NCBI Taxonomy: 6843
Chelicerata (ncbi_taxid: 6843)
found 205 associated metabolites at subphylum taxonomy rank level.
Ancestor: Arthropoda
Child Taxonomies: Arachnida, Merostomata, Pycnogonida
Luteolin
Luteolin is a naturally occurring flavonoid. (PMID:17168665). The flavonoids are polyphenolic compounds found as integral components of the human diet. They are universally present as constituents of flowering plants, particularly of food plants. The flavonoids are phenyl substituted chromones (benzopyran derivatives) consisting of a 15-carbon basic skeleton (C6-C3-C6), composed of a chroman (C6-C3) nucleus (the benzo ring A and the heterocyclic ring C), also shared by the tocopherols, with a phenyl (the aromatic ring B) substitution usually at the 2-position. Different substitutions can typically occur in the rings, A and B. Several plants and spices containing flavonoid derivatives have found application as disease preventive and therapeutic agents in traditional medicine in Asia for thousands of years. The selection of a particular food plant, plant tissue or herb for its potential health benefits appears to mirror its flavonoid composition. The much lower risk of colon, prostate and breast cancers in Asians, who consume more vegetables, fruits and tea than populations in the Western hemisphere do, raises the question of whether flavonoid components mediate the protective effects of diets rich in these foodstuffs by acting as natural chemopreventive and anticancer agents. An impressive body of information exists on the antitumoral action of plant flavonoids. In vitro work has concentrated on the direct and indirect actions of flavonoids on tumor cells, and has found a variety of anticancer effects such as cell growth and kinase activity inhibition, apoptosis induction, suppression of the secretion of matrix metalloproteinases and of tumor invasive behavior. Furthermore, some studies have reported the impairment of in vivo angiogenesis by dietary flavonoids. Experimental animal studies indicate that certain dietary flavonoids possess antitumoral activity. The hydroxylation pattern of the B ring of the flavones and flavonols, such as luteolin seems to critically influence their activities, especially the inhibition of protein kinase activity and antiproliferation. The different mechanisms underlying the potential anticancer action of plant flavonoids await further elucidation. Certain dietary flavonols and flavones targeting cell surface signal transduction enzymes, such as protein tyrosine and focal adhesion kinases, and the processes of angiogenesis appear to be promising candidates as anticancer agents. Further in vivo studies of these bioactive constituents is deemed necessary in order to develop flavonoid-based anticancer strategies. In view of the increasing interest in the association between dietary flavonoids and cancer initiation and progression, this important field is likely to witness expanded effort and to attract and stimulate further vigorous investigations (PMID:16097445). Luteolin is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. It has a role as an EC 2.3.1.85 (fatty acid synthase) inhibitor, an antineoplastic agent, a vascular endothelial growth factor receptor antagonist, a plant metabolite, a nephroprotective agent, an angiogenesis inhibitor, a c-Jun N-terminal kinase inhibitor, an anti-inflammatory agent, an apoptosis inducer, a radical scavenger and an immunomodulator. It is a 3-hydroxyflavonoid and a tetrahydroxyflavone. It is a conjugate acid of a luteolin-7-olate. Luteolin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Luteolin is a naturally-occurring flavonoid, with potential anti-oxidant, anti-inflammatory, apoptosis-inducing and chemopreventive activities. Upon administration, luteolin scavenges free radicals, protects cells from reactive oxygen species (ROS)-induced damage and induces direct cell cycle arrest and apoptosis in tumor cells. This inhibits tumor cell proliferation and suppresses metastasis. 5,7,3,4-tetrahydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 4, 5 and 7. It is thought to play an important role in the human body as an antioxidant, a free radical scavenger, an anti-inflammatory agent and an immune system modulator as well as being active against several cancers. Flavone v. widespread in plant world; found especies in celery, peppermint, rosemary, thyme and Queen Annes Lace leaves (wild carrot). Potential nutriceutical. Luteolin is found in many foods, some of which are soy bean, ginger, abalone, and swiss chard. Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 361; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 48 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].
linolenate(18:3)
alpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. alpha-Linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. α-Linolenic acid can be obtained by humans only through their diets. Humans lack the desaturase enzymes required for processing stearic acid into A-linoleic acid or other unsaturated fatty acids. Dietary α-linolenic acid is metabolized to stearidonic acid, a precursor to a collection of polyunsaturated 20-, 22-, 24-, etc fatty acids (eicosatetraenoic acid, eicosapentaenoic acid, docosapentaenoic acid, tetracosapentaenoic acid, 6,9,12,15,18,21-tetracosahexaenoic acid, docosahexaenoic acid).[12] Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA.[13] Conversion of ALA to DHA is higher in women than in men.[14] α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.[2] In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds). Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. alpha-Linolenic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Linolenic Acid is a natural product found in Prunus mume, Dipteryx lacunifera, and other organisms with data available. Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group. It is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. A fatty acid that is found in plants and involved in the formation of prostaglandins. Seed oils are the richest sources of α-linolenic acid, notably those of hempseed, chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans. α-Linolenic acid is also obtained from the thylakoid membranes in the leaves of Pisum sativum (pea leaves).[3] Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of ALA, evident as sharp resonances in high-resolution carbon-13 NMR spectra.[4] Some studies state that ALA remains stable during processing and cooking.[5] However, other studies state that ALA might not be suitable for baking as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some ALA may also oxidize at baking temperatures. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].
Hordenine
Hordenine is a potent phenylethylamine alkaloid with antibacterial and antibiotic properties produced in nature by several varieties of plants in the family Cactacea. The major source of hordenine in humans is beer brewed from barley. Hordenine in urine interferes with tests for morphine, heroin and other opioid drugs. Hordenine is a biomarker for the consumption of beer Hordenine is a phenethylamine alkaloid. It has a role as a human metabolite and a mouse metabolite. Hordenine is a natural product found in Cereus peruvianus, Mus musculus, and other organisms with data available. See also: Selenicereus grandiflorus stem (part of). Alkaloid from Hordeum vulgare (barley) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2289 Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1]. Hordenine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=539-15-1 (retrieved 2024-10-24) (CAS RN: 539-15-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).
