-carbamimidamido-1-oxopentan-2-yl)-2-{[(2r)-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxy-4-(4-hydroxyphenyl)butylidene]amino}-4-methylpentanimidic acid

C31H44N6O7 (612.3271)

3-{[2-benzyl-15-(4-carbamimidoylbutyl)-6,13,16,21-tetrahydroxy-5-[2-(4-hydroxyphenyl)ethyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-c-hydroxycarbonimidoyl}-3-[(1-hydroxyhexylidene)amino]propanoic acid

C51H73N9O13 (1019.5328)

3-{[(3r,3ar,5as,6r,7r,9as,9br)-3-(dimethoxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid

C29H44O5 (472.3189)

2-[({3-benzyl-2,5,8,14-tetrahydroxy-10-methyl-6-[(methyl-c-hydroxycarbonimidoyl)methyl]-11-oxo-9-(2-phenylethyl)-12-(sec-butyl)-1,4,7,10,13-pentaazacyclononadeca-1,4,7,13-tetraen-15-yl}-c-hydroxycarbonimidoyl)amino]-3-phenylpropanoic acid

C47H62N8O9 (882.464)

(2s,3r,4s,5r,6r)-6-{[(2s,3s,4r,5r)-2-({1-[(1-{[1-({1-[(1-{[(1z)-1-{[1-({[(1-{[1-carboxy-3-(c-hydroxycarbonimidoyl)propyl]-c-hydroxycarbonimidoyl}-2-{[(2r,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl)(methyl)carbamoyl]methyl}-c-hydroxycarbonimidoyl)-3-(c-hydroxycarbonimidoyl)propyl]-c-hydroxycarbonimidoyl}prop-1-en-1-yl]-c-hydroxycarbonimidoyl}-2-hydroxy-2-(4-hydroxyphenyl)ethyl)-c-hydroxycarbonimidoyl]-2-hydroxypropyl}-c-hydroxycarbonimidoyl)-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl)-c-hydroxycarbonimidoyl]-12-chloro-1-hydroxypentadecan-2-yl}oxy)-3,5-dihydroxyoxan-4-yl]oxy}-3,4,5-trihydroxyoxane-2-carboxylic acid

C75H120ClN11O36 (1785.7586)

n-[(2s)-5-carbamimidamido-1-oxopentan-2-yl]-2-{[1,2-dihydroxy-4-(4-hydroxyphenyl)butylidene]amino}-3-methylbutanimidic acid

C21H33N5O5 (435.2482)

8,19-bis(4,4-dichlorobutyl)-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaene-2,10,21,24,26-pentol

C36H52Cl4O5 (704.2569)

3-[3-(12-chlorotetradecan-2-yl)-10-ethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-28-(c-hydroxycarbonimidoylmethyl)-13,16-bis(1-hydroxyethyl)-7-isopropyl-25-(1-methoxyethyl)-27-methyl-26,29-dioxo-3h,4h,7h,13h,16h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-19-yl]propanimidic acid

C56H95ClN12O16 (1226.6677)

(27r)-27-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octacosan-3-one

C34H66O8 (602.4757)

2-(hydroxymethyl)-6-[(3,25,27-trihydroxyoctacosyl)oxy]oxane-3,4,5-triol

C34H68O9 (620.4863)

3-methyl-2-({[2,5,8-trihydroxy-3-(2-phenylethyl)-6-(sec-butyl)-1,4,7-triazacyclotrideca-1,4,7-trien-9-yl]-c-hydroxycarbonimidoyl}amino)butanoic acid

C28H43N5O6 (545.3213)

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

C41H60N10O10 (852.4494)

[(3s,6s,12s)-9-benzyl-2,5,8,14-tetrahydroxy-3,10,15-trimethyl-12-[3-({[(methyl-c-hydroxycarbonimidoyl)amino]methanimidoyl}amino)propyl]-11-oxo-16-[(2e)-pent-2-en-1-yl]-1,4,7,10,13-pentaazacyclohexadeca-1,4,7,13-tetraen-6-yl]acetic acid

C34H51N9O8 (713.386)

(3s,6r,10r,13e,16s)-10-[(3-chloro-4-hydroxyphenyl)methyl]-9,12-dihydroxy-6-methyl-3-(2-methylpropyl)-16-[(2r,3e)-4-phenylbut-3-en-2-yl]-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C34H41ClN2O7 (624.2602)

3-hydroxy-2-{[5-hydroxy-3-imino-2-methoxy-5-({[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}methyl)cyclohex-1-en-1-yl]amino}butanoic acid

C18H30N2O11 (450.185)

3-{[2,5-dibenzyl-15-(3-carbamimidamidopropyl)-6,13,16,21-tetrahydroxy-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-c-hydroxycarbonimidoyl}-3-[(1-hydroxyhexylidene)amino]propanoic acid

