NCBI Taxonomy: 2791029

Bryopsidineae (ncbi_taxid: 2791029)

found 120 associated metabolites at suborder taxonomy rank level.

Ancestor: Bryopsidales

Child Taxonomies: Codiaceae, Derbesiaceae, Bryopsidaceae, Pseudobryopsidaceae

Stigmasterol

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

C29H48O (412.37049579999996)


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

   

Phytol

2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (theta-(theta,theta-(E)))-

C20H40O (296.307899)


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].

   

Stachydrine

(2S)-1,1-dimethylpyrrolidin-1-ium-2-carboxylate

C7H13NO2 (143.0946238)


Proline betaine is an osmoprotective compound found in urine. It is thought to serve an osmoprotective role for the kidney. Proline betaine is a glycine betaine analogue found in many citrus foods. Elevated levels of proline betaine in human urine are found after the consumption of citrus fruits and juices (PMID: 18060588). Proline betaine is a biomarker for the consumption of citrus fruits. Alkaloid from Citrus spp Medicago sativa and Stachys subspecies(alfalfa). L-Stachydrine or also called proline betaine is a biomarker for the consumption of citrus fruits. L-Stachydrine is found in many foods, some of which are capers, pulses, lemon, and alfalfa. Proline betaine, also known as stachydrine, belongs to the class of organic compounds known as proline and derivatives. Proline and derivatives are compounds containing proline or a derivative thereof resulting from reaction of proline at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom. Proline betaine exists in all living organisms, ranging from bacteria to humans. Proline betaine is found, on average, in the highest concentration within capers (Capparis spinosa). Proline betaine has also been detected, but not quantified in, several different foods, such as soy beans (Glycine max), crosnes (Stachys affinis), domestic pigs (Sus scrofa domestica), limes (Citrus aurantiifolia), and triticales (X Triticosecale rimpaui). This could make proline betaine a potential biomarker for the consumption of these foods. Proline betaine is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Proline betaine. Stachydrine is a major constituent of Chinese herb leonurus heterophyllus sweet used to promote blood circulation and dispel blood stasis. Stachydrine can inhibit the NF-κB signal pathway. Stachydrine is a major constituent of Chinese herb leonurus heterophyllus sweet used to promote blood circulation and dispel blood stasis. Stachydrine can inhibit the NF-κB signal pathway.

   

Cholesterol

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C27H46O (386.3548466)


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

   

Brassicasterol

(1S,2R,5S,10S,11S,14R,15R)-14-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C28H46O (398.3548466)


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].

   

Desmosterol

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

C27H44O (384.3391974)


Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is found in many foods, some of which are fig, sago palm, mexican groundcherry, and pepper (c. frutescens). Desmosterol is an intermediate in the synthesis of cholesterol. Desmosterolosis is a rare autosomal recessive inborn errors of cholesterol synthesis that is caused by defective activity of desmosterol reductase which results in an accumulation of demosterol (DHCR24, EC 1.3.1.72), combines a severe osteosclerotic skeletal dysplasia and includes 2-3 toe syndactyly with Smith-Lemli-Opitz syndrome (SLOS; the biochemical block in SLOS results in decreased cholesterol levels and increased 7-dehydrocholesterol levels). Desmosterolosis is caused by mutation of the 24-dehydrocholesterol reductase gene (DHCR24). Many of the malformations in SLOS and desmosterolosis are consistent with impaired hedgehog function. The hedgehog proteins include Sonic hedgehog (SHH), which plays a major role in midline patterning and limb development. Desmosterolosis, caused by defective activity of desmosterol reductase, combines a severe osteosclerotic skeletal dysplasia. 7-dehydrocholesterol reductase (DHCR7, EC 1.3.1.21) reduces the C7-C8 double bond in the sterol B ring to form cholesterol or desmosterol depending upon the precursor. Desmosterol can be converted to cholesterol by DHCR24. Therefore, SLOS and Desmosterolosis patients invariably have elevated levels of cholesterol precursors 7-dehydrocholesterol (and its spontaneous isomer 8-dehydrocholesterol) and absent desmosterol. (PMID: 14631207, 16207203). Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1]. Desmosterol is a molecule similar to cholesterol. Desmosterol is the immediate precursor of cholesterol in the Bloch pathway of cholesterol biosynthesis. Desmosterol, as an endogenous metabolite, used to study cholesterol metabolism[1].

   

Fucosterol

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

C29H48O (412.37049579999996)


Characteristic sterol of seaweeds; isolated from bladderwrack Fucus vesiculosus. Fucosterol is found in lemon grass and coconut. Fucosterol is found in coconut. Characteristic sterol of seaweeds; isolated from bladderwrack Fucus vesiculosu Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1]. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].

