NCBI Taxonomy: 1312865

Vanillic acid

C8H8O4 (168.0422568)

Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavouring and scent agent that produces a pleasant, creamy odour. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea, and vanilla-flavoured confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity (PMID: 16899266). Vanillic acid is a microbial metabolite found in Amycolatopsis, Delftia, and Pseudomonas (PMID: 11152072, 10543794, 11728709, 9579070). Vanillic acid is a phenolic acid found in some forms of vanilla and many other plant extracts. It is a flavoring and scent agent that produces a pleasant, creamy odor. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). Vanillic acid, which is a chlorogenic acid, is an oxidized form of vanillin. It is also an intermediate in the production of vanillin from ferulic acid. Vanillic acid is a metabolic byproduct of caffeic acid and is often found in the urine of humans who have consumed coffee, chocolate, tea and vanilla-flavored confectionary. Vanillic acid selectively and specifically inhibits 5nucleotidase activity. (PMID: 16899266). Vanillic acid is a monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. It has a role as a plant metabolite. It is a monohydroxybenzoic acid and a methoxybenzoic acid. It is a conjugate acid of a vanillate. Vanillic acid is a natural product found in Ficus septica, Haplophyllum cappadocicum, and other organisms with data available. Vanillic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A flavoring agent. It is the intermediate product in the two-step bioconversion of ferulic acid to vanillin. (J Biotechnol 1996;50(2-3):107-13). A monohydroxybenzoic acid that is 4-hydroxybenzoic acid substituted by a methoxy group at position 3. Vanillic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=121-34-6 (retrieved 2024-06-29) (CAS RN: 121-34-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

Vanillin

C8H8O3 (152.0473418)

Vanillin, also known as vanillaldehyde or lioxin, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. It is used by the food industry as well as ethylvanillin. Vanillin exists in all living species, ranging from bacteria to humans. Vanillin is a sweet, chocolate, and creamy tasting compound. Vanillin is found, on average, in the highest concentration within a few different foods, such as corns, ryes, and sherries and in a lower concentration in beers, rums, and oats. Vanillin has also been detected, but not quantified, in several different foods, such as gooseberries, other bread, brazil nuts, shea tree, and ohelo berries. This could make vanillin a potential biomarker for the consumption of these foods. Vanillin is a potentially toxic compound. Synthetic vanillin, instead of natural Vanillin extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. Vanillin is the primary component of the extract of the Vanillin bean. Because of the scarcity and expense of natural Vanillin extract, there has long been interest in the synthetic preparation of its predominant component. Artificial Vanillin flavoring is a solution of pure vanillin, usually of synthetic origin. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Vanillin appears as white or very slightly yellow needles. Vanillin is a member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. It has a role as a plant metabolite, an anti-inflammatory agent, a flavouring agent, an antioxidant and an anticonvulsant. It is a member of phenols, a monomethoxybenzene and a member of benzaldehydes. Vanillin is a natural product found in Ficus erecta var. beecheyana, Pandanus utilis, and other organisms with data available. Vanillin is the primary component of the extract of the vanilla bean. Synthetic vanillin, instead of natural vanilla extract, is sometimes used as a flavouring agent in foods, beverages, and pharmaceuticals. It is used by the food industry as well as ethylvanillin.Artificial vanilla flavoring is a solution of pure vanillin, usually of synthetic origin. Because of the scarcity and expense of natural vanilla extract, there has long been interest in the synthetic preparation of its predominant component. The first commercial synthesis of vanillin began with the more readily available natural compound eugenol. Today, artificial vanillin is made from either guaiacol or from lignin, a constituent of wood which is a byproduct of the paper industry. (Wiki). Vanillin is a metabolite found in or produced by Saccharomyces cerevisiae. Constituent of vanilla (Vanilla subspecies) and many other plants, e.g. Peru balsam, clove bud oil. Widely used flavouring agent especies in cocoa products. obtained from spent wood-pulp liquors. Vanillin is found in many foods, some of which are pomes, elderberry, common cabbage, and dock. A member of the class of benzaldehydes carrying methoxy and hydroxy substituents at positions 3 and 4 respectively. D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; ML_ID 59 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

Luteolin

C15H10O6 (286.047736)

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)

C18H30O2 (278.224568)

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].

Aucubin

C15H22O9 (346.1263762)

Aucubin is found in common verbena. Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety. Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis. The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1 Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety.; Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.; Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis.; The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1. Aucubin is an organic molecular entity. It has a role as a metabolite. Aucubin is a natural product found in Verbascum lychnitis, Plantago media, and other organisms with data available. See also: Chaste tree fruit (part of); Rehmannia glutinosa Root (part of); Plantago ovata seed (part of). Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3]. Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3].

Salicylic acid

C7H6O3 (138.0316926)

Salicylic acid is a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. It is obtained from the bark of the white willow and wintergreen leaves. It has a role as an antiinfective agent, an antifungal agent, a keratolytic drug, an EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor, a plant metabolite, an algal metabolite and a plant hormone. It is a conjugate acid of a salicylate. It is a colorless solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone. The name is from Latin salix for willow tree. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates. Salicylic acid modulates COX1 enzymatic activity to decrease the formation of pro-inflammatory prostaglandins. Salicylate may competitively inhibit prostaglandin formation. Salicylates antirheumatic (nonsteroidal anti-inflammatory) actions are a result of its analgesic and anti-inflammatory mechanisms. Salicylic acid works by causing the cells of the epidermis to slough off more readily, preventing pores from clogging up, and allowing room for new cell growth. Salicylic acid inhibits the oxidation of uridine-5-diphosphoglucose (UDPG) competitively with nicotinamide adenosine dinucleotide and noncompetitively with UDPG. It also competitively inhibits the transferring of glucuronyl group of uridine-5-phosphoglucuronic acid to the phenolic acceptor. The wound-healing retardation action of salicylates is probably due mainly to its inhibitory action on mucopolysaccharide synthesis. Salicylic acid is biosynthesized from the amino acid phenylalanine. In Arabidopsis thaliana, it can be synthesized via a phenylalanine-independent pathway. Salicylic acid is an odorless white to light tan solid. Sinks and mixes slowly with water. (USCG, 1999) Salicylic acid is a monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. It is obtained from the bark of the white willow and wintergreen leaves. It has a role as an antiinfective agent, an antifungal agent, a keratolytic drug, an EC 1.11.1.11 (L-ascorbate peroxidase) inhibitor, a plant metabolite, an algal metabolite and a plant hormone. It is a conjugate acid of a salicylate. A compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics. Salicylic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Salicylic Acid is a beta hydroxy acid that occurs as a natural compound in plants. It has direct activity as an anti-inflammatory agent and acts as a topical antibacterial agent due to its ability to promote exfoliation. A compound obtained from the bark of the white willow and wintergreen leaves, and also prepared synthetically. It has bacteriostatic, fungicidal, and keratolytic actions. Its salts, the salicylates, are used as analgesics. A compound obtained from the bark of the white willow and wintergreen leaves. It has bacteriostatic, fungicidal, and keratolytic actions. See also: Benzoic Acid (has active moiety); Methyl Salicylate (active moiety of); Benzyl salicylate (is active moiety of) ... View More ... A monohydroxybenzoic acid that is benzoic acid with a hydroxy group at the ortho position. It is obtained from the bark of the white willow and wintergreen leaves. Salicylic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=69-72-7 (retrieved 2024-06-29) (CAS RN: 69-72-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Salicylic acid (2-Hydroxybenzoic acid) inhibits cyclo-oxygenase-2 (COX-2) activity independently of transcription factor (NF-κB) activation[1]. Salicylic acid (2-Hydroxybenzoic acid) inhibits cyclo-oxygenase-2 (COX-2) activity independently of transcription factor (NF-κB) activation[1].

Ursolic acid

C30H48O3 (456.36032579999994)

Ursolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. Ursolic acid (UA), a pentacyclic triterpene acid, has been isolated from many kinds of medicinal plants, such as Eriobotrya japonica, Rosmarinns officinalis, Melaleuca leucadendron, Ocimum sanctum and Glechoma hederaceae. UA has been reported to produce antitumor activities and antioxidant activity, and is reported to have an antioxidant activity. UA may play an important role in regulating the apoptosis induced by high glucose presumably through scavenging of ROS (reactive oxygen species). It has been found recently that ursolic acid treatment affects growth and apoptosis in cancer cells. (PMID: 15994040, 17516235, 17213663). Ursolic acid is a pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite and a geroprotector. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an ursane. Ursolic acid is a natural product found in Gladiolus italicus, Freziera, and other organisms with data available. Ursolic Acid is a pentacyclic triterpenoid found in various fruits, vegetables and medicinal herbs, with a variety of potential pharmacologic activities including anti-inflammatory, antioxidative, antiviral, serum lipid-lowering, and antineoplastic activities. Upon administration, ursolic acid may promote apoptosis and inhibit cancer cell proliferation through multiple mechanisms. This may include the regulation of mitochondrial function through various pathways including the ROCK/PTEN and p53 pathways, the suppression of the nuclear factor-kappa B (NF-kB) pathways, and the increase in caspase-3, caspase-8 and caspase-9 activities. See also: Holy basil leaf (part of); Jujube fruit (part of); Lagerstroemia speciosa leaf (part of). D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors A pentacyclic triterpenoid that is urs-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent Found in wax of apples, pears and other fruits. V. widely distributed in plants D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics C26170 - Protective Agent > C275 - Antioxidant D000893 - Anti-Inflammatory Agents D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents D004791 - Enzyme Inhibitors 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. 3-Epiursolic Acid is a triterpenoid that can be isolated from Eriobotrya japonica, acts as a competitive inhibitor of cathepsin L (IC50, 6.5 μM; Ki, 19.5 μM), with no obvious effect on cathepsin B[1]. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

Kaempferol

C15H10O6 (286.047736)

Kaempferol is a tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4. Acting as an antioxidant by reducing oxidative stress, it is currently under consideration as a possible cancer treatment. It has a role as an antibacterial agent, a plant metabolite, a human xenobiotic metabolite, a human urinary metabolite, a human blood serum metabolite and a geroprotector. It is a member of flavonols, a 7-hydroxyflavonol and a tetrahydroxyflavone. It is a conjugate acid of a kaempferol oxoanion. Kaempferol is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Kaempferol is a natural flavonoid which has been isolated from Delphinium, Witch-hazel, grapefruit, and other plant sources. Kaempferol is a yellow crystalline solid with a melting point of 276-278 degree centigrade. It is slightly soluble in water, and well soluble in hot ethanol and diethyl ether. Kaempferol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Cannabis sativa subsp. indica top (part of); Tussilago farfara flower (part of). Kaempferol, also known as rhamnolutein or c.i. 75640, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, kaempferol is considered to be a flavonoid molecule. A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4. Kaempferol is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Kaempferol exists in all eukaryotes, ranging from yeast to humans. Kaempferol is a bitter tasting compound. Kaempferol is found, on average, in the highest concentration within a few different foods, such as saffrons, capers, and cumins and in a lower concentration in lovages, endives, and cloves. Kaempferol has also been detected, but not quantified, in several different foods, such as shallots, pine nuts, feijoa, kombus, and chicory leaves. This could make kaempferol a potential biomarker for the consumption of these foods. Kaempferol is a potentially toxic compound. Very widespread in the plant world, e.g. in Brassicaceae, Apocynaceae, Dilleniaceae, Ranunculaceae, Leguminosae, etc. Found especies in broccoli, capers, chives, kale, garden cress, fennel, lovage, dill weed and tarragon [CCD] A tetrahydroxyflavone in which the four hydroxy groups are located at positions 3, 5, 7 and 4. Acting as an antioxidant by reducing oxidative stress, it is currently under consideration as a possible cancer treatment. CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3906; ORIGINAL_PRECURSOR_SCAN_NO 3905 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3916; ORIGINAL_PRECURSOR_SCAN_NO 3915 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3928; ORIGINAL_PRECURSOR_SCAN_NO 3927 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4291; ORIGINAL_PRECURSOR_SCAN_NO 4290 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3918; ORIGINAL_PRECURSOR_SCAN_NO 3917 CONFIDENCE standard compound; INTERNAL_ID 898; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3915; ORIGINAL_PRECURSOR_SCAN_NO 3914 Acquisition and generation of the data is financially supported in part by CREST/JST. INTERNAL_ID 2358; CONFIDENCE Reference Standard (Level 1) CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2358 CONFIDENCE standard compound; INTERNAL_ID 47 CONFIDENCE standard compound; ML_ID 45 Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4]. Kaempferol (Kempferol), a flavonoid found in many edible plants, inhibits estrogen receptor α expression in breast cancer cells and induces apoptosis in glioblastoma cells and lung cancer cells by activation of MEK-MAPK. Kaempferol can be uesd for the research of breast cancer[1][2][3][4].

