NCBI Taxonomy: 41393

Quercitrin

C21H20O11 (448.1006)

Quercitrin, also known as quercimelin or quercitronic acid, belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. A quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. Quercitrin exists in all living organisms, ranging from bacteria to humans. Quercitrin is found, on average, in the highest concentration within a few different foods, such as lingonberries, american cranberries, and olives and in a lower concentration in common beans, tea, and welsh onions. Quercitrin has also been detected, but not quantified, in several different foods, such as guava, bilberries, common pea, apricots, and spearmints. Quercitrin is a quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. It has a role as an antioxidant, an antileishmanial agent, an EC 1.1.1.184 [carbonyl reductase (NADPH)] inhibitor, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor and a plant metabolite. It is a monosaccharide derivative, a tetrahydroxyflavone, an alpha-L-rhamnoside and a quercetin O-glycoside. It is a conjugate acid of a quercitrin-7-olate. Quercitrin is a natural product found in Xylopia emarginata, Lotus ucrainicus, and other organisms with data available. Quercitrin is a glycoside formed from the flavonoid quercetin and the deoxy sugar rhamnose. It is a constituent of the dye quercitron. Quercitrin is found in many foods, some of which are garden tomato (variety), kiwi, italian sweet red pepper, and guava. A quercetin O-glycoside that is quercetin substituted by a alpha-L-rhamnosyl moiety at position 3 via a glycosidic linkage. [Raw Data] CBA03_Quercitrin_pos_10eV.txt [Raw Data] CBA03_Quercitrin_pos_20eV.txt [Raw Data] CBA03_Quercitrin_neg_50eV.txt [Raw Data] CBA03_Quercitrin_neg_30eV.txt [Raw Data] CBA03_Quercitrin_neg_10eV.txt [Raw Data] CBA03_Quercitrin_neg_40eV.txt [Raw Data] CBA03_Quercitrin_neg_20eV.txt [Raw Data] CBA03_Quercitrin_pos_50eV.txt [Raw Data] CBA03_Quercitrin_pos_30eV.txt [Raw Data] CBA03_Quercitrin_pos_40eV.txt Quercitrin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=522-12-3 (retrieved 2024-07-09) (CAS RN: 522-12-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2]. Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2]. Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2].

Naringenin

C15H12O5 (272.0685)

Naringenin is a flavorless, colorless flavanone, a type of flavonoid. It is the predominant flavanone in grapefruit, and is found in a variety of fruits and herbs. Naringenin has the skeleton structure of a flavanone with three hydroxy groups at the 4, 5, and 7 carbons. It may be found both in the aglycol form, naringenin, or in its glycosidic form, naringin, which has the addition of the disaccharide neohesperidose attached via a glycosidic linkage at carbon 7. Naringenin (not to be confused with naringin) is a flavanone that is considered to have a bioactive effect on human health as antioxidant, free radical scavenger, antiinflammatory, carbohydrate metabolism promoter, immunity system modulater. This substance has also been shown to repair DNA. Scientists exposed cells to 80 micomoles of naringenin per liter, for 24 hours, and found that the amount of hydroxyl damage to the DNA was reduced by 24 percent in that very short period of time. Unfortunately, this bioflavonoid is difficult to absorb on oral ingestion. Only 15\\\\\\\% of ingested naringenin will get absorbed, in the human gastrointestinal tract, in the best case scenario. A full glass of orange juice will supply about enough naringenin to achieve a concentration of about 0.5 micromoles per liter. Naringenin is a biomarker for the consumption of citrus fruits. (S)-naringenin is the (S)-enantiomer of naringenin. It has a role as an expectorant and a plant metabolite. It is a naringenin and a (2S)-flavan-4-one. It is a conjugate acid of a (S)-naringenin(1-). It is an enantiomer of a (R)-naringenin. Naringenin is a natural product found in Elaeodendron croceum, Garcinia multiflora, and other organisms with data available. See also: Naringin (related). Most widely distributed flavanone. Citrus fruits (grapefruit, oranges and pummelos) are especially good sources. Glycosides also widely distributed The (S)-enantiomer of naringenin. [Raw Data] CB070_Naringenin_pos_20eV_CB000030.txt [Raw Data] CB070_Naringenin_pos_10eV_CB000030.txt [Raw Data] CB070_Naringenin_pos_40eV_CB000030.txt [Raw Data] CB070_Naringenin_pos_30eV_CB000030.txt [Raw Data] CB070_Naringenin_pos_50eV_CB000030.txt [Raw Data] CB070_Naringenin_neg_10eV_000021.txt [Raw Data] CB070_Naringenin_neg_30eV_000021.txt [Raw Data] CB070_Naringenin_neg_50eV_000021.txt [Raw Data] CB070_Naringenin_neg_20eV_000021.txt [Raw Data] CB070_Naringenin_neg_40eV_000021.txt (±)-Naringenin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=67604-48-2 (retrieved 2024-07-09) (CAS RN: 67604-48-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

Vanillic acid

C8H8O4 (168.0423)

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].

Luteolin

C15H10O6 (286.0477)

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 (278.2246)

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 (346.1264)

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].

Coniferaldehyde

C10H10O3 (178.063)

Coniferaldehyde (CAS: 458-36-6), also known as 4-hydroxy-3-methoxycinnamaldehyde or ferulaldehyde, 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. Coniferaldehyde is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, coniferaldehyde is found, on average, in the highest concentration within sherries. Coniferaldehyde has also been detected, but not quantified in, several different foods, such as highbush blueberries, lima beans, Chinese cabbages, loquats, and greenthread tea. This could make coniferaldehyde a potential biomarker for the consumption of these foods. BioTransformer predicts that coniferaldehyde is a product of caffeic aldehyde metabolism via a catechol-O-methylation-pattern2 reaction catalyzed by the enzyme catechol O-methyltransferase (PMID: 30612223). Coniferyl aldehyde, also known as 4-hydroxy-3-methoxycinnamaldehyde or 4-hm-ca, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferyl aldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Coniferyl aldehyde can be found in a number of food items such as pear, common walnut, kelp, and citrus, which makes coniferyl aldehyde a potential biomarker for the consumption of these food products. Coniferyl aldehyde is a low molecular weight phenolic compound susceptible to be extracted from cork stoppers into wine . Coniferyl aldehyde is a member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3. It has a role as an antifungal agent and a plant metabolite. It is a member of cinnamaldehydes, a phenylpropanoid and a member of guaiacols. It is functionally related to an (E)-cinnamaldehyde. 4-Hydroxy-3-methoxycinnamaldehyde is a natural product found in Pandanus utilis, Microtropis japonica, and other organisms with data available. A member of the class of cinnamaldehydes that is cinnamaldehyde substituted by a hydroxy group at position 4 and a methoxy group at position 3. Acquisition and generation of the data is financially supported in part by CREST/JST. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1]. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells Coniferaldehyde. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=458-36-6 (retrieved 2024-09-04) (CAS RN: 458-36-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Ursolic acid

C30H48O3 (456.3603)

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.