   

24-Methylenecholesterol

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

C28H46O (398.3548466)


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

   

epsilon-Carotene

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

C40H56 (536.4381776)


Epsilon-carotene is a member of the class of compounds known as carotenes. Carotenes are a type of unsaturated hydrocarbons containing eight consecutive isoprene units. They are characterized by the presence of two end-groups (mostly cyclohexene rings, but also cyclopentene rings or acyclic groups) linked by a long branched alkyl chain. Carotenes belonging form a subgroup of the carotenoids family. Epsilon-carotene can be found in a number of food items such as winged bean, enokitake, broad bean, and kiwi, which makes epsilon-carotene a potential biomarker for the consumption of these food products. Epsilon-carotene is a carotene .

   

Sceptrin

N-[[(1R,2S,3S,4R)-2,3-bis(2-amino-1H-imidazol-5-yl)-4-[[(4-bromo-1H-pyrrole-2-carbonyl)amino]methyl]cyclobutyl]methyl]-4-bromo-1H-pyrrole-2-carboxamide

C22H24Br2N10O2 (618.0450324)


   

Clionasterol

24beta-Ethyl-5-cholesten-3beta-ol

C29H50O (414.386145)


Clionasterol is a triterpenoid isolated from the Indian marine red alga Gracilaria edulis, the sponge Veronica aerophoba and the Kenyan Marine Green. Macroalga Halimeda macroloba. It is a potent inhibitor of complement component C1. (PMID 12624828). D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites

   

Poriferasterol

poriferasta-5,22E-dien-3β-ol

C29H48O (412.37049579999996)


   

Poriferasterol

14-(5-ethyl-6-methylhept-3-en-2-yl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-7-en-5-ol

C29H48O (412.37049579999996)


   

Siphonaxanthin

1-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-18-(4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-(hydroxymethyl)-7,12,16-trimethyloctadeca-3,5,7,9,11,13,15,17-octaen-2-one

C40H56O4 (600.4178376)


   

Loliolide

(6S,7aR)-6-hydroxy-4,4,7a-trimethyl-2,4,5,6,7,7a-hexahydro-1-benzofuran-2-one

C11H16O3 (196.1099386)


Loliolide, also known as (3s5r)-loliolide, is a member of the class of compounds known as benzofurans. Benzofurans are organic compounds containing a benzene ring fused to a furan. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Loliolide is soluble (in water) and an extremely weak acidic compound (based on its pKa). Loliolide can be found in sunflower, tea, and wakame, which makes loliolide a potential biomarker for the consumption of these food products.

   

Stachydrine

Pyrrolidinium, 2-carboxy-1,1-dimethyl-, inner salt, (2S)-

C7H13NO2 (143.0946238)


L-proline betaine is an amino acid betaine that is L-proline zwitterion in which both of the hydrogens attached to the nitrogen are replaced by methyl groups. It has a role as a food component, a plant metabolite and a human blood serum metabolite. It is a N-methyl-L-alpha-amino acid, an alkaloid and an amino-acid betaine. It is functionally related to a L-prolinium. It is a conjugate base of a N,N-dimethyl-L-prolinium. It is an enantiomer of a D-proline betaine. Stachydrine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Stachydrine is a natural product found in Teucrium polium, Halopithys incurva, and other organisms with data available. Proline betaine is an osmoprotective compound found in urine. It is thought to serve an osmoprotective role for the kidney. Proline betaine is a glycine betaine analogue found in many citrus foods. Elevated levels of proline betaine in human urine are found after the consumption of citrus fruits and juices (PMID: 18060588). Proline betaine is a biomarker for the consumption of citrus fruits. Alkaloid from Citrus spp Medicago sativa and Stachys subspecies(alfalfa). L-Stachydrine or also called proline betaine is a biomarker for the consumption of citrus fruits. L-Stachydrine is found in many foods, some of which are capers, pulses, lemon, and alfalfa. An amino acid betaine that is L-proline zwitterion in which both of the hydrogens attached to the nitrogen are replaced by methyl groups. Stachydrine is a major constituent of Chinese herb leonurus heterophyllus sweet used to promote blood circulation and dispel blood stasis. Stachydrine can inhibit the NF-κB signal pathway. Stachydrine is a major constituent of Chinese herb leonurus heterophyllus sweet used to promote blood circulation and dispel blood stasis. Stachydrine can inhibit the NF-κB signal pathway.

   
   

Discorhabdin C

Discorhabdin C

C18H13Br2N3O2 (460.9374438)


D009676 - Noxae > D011042 - Poisons > D008387 - Marine Toxins

   

siphonaxanthin

(3R,3R,6R)-7,8-Dihydro-8-oxo-beta,epsilon-carotene-3,3,19-triol

C40H56O4 (600.4178376)


   

sitosterol

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

C29H50O (414.386145)


A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

   

Betaine

2-(trimethylazaniumyl)acetate

C5H11NO2 (117.0789746)


Betaine or trimethylglycine is a methylated derivative of glycine. It functions as a methyl donor in that it carries and donates methyl functional groups to facilitate necessary chemical processes. The donation of methyl groups is important to proper liver function, cellular replication, and detoxification reactions. Betaine also plays a role in the manufacture of carnitine and serves to protect the kidneys from damage. Betaine has also been of interest for its role in osmoregulation. As a drug, betaine hydrochloride has been used as a source of hydrochloric acid in the treatment of hypochlorhydria. Betaine has also been used in the treatment of liver disorders, for hyperkalemia, for homocystinuria, and for gastrointestinal disturbances. (From Martindale, The Extra Pharmacopoeia, 30th Ed, p1341). Betaine is found in many foods, some of which are potato puffs, poppy, hazelnut, and garden cress. Betaine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=107-43-7 (retrieved 2024-06-28) (CAS RN: 107-43-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Stigmasterol

Stigmasterol

C29H48O (412.37049579999996)


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.

   

Fucosterol

(24E)-24-n-propylidenecholesterol;(3beta,24E)-stigmasta-5,24(28)-dien-3-ol;(E)-stigmasta-5,24(28)-dien-3beta-ol;24E-ethylidene-cholest-5-en-3beta-ol;fucosterin;trans-24-ethylidenecholesterol

C29H48O (412.37049579999996)


A 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28). (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol can be found in horseradish tree and sunflower, which makes (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol a potential biomarker for the consumption of these food products. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1]. Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].

   

Cholesterol

(1S,2R,5S,10S,11S,14R,15R)-2,15-dimethyl-14-[(2R)-6-methylheptan-2-yl]tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-7-en-5-ol

C27H46O (386.3548466)


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].

   

Brassicasterol

ergosta-5,22E-dien-3beta-ol

C28H46O (398.3548466)


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].

   

Phytol

2-Hexadecen-1-ol, 3,7,11,15-tetramethyl-, (theta-(theta,theta-(E)))-

C20H40O (296.307899)


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].

   

loliolide

2(4H)-Benzofuranone, 5,6,7,7a-tetrahydro-6-hydroxy-4,4,7a-trimethyl-, (6S-cis)-

C11H16O3 (196.1099386)


A natural product found in Brachystemma calycinum.

   
   

clionasterol

(3beta,24S)-stigmast-5-en-3-ol

C29H50O (414.386145)


A member of the class of phytosterols that is poriferast-5-ene carrying a beta-hydroxy substituent at position 3. D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites

   

2-aminoethanesulfonic acid

2-aminoethanesulfonic acid

C2H7NO3S (125.0146632)


   

epsilon-Carotene

(6R,6R)-epsilon,epsilon-Carotene

C40H56 (536.4381776)


   

2-trans,4-trans-Xanthoxin

2-trans,4-trans-Xanthoxin

C15H22O3 (250.1568862)


An apo carotenoid sesquiterpenoid that is xanthoxin in which the double bonds at positions 2 and 4 have E (trans) configuration. D020011 - Protective Agents > D000975 - Antioxidants > D002338 - Carotenoids

   

plakortide F free acid

plakortide F free acid

C20H36O4 (340.2613456)


A marine-derived polyketide endoperoxide that exhibits strong inhibitory activity against the opportunistic fungal pathogens Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus.

   

Avenasterol

24Z-ethylidene-cholest-7-en-3beta-ol

C29H48O (412.37049579999996)


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

   

methyl (5e,9e)-hexacosa-5,9-dienoate

methyl (5e,9e)-hexacosa-5,9-dienoate

C27H50O2 (406.38106)


   

(3r,8s)-n-[(1r)-1-{[(2s)-1-[(2s)-2-{[(1r)-1-{[(3r,6s,9r,10s,13r,18as)-13-benzyl-1,4,11-trihydroxy-6-isopropyl-9-methyl-3-(2-methylpropyl)-7,14-dioxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-2-hydroxyethyl]-8-(acetyloxy)-3-hydroxy-9-methyldecanimidic acid

(3r,8s)-n-[(1r)-1-{[(2s)-1-[(2s)-2-{[(1r)-1-{[(3r,6s,9r,10s,13r,18as)-13-benzyl-1,4,11-trihydroxy-6-isopropyl-9-methyl-3-(2-methylpropyl)-7,14-dioxo-3h,6h,9h,10h,13h,16h,17h,18h,18ah-pyrrolo[2,1-i]1-oxa-4,7,10,13-tetraazacyclohexadecan-10-yl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-4-methyl-1-oxopentan-2-yl]-c-hydroxycarbonimidoyl}-2-hydroxyethyl]-8-(acetyloxy)-3-hydroxy-9-methyldecanimidic acid

C59H93N9O15 (1167.6790788)


   

(3r,4e,6z,15z)-3-hydroxyoctadeca-4,6,15-trienoic acid

(3r,4e,6z,15z)-3-hydroxyoctadeca-4,6,15-trienoic acid

C18H30O3 (294.21948299999997)


   

3,5-dibromo-4-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,9'(16'),11'-hexaen-8'-one

3,5-dibromo-4-hydroxy-6',10',15'-triazaspiro[cyclohexane-1,3'-tetracyclo[7.6.1.0²,⁷.0¹²,¹⁶]hexadecane]-1'(15'),2,2'(7'),5,9'(16'),11'-hexaen-8'-one

C18H15Br2N3O2 (462.95309299999997)


   

(3r,4e,6z)-3-hydroxyhexadeca-4,6-dienoic acid

(3r,4e,6z)-3-hydroxyhexadeca-4,6-dienoic acid

C16H28O3 (268.2038338)


   

(3e,5e,7e,9e)-1-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-18-(4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-(hydroxymethyl)-7,12,16-trimethyloctadeca-3,5,7,9,11,13,15,17-octaen-2-one

(3e,5e,7e,9e)-1-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)-18-(4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl)-3-(hydroxymethyl)-7,12,16-trimethyloctadeca-3,5,7,9,11,13,15,17-octaen-2-one

C40H56O4 (600.4178376)


   

2-[2-(acetyloxy)ethenyl]-6,10,14-trimethylpentadec-1-en-1-yl acetate

2-[2-(acetyloxy)ethenyl]-6,10,14-trimethylpentadec-1-en-1-yl acetate

C24H42O4 (394.30829320000004)


   

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

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

C31H50O2 (454.38106)


   

(2r)-2-hydroxy-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl hexadecanoate

(2r)-2-hydroxy-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl hexadecanoate

C25H48O9 (492.3298158)


   

(4e)-3-hydroxyhexadeca-4,6-dienoic acid

(4e)-3-hydroxyhexadeca-4,6-dienoic acid

C16H28O3 (268.2038338)


   

(1e,3z)-4-(acetyloxy)-3-[(1s,4r,6s)-1-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]buta-1,3-dien-1-yl acetate

(1e,3z)-4-(acetyloxy)-3-[(1s,4r,6s)-1-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]buta-1,3-dien-1-yl acetate

C24H32O7 (432.2147922)


   

(4e)-3-hydroxyoctadeca-4,6-dienoic acid

(4e)-3-hydroxyoctadeca-4,6-dienoic acid

C18H32O3 (296.2351322)


   

n-[12-benzyl-5,8,11,14,17-pentahydroxy-6-(1-hydroxyethyl)-3-(hydroxymethyl)-19-methyl-9,15-bis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-2-[(1-hydroxy-2-methylpropylidene)amino]-3-phenylpropanimidic acid

n-[12-benzyl-5,8,11,14,17-pentahydroxy-6-(1-hydroxyethyl)-3-(hydroxymethyl)-19-methyl-9,15-bis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-2-[(1-hydroxy-2-methylpropylidene)amino]-3-phenylpropanimidic acid

C45H65N7O11 (879.474182)


   
   

(6r,6'r)-ε-carotene

(6r,6'r)-ε-carotene

C40H56 (536.4381776)


   

(1e,3z)-4-(acetyloxy)-3-[(1r,4s,6r)-1-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]buta-1,3-dien-1-yl acetate

(1e,3z)-4-(acetyloxy)-3-[(1r,4s,6r)-1-[(3e)-4,8-dimethylnona-3,7-dien-1-yl]-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]buta-1,3-dien-1-yl acetate

C24H32O7 (432.2147922)


   

(3r,6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylheptan-1-ol

(3r,6r)-6-[(1r,3as,3br,9as,9bs,11ar)-9a,11a-dimethyl-tetradecahydro-1h-cyclopenta[a]phenanthren-1-yl]-3-isopropylheptan-1-ol

C29H52O (416.4017942)


   

n-[(1r)-1-{[(3s,6r,9s,12r,15r,18r,19s)-12-benzyl-5,8,11,14,17-pentahydroxy-6-[(1r)-1-hydroxyethyl]-3-(hydroxymethyl)-19-methyl-9,15-bis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-2-methylbutanimidic acid

n-[(1r)-1-{[(3s,6r,9s,12r,15r,18r,19s)-12-benzyl-5,8,11,14,17-pentahydroxy-6-[(1r)-1-hydroxyethyl]-3-(hydroxymethyl)-19-methyl-9,15-bis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-phenylethyl]-2-methylbutanimidic acid

C46H67N7O11 (893.4898312)


   

n-[(1r)-1-{[(1s,2r)-1-{[(1s)-1-{[(2r)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12r,15s,18r,19r)-9-benzyl-15-[(2s)-butan-2-yl]-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-hydroxy-5-methylhexanimidic acid

n-[(1r)-1-{[(1s,2r)-1-{[(1s)-1-{[(2r)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12r,15s,18r,19r)-9-benzyl-15-[(2s)-butan-2-yl]-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-hydroxy-5-methylhexanimidic acid

C75H124N14O17 (1492.9268414)


   

2-[1,2-bis(acetyloxy)propyl]-14-(5-methyl-2-oxo-5h-furan-3-yl)tetradecanoic acid

2-[1,2-bis(acetyloxy)propyl]-14-(5-methyl-2-oxo-5h-furan-3-yl)tetradecanoic acid

C26H42O8 (482.2879532)


   

4-bromo-n-{[(2r,4s)-2-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl]methyl}-1h-pyrrole-2-carboxamide

4-bromo-n-{[(2r,4s)-2-{[(4-bromo-1h-pyrrol-2-yl)formamido]methyl}-3,4-bis(2-imino-1,3-dihydroimidazol-4-yl)cyclobutyl]methyl}-1h-pyrrole-2-carboxamide

C22H24Br2N10O2 (618.0450324)


   

1-(5-ethyl-6-methylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

1-(5-ethyl-6-methylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C31H50O2 (454.38106)


   

(1e,3e,7s,11r)-3-[(acetyloxy)methylidene]-7,11,15-trimethylhexadec-1-en-1-yl acetate

(1e,3e,7s,11r)-3-[(acetyloxy)methylidene]-7,11,15-trimethylhexadec-1-en-1-yl acetate

C24H42O4 (394.30829320000004)


   

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

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

C30H48O2 (440.36541079999995)


   

(4e)-3-hydroxyoctadeca-4,6,15-trienoic acid

(4e)-3-hydroxyoctadeca-4,6,15-trienoic acid

C18H30O3 (294.21948299999997)


   

tricos-15-enoic acid

tricos-15-enoic acid

C23H44O2 (352.3341124)


   

(2s)-1-(hexadecanoyloxy)-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate

(2s)-1-(hexadecanoyloxy)-3-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl (5z,8z,11z,14z)-icosa-5,8,11,14-tetraenoate

C45H78O10 (778.5594688)


   

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one

(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one

C29H46O2 (426.34976159999997)


   

[(1r,3ar,5ar,6r,7s,9as,11ar)-3a,6,9a,11a-tetramethyl-1-[(2r)-6-methyl-4-oxoheptan-2-yl]-6-[(sulfooxy)methyl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

[(1r,3ar,5ar,6r,7s,9as,11ar)-3a,6,9a,11a-tetramethyl-1-[(2r)-6-methyl-4-oxoheptan-2-yl]-6-[(sulfooxy)methyl]-1h,2h,3h,4h,5h,5ah,7h,8h,9h,10h,11h-cyclopenta[a]phenanthren-7-yl]oxidanesulfonic acid

C30H50O9S2 (618.289609)


   

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

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

C28H46O (398.3548466)


   

(2r)-2-hydroxy-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl (9z)-octadec-9-enoate

(2r)-2-hydroxy-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propyl (9z)-octadec-9-enoate

C27H50O9 (518.345465)


   

n-{1-[(1-{[1-({1-[2-({4-amino-1-[(1-{[9-benzyl-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-15-(sec-butyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl)-c-hydroxycarbonimidoyl]butyl}-c-hydroxycarbonimidoyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl)-c-hydroxycarbonimidoyl]-2-methylpropyl}-5-hydroxy-5-methylhexanimidic acid

n-{1-[(1-{[1-({1-[2-({4-amino-1-[(1-{[9-benzyl-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-15-(sec-butyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl)-c-hydroxycarbonimidoyl]butyl}-c-hydroxycarbonimidoyl)pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl)-c-hydroxycarbonimidoyl]-2-methylpropyl}-5-hydroxy-5-methylhexanimidic acid

C75H124N14O17 (1492.9268414)


   

(1r,3as,3bs,5r,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-diol

(1r,3as,3bs,5r,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,5h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-5,7-diol

C29H48O2 (428.36541079999995)


   

n-[(1r)-1-{[(1s,2r)-1-{[(1s)-1-{[(2r)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12r,15r,18r,19s)-9-benzyl-15-[(2s)-butan-2-yl]-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-hydroxy-5-methylhexanimidic acid

n-[(1r)-1-{[(1s,2r)-1-{[(1s)-1-{[(2r)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12r,15r,18r,19s)-9-benzyl-15-[(2s)-butan-2-yl]-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-hydroxy-5-methylhexanimidic acid

C75H124N14O17 (1492.9268414)


   

2-[(3r,6s,9r,12s,19r,23s,24as)-19-benzyl-1,4,7,10,17,23-hexahydroxy-12-[(4-hydroxyphenyl)methyl]-6-isopropyl-3-methyl-15-(6-methylheptyl)-13,20-dioxo-3h,6h,9h,12h,15h,16h,19h,22h,23h,24h,24ah-pyrrolo[2,1-o]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-9-yl]ethanimidic acid

2-[(3r,6s,9r,12s,19r,23s,24as)-19-benzyl-1,4,7,10,17,23-hexahydroxy-12-[(4-hydroxyphenyl)methyl]-6-isopropyl-3-methyl-15-(6-methylheptyl)-13,20-dioxo-3h,6h,9h,12h,15h,16h,19h,22h,23h,24h,24ah-pyrrolo[2,1-o]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-9-yl]ethanimidic acid

C46H65N7O11 (891.474182)


   

2-[(3r,6s,9r,12s,15s,19r,23r,24as)-19-benzyl-1,4,7,10,17,23-hexahydroxy-12-[(4-hydroxyphenyl)methyl]-6-isopropyl-3-methyl-15-(6-methylheptyl)-13,20-dioxo-3h,6h,9h,12h,15h,16h,19h,22h,23h,24h,24ah-pyrrolo[2,1-o]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-9-yl]ethanimidic acid

2-[(3r,6s,9r,12s,15s,19r,23r,24as)-19-benzyl-1,4,7,10,17,23-hexahydroxy-12-[(4-hydroxyphenyl)methyl]-6-isopropyl-3-methyl-15-(6-methylheptyl)-13,20-dioxo-3h,6h,9h,12h,15h,16h,19h,22h,23h,24h,24ah-pyrrolo[2,1-o]1-oxa-4,7,10,13,16,19-hexaazacyclodocosan-9-yl]ethanimidic acid

C46H65N7O11 (891.474182)


   

1-(5-ethyl-6-methylhept-6-en-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one

1-(5-ethyl-6-methylhept-6-en-2-yl)-7-hydroxy-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-4-one

C29H46O2 (426.34976159999997)


   

[(1s,3r,6s,7r,8r,11s,12s,15r,16r)-15-[(2r,4s)-4-hydroxy-6-methylheptan-2-yl]-7,12,16-trimethyl-7-[(sulfooxy)methyl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxidanesulfonic acid

[(1s,3r,6s,7r,8r,11s,12s,15r,16r)-15-[(2r,4s)-4-hydroxy-6-methylheptan-2-yl]-7,12,16-trimethyl-7-[(sulfooxy)methyl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxidanesulfonic acid

C30H52O9S2 (620.3052582)


   

n-{3-[(3s,6s,10r,15as)-1,8-dihydroxy-10-(1h-indol-3-ylmethyl)-6-(4-methylpentyl)-4,11-dioxo-3h,6h,7h,10h,13h,14h,15h,15ah-pyrrolo[2,1-f]1-oxa-4,7,10-triazacyclotridecan-3-yl]propyl}guanidine

n-{3-[(3s,6s,10r,15as)-1,8-dihydroxy-10-(1h-indol-3-ylmethyl)-6-(4-methylpentyl)-4,11-dioxo-3h,6h,7h,10h,13h,14h,15h,15ah-pyrrolo[2,1-f]1-oxa-4,7,10-triazacyclotridecan-3-yl]propyl}guanidine

C31H45N7O5 (595.3481999999999)


   

n-[(1r)-1-{[(1s,2r)-1-{[(1s)-1-{[(2r)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12r,15r,18r,19r)-9-benzyl-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-15-(sec-butyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-methylhexanimidic acid

n-[(1r)-1-{[(1s,2r)-1-{[(1s)-1-{[(2r)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12r,15r,18r,19r)-9-benzyl-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-15-(sec-butyl)-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-methylhexanimidic acid

C75H124N14O16 (1476.9319264)


   

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

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

C29H48O (412.37049579999996)


   

[(1s,3r,6s,7r,8r,11s,12s,15r,16r)-7,12,16-trimethyl-15-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-7-[(sulfooxy)methyl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxidanesulfonic acid

[(1s,3r,6s,7r,8r,11s,12s,15r,16r)-7,12,16-trimethyl-15-[(2r)-6-methyl-4-oxohept-5-en-2-yl]-7-[(sulfooxy)methyl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxidanesulfonic acid

C30H48O9S2 (616.2739598000001)


   

1-(5,6-dimethylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

1-(5,6-dimethylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl acetate

C30H48O2 (440.36541079999995)


   

(2r)-1-(hexadecanoyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl hexadecanoate

(2r)-1-(hexadecanoyloxy)-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl hexadecanoate

C41H78O10 (730.5594688)


   

(1e,3e,7s,11s)-3-[(acetyloxy)methylidene]-7,11,15-trimethylhexadec-1-en-1-yl acetate

(1e,3e,7s,11s)-3-[(acetyloxy)methylidene]-7,11,15-trimethylhexadec-1-en-1-yl acetate

C24H42O4 (394.30829320000004)


   

(15e)-tricos-15-enoic acid

(15e)-tricos-15-enoic acid

C23H44O2 (352.3341124)


   

methyl 2-[(3s,4s,6s)-4,6-diethyl-6-[(5e)-4-ethyloct-5-en-1-yl]-1,2-dioxan-3-yl]acetate

methyl 2-[(3s,4s,6s)-4,6-diethyl-6-[(5e)-4-ethyloct-5-en-1-yl]-1,2-dioxan-3-yl]acetate

C21H38O4 (354.2769948)


   

(2r)-n-[(3s,6s,9r,12r,15r,18s,19r)-12-benzyl-5,8,11,14,17-pentahydroxy-6-[(1r)-1-hydroxyethyl]-3-(hydroxymethyl)-19-methyl-9,15-bis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-2-[(1-hydroxy-2-methylpropylidene)amino]-3-phenylpropanimidic acid

(2r)-n-[(3s,6s,9r,12r,15r,18s,19r)-12-benzyl-5,8,11,14,17-pentahydroxy-6-[(1r)-1-hydroxyethyl]-3-(hydroxymethyl)-19-methyl-9,15-bis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-2-[(1-hydroxy-2-methylpropylidene)amino]-3-phenylpropanimidic acid

C45H65N7O11 (879.474182)


   

(1r,3as,3bs,4r,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol

(1r,3as,3bs,4r,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol

C29H48O2 (428.36541079999995)


   

2-{[1-(5-ethyl-6-methylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[1-(5-ethyl-6-methylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C35H58O6 (574.4233168000001)


   

(2r)-n-[(3s,6r,9r,12r,15r,18r,19s)-12-benzyl-5,8,11,14,17-pentahydroxy-6-[(1s)-1-hydroxyethyl]-3-(hydroxymethyl)-19-methyl-9,15-bis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-2-[(1-hydroxy-2-methylpropylidene)amino]-3-phenylpropanimidic acid

(2r)-n-[(3s,6r,9r,12r,15r,18r,19s)-12-benzyl-5,8,11,14,17-pentahydroxy-6-[(1s)-1-hydroxyethyl]-3-(hydroxymethyl)-19-methyl-9,15-bis(2-methylpropyl)-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-2-[(1-hydroxy-2-methylpropylidene)amino]-3-phenylpropanimidic acid

C45H65N7O11 (879.474182)


   

4-(acetyloxy)-3-[1-(4,8-dimethylnona-3,7-dien-1-yl)-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]buta-1,3-dien-1-yl acetate

4-(acetyloxy)-3-[1-(4,8-dimethylnona-3,7-dien-1-yl)-2-oxo-3,7-dioxabicyclo[4.1.0]heptan-4-yl]buta-1,3-dien-1-yl acetate

C24H32O7 (432.2147922)


   

(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl hexadecanoate

(2e,7r,11r)-3,7,11,15-tetramethylhexadec-2-en-1-yl hexadecanoate

C36H70O2 (534.537552)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.386145)


   

1-(5-ethyl-6-methylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol

1-(5-ethyl-6-methylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol

C29H48O2 (428.36541079999995)


   

1,1-dimethylpyrrolidin-1-ium-2-carboxylate

1,1-dimethylpyrrolidin-1-ium-2-carboxylate

C7H13NO2 (143.0946238)


   

1-(5-hydroxy-5-isopropylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

1-(5-hydroxy-5-isopropylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H48O2 (428.36541079999995)


   

(1r,3as,3bs,4s,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol

(1r,3as,3bs,4s,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthrene-4,7-diol

C29H48O2 (428.36541079999995)


   

(2r,3r,4s,5s,6r)-2-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C35H58O6 (574.4233168000001)


   

(7s)-1-(5-hydroxy-5-isopropylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

(7s)-1-(5-hydroxy-5-isopropylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H48O2 (428.36541079999995)


   

5,6-dibromodimethyltryptamine

5,6-dibromodimethyltryptamine

C12H14Br2N2 (343.9523644)


   

1-(5-ethyl-6-methylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

1-(5-ethyl-6-methylhept-6-en-2-yl)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-ol

C29H48O (412.37049579999996)


   

methyl hexacosa-5,9-dienoate

methyl hexacosa-5,9-dienoate

C27H50O2 (406.38106)


   

n-[(1r)-1-{[(1s,2r)-1-{[(1s)-1-{[(2r)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12r,15s,18s,19r)-9-benzyl-15-[(2s)-butan-2-yl]-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-methylhexanimidic acid

n-[(1r)-1-{[(1s,2r)-1-{[(1s)-1-{[(2r)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12r,15s,18s,19r)-9-benzyl-15-[(2s)-butan-2-yl]-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-methylhexanimidic acid

C75H124N14O16 (1476.9319264)


   

n-[(1s)-1-{[(1s,2r)-1-{[(1s)-1-{[(2s)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12s,15r,18s,19r)-9-benzyl-15-[(2s)-butan-2-yl]-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-methylhexanimidic acid

n-[(1s)-1-{[(1s,2r)-1-{[(1s)-1-{[(2s)-1-[(2r)-2-{[(1s)-4-amino-1-{[(1r,2s)-1-{[(3s,6z,9s,12s,15r,18s,19r)-9-benzyl-15-[(2s)-butan-2-yl]-6-ethylidene-5,8,11,14,17-pentahydroxy-3,12-diisopropyl-19-methyl-2-oxo-1-oxa-4,7,10,13,16-pentaazacyclononadeca-4,7,10,13,16-pentaen-18-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}butyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-3-methyl-1-oxobutan-2-yl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-hydroxypropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-5-methylhexanimidic acid

C75H124N14O16 (1476.9319264)


   

n-(4-chlorophenyl)-1-{n-[6-(n-{[n'-(4-chlorophenyl)carbamimidamido]methanimidoyl}amino)hexyl]carbamimidamido}methanimidamide

n-(4-chlorophenyl)-1-{n-[6-(n-{[n'-(4-chlorophenyl)carbamimidamido]methanimidoyl}amino)hexyl]carbamimidamido}methanimidamide

C22H30Cl2N10 (504.20318399999996)


   

1-(hexadecanoyloxy)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl icosa-5,8,11,14-tetraenoate

1-(hexadecanoyloxy)-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}propan-2-yl icosa-5,8,11,14-tetraenoate

C45H78O10 (778.5594688)


   

(3r,4e,6z)-3-hydroxyoctadeca-4,6-dienoic acid

(3r,4e,6z)-3-hydroxyoctadeca-4,6-dienoic acid

C18H32O3 (296.2351322)


   

[(1s,3r,6s,7r,8r,11s,12s,15r,16r)-7,12,16-trimethyl-15-[(2r)-6-methyl-4-oxoheptan-2-yl]-7-[(sulfooxy)methyl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxidanesulfonic acid

[(1s,3r,6s,7r,8r,11s,12s,15r,16r)-7,12,16-trimethyl-15-[(2r)-6-methyl-4-oxoheptan-2-yl]-7-[(sulfooxy)methyl]pentacyclo[9.7.0.0¹,³.0³,⁸.0¹²,¹⁶]octadecan-6-yl]oxidanesulfonic acid

C30H50O9S2 (618.289609)


   

(2r,3r,4s,5r,6r)-2-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5r,6r)-2-{[(1r,3as,3bs,7s,9ar,9bs,11ar)-1-[(2r,5r)-5-ethyl-6-methylhept-6-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C35H58O6 (574.4233168000001)


   

(3s,8r,10s)-5-bromo-9-thia-11,15,20-triazahexacyclo[12.6.1.1³,¹⁰.0²,¹².0³,⁸.0¹⁷,²¹]docosa-1(20),2(12),4,14(21),16-pentaene-6,13-dione

(3s,8r,10s)-5-bromo-9-thia-11,15,20-triazahexacyclo[12.6.1.1³,¹⁰.0²,¹².0³,⁸.0¹⁷,²¹]docosa-1(20),2(12),4,14(21),16-pentaene-6,13-dione

C18H14BrN3O2S (414.99900440000005)


   

n-[(1s)-1-{[(3s,10r,13s,16r,21as)-13-benzyl-1,4,11,14-tetrahydroxy-3-[(1r)-1-hydroxyethyl]-16-(2-methylpropyl)-7,17-dioxo-3h,6h,9h,10h,13h,16h,19h,20h,21h,21ah-pyrrolo[2,1-i]1-oxa-4,7,10,13,16-pentaazacyclononadecan-10-yl]-c-hydroxycarbonimidoyl}-2-(4-hydroxyphenyl)ethyl]-5-methylhexanimidic acid

n-[(1s)-1-{[(3s,10r,13s,16r,21as)-13-benzyl-1,4,11,14-tetrahydroxy-3-[(1r)-1-hydroxyethyl]-16-(2-methylpropyl)-7,17-dioxo-3h,6h,9h,10h,13h,16h,19h,20h,21h,21ah-pyrrolo[2,1-i]1-oxa-4,7,10,13,16-pentaazacyclononadecan-10-yl]-c-hydroxycarbonimidoyl}-2-(4-hydroxyphenyl)ethyl]-5-methylhexanimidic acid

C45H63N7O11 (877.4585328000001)