4-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)

4-Hydroxybenzoic acid, also known as p-hydroxybenzoate or 4-carboxyphenol, belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 4-Hydroxybenzoic acid is a white crystalline solid that is slightly soluble in water and chloroform but more soluble in polar organic solvents such as alcohols and acetone. It is a nutty and phenolic tasting compound. 4-Hydroxybenzoic acid exists in all living species, ranging from bacteria to plants to humans. 4-Hydroxybenzoic acid can be found naturally in coconut. It is one of the main catechins metabolites found in humans after consumption of green tea infusions. It is also found in wine, in vanilla, in A√ßa√≠ oil, obtained from the fruit of the a√ßa√≠ palm (Euterpe oleracea), at relatively high concetrations (892¬±52 mg/kg). It is also found in cloudy olive oil and in the edible mushroom Russula virescens. It has been detected in red huckleberries, rabbiteye blueberries, and corianders and in a lower concentration in olives, red raspberries, and almonds. In humans, 4-hydroxybenzoic acid is involved in ubiquinone biosynthesis. In particular, the enzyme 4-hydroxybenzoate polyprenyltransferase uses a polyprenyl diphosphate and 4-hydroxybenzoate to produce diphosphate and 4-hydroxy-3-polyprenylbenzoate. This enzyme participates in ubiquinone biosynthesis. 4-Hydroxybenzoic acid can be biosynthesized by the enzyme Chorismate lyase. Chorismate lyase is an enzyme that transforms chorismate into 4-hydroxybenzoate and pyruvate. This enzyme catalyses the first step in ubiquinone biosynthesis in Escherichia coli and other Gram-negative bacteria. 4-Hydroxybenzoate is an intermediate in many enzyme-mediated reactions in microbes. For instance, the enzyme 4-hydroxybenzaldehyde dehydrogenase uses 4-hydroxybenzaldehyde, NAD+ and H2O to produce 4-hydroxybenzoate, NADH and H+. This enzyme participates in toluene and xylene degradation in bacteria such as Pseudomonas mendocina. 4-hydroxybenzaldehyde dehydrogenase is also found in carrots. The enzyme 4-hydroxybenzoate 1-hydroxylase transforms 4-hydroxybenzoate, NAD(P)H, 2 H+ and O2 into hydroquinone, NAD(P)+, H2O and CO2. This enzyme participates in 2,4-dichlorobenzoate degradation and is found in Candida parapsilosis. The enzyme 4-hydroxybenzoate 3-monooxygenase transforms 4-hydroxybenzoate, NADPH, H+ and O2 into protocatechuate, NADP+ and H2O. This enzyme participates in benzoate degradation via hydroxylation and 2,4-dichlorobenzoate degradation and is found in Pseudomonas putida and Pseudomonas fluorescens. 4-Hydroxybenzoic acid is a popular antioxidant in part because of its low toxicity. 4-Hydroxybenzoic acid has estrogenic activity both in vitro and in vivo (PMID 9417843). Isolated from many plants, free and combined. Alkyl esters of 4-hydroxybenzoic acid (see below) are used as food and cosmetic preservatives, mainly in their Na salt form, which makes them more water soluble. They are active at low concentrations and more pH-independent than the commonly used Benzoic acid DVN38-Z and 2,4-Hexadienoic acid GMZ10-P. The taste is more detectable than for those preservatives. Effectiveness increases with chain length of the alcohol, but for some microorganisms this reduces cell permeability and thus counteracts the increased efficiency. 4-Hydroxybenzoic acid is found in many foods, some of which are chicory, corn, rye, and black huckleberry. 4-hydroxybenzoic acid is a monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. It has a role as a plant metabolite and an algal metabolite. It is a conjugate acid of a 4-hydroxybenzoate. 4-Hydroxybenzoic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). See also: Vaccinium myrtillus Leaf (part of); Galium aparine whole (part of); Menyanthes trifoliata leaf (part of) ... View More ... A monohydroxybenzoic acid that is benzoic acid carrying a hydroxy substituent at C-4 of the benzene ring. 4-Hydroxybenzoic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-96-7 (retrieved 2024-07-01) (CAS RN: 99-96-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

Quercetin

C15H10O7 (302.042651)

Quercetin appears as yellow needles or yellow powder. Converts to anhydrous form at 203-207 °F. Alcoholic solutions taste very bitter. (NTP, 1992) Quercetin is a pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. It has a role as an antibacterial agent, an antioxidant, a protein kinase inhibitor, an antineoplastic agent, an EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor, a plant metabolite, a phytoestrogen, a radical scavenger, a chelator, an Aurora kinase inhibitor and a geroprotector. It is a pentahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a quercetin-7-olate. Quercetin is a flavonol widely distributed in plants. It is an antioxidant, like many other phenolic heterocyclic compounds. Glycosylated forms include RUTIN and quercetrin. Quercetin is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Quercetin is a flavonoid found in many foods and herbs and is a regular component of a normal diet. Extracts of quercetin have been used to treat or prevent diverse conditions including cardiovascular disease, hypercholesterolemia, rheumatic diseases, infections and cancer but have not been shown to be effective in clinical trials for any medical condition. Quercetin as a nutritional supplement is well tolerated and has not been linked to serum enzyme elevations or to episodes of clinically apparent liver injury. Quercetin is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. Quercetin is a polyphenolic flavonoid with potential chemopreventive activity. Quercetin, ubiquitous in plant food sources and a major bioflavonoid in the human diet, may produce antiproliferative effects resulting from the modulation of either EGFR or estrogen-receptor mediated signal transduction pathways. Although the mechanism of action of action is not fully known, the following effects have been described with this agent in vitro: decreased expression of mutant p53 protein and p21-ras oncogene, induction of cell cycle arrest at the G1 phase and inhibition of heat shock protein synthesis. This compound also demonstrates synergy and reversal of the multidrug resistance phenotype, when combined with chemotherapeutic drugs, in vitro. Quercetin also produces anti-inflammatory and anti-allergy effects mediated through the inhibition of the lipoxygenase and cyclooxygenase pathways, thereby preventing the production of pro-inflammatory mediators. Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercitin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adju... Quercetin is a flavonoid widely distributed in many plants and fruits including red grapes, citrus fruit, tomato, broccoli and other leafy green vegetables, and a number of berries, including raspberries and cranberries. Quercetin itself (aglycone quercetin), as opposed to quercetin glycosides, is not a normal dietary component. Quercetin glycosides are converted to phenolic acids as they pass through the gastrointestinal tract. Quercetin has neither been confirmed scientifically as a specific therapeutic for any condition nor been approved by any regulatory agency. The U.S. Food and Drug Administration has not approved any health claims for quercetin. Nevertheless, the interest in dietary flavonoids has grown after the publication of several epidemiological studies showing an inverse correlation between dietary consumption of flavonols and flavones and reduced incidence and mortality from cardiovascular disease and cancer. In recent years, a large amount of experimental and some clinical data have accumulated regarding the effects of flavonoids on the endothelium under physiological and pathological conditions. The meta-analysis of seven prospective cohort studies concluded that the individuals in the top third of dietary flavonol intake are associated with a reduced risk of mortality from coronary heart disease as compared with those in the bottom third, after adjustment for known risk factors and other dietary components. A limited number of intervention studies with flavonoids and flavonoid containing foods and extracts has been performed in several pathological conditions (PMID:17015250). Quercetin is isolated from many plants, especially fruits, such as Helichrysum, Euphorbia and Karwinskia spp. Present in the Solanaceae, Rhamnaceae, Passifloraceae and many other families. For example detected in almost all studied Umbelliferae. Nutriceutical with antiinflammatory props. and a positive influence on the blood lipid profile. Found in a wide variety of foods especially apples, bee pollen, blackcurrants, capers, cocoa, cranberries, dock leaves, elderberries, fennel, lovage, red onions, ancho peppers, dill weed and tarragon. A pentahydroxyflavone having the five hydroxy groups placed at the 3-, 3-, 4-, 5- and 7-positions. It is one of the most abundant flavonoids in edible vegetables, fruit and wine. COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4014; ORIGINAL_PRECURSOR_SCAN_NO 4012 INTERNAL_ID 298; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4019; ORIGINAL_PRECURSOR_SCAN_NO 4018 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4017; ORIGINAL_PRECURSOR_SCAN_NO 4016 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4011; ORIGINAL_PRECURSOR_SCAN_NO 4010 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4096; ORIGINAL_PRECURSOR_SCAN_NO 4094 CONFIDENCE standard compound; INTERNAL_ID 298; DATASET 20200303_ENTACT_RP_MIX505; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4024; ORIGINAL_PRECURSOR_SCAN_NO 4023 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB109_Quercetin_pos_30eV_CB000041.txt IPB_RECORD: 1761; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_pos_10eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_20eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_40eV_CB000041.txt [Raw Data] CB109_Quercetin_pos_50eV_CB000041.txt IPB_RECORD: 161; CONFIDENCE confident structure [Raw Data] CB109_Quercetin_neg_40eV_000027.txt [Raw Data] CB109_Quercetin_neg_50eV_000027.txt [Raw Data] CB109_Quercetin_neg_20eV_000027.txt [Raw Data] CB109_Quercetin_neg_30eV_000027.txt [Raw Data] CB109_Quercetin_neg_10eV_000027.txt CONFIDENCE standard compound; INTERNAL_ID 124 CONFIDENCE standard compound; ML_ID 54 Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

Palmitic acid

C16H32O2 (256.2402172)