C49H70N10O12 (990.5174)

n-[(1e,3r,4r,5r,9s,10s,11s)-10-hydroxy-11-[(1s,3s,4r,5s,7r,8s,9r,12e,14e,17s,19r)-17-hydroxy-4-(hydroxymethyl)-3,5,7-trimethoxy-8,14-dimethyl-11-oxo-10,23-dioxabicyclo[17.3.1]tricosa-12,14,20-trien-9-yl]-4-methoxy-3,5,9-trimethyl-6-oxododec-1-en-1-yl]-n-methylformamide

C45H75NO12 (821.5289)

1,1'-bis(4-hydroxyphenyl)-3,3',4,4'-tetrakis[(4-hydroxyphenyl)methyl]-[1,1'-bi(cyclopentane)]-3,3'-diene-2,2',5,5'-tetrone

C50H38O10 (798.2465)

(5r,8s,11r,15s,18s,19s,22r)-15-(3-carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-18-[(1e,3e,5s,6s)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,5,19-trimethyl-2-methylidene-8-(2-methylpropyl)-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C47H70N10O12 (966.5174)

4-hydroxy-3-{[3-(hydroxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}benzoic acid

C27H40O4 (428.2926)

3-[(3r,4r,7s,10e,13s,16s,19s,22r,25s,28s,33as)-10-ethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-28-(c-hydroxycarbonimidoylmethyl)-13-[(1r)-1-hydroxyethyl]-7,16-diisopropyl-25-[(1r)-1-methoxyethyl]-22,27-dimethyl-26,29-dioxo-3-[(2s)-13-oxohexadecan-2-yl]-3h,4h,7h,13h,16h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-19-yl]propanimidic acid

C60H102N12O16 (1246.7536)

(2s)-3-(3-chloro-4-methoxyphenyl)-2-{[(2e,5s,6s,7r,8s)-1,5,7,8-tetrahydroxy-6-methyl-8-phenyloct-2-en-1-ylidene]amino}propanoic acid

C25H30ClNO7 (491.1711)

(2s,3r,4s,5s,6r)-2-{[(3r,25r)-3,25-dihydroxyhexacosyl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C32H64O8 (576.4601)

(5r,8s,11r,15s,18s,19s,22r)-18-[(1e,3e,5s,6s)-6-(acetyloxy)-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-15-(3-carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-1,5,19-trimethyl-2-methylidene-8-(2-methylpropyl)-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C49H72N10O13 (1008.528)

3-[(3r,4r,7s,13s,16s,19s,22r,25s,28s,33as)-3-[(2s)-10-chlorododecan-2-yl]-10-ethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-28-(c-hydroxycarbonimidoylmethyl)-13,16-bis[(1r)-1-hydroxyethyl]-7-isopropyl-25-[(1r)-1-methoxyethyl]-22,27-dimethyl-26,29-dioxo-3h,4h,7h,13h,16h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-19-yl]propanimidic acid

C55H93ClN12O16 (1212.6521)

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

C45H59N7O9 (841.4374)

12,13-dihydroxyoctadeca-9,10-dienoic acid

C18H32O4 (312.23)

(3z)-3-[(4-hydroxyphenyl)methylidene]-4h-cyclopenta[b]indole-1,2-dione

C18H11NO3 (289.0739)

3-{[(2s,3s,4r,5r)-4-{[(2r,3s,4s,5r,6s)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-n-(1-{[(3s,12r,15z,18r,21s,24s,25r)-15-ethylidene-5,11,14,17,20,23-hexahydroxy-12-[2-(c-hydroxycarbonimidoyl)ethyl]-21-[(1s)-1-hydroxyethyl]-3,18-bis[(4-hydroxyphenyl)methyl]-7,25-dimethyl-2,8-dioxo-6-(1-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,10,13,16,19,22-hexaen-24-yl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl)-2-hydroxyhexadecanimidic acid

C81H125N11O33 (1779.8441)

(13e)-16-(4-bromo-3-hydroxy-4-phenylbutan-2-yl)-10-[(3-chloro-4-methoxyphenyl)methyl]-9,12-dihydroxy-6-methyl-3-(2-methylpropyl)-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C35H44BrClN2O8 (734.1969)

(3s,6s,12s,15s,18s,23as)-6,12-bis[(2s)-butan-2-yl]-1,4,7,10,13,16-hexahydroxy-18-(3h-imidazol-4-ylmethyl)-3-(2-methylpropyl)-15-[2-(methylsulfanyl)ethyl]-3h,6h,9h,12h,15h,18h,21h,22h,23h,23ah-pyrrolo[1,2-a]1,4,7,10,13,16,19-heptaazacyclohenicosan-19-one

C36H59N9O7S (761.4258)

(2z,5r,8s,11r,12s,15s,18s,19s,22r)-15-(3-carbamimidamidopropyl)-2-ethylidene-3,6,9,13,16,20-hexahydroxy-18-[(1e,3e,5s,6s)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,5,12,19-tetramethyl-8-(2-methylpropyl)-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C50H76N10O12 (1008.5644)

(3s,6r,10r,13e,16s)-10-[(3-chloro-4-methoxyphenyl)methyl]-9,12-dihydroxy-6-methyl-16-[(2r,3e)-4-phenylbut-3-en-2-yl]-3-propyl-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C34H41ClN2O7 (624.2602)

{[(2r,3s,8r,13r,14s,19r)-8,19-bis(4,4-dichlorobutyl)-10,13,21,24,26-pentahydroxy-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaen-2-yl]oxy}methanimidic acid

C37H53Cl4NO7 (763.2576)

[(1s,5r,6s,10r,11s,15r,16s,20r,21s,25r,26s,30r,31s,35r,36r,37r,38r,39r,40r,41r,42r,43r,44r,45r,46r,47r,48r,49r)-35-[(acetyloxy)methyl]-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,15,20,25,30-pentakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.2³,⁶.2⁸,¹¹.2¹³,¹⁶.2¹⁸,²¹.2²³,²⁶.2²⁸,³¹]nonatetracontan-5-yl]methyl acetate

C46H74O37 (1218.3909)

3-[(3r,4r,7s,13s,16s,19s,25s,28s,33as)-10-ethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-28-(c-hydroxycarbonimidoylmethyl)-13,16-bis[(1r)-1-hydroxyethyl]-7-isopropyl-25-[(1r)-1-methoxyethyl]-27-methyl-26,29-dioxo-3-[(2s)-13-oxohexadecan-2-yl]-3h,4h,7h,13h,16h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-19-yl]propanimidic acid

C58H98N12O17 (1234.7173)

9,12-dihydroxy-10-[(4-hydroxyphenyl)methyl]-6-methyl-3-(2-methylpropyl)-16-(4-phenylbut-3-en-2-yl)-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C34H42N2O7 (590.2992)

(3s,6r,10r,13e,16s)-10-[(3-chloro-4-hydroxyphenyl)methyl]-9,12-dihydroxy-6-methyl-3-(2-methylpropyl)-16-[(1s)-1-[(2r,3r)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C34H41ClN2O8 (640.2551)

{[(2r,3s,8r,13r,14s,19s)-19-butyl-8-(4,4-dibromobutyl)-10,13,21,24,26-pentahydroxy-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaen-2-yl]oxy}methanimidic acid

C37H55Br2NO7 (783.2345)

3-[(3r,6s,9r,13s,16r,19s,22r,25r,28s,31r,34s,39as)-1,4,7,11,14,17,20,23,29,32-decahydroxy-31-[(r)-hydroxy(c-hydroxycarbonimidoyl)methyl]-16,22-bis[(1s)-1-hydroxy-2-methylpropyl]-6,34-bis[(1r)-1-hydroxyethyl]-13-isopropyl-19,27-dimethyl-3-(2-methylpropyl)-26,35-dioxo-9-pentyl-28-(sec-butyl)-3h,6h,9h,10h,13h,16h,19h,22h,25h,28h,31h,34h,37h,38h,39h,39ah-pyrrolo[2,1-i]1,4,7,10,13,16,19,22,25,28,31,34-dodecaazacycloheptatriacontan-25-yl]propanimidic acid

C63H110N14O19 (1366.8071)

3-[(6r,13s,19r,22s,25e,28s,31r,34s,37s)-34-benzyl-19,31-bis[(2s)-butan-2-yl]-25-ethylidene-5,8,9,12,21,24,27,30,33,36-decahydroxy-10-(2-hydroxyheptyl)-22,28-bis(hydroxymethyl)-2,18-dioxo-1,4,7,11,17,20,23,26,29,32,35-undecaazatricyclo[35.3.0.0¹³,¹⁷]tetraconta-4,7,11,20,23,26,29,32,35-nonaen-6-yl]propanimidic acid

C58H90N12O16 (1210.6597)

3-{[2-benzyl-15-(4-carbamimidoylbutyl)-6,13,16,21-tetrahydroxy-5-[2-(4-hydroxyphenyl)ethyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-10-oxa-2,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-c-hydroxycarbonimidoyl}-3-[(1-hydroxybutylidene)amino]propanoic acid

C49H69N9O13 (991.5015)

8,19-bis(4-hydroxybutyl)-2,13-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaene-10,21,24,26-tetrol

C36H56O6 (584.4077)

2-[10,16-diethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-13,19-bis(c-hydroxycarbonimidoylmethyl)-25-(1-hydroxyethyl)-3-(12-hydroxytetradecan-2-yl)-7-isopropyl-22,27-dimethyl-26,29-dioxo-3h,4h,7h,13h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-28-yl]ethanimidic acid

C55H91N13O16 (1189.6706)

n-[(1e,3r,4r,5r,9s,10s,11s)-11-[(1s,3s,4s,5s,7r,8s,9r,12e,14e,16s,17r,19r)-3,16-dihydroxy-5,7,17-trimethoxy-8,14-dimethyl-11-oxo-10,23-dioxaspiro[bicyclo[17.3.1]tricosane-4,2'-oxirane]-12,14,20-trien-9-yl]-10-hydroxy-4-methoxy-3,5,9-trimethyl-6-oxododec-1-en-1-yl]-n-methylformamide

C45H73NO13 (835.5082)

(2s,5r,8s,11r,15s,18s,19s,22r)-3,6,9,13,16,20,25-heptahydroxy-2-(hydroxymethyl)-18-[(1e,3e,5s,6s)-6-methoxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-8,15-bis(3-methoxy-3-oxopropyl)-5,19-dimethyl-1,4,7,10,14,17,21-heptaazacyclopentacosa-1(25),3,6,9,13,16,20-heptaene-11,22-dicarboxylic acid

C47H67N7O17 (1001.4593)

3-({2-[(2-{[1,3-dihydroxy-2-({1,3,5-trihydroxy-5-[2-(2-hydroxyphenyl)-4,5-dihydro-1,3-oxazol-4-yl]pentylidene}amino)butylidene]amino}-1,3-dihydroxypropylidene)amino]-1,3-dihydroxypropylidene}amino)-6,7-dihydroxy-1,1-dimethyl-3,4-dihydro-2h-quinolin-1-ium

[C35H49N6O13]+ (761.3357)

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

C44H63N7O11S (897.4306)

(1s,5s,6r,8r,10r,12s)-n-[2-(1-carbamimidoyl-2,5-dihydropyrrol-3-yl)ethyl]-10-{[(2s,3r,4s,5r,6r)-3-(hexanoyloxy)-5-hydroxy-4-(c-hydroxycarbonimidoyloxy)-6-(hydroxymethyl)oxan-2-yl]oxy}-3,12-dihydroxy-7-[(2r)-2-{[1-hydroxy-2-methoxy-3-(sulfooxy)propylidene]amino}-4-methylpentanoyl]-2-oxa-4,7-diazatricyclo[6.3.1.0¹,⁵]dodec-3-ene-6-carboximidic acid

C40H64N8O19S (992.4008)

(1s,5r,6s,10r,11s,15r,16s,20r,21s,25r,26s,30r,31s,35r,36s,40r,41r,42r,43r,44r,45r,46r,47r,48r,49r,50r,51r,52r,53r,54r,55r,56r)-5,10,15,20,25,30,35,40-octakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34,37,39-hexadecaoxanonacyclo[36.2.2.2³,⁶.2⁸,¹¹.2¹³,¹⁶.2¹⁸,²¹.2²³,²⁶.2²⁸,³¹.2³³,³⁶]hexapentacontane-41,42,43,44,45,46,47,48,49,50,51,52,53,54,55,56-hexadecol

C48H80O40 (1296.4226)

3-phenyl-2-[({2,5,11,14-tetrahydroxy-3,9-bis[2-(4-hydroxyphenyl)ethyl]-7-methyl-8-oxo-12-(sec-butyl)-1,4,7,10,13-pentaazacyclononadeca-1,4,10,13-tetraen-15-yl}-c-hydroxycarbonimidoyl)amino]propanoic acid

C45H59N7O10 (857.4323)

(2s)-2-({hydroxy[(1s,4s,10s,13s,19s,22s,25s,29r,30s,33s,44s)-2,11,21,24,31,34,41,46,48-nonahydroxy-30-{[(2s)-1-hydroxy-2-({hydroxy[(2s)-1-[(2s)-2-[(1-hydroxyethylidene)amino]-3-(4-hydroxyphenyl)propanoyl]pyrrolidin-2-yl]methylidene}amino)-4-(c-hydroxycarbonimidoyl)butylidene]amino}-4-[(4-hydroxyphenyl)methyl]-22-(1h-indol-3-ylmethyl)-29-methyl-33-(2-methylpropyl)-5,16,27-trioxo-15,28-dioxa-3,6,12,20,23,32,35,40,45,47-decaazatetracyclo[17.16.11.2¹³,²⁵.0⁶,¹⁰]octatetraconta-2,11,20,23,31,34,40,45,47-nonaen-44-yl]methylidene}amino)-3-(4-hydroxyphenyl)propanoic acid

C88H111N17O25 (1805.7937)

2-{[hydroxy({2,5,8,13,20,29,32,39,42-nonahydroxy-38-[(1-hydroxy-2-{[hydroxy(1-{2-[(1-hydroxyethylidene)amino]-3-(4-hydroxyphenyl)propanoyl}pyrrolidin-2-yl)methylidene]amino}-4-(c-hydroxycarbonimidoyl)butylidene)amino]-31-(hydroxymethyl)-22-[(4-hydroxyphenyl)methyl]-4-(1h-indol-3-ylmethyl)-7-(3-methoxy-3-oxopropyl)-37-methyl-41-(2-methylpropyl)-23,35-dioxo-36-oxa-3,6,9,14,21,24,30,33,40,43-decaazatricyclo[17.14.10.0²⁴,²⁸]tritetraconta-2,5,8,13,20,29,32,39,42-nonaen-10-yl})methylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

C89H115N17O26 (1837.8199)

3-[(6r,13s,19r,22s,25e,28s,31r,34s,37s)-34-benzyl-19,31-bis[(2s)-butan-2-yl]-25-ethylidene-5,8,9,12,21,24,27,30,33,36-decahydroxy-10-(2-hydroxyheptyl)-22,28-bis(hydroxymethyl)-39-methyl-2,18-dioxo-1,4,7,11,17,20,23,26,29,32,35-undecaazatricyclo[35.3.0.0¹³,¹⁷]tetraconta-4,7,11,20,23,26,29,32,35-nonaen-6-yl]propanimidic acid

C59H92N12O16 (1224.6754)

(31z)-6-benzyl-31-ethylidene-24-heptyl-1,4,7,10,13,16,19,22,26,29,35-undecahydroxy-3,28-bis(2-hydroxyethyl)-9,18-bis(2-methylpropyl)-12,15-bis(sec-butyl)-3h,6h,9h,12h,15h,18h,21h,24h,25h,28h,34h,35h,36h,36ah-pyrrolo[1,2-g]1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotetratriacontan-32-one

C62H101N11O14 (1223.7529)

(12r,13s)-12,13-dihydroxyoctadeca-9,10-dienoic acid

C18H32O4 (312.23)

n-sulfo{[(3as,4r,10as)-10,10-dihydroxy-2,6-diimino-hexahydro-1h-pyrrolo[1,2-c]purin-4-yl]methoxy}carboximidic acid

C10H17N7O7S (379.091)

(4s)-4,7,11,18-tetramethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaene-2,9,16-triol

C19H20N6O4S2 (460.0987)

n-[(1e,3r,4r,5r,9s,10s,11s)-11-[(1s,3s,4s,5s,7r,8s,9r,12e,16s,17r,19r)-3,16-dihydroxy-5,7,17-trimethoxy-8,14-dimethyl-11-oxo-10,23-dioxaspiro[bicyclo[17.3.1]tricosane-4,2'-oxirane]-12,14,20-trien-9-yl]-10-hydroxy-4-methoxy-3,5,9-trimethyl-6-oxododec-1-en-1-yl]-n-methylformamide

C45H73NO13 (835.5082)

[(1s,5r,6s,10r,11s,15r,16s,20r,21s,25r,26s,30r,31r,32r,33r,34r,35r,36r,37r,38r,39r,40r,41r,42r)-15,20,25-tris[(acetyloxy)methyl]-31,32,33,34,35,36,37,38,39,40,41,42-dodecahydroxy-10,30-bis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29-dodecaoxaheptacyclo[26.2.2.2³,⁶.2⁸,¹¹.2¹³,¹⁶.2¹⁸,²¹.2²³,²⁶]dotetracontan-5-yl]methyl acetate

C44H68O34 (1140.3592)

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

C41H60N8O10 (824.4432)

(5r,8s,11r,15s,18s,19s,22r)-18-[(1e,3e,5s,6s)-6-(acetyloxy)-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-15-(4-carbamimidamidobutyl)-3,6,9,13,16,20-hexahydroxy-1,5,19-trimethyl-2-methylidene-8-(2-methylpropyl)-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C50H74N10O13 (1022.5437)

3-imino-4a,6a,9,9,12a,14a-hexamethyl-1h,2h,4h,5h,6h,7h,8h,8ah,10h,11h,12h,13h,14h,14bh-phenanthro[2,1-f]quinazolin-13-ol

C26H43N3O (413.3406)

(5r,8s,11r,12s,15s,18s,19s,22r)-18-[(1e,3e,5s,6s)-6-(acetyloxy)-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-15-(3-carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-1,5,12,19-tetramethyl-8-[(2s)-2-methylbutyl]-2-methylidene-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C51H76N10O13 (1036.5593)

7-methylpyrazolo[4,3-e][1,2,4]triazin-3-ol

C5H5N5O (151.0494)

(3s,6r,10r,13e,16s)-10-[(3,5-dichloro-4-hydroxyphenyl)methyl]-9,12-dihydroxy-6-methyl-3-(2-methylpropyl)-16-[(1s)-1-[(2r,3r)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C34H40Cl2N2O8 (674.2162)

3-[(3s,6s,12s,18s,21s,24s,27s,30s,33s)-21-[(2s)-butan-2-yl]-5,14,17,20,23,26,29,32-octahydroxy-30-[(1r)-1-hydroxyethyl]-12,27-bis(hydroxymethyl)-18-(1h-indol-3-ylmethyl)-3-isopropyl-2,11-dioxo-1,4,10,13,16,19,22,25,28,31-decaazatricyclo[31.3.0.0⁶,¹⁰]hexatriaconta-4,13,16,19,22,25,28,31-octaen-24-yl]propanimidic acid

C49H72N12O14 (1052.5291)

(2r,3s,8s,13r,14s,19s)-13-(acetyloxy)-8,19-dibutyl-10,21,24,26-tetrahydroxy-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaen-2-yl acetate

C40H60O8 (668.4288)

(5r,8s,11r,15s,18s,19s,22r)-18-[(1e,3e,5s,6s)-6-(acetyloxy)-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-8,15-bis(3-carbamimidamidopropyl)-2-ethylidene-3,6,9,13,16,20,25-heptahydroxy-5,19-dimethyl-1,4,7,10,14,17,21-heptaazacyclopentacosa-1(25),3,6,9,13,16,20-heptaene-11,22-dicarboxylic acid

C49H73N13O13 (1051.5451)

3-{[(3r,3ar,5ar,6r,7r,9as,9br)-3-carboxy-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid

C27H38O5 (442.2719)

(4r,11s,14s,17r)-14-[(1r)-1-hydroxyethyl]-4,17-dimethyl-11-(2-methylpropyl)-6,19-dithia-3,10,13,16,21,22-hexaazatricyclo[16.2.1.1⁵,⁸]docosa-1(20),2,5(22),7,9,12,15,18(21)-octaene-2,9,12,15-tetrol

C22H30N6O5S2 (522.1719)

(2r,3s,8s,14s,19s)-8,19-dibutyl-10,21,24,26-tetrahydroxy-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaen-2-yl acetate

C38H58O6 (610.4233)

(2r,3s,8s,14s,19s)-8,19-dibutyl-3,14-dimethyl-2-{[(2s,3r,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}tricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaene-10,21,24,26-tetrol

C41H64O9 (700.455)

(1r,2s,7s)-7-{4-[(1r,2s)-7-chloro-2-methyl-1-{[(2s,3r,4r,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}undecyl]-2,6-dihydroxyphenyl}-1-(3,5-dihydroxyphenyl)-2-methylundecyl acetate

C43H67ClO11 (794.4372)

3-{[(3r,3ar,5as,6r,7r,9as,9br)-3-(hydroxymethyl)-3,3a,6,7,9a-pentamethyl-octahydro-1h-cyclopenta[a]naphthalen-6-yl]methyl}-4-hydroxybenzoic acid

C27H40O4 (428.2926)

3-[(3r,4r,7s,10e,13s,16s,19s,25s,28s,33as)-10-ethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-28-(c-hydroxycarbonimidoylmethyl)-16-[(1r)-1-hydroxyethyl]-7,13-diisopropyl-25-[(1r)-1-methoxyethyl]-27-methyl-26,29-dioxo-3-[(2s)-13-oxohexadecan-2-yl]-3h,4h,7h,13h,16h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-19-yl]propanimidic acid

C59H100N12O16 (1232.738)

(5r,8s,11r,12s,15s,18s,19s,22r)-18-[(1e,3e,5s,6s)-6-(acetyloxy)-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-15-(4-carbamimidamidobutyl)-3,6,9,13,16,20-hexahydroxy-1,5,12,19-tetramethyl-8-[(2s)-2-methylbutyl]-2-methylidene-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C52H78N10O13 (1050.575)

(3as,4r,10s,10as)-4-(hydroxymethyl)-2,6-diimino-octahydropyrrolo[1,2-c]purin-10-ol

C9H16N6O2 (240.1335)

(3s,6r,10r,13e,16s)-10-[(3,5-dichloro-4-methoxyphenyl)methyl]-9,12-dihydroxy-6-methyl-3-(2-methylpropyl)-16-[(1s)-1-[(2r,3r)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C35H42Cl2N2O8 (688.2318)

[(1s,5r,6s,10r,11s,15r,16s,20r,21s,25r,26s,30r,31s,35r,36r,37r,38r,39r,40r,41r,42r,43r,44r,45r,46r,47r,48r,49r)-15,20-bis[(acetyloxy)methyl]-36,37,38,39,40,41,42,43,44,45,46,47,48,49-tetradecahydroxy-10,25,30,35-tetrakis(hydroxymethyl)-2,4,7,9,12,14,17,19,22,24,27,29,32,34-tetradecaoxaoctacyclo[31.2.2.2³,⁶.2⁸,¹¹.2¹³,¹⁶.2¹⁸,²¹.2²³,²⁶.2²⁸,³¹]nonatetracontan-5-yl]methyl acetate

C48H76O38 (1260.4014)

3-{[(1r,2r,4br,7r,8as,10as)-7-hydroxy-1,2,4b,8,8-pentamethyl-3,5,6,7,8a,9,10,10a-octahydro-2h-phenanthren-1-yl]methyl}-4-hydroxybenzoic acid

C27H38O4 (426.277)

(4s,18r)-18-isopropyl-4,7-dimethyl-6-oxa-13,20-dithia-3,10,17,22,23,24-hexaazatetracyclo[17.2.1.1⁵,⁸.1¹²,¹⁵]tetracosa-1(21),2,5(24),7,9,12(23),14,16,19(22)-nonaene-2,9,16-triol

C20H22N6O4S2 (474.1144)

n-[(1e,3r,4r,5r,9s,10s,11s)-10-hydroxy-4-methoxy-3,5,9-trimethyl-6-oxo-11-[(1s,3s,4s,5s,7r,8s,9r,12e,14e,16s,17r,19r)-4,16,17-trihydroxy-3,5,7-trimethoxy-4,8,14-trimethyl-11-oxo-10,23-dioxabicyclo[17.3.1]tricosa-12,14,20-trien-9-yl]dodec-1-en-1-yl]-n-methylformamide; n-[(1e,3r,4r,5r,9s,10s,11s)-11-[(1s,3s,4r,5s,7r,8s,9r,12e,14e,16s,17r,19r)-16,17-dihydroxy-4-(hydroxymethyl)-3,5,7-trimethoxy-8,14-dimethyl-11-oxo-10,23-dioxabicyclo[17.3.1]tricosa-12,14,20-trien-9-yl]-10-hydroxy-4-methoxy-3,5,9-trimethyl-6-oxododec-1-en-1-yl]-n-methylformamide

C90H150N2O26 (1675.0476)

(5r,8s,11r,12s,15s,18s,19s,22r)-15-(3-carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-18-[(1e,3e,5s,6s)-6-hydroxy-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-1,5,12,19-tetramethyl-8-[(2s)-2-methylbutyl]-2-methylidene-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C49H74N10O12 (994.5487)

(2r,3s,5s)-2-{[(2r,5s)-2-{[(2r,3s,5s)-2-[(2-{[(2s,3r,4r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl)oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C30H52O26 (828.2747)

2-[(3,4-dihydroxy-5-{4-imino-3h,5h-pyrrolo[3,2-d]pyrimidin-7-yl}oxolan-2-yl)methoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

C17H24N4O9 (428.1543)

3-[(3r,4r,7s,10e,13s,16s,19s,25s,28s,33as)-10-ethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-28-(c-hydroxycarbonimidoylmethyl)-13-[(1s)-1-hydroxyethyl]-7,16-diisopropyl-25-[(1s)-1-methoxyethyl]-27-methyl-26,29-dioxo-3-[(2s)-12-oxohexadecan-2-yl]-3h,4h,7h,13h,16h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-19-yl]propanimidic acid

C59H100N12O16 (1232.738)

(2s)-n-(5-carbamimidamido-1-oxopentan-2-yl)-2-[(2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-1-hydroxy-4-phenylbutylidene)amino]-4-methylpentanimidic acid

C31H44N6O6 (596.3322)

(2s)-2-[(1-hydroxybutylidene)amino]-3-methyl-n-[(7s,13s,16s,22s,27s,32s)-15,18,21,24,29-pentahydroxy-16-(c-hydroxycarbonimidoylmethyl)-13-[(4-hydroxyphenyl)methyl]-32-methyl-22,27-bis(2-methylpropyl)-2,6,12,26-tetraoxo-5-oxa-1,11,14,17,20,23,28-heptaazatricyclo[28.3.0.0⁷,¹¹]tritriaconta-14,17,20,23,28-pentaen-3-yl]butanimidic acid

C52H78N10O14 (1066.5699)

3-[(3r,4r,7s,10e,13s,16s,19s,25s,28s,33as)-10-ethylidene-1,4,5,8,11,14,17,20,23-nonahydroxy-28-(c-hydroxycarbonimidoylmethyl)-13,16-bis[(1r)-1-hydroxyethyl]-3-[(2s)-13-hydroxyhexadecan-2-yl]-7-isopropyl-25-[(1r)-1-methoxyethyl]-27-methyl-26,29-dioxo-3h,4h,7h,13h,16h,19h,22h,25h,28h,31h,32h,33h,33ah-pyrrolo[2,1-c]1,4,7,10,13,16,19,22,25,28-decaazacyclohentriacontan-19-yl]propanimidic acid

C58H100N12O17 (1236.7329)

{[8,19-dibutyl-10,21,24,26-tetrahydroxy-13-(c-hydroxycarbonimidoyloxy)-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaen-2-yl]oxy}methanimidic acid

C38H58N2O8 (670.4193)

8-(4-chlorobutyl)-19-(4,4-dichlorobutyl)-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaene-2,10,13,21,24,26-hexol

C36H53Cl3O6 (686.2908)

(2s,3r)-2-{[(5r)-3-[(carboxymethyl)imino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-1-en-1-yl]amino}-3-hydroxybutanoic acid

C14H22N2O8 (346.1376)

3-({2,5-dibenzyl-6,13,16,21-tetrahydroxy-15-[(4-hydroxyphenyl)methyl]-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl}-c-hydroxycarbonimidoyl)-3-[(1-hydroxybutylidene)amino]propanoic acid

C50H63N7O13 (969.4484)

(3s,6r,10s,13e,16s)-10-[(3-chloro-4-methoxyphenyl)methyl]-9,12-dihydroxy-6-methyl-3-(2-methylpropyl)-16-[(1s)-1-[(2r,3r)-3-phenyloxiran-2-yl]ethyl]-1,4-dioxa-8,11-diazacyclohexadeca-8,11,13-triene-2,5-dione

C35H43ClN2O8 (654.2708)

[(4s,5r,6s,8s,10r)-10-[(r)-hydroxy(2-hydroxy-6-oxo-1h-pyrimidin-4-yl)methyl]-5-methyl-2,11,12-triazatricyclo[6.3.1.0⁴,¹²]dodec-1-en-6-yl]oxidanesulfonic acid

C15H21N5O7S (415.1162)

n-[2-(3-chloro-4-methoxyphenyl)-1-[(3-methoxy-2-methyl-3-oxopropyl)-c-hydroxycarbonimidoyl]ethyl]-5-[(2-hydroxy-4-methylpentanoyl)oxy]-6-(3-phenyloxiran-2-yl)hept-2-enimidic acid

C36H47ClN2O9 (686.297)

2-({8,19-dibutyl-4,15-dichloro-21,24,26-trihydroxy-2,13-dimethoxytricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9(26),10,12(25),20,23-hexaen-10-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C42H64Cl2O11 (814.3825)

(2e)-n-[2-(3-chloro-4-methoxyphenyl)-1-{[2-methyl-2-(methyl-c-hydroxycarbonimidoyl)ethyl]-c-hydroxycarbonimidoyl}ethyl]-5-[(2-hydroxy-4-methylpentanoyl)oxy]-6-(3-phenyloxiran-2-yl)hept-2-enimidic acid

C36H48ClN3O8 (685.313)

(2s)-n-(1-{[(2s,8s,11r,12s)-2,5-dibenzyl-6,13,16,21-tetrahydroxy-15-(2-hydroxyethyl)-8-isopropyl-4,11-dimethyl-3,9,22-trioxo-10-oxa-1,4,7,14,17-pentaazabicyclo[16.3.1]docosa-6,13,16-trien-12-yl]-c-hydroxycarbonimidoyl}-3-hydroxypropyl)-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-3-methylpentanimidic acid

C56H76N8O15 (1100.543)

3-{[(2s,3s,4r,5r)-4-{[(2r,3s,4s,5r,6s)-4,5-dihydroxy-3-[(1-hydroxyethylidene)amino]-6-(hydroxymethyl)oxan-2-yl]oxy}-3,5-dihydroxyoxan-2-yl]oxy}-n-(1-{[(3s,12r,15z,18r,21s,24s,25r)-15-ethylidene-5,11,14,17,20,23-hexahydroxy-12-[2-(c-hydroxycarbonimidoyl)ethyl]-21-[(1s)-1-hydroxyethyl]-3,18-bis[(4-hydroxyphenyl)methyl]-7,25-dimethyl-2,8-dioxo-6-(1-{[(2r,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)-1-oxa-4,7,10,13,16,19,22-heptaazacyclopentacosa-4,10,13,16,19,22-hexaen-24-yl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl)-2-hydroxytetradecanimidic acid

C79H121N11O33 (1751.8128)

(2z,5r,8s,11r,15s,18s,19s,22r)-18-[(1e,3e,5s,6s)-6-(acetyloxy)-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-8,15-bis(3-carbamimidamidopropyl)-2-ethylidene-3,6,9,13,16,20,25-heptahydroxy-5,19-dimethyl-1,4,7,10,14,17,21-heptaazacyclopentacosa-1(25),3,6,9,13,16,20-heptaene-11,22-dicarboxylic acid

C49H73N13O13 (1051.5451)

18-[6-(acetyloxy)-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-15-(3-carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-1,5,19-trimethyl-2-methylidene-8-(2-methylpropyl)-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C49H72N10O13 (1008.528)

1-{4-[11-(acetyloxy)-11-(3,5-dihydroxyphenyl)-10-methylundecan-5-yl]-3,5-dihydroxyphenyl}-7-chloro-2-methylundecyl acetate

C40H61ClO8 (704.4055)

5-{[(1e)-3-[(4-carboxy-4-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}butyl)amino]-5-({[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxyoxan-2-yl)oxy]oxan-2-yl]oxy}methyl)-5-hydroxy-2-methoxycyclohex-3-en-1-ylidene]amino}-2-{[5-hydroxy-5-(hydroxymethyl)-2-methoxy-3-oxocyclohex-1-en-1-yl]amino}pentanoic acid

C45H70N4O24 (1050.438)

{[8,19-bis(4,4-dibromobutyl)-10,13,21,24,26-pentahydroxy-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaen-2-yl]oxy}methanimidic acid

C37H53Br4NO7 (939.0555)

{[(2r,3s,8s,13r,14s,19s)-8-butyl-19-(4-chlorobutyl)-10,21,24,26-tetrahydroxy-13-(c-hydroxycarbonimidoyloxy)-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaen-2-yl]oxy}methanimidic acid

C38H57ClN2O8 (704.3803)