NCBI Taxonomy: 1177

Isofucosterol

C29H48O (412.3705)

Isofucosterol, also known as delta5-avenasterol, is a phytosterol. Phytosterols, or plant sterols, are compounds that occur naturally and bear a close structural resemblance to cholesterol but have different side-chain configurations. Phytosterols are relevant in pharmaceuticals (production of therapeutic steroids), nutrition (anti-cholesterol additives in functional foods, anti-cancer properties), and cosmetics (creams, lipstick). Phytosterols can be obtained from vegetable oils or from industrial wastes, which gives an added value to the latter. Considerable efforts have been recently dedicated to the development of efficient processes for phytosterol isolation from natural sources. The present work aims to summarize information on the applications of phytosterols and to review recent approaches, mainly from the industry, for the large-scale recovery of phytosterols (PMID: 17123816, 16481154). Isofucosterol is found to be associated with phytosterolemia, which is an inborn error of metabolism. Isofucosterol, also known as (24z)-stigmasta-5,24(28)-dien-3-ol or delta5-avenasterol, belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24. Thus, isofucosterol is considered to be a sterol lipid molecule. Isofucosterol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Isofucosterol can be found in a number of food items such as globe artichoke, gooseberry, deerberry, and ucuhuba, which makes isofucosterol a potential biomarker for the consumption of these food products. Isofucosterol can be found primarily in blood. Moreover, isofucosterol is found to be associated with sitosterolemia. Isofucosterol is a 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). The double bond at postion 24(28) adopts a Z-configuration. It has a role as an animal metabolite, a plant metabolite, an algal metabolite and a marine metabolite. It is a 3beta-sterol, a 3beta-hydroxy-Delta(5)-steroid, a C29-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Fucosterol is a natural product found in Echinometra lucunter, Ulva fasciata, and other organisms with data available. A 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). The double bond at postion 24(28) adopts a Z-configuration. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research. Isofucosterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=481-14-1 (retrieved 2024-10-08) (CAS RN: 481-14-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Stigmasterol

C29H48O (412.3705)

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

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].

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

beta-Carboline

C11H8N2 (168.0687)

beta-Carboline, also known as norharmane, is an organic amine and is the prototype of a class of compounds known as beta-carbolines. beta-Carbolines are compounds containing a 9H-pyrido[3,4-b]indole moiety. beta-Carboline is a very strong basic compound (based on its pKa). beta-Carboline alkaloids are widely distributed in plants and animals and many are inverse agonists of the GABA-A receptor complex (PMID: 17334612). Other biological activities demonstrated by these compounds include intercalation; inhibition of CDK, topoisomerase, and monoamine oxidase; and interaction with 5-hydroxy serotonin receptors. These compounds have also exhibited sedative, anxiolytic, hypnotic, anticonvulsant, antitumor, antiviral, antiparasitic, and antimicrobial activities (PMID: 17305548). b-Carboline (9H-pyrido[3,4-b]indole) is an organic amine that is the prototype of a class of compounds known as b-carbolines. [HMDB]. Norharman is found in chicory. CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 75 CONFIDENCE standard compound; INTERNAL_ID 2883 D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens 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].

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.

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].

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

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)

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].

Nostofungicidine

C48H76N10O18 (1080.5339)

4,5-dihydroxy-1-methyl-anthraquinone

C15H10O4 (254.0579)

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].

Nostocine A

C5H5N5O (151.0494)

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].

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].

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].

Norharman

C11H8N2 (168.0687)

D009676 - Noxae > D009498 - Neurotoxins D009676 - Noxae > D009153 - Mutagens Annotation level-1 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].

1-(O-alpha-D-glucopyranosyl)-(1,3R,25R)-hexacosanetriol

C32H64O8 (576.4601)

Erlose

C18H32O16 (504.169)

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)

Stigmasterin

C29H48O (412.3705)

C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

Lanol

C27H46O (386.3548)

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].