Palmitic acid, also known as palmitate or hexadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, palmitic acid is considered to be a fatty acid lipid molecule. Palmitic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Palmitic acid can be found in a number of food items such as sacred lotus, spinach, shallot, and corn salad, which makes palmitic acid a potential biomarker for the consumption of these food products. Palmitic acid can be found primarily in most biofluids, including feces, sweat, cerebrospinal fluid (CSF), and urine, as well as throughout most human tissues. Palmitic acid exists in all living species, ranging from bacteria to humans. In humans, palmitic acid is involved in several metabolic pathways, some of which include alendronate action pathway, rosuvastatin action pathway, simvastatin action pathway, and cerivastatin action pathway. Palmitic acid is also involved in several metabolic disorders, some of which include hypercholesterolemia, familial lipoprotein lipase deficiency, ethylmalonic encephalopathy, and carnitine palmitoyl transferase deficiency (I). Moreover, palmitic acid is found to be associated with schizophrenia. Palmitic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Palmitic acid, or hexadecanoic acid in IUPAC nomenclature, is the most common saturated fatty acid found in animals, plants and microorganisms. Its chemical formula is CH3(CH2)14COOH, and its C:D is 16:0. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Palmitic acid can also be found in meats, cheeses, butter, and dairy products. Palmitate is the salts and esters of palmitic acid. The palmitate anion is the observed form of palmitic acid at physiologic pH (7.4) . Palmitic acid is the first fatty acid produced during lipogenesis (fatty acid synthesis) and from which longer fatty acids can be produced. Palmitate negatively feeds back on acetyl-CoA carboxylase (ACC) which is responsible for converting acetyl-ACP to malonyl-ACP on the growing acyl chain, thus preventing further palmitate generation (DrugBank). Palmitic acid, or hexadecanoic acid, is one of the most common saturated fatty acids found in animals, plants, and microorganisms. As its name indicates, it is a major component of the oil from the fruit of oil palms (palm oil). Excess carbohydrates in the body are converted to palmitic acid. Palmitic acid is the first fatty acid produced during fatty acid synthesis and is the precursor to longer fatty acids. As a consequence, palmitic acid is a major body component of animals. In humans, one analysis found it to make up 21–30\\\% (molar) of human depot fat (PMID: 13756126), and it is a major, but highly variable, lipid component of human breast milk (PMID: 352132). Palmitic acid is used to produce soaps, cosmetics, and industrial mould release agents. These applications use sodium palmitate, which is commonly obtained by saponification of palm oil. To this end, palm oil, rendered from palm tree (species Elaeis guineensis), is treated with sodium hydroxide (in the form of caustic soda or lye), which causes hydrolysis of the ester groups, yielding glycerol and sodium palmitate. Aluminium salts of palmitic acid and naphthenic acid were combined during World War II to produce napalm. The word "napalm" is derived from the words naphthenic acid and palmitic acid (Wikipedia). Palmitic acid is also used in the determination of water hardness and is a surfactant of Levovist, an intravenous ultrasonic contrast agent. Hexadecanoic acid is a straight-chain, sixteen-carbon, saturated long-chain fatty acid. It has a role as an EC 1.1.1.189 (prostaglandin-E2 9-reductase) inhibitor, a plant metabolite, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a hexadecanoate. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. Palmitic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Palmitic Acid is a saturated long-chain fatty acid with a 16-carbon backbone. Palmitic acid is found naturally in palm oil and palm kernel oil, as well as in butter, cheese, milk and meat. Palmitic acid, or hexadecanoic acid is one of the most common saturated fatty acids found in animals and plants, a saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. It occurs in the form of esters (glycerides) in oils and fats of vegetable and animal origin and is usually obtained from palm oil, which is widely distributed in plants. Palmitic acid is used in determination of water hardness and is an active ingredient of *Levovist*TM, used in echo enhancement in sonographic Doppler B-mode imaging and as an ultrasound contrast medium. A common saturated fatty acid found in fats and waxes including olive oil, palm oil, and body lipids. A straight-chain, sixteen-carbon, saturated long-chain fatty acid. Palmitic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-10-3 (retrieved 2024-07-01) (CAS RN: 57-10-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Betulin

C30H50O2 (442.38106)

Betulin is found in black elderberry. Betulin is a constituent of Corylus avellana (filbert) and Vicia faba. Betulin (lup-20(29)-ene-3 ,28-diol) is an abundant naturally occurring triterpene. It is commonly isolated from the bark of birch trees and forms up to 30\\\\\% of the dry weight of the extractive. The purpose of the compound in the bark is not known. It can be converted to betulinic acid (the alcohol group replaced by a carboxylic acid group), which is biologically more active than betulin itself. Chemically, betulin is a triterpenoid of lupane structure. It has a pentacyclic ring structure, and hydroxyl groups in positions C3 and C28 Betulin is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents. It has a role as a metabolite, an antiviral agent, an analgesic, an anti-inflammatory agent and an antineoplastic agent. It is a pentacyclic triterpenoid and a diol. It derives from a hydride of a lupane. Betulin is a natural product found in Diospyros morrisiana, Euonymus carnosus, and other organisms with data available. A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents. Constituent of Corylus avellana (filbert) and Vicia faba Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.

Betulinic acid

C30H48O3 (456.36032579999994)

Betulinic acid is a pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. It has a role as an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an anti-HIV agent, an antimalarial, an anti-inflammatory agent, an antineoplastic agent and a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of a lupane. Betulinic Acid has been used in trials studying the treatment of Dysplastic Nevus Syndrome. Betulinic acid is a natural product found in Ficus auriculata, Gladiolus italicus, and other organisms with data available. Betulinic Acid is a pentacyclic lupane-type triterpene derivative of betulin (isolated from the bark of Betula alba, the common white birch) with antiinflammatory, anti-HIV and antineoplastic activities. Betulinic acid induces apoptosis through induction of changes in mitochondrial membrane potential, production of reactive oxygen species, and opening of mitochondrial permeability transition pores, resulting in the release of mitochondrial apogenic factors, activation of caspases, and DNA fragmentation. Although originally thought to exhibit specific cytotoxicity against melanoma cells, this agent has been found to be cytotoxic against non-melanoma tumor cell types including neuroectodermal and brain tumor cells. A lupane-type triterpene derivative of betulin which was originally isolated from BETULA or birch tree. It has anti-inflammatory, anti-HIV and antineoplastic activities. See also: Jujube fruit (part of); Paeonia lactiflora root (part of). Betulinic acid is found in abiyuch. Betulinic acid is a naturally occurring pentacyclic triterpenoid which has anti-retroviral, anti-malarial, and anti-inflammatory properties, as well as a more recently discovered potential as an anticancer agent, by inhibition of topoisomerase. It is found in the bark of several species of plants, principally the white birch (Betula pubescens) from which it gets its name, but also the Ber tree (Ziziphus mauritiana), the tropical carnivorous plants Triphyophyllum peltatum and Ancistrocladus heyneanus, Diospyros leucomelas a member of the persimmon family, Tetracera boiviniana, the jambul (Syzygium formosanum), flowering quince (Chaenomeles sinensis), Rosemary, and Pulsatilla chinensis. Controversial is a role of p53 in betulinic acid-induced apoptosis. Fulda suggested p53-independent mechanism of the apoptosis, basing on fact of no accumulation of wild-type p53 detected upon treatment with the betulinic acid, whereas wild-type p53 protein strongly increased after treatment with doxorubicin. The suggestion is supported by study of Raisova. On the other hand Rieber suggested that betulinic acid exerts its inhibitory effect on human metastatic melanoma partly by increasing p53 A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-carboxy substituents. It is found in the bark and other plant parts of several species of plants including Syzygium claviflorum. It exhibits anti-HIV, antimalarial, antineoplastic and anti-inflammatory properties. C308 - Immunotherapeutic Agent > C2139 - Immunostimulant Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Epibetulinic acid exhibits potent inhibitory effects on NO and prostaglandin E2 (PGE2) production in mouse macrophages (RAW 264.7) stimulated with bacterial endotoxin with IC50s of 0.7 and 0.6 μM, respectively. Anti-inflammatory activity[1].

Oleanolic acid

C30H48O3 (456.36032579999994)

Oleanolic acid is a pentacyclic triterpene, found in the non-glyceride fraction of olive pomace oil (Olive pomace oil, also known as "orujo" olive oil, is a blend of refined-pomace oil and virgin olive oil, fit for human consumption). Pentacyclic triterpenes are natural compounds which are widely distributed in plants. These natural products have been demonstrated to possess anti-inflammatory properties. Triterpenoids have been reported to possess antioxidant properties, since they prevent lipid peroxidation and suppress superoxide anion generation. The triterpenes have a history of medicinal use in many Asian countries. Oleanolic acid exhibits both pro- and anti-inflammatory properties depending on chemical structure and dose and may be useful in modulating the immune response; further studies are required to confirm the immunomodulatory behaviour of this triterpenoid, and characterise the mechanisms underlying the biphasic nature of some aspects of the inflammatory response. Oleanolic acid is a ubiquitous triterpenoid in plant kingdom, medicinal herbs, and is an integral part of the human diet. During the last decade over 700 research articles have been published on triterpenoids research, reflecting tremendous interest and progress in our understanding of these compounds. This included the isolation and purification of these tritepernoids from various plants and herbs, the chemical modifications to make more effective and water soluble derivatives, the pharmacological research on their beneficial effects, the toxicity studies, and the clinical use of these triterpenoids in various diseases including anticancer chemotherapies. (PMID:17292619, 15522132, 15994040). Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane. Oleanolic acid is a natural product found in Ophiopogon japonicus, Freziera, and other organisms with data available. A pentacyclic triterpene that occurs widely in many PLANTS as the free acid or the aglycone for many SAPONINS. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. See also: Holy basil leaf (part of); Jujube fruit (part of); Paeonia lactiflora root (part of) ... View More ... Occurs as glycosides in cloves (Syzygium aromaticum), sugar beet (Beta vulgaris), olive leaves, etc. Very widely distributed aglycone A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. [Raw Data] CBA90_Oleanolic-acid_neg_50eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_20eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_10eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_30eV.txt [Raw Data] CBA90_Oleanolic-acid_neg_40eV.txt Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities. Oleanolic acid (Caryophyllin) is a natural compound from plants with anti-tumor activities.

p-Anisic acid

C8H8O3 (152.0473418)

p-Anisic acid, also known as 4-anisate or draconic acid, belongs to the class of organic compounds known as p-methoxybenzoic acids and derivatives. These are benzoic acids in which the hydrogen atom at position 4 of the benzene ring is replaced by a methoxy group. p-Anisic acid is a drug. p-Anisic acid exists in all eukaryotes, ranging from yeast to humans. p-Anisic acid is a faint, sweet, and cadaverous tasting compound. Outside of the human body, p-anisic acid has been detected, but not quantified in several different foods, such as anises, cocoa beans, fennels, and german camomiles. This could make p-anisic acid a potential biomarker for the consumption of these foods. It is a white crystalline solid which is insoluble in water, highly soluble in alcohols and soluble in ether, and ethyl acetate. p-Anisic acid has antiseptic properties. It is also used as an intermediate in the preparation of more complex organic compounds. It is generally obtained by the oxidation of anethole or p-methoxyacetophenone. The term "anisic acid" often refers to this form specifically. p-Anisic acid is found naturally in anise. 4-methoxybenzoic acid is a methoxybenzoic acid substituted with a methoxy group at position C-4. It has a role as a plant metabolite. It is functionally related to a benzoic acid. It is a conjugate acid of a 4-methoxybenzoate. 4-Methoxybenzoic acid is a natural product found in Chaenomeles speciosa, Annona purpurea, and other organisms with data available. Anisic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Stevia rebaudiuna Leaf (part of). Flavouring agent. Food additive listed in the EAFUS Food Additive Database (Jan. 2001) A methoxybenzoic acid substituted with a methoxy group at position C-4. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS KEIO_ID A154 p-Anisic acid (4-Methoxybenzoic acid) is one of the isomers of anisic acid, with anti-bacterial and antiseptic properties[1]. p-Anisic acid (4-Methoxybenzoic acid) is one of the isomers of anisic acid, with anti-bacterial and antiseptic properties[1].

Amyrin

C30H50O (426.386145)

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

1-Hydroxyanthraquinone

C14H8O3 (224.0473418)

CONFIDENCE standard compound; INTERNAL_ID 8284 CONFIDENCE standard compound; INTERNAL_ID 25 D009676 - Noxae > D002273 - Carcinogens 1-Hydroxyanthraquinone, a naturally occurring compound with oral activity from some plants like Tabebuia avellanedae, exhibits carcinogenic effect[1]. 1-Hydroxyanthraquinone, a naturally occurring compound with oral activity from some plants like Tabebuia avellanedae, exhibits carcinogenic effect[1].