Myristic acid
Tetradecanoic acid is an oily white crystalline solid. (NTP, 1992) Tetradecanoic acid is a straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetradecanoate. Myristic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Myristic acid is a natural product found in Gladiolus italicus, Staphisagria macrosperma, and other organisms with data available. Myristic Acid is a saturated long-chain fatty acid with a 14-carbon backbone. Myristic acid is found naturally in palm oil, coconut oil and butter fat. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed). Myristic acid is also commonly added to a penultimate nitrogen terminus glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. this is achieved by the myristic acid having a high enough hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell.(wikipedia). myristic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. It is used to synthesize flavor and as an ingredient in soaps and cosmetics. (From Dorland, 28th ed) See also: Cod Liver Oil (part of); Saw Palmetto (part of). Myristic acid, also known as tetradecanoic acid or C14:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Myristic acid (its ester is called myristate) is a saturated fatty acid that has 14 carbons; as such, it is a very hydrophobic molecule that is practically insoluble in water. It exists as an oily white crystalline solid. Myristic acid is found in all living organisms ranging from bacteria to plants to animals, and is found in most animal and vegetable fats, particularly butterfat, as well as coconut, palm, and nutmeg oils. Industrially, myristic acid is used to synthesize a variety of flavour compounds and as an ingredient in soaps and cosmetics (Dorland, 28th ed). Within eukaryotic cells, myristic acid is also commonly conjugated to a penultimate N-terminal glycine residue in receptor-associated kinases to confer membrane localization of these enzymes (a post-translational modification called myristoylation via the enzyme N-myristoyltransferase). Myristic acid has a high enough hydrophobicity to allow the myristoylated protein to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of eukaryotic cells. Also, this fatty acid is known because it accumulates as fat in the body; however, its consumption also impacts positively on cardiovascular health (see, for example, PMID: 15936650). Myristic acid is named after the scientific name for nutmeg, Myristica fragrans, from which it was first isolated in 1841 by Lyon Playfair. Myristic acid, also known as 14 or N-tetradecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, myristic acid is considered to be a fatty acid lipid molecule. Myristic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Myristic acid can be found in a number of food items such as strawberry, barley, nutmeg, and soy bean, which makes myristic acid a potential biomarker for the consumption of these food products. Myristic acid can be found primarily in most biofluids, including cerebrospinal fluid (CSF), blood, saliva, and feces, as well as throughout most human tissues. Myristic acid exists in all living species, ranging from bacteria to humans. In humans, myristic acid is involved in the fatty acid biosynthesis. Moreover, myristic acid is found to be associated with schizophrenia. Myristic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Myristic acid (IUPAC systematic name: 1-tetradecanoic acid) is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. Its salts and esters are commonly referred to as myristates. It is named after the binomial name for nutmeg (Myristica fragrans), from which it was first isolated in 1841 by Lyon Playfair . A straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. Nutmeg butter has 75\\\% trimyristin, the triglyceride of myristic acid and a source from which it can be synthesised.[13] Besides nutmeg, myristic acid is found in palm kernel oil, coconut oil, butterfat, 8–14\\\% of bovine milk, and 8.6\\\% of breast milk as well as being a minor component of many other animal fats.[9] It is found in spermaceti, the crystallized fraction of oil from the sperm whale. It is also found in the rhizomes of the Iris, including Orris root.[14][15] Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.
Geraniol
Geraniol, also known as beta-Geraniol, (E)-nerol (the isomer of nerol) or geranyl alcohol, is a monoterpenoid alcohol. It belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. In plants, the biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in the plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. beta-Geraniol is an isoprenoid lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. beta-Geraniol has a sweet, citrus, and floral taste. beta-Geraniol is found in highest concentrations in common grapes, black walnuts, and common thymes and in lower concentrations in cardamoms, common oregano, and gingers. beta-Geraniol has also been detected in lemon verbena, oval-leaf huckleberries, common pea, sweet cherries, and nopals. It is found as an alcohol and as its ester in many essential oils including geranium oil. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type) and occurs in small quantities in geranium, lemon, and many other essential oils. Because it has a rose-like odor, it is commonly used in perfumes. It is used to create flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry. An alternate application has been found in the use of insect repellents or deterrants. Though it may repel mosquitoes, flies, lice, cockroaches, ants, and ticks, it is also produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the entrances to their hives (http//doi:10.1051/apido:19900403). Extensive testing by Dr. Jerry Butler at the University of Florida has shown geraniol to be one of natures most effective insect repellents (PMID:20836800). Nerol is the (2Z)-stereoisomer of 3,7-dimethylocta-2,6-dien-1-ol. It has been isolated from the essential oils from plants like lemon grass. It has a role as a volatile oil component, a plant metabolite and a fragrance. Nerol is a natural product found in Eupatorium cannabinum, Vitis rotundifolia, and other organisms with data available. Nerol is a metabolite found in or produced by Saccharomyces cerevisiae. Constituent of many essential oils including neroli and bergamot oils. In essential oils it is a minor component always accompanied by geraniol. Flavouring agent The (2Z)-stereoisomer of 3,7-dimethylocta-2,6-dien-1-ol. It has been isolated from the essential oils from plants like lemon grass. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2].
Norepinephrine
Norepinephrine is the precursor of epinephrine that is secreted by the adrenal medulla and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers and of the diffuse projection system in the brain arising from the locus ceruleus. It is also found in plants and is used pharmacologically as a sympathomimetic. Norepinephrine is elevated in the urine of people who consume bananas. Norepinephrine is also a microbial metabolite; urinary noradrenaline is produced by Escherichia, Bacillus, and Saccharomyces (PMID: 24621061). Norepinephrine is found in alcoholic beverages, banana peels and pulp (Musa paradisiaca), red plum fruit (Prunus domestica), orange pulp (Citrus sinensis), potato tubers (Solanum tuberosum), and whole purslane (Portulaca oleracea). P. oleracea is the richest of these sources. Norepinephrine has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID: 22626821). Present in banana peel and pulp (Musa paradisiaca), red plum fruit (Prunus domestica), orange pulp (Citrus sinensis), potato tubers (Solanum tuberosum) and whole purslane (Portulaca oleracea). P. oleracea is the richest of these sources. xi-Norepinephrine is found in many foods, some of which are potato, green vegetables, alcoholic beverages, and fruits.
Ellagic acid
Ellagic acid appears as cream-colored needles (from pyridine) or yellow powder. Odorless. (NTP, 1992) Ellagic acid is an organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. It has a role as an antioxidant, a food additive, a plant metabolite, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor, an EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor, an EC 2.4.1.1 (glycogen phosphorylase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor, an EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor, an EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor, a skin lightening agent, a fungal metabolite, an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor and a geroprotector. It is an organic heterotetracyclic compound, a cyclic ketone, a lactone, a member of catechols and a polyphenol. It is functionally related to a gallic acid. Ellagic acid is present in several fruits such as cranberries, strawberries, raspberries, and pomegranates. In pomegranates, there are several therapeutic compounds but ellagic acid is the most active and abundant. Ellagic acid is also present in vegetables. Ellagic acid is an investigational drug studied for treatment of Follicular Lymphoma (phase 2 trial), protection from brain injury of intrauterine growth restricted babies (phase 1 and 2 trial), improvement of cardiovascular function in adolescents who are obese (phase 2 trial), and topical treatment of solar lentigines. Ellagic acids therapeutic action mostly involves antioxidant and anti-proliferative effects. Ellagic acid is a natural product found in Fragaria chiloensis, Metrosideros perforata, and other organisms with data available. Ellagic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A fused four ring compound occurring free or combined in galls. Isolated from the kino of Eucalyptus maculata Hook and E. Hemipholia F. Muell. Activates Factor XII of the blood clotting system which also causes kinin release; used in research and as a dye. Ellagic acid is an organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. It has a role as an antioxidant, a food additive, a plant metabolite, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor, an EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor, an EC 2.4.1.1 (glycogen phosphorylase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor, an EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor, an EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor, a skin lightening agent, a fungal metabolite and an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor. It is an organic heterotetracyclic compound, a cyclic ketone, a lactone, a member of catechols and a polyphenol. It derives from a gallic acid. Ellagic acid, also known as ellagate, belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. The antiproliferative and antioxidant properties of ellagic acid have spurred preliminary research into the potential health benefits of ellagic acid consumption. Ellagic acids therapeutic action mostly involves antioxidant and anti-proliferative/anti-cancer effects. Ellagic acid is found, on average, in the highest concentration within a few different foods, such as chestnuts, common walnuts, and japanese walnuts and in a lower concentration in whiskies, arctic blackberries, and cloudberries. Ellagic acid has also been detected, but not quantified in several different foods, such as lowbush blueberries, bilberries, guava, strawberry guava, and bog bilberries. An organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. Widely distributed in higher plants especies dicotyledons. Intestinal astringent, dietary role disputed. Nutriceutical with anticancer and antioxidation props. Ellagic acid is a natural antioxidant, and acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM. Ellagic acid is a natural antioxidant, and acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM.