474-67-9

C28H46O (398.3548)

C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol 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].

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

Tenuecyclamide C

C20H22N6O4S3 (506.0865)

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)

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)

{[(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)

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)

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)

(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)

(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)

(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)

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-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)

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)

(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)

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

C18H11NO3 (289.0739)

(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)

(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)

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-{[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)

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)

(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)

(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)

(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)

(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)

(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-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)

(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)

(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)

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)

(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)

{[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)

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)

(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)

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)

3-({2-benzyl-6,13,16,21-tetrahydroxy-5-[2-(4-hydroxyphenyl)ethyl]-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-hydroxyhexylidene)amino]propanoic acid

C53H69N7O14 (1027.4902)

(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]-8-{[(1s,4r)-4-hydroxycyclohex-2-en-1-yl]methyl}-1,5,12,19-tetramethyl-2-methylidene-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C51H74N10O13 (1034.5437)

(2s,8r,13s,19r)-2,13-dibutyl-11,22,23-trihydroxy-8,19-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9(26),11,20,23-pentaene-10,25-dione

C36H54O5 (566.3971)

(3s,6r,10r,13z,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)

(11s,14s)-14-(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)

3-{[2-benzyl-15-(3-carbamimidamidopropyl)-6,13,16,21-tetrahydroxy-5-[(4-hydroxyphenyl)methyl]-4,11-dimethyl-3,9,22-trioxo-8-(sec-butyl)-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

C48H68N10O13 (992.4967)

(3s,6r,10s,13e,16s)-10-[(3-chloro-4-methoxyphenyl)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

C35H43ClN2O7 (638.2759)

{[(2r,3s,8s,13r,14s,19s)-8-butyl-19-(4,4-dichlorobutyl)-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

C38H56Cl2N2O8 (738.3414)

(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]-6-(hydroxymethyl)oxane-3,4,5-triol

C18H32O16 (504.169)

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

C44H57N7O11 (859.4116)

18-[6-(acetyloxy)-3,5-dimethyl-7-phenylhepta-1,3-dien-1-yl]-15-(3-carbamimidamidopropyl)-3,6,9,13,16,20-hexahydroxy-1,5,12,19-tetramethyl-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)

2-{[(1e)-3-[(carboxymethyl)amino]-5-hydroxy-5-(hydroxymethyl)-2-methoxycyclohex-2-en-1-ylidene]amino}-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}butanoic acid

C20H32N2O13 (508.1904)

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

C36H62O31 (990.3275)

3-{[2,5-dibenzyl-15-(4-carbamimidoylbutyl)-6,13,16,21-tetrahydroxy-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-hydroxyoctylidene)amino]propanoic acid

C52H75N9O12 (1017.5535)

2-({5-[(carboxymethyl)imino]-3-hydroxy-6-methoxy-3-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}cyclohex-1-en-1-yl}amino)-3-hydroxybutanoic acid

C19H30N2O12 (478.1799)

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

C22H35N5O5 (449.2638)

(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)

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

C27H38O5 (442.2719)

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

C36H56O4 (552.4178)

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-hydroxybutylidene)amino]propanoic acid

C47H66N10O12 (962.4861)

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)

(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}-3-methylbutanimidic acid

C30H42N6O7 (598.3115)

(5r,8s,11r,12s,15s,18s,19s,22r)-8-benzyl-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-2-methylidene-25-oxo-1,4,7,10,14,17,21-heptaazacyclopentacosa-3,6,9,13,16,20-hexaene-11,22-dicarboxylic acid

C51H70N10O12 (1014.5174)

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

C36H55ClO5 (602.3738)

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

C22H35N5O5 (449.2638)

(2r,3s,8s,13r,14s,19s)-8,19-dibutyl-3,14-dimethyl-2,13-bis({[(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

C46H72O14 (848.4922)