Stearic acid

C18H36O2 (284.2715156)

Stearic acid, also known as stearate or N-octadecanoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, stearic acid is considered to be a fatty acid lipid molecule. Stearic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Stearic acid can be synthesized from octadecane. Stearic acid is also a parent compound for other transformation products, including but not limited to, 3-oxooctadecanoic acid, (9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoic acid, and 16-methyloctadecanoic acid. Stearic acid can be found in a number of food items such as green bell pepper, common oregano, ucuhuba, and babassu palm, which makes stearic acid a potential biomarker for the consumption of these food products. Stearic acid can be found primarily in most biofluids, including urine, feces, cerebrospinal fluid (CSF), and sweat, as well as throughout most human tissues. Stearic acid exists in all living species, ranging from bacteria to humans. In humans, stearic acid is involved in the plasmalogen synthesis. Stearic acid is also involved in mitochondrial beta-oxidation of long chain saturated fatty acids, which is a metabolic disorder. Moreover, stearic acid is found to be associated with schizophrenia. Stearic acid is a non-carcinogenic (not listed by IARC) potentially toxic compound. Stearic acid ( STEER-ik, stee-ARR-ik) is a saturated fatty acid with an 18-carbon chain and has the IUPAC name octadecanoic acid. It is a waxy solid and its chemical formula is C17H35CO2H. Its name comes from the Greek word στέαρ "stéar", which means tallow. The salts and esters of stearic acid are called stearates. As its ester, stearic acid is one of the most common saturated fatty acids found in nature following palmitic acid. The triglyceride derived from three molecules of stearic acid is called stearin . Stearic acid, also known as octadecanoic acid or C18:0, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Stearic acid (its ester is called stearate) is a saturated fatty acid that has 18 carbons and is therefore a very hydrophobic molecule that is practically insoluble in water. It exists as a waxy solid. In terms of its biosynthesis, stearic acid is produced from carbohydrates via the fatty acid synthesis machinery wherein acetyl-CoA contributes two-carbon building blocks, up to the 16-carbon palmitate, via the enzyme complex fatty acid synthase (FA synthase), at which point a fatty acid elongase is needed to further lengthen it. After synthesis, there are a variety of reactions it may undergo, including desaturation to oleate via stearoyl-CoA desaturase (PMID: 16477801). Stearic acid is found in all living organisms ranging from bacteria to plants to animals. It is one of the useful types of saturated fatty acids that comes from many animal and vegetable fats and oils. For example, it is a component of cocoa butter and shea butter. It is used as a food additive, in cleaning and personal care products, and in lubricants. Its name comes from the Greek word stear, which means ‚Äòtallow‚Äô or ‚Äòhard fat‚Äô. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Oleic acid

C18H34O2 (282.2558664)

Oleic acid (or 9Z)-Octadecenoic acid) is an unsaturated C-18 or an omega-9 fatty acid that is the most widely distributed and abundant fatty acid in nature. It occurs naturally in various animal and vegetable fats and oils. It is an odorless, colorless oil, although commercial samples may be yellowish. The name derives from the Latin word oleum, which means oil. Oleic acid is the most abundant fatty acid in human adipose tissue, and the second most abundant in human tissues overall, following palmitic acid. Oleic acid is a component of the normal human diet, being a part of animal fats and vegetable oils. Triglycerides of oleic acid represent the majority of olive oil (about 70\\\\%). Oleic acid triglycerides also make up 59–75\\\\% of pecan oil, 61\\\\% of canola oil, 36–67\\\\% of peanut oil, 60\\\\% of macadamia oil, 20–80\\\\% of sunflower oil, 15–20\\\\% of grape seed oil, sea buckthorn oil, 40\\\\% of sesame oil, and 14\\\\% of poppyseed oil. High oleic variants of plant sources such as sunflower (~80\\\\%) and canola oil (70\\\\%) also have been developed. consumption has been associated with decreased low-density lipoprotein (LDL) cholesterol, and possibly with increased high-density lipoprotein (HDL) cholesterol, however, the ability of oleic acid to raise HDL is still debated. Oleic acid may be responsible for the hypotensive (blood pressure reducing) effects of olive oil that is considered a health benefit. Oleic acid is used in manufacturing of surfactants, soaps, plasticizers. It is also used as an emulsifying agent in foods and pharmaceuticals. Oleic acid is used commercially in the preparation of oleates and lotions, and as a pharmaceutical solvent. Major constituent of plant oils e.g. olive oil (ca. 80\\\\%), almond oil (ca. 80\\\\%) and many others, mainly as glyceride. Constituent of tall oiland is also present in apple, melon, raspberry oil, tomato, banana, roasted peanuts, black tea, rice bran, cardamon, plum brandy, peated malt, dairy products and various animal fats. Component of citrus fruit coatings. Emulsifying agent in foods CONFIDENCE standard compound; INTERNAL_ID 290 COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

Lapachol

C15H14O3 (242.0942894)

Lapachol is a hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae. It has a role as a plant metabolite, an antineoplastic agent, an antibacterial agent and an anti-inflammatory agent. It is a hydroxy-1,4-naphthoquinone and an olefinic compound. NA is a natural product found in Plenckia populnea, Stereospermum colais, and other organisms with data available. A hydroxy-1,4-naphthoquinone that is 1,4-naphthoquinone substituted by hydroxy and 3-methylbut-2-en-1-yl groups at positions 2 and 3, respectively. It is a natural compound that exhibits antibacterial and anticancer properties, first isolated in 1882 from the bark of Tabebuia avellanedae. D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents [Raw Data] CB290_Lapachol_pos_40eV_CB000086.txt [Raw Data] CB290_Lapachol_pos_50eV_CB000086.txt [Raw Data] CB290_Lapachol_pos_10eV_CB000086.txt [Raw Data] CB290_Lapachol_pos_30eV_CB000086.txt [Raw Data] CB290_Lapachol_pos_20eV_CB000086.txt [Raw Data] CB290_Lapachol_neg_10eV_000049.txt [Raw Data] CB290_Lapachol_neg_20eV_000049.txt [Raw Data] CB290_Lapachol_neg_40eV_000049.txt [Raw Data] CB290_Lapachol_neg_50eV_000049.txt [Raw Data] CB290_Lapachol_neg_30eV_000049.txt Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2]. Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2].

beta-Lapachone

C15H14O3 (242.0942894)

[Raw Data] CB138_beta-Lapachone_pos_30eV_CB000050.txt [Raw Data] CB138_beta-Lapachone_pos_50eV_CB000050.txt [Raw Data] CB138_beta-Lapachone_pos_10eV_CB000050.txt [Raw Data] CB138_beta-Lapachone_pos_20eV_CB000050.txt [Raw Data] CB138_beta-Lapachone_pos_40eV_CB000050.txt β-Lapachone (ARQ-501;NSC-26326) is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression. β-Lapachone (ARQ-501;NSC-26326) is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression.

Astragalin

C21H20O11 (448.100557)

Kaempferol 3-O-beta-D-glucoside is a kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage. It has a role as a trypanocidal drug and a plant metabolite. It is a kaempferol O-glucoside, a monosaccharide derivative, a trihydroxyflavone and a beta-D-glucoside. It is a conjugate acid of a kaempferol 3-O-beta-D-glucoside(1-). Astragalin is a natural product found in Xylopia aromatica, Ficus virens, and other organisms with data available. See also: Moringa oleifera leaf (has part). Astragalin is found in alcoholic beverages. Astragalin is present in red wine. It is isolated from many plant species.Astragalin is a 3-O-glucoside of kaempferol. Astragalin is a chemical compound. It can be isolated from Phytolacca americana (the American pokeweed). A kaempferol O-glucoside in which a glucosyl residue is attached at position 3 of kaempferol via a beta-glycosidic linkage. Present in red wine. Isolated from many plant subspecies Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 173 Astragalin (Astragaline) a flavonoid with anti-inflammatory, antioxidant, anticancer, bacteriostatic activity. Astragalin inhibits cancer cells proliferation and migration, induces apoptosis. Astragalin is orally active and provides nerve and heart protection, and resistance against and osteoporosis[1]. Astragalin (Astragaline) a flavonoid with anti-inflammatory, antioxidant, anticancer, bacteriostatic activity. Astragalin inhibits cancer cells proliferation and migration, induces apoptosis. Astragalin is orally active and provides nerve and heart protection, and resistance against and osteoporosis[1].

Tectochrysin

C16H12O4 (268.0735552)

7-methylchrysin, also known as 5-hydroxy-7-methoxyflavone or techtochrysin, is a member of the class of compounds known as 7-o-methylated flavonoids. 7-o-methylated flavonoids are flavonoids with methoxy groups attached to the C7 atom of the flavonoid backbone. Thus, 7-methylchrysin is considered to be a flavonoid lipid molecule. 7-methylchrysin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 7-methylchrysin can be found in pine nut, prunus (cherry, plum), sour cherry, and sweet cherry, which makes 7-methylchrysin a potential biomarker for the consumption of these food products. relative retention time with respect to 9-anthracene Carboxylic Acid is 1.330 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.324 Tectochrysin (Techtochrysin) is one of the major flavonoids of Alpinia oxyphylla Miquel. Tectochrysin inhibits activity of NF-κB. Tectochrysin (Techtochrysin) is one of the major flavonoids of Alpinia oxyphylla Miquel. Tectochrysin inhibits activity of NF-κB.

Lampranthin II

C27H30O16 (610.153378)

Panasenoside, also known as lilyn, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Panasenoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Panasenoside can be found in tea, which makes panasenoside a potential biomarker for the consumption of this food product. Kaempferol 3-O-sophoroside, a derivative of Kaempferol, is isolated from the leaves of cultivated mountain ginseng (Panax ginseng) with anti-inflammatory effects[1]. Kaempferol 3-O-sophoroside, a derivative of Kaempferol, is isolated from the leaves of cultivated mountain ginseng (Panax ginseng) with anti-inflammatory effects[1].

Scutellarein

C15H10O6 (286.047736)

Scutellarein is a natural flavonoid compound with anti-inflammatory effects. Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

6-Hydroxymellein

C10H10O4 (194.057906)

Lapachenole

C16H16O2 (240.1150236)

Lapachenole is a member of the class of compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Lapachenole is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Lapachenole can be found in mexican oregano, which makes lapachenole a potential biomarker for the consumption of this food product.

6-Hydroxyluteolin

C15H10O7 (302.042651)

Isolated from Valerianella eriocarpa (Italian corn salad). 6-Hydroxyluteolin is found in many foods, some of which are common thyme, mexican oregano, green vegetables, and lemon verbena. 6-Hydroxyluteolin is found in common thyme. 6-Hydroxyluteolin is isolated from Valerianella eriocarpa (Italian corn salad).

Deoxylapachol

C15H14O2 (226.09937440000002)

2-demethylmenaquinone is a naphthoquinone and a member of p-quinones. It has a role as an Escherichia coli metabolite. Deoxylapachol is a natural product found in Tectona grandis, Handroanthus impetiginosus, and other organisms with data available. Deoxylapachol is a major cytotoxic component of New Zealand brown alga, Landsburgia quercifolia. Deoxylapachol has antifungal and anti-cancer activity[1]. Deoxylapachol is a major cytotoxic component of New Zealand brown alga, Landsburgia quercifolia. Deoxylapachol has antifungal and anti-cancer activity[1].

2-Hydroxymethylanthraquinone

C15H10O3 (238.062991)

2-hydroxymethylanthraquinone, also known as anthraquinone-2-methanol or hmaq-one, is a member of the class of compounds known as anthraquinones. Anthraquinones are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. 2-hydroxymethylanthraquinone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 2-hydroxymethylanthraquinone can be found in turmeric, which makes 2-hydroxymethylanthraquinone a potential biomarker for the consumption of this food product. 2-(Hydroxymethyl)anthraquinone is used as a photoremovable protecting group (PRPG) to chemically cage sex pheromone (e.g. (Z)-11-hexadecen-1-ol (sex pheromone of?Chilo infuscatellussnellen))[1]. 2-(Hydroxymethyl)anthraquinone is used as a photoremovable protecting group (PRPG) to chemically cage sex pheromone (e.g. (Z)-11-hexadecen-1-ol (sex pheromone of?Chilo infuscatellussnellen))[1].

Kigelinone

C14H10O5 (258.052821)

Gardenin B

C19H18O7 (358.10524780000003)

Gardenin b, also known as demethyltangeretin or 5-hydroxy-4,6,7,8-tetramethoxyflavone, is a member of the class of compounds known as 8-o-methylated flavonoids. 8-o-methylated flavonoids are flavonoids with methoxy groups attached to the C8 atom of the flavonoid backbone. Thus, gardenin b is considered to be a flavonoid lipid molecule. Gardenin b is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Gardenin b can be found in mandarin orange (clementine, tangerine), peppermint, sweet basil, and winter savory, which makes gardenin b a potential biomarker for the consumption of these food products. Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1]. Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1].

Trifolin

C21H20O11 (448.100557)

Kaempferol 3-o-beta-d-galactopyranoside, also known as trifolin or trifolioside, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-o-beta-d-galactopyranoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-o-beta-d-galactopyranoside can be found in horseradish, which makes kaempferol 3-o-beta-d-galactopyranoside a potential biomarker for the consumption of this food product. Kaempferol 3-O-beta-D-galactoside is a beta-D-galactoside compound with a 4,5,7-trihydroxychromen-3-yl group at the anomeric position. It has a role as a plant metabolite and an antifungal agent. It is a beta-D-galactoside, a monosaccharide derivative, a glycosyloxyflavone and a trihydroxyflavone. It is functionally related to a kaempferol. It is a conjugate acid of a kaempferol 3-O-beta-D-galactoside(1-). Trifolin is a natural product found in Lotus ucrainicus, Saxifraga tricuspidata, and other organisms with data available. Isoastragalin is found in fats and oils. Isoastragalin is isolated from Gossypium hirsutum (cotton) and other plant species. A beta-D-galactoside compound with a 4,5,7-trihydroxychromen-3-yl group at the anomeric position.

Kelampayoside A

C20H30O13 (478.168633)

3,4,5-trimethoxyphenyl-1-O-beta-D-apiofuranosyl-(1->6)-O-beta-D-glucopyranoside is a glycoside. It has a role as a metabolite. Kelampayoside A is a natural product found in Strychnos axillaris, Cinnamomum iners, and other organisms with data available. Kelampayoside A is found in chinese cinnamon. Kelampayoside A is isolated from Cinnamomum cassia (Chinese cinnamon). A natural product found in Acer saccharum.

Hydroxyanthraquinone

C14H8O3 (224.0473418)

1-hydroxyanthraquinone is a monohydroxyanthraquinone. 1-Hydroxyanthraquinone is a natural product found in Rheum palmatum, Handroanthus impetiginosus, and Morinda citrifolia with data available. D009676 - Noxae > D002273 - Carcinogens 1-Hydroxyanthraquinone, a naturally occurring compound with oral activity from some plants like Tabebuia avellanedae, exhibits carcinogenic effect[1]. 1-Hydroxyanthraquinone, a naturally occurring compound with oral activity from some plants like Tabebuia avellanedae, exhibits carcinogenic effect[1].

lapachol

C15H14O3 (242.0942894)

D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2]. Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2].

(+)-Cycloolivil

C20H24O7 (376.1521954)

(+)-cycloolivil is a member of the class of compounds known as 9,9p-dihydroxyaryltetralin lignans. 9,9p-dihydroxyaryltetralin lignans are lignans with a structure based on the 1-phenyltetralin skeleton carrying a hydroxyl group at the 9- and the 9- position (+)-cycloolivil is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-cycloolivil can be found in olive, which makes (+)-cycloolivil a potential biomarker for the consumption of this food product.

Scutellarein

C15H10O6 (286.047736)

Scutellarein is flavone substituted with hydroxy groups at C-4, -5, -6 and -7. It has a role as a metabolite. It is functionally related to an apigenin. It is a conjugate acid of a scutellarein(1-). Scutellarein is a natural product found in Scoparia dulcis, Artemisia douglasiana, and other organisms with data available. Flavone substituted with hydroxy groups at C-4, -5, -6 and -7. Scutellarein, also known as 6-hydroxyapigenin or 4,5,6,7-tetrahydroxyflavanone, is a member of the class of compounds known as flavones. Flavones are flavonoids with a structure based on the backbone of 2-phenylchromen-4-one (2-phenyl-1-benzopyran-4-one). Thus, scutellarein is considered to be a flavonoid lipid molecule. Scutellarein is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Scutellarein can be synthesized from apigenin. Scutellarein is also a parent compound for other transformation products, including but not limited to, scutellarin, 4,6-dihydroxy-5,7-dimethoxyflavone, and 6-hydroxy-4,5,7-trimethoxyflavone. Scutellarein is a bitter tasting compound found in mexican oregano and sweet orange, which makes scutellarein a potential biomarker for the consumption of these food products. Scutellarein is a flavone that can be found in Scutellaria lateriflora and other members of the genus Scutellaria, as well as the fern Asplenium belangeri . Scutellarein is a natural flavonoid compound with anti-inflammatory effects. Scutellarein is a natural flavonoid compound with anti-inflammatory effects.

α-Lapachone

C15H14O3 (242.0942894)

D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059005 - Topoisomerase II Inhibitors [Raw Data] CB137_alpha-Lapachone_pos_50eV_CB000049.txt D004791 - Enzyme Inhibitors [Raw Data] CB137_alpha-Lapachone_pos_40eV_CB000049.txt [Raw Data] CB137_alpha-Lapachone_pos_30eV_CB000049.txt [Raw Data] CB137_alpha-Lapachone_pos_20eV_CB000049.txt [Raw Data] CB137_alpha-Lapachone_pos_10eV_CB000049.txt α-Lapachone shows trypanocidal activity[1]. α-Lapachone shows trypanocidal activity[1].

Astragalin

C21H20O11 (448.100557)

Astragalin (Astragaline) a flavonoid with anti-inflammatory, antioxidant, anticancer, bacteriostatic activity. Astragalin inhibits cancer cells proliferation and migration, induces apoptosis. Astragalin is orally active and provides nerve and heart protection, and resistance against and osteoporosis[1]. Astragalin (Astragaline) a flavonoid with anti-inflammatory, antioxidant, anticancer, bacteriostatic activity. Astragalin inhibits cancer cells proliferation and migration, induces apoptosis. Astragalin is orally active and provides nerve and heart protection, and resistance against and osteoporosis[1].

Ursolic Acid

C30H48O3 (456.36032579999994)

Origin: Plant; SubCategory_DNP: Triterpenoids relative retention time with respect to 9-anthracene Carboxylic Acid is 1.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.640 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.638 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.642 Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy. Ursolic acid (Prunol) is a natural pentacyclic triterpenoid carboxylic acid, exerts anti-tumor effects and is an effective compound for cancer prevention and therapy.

1-Methoxynapthalene

C11H10O (158.073161)

1-Methoxynaphthalene is used as the substrate to investigate the activity of cytochrome c peroxidase (CcP). 1-Methoxynaphthalene also can be used to synthesize prenyl naphthalen-ols[1][2].

Napabucasin

C14H8O4 (240.0422568)

C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor

Palmitic Acid

C16H32O2 (256.2402172)

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

veratric acid

C9H10O4 (182.057906)

Veratric acid (3,4-Dimethoxybenzoic acid) is an orally active phenolic compound derived from vegetables and fruits, has antioxidant[1] and anti-inflammatory activities[3]. Veratric acid also acts as a protective agent against hypertension-associated cardiovascular remodelling[2]. Veratric acid reduces upregulated COX-2 expression, and levels of PGE2, IL-6 after UVB irradiation[3]. Veratric acid (3,4-Dimethoxybenzoic acid) is an orally active phenolic compound derived from vegetables and fruits, has antioxidant[1] and anti-inflammatory activities[3]. Veratric acid also acts as a protective agent against hypertension-associated cardiovascular remodelling[2]. Veratric acid reduces upregulated COX-2 expression, and levels of PGE2, IL-6 after UVB irradiation[3].

(+)-Vernolic acid

C18H32O3 (296.2351322)

An optically active form of vernolic acid having (12S,13R)-configuration.

Pilloin

C17H14O6 (314.0790344)

Luteolin 4,7-dimethyl ether is a 3-hydroxyflavonoid, a dimethoxyflavone and a dihydroxyflavone. Pilloin is a natural product found in Chromolaena odorata, Alnus japonica, and other organisms with data available.

sitosterol

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].

2-(1-hydroxyethyl)-6-methoxynaphtho[2,3-b]furan-4,9-dione

C15H12O5 (272.0684702)

2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione

C14H10O4 (242.057906)

2-acetyl-6-methoxynaphtho[2,3-b]furan-4,9-dione

C15H10O5 (270.052821)

Vanillin

C8H8O3 (152.0473418)

CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3579; ORIGINAL_PRECURSOR_SCAN_NO 3578 D002491 - Central Nervous System Agents > D000927 - Anticonvulsants D020011 - Protective Agents > D016587 - Antimutagenic Agents D020011 - Protective Agents > D000975 - Antioxidants CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3566; ORIGINAL_PRECURSOR_SCAN_NO 3561 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3549; ORIGINAL_PRECURSOR_SCAN_NO 3546 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3560; ORIGINAL_PRECURSOR_SCAN_NO 3556 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3573; ORIGINAL_PRECURSOR_SCAN_NO 3570 CONFIDENCE standard compound; INTERNAL_ID 952; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 3577; ORIGINAL_PRECURSOR_SCAN_NO 3575 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.504 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.503 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.500 Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine. Vanillin (p-Vanillin) is a single molecule extracted from vanilla beans and also a popular odor used widely in perfume, food and medicine.

Alnetin

C18H16O6 (328.0946836)

Gardenin B

C19H18O7 (358.10524780000003)

Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1]. Gardenin B is a flavonoid isolated from Gardenia jasminoides. Gardenin B induces cell death in human leukemia cells involves multiple caspases[1].

Luteolin

C15H10O6 (286.047736)

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].

Quercetin

C15H10O7 (302.042651)

Annotation level-1 COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials relative retention time with respect to 9-anthracene Carboxylic Acid is 0.898 D020011 - Protective Agents > D000975 - Antioxidants Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.902 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 1981; CONFIDENCE confident structure IPB_RECORD: 3301; CONFIDENCE confident structure IPB_RECORD: 3283; CONFIDENCE confident structure Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1]. Quercetin, a natural flavonoid, is a stimulator of recombinant SIRT1 and also a PI3K inhibitor with IC50 of 2.4 μM, 3.0 μM and 5.4 μM for PI3K γ, PI3K δ and PI3K β, respectively[1].

Trifolin

C21H20O11 (448.100557)

Isolated from Gossypium hirsutum (cotton) and other plant subspecies Isoastragalin is found in fats and oils. Isolated from liquorice (Glycyrrhiza glabra). Acetylastragalin is found in herbs and spices. Widespread occurrence in plant world, e.g. Pinus sylvestris (Scotch pine) and fruits of Scolymus hispanicus (Spanish salsify). Kaempferol 3-galactoside is found in many foods, some of which are horseradish, almond, peach, and tea.

2-acetyl-5-hydroxynaphtho[2,3-b]furan-4,9-dione

C14H8O5 (256.0371718)

2-(1-Hydroxyethyl)-8-methoxynaphtho[2,3-b]furan-4,9-dione

C15H12O5 (272.0684702)

Aucubin

C15H22O9 (346.1263762)

Aucubin is an organic molecular entity. It has a role as a metabolite. Aucubin is a natural product found in Verbascum lychnitis, Plantago media, and other organisms with data available. See also: Chaste tree fruit (part of); Rehmannia glutinosa Root (part of); Plantago ovata seed (part of). Origin: Plant; SubCategory_DNP: Monoterpenoids, Iridoid monoterpenoids SubCategory_DNP: Monoterpenoids, Iridoid monoterpenoids; Origin: Plant Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3]. Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3].

betulinic acid

C30H48O3 (456.36032579999994)

Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4]. Betulinic acid is a natural pentacyclic triterpenoid, acts as a eukaryotic topoisomerase I inhibitor, with an IC50 of 5 μM, and possesses anti-HIV, anti-malarial, anti-inflammatory and anti-tumor properties[1][2][3][4].

Phthiocol

C11H8O3 (188.0473418)

Oleanolic Acid

C30H48O3 (456.36032579999994)

Luteolin 7-O-glucoside

C21H20O11 (448.100557)

9,10-dioxo-9,10-dihydroanthracene-2-carbaldehyde

C15H8O3 (236.0473418)

CZODYZFOLUNSFR-UHFFFAOYSA-N

C15H10O3 (238.062991)

1-hydroxy-2-methyl-9,10-anthraquinone is a member of the class of hydroxyanthraquinones that is anthracene-9,10-dione substituted by a hydroxy group at position 1 and a methyl group at position 2. It has been isolated from the roots of Rubia yunnanensis. It has a role as a plant metabolite. 1-Hydroxy-2-methylanthraquinone is a natural product found in Prismatomeris tetrandra, Galium spurium, and other organisms with data available. A member of the class of hydroxyanthraquinones that is anthracene-9,10-dione substituted by a hydroxy group at position 1 and a methyl group at position 2. It has been isolated from the roots of Rubia yunnanensis.

2-Methylanthraquinone

C15H10O2 (222.06807600000002)

2-methylanthraquinone is an anthraquinone that is 9,10-anthraquinone in which the hydrogen at position 2 is substituted by a methyl group. It is functionally related to a 9,10-anthraquinone. 2-Methylanthraquinone is a natural product found in Clausena heptaphylla, Ophiorrhiza pumila, and other organisms with data available. Tectoquinone (2-Methylanthraquinone) is a SARSCoV-2 main protease inhibitor against COVID-19. Tectoquinone exhibits strong mosquito larvicidal activity with the LC50 values of 3.3 and 5.4 μg/ml against A. aegypti and A. albopictus in 24 h, respectively[1][2]. Tectoquinone (2-Methylanthraquinone) is a SARSCoV-2 main protease inhibitor against COVID-19. Tectoquinone exhibits strong mosquito larvicidal activity with the LC50 values of 3.3 and 5.4 μg/ml against A. aegypti and A. albopictus in 24 h, respectively[1][2].

HMAQ-one

C15H10O3 (238.062991)

2-(hydroxymethyl)anthraquinone is an anthraquinone. It has a role as a metabolite. 2-(Hydroxymethyl)anthraquinone is a natural product found in Rubia yunnanensis and Handroanthus impetiginosus with data available. 2-(Hydroxymethyl)anthraquinone is used as a photoremovable protecting group (PRPG) to chemically cage sex pheromone (e.g. (Z)-11-hexadecen-1-ol (sex pheromone of?Chilo infuscatellussnellen))[1]. 2-(Hydroxymethyl)anthraquinone is used as a photoremovable protecting group (PRPG) to chemically cage sex pheromone (e.g. (Z)-11-hexadecen-1-ol (sex pheromone of?Chilo infuscatellussnellen))[1].

Hyperoside

C21H20O12 (464.09547200000003)

[Raw Data] CB050_Hyperoside_neg_50eV_000016.txt [Raw Data] CB050_Hyperoside_neg_40eV_000016.txt [Raw Data] CB050_Hyperoside_neg_30eV_000016.txt [Raw Data] CB050_Hyperoside_neg_20eV_000016.txt [Raw Data] CB050_Hyperoside_neg_10eV_000016.txt [Raw Data] CB050_Hyperoside_pos_50eV_CB000024.txt [Raw Data] CB050_Hyperoside_pos_40eV_CB000024.txt [Raw Data] CB050_Hyperoside_pos_30eV_CB000024.txt [Raw Data] CB050_Hyperoside_pos_20eV_CB000024.txt [Raw Data] CB050_Hyperoside_pos_10eV_CB000024.txt Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2]. Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2].

4-hydroxybenzoate

C7H6O3 (138.03169259999999)

4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

Vanillic Acid

C8H8O4 (168.0422568)

Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

stearic acid

C18H36O2 (284.2715156)

Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils. Stearic acid is a long chain dietary saturated fatty acid which exists in many animal and vegetable fats and oils.

Oleic acid

C18H34O2 (282.2558664)

An octadec-9-enoic acid in which the double bond at C-9 has Z (cis) stereochemistry. Oleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=112-80-1 (retrieved 2024-07-16) (CAS RN: 112-80-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Elaidic acid is the major trans fat found in hydrogenated vegetable oils and can be used as a pharmaceutical solvent. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2]. Oleic acid (9-cis-Octadecenoic acid) is an abundant monounsaturated fatty acid[1]. Oleic acid is a Na+/K+ ATPase activator[2].

(2S,3S,4S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-bis(hydroxymethyl)-7-methoxy-3,4-dihydro-1H-naphthalene-2,6-diol

C20H24O7 (376.1521954)

p-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)

4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL. 4-Hydroxybenzoic acid, a phenolic derivative of benzoic acid, could inhibit most gram-positive and some gram-negative bacteria, with an IC50 of 160 μg/mL.

Betulin

C30H50O2 (442.38106)

Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line. Betulin (Trochol), is a sterol regulatory element-binding protein (SREBP) inhibitor with an IC50 of 14.5 μM in K562 cell line.

p-Anisic acid

C8H8O3 (152.0473418)

p-Anisic acid (4-Methoxybenzoic acid) is one of the isomers of anisic acid, with anti-bacterial and antiseptic properties[1]. p-Anisic acid (4-Methoxybenzoic acid) is one of the isomers of anisic acid, with anti-bacterial and antiseptic properties[1].

α-Linolenic acid

C18H30O2 (278.224568)

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].

3,4-Dimethoxybenzaldehyde

C9H10O3 (166.062991)

(2S,3S,4S)-4-(4-hydroxy-3-methoxyphenyl)-2,3-bis(hydroxymethyl)-7-methoxy-3,4-dihydro-1H-naphthalene-2,6-diol

C20H24O7 (376.1521954)

kaempferol 3-O-sophoroside

C27H30O16 (610.153378)

Annotation level-1

Hexadecanoic acid

C16H32O2 (256.2402172)

Octadecanoic acid

C18H36O2 (284.2715156)

A C18 straight-chain saturated fatty acid component of many animal and vegetable lipids. As well as in the diet, it is used in hardening soaps, softening plastics and in making cosmetics, candles and plastics.

β-Lapachone

C15H14O3 (242.0942894)

β-Lapachone (ARQ-501;NSC-26326) is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression. β-Lapachone (ARQ-501;NSC-26326) is a naturally occurring O-naphthoquinone, acts as a topoisomerase I inhibitor, and induces apoptosis by inhibiting cell cycle progression.

eudesmic acid

C10H12O5 (212.06847019999998)

3,4,5-Trimethoxybenzoic acid (Eudesmic acid;Trimethylgallic Acid) is a benzoic acid derivative. A building block in medicine and organic synthesis. 3,4,5-Trimethoxybenzoic acid (Eudesmic acid;Trimethylgallic Acid) is a benzoic acid derivative. A building block in medicine and organic synthesis.

Jyperin

C21H20O12 (464.09547200000003)

Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2]. Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2].

Kelampayoside A

C20H30O13 (478.168633)

Isolated from Cinnamomum cassia (Chinese cinnamon). Kelampayoside A is found in chinese cinnamon and herbs and spices.

4-methoxybenzoic acid

C8H8O3 (152.0473418)

1-BENZOFURAN-6-CARBALDEHYDE

C9H6O2 (146.0367776)

4-(4-hydroxy-3-methoxyphenyl)-2,3-bis(hydroxymethyl)-7-methoxy-1,2,3,4-tetrahydronaphthalene-2,6-diol

C20H24O7 (376.1521954)

Vanillate

C8H8O4 (168.0422568)

Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1]. Vanillic acid is a flavoring agent found in edible plants and fruits, also found in Angelica sinensis. Vanillic acid inhibits NF-κB activation. Anti-inflammatory, antibacterial, and chemopreventive effects[1].

linoleic

C18H32O2 (280.2402172)

Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1]. Linolelaidic acid (Linoelaidic acid), an omega-6 trans fatty acid, acts as a source of energy. Linolelaidic acid is an essential nutrient, adding in enteral, parenteral, and infant formulas. Linolelaidic acid can be used for heart diseases research[1].

Tecomin

C15H14O3 (242.0942894)

D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000871 - Anthelmintics D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D000970 - Antineoplastic Agents Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2]. Lapachol is a naphthoquinone that was first isolated from Tabebuia avellanedae (Bignoniaceae)[1]. Lapachol shows anti-abscess, anti-ulcer, antileishmanial, anticarcinomic, antiedemic, anti-inflammatory, antimalarial, antiseptic, antitumor, antiviral, antibacterial, antifungal and pesticidal activities[2].

Lapachenole

C16H16O2 (240.1150236)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

C28H34O13 (578.1999314)

2-hydroxy-3-(2-methylprop-1-en-1-yl)naphthalene-1,4-dione

C14H12O3 (228.0786402)

(1r,2r,3r,4s)-4-hydroxy-3-(hydroxymethyl)-4-methyl-2-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)cyclopentyl 4-methoxybenzoate

C23H34O11 (486.2101014)

4-hydroxy-3-(hydroxymethyl)-4-methyl-2-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)cyclopentyl 4-methoxybenzoate

C23H34O11 (486.2101014)

(1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

C23H30O11 (482.178803)

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methyl 4-methoxybenzoate

C24H26O11 (490.14750460000005)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 4-methoxybenzoate

C27H34O13 (566.1999314)

hydroxyethyl furanhydroxynaphthoquinone

C14H10O5 (258.052821)

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

C19H28O11 (432.16315380000003)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C27H34O14 (582.1948464)

5-hydroxy-2-[(1r)-1-hydroxyethyl]naphtho[2,3-b]furan-4,9-dione

C14H10O5 (258.052821)

8-hydroxy-2-(1-hydroxyethyl)naphtho[2,3-b]furan-4,9-dione

C14H10O5 (258.052821)

[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-{4-[(2s,3r)-4-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(hydroxymethyl)butyl]-2-methoxyphenoxy}oxan-2-yl]methyl 3,4-dimethoxybenzoate

C35H44O14 (688.2730924)

2-[(1r)-1-hydroxyethyl]-8-methoxynaphtho[2,3-b]furan-4,9-dione

C15H12O5 (272.0684702)

(1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H28O11 (468.16315380000003)

(1s,4ar,5r,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl (2e,6e)-8-hydroxy-2,6-dimethylocta-2,6-dienoate

C25H36O11 (512.2257506)

(1s,2r)-3-formyl-4-methyl-2-(2-oxoethyl)cyclopent-3-en-1-yl 4-methoxybenzoate

C17H18O5 (302.1154178)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 4-methoxybenzoate

C27H34O14 (582.1948464)

3,4-dihydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

C15H18O3 (246.1255878)

(26s)-26-(2-hydroxy-2-methylpropyl)-5,5-dimethyl-6,15-dioxahexacyclo[12.12.0.0²,⁷.0⁸,¹³.0¹⁶,²⁵.0¹⁸,²³]hexacosa-1(14),2(7),3,8,10,12,16(25),18,20,22-decaene-17,24-dione

C30H26O5 (466.17801460000004)

[(3s,4r,5r)-5-{[(2r,3s,4s,5r,6s)-6-(3,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-methoxybenzoate

C27H34O14 (582.1948464)

2-[(1r)-1-hydroxyethyl]-6-methoxynaphtho[2,3-b]furan-4,9-dione

C15H12O5 (272.0684702)

2-methoxy-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

C16H16O3 (256.10993859999996)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C28H36O14 (596.2104956000001)

1-methoxy-9,10-anthraquinone

C15H10O3 (238.062991)

2-acetyl-7,8-dimethoxynaphtho[2,3-b]furan-4,9-dione

C16H12O6 (300.06338519999997)

[(3s,4r,5r)-5-{[(2r,3s,4s,5r,6s)-6-{4-[(1r)-1,2-dihydroxyethyl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-methoxybenzoate

C28H36O15 (612.2054106)

[5-({6-[4-(1,2-dihydroxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3,4-dihydroxyoxolan-3-yl]methyl 3,4-dimethoxybenzoate

C29H38O16 (642.2159748)

(2s,3as,9s,9as)-9-hydroxy-2-(2-hydroxypropan-2-yl)-2h,3h,3ah,9h,9ah-naphtho[2,3-b]furan-4-one

C15H18O4 (262.1205028)

(2s,3s,5s)-3,4,5-trihydroxy-6-[(4-hydroxybenzoyloxy)methyl]oxan-2-yl 4-hydroxybenzoate

C20H20O10 (420.105642)

2,2-dimethyl-4ah,10ah-benzo[g]chromene-5,10-dione

C15H14O3 (242.0942894)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C28H36O14 (596.2104956000001)

{3,4,5-trihydroxy-6-[(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl)oxy]oxan-2-yl}methyl 4-methoxybenzoate

C24H26O11 (490.14750460000005)

2-{4-[1,3-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)propyl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C23H30O11 (482.178803)

(2s,3r,4s,5s,6r)-2-{4-[(1s,2s)-1,3-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)propyl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C23H30O11 (482.178803)

(2s,3r,4s,5s,6r)-2-{4-[(1s,2r)-1,3-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)propyl]-2-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C23H30O11 (482.178803)

(1s,4as,5s,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H28O11 (468.16315380000003)

[(3r,4r,5r)-3,4-dihydroxy-5-{[(2s,3r,4r,5s,6s)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

C28H34O13 (578.1999314)

(1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate

C25H34O13 (542.1999314)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4,5-trimethoxybenzoate

C29H38O15 (626.2210598)

(1s,4as,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

C23H30O11 (482.178803)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 3,4,5-trimethoxybenzoate

C29H38O15 (626.2210598)

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

C29H50O (414.386145)

(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl)methyl 3,4-dimethoxybenzoate

C29H38O16 (642.2159748)

[3,4,5-trihydroxy-6-(4-{4-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(hydroxymethyl)butyl}-2-methoxyphenoxy)oxan-2-yl]methyl 3,4-dimethoxybenzoate

C35H44O14 (688.2730924)

(1s,2r)-3-formyl-4-methyl-2-(2-oxoethyl)cyclopent-3-en-1-yl 3,4-dimethoxybenzoate

C18H20O6 (332.125982)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C28H36O15 (612.2054106)

(1r,2r,3r,4s)-4-hydroxy-3-(hydroxymethyl)-4-methyl-2-(2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)cyclopentyl 3,4-dimethoxybenzoate

C24H36O12 (516.2206656000001)

(3r)-6-{[(2s,3r,4s,5s,6r)-6-({[(2r,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

C21H28O13 (488.1529838)

[(3s,4r,5r)-5-{[(2r,3s,4s,5r,6s)-6-(3,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl]methyl 3,4-dimethoxybenzoate

C28H36O15 (612.2054106)

(5-hydroxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0²,⁴]dec-9-en-5-yl)methyl 4-methoxybenzoate

C23H28O12 (496.1580688)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 4-hydroxybenzoate

C26H32O14 (568.1791972)

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{4-[(2s,3r)-4-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(hydroxymethyl)butyl]-2-methoxyphenoxy}oxan-2-yl]methyl 3,4-dimethoxybenzoate

C35H44O14 (688.2730924)

[3,4,5-trihydroxy-6-(4-{4-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(hydroxymethyl)butyl}-2-methoxyphenoxy)oxan-2-yl]methyl 4-methoxybenzoate

C34H42O13 (658.2625282)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C28H36O15 (612.2054106)

(2r,4r)-4-hydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

C15H18O2 (230.1306728)

2-methyl-3-(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

C16H16O2 (240.1150236)

benzyl β-d-glucoside

C13H18O6 (270.11033280000004)

(1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dimethoxybenzoate

C24H32O12 (512.1893672)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[4-({[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-2-methoxyphenoxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C38H44O18 (788.2527524)

(2r,3s,5s)-2-{[(3s,5s,6s)-6-({6-[(1r,3ar,4r,6ar)-4-(2h-1,3-benzodioxol-5-yl)-3a,6a-dimethyl-tetrahydrofuro[3,4-c]furan-1-yl]-2h-1,3-benzodioxol-4-yl}oxy)-3,4-dihydroxy-5-{[(2s,3s,5s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}oxan-2-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C40H52O22 (884.2950092000001)

4,5-dihydroxy-2-(hydroxymethyl)-6-[2-methoxy-4-(1,2,3-trihydroxypropyl)phenoxy]oxan-3-yl 4-methoxybenzoate

C24H30O12 (510.173718)

7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H26O11 (466.14750460000005)

7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate

C25H34O13 (542.1999314)

[4-({6-[({3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl}oxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-3-methoxyphenyl]methyl 4-methoxybenzoate

C34H38O16 (702.2159748)

7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

C23H30O11 (482.178803)

[(3s,5s,6r)-6-{[(2s,3r,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxybenzoate

C19H26O13 (462.13733460000003)

2-[(1r,5r)-2-(hydroxymethyl)-3-methyl-5-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopent-2-en-1-yl]ethyl 4-hydroxybenzoate

C22H30O10 (454.183888)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4,5-trimethoxybenzoate

C29H38O15 (626.2210598)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4,5-trimethoxybenzoate

C31H38O17 (682.2108898)

(2s)-7-{[(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C27H32O13 (564.1842822)

[5-({6-[4-(1,2-dihydroxyethyl)-2-methoxyphenoxy]-3,4,5-trihydroxyoxan-2-yl}methoxy)-3,4-dihydroxyoxolan-3-yl]methyl 4-methoxybenzoate

C28H36O15 (612.2054106)

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C21H20O12 (464.09547200000003)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{4-[(4-hydroxybenzoyloxy)methyl]-2-methoxyphenoxy}oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C35H40O17 (732.226539)

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

C19H28O12 (448.1580688)

6-{[6-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-8-hydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

C21H28O13 (488.1529838)

(1s,4ar,5r,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H26O11 (466.14750460000005)

[(3s,4r,5r)-5-{[(2r,3s,4s,5r,6s)-6-{4-[(1r)-1,2-dihydroxyethyl]-2-methoxyphenoxy}-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl]methyl 3,4-dimethoxybenzoate

C29H38O16 (642.2159748)

2-hydroxy-3-methylanthracene-9,10-dione

C15H10O3 (238.062991)

(5-{[6-(3,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-methoxybenzoate

C27H34O14 (582.1948464)

(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(4-methoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl)methyl 3,4-dimethoxybenzoate

C27H34O14 (582.1948464)

3-formyl-4-methyl-2-(2-oxoethyl)cyclopent-3-en-1-yl 3,4-dimethoxybenzoate

C18H20O6 (332.125982)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl)oxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 4-methoxybenzoate

C29H34O15 (622.1897614000001)

2-acetyl-8-methoxynaphtho[2,3-b]furan-4,9-dione

C15H10O5 (270.052821)

(1s,4as,5s,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H26O11 (466.14750460000005)

2-(1-hydroxyethyl)-7,8-dimethoxynaphtho[2,3-b]furan-4,9-dione

C16H14O6 (302.0790344)

(4-{[(2s,3r,4s,5s,6r)-6-({[(2r,3r,4s)-3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-methoxyphenyl)methyl 4-methoxybenzoate

C34H38O16 (702.2159748)

(3,4-dihydroxy-5-{[3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl)methyl 4-methoxybenzoate

C28H36O15 (612.2054106)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methoxy}oxolan-3-yl]methyl 4-methoxybenzoate

C29H34O15 (622.1897614000001)

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

C29H48O (412.37049579999996)

(2r,3r,4r)-3,4-dihydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

C15H18O3 (246.1255878)

5-{6-hydroxy-2,2-dimethyl-3h,4h-naphtho[1,2-b]pyran-5-yl}-2,2-dimethyl-3h,4h-naphtho[1,2-b]pyran-6-ol

C30H30O4 (454.214398)

13,13,22,22-tetramethyl-2,11,14,23-tetraoxaheptacyclo[16.12.0.0³,¹⁶.0⁴,⁹.0¹⁰,¹⁵.0¹⁹,²⁴.0²⁵,³⁰]triaconta-1(18),3(16),4(9),5,7,10(15),19(24),20,25(30),26,28-undecaene-12,17-dione

C30H22O6 (478.1416312)

[(3r,4s,5s)-3,4-dihydroxy-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-{[(3s)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C30H36O16 (652.2003256)

4-hydroxy-3-(hydroxymethyl)-4-methyl-2-(2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethyl)cyclopentyl 3,4-dimethoxybenzoate

C24H36O12 (516.2206656000001)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-[4-({[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}methyl)-2-methoxyphenoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C38H44O18 (788.2527524)

(4-{[(2s,3r,4s,5s,6r)-6-({[(2r,3r,4s)-4-[(3,4-dimethoxybenzoyloxy)methyl]-3,4-dihydroxyoxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-methoxyphenyl)methyl 3,4-dimethoxybenzoate

C37H44O18 (776.2527524)

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{2-methoxy-4-[(1s,2s)-1,2,3-trihydroxypropyl]phenoxy}oxan-2-yl]methyl 4-hydroxybenzoate

C23H28O12 (496.1580688)

[4-({6-[({4-[(3,4-dimethoxybenzoyloxy)methyl]-3,4-dihydroxyoxolan-2-yl}oxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-3-methoxyphenyl]methyl 3,4-dimethoxybenzoate

C37H44O18 (776.2527524)

8-hydroxy-2-[(1r)-1-hydroxyethyl]naphtho[2,3-b]furan-4,9-dione

C14H10O5 (258.052821)

(2r)-5-hydroxy-2-(prop-1-en-2-yl)-2h,3h-naphtho[2,3-b]furan-4,9-dione

C15H12O4 (256.0735552)

3-formyl-4-methyl-2-(2-oxoethyl)cyclopent-3-en-1-yl 4-methoxybenzoate

C17H18O5 (302.1154178)

{3,4-dihydroxy-5-[(3,4,5-trihydroxy-6-{4-[(4-hydroxybenzoyloxy)methyl]-2-methoxyphenoxy}oxan-2-yl)methoxy]oxolan-3-yl}methyl 3,4-dimethoxybenzoate

C35H40O17 (732.226539)

2-acetyl-8-hydroxynaphtho[2,3-b]furan-4,9-dione

C14H8O5 (256.0371718)

[(1r,2s,4s,5s,6s,7s)-5-hydroxy-7-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,8-dioxatricyclo[4.4.0.0²,⁴]dec-9-en-5-yl]methyl 4-methoxybenzoate

C23H28O12 (496.1580688)

2-[(1r)-1-hydroxyethyl]-7,8-dimethoxynaphtho[2,3-b]furan-4,9-dione

C16H14O6 (302.0790344)

(3r)-8-hydroxy-3-methyl-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxan-2-yl]oxy}-3,4-dihydro-2-benzopyran-1-one

C21H28O13 (488.1529838)

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

C19H28O12 (448.1580688)

7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate

C23H30O12 (498.173718)

7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H28O11 (468.16315380000003)

(1r,2r)-3-formyl-4-methyl-2-(2-oxoethyl)cyclopent-3-en-1-yl 3,4-dimethoxybenzoate

C18H20O6 (332.125982)

[(3s,4r,5r)-5-{[(2r,3s,4s,5r,6s)-6-(2,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl]methyl 3,4-dimethoxybenzoate

C28H36O15 (612.2054106)

7-hydroxy-7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

C23H30O12 (498.173718)

(1s,3r,4ar,5r,7s,7as)-7-hydroxy-1,3-dimethoxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C18H24O7 (352.1521954)

[(3s,4r,5r)-5-{[(2s,3s,4r,5r,6r)-6-(3,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-methoxybenzoate

C27H34O14 (582.1948464)

(2s,3r,4r)-3,4-dihydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

C15H18O3 (246.1255878)

(5-{[6-(2,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl)methyl 3,4-dimethoxybenzoate

C28H36O15 (612.2054106)

[4-({6-[({3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl}oxy)methyl]-3,4,5-trihydroxyoxan-2-yl}oxy)-3-methoxyphenyl]methyl 3,4-dimethoxybenzoate

C35H40O17 (732.226539)

[(3s,4r,5r)-5-{[(2r,3s,4s,5r,6s)-6-(3,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl]methyl 4-hydroxybenzoate

C26H32O14 (568.1791972)

2-(prop-1-en-2-yl)-2h,3h-naphtho[2,3-b]furan-4,9-dione

C15H12O3 (240.0786402)

(4as,10as)-2,2-dimethyl-4ah,10ah-benzo[g]chromene-5,10-dione

C15H14O3 (242.0942894)

(1s,4as,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate

C25H34O13 (542.1999314)

(1s,4as,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dimethoxybenzoate

C24H32O12 (512.1893672)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C29H38O16 (642.2159748)

2-[(2s,3s,4s,5r,6r)-6-ethoxy-3,4,5-trihydroxyoxan-2-yl]-2-hydroxy-1-(4-hydroxyphenyl)ethanone

C15H20O8 (328.115812)

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{4-[(2s,3r)-4-hydroxy-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2-(hydroxymethyl)butyl]-2-methoxyphenoxy}oxan-2-yl]methyl 4-methoxybenzoate

C34H42O13 (658.2625282)

(1s,4ar,5r,7s,7ar)-7-hydroxy-7-methyl-1-{[(2s,3s,4s,5s,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4,5-trimethoxybenzoate

C25H34O13 (542.1999314)

(2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7as)-5-hydroxy-7-(hydroxymethyl)-1h,4ah,5h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O9 (346.1263762)

stigmast-5-en-3-ol, (3β)-

C29H50O (414.386145)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methoxy}oxolan-3-yl]methyl 4-methoxybenzoate

C28H36O15 (612.2054106)

6,6,27,27-tetramethyl-7,16,26-trioxaheptacyclo[15.11.1.0²,¹⁵.0³,⁸.0⁹,¹⁴.0¹⁸,²³.0²⁵,²⁹]nonacosa-1(28),2(15),3(8),4,9,11,13,17(29),18,20,22,24-dodecaen-24-ol

C30H24O4 (448.1674504)

(1s,2s,4s,5s,6r,10s)-2-(hydroxymethyl)-10-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

C24H28O12 (508.1580688)

7-{[4,5-dihydroxy-6-(hydroxymethyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl]oxy}-5-hydroxy-2-phenyl-2,3-dihydro-1-benzopyran-4-one

C27H32O13 (564.1842822)

26-(2-hydroxy-2-methylpropyl)-5,5-dimethyl-6,15-dioxahexacyclo[12.12.0.0²,⁷.0⁸,¹³.0¹⁶,²⁵.0¹⁸,²³]hexacosa-1(14),2(7),3,8,10,12,16(25),18,20,22-decaene-17,24-dione

C30H26O5 (466.17801460000004)

7-hydroxy-1,3-dimethoxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C18H24O7 (352.1521954)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 4-methoxybenzoate

C27H34O14 (582.1948464)

[(3s,5s,6s)-6-{[(2r,3s,5r)-2-(benzyloxy)-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxybenzoate

C26H32O13 (552.1842822)

23,23-dimethyl-12-(2-methylprop-1-en-1-yl)-13,22-dioxahexacyclo[12.12.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰.0²¹,²⁶]hexacosa-1(14),2(11),4,6,8,15,17,19,21(26),24-decaene-3,10-dione

C30H24O4 (448.1674504)

7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 3,4-dimethoxybenzoate

C24H32O12 (512.1893672)

3-[3,7-dimethoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal

C26H30O11 (518.178803)

[(3r,4s,5s)-3,4-dihydroxy-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-{4-[(4-hydroxybenzoyloxy)methyl]-2-methoxyphenoxy}oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C35H40O17 (732.226539)

[(3s,4r,5r)-5-{[(2s,3r,4r,5r,6r)-6-(3,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl]methyl 3,4-dimethoxybenzoate

C28H36O15 (612.2054106)

{3,4,5-trihydroxy-6-[2-methoxy-4-(1,2,3-trihydroxypropyl)phenoxy]oxan-2-yl}methyl 4-hydroxybenzoate

C23H28O12 (496.1580688)

2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-[2-(4-hydroxyphenyl)ethoxy]oxane-3,4,5-triol

C19H28O11 (432.16315380000003)

(4-{[(2s,3r,4s,5s,6r)-6-({[(2r,3r,4s)-3,4-dihydroxy-4-[(4-hydroxybenzoyloxy)methyl]oxolan-2-yl]oxy}methyl)-3,4,5-trihydroxyoxan-2-yl]oxy}-3-methoxyphenyl)methyl 3,4-dimethoxybenzoate

C35H40O17 (732.226539)

(1s,4as,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate

C23H30O12 (498.173718)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl)oxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C30H36O16 (652.2003256)

[(3r,4s,5s)-3,4-dihydroxy-5-{[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C29H36O14 (608.2104956000001)

(1s,3s,4ar,5r,7s,7as)-7-hydroxy-1,3-dimethoxy-7-methyl-hexahydro-1h-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C18H24O7 (352.1521954)

[(3r,4s,5s)-3,4-dihydroxy-5-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-{[(3s)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4,5-trimethoxybenzoate

C31H38O17 (682.2108898)

(1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxy-3-methoxybenzoate

C23H30O12 (498.173718)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C28H36O14 (596.2104956000001)

(2r,3s,4r,5r,6s)-4,5-dihydroxy-2-(hydroxymethyl)-6-{2-methoxy-4-[(1s,2s)-1,2,3-trihydroxypropyl]phenoxy}oxan-3-yl 4-methoxybenzoate

C24H30O12 (510.173718)

4-hydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

C15H18O2 (230.1306728)

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-{[(2s,3s,4s,5r,6r)-3,4,6-trihydroxy-5-{[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}oxan-2-yl]oxy}chromen-4-one

C25H26O16 (582.1220796)

5-hydroxy-2-(prop-1-en-2-yl)-2h,3h-naphtho[2,3-b]furan-4,9-dione

C15H12O4 (256.0735552)

(1r,2r)-3-formyl-4-methyl-2-(2-oxoethyl)cyclopent-3-en-1-yl 4-methoxybenzoate

C17H18O5 (302.1154178)

2-[(1s)-1-hydroxyethyl]naphtho[2,3-b]furan-4,9-dione

C14H10O4 (242.057906)

(5-{[6-(3,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl)methyl 4-hydroxybenzoate

C26H32O14 (568.1791972)

(2e)-3-[(2r,3s)-3,7-dimethoxy-2-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-2,3-dihydro-1-benzofuran-5-yl]prop-2-enal

C26H30O11 (518.178803)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[4-(hydroxymethyl)-2-methoxyphenoxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 4-hydroxybenzoate

C26H32O14 (568.1791972)

2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(2,4-dimethoxyphenoxy)oxane-3,4,5-triol

C19H28O12 (448.1580688)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 4-methoxybenzoate

C27H34O13 (566.1999314)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 4-methoxybenzoate

C27H34O13 (566.1999314)

(2r)-2-(prop-1-en-2-yl)-2h,3h-naphtho[2,3-b]furan-4,9-dione

C15H12O3 (240.0786402)

2-[2-(hydroxymethyl)-3-methyl-5-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}cyclopent-2-en-1-yl]ethyl 4-hydroxybenzoate

C22H30O10 (454.183888)

(5-{[6-(3,4-dimethoxyphenoxy)-3,4,5-trihydroxyoxan-2-yl]methoxy}-3,4-dihydroxyoxolan-3-yl)methyl 3,4-dimethoxybenzoate

C28H36O15 (612.2054106)

2,3-bis(3-methylbut-2-en-1-yl)naphthalene-1,4-dione

C20H22O2 (294.1619712)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 4-hydroxybenzoate

C26H32O13 (552.1842822)

(1s,4ar,5r,7s,7as)-7-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-methoxybenzoate

C23H30O12 (498.173718)

(3s)-6,8-dihydroxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

C10H10O4 (194.057906)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{[(3r)-8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl]oxy}oxan-2-yl]methoxy}oxolan-3-yl]methyl 3,4-dimethoxybenzoate

C30H36O16 (652.2003256)

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

C29H48O (412.37049579999996)

8-hydroxy-3-methyl-6-[(3,4,5-trihydroxy-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxan-2-yl)oxy]-3,4-dihydro-2-benzopyran-1-one

C21H28O13 (488.1529838)

7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl 8-hydroxy-2,6-dimethylocta-2,6-dienoate

C25H36O11 (512.2257506)

(2s,4s)-4-hydroxy-2-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-naphthalen-1-one

C15H18O2 (230.1306728)

2,2-dimethylbenzo[g]chromene-5,10-dione

C15H12O3 (240.0786402)

[(3s,4r,5r)-3,4-dihydroxy-5-{[(2r,3s,4s,5r,6r)-3,4,5-trihydroxy-6-[2-(4-hydroxyphenyl)ethoxy]oxan-2-yl]methoxy}oxolan-3-yl]methyl 4-hydroxybenzoate

C26H32O13 (552.1842822)

9-hydroxy-2-(2-hydroxypropan-2-yl)-2h,3h,3ah,9h,9ah-naphtho[2,3-b]furan-4-one

C15H18O4 (262.1205028)

[3,4-dihydroxy-5-({3,4,5-trihydroxy-6-[(8-hydroxy-3-methyl-1-oxo-3,4-dihydro-2-benzopyran-6-yl)oxy]oxan-2-yl}methoxy)oxolan-3-yl]methyl 3,4,5-trimethoxybenzoate

C31H38O17 (682.2108898)

2-({[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}methyl)-6-(3,4-dimethoxyphenoxy)oxane-3,4,5-triol

C19H28O12 (448.1580688)