Chrysosplenetin

C19H18O8 (374.1002)

Chrysosplenetin, also known as quercetagetin 3,6,7,3-tetramethyl ether or 3,6,7,3-tetra-methylquercetagetin, 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, chrysosplenetin is considered to be a flavonoid lipid molecule. Chrysosplenetin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Chrysosplenetin can be found in german camomile, which makes chrysosplenetin a potential biomarker for the consumption of this food product. Chrysosplenetin is an O-methylated flavonol. It can be found in the root of Berneuxia thibetica and in Chamomilla recutita . Chrysosplenetin is a tetramethoxyflavone that is the 3,6,7,3-tetramethyl ether derivative of quercetagetin. It has a role as an antiviral agent and a plant metabolite. It is a tetramethoxyflavone and a dihydroxyflavone. It is functionally related to a quercetagetin. Chrysosplenetin is a natural product found in Haplophyllum myrtifolium, Cleome amblyocarpa, and other organisms with data available. Chrysosplenetin is one of the polymethoxylated flavonoids in Artemisia annua L. (Compositae) and other several Chinese herbs. Chrysosplenetin inhibits P-gp activity and reverses the up-regulated P-gp and MDR1 levels induced by artemisinin (ART). Chrysosplenetin significantly augments the rat plasma level and anti-malarial efficacy of ART, partially due to the uncompetitive inhibition effect of Chrysosplenetin on rat CYP3A[1]. Chrysosplenetin is one of the polymethoxylated flavonoids in Artemisia annua L. (Compositae) and other several Chinese herbs. Chrysosplenetin inhibits P-gp activity and reverses the up-regulated P-gp and MDR1 levels induced by artemisinin (ART). Chrysosplenetin significantly augments the rat plasma level and anti-malarial efficacy of ART, partially due to the uncompetitive inhibition effect of Chrysosplenetin on rat CYP3A[1].

Apigenin

C15H10O5 (270.0528)

Apigenin is a trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. It has a role as a metabolite and an antineoplastic agent. It is a conjugate acid of an apigenin-7-olate. Apigenin is a natural product found in Verbascum lychnitis, Carex fraseriana, and other organisms with data available. Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter and the increase in hINV promoter activity. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes. (A7924). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin. (A7925). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis. (A7926). 5,7,4-trihydroxy-flavone, one of the FLAVONES. See also: Chamomile (part of); Cannabis sativa subsp. indica top (part of); Fenugreek seed (part of). Apigenin is a plant-derived flavonoid that has significant promise as a skin cancer chemopreventive agent. Apigenin inhibits the expression of involucrin (hINV), a marker of keratinocyte differentiation, is increased by differentiating agents via a protein kinase Cdelta (PKCdelta), Ras, MEKK1, and MEK3 cascade that increases AP1 factor level and AP1 factor binding to DNA elements in the hINV promoter. Apigenin suppresses the 12-O-tetradeconylphorbol-13-acetate-dependent increase in AP1 factor expression and binding to the hINV promoter. Apigenin also inhibits the increase in promoter activity observed following overexpression of PKCdelta, constitutively active Ras, or MEKK1. The suppression of PKCdelta activity is associated with reduced phosphorylation of PKCdelta-Y311. Activation of hINV promoter activity by the green tea polyphenol, (-)-epigellocathecin-3-gallate, is also inhibited by apigenin, suggesting that the two chemopreventive agents can produce opposing actions in keratinocytes (PMID: 16982614). Apigenin, a flavone abundantly found in fruits and vegetables, exhibits antiproliferative, anti-inflammatory, and antimetastatic activities through poorly defined mechanisms. This flavonoid provides selective activity to promote caspase-dependent-apoptosis of leukemia cells and uncover an essential role of PKCdelta during the induction of apoptosis by apigenin (PMID: 16844095). Apigenin markedly induces the expression of death receptor 5 (DR5) and synergistically acts with exogenous soluble recombinant human tumor necrosis factor-related apoptosis-inducing ligand (TRAIL) to induce apoptosis in malignant tumor cells. On the other hand, apigenin-mediated induction of DR5 expression is not observed in normal human peripheral blood mononuclear cells. Moreover, apigenin does not sensitize normal human peripheral blood mononuclear cells to TRAIL-induced apoptosis (PMID: 16648565). Flavone found in a wide variety of foodstuffs; buckwheat, cabbage, celeriac, celery, lettuce, oregano, parsley, peppermint, perilla, pummelo juice, thyme, sweet potatoes, green tea and wild carrot [DFC] A trihydroxyflavone that is flavone substituted by hydroxy groups at positions 4, 5 and 7. It induces autophagy in leukaemia cells. CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 771; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CB002_Apigenin_pos_10eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_40eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_20eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_30eV_CB000005.txt [Raw Data] CB002_Apigenin_pos_50eV_CB000005.txt [Raw Data] CB002_Apigenin_neg_40eV_000005.txt [Raw Data] CB002_Apigenin_neg_20eV_000005.txt [Raw Data] CB002_Apigenin_neg_10eV_000005.txt [Raw Data] CB002_Apigenin_neg_50eV_000005.txt CONFIDENCE standard compound; INTERNAL_ID 151 [Raw Data] CB002_Apigenin_neg_30eV_000005.txt CONFIDENCE standard compound; ML_ID 26 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

Vitexin 6'-O-malonyl 2'-O-xyloside

C21H20O10 (432.1056)

Vitexin 6-o-malonyl 2-o-xyloside, also known as apigenin 8-C-glucoside or 8-glycosyl-apigenin, is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin 6-o-malonyl 2-o-xyloside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vitexin 6-o-malonyl 2-o-xyloside can be synthesized from apigenin. Vitexin 6-o-malonyl 2-o-xyloside is also a parent compound for other transformation products, including but not limited to, vitexin 2-O-beta-L-rhamnoside, 7-O-methylvitexin 2-O-beta-L-rhamnoside, and vitexin 2-O-beta-D-glucoside. Vitexin 6-o-malonyl 2-o-xyloside can be found in common beet, which makes vitexin 6-o-malonyl 2-o-xyloside a potential biomarker for the consumption of this food product. Vitexin, also known as apigenin 8-C-glucoside or 8-glycosylapigenin, belongs to the class of organic compounds known as flavonoid 8-C-glycosides. Flavonoid 8-C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is also described as an apigenin flavone glucoside. Vitexin has been found in passion flower, chasteberry, bamboo leaves, millet and Hawthorn. Vitexin has shown a wide range of pharmacological effects, such as antioxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects (PMID: 27693342). Vitexin has also been shown to directly inhibit thyroid peroxidase and potentially contributes to goiter (PMID: 1696490). It is sometimes called a goitrogen. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA68_Vitexin_neg_10eV.txt [Raw Data] CBA68_Vitexin_neg_30eV.txt [Raw Data] CBA68_Vitexin_pos_20eV.txt [Raw Data] CBA68_Vitexin_neg_50eV.txt [Raw Data] CBA68_Vitexin_neg_40eV.txt [Raw Data] CBA68_Vitexin_pos_40eV.txt [Raw Data] CBA68_Vitexin_pos_30eV.txt [Raw Data] CBA68_Vitexin_pos_10eV.txt [Raw Data] CBA68_Vitexin_neg_20eV.txt Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

Eriodictyol

C15H12O6 (288.0634)