Tyramine
Tyramine is a monoamine compound derived from the amino acid tyrosine. Tyramine is metabolized by the enzyme monoamine oxidase. In foods, it is often produced by the decarboxylation of tyrosine during fermentation or decay. Foods containing considerable amounts of tyramine include fish, chocolate, alcoholic beverages, cheese, soy sauce, sauerkraut, and processed meat. A large dietary intake of tyramine can cause an increase in systolic blood pressure of 30 mmHg or more. Tyramine acts as a neurotransmitter via a G protein-coupled receptor with high affinity for tyramine called TA1. The TA1 receptor is found in the brain as well as peripheral tissues including the kidney. An indirect sympathomimetic, Tyramine can also serve as a substrate for adrenergic uptake systems and monoamine oxidase so it prolongs the actions of adrenergic transmitters. It also provokes transmitter release from adrenergic terminals. Tyramine is a biomarker for the consumption of cheese [Spectral] Tyramine (exact mass = 137.08406) and L-Methionine (exact mass = 149.05105) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Tyramine (exact mass = 137.08406) and Glutathione (exact mass = 307.08381) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics Acquisition and generation of the data is financially supported in part by CREST/JST. D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents IPB_RECORD: 267; CONFIDENCE confident structure CONFIDENCE standard compound; INTERNAL_ID 5105 D049990 - Membrane Transport Modulators KEIO_ID T008 Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1]. Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1].
Gluconolactone
Gluconolactone, also known as glucono-delta-lactone or GDL (gluconate), belongs to the class of organic compounds known as gluconolactones. These are polyhydroxy acids (PHAs) containing a gluconolactone molecule, which is characterized by a tetrahydropyran substituted by three hydroxyl groups, one ketone group, and one hydroxymethyl group. Gluconolactone is a lactone of D-gluconic acid. Gluconolactone can be produced by enzymatic oxidation of D-glucose via the enzyme glucose oxidase. It is a fundamental metabolite found in all organisms ranging from bacteria to plants to animals. Gluconolactone has metal chelating, moisturizing and antioxidant activities. Its ability in free radicals scavenging accounts for its antioxidant properties. Gluconolactone, is also used as a food additive with the E-number E575. In foods it is used as a sequestrant, an acidifier or a curing, pickling, or leavening agent. Gluconolactone is also used as a coagulant in tofu processing. Gluconolactone is widely used as a skin exfoliant in cosmetic products, where it is noted for its mild exfoliating and hydrating properties. Pure gluconolactone is a white odorless crystalline powder. It is pH-neutral, but hydrolyses in water to gluconic acid which is acidic, adding a tangy taste to foods. Gluconic acid has roughly a third of the sourness of citric acid. One gram of gluconolactone yields roughly the same amount of metabolic energy as one gram of sugar. Food additive; uses include acidifier, pH control agent, sequestrant C26170 - Protective Agent > C275 - Antioxidant D-(+)-Glucono-1,5-lactone is a polyhydroxy (PHA) that is capable of metal chelating, moisturizing and antioxidant activity.
Betanin
Isobetanin is found in red beetroot. Minor congener of Betanin, e.g. from beetroot and Amaranthus specie
Plumbagin
Plumbagin, also known as 5-hydroxy-2-methyl-1,4-naphthoquinone or 2-methyljuglone, is a member of the class of compounds known as naphthoquinones. Naphthoquinones are compounds containing a naphthohydroquinone moiety, which consists of a benzene ring linearly fused to a bezene-1,4-dione (quinone). Plumbagin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Plumbagin can be found in black walnut, common walnut, japanese persimmon, and persimmon, which makes plumbagin a potential biomarker for the consumption of these food products. Plumbagin is named after the plant genus Plumbago, from which it was originally isolated. It is also commonly found in the carnivorous plant genera Drosera and Nepenthes. It is also a component of the black walnut drupe . D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor D020011 - Protective Agents > D002316 - Cardiotonic Agents D006401 - Hematologic Agents > D000925 - Anticoagulants D000970 - Antineoplastic Agents D002317 - Cardiovascular Agents D007155 - Immunologic Factors Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica, exhibits anticancer and antiproliferative activities[1]. Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica, exhibits anticancer and antiproliferative activities[1].
Tridecane
Tridecane appears as an oily straw yellow clear liquid with a hydrocarbon odor. Flash point 190-196 °F. Specific gravity 0.76. Boiling point 456 °F. Repeated or prolonged skin contact may irritate or redden skin, progressing to dermatitis. Exposure to high concentrations of vapor may result in headache and stupor. Tridecane is a straight chain alkane containing 13 carbon atoms. It forms a component of the essential oils isolated from plants such as Abelmoschus esculentus. It has a role as a plant metabolite and a volatile oil component. Tridecane is a natural product found in Dryopteris assimilis, Thyanta perditor, and other organisms with data available. Tridecane is an alkane hydrocarbon with the chemical formula CH3(CH2)11CH3. Tridecane is found in allspice and it is also isolated from lime oil. It is a light, combustible colourless liquid that is used in the manufacture of paraffin products, the paper processing industry, in jet fuel research and in the rubber industry; furthermore, tridecane is used as a solvent and distillation chaser. n-tridecane is also one of the major chemicals secreted by some insects as a defense against predators. Tridecane has 802 constitutional isomers A straight chain alkane containing 13 carbon atoms. It forms a component of the essential oils isolated from plants such as Abelmoschus esculentus. Isolated from lime oil Tridecane is a short chain aliphatic hydrocarbon containing 13 carbon atoms. Tridecane is an volatile oil component isolated from essential oil of Piper aduncum L. Tridecane is a stress compound released by the brown marmorated stink bugs stress compound[1][2]. Tridecane is a short chain aliphatic hydrocarbon containing 13 carbon atoms. Tridecane is an volatile oil component isolated from essential oil of Piper aduncum L. Tridecane is a stress compound released by the brown marmorated stink bugs stress compound[1][2].