(2s)-n-[(1s,7s,11s,13s,21s,23s,26r,29s,32s,39r)-29-[(2s)-butan-2-yl]-24,27,30,33,39-pentahydroxy-35-(hydroxymethyl)-32-[(4-hydroxyphenyl)methyl]-11,21-dimethyl-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

C61H86N10O15 (1198.6274)

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

C47H71N13O12 (1009.5345)

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

C28H43N5O6 (545.3213)

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

C36H55ClO5 (602.3738)

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

C34H41ClN2O8 (640.2551)

(2r,3s,8s,13r,14s,19r)-8-butyl-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

C36H54Cl2O6 (652.3297)

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

C27H38O4 (426.277)

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

C31H44N6O6 (596.3322)

(3s)-3-{[(2s,5s,8s,11r,12s,15s,18s,21r)-2-benzyl-8-[(2s)-butan-2-yl]-15-(3-carbamimidamidopropyl)-6,13,16,21-tetrahydroxy-5-[(4-hydroxyphenyl)methyl]-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

C48H68N10O13 (992.4967)

(2r,4r,8s,13r,15r,19s)-8,19-dibutyl-4,15-dichloro-2,13-dimethoxytricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaene-10,21,24,26-tetrol

C36H54Cl2O6 (652.3297)

(2s)-2-{[(2s)-2-[(2s,3s)-2-[(2s)-2-{[(2s,3s)-3-amino-1,2-dihydroxyoctylidene]amino}-n,3-dimethylbutanamido]-n,3-dimethylpentanamido]-1-hydroxy-3-(4-hydroxyphenyl)propylidene]amino}-3-(4-hydroxyphenyl)propanoic acid

C39H59N5O9 (741.4313)

(3s,8s,14s,19s)-8,19-dibutyl-3,14-dimethyltricyclo[18.2.2.2⁹,¹²]hexacosa-1(22),9,11,20,23,25-hexaene-10,21,24,26-tetrol

C36H56O4 (552.4178)

6-({2-[(4-carbamimidamidobutyl)-c-hydroxycarbonimidoyl]-1-(2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-4-methylpentanoyl)-5-(hexanoyloxy)-octahydroindol-6-yl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

C41H64N6O14 (864.448)

(25r)-25-hydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexacosan-3-one

C32H62O8 (574.4444)

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

C29H44O5 (472.3189)

(2s)-n-(1-{[(2s,8s,11r,12s)-2-benzyl-6,13,16,21-tetrahydroxy-15-(2-hydroxyethyl)-5-[(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-hydroxypropyl)-2-{[1,2-dihydroxy-3-(4-hydroxyphenyl)propylidene]amino}-3-methylpentanimidic acid

C56H76N8O16 (1116.5379)

25-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}hexacosan-3-one

C32H62O8 (574.4444)

{[8,19-bis(4,4-dichlorobutyl)-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

C38H54Cl4N2O8 (806.2634)

3-[(3r,6r,9r,18s,25r)-6-benzyl-3-[(2s)-butan-2-yl]-5,8,17,20,21,24-hexahydroxy-2,14-dioxo-22-(5-phenylpentyl)-1,4,7,13,16,19,23-heptaazatricyclo[23.3.0.0⁹,¹³]octacosa-4,7,16,19,23-pentaen-18-yl]propanimidic acid

C46H64N8O9 (872.4796)

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

C35H43ClN2O7 (638.2759)

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

C34H40Cl2N2O8 (674.2162)

(4s,11s,18r)-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)

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

C27H38O4 (426.277)

2-[(1e,3e,5e,7e,9e,11e,13e,15e,17e,19e,21z)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,17,19,21,23-dodecaen-1-yl]-1,3,3-trimethylcyclohex-1-ene

C40H54 (534.4225)

{[(2r,3s,8s,13r,14s,19r)-19-(4-bromobutyl)-8-butyl-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

C38H57BrN2O8 (748.3298)