Eriodictyol, also known as 3,4,5,7-tetrahydroxyflavanone or 2,3-dihydroluteolin, belongs to the class of organic compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Thus, eriodictyol is considered to be a flavonoid lipid molecule. Outside of the human body, eriodictyol has been detected, but not quantified in, several different foods, such as common oregano, common thymes, parsley, sweet basils, and tarragons. This could make eriodictyol a potential biomarker for the consumption of these foods. Eriodictyol is a compound isolated from Eriodictyon californicum and can be used in medicine as an expectorant. BioTransformer predicts that eriodictiol is a product of luteolin metabolism via a flavonoid-c-ring-reduction reaction catalyzed by an unspecified-gut microbiota enzyme (PMID: 30612223). Eriodictyol, also known as 5735-tetrahydroxyflavanone, is a member of the class of compounds known as flavanones. Flavanones are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a ketone at the carbon C3. Eriodictyol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Eriodictyol can be found in a number of food items such as rowal, grape, cardamom, and lemon balm, which makes eriodictyol a potential biomarker for the consumption of these food products. Eriodictyol is a bitter-masking flavanone, a flavonoid extracted from yerba santa (Eriodictyon californicum), a plant native to North America. Eriodictyol is one of the four flavanones identified in this plant as having taste-modifying properties, the other three being homoeriodictyol, its sodium salt, and sterubin . Eriodictyol is a tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3 and 4 respectively. It is a tetrahydroxyflavanone and a member of 3-hydroxyflavanones. Eriodictyol is a natural product found in Eupatorium album, Eupatorium hyssopifolium, and other organisms with data available. A tetrahydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 7, 3 and 4 respectively. Acquisition and generation of the data is financially supported in part by CREST/JST. Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM. Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM.

4-Hydroxybenzoic acid

C7H6O3 (138.0317)

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 (302.0427)

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].

Lupeol

C30H50O (426.3861)

Lupeol is a pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. It has a role as an anti-inflammatory drug and a plant metabolite. It is a secondary alcohol and a pentacyclic triterpenoid. It derives from a hydride of a lupane. Lupeol has been investigated for the treatment of Acne. Lupeol is a natural product found in Ficus auriculata, Ficus septica, and other organisms with data available. See also: Calendula Officinalis Flower (part of). A pentacyclic triterpenoid that is lupane in which the hydrogen at the 3beta position is substituted by a hydroxy group. It occurs in the skin of lupin seeds, as well as in the latex of fig trees and of rubber plants. It is also found in many edible fruits and vegetables. D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

Afzelin

C21H20O10 (432.1056)

Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-). Afzelin is a natural product found in Premna odorata, Vicia tenuifolia, and other organisms with data available. [Raw Data] CBA27_Afzelin_neg_30eV_1-1_01_1585.txt [Raw Data] CBA27_Afzelin_pos_20eV_1-1_01_1549.txt [Raw Data] CBA27_Afzelin_pos_10eV_1-1_01_1540.txt [Raw Data] CBA27_Afzelin_neg_10eV_1-1_01_1576.txt [Raw Data] CBA27_Afzelin_neg_20eV_1-1_01_1584.txt [Raw Data] CBA27_Afzelin_neg_40eV_1-1_01_1586.txt [Raw Data] CBA27_Afzelin_pos_30eV_1-1_01_1550.txt [Raw Data] CBA27_Afzelin_pos_50eV_1-1_01_1552.txt [Raw Data] CBA27_Afzelin_pos_40eV_1-1_01_1551.txt [Raw Data] CBA27_Afzelin_neg_50eV_1-1_01_1587.txt Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

Betulin

C30H50O2 (442.3811)

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.

Sugiol

C20H28O2 (300.2089)

Sugiol is an abietane diterpenoid that is ferruginol in which the methylene group para to the phenolic hydroxy group has been substituted by an oxo group. It has a role as a plant metabolite, an antiviral agent, an antineoplastic agent, an antioxidant and a radical scavenger. It is an abietane diterpenoid, a carbotricyclic compound, a meroterpenoid, a member of phenols and a cyclic terpene ketone. It is functionally related to a ferruginol. Sugiol is a natural product found in Austrocedrus chilensis, Libocedrus bidwillii, and other organisms with data available. An abietane diterpenoid that is ferruginol in which the methylene group para to the phenolic hydroxy group has been substituted by an oxo group.

Ferruginol

C20H30O (286.2297)

Ferruginol is an abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12. It has a role as an antineoplastic agent, an antibacterial agent, a protective agent and a plant metabolite. It is an abietane diterpenoid, a member of phenols, a carbotricyclic compound and a meroterpenoid. Ferruginol is a natural product found in Calocedrus macrolepis, Teucrium polium, and other organisms with data available. An abietane diterpenoid that is abieta-8,11,13-triene substituted by a hydroxy group at positions 12.

Kaempferide

C16H12O6 (300.0634)

Kaempferide is a monomethoxyflavone that is the 4-O-methyl derivative of kaempferol. It has a role as an antihypertensive agent and a metabolite. It is a trihydroxyflavone, a monomethoxyflavone and a 7-hydroxyflavonol. It is functionally related to a kaempferol. It is a conjugate acid of a kaempferide(1-). Kaempferide is a natural product found in Ageratina altissima, Chromolaena odorata, and other organisms with data available. Isolated from roots of Alpinia officinarum (lesser galangal). Kaempferide is found in many foods, some of which are herbs and spices, cloves, sour cherry, and european plum. Kaempferide is found in cloves. Kaempferide is isolated from roots of Alpinia officinarum (lesser galangal). A monomethoxyflavone that is the 4-O-methyl derivative of kaempferol. Acquisition and generation of the data is financially supported in part by CREST/JST. Kaempferide is an O-methylated flavonol also found in kaempferol. Kaempferide has antiviral activity. Kaempferide is an orally active flavonol isolated from Hippophae rhamnoides L. Kaempferide has anticancer, anti-inflammatory, antioxidant, antidiabetic, antiobesity, antihypertensive, and neuroprotective activities. Kaempferide induces apoptosis. Kaempferide promotes osteogenesis through antioxidants and can be used in osteoporosis research[1][2][3][4][5][6]. Kaempferide is an O-methylated flavonol also found in kaempferol. Kaempferide has antiviral activity.

Astragalin

C21H20O11 (448.1006)

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].

Geniposidic acid

C16H22O10 (374.1213)

Geniposidic acid is found in beverages. Geniposidic acid is a constituent of Genipa americana (genipap) Constituent of Genipa americana (genipap). Geniposidic acid is found in beverages and fruits. Geniposidic acid has radiation protection and anti-cancer activity. Geniposidic acid has radiation protection and anti-cancer activity.

(+)-lariciresinol

C20H24O6 (360.1573)

(+)-Lariciresinol belongs to the class of organic compounds known as 7,9-epoxylignans. These are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at positons 2, 3 and 4, respectively. (+)-Lariciresinol has been detected in several different foods, such as parsnips, white mustards, narrowleaf cattails, turnips, and common sages. This could make (+)-Lariciresinol a potential biomarker for the consumption of these foods. Lariciresinol is also found in sesame seeds, Brassica vegetables, in the bark and wood of white fir (Abies alba). (+)-lariciresinol is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (+)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-lariciresinol can be found in a number of food items such as pili nut, lemon balm, root vegetables, and parsley, which makes (+)-lariciresinol a potential biomarker for the consumption of these food products.

Taxodione

C20H26O3 (314.1882)

Pachypodol

C18H16O7 (344.0896)

Pachypodol is a trimethoxyflavone that is quercetin in which the hydroxy groups at position 3, 7 and 3 are replaced by methoxy groups. It has been isolated from Combretum quadrangulare and Euodia elleryana. It has a role as a plant metabolite and an antiemetic. It is a dihydroxyflavone and a trimethoxyflavone. It is functionally related to a quercetin. Pachypodol is a natural product found in Larrea cuneifolia, Macaranga triloba, and other organisms with data available. A trimethoxyflavone that is quercetin in which the hydroxy groups at position 3, 7 and 3 are replaced by methoxy groups. It has been isolated from Combretum quadrangulare and Euodia elleryana. Pachypodol exerts antioxidant and cytoprotective effects in HepG2 cells[1].Pachypodol inhibits the growth of CaCo 2 colon cancer cell line in vitro(IC50 = 185.6 mM)[2]. Pachypodol exerts antioxidant and cytoprotective effects in HepG2 cells[1].Pachypodol inhibits the growth of CaCo 2 colon cancer cell line in vitro(IC50 = 185.6 mM)[2].

Methylprednisolone

C22H30O5 (374.2093)

H - Systemic hormonal preparations, excl. sex hormones and insulins > H02 - Corticosteroids for systemic use > H02A - Corticosteroids for systemic use, plain > H02AB - Glucocorticoids D - Dermatologicals > D10 - Anti-acne preparations > D10A - Anti-acne preparations for topical use > D10AA - Corticosteroids, combinations for treatment of acne D - Dermatologicals > D07 - Corticosteroids, dermatological preparations > D07A - Corticosteroids, plain > D07AA - Corticosteroids, weak (group i) D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006728 - Hormones > D005938 - Glucocorticoids C147908 - Hormone Therapy Agent > C548 - Therapeutic Hormone > C1636 - Therapeutic Steroid Hormone C308 - Immunotherapeutic Agent > C574 - Immunosuppressant > C211 - Therapeutic Corticosteroid COVID info from DrugBank, clinicaltrial, clinicaltrials, clinical trial, clinical trials D002491 - Central Nervous System Agents > D018696 - Neuroprotective Agents D018373 - Peripheral Nervous System Agents > D001337 - Autonomic Agents D005765 - Gastrointestinal Agents > D000932 - Antiemetics D000893 - Anti-Inflammatory Agents D020011 - Protective Agents Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 904; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8731; ORIGINAL_PRECURSOR_SCAN_NO 8728 CONFIDENCE standard compound; INTERNAL_ID 904; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8721; ORIGINAL_PRECURSOR_SCAN_NO 8719 CONFIDENCE standard compound; INTERNAL_ID 904; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8747; ORIGINAL_PRECURSOR_SCAN_NO 8745 CONFIDENCE standard compound; INTERNAL_ID 904; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8759; ORIGINAL_PRECURSOR_SCAN_NO 8757 CONFIDENCE standard compound; INTERNAL_ID 904; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8784; ORIGINAL_PRECURSOR_SCAN_NO 8783 CONFIDENCE standard compound; INTERNAL_ID 904; DATASET 20200303_ENTACT_RP_MIX500; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8757; ORIGINAL_PRECURSOR_SCAN_NO 8755 CONFIDENCE standard compound; INTERNAL_ID 2810 CONFIDENCE standard compound; INTERNAL_ID 1076 CONFIDENCE standard compound; EAWAG_UCHEM_ID 2621

Vitexin

C21H20O10 (432.1056)

Vitexin is an apigenin flavone glycoside, which is found in the passion flower, bamboo leaves and pearl millet It has a role as a platelet aggregation inhibitor, an EC 3.2.1.20 (alpha-glucosidase) inhibitor, an antineoplastic agent and a plant metabolite. It is a C-glycosyl compound and a trihydroxyflavone. It is functionally related to an apigenin. It is a conjugate acid of a vitexin-7-olate. Vitexin is a natural product found in Itea chinensis, Salacia chinensis, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of); Cytisus scoparius flowering top (part of); Fenugreek seed (part of) ... View More ... An apigenin flavone glycoside, which is found in the passion flower, bamboo leaves and pearl millet Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

Syringaldehyde

C9H10O4 (182.0579)

Syringaldehyde is a hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity. It has a role as a hypoglycemic agent and a plant metabolite. It is a hydroxybenzaldehyde and a dimethoxybenzene. Syringaldehyde is a natural product found in Ficus septica, Mikania laevigata, and other organisms with data available. Syringaldehyde is a metabolite found in or produced by Saccharomyces cerevisiae. A hydroxybenzaldehyde that is 4-hydroxybenzaldehyde substituted by methoxy groups at positions 3 and 5. Isolated from Pisonia aculeata and Panax japonicus var. major, it exhibits hypoglycemic activity. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1]. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

Corosolic acid

C30H48O4 (472.3552)

Colosolic acid is a natural product found in Rhododendron brachycarpum, Psidium, and other organisms with data available.

Naringenin

C15H12O5 (272.0685)

Naringenin is a trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4. It is a trihydroxyflavanone and a member of 4-hydroxyflavanones. 5,7-Dihydroxy-2-(4-hydroxyphenyl)chroman-4-one is a natural product found in Prunus mume, Helichrysum cephaloideum, and other organisms with data available. D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists A trihydroxyflavanone that is flavanone substituted by hydroxy groups at positions 5, 6 and 4. D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

Vitexin

C21H20O10 (432.1056)

Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

Verbasoside

C20H30O12 (462.1737)

Verbasoside is found in root vegetables. Verbasoside is isolated from Stachys sieboldii (Chinese artichoke). Isolated from Stachys sieboldii (Chinese artichoke). Verbasoside is found in root vegetables.

Isoacteoside

C29H36O15 (624.2054)

Isoacteoside is a polyphenol compound found in foods of plant origin (PMID: 20428313). A polyphenol compound found in foods of plant origin (PhenolExplorer) Isoacteoside is a natural product that can significantly inhibit the formation of glycation end products. Isoacteoside is a natural product that can significantly inhibit the formation of glycation end products.

Arjunolic acid

C30H48O5 (488.3502)

Arjunolic acid is found in fruits. Arjunolic acid is a constituent of Psidium guajava (guava) Constituent of Psidium guajava (guava). Arjunolic acid is found in fruits and guava.

Sugiol

C20H28O2 (300.2089)

Sugiol is found in fruits. Sugiol is a constituent of Juniperus communis (juniper). Constituent of Juniperus communis (juniper). Sugiol is found in fruits.

Carissic acid

C30H48O3 (456.3603)

Ustiloxin E is found in cereals and cereal products. Ustiloxin E is isolated from the false smut balls caused by Ustilaginoidea virens on rice. Constituent of Carissa carandas (karanda). Carissic acid is found in beverages and fruits.

Afzelin

C21H20O10 (432.1056)

5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one 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. 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one can be found in a number of food items such as endive, linden, peach, and ginkgo nuts, which makes 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]-4h-chromen-4-one a potential biomarker for the consumption of these food products. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

Corosolic acid

C30H48O4 (472.3552)

Corosolic acid, also known as corosolate, is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Corosolic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Corosolic acid can be found in guava, loquat, and olive, which makes corosolic acid a potential biomarker for the consumption of these food products. Corosolic acid is a pentacyclic triterpene acid found in Lagerstroemia speciosa. It is similar in structure to ursolic acid, differing only in the fact that it has a 2-alpha-hydroxy attachment . Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity. Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity.

Lariciresinol

C20H24O6 (360.1573)

(-)-lariciresinol is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (-)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-lariciresinol can be found in a number of food items such as cassava, acorn, celeriac, and banana, which makes (-)-lariciresinol a potential biomarker for the consumption of these food products.

Syringaldehyde

C9H10O4 (182.0579)

4-hydroxy-3,5-dimethoxybenzaldehyde, also known as sinapaldehyde or 2,6-dimethoxy-4-formylphenol, is a member of the class of compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. 4-hydroxy-3,5-dimethoxybenzaldehyde is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 4-hydroxy-3,5-dimethoxybenzaldehyde is a mild, sweet, and plastic tasting compound and can be found in a number of food items such as whisky, common grape, garden tomato (variety), and coriander, which makes 4-hydroxy-3,5-dimethoxybenzaldehyde a potential biomarker for the consumption of these food products. 4-hydroxy-3,5-dimethoxybenzaldehyde may be a unique S.cerevisiae (yeast) metabolite. Because it contains many functional groups, it can be classified in many ways - aromatic, aldehyde, phenol. It is a colorless solid (impure samples appear yellowish) that is soluble in alcohol and polar organic solvents. Its refractive index is 1.53 . Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1]. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

Verbascoside

C29H36O15 (624.2054)

Vitexin

C21H20O10 (432.1056)

Vitexin is a member of the class of compounds known as flavonoid 8-c-glycosides. Flavonoid 8-c-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to 8-position of a 2-phenylchromen-4-one flavonoid backbone. Vitexin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vitexin can be found in a number of food items such as flaxseed, prairie turnip, mung bean, and tree fern, which makes vitexin a potential biomarker for the consumption of these food products. Vitexin is an apigenin flavone glucoside, a chemical compound found in the passion flower, Vitex agnus-castus (chaste tree or chasteberry), in the Phyllostachys nigra bamboo leaves, in the pearl millet (Pennisetum millet), and in Hawthorn . Isovitexin is a flavonoid isolated from passion flower, Cannabis and, and the palm, possesses anti-inflammatory and anti-oxidant activities; Isovitexin acts like a JNK1/2 inhibitor and inhibits the activation of NF-κB. Isovitexin is a flavonoid isolated from passion flower, Cannabis and, and the palm, possesses anti-inflammatory and anti-oxidant activities; Isovitexin acts like a JNK1/2 inhibitor and inhibits the activation of NF-κB. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

(-)-Olivil

C20H24O7 (376.1522)

(-)-olivil is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (-)-olivil is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-olivil can be found in olive, which makes (-)-olivil a potential biomarker for the consumption of this food product.

L-Olivil

C20H24O7 (376.1522)

L-olivil is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively. L-olivil is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). L-olivil can be found in olive, which makes L-olivil a potential biomarker for the consumption of this food product.

Horminone

C20H28O4 (332.1987)

Horminone is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Horminone can be found in common sage, which makes horminone a potential biomarker for the consumption of this food product.

Ursolic acid (2-alpha-hydroxy-)

C30H48O4 (472.3552)

Geniposidic_acid

C16H22O10 (374.1213)

Geniposidic acid is a terpene glycoside. Geniposidic acid is a natural product found in Avicennia officinalis, Gardenia jasminoides, and other organisms with data available. Geniposidic acid has radiation protection and anti-cancer activity. Geniposidic acid has radiation protection and anti-cancer activity.

Corosolic_acid

C30H48O4 (472.3552)

Corosolic acid is a triterpenoid. It has a role as a metabolite. Corosolic acid is a natural product found in Ternstroemia gymnanthera, Cunila lythrifolia, and other organisms with data available. See also: Lagerstroemia speciosa leaf (part of). A natural product found particularly in Rhododendron species and Eriobotrya japonica. Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity. Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity.

Cistanoside F

C21H28O13 (488.153)

Cistanoside F is a natural product found in Premna odorata, Cistanche deserticola, and other organisms with data available.

Verbascoside

C29H36O15 (624.2054)

Acteoside is a glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid. It has a role as a neuroprotective agent, an antileishmanial agent, an anti-inflammatory agent, a plant metabolite and an antibacterial agent. It is a cinnamate ester, a disaccharide derivative, a member of catechols, a polyphenol and a glycoside. It is functionally related to a hydroxytyrosol and a trans-caffeic acid. Acteoside is under investigation in clinical trial NCT02662283 (Validity and Security of Reh-acteoside Therapy for Patients of IgA Nephropathy). Acteoside is a natural product found in Orobanche amethystea, Barleria lupulina, and other organisms with data available. See also: Harpagophytum zeyheri root (part of). A glycoside that is the alpha-L-rhamnosyl-(1->3)-beta-D-glucoside of hydroxytyrosol in which the hydroxy group at position 4 of the glucopyranosyl moiety has undergone esterification by formal condensation with trans-caffeic acid. D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents D064449 - Sequestering Agents > D002614 - Chelating Agents D020011 - Protective Agents > D000975 - Antioxidants D000890 - Anti-Infective Agents D000970 - Antineoplastic Agents Verbascoside is isolated from Acanthus mollis, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 μM, and has antitumor, anti-inflammatory and antineuropathic pain activity. Verbascoside is isolated from Acanthus mollis, acts as an ATP-competitive inhibitor of PKC, with an IC50 of 25 μM, and has antitumor, anti-inflammatory and antineuropathic pain activity.

Astragalin

C21H20O11 (448.1006)

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].

Corosolic acid

C30H48O4 (472.3552)

Annotation level-1 Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity. Corosolic acid (Colosolic acid) isolated from the fruit of Cratoegus pinnatifida var. psilosa, was reported to have anticancer activity.

Horminone

C20H28O4 (332.1987)

Horminone is an abietane diterpenoid that is abieta-8,12-diene substituted by hydroxy groups at positions 7 and 12 and oxo groups at positions 11 and 14 (the 7alpha stereoisomer). It has a role as an antibacterial agent, an antineoplastic agent and a metabolite. It is an abietane diterpenoid, a secondary alcohol, a hydroxyquinone and a member of p-quinones. Horminone is a natural product found in Salvia tomentosa, Salvia virgata, and other organisms with data available. An abietane diterpenoid that is abieta-8,12-diene substituted by hydroxy groups at positions 7 and 12 and oxo groups at positions 11 and 14 (the 7alpha stereoisomer) .

Ursolic Acid

C30H48O3 (456.3603)

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.

Chrysosplenol D

C18H16O8 (360.0845)

Chrysosplenol D is a methoxy flavonoid that induces ERK1/2-mediated apoptosis in triple negative human breast cancer cells. Chrysosplenol D also exhibits anti-inflammatory and moderate antitrypanosomal activities[1][2][3][4]. Chrysosplenol D is a methoxy flavonoid that induces ERK1/2-mediated apoptosis in triple negative human breast cancer cells. Chrysosplenol D also exhibits anti-inflammatory and moderate antitrypanosomal activities[1][2][3][4].

coniferyl aldehyde

C10H10O3 (178.063)

Annotation level-1 Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1]. Coniferaldehyde (Ferulaldehyde) is an effective inducer of heme oxygenase-1 (HO-1). Coniferaldehyde exerts anti-inflammatory properties in response to LPS. Coniferaldehyde inhibits LPS-induced apoptosis through the PKCα/β II/Nrf-2/HO-1 dependent pathway in RAW264.7 macrophage cells[1].

Afzelin

C21H20O10 (432.1056)

Afzelin is a glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. It has a role as a plant metabolite, an antibacterial agent and an anti-inflammatory agent. It is a glycosyloxyflavone, a trihydroxyflavone and a monosaccharide derivative. It is functionally related to a kaempferol. It is a conjugate acid of an afzelin(1-). Afzelin is a natural product found in Premna odorata, Vicia tenuifolia, and other organisms with data available. A glycosyloxyflavone that is kaempferol attached to an alpha-L-rhamnosyl residue at position 3 via a glycosidic linkage. Acquisition and generation of the data is financially supported in part by CREST/JST. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1]. Afzelin (Kaempferol-3-O-rhamnoside)It is a flavonol glycoside that has anti-inflammatory, anti-oxidative stress response, anti-apoptotic, and anti-cardiac cytotoxic effects. AfzelinIt can reduce mitochondrial damage, enhance mitochondrial biosynthesis, and reduce mitochondria-related proteins. Parkinand PTENinduced putative kinase 1 (putative kinase 1)s level. AfzelinCan be improved D-galactosamine(GalN)/LPSSurvival rate of mice treated with doxorubicin prophylaxis (HY-15142A)Induced cardiotoxicity and scopolamine (HY-N0296)-induced neurological injury. AfzelinAlso inhibits asthma and allergies caused by ovalbumin[1][2][3][4]. Afzelin (Kaempferol-3-O-rhamnoside) is is a flavonol glycoside found in Houttuynia cordata Thunberg and is widely used in the preparation of antibacterial and antipyretic agents, detoxicants and for the treatment of inflammation. Afzelin attenuates the mitochondrial damage, enhances mitochondrial biogenesis and decreases the level of mitophagy-related proteins, parkin and PTEN-induced putative kinase 1. Afzelin improves the survival rate and reduces the serum levels of alanine aminotransferase and pro-inflammatory cytokines in D-galactosamine (GalN)/LPS -treated mice[1].

Vitexin

C21H20O10 (432.1056)

Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2]. Vitexin is a c-glycosylated flavone, and is found in various medicinal plants species such as Trigonella foenum-graecum Linn. Vitexin has a wide range of pharmacological effects, including anti-oxidant, anti-cancer, anti-inflammatory, anti-hyperalgesic, and neuroprotective effects[1][2].

Apigenin

C15H10O5 (270.0528)

Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.061 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.062 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.058 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.059 Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

Luteolin

C15H10O6 (286.0477)

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].

Eriodictyol

C15H12O6 (288.0634)

Constituent of the leaves and branches of Phyllanthus emblica (emblic). Eriodictyol 7-(6-coumaroylglucoside) is found in fruits. Annotation level-1 Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM. Eriodictyol is a flavonoid isolated from the Chinese herb, with antioxidant and anti-inflammatory activity. Eriodictyol induces Nrf2 signaling pathway. Eriodictyol is also a potent influenza RNA-dependent RNA polymerase inhibitor with an IC50 of 18 nM.

Naringenin

C15H12O5 (272.0685)

Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.904 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.906 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.901 CONFIDENCE standard compound; ML_ID 50 (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

Quercitrin

C21H20O11 (448.1006)

Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2]. Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2]. Quercitrin (Quercetin 3-rhamnoside) is a bioflavonoid compound with potential anti-inflammation, antioxidative and neuroprotective effect. Quercitrin induces apoptosis of colon cancer cells. Quercitrin can be used for the research of cardiovascular and neurological disease research[1][2].

Quercetin

C15H10O7 (302.0427)

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].

Syringaldehyde

C9H10O4 (182.0579)

Acquisition and generation of the data is financially supported in part by CREST/JST. IPB_RECORD: 303; CONFIDENCE confident structure Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1]. Syringaldehyde is a polyphenolic compound belonging to the group of flavonoids and is found in different plant species like Manihot esculenta and Magnolia officinalis[1]. Syringaldehyde moderately inhibits COX-2 activity with an IC50 of 3.5 μg/mL[2]. Anti-hyperglycemic and anti-inflammatory activities[1].

lupeol

C30H50O (426.3861)

D000893 - Anti-Inflammatory Agents Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1]. Lupeol (Clerodol; Monogynol B; Fagarasterol) is an active pentacyclic?triterpenoid, has anti-oxidant, anti-mutagenic, anti-tumor and anti-inflammatory activity. Lupeol is a potent?androgen receptor (AR)?inhibitor and can be used for cancer research, especially prostate cancer of androgen-dependent phenotype (ADPC) and castration resistant phenotype (CRPC)[1].

6-hydroxy-5,6-dehydrosugiol

C20H26O3 (314.1882)

2-(2-Formyl-1,3,3-trimethylcyclohexyl)-4-hydroxy-5-isopropylbenzaldehyde

C20H28O3 (316.2038)

Aucubin

C15H22O9 (346.1264)

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].

Arucadiol

C19H22O3 (298.1569)

olivil

C20H24O7 (376.1522)

Syringaresinol

C22H26O8 (418.1628)

(+)-syringaresinol is the (7alpha,7alpha,8alpha,8alpha)-stereoisomer of syringaresinol. It has a role as an antineoplastic agent. It is an enantiomer of a (-)-syringaresinol. (+)-Syringaresinol is a natural product found in Dracaena draco, Diospyros eriantha, and other organisms with data available. See also: Acai fruit pulp (part of). The (7alpha,7alpha,8alpha,8alpha)-stereoisomer of syringaresinol.

Lirioresinol b

C22H26O8 (418.1628)

(-)-syringaresinol is the (7beta,7beta,8beta,8beta)-stereoisomer of syringaresinol. It is an enantiomer of a (+)-syringaresinol. (-)-Syringaresinol is a natural product found in Pittosporum illicioides, Cinnamomum kotoense, and other organisms with data available. The (7beta,7beta,8beta,8beta)-stereoisomer of syringaresinol. (-)-Syringaresinol, found in stems of Annona Montana, possesses anti-cancer activity[1]. (-)-Syringaresinol, found in stems of Annona Montana, possesses anti-cancer activity[1].

Arjunolicacid

C30H48O5 (488.3502)

Arjunolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities. It has a role as a metabolite, an antibacterial agent, an antifungal agent and an antioxidant. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It derives from a hydride of an oleanane. Arjunolic acid is a natural product found in Musanga cecropioides, Akebia quinata, and other organisms with data available. A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by hydroxy groups at positions 2, 3 and 23 (the 2alpha,3beta stereoisomer). Isolated from Symplocos lancifolia and Juglans sinensis, it exhibits antioxidant and antimicrobial activities.

Lariciresinol

C20H24O6 (360.1573)

(+)-lariciresinol is a lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). It has a role as an antifungal agent and a plant metabolite. It is a member of oxolanes, a member of phenols, a lignan, a primary alcohol and an aromatic ether. It is an enantiomer of a (-)-lariciresinol. Lariciresinol is a natural product found in Magnolia kachirachirai, Euterpe oleracea, and other organisms with data available. See also: Acai fruit pulp (part of). A lignan that is tetrahydrofuran substituted at positions 2, 3 and 4 by 4-hydroxy-3-methoxyphenyl, hydroxymethyl and 4-hydroxy-3-methoxybenzyl groups respectively (the 2S,3R,4R-diastereomer). (-)-lariciresinol is a member of the class of compounds known as 7,9-epoxylignans. 7,9-epoxylignans are lignans that contain the 7,9-epoxylignan skeleton, which consists of a tetrahydrofuran that carries a phenyl group, a methyl group, and a benzyl group at the 2-, 3-, 4-position, respectively (-)-lariciresinol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (-)-lariciresinol can be found in a number of food items such as ostrich fern, pepper (c. frutescens), ohelo berry, and guava, which makes (-)-lariciresinol a potential biomarker for the consumption of these food products. Annotation level-1 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.823 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.820 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.818 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.812

DGMG 18:3

C33H56O14 (676.367)

Gingerglycolipid A is a galactosylglycerol derivative. Gingerglycolipid A is a natural product found in Guapira graciliflora, Sonchus mauritanicus, and other organisms with data available. Annotation level-3

Geniposidic acid

C16H22O10 (374.1213)

Geniposidic acid has radiation protection and anti-cancer activity. Geniposidic acid has radiation protection and anti-cancer activity.

Kaempferide

C16H12O6 (300.0634)

relative retention time with respect to 9-anthracene Carboxylic Acid is 1.191 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.194 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.190 Kaempferide is an O-methylated flavonol also found in kaempferol. Kaempferide has antiviral activity. Kaempferide is an orally active flavonol isolated from Hippophae rhamnoides L. Kaempferide has anticancer, anti-inflammatory, antioxidant, antidiabetic, antiobesity, antihypertensive, and neuroprotective activities. Kaempferide induces apoptosis. Kaempferide promotes osteogenesis through antioxidants and can be used in osteoporosis research[1][2][3][4][5][6]. Kaempferide is an O-methylated flavonol also found in kaempferol. Kaempferide has antiviral activity.

4-hydroxybenzoate

C7H6O3 (138.0317)

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 (168.0423)

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].

5-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-3,7-dimethoxychromen-4-one

C19H18O8 (374.1002)

p-Hydroxybenzoic acid

C7H6O3 (138.0317)

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 (442.3811)

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.

α-Linolenic acid

C18H30O2 (278.2246)

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].

syringaresinol

C22H26O8 (418.1628)

FA 18:3

C18H30O2 (278.2246)

CONFIDENCE standard compound; INTERNAL_ID 143 COVID info from WikiPathways D - Dermatologicals Same as: D07213 Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS 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].

coniferaldehyde

C10H10O3 (178.063)

CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 13

5-hydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-3,7-dimethoxy-4H-chromen-4-one

C19H18O8 (374.1002)

4-Hydroxy-3,5-dimethoxybenzaldehyde

C9H10O4 (182.0579)

Asahina

C15H12O5 (272.0685)

D006730 - Hormones, Hormone Substitutes, and Hormone Antagonists > D006727 - Hormone Antagonists > D004965 - Estrogen Antagonists D005765 - Gastrointestinal Agents > D000897 - Anti-Ulcer Agents (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. (±)-Naringenin is a naturally-occurring flavonoid. (±)-Naringenin displays vasorelaxant effect on endothelium-denuded vessels via the activation of BKCa channels in myocytes[1]. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity. Naringenin is the predominant flavanone in Citrus reticulata Blanco; displays strong anti-inflammatory and antioxidant activities. Naringenin has anti-dengue virus (DENV) activity.

Anisylacetone

C11H14O2 (178.0994)

Anisylacetone (p-Methoxybenzylacetone) is a male fruit fly attractant[1]. Anisylacetone (p-Methoxybenzylacetone) is a male fruit fly attractant[1].

Arjunolic acid

C30H48O5 (488.3502)

Carissic acid

C30H48O3 (456.3603)

Verbasoside

C20H30O12 (462.1737)

Gingerglycolipid A

C33H56O14 (676.367)

3-Linoleoyl-sn-glycerol

C21H38O4 (354.277)

A 3-acyl-sn-glycerol that is the R-enantiomer of 1-monolinolein.

Versulin

C15H10O5 (270.0528)

Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM. Apigenin (4',5,7-Trihydroxyflavone) is a competitive CYP2C9 inhibitor with a Ki of 2 μM.

Vanillate

C8H8O4 (168.0423)

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].

Chrysosplenetin

C19H18O8 (374.1002)

Chrysosplenetin is a tetramethoxyflavone that is the 3,6,7,3-tetramethyl ether derivative of quercetagetin. It has a role as an antiviral agent and a plant metabolite. It is a tetramethoxyflavone and a dihydroxyflavone. It is functionally related to a quercetagetin. Chrysosplenetin is a natural product found in Haplophyllum myrtifolium, Cleome amblyocarpa, and other organisms with data available. A tetramethoxyflavone that is the 3,6,7,3-tetramethyl ether derivative of quercetagetin. Chrysosplenetin is one of the polymethoxylated flavonoids in Artemisia annua L. (Compositae) and other several Chinese herbs. Chrysosplenetin inhibits P-gp activity and reverses the up-regulated P-gp and MDR1 levels induced by artemisinin (ART). Chrysosplenetin significantly augments the rat plasma level and anti-malarial efficacy of ART, partially due to the uncompetitive inhibition effect of Chrysosplenetin on rat CYP3A[1]. Chrysosplenetin is one of the polymethoxylated flavonoids in Artemisia annua L. (Compositae) and other several Chinese herbs. Chrysosplenetin inhibits P-gp activity and reverses the up-regulated P-gp and MDR1 levels induced by artemisinin (ART). Chrysosplenetin significantly augments the rat plasma level and anti-malarial efficacy of ART, partially due to the uncompetitive inhibition effect of Chrysosplenetin on rat CYP3A[1].

Royleanone

C20H28O3 (316.2038)

Royleanone is a diterpenoid. Royleanone is a natural product found in Salvia virgata, Salvia deserti, and other organisms with data available.

3-[3,4-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-3,4-dihydro-2h-1-benzopyran-6-yl]prop-2-enal

C20H20O7 (372.1209)

7,7,14-trimethyl-16-oxatetracyclo[9.7.0.0³,⁸.0¹³,¹⁷]octadeca-1(18),11,13(17)-triene-3,18-diol

C20H28O3 (316.2038)

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

C42H60O20 (884.3678)

(2s,3r,4r,5s,6s)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5-hydroxy-2-{[(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]oxy}-6-methyloxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C39H44O20 (832.2426)

7-isopropyl-3,3,4-trimethylnaphtho[2,3-b]furan-2,5,6-trione

C18H18O4 (298.1205)

(2s,6r)-8-[(1s,4as,6r,7r,7as)-6-hydroxy-7-methyl-1-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carbonyloxy]-2,6-dimethyloctyl (1s,4as,6r,7as)-6-hydroxy-7-methylidene-1-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C42H64O20 (888.3991)

(10ar)-5,6-dihydroxy-7-isopropyl-1,1,10a-trimethyl-2h-phenanthren-3-one

C20H24O3 (312.1725)

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

C25H32O13 (540.1843)

[(1s,2s,4s,5s,6r,10s)-5-hydroxy-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-2-yl]methyl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C24H28O13 (524.153)

(2s,7s)-8-[(1s,4as,6s,7as)-6-hydroxy-7-methylidene-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbonyloxy]-2,7-dimethyloctyl (1s,4as,6s,7as)-6-hydroxy-7-methylidene-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C42H62O20 (886.3834)

(2s,6r)-8-[(1s,4as,6s,7as)-6-hydroxy-7-methylidene-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbonyloxy]-2,6-dimethyloctyl (1s,4as,6s,7as)-6-hydroxy-7-methylidene-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C42H62O20 (886.3834)

[(1s,4ar,5s,6r,7s,7as)-6-chloro-5,7-dihydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]methyl (2e)-3-(4-methoxyphenyl)prop-2-enoate

C25H31ClO12 (558.1504)

3-isopropyl-5,5-dimethyl-7,8-dihydro-6h-anthracene-1,2-dione

C19H22O2 (282.162)

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

C42H66O20 (890.4147)

[(1s,2s,4s,5s,6r,10s)-5-hydroxy-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-2-yl]methyl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

C24H28O12 (508.1581)

8-(7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbonyloxy)-2,6-dimethyloctyl 6-hydroxy-7-methylidene-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C42H64O20 (888.3991)

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

C42H66O20 (890.4147)

7-isopropyl-1,4a-dimethyl-hexahydro-2h-naphthalene-1,8a-diol

C15H28O2 (240.2089)

1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulene-4,7-diol

C15H26O2 (238.1933)

3,5-dihydroxy-2-{[2-(hydroxymethyl)-10-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,9-dioxatricyclo[4.4.0.0²,⁴]dec-7-en-5-yl]oxy}-6-methyloxan-4-yl 3-(3-hydroxy-4-methoxyphenyl)prop-2-enoate

C31H40O17 (684.2265)

(3r,8r)-14,15-dihydroxy-13-isopropyl-7,7-dimethyltricyclo[9.4.0.0³,⁸]pentadeca-1(11),9,12,14-tetraen-4-one

C20H26O3 (314.1882)

6-hydroxy-7-isopropyl-1,4a-dimethyl-2,3,4,9,10,10a-hexahydrophenanthrene-1-carboxylic acid

C20H28O3 (316.2038)

(2s,6r)-8-[(1s,4as,6r,7as)-6-hydroxy-7-methylidene-1-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbonyloxy]-2,6-dimethyloctyl (1s,4as,6r,7as)-6-hydroxy-7-methylidene-1-{[(2r,3s,4r,5r,6s)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C42H62O20 (886.3834)

(4ar)-5-hydroxy-7-isopropyl-1,1,4a-trimethyl-2,4-dihydrophenanthrene-3,6-dione

C20H24O3 (312.1725)

(2r,3r,4r,5r,6r)-4-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5-hydroxy-2-{[(1s,2s,4s,5s,6s,10s)-2-(hydroxymethyl)-10-{[(2s,3s,4r,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]oxy}-6-methyloxan-3-yl (2e)-3-(4-hydroxyphenyl)prop-2-enoate

C39H44O19 (816.2477)

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

C19H32O8 (388.2097)

(2r,4as)-2,5-dihydroxy-7-isopropyl-1,1,4a-trimethyl-2,4-dihydrophenanthrene-3,6-dione

C20H24O4 (328.1675)

8-(6-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7h,7ah-cyclopenta[c]pyran-4-carbonyloxy)-2,6-dimethyloctyl 6-hydroxy-7-methylidene-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carboxylate

C42H64O20 (888.3991)

(3r)-15-hydroxy-13-isopropyl-3,7,7-trimethyl-4-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),8,10,12-tetraene-5,14-dione

C20H24O4 (328.1675)

(2r,3r,4r,5r,6r)-5-hydroxy-6-[2-(3-hydroxy-4-methoxyphenyl)ethoxy]-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C31H40O15 (652.2367)

(1ar,4r,4ar,7s,7as,7br)-1,1,4,7-tetramethyl-octahydrocyclopropa[e]azulene-4,7-diol

C15H26O2 (238.1933)

(2s,6r)-8-[(1s,4as,6s,7as)-6-hydroxy-7-methylidene-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-4-carbonyloxy]-2,6-dimethyloctyl (1s,4as,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-4-carboxylate

C42H64O20 (888.3991)

7-hydroxy-3-isopropyl-5,5,9-trimethylanthracene-1,2,6-trione

C20H20O4 (324.1362)

(2s,3r,4r,5s,6s)-5-hydroxy-2-{[(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]oxy}-4-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}-6-methyloxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C39H44O19 (816.2477)

(3s,8s,14r)-7,7,14-trimethyl-16-oxatetracyclo[9.7.0.0³,⁸.0¹³,¹⁷]octadeca-1(18),11,13(17)-triene-3,18-diol

C20H28O3 (316.2038)

3,5-dihydroxy-2-(3-hydroxy-4,5-dimethoxyphenyl)-6,7-dimethoxychromen-4-one

C19H18O9 (390.0951)

(2s,3r,4r,5s,6s)-3,5-dihydroxy-2-{[(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]oxy}-6-methyloxan-4-yl (2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoate

C31H40O17 (684.2265)

methyl 5-[(1r,2s,3r,4r,4ar,8ar)-3-hydroxy-1,2,4a,5-tetramethyl-4-{[(2z)-3-phenylprop-2-enoyl]oxy}-2,3,4,7,8,8a-hexahydronaphthalen-1-yl]-3-methylidene-4-oxopentanoate

C30H38O6 (494.2668)

[(1s,4ar,5s,6r,7s,7as)-6-chloro-5,7-dihydroxy-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-7-yl]methyl (2z)-3-(4-hydroxyphenyl)prop-2-enoate

C24H29ClO12 (544.1347)

2-{[4-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C19H32O8 (388.2097)

7-ethenyl-1,1,4a,7-tetramethyl-decahydrophenanthrene-2,4,8a-triol

C20H34O3 (322.2508)

3,10-dihydroxy-2-isopropyl-4b,8,8-trimethyl-5,6,7,8a,9,10-hexahydrophenanthrene-1,4-dione

C20H28O4 (332.1987)

3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-hexadecahydrocyclopenta[a]chrysen-9-ol

C30H50O2 (442.3811)

(11s,17s,18s)-24-hydroxy-17-(4-hydroxyphenyl)-16-oxa-1,6,10,23-tetraazatetracyclo[9.8.6.2¹²,¹⁵.0¹⁴,¹⁸]heptacosa-12(27),13,15(26),23-tetraen-19-one

C28H36N4O4 (492.2736)

2,3,5-trihydroxy-6-methyloxan-4-yl 3-(4-methoxyphenyl)prop-2-enoate

C16H20O7 (324.1209)