N-Methyltyramine
N-methyltyramine (NMT) is a phenolic amine. NMT is a potent stimulant of gastrin release present in alcoholic beverages produced by alcoholic fermentation, but not by distillation (i.e.: beer.). NMT is well absorbed in the small intestine, especially in the duodenum and jejunum. NMT is metabolized in the liver (the site of first-pass metabolism), but not in the small-intestinal mucosa. NMT is occasionally present in the stools of children and infants. Satisfactory results have been obtained in treating infective shock with injection of natural Fructus Aurantii immaturus (nat-FAI); the anti-shock effective compositions in FAI have been proved to be synephrine and NMT. (PMID: 10772638, 2570680). Present in germinating barley roots but not dormant grainsand is also present in dormant sawa millet seed hulls, but not hulled seeds. Alkaloid from prosso millet (Panicum miliaceum)
Betanidin
Minor congener of Betanidin. Isobetanidin is found in root vegetables. Isobetanidin is found in root vegetables. Minor congener of Betanidi
Caldopentamine
A polyazaalkane that is the 1,5,9,13,17-pentaaza derivative of heptodecane.
Betanin
(R)-Pterosin B
(S)-Pterosin B is found in green vegetables. (S)-Pterosin B is found as glycosides in the rhizomes of Pteridium aquilinum (bracken fern Pterosin B, a indanone found in bracken fern (Pteridium aquilinum), is an inhibitor of salt-inducible kinase 3 (Sik3) signaling. Pterosin B prevents chondrocyte hypertrophy and osteoarthritis in mice by inhibiting Sik3[1][2]. Pterosin B, a indanone found in bracken fern (Pteridium aquilinum), is an inhibitor of salt-inducible kinase 3 (Sik3) signaling. Pterosin B prevents chondrocyte hypertrophy and osteoarthritis in mice by inhibiting Sik3[1][2].
(10S,11S)-Pterosin C
(10S,11S)-Pterosin C is found in green vegetables. (10S,11S)-Pterosin C is a constituent of Pteridium aquilinum (bracken fern)
Glycopyrrolate
C19H28NO3+ (318.20690780000007)
Glycopyrrolate is only found in individuals that have used or taken this drug. It is a synthetic anticholinergic agent with a quaternary ammonium structure. A muscarinic competitive antagonist used as an antispasmodic, in some disorders of the gastrointestinal tract, and to reduce salivation with some anesthetics. [PubChem]Glycopyrrolate binds competitively to the muscarinic acetylcholine receptor. Like other anticholinergic (antimuscarinic) agents, it inhibits the action of acetylcholine on structures innervated by postganglionic cholinergic nerves and on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These peripheral cholinergic receptors are present in the autonomic effector cells of smooth muscle, cardiac muscle, the sinoatrial node, the atrioventricular node, exocrine glands and, to a limited degree, in the autonomic ganglia. Thus, it diminishes the volume and free acidity of gastric secretions and controls excessive pharyngeal, tracheal, and bronchial secretions. D - Dermatologicals > D11 - Other dermatological preparations > D11A - Other dermatological preparations > D11AA - Antihidrotics D018377 - Neurotransmitter Agents > D018678 - Cholinergic Agents > D018680 - Cholinergic Antagonists D002491 - Central Nervous System Agents
Isopiperitenone
Isopiperitenone, also known as 3-methyl-6-(1-methylethenyl)-2-cyclohexen-1-one or 6-isopropenyl-3-methyl-2-cyclohexen-1-one, is a member of the class of compounds known as menthane monoterpenoids. Menthane monoterpenoids are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Isopiperitenone is slightly soluble (in water) and an extremely weak acidic compound (based on its pKa). Isopiperitenone can be found in dill and spearmint, which makes isopiperitenone a potential biomarker for the consumption of these food products.
3-Methyl-2(3-methylbut-2-en-1-yl)furan
3-methyl-2(3-methylbut-2-en-1-yl)furan is a member of the class of compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. 3-methyl-2(3-methylbut-2-en-1-yl)furan is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). 3-methyl-2(3-methylbut-2-en-1-yl)furan is a caramel, green, and minty tasting compound found in ginger, which makes 3-methyl-2(3-methylbut-2-en-1-yl)furan a potential biomarker for the consumption of this food product.
C14:0
Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.
Perillene
Perillene is a monoterpenoid that is furan in which the hydrogen at position 3 is replaced by a 4-methylpent-3-en-1-yl group. A defensive allomone of thrips that has a flowery, citrus-like flavour. It has a role as a semiochemical, a metabolite and a fragrance. It is a member of furans and a monoterpenoid. Perillene is a natural product found in Curcuma amada, Origanum sipyleum, and other organisms with data available. A monoterpenoid that is furan in which the hydrogen at position 3 is replaced by a 4-methylpent-3-en-1-yl group. A defensive allomone of thrips that has a flowery, citrus-like flavour. Perillene, also known as 3-(4-methyl-3-pentenyl)furan, is a member of the class of compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. Perillene is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Perillene is a woody tasting compound found in common oregano and ginger, which makes perillene a potential biomarker for the consumption of these food products. Perillene is a natural monoterpene that consists of a furan ring with a six-carbon homoprenyl side chain. Perillene is a component of the essential oil obtained by extraction of the leaves of Perilla frutescens. Perillene has also been obtained by steam distillation of the leaves of Perilla frutescens. Perillene has been found to elicit distinct electrophysiological responses in the antennae of the apple blossom weevil. It has been suggested that perillene is one several terpene hydrocarbons in the emanation bouquet of apple tree buds which may be used by adult weevils as chemical cues to discrimination during host-searching behavior .
Plumbagin
Plumbagin is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively. It has a role as a metabolite, an immunological adjuvant, an anticoagulant and an antineoplastic agent. It is a member of phenols and a hydroxy-1,4-naphthoquinone. Plumbagin is a compound investigated for its anticancer activity. It has been found that it inactivates the Akt/NF-kB, MMP-9 and VEGF pathways. Plumbagin is a natural product found in Drosera slackii, Diospyros hebecarpa, and other organisms with data available. Synthetic Plumbagin PCUR-101 is a synthetic form of the plant-derived medicinal agent, plumbagin, with potential antineoplastic activity. Plumbagin may act by inhibiting the expression of protein kinase C epsilon (PKCe), signal transducers and activators of transcription 3 phosphorylation (Stat3), protein kinase B (AKT), and certain epithelial-to-mesenchymal transition (EMT) markers, including vimentin and slug. This results in possible inhibition of proliferation in susceptible tumor cells. PKCe, Stat3, AKT, and the EMT markers vimentin and slug have been linked to the induction and progression of prostate cancer. A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone in which the hydrogens at positions 2 and 5 are substituted by methyl and hydroxy groups, respectively. D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D012102 - Reproductive Control Agents > D003270 - Contraceptive Agents C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor D020011 - Protective Agents > D002316 - Cardiotonic Agents D006401 - Hematologic Agents > D000925 - Anticoagulants D000970 - Antineoplastic Agents D002317 - Cardiovascular Agents D007155 - Immunologic Factors relative retention time with respect to 9-anthracene Carboxylic Acid is 0.955 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.957 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.960 Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica, exhibits anticancer and antiproliferative activities[1]. Plumbagin (2-Methyljuglone) is a naphthoquinone isolated from Plumbago zeylanica, exhibits anticancer and antiproliferative activities[1].
12-epi-Scalarin
The 12-epimer of scalarin, a metabolite of marine sponges of the genus Spongia.
Betanidin
D004396 - Coloring Agents > D050859 - Betacyanins D004396 - Coloring Agents > D050858 - Betalains
Gluconolactone
C26170 - Protective Agent > C275 - Antioxidant D-(+)-Glucono-1,5-lactone is a polyhydroxy (PHA) that is capable of metal chelating, moisturizing and antioxidant activity.
Luteolin
Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.976 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.975 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.968 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.971 Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3]. Luteolin (Luteoline), a flavanoid compound, is a potent Nrf2 inhibitor. Luteolin has anti-inflammatory, anti-cancer properties, including the induction of apoptosis and cell cycle arrest, and the inhibition of metastasis and angiogenesis, in several cancer cell lines, including human non-small lung cancer cells[1][2][3].
12-epi-19-O-methylscalarin
A scalarane sesterterpenoid that is 12-epi-scalarin in which the hydorxy group at position 19 is replaced by a methoxy group. It has been isolated from the sponge, Hyattella species.
Tyramine
D018377 - Neurotransmitter Agents > D014179 - Neurotransmitter Uptake Inhibitors > D018759 - Adrenergic Uptake Inhibitors D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics A primary amino compound obtained by formal decarboxylation of the amino acid tyrosine. D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents D049990 - Membrane Transport Modulators Annotation level-2 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2741; CONFIDENCE confident structure Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1]. Tyramine is an amino acid that helps regulate blood pressure. Tyramine occurs naturally in the body, and it's found in certain foods[1].
Ellagic Acid
Origin: Plant, Ellagic acids, Benzopyranoids, Pyrans Ellagic acid is a natural antioxidant, and acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM. Ellagic acid is a natural antioxidant, and acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM.
Myristic Acid
Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils. Myristic acid is a saturated 14-carbon fatty acid occurring in most animal and vegetable fats, particularly butterfat and coconut, palm, and nutmeg oils.
Norepinephrine
C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist C78274 - Agent Affecting Cardiovascular System > C126567 - Vasopressor C - Cardiovascular system > C01 - Cardiac therapy > C01C - Cardiac stimulants excl. cardiac glycosides > C01CA - Adrenergic and dopaminergic agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents > D013566 - Sympathomimetics D018377 - Neurotransmitter Agents > D018663 - Adrenergic Agents > D000322 - Adrenergic Agonists D002317 - Cardiovascular Agents > D014662 - Vasoconstrictor Agents
Hordenine
Annotation level-1 Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1]. Hordenine, an alkaloid found in plants, inhibits melanogenesis by suppression of cyclic adenosine monophosphate (cAMP) production[1].
α-Linolenic acid
α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].
nerol
Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2]. Nerol is a constituent of neroli oil. Nerol Nerol triggers mitochondrial dysfunction and induces apoptosis via elevation of Ca2+ and ROS. Antifungal activity[1][2].
Pterosin B
CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 33 INTERNAL_ID 33; CONFIDENCE Reference Standard (Level 1) Pterosin B, a indanone found in bracken fern (Pteridium aquilinum), is an inhibitor of salt-inducible kinase 3 (Sik3) signaling. Pterosin B prevents chondrocyte hypertrophy and osteoarthritis in mice by inhibiting Sik3[1][2]. Pterosin B, a indanone found in bracken fern (Pteridium aquilinum), is an inhibitor of salt-inducible kinase 3 (Sik3) signaling. Pterosin B prevents chondrocyte hypertrophy and osteoarthritis in mice by inhibiting Sik3[1][2].
4-Methylheptan-3-one
A dialkyl ketone that is 4-methylheptane substituted by an oxo group at position 3.
Neral
An enal that is 3,7-dimethyloctanal with unsaturation at positions C-2 and C-6. It has been isolated form the essential oils of plant species like lemon.
12-Epi-Deoxoscalarin
A scalarane sesterterpenoid that is the deoxo derivative of 12-epi-scalarin. It has been isolated from the sponge,Hyattella species.
3-Methyl-3-(4-methylpent-3-en-1-yl)oxirane-2-carbaldehyde
3-hydroxy-6-(2-hydroxyethyl)-2,5,7-trimethyl-2,3-dihydro-1H-inden-1-one
(3as,4r,10as)-6-amino-10,10-dihydroxy-4-[(c-hydroxycarbonimidoyloxy)methyl]-2-imino-1h,3h,3ah,4h,8h,9h-pyrrolo[1,2-c]purin-5-ium-5-olate
(6s)-6-[(1s,3ar,3bs,9ar,9bs,11as)-9a,11a-dimethyl-1h,2h,3h,3ah,3bh,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-2-methylheptan-2-ol
n-(5-{[3-({4-[(3-aminopropyl)amino]butyl}amino)-1-hydroxypropylidene]amino}pentyl)-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
(4as,7r,7ar)-7-methyl-1h,2h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyridine-4-carbaldehyde
9a,11a-dimethyl-1-(6-methylheptan-2-yl)-1h,2h,3h,3ah,3bh,9h,9bh,10h,11h-cyclopenta[a]phenanthrene
(2's,4ar,5'r,6'r,7r)-9'-hydroxy-5',7-dimethyl-4a,5,6,7-tetrahydro-11'-azaspiro[cyclopenta[c]pyridine-4,8'-tricyclo[5.2.2.0²,⁶]undecan]-10'-ene-1'-carbaldehyde
(3r,3ar,11br)-3a,6-dimethyl-3-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,4h,5h,7h,8h,11bh-cyclopenta[a]anthracene
(2s)-n-(5-{[3-({4-[(3-{[4-({3-[(4-aminobutyl)amino]-1-hydroxypropylidene}amino)butyl]amino}-1-hydroxypropylidene)amino]butyl}amino)-1-hydroxypropylidene]amino}pentyl)-2-{[1-hydroxy-2-(4-hydroxy-1h-indol-3-yl)ethylidene]amino}butanediimidic acid
n-{3-[(1r)-6-hydroxy-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-yl]propyl}guanidine
(2s)-2-carboxy-1-{2-[(2s)-2-carboxy-6-carboxylato-2,3-dihydro-1h-pyridin-4-ylidene]ethylidene}-6-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)oxan-2-yl]oxy}-2,3-dihydro-1h-1λ⁵-indol-1-ylium
2-(5-propyloxolan-2-ylidene)cyclopentane-1,3-dione
n-(3-{[3-({3-[(4-aminobutyl)amino]propyl}amino)propyl](hydroxy)amino}propyl)-4-hydroxybenzamide
C20H37N5O3 (395.28962520000005)
[(3as,4r,10as)-10,10-dihydroxy-2,6-diimino-hexahydro-1h-pyrrolo[1,2-c]purin-4-yl]methoxycarboximidic acid
(2s,3s)-6-[(1r)-1,2-dihydroxyethyl]-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one
2-({6-[9a,11a-dimethyl-7-(sulfooxy)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-hydroxy-2-methylheptylidene}amino)-3-methylpentanoic acid
n-[3-(17-amino-1-hydroxy-1,5,9,14-tetraazaheptadecan-1-yl)propyl]-4-hydroxybenzamide
n-(4-{[3-({3-[(3-aminopropyl)amino]propyl}amino)propyl]amino}butyl)-4-hydroxybenzamide
(2s)-n-[5-({3-[(4-aminobutyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[1-hydroxy-2-(1h-indol-3-yl)ethylidene]amino}butanediimidic acid
C26H41N7O4 (515.3219866000001)
[(1r,5as,5br,7as,11ar,11bs,13r,13as,13bs)-13-(acetyloxy)-1-hydroxy-5b,8,8,13a-tetramethyl-1h,3h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-11a-yl]methyl acetate
(2s)-n-(5-{[(2s)-2,5-diamino-1-hydroxypentylidene]amino}pentyl)-2-{[1-hydroxy-2-(1h-indol-3-yl)ethylidene]amino}butanediimidic acid
C24H37N7O4 (487.29068820000003)
n-(4-{[3-({3-[(3-aminopropyl)amino]propyl}amino)propyl]amino}butyl)-2,5-dihydroxybenzenecarboximidic acid
C20H37N5O3 (395.28962520000005)
(2s,3s)-6-[(1r)-1,2-dihydroxyethyl]-2,5,7-trimethyl-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroinden-1-one
(2s)-n-[5-({3-[(4-{[(2r)-2-[(2-{[(2s)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxyethylidene)amino]-1-hydroxypropylidene]amino}butyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
(2s)-2-amino-5-(c-hydroxycarbonimidoylamino)pentanimidic acid
n-(4-{[3-({3-[(3-aminopropyl)amino]propyl}amino)propyl](hydroxy)amino}butyl)-2-(4-hydroxy-1h-indol-2-yl)ethanimidic acid
C23H40N6O3 (448.31617300000005)
n-(3-{6-hydroxy-1h,2h,3h,4h,9h-pyrido[3,4-b]indol-1-yl}propyl)guanidine
2-amino-5-(c-hydroxycarbonimidoylamino)pentanimidic acid
(2s)-4-{2-[(2s)-2-carboxy-6-hydroxy-5-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroindol-1-yl]ethenyl}-2,3-dihydropyridine-2,6-dicarboxylic acid
2,3-dihydroxy-6-(2-hydroxyethyl)-2,5,7-trimethyl-3h-inden-1-one
(2s,3s)-3-hydroxy-6-(2-hydroxyethyl)-2,5-bis(hydroxymethyl)-7-methyl-2,3-dihydroinden-1-one
n-[3-(17-amino-1-hydroxy-1,5,9,14-tetraazaheptadecan-1-yl)propyl]-2-(4-hydroxy-1h-indol-3-yl)ethanimidic acid
n-[3-(17-amino-1-hydroxy-1,5,9,14-tetraazaheptadecan-1-yl)propyl]-2-(1h-indol-3-yl)ethanimidic acid
n-[5-({3-[(3-aminopropyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}butanediimidic acid
n-(3-{[3-({3-[(4-aminobutyl)amino]propyl}amino)propyl]amino}propyl)-4-hydroxybenzamide
n-[3-(17-amino-1-hydroxy-1,5,9,14-tetraazaheptadecan-1-yl)propyl]-2,5-dihydroxybenzenecarboximidic acid
(2s)-2-{[(2s)-5-amino-1-hydroxy-2-{[1-hydroxy-2-(4-hydroxy-1h-indol-3-yl)ethylidene]amino}pentylidene]amino}-n-{5-[(3-{[4-({3-[(4-aminobutyl)amino]-1-hydroxypropylidene}amino)butyl]amino}-1-hydroxypropylidene)amino]pentyl}butanediimidic acid
C38H65N11O7 (787.5068180000001)
(2e)-3,7-dimethylocta-2,6-dien-1-yl tetradecanoate
n-(4-{[3-({3-[(3-aminopropyl)amino]propyl}(hydroxy)amino)propyl](hydroxy)amino}butyl)-2-(4-hydroxy-1h-indol-2-yl)ethanimidic acid
C23H40N6O4 (464.31108800000004)
(2s)-n-[5-({3-[(4-{[(2r)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}butyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[1-hydroxy-2-(1h-indol-3-yl)ethylidene]amino}butanediimidic acid
n-(5-{[3-({4-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]butyl}amino)-1-hydroxypropylidene]amino}pentyl)-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
C30H52N10O7 (664.4020241999999)
(2z)-3,7-dimethylocta-2,6-dien-1-yl tetradecanoate
(2s)-n-(5-{[(2s)-5-amino-2-{[(2r)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxypentylidene]amino}pentyl)-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
(9r,10r)-7,15-diazatetracyclo[7.7.1.0²,⁷.0¹⁰,¹⁵]heptadeca-2,4-dien-6-one
(2s)-n-(5-{[3-({4-[(3-aminopropyl)amino]butyl}amino)-1-hydroxypropylidene]amino}pentyl)-2-{[1-hydroxy-2-(4-hydroxy-1h-indol-3-yl)ethylidene]amino}butanediimidic acid
C29H48N8O5 (588.3747477999999)
n-(20-amino-4,8,12,17-tetraazaicosan-1-yl)-2,5-dihydroxybenzenecarboximidic acid
(2s,3s)-2-{[(2r,6r)-6-[(1r,3as,3bs,7s,9ar,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-hydroxy-2-methylheptylidene]amino}-3-methylpentanoic acid
(3e)-11,12-dihydroxy-16-methyl-8-[(1e)-2-(4-methyl-3,6-dihydro-2h-pyran-2-yl)ethenyl]-14-methylidene-6,9,22-trioxatricyclo[16.3.1.1⁷,¹⁰]tricosa-3,20-dien-5-one
n-(20-amino-4,8,12,17-tetraazaicosan-1-yl)-2-(4-hydroxy-1h-indol-2-yl)ethanimidic acid
(2s,3r)-2,3-dihydroxy-6-(2-hydroxyethyl)-2,5,7-trimethyl-3h-inden-1-one
3-hydroxy-6-(2-hydroxyethyl)-2-(hydroxymethyl)-5,7-dimethyl-2,3-dihydroinden-1-one
n-[3-(17-amino-1-hydroxy-1,5,9,14-tetraazaheptadecan-1-yl)propyl]-2-(1h-indol-2-yl)ethanimidic acid
(1r,4r,5as,5br,7as,11as,11br,13r,13as)-1-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-3-oxo-1h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate
[(3as,4r,10as)-5,10,10-trihydroxy-2,6-diimino-hexahydropyrrolo[1,2-c]purin-4-yl]methoxycarboximidic acid
n-{3-[(3-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl](hydroxy)amino}propyl)(hydroxy)amino]propyl}-2-(4-hydroxy-1h-indol-2-yl)ethanimidic acid
6-{9a,11a-dimethyl-1h,2h,3h,3ah,3bh,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl}-2-methylheptan-2-ol
(2s,3s)-2-{[(6r)-6-[(1r,3as,3bs,7s,9ar,9bs,11ar)-9a,11a-dimethyl-7-(sulfooxy)-1h,2h,3h,3ah,3bh,4h,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-1-hydroxy-2-methylheptylidene]amino}-3-methylpentanoic acid
(1r,5as,5br,7as,11as,11br,13r,13as,13bs)-1-methoxy-5b,8,8,11a,13a-pentamethyl-1h,3h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-13-yl acetate
6-(1,2-dihydroxyethyl)-2,5,7-trimethyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroinden-1-one
n-{3-[(3-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl](hydroxy)amino}propyl)(hydroxy)amino]propyl}-2-(1h-indol-2-yl)ethanimidic acid
(2s)-2,6-diamino-n-[(1s)-1-{[(1r,4s,7s,10s,13r,18r,21s,24s,27s,30r,33s,39s,42s)-10-benzyl-33-[(2s)-butan-2-yl]-18-{[(1s)-4-carbamimidamido-1-(c-hydroxycarbonimidoyl)butyl]-c-hydroxycarbonimidoyl}-7,21,24,39-tetrakis(3-carbamimidamidopropyl)-3,6,9,12,20,23,26,29,32,35,38,41,44-tridecahydroxy-27,42-bis[(4-hydroxyphenyl)methyl]-4-isopropyl-15,16,46,47-tetrathia-2,5,8,11,19,22,25,28,31,34,37,40,43-tridecaazabicyclo[28.14.4]octatetraconta-2,5,8,11,19,22,25,28,31,34,37,40,43-tridecaen-13-yl]-c-hydroxycarbonimidoyl}-2-(1h-indol-3-yl)ethyl]hexanimidic acid
C99H151N35O19S4 (2262.0807776)
(3s)-3-{[(2s)-5-amino-1-hydroxy-2-{[1-hydroxy-2-(1h-indol-3-yl)ethylidene]amino}pentylidene]amino}-3-({5-[(3-{[4-({3-[(4-aminobutyl)amino]-1-hydroxypropylidene}amino)butyl]amino}-1-hydroxypropylidene)amino]pentyl}-c-hydroxycarbonimidoyl)propanoic acid
(1r,3as,3bs,9ar,9br,11ar)-9a,11a-dimethyl-1-[(2r)-6-methylheptan-2-yl]-1h,2h,3h,3ah,3bh,9h,9bh,10h,11h-cyclopenta[a]phenanthrene
(2s,3r)-2,3-dihydroxy-6-(2-hydroxyethyl)-5-(hydroxymethyl)-2,7-dimethyl-3h-inden-1-one
n-(3-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl](hydroxy)amino}propyl)-4-hydroxybenzamide
C20H37N5O3 (395.28962520000005)
n-(3-{[3-({3-[(4-aminobutyl)amino]propyl}amino)propyl](hydroxy)amino}propyl)-2-(4-hydroxy-1h-indol-2-yl)ethanimidic acid
C23H40N6O3 (448.31617300000005)
n-(3-{[3-({3-[(4-aminobutyl)amino]propyl}amino)propyl]amino}propyl)-2,5-dihydroxybenzenecarboximidic acid
C20H37N5O3 (395.28962520000005)
6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohexa-2,5-dien-1-one
n-[3-(17-amino-1-hydroxy-1,5,9,14-tetraazaheptadecan-1-yl)propyl]-2-(4-hydroxy-1h-indol-2-yl)ethanimidic acid
(3r,4r,5as,5br,7as,11as,11br,13r,13as)-3-hydroxy-4-methoxy-5b,8,8,11a,13a-pentamethyl-1-oxo-3h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-chryseno[1,2-c]furan-13-yl acetate
(2s)-n-[5-({3-[(4-{[(2s)-1-[(2-{[(2s)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxyethylidene)amino]-1-oxopropan-2-yl]amino}butyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
n-(4-{[3-({3-[(3-aminopropyl)amino]propyl}(hydroxy)amino)propyl](hydroxy)amino}butyl)-2-(1h-indol-2-yl)ethanimidic acid
C23H40N6O3 (448.31617300000005)
(2r)-n-[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
n-(3-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl](hydroxy)amino}propyl)-2-(4-hydroxy-1h-indol-3-yl)ethanimidic acid
C23H40N6O3 (448.31617300000005)
(1r,5as,5br,7as,11as,11br,13r,13as,13bs)-1-methoxy-5b,8,8,11a,13a-pentamethyl-1h,3h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-13-ol
n-(3-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]amino}propyl)-2-(1h-indol-2-yl)ethanimidic acid
n-(4-{[3-({3-[(3-aminopropyl)amino]propyl}amino)propyl](hydroxy)amino}butyl)-2-(1h-indol-2-yl)ethanimidic acid
(1r,5r,6r,7r,9s,11s,13s,14r)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol
n-(5-{[3-({3-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]propyl}amino)propyl]amino}pentyl)-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
C29H52N10O6 (636.4071091999999)
(2s,3s)-3-hydroxy-6-(2-hydroxyethyl)-5-(hydroxymethyl)-2,7-dimethyl-2,3-dihydroinden-1-one
(2s)-n-[5-({3-[(3-aminopropyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
3-[2-(3,4-dihydroxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]prop-2-enal
n-[5-({3-[(4-{[2-({2-[(2-amino-5-carbamimidamido-1-hydroxypentylidene)amino]-1-hydroxyethylidene}amino)-1-hydroxypropylidene]amino}butyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
(2s)-n-(5-{[(2s)-5-amino-2-{[(2s)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxypentylidene]amino}pentyl)-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
(2s,3s)-3-methyl-3-(4-methylpent-3-en-1-yl)oxirane-2-carbaldehyde
(2s,3s)-6-(2-hydroxyethyl)-2,5,7-trimethyl-3-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroinden-1-one
(2s)-n-[5-({3-[(3-aminopropyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[1-hydroxy-2-(4-hydroxyphenyl)ethylidene]amino}butanediimidic acid
(2s)-n-(5-{[3-({4-[(3-aminopropyl)amino]butyl}amino)-1-hydroxypropylidene]amino}pentyl)-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
n-(3-{[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl](hydroxy)amino}propyl)-2-(4-hydroxy-1h-indol-2-yl)ethanimidic acid
C23H40N6O3 (448.31617300000005)
3-hydroxy-6-(2-hydroxyethyl)-2,5-bis(hydroxymethyl)-7-methyl-2,3-dihydroinden-1-one
(2s)-n-(5-{[3-({3-[(3-{[4-({3-[(4-aminobutyl)amino]-1-hydroxypropylidene}amino)butyl]amino}-1-hydroxypropylidene)amino]propyl}amino)-1-hydroxypropylidene]amino}pentyl)-2-{[1-hydroxy-2-(4-hydroxy-1h-indol-3-yl)ethylidene]amino}butanediimidic acid
C39H67N11O7 (801.5224671999999)
(2s)-n-[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
(5as,5br,7ar,8r,11ar,11br,13r,13as,13br)-13-hydroxy-8-(hydroxymethyl)-5b,8,11a,13a-tetramethyl-1h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-3-one
6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9z,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohexa-2,5-dien-1-one
6-(2-hydroxyethyl)-2,5,7-trimethyl-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2,3-dihydroinden-1-one
n-(4-{[3-({3-[(3-aminopropyl)amino]propyl}amino)propyl]amino}butyl)-2-(1h-indol-2-yl)ethanimidic acid
2,3-dihydroxy-6-(2-hydroxyethyl)-5-(hydroxymethyl)-2,7-dimethyl-3h-inden-1-one
3-oxo-4-(prop-1-en-2-yl)cyclohex-1-ene-1-carbaldehyde
[(1r,5as,5br,7as,11ar,11bs,13r,13as,13bs)-1,13-dihydroxy-5b,8,8,13a-tetramethyl-1h,3h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h,13bh-chryseno[1,2-c]furan-11a-yl]methyl acetate
(3r)-2-[(1r,3as,5ar,7r,8s,9ar,11ar)-3a,7,8-trihydroxy-9a,11a-dimethyl-5-oxo-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-1-yl]-3,6-dihydroxy-6-methylheptan-3-yl (9z)-octadec-9-enoate
[(1s,4r,5as,5br,7as,11as,11br,13r,13as)-13-(acetyloxy)-1,4-dimethoxy-5b,8,8,11a,13a-pentamethyl-3-oxo-1h,4h,5h,5ah,6h,7h,7ah,9h,10h,11h,11bh,12h,13h-phenanthro[2,1-e]isoindol-2-yl]acetic acid
n-[3-({4-[(3-aminopropyl)amino]butyl}amino)propyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
(2s)-n-[5-({3-[(3-{[(2s)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}propyl)amino]propyl}amino)pentyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
C29H52N10O6 (636.4071091999999)
(2s,3s)-3-hydroxy-6-(2-hydroxyethyl)-2-(hydroxymethyl)-5,7-dimethyl-2,3-dihydroinden-1-one
n-(4-{[3-({3-[(3-aminopropyl)amino]propyl}(hydroxy)amino)propyl]amino}butyl)-2-(1h-indol-2-yl)ethanimidic acid
(1r,3as,5ar,7r,8s,9ar,11ar)-1-(2,6-dihydroxy-6-methylheptan-2-yl)-3a,7,8-trihydroxy-9a,11a-dimethyl-1h,2h,3h,5ah,6h,7h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-5-one
3-hydroxy-6-(2-hydroxyethyl)-5-(hydroxymethyl)-2,7-dimethyl-2,3-dihydroinden-1-one
6-hydroxy-2,4,4-trimethyl-3-[(1e,3e,5e,7e,9e,11e,13e,15e,17e)-3,7,12,16-tetramethyl-18-(2,6,6-trimethyl-3-oxocyclohex-1-en-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaen-1-yl]cyclohexa-2,5-dien-1-one
(1r,4z,8e,10z,12s,15r,17r)-17-hydroxy-17-[(4r)-2-hydroxy-4,5-dihydro-1,3-thiazol-4-yl]-5,12-dimethyl-2,16-dioxabicyclo[13.3.1]nonadeca-4,8,10-trien-3-one
C22H31NO5S (421.19228360000005)
n-(3-{[3-({3-[(4-aminobutyl)amino]propyl}amino)propyl]amino}propyl)-2-(1h-indol-2-yl)ethanimidic acid
(11s,13s)-14-(hydroxymethyl)-3-imino-8,10-dioxa-2,4-diazatetracyclo[7.3.1.1⁷,¹¹.0¹,⁶]tetradecane-5,9,12,13,14-pentol
n-[5-({3-[(3-aminopropyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
3-[(4a-hydroxy-1,2,5,5-tetramethyl-hexahydro-2h-naphthalen-1-yl)methyl]-2-hydroxy-5-methoxycyclohexa-2,5-diene-1,4-dione
n-(3-{[3-({4-[(3-aminopropyl)amino]butyl}(hydroxy)amino)propyl](hydroxy)amino}propyl)-2-(4-hydroxy-1h-indol-2-yl)ethanimidic acid
C23H40N6O4 (464.31108800000004)
6-(1,2-dihydroxyethyl)-3-hydroxy-2,5,7-trimethyl-2,3-dihydroinden-1-one
(2s)-n-(5-{[(2r)-5-amino-2-{[(2s)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}-1-hydroxypentylidene]amino}pentyl)-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
(2s)-2-{[(2s)-5-amino-1-hydroxy-2-{[1-hydroxy-2-(4-hydroxy-1h-indol-3-yl)ethylidene]amino}pentylidene]amino}-n-(5-{[3-({4-[(3-{[4-({3-[(4-aminobutyl)amino]-1-hydroxypropylidene}amino)butyl]amino}-1-hydroxypropylidene)amino]butyl}amino)-1-hydroxypropylidene]amino}pentyl)butanediimidic acid
C45H79N13O8 (929.6174254000001)
n-(3-{[3-({3-[(4-aminobutyl)amino]propyl}amino)propyl](hydroxy)amino}propyl)-2-(1h-indol-2-yl)ethanimidic acid
3a,6-dimethyl-3-(6-methylheptan-2-yl)-1h,2h,3h,4h,5h,7h,8h,11bh-cyclopenta[a]anthracene
(2s)-n-[5-({3-[(4-{[3-({4-[(3-{[4-({3-[(4-aminobutyl)amino]-1-hydroxypropylidene}amino)butyl]amino}-1-hydroxypropylidene)amino]butyl}amino)-1-hydroxypropylidene]amino}butyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[1-hydroxy-2-(4-hydroxy-1h-indol-3-yl)ethylidene]amino}butanediimidic acid
C47H83N13O8 (957.6487238000001)
(2s)-n-[5-({3-[(4-{[(2s)-2-amino-5-carbamimidamido-1-hydroxypentylidene]amino}butyl)amino]-1-hydroxypropylidene}amino)pentyl]-2-{[2-(2,4-dihydroxyphenyl)-1-hydroxyethylidene]amino}butanediimidic acid
C30H52N10O7 (664.4020241999999)