NCBI Taxonomy: 13509

Quercitrin

C21H20O11 (448.100557)

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].

Epicatechin

C15H14O6 (290.0790344)

Epicatechin is an antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. Catechin is a tannin peculiar to green and white tea because the black tea oxidation process reduces catechins in black tea. Catechin is a powerful, water soluble polyphenol and antioxidant that is easily oxidized. Several thousand types are available in the plant world. As many as two thousand are known to have a flavon structure and are called flavonoids. Catechin is one of them. Green tea is manufactured from fresh, unfermented tea leaves; the oxidation of catechins is minimal, and hence they are able to serve as antioxidants. Researchers believe that catechin is effective because it easily sticks to proteins, blocking bacteria from adhering to cell walls and disrupting their ability to destroy them. Viruses have hooks on their surfaces and can attach to cell walls. The catechin in green tea prevents viruses from adhering and causing harm. Catechin reacts with toxins created by harmful bacteria (many of which belong to the protein family) and harmful metals such as lead, mercury, chrome, and cadmium. From its NMR espectra, there is a doubt on 2 and 3 atoms configuration. It seems to be that they are in trans position. Epicatechin, also known as (+)-cyanidanol-3 or 2,3-cis-epicatechin, is a member of the class of compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-tiol. Thus, epicatechin is considered to be a flavonoid lipid molecule. Epicatechin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Epicatechin can be found in cashew nut, which makes epicatechin a potential biomarker for the consumption of this food product. Epicatechin can be found primarily in blood, feces, and urine, as well as throughout most human tissues. Epicatechin is a flavan-3-ol, a type of natural phenol and antioxidant. It is a plant secondary metabolite. It belongs to the group of flavan-3-ols (or simply flavanols), part of the chemical family of flavonoids . (-)-epicatechin is a catechin with (2R,3R)-configuration. It has a role as an antioxidant. It is a polyphenol and a catechin. It is an enantiomer of a (+)-epicatechin. Epicatechin has been used in trials studying the treatment of Pre-diabetes. (-)-Epicatechin is a natural product found in Visnea mocanera, Litsea rotundifolia, and other organisms with data available. An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms. See also: Crofelemer (monomer of); Bilberry (part of); Cats Claw (part of) ... View More ... A catechin with (2R,3R)-configuration. [Raw Data] CB030_(-)-Epicatechin_pos_20eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_pos_50eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_pos_40eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_pos_10eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_pos_30eV_CB000016.txt [Raw Data] CB030_(-)-Epicatechin_neg_50eV_000009.txt [Raw Data] CB030_(-)-Epicatechin_neg_30eV_000009.txt [Raw Data] CB030_(-)-Epicatechin_neg_10eV_000009.txt [Raw Data] CB030_(-)-Epicatechin_neg_40eV_000009.txt [Raw Data] CB030_(-)-Epicatechin_neg_20eV_000009.txt Epicatechin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=490-46-0 (retrieved 2024-07-09) (CAS RN: 490-46-0). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB. (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB. (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB. (-)-Epicatechin inhibits cyclooxygenase-1 (COX-1) with an IC50 of 3.2 μM. (-)-Epicatechin inhibits the IL-1β-induced expression of iNOS by blocking the nuclear localization of the p65 subunit of NF-κB.

Vanillic acid

C8H8O4 (168.0422568)

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

Protocatechuic acid

C7H6O4 (154.0266076)

Protocatechuic acid, also known as protocatechuate or 3,4-dihydroxybenzoate, 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. The enzyme protocatechuate 3,4-dioxygenase uses 3,4-dihydroxybenzoate and O2 to produce 3-carboxy-cis,cis-muconate. Protocatechuic acid is a drug. In the analogous hardening of the cockroach ootheca, the phenolic substance concerned is protocatechuic acid. Protocatechuic acid is a mild, balsamic, and phenolic tasting compound. Outside of the human body, protocatechuic acid is found, on average, in the highest concentration in a few different foods, such as garden onions, cocoa powders, and star anises and in a lower concentration in lentils, liquors, and red raspberries. Protocatechuic acid has also been detected, but not quantified in several different foods, such as cloud ear fungus, american pokeweeds, common mushrooms, fruits, and feijoa. This could make protocatechuic acid a potential biomarker for the consumption of these foods. It is also found in Allium cepa (17,540 ppm). It is a major metabolite of antioxidant polyphenols found in green tea. Similarly, PCA was reported to increase proliferation and inhibit apoptosis of neural stem cells. In vitro testing documented antioxidant and anti-inflammatory activity of PCA, while liver protection in vivo was measured by chemical markers and histological assessment. 3,4-dihydroxybenzoic acid, also known as protocatechuic acid or 4-carboxy-1,2-dihydroxybenzene, belongs to hydroxybenzoic acid derivatives class of compounds. Those are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. 3,4-dihydroxybenzoic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxybenzoic acid can be synthesized from benzoic acid. 3,4-dihydroxybenzoic acid is also a parent compound for other transformation products, including but not limited to, methyl 3,4-dihydroxybenzoate, ethyl 3,4-dihydroxybenzoate, and 1-(3,4-dihydroxybenzoyl)-beta-D-glucopyranose. 3,4-dihydroxybenzoic acid is a mild, balsamic, and phenolic tasting compound and can be found in a number of food items such as white mustard, grape wine, abalone, and asian pear, which makes 3,4-dihydroxybenzoic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxybenzoic acid can be found primarily in blood, feces, and urine, as well as in human fibroblasts and testes tissues. 3,4-dihydroxybenzoic acid exists in all eukaryotes, ranging from yeast to humans. Protocatechuic acid (PCA) is a dihydroxybenzoic acid, a type of phenolic acid. It is a major metabolite of antioxidant polyphenols found in green tea. It has mixed effects on normal and cancer cells in in vitro and in vivo studies . 3,4-dihydroxybenzoic acid is a dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. It has a role as a human xenobiotic metabolite, a plant metabolite, an antineoplastic agent, an EC 1.1.1.25 (shikimate dehydrogenase) inhibitor and an EC 1.14.11.2 (procollagen-proline dioxygenase) inhibitor. It is a member of catechols and a dihydroxybenzoic acid. It is functionally related to a benzoic acid. It is a conjugate acid of a 3,4-dihydroxybenzoate. 3,4-Dihydroxybenzoic acid is a natural product found in Visnea mocanera, Amomum subulatum, and other organisms with data available. Protocatechuic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Vaccinium myrtillus Leaf (part of); Menyanthes trifoliata leaf (part of) ... View More ... A dihydroxybenzoic acid in which the hydroxy groups are located at positions 3 and 4. Protocatechuic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=99-50-3 (retrieved 2024-06-29) (CAS RN: 99-50-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

Isoquercitrin

C21H20O12 (464.09547200000003)

Quercetin 3-O-beta-D-glucopyranoside is a quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells It has a role as an antineoplastic agent, a plant metabolite, a bone density conservation agent, an osteogenesis regulator, an antioxidant, a histamine antagonist, an antipruritic drug and a geroprotector. It is a quercetin O-glucoside, a tetrahydroxyflavone, a beta-D-glucoside and a monosaccharide derivative. It is functionally related to a beta-D-glucose. It is a conjugate acid of a quercetin 3-O-beta-D-glucopyranoside(1-). Isoquercetin has been used in trials studying the treatment of Kidney Cancer, Renal cell carcinoma, Advanced Renal Cell Carcinoma, Thromboembolism of Vein in Pancreatic Cancer, and Thromboembolism of Vein VTE in Colorectal Cancer, among others. Isoquercitrin is a natural product found in Ficus auriculata, Lotus ucrainicus, and other organisms with data available. Isoquercetin is an orally bioavailable, glucoside derivative of the flavonoid quercetin and protein disulfide isomerase (PDI) inhibitor, with antioxidant and potential antithrombotic activity. As an antioxidant, isoquercetin scavenges free radicals and inhibits oxidative damage to cells. As a PDI inhibitor, this agent blocks PDI-mediated platelet activation, and fibrin generation, which prevents thrombus formation after vascular injury. In addition, isoquercetin is an alpha-glucosidase inhibitor. PDI, an oxidoreductase secreted by activated endothelial cells and platelets, plays a key role in the initiation of the coagulation cascade. Cancer, in addition to other thrombotic disorders, increases the risk of thrombus formation. Isoquercitrin is found in alcoholic beverages. Isoquercitrin occurs widely in plants. Isoquercitrin is present in red wine.Isoquercitin can be isolated from mangoes and from Rheum nobile, the Noble rhubarb or Sikkim rhubarb, a giant herbaceous plant native to the Himalaya. Quercetin glycosides are also present in tea. (Wikipedia A quercetin O-glucoside that is quercetin with a beta-D-glucosyl residue attached at position 3. Isolated from Lepisorus contortus, it exhibits antineoplastic activityand has been found to decrease the rate of polymerization and sickling of red blood cells [Raw Data] CB053_Isoquercitrin_pos_10eV_CB000025.txt [Raw Data] CB053_Isoquercitrin_pos_30eV_CB000025.txt [Raw Data] CB053_Isoquercitrin_pos_50eV_CB000025.txt [Raw Data] CB053_Isoquercitrin_pos_40eV_CB000025.txt [Raw Data] CB053_Isoquercitrin_pos_20eV_CB000025.txt [Raw Data] CB053_Isoquercitrin_neg_40eV_000017.txt [Raw Data] CB053_Isoquercitrin_neg_20eV_000017.txt [Raw Data] CB053_Isoquercitrin_neg_50eV_000017.txt [Raw Data] CB053_Isoquercitrin_neg_30eV_000017.txt [Raw Data] CB053_Isoquercitrin_neg_10eV_000017.txt Quercetin 3-glucoside. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=482-35-9 (retrieved 2024-07-09) (CAS RN: 482-35-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Isoquercetin (Quercetin 3-glucoside) is a naturally occurring polyphenol that has antioxidant, anti-proliferative, and anti-inflammatory properties. Isoquercetin alleviates ethanol-induced hepatotoxicity, oxidative stress, and inflammatory responses via the Nrf2/ARE antioxidant signaling pathway[1]. Isoquercetin regulates the expression of nitric oxide synthase 2 (NO2) via modulating the nuclear factor-κB (NF-κB) transcription regulation system. Isoquercetin has high bioavailability and low toxicity, is a promising candidate agent to prevent birth defects in diabetic pregnancies[2]. Isoquercetin (Quercetin 3-glucoside) is a naturally occurring polyphenol that has antioxidant, anti-proliferative, and anti-inflammatory properties. Isoquercetin alleviates ethanol-induced hepatotoxicity, oxidative stress, and inflammatory responses via the Nrf2/ARE antioxidant signaling pathway[1]. Isoquercetin regulates the expression of nitric oxide synthase 2 (NO2) via modulating the nuclear factor-κB (NF-κB) transcription regulation system. Isoquercetin has high bioavailability and low toxicity, is a promising candidate agent to prevent birth defects in diabetic pregnancies[2]. Isoquercitrin (Isoquercitroside) is an effective antioxidant and an eosinophilic inflammation suppressor. Isoquercitrin (Isoquercitroside) is an effective antioxidant and an eosinophilic inflammation suppressor.

Ursolic acid

C30H48O3 (456.36032579999994)

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

Rutin

C27H30O16 (610.153378)

Rutin is a flavonoid known to have a variety of biological activities including antiallergic, anti-inflammatory, antiproliferative, and anticarcinogenic properties. A large number of flavonoids, mostly O-glycosides, are polyphenolic compounds of natural origin that are present in most fruits and vegetables. The average intake of the compounds by humans on a normal diet is more than 1 g per day. Although flavonoids are devoid of classical nutritional value, they are increasingly viewed as beneficial dietary components that act as potential protectors against human diseases such as coronary heart disease, cancers, and inflammatory bowel disease. Rutin acts as a quercetin deliverer to the large intestine; moreover, quercetin is extensively metabolized in the large intestine, which suggests that quercetin liberated from rutin and/or its colonic metabolites may play a role. Rutins anti-inflammatory actions are mediated through a molecular mechanism that underlies the quercetin-mediated therapeutic effects: quercetin-mediated inhibition of tumor necrosis factor-alpha (TNF-alpha)-induced nuclear factor kappa B (NFkB) activation. TNF-alpha-induced NFkB activity plays a central role in the production of pro-inflammatory mediators involved in progression of gut inflammation. (PMID:16132362). Rutin is a rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups. It has a role as a metabolite and an antioxidant. It is a disaccharide derivative, a quercetin O-glucoside, a tetrahydroxyflavone and a rutinoside. A flavonol glycoside found in many plants, including buckwheat; tobacco; forsythia; hydrangea; viola, etc. It has been used therapeutically to decrease capillary fragility. Rutin is a natural product found in Ficus virens, Visnea mocanera, and other organisms with data available. A flavonol glycoside found in many plants, including BUCKWHEAT; TOBACCO; FORSYTHIA; HYDRANGEA; VIOLA, etc. It has been used therapeutically to decrease capillary fragility. See also: Quercetin (related); Ginkgo (part of); Chamomile (part of) ... View More ... First isolated from Ruta graveolens (rue). Bioflavanoid. Quercetin 3-rutinoside is found in many foods, some of which are tea, bilberry, common oregano, and lemon grass. A rutinoside that is quercetin with the hydroxy group at position C-3 substituted with glucose and rhamnose sugar groups. C - Cardiovascular system > C05 - Vasoprotectives > C05C - Capillary stabilizing agents > C05CA - Bioflavonoids IPB_RECORD: 541; CONFIDENCE confident structure [Raw Data] CBA04_Rutin_neg_50eV.txt [Raw Data] CBA04_Rutin_pos_50eV.txt [Raw Data] CBA04_Rutin_neg_40eV.txt [Raw Data] CBA04_Rutin_pos_10eV.txt [Raw Data] CBA04_Rutin_neg_20eV.txt [Raw Data] CBA04_Rutin_neg_10eV.txt [Raw Data] CBA04_Rutin_neg_30eV.txt [Raw Data] CBA04_Rutin_pos_40eV.txt [Raw Data] CBA04_Rutin_pos_30eV.txt [Raw Data] CBA04_Rutin_pos_20eV.txt Rutin (Rutoside) is a flavonoid found in many plants and shows a wide range of biological activities including anti-inflammatory, antidiabetic, antioxidant, neuroprotective, nephroprotective, hepatoprotective and reducing Aβ oligomer activities. Rutin can cross the blood brain barrier. Rutin attenuates vancomycin-induced renal tubular cell apoptosis via suppression of apoptosis, mitochondrial dysfunction, and oxidative stress[1][2][3]. Rutin (Rutoside) is a flavonoid found in many plants and shows a wide range of biological activities including anti-inflammatory, antidiabetic, antioxidant, neuroprotective, nephroprotective, hepatoprotective and reducing Aβ oligomer activities. Rutin can cross the blood brain barrier. Rutin attenuates vancomycin-induced renal tubular cell apoptosis via suppression of apoptosis, mitochondrial dysfunction, and oxidative stress[1][2][3].

1,2,3-Trihydroxybenzene

C6H6O3 (126.0316926)

1,2,3-trihydroxybenzene, also known as pyrogallic acid or 1,2,3-benzenetriol, is a member of the class of compounds known as 5-unsubstituted pyrrogallols. 5-unsubstituted pyrrogallols are pyrrogallols that are unsubstituted at th5-position of the benzene ring. 1,2,3-trihydroxybenzene is soluble (in water) and a very weakly acidic compound (based on its pKa). 1,2,3-trihydroxybenzene can be found in arabica coffee, beer, cocoa powder, and coffee, which makes 1,2,3-trihydroxybenzene a potential biomarker for the consumption of these food products. 1,2,3-trihydroxybenzene can be found primarily in blood, feces, and urine. 1,2,3-trihydroxybenzene is an organic compound with the formula C6H3(OH)3. It is a white water-soluble solid although samples are typically brownish because of its sensitivity toward oxygen. It is one of three isomeric benzenetriols . Pyrogallic acid is an odorless white to gray solid. Sinks and mixes with water. (USCG, 1999) Pyrogallol is a benzenetriol carrying hydroxy groups at positions 1, 2 and 3. It has a role as a plant metabolite. It is a phenolic donor and a benzenetriol. Pyrogallol is a natural product found in Gunnera perpensa, Nigella glandulifera, and other organisms with data available. A trihydroxybenzene or dihydroxy phenol that can be prepared by heating GALLIC ACID. See also: Stevia rebaudiuna Leaf (part of); Alchemilla monticola whole (part of); Agrimonia eupatoria flowering top (part of). 1,2,3-Trihydroxybenzene, or pyrogallol is a benzenetriol. It is a white crystalline powder and a powerful reducing agent. It was first prepared by Scheele 1786 by heating gallic acid. An alternate preparation is heating para-chlorophenoldisulphonic acid with potassium hydroxide. 1,2,3-Trihydroxybenzene has been found to be a metabolite of Aspergillus (https://www.tandfonline.com/doi/pdf/10.1080/00021369.1982.10865473). A benzenetriol carrying hydroxy groups at positions 1, 2 and 3. D020011 - Protective Agents > D000975 - Antioxidants Pyrogallol is a polyphenol compound, which has anti-fungal and anti-psoriatic properties. Pyrogallol is a reductant that is able to generate free radicals, in particular superoxide anions. Pyrogallol is a polyphenol compound, which has anti-fungal and anti-psoriatic properties. Pyrogallol is a reductant that is able to generate free radicals, in particular superoxide anions.

Cosmosiin

C21H20O10 (432.105642)

Cosmosiin, also known as apigenin 7-O-glucoside or apigetrin, is a member of the class of compounds known as flavonoid-7-O-glycosides. Flavonoid-7-O-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Cosmosiin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Cosmosiin can be found in a number of food items, such as common thyme, white lupine, common oregano, and orange mint. Cosmosiin can also be found in dandelion coffee and in Teucrium gnaphalodes (Wikipedia). Cosmosiin can also be found plants such as wild celery and anise. Cosmosiin has been shown to exhibit anti-platelet function (PMID: 21834233). Apigenin 7-O-beta-D-glucoside is a glycosyloxyflavone that is apigenin substituted by a beta-D-glucopyranosyl moiety at position 7 via a glycosidic linkage. It has a role as a non-steroidal anti-inflammatory drug, a metabolite and an antibacterial agent. It is a beta-D-glucoside, a dihydroxyflavone, a glycosyloxyflavone and a monosaccharide derivative. It is functionally related to an apigenin. It is a conjugate acid of an apigenin 7-O-beta-D-glucoside(1-). It is an enantiomer of an apigenin 7-O-beta-L-glucoside. Cosmosiin is a natural product found in Galeopsis tetrahit, Carex fraseriana, and other organisms with data available. See also: Chamomile (part of). Apiumetrin, also known as 7-O-beta-D-glucosyl-5,7,4-trihydroxyflavone or cosmosiin, is a member of the class of compounds known as flavonoid-7-o-glycosides. Flavonoid-7-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. Apiumetrin is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Apiumetrin can be found in wild celery, which makes apiumetrin a potential biomarker for the consumption of this food product. Acquisition and generation of the data is financially supported in part by CREST/JST. Annotation level-1 Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

Apigenin

C15H10O5 (270.052821)

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.

Caffeic acid

C9H8O4 (180.0422568)

Caffeic acid is a hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. It has a role as a plant metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 1.13.11.34 (arachidonate 5-lipoxygenase) inhibitor, an antioxidant and an EC 3.5.1.98 (histone deacetylase) inhibitor. It is a hydroxycinnamic acid and a member of catechols. Caffeic Acid is a natural product found in Pavetta indica, Eupatorium cannabinum, and other organisms with data available. Caffeic Acid is an orally bioavailable, hydroxycinnamic acid derivative and polyphenol, with potential anti-oxidant, anti-inflammatory, and antineoplastic activities. Upon administration, caffeic acid acts as an antioxidant and prevents oxidative stress, thereby preventing DNA damage induced by free radicals. Caffeic acid targets and inhibits the histone demethylase (HDM) oncoprotein gene amplified in squamous cell carcinoma 1 (GASC1; JMJD2C; KDM4C) and inhibits cancer cell proliferation. GASC1, a member of the KDM4 subgroup of Jumonji (Jmj) domain-containing proteins, demethylates trimethylated lysine 9 and lysine 36 on histone H3 (H3K9 and H3K36), and plays a key role in tumor cell development. Caffeic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Black Cohosh (part of); Arctium lappa Root (part of); Comfrey Leaf (part of) ... View More ... 3,4-Dihydroxy-trans-cinnamate, also known as trans-Caffeate, is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). trans-Caffeic acid is found in many foods, some of which are flaxseed, cereal and cereal products, common grape, fruits, and common sage. It is also found in wine and coffee in free and conjugated forms. Caffeic acid (CAS: 331-39-5) is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food (PMID:16870009). Caffeic acid has been found to be a microbial metabolite of Escherichia (PMID: 28396925). Caffeic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=331-39-5 (retrieved 2024-06-28) (CAS RN: 331-39-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

Quercetin

C15H10O7 (302.042651)

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

Friedelin

C30H50O (426.386145)

Friedelin is a pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. It has a role as an anti-inflammatory drug, a non-narcotic analgesic, an antipyretic and a plant metabolite. It is a pentacyclic triterpenoid and a cyclic terpene ketone. Friedelin is a natural product found in Diospyros eriantha, Salacia chinensis, and other organisms with data available. A pentacyclic triterpenoid that is perhydropicene which is substituted by an oxo group at position 3 and by methyl groups at the 4, 4a, 6b, 8a, 11, 11, 12b, and 14a-positions (the 4R,4aS,6aS,6bR,8aR,12aR,12bS,14aS,14bS-enantiomer). It is the major triterpenoid constituent of cork. Friedelin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Friedelin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Friedelin can be found in a number of food items such as pomegranate, sugar apple, apple, and mammee apple, which makes friedelin a potential biomarker for the consumption of these food products. Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant .

Amyrin

C30H50O (426.386145)

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

Caryophyllene alpha-oxide

C15H24O (220.18270539999997)

Caryophyllene oxide is an epoxide. It has a role as a metabolite. Caryophyllene oxide is a natural product found in Xylopia emarginata, Eupatorium altissimum, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of). Caryophyllene alpha-oxide is a minor produced of epoxidn. of KGV69-V. Minor production of epoxidn. of KGV69-V Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1]. Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1].

Nonacosane

C29H60 (408.469476)

Nonacosane, also known as CH3-[CH2]27-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Nonacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, nonacosane is considered to be a hydrocarbon lipid molecule. Nonacosane is a straight-chain hydrocarbon with a molecular formula of C29H60. Nonacosane has been identified within several essential oils. Nonacosane has been detected, but not quantified, in several different foods, such as peachs, ginkgo nuts, cauliflowers, arabica coffee, and lambsquarters. This could make nonacosane a potential biomarker for the consumption of these foods. Nonacosane occurs naturally and has been reported to be a component of a pheromone of Orgyia leucostigma, and evidence suggests it plays a role in the chemical communication of several insects, including the female Anopheles stephensi (a mosquito). It can also be prepared synthetically. It has 1,590,507,121 constitutional isomers. Nonacosane, also known as ch3-[ch2]27-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, nonacosane is considered to be a hydrocarbon lipid molecule. Nonacosane can be found in a number of food items such as garden tomato (variety), papaya, brussel sprouts, and wild carrot, which makes nonacosane a potential biomarker for the consumption of these food products. Nonacosane occurs naturally and has been reported to be a component of a pheromone of Orgyia leucostigma, and evidence suggests it plays a role in the chemical communication of several insects, including the female Anopheles stephensi (a mosquito) . Nonacosane is a straight-chain alkane comprising of 29 carbon atoms. It has a role as a plant metabolite and a volatile oil component. Nonacosane is a natural product found in Euphorbia larica, Quercus salicina, and other organisms with data available. See also: Moringa oleifera leaf oil (part of). A straight-chain alkane comprising of 29 carbon atoms. Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1]. Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1].

Epi-alpha-amyrin

C30H50O (426.386145)

Alpha-amyrin is a pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an ursane. alpha-Amyrin is a natural product found in Ficus septica, Ficus virens, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Eupatorium perfoliatum whole (part of) ... View More ... Carissol is found in beverages. Carissol is a constituent of Carissa carandas (karanda). Constituent of Carissa carandas (karanda). Carissol is found in beverages and fruits.

Myricetin

C15H10O8 (318.037566)

Myricetin, also known as cannabiscetin or myricetol, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, myricetin is considered to be a flavonoid lipid molecule. A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3, 4, 5, 5 and 7. Myricetin is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Myricetin is found, on average, in the highest concentration within a few different foods, such as common walnuts, carobs, and fennels and in a lower concentration in welsh onions, yellow bell peppers, and jutes. Myricetin has also been detected, but not quantified in several different foods, such as napa cabbages, sesames, mixed nuts, lichee, and garden cress. Myricetin is a hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3, 4, 5, 5 and 7. It has been isolated from the leaves of Myrica rubra and other plants. It has a role as a cyclooxygenase 1 inhibitor, an antineoplastic agent, an antioxidant, a plant metabolite, a food component, a hypoglycemic agent and a geroprotector. It is a hexahydroxyflavone and a 7-hydroxyflavonol. It is a conjugate acid of a myricetin(1-). Myricetin is a natural product found in Ficus auriculata, Visnea mocanera, and other organisms with data available. Myricetin is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Quercetin (related). Flavanol found in a wide variety of foodstuffs especially in red table wine, bee pollen, bilberries, blueberries, bog whortleberries, broad beans, Chinese bajberry, corn poppy leaves, cranberries, crowberries, blackcurrants, dock leaves, fennel, grapes, parsley, perilla, rutabaga, dill weed and tea (green and black). Glycosides are also widely distributed. Potential nutriceutical showing anti-HIV activity A hexahydroxyflavone that is flavone substituted by hydroxy groups at positions 3, 3, 4, 5, 5 and 7. It has been isolated from the leaves of Myrica rubra and other plants. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Raw Data] CB066_Myricetin_pos_30eV_CB000028.txt [Raw Data] CB066_Myricetin_pos_20eV_CB000028.txt [Raw Data] CB066_Myricetin_pos_40eV_CB000028.txt [Raw Data] CB066_Myricetin_pos_50eV_CB000028.txt [Raw Data] CB066_Myricetin_pos_10eV_CB000028.txt [Raw Data] CB066_Myricetin_neg_10eV_000019.txt [Raw Data] CB066_Myricetin_neg_40eV_000019.txt [Raw Data] CB066_Myricetin_neg_50eV_000019.txt [Raw Data] CB066_Myricetin_neg_20eV_000019.txt [Raw Data] CB066_Myricetin_neg_30eV_000019.txt Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities. Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities.

Octanol

C8H18O (130.1357578)

1-Octanol, also known as octan-1-ol, is the organic compound with the molecular formula CH3(CH2)7OH. It is a fatty alcohol. Many other isomers are also known generically as octanols. Octanol is mainly produced industrially by the oligomerization of ethylene using triethylaluminium followed by oxidation of the alkylaluminium products. This route is known as the Ziegler alcohol synthesis. Octanol also occurs naturally in the form of esters in some essential oils. Octanol and water are immiscible. The distribution of a compound between water and octanol is used to calculate the partition coefficient (logP) of that molecule. Water/octanol partitioning is a good approximation of the partitioning between the cytosol and lipid membranes of living systems. Octanol is a colorless, slightly viscous liquid used as a defoaming or wetting agent. It is also used as a solvent for protective coatings, waxes, and oils, and as a raw material for plasticizers. It is also one of many compounds derived from tobacco and tobacco smoke and shown to increase the permeability of the membranes of human lung fibroblasts (PMID 7466833). Occurs in the form of esters in some essential oils. Flavouring agent. 1-Octanol is found in many foods, some of which are common wheat, lime, tea, and corn. D012997 - Solvents 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2]. 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2].

(R)-1-Octen-3-ol

C8H16O (128.1201086)

Isolated from a number of essential oils, e.g. lavender, leek, mint and mushrooms. Food odorant responsible for typical mushroom odour. Flavouring ingredient. (R)-1-Octen-3-ol is found in mushrooms, onion-family vegetables, and herbs and spices. (R)-1-Octen-3-ol, also known as 1-vinylhexanol or 3-hydroxy-1-octene, belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2]. Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2].

Chromium

Cr (51.94051)

D018977 - Micronutrients > D014131 - Trace Elements

beta-Caryophyllene

C15H24 (204.18779039999998)

beta-Caryophyllene, also known as caryophyllene or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils including that of Syzygium aromaticum (cloves), Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. beta-Caryophyllene is notable for having both a cyclobutane ring and a trans-double bond in a nine-membered ring, both rarities in nature (Wikipedia). beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, fig, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. beta-Caryophyllene can be found in feces and saliva. (-)-Caryophyllene. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=87-44-5 (retrieved 2024-08-07) (CAS RN: 87-44-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

N-(2-Hydroxyisobutyl)-2,4,8,10,12-tetradecapentaenamide

C18H27NO2 (289.20416819999997)

Hydroxy-gamma-sanshool is found in herbs and spices. Hydroxy-gamma-sanshool is a constituent of Zanthoxylum piperitum (Japanese pepper tree) Constituent of Zanthoxylum subspecies N-(2-Hydroxyisobutyl)-2,4,8,10,12-tetradecapentaenamide is found in herbs and spices.

Quercetin 3-galactoside

C21H20O12 (464.09547200000003)

Quercetin 3-O-beta-D-galactopyranoside is a quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity. It has a role as a hepatoprotective agent and a plant metabolite. It is a tetrahydroxyflavone, a monosaccharide derivative, a beta-D-galactoside and a quercetin O-glycoside. Hyperoside is a natural product found in Lotus ucrainicus, Visnea mocanera, and other organisms with data available. See also: Bilberry (part of); Menyanthes trifoliata leaf (part of); Crataegus monogyna flowering top (part of). Quercetin 3-galactoside is found in alcoholic beverages. Quercetin 3-galactoside occurs widely in plants, e.g. in apple peel and Hypericum perforatum (St Johns wort).Hyperoside is the 3-O-galactoside of quercetin. It is a medicinally active compound that can be isolated from Drosera rotundifolia, from the Stachys plant, from Prunella vulgaris, from Rumex acetosella and from St Johns wort. (Wikipedia A quercetin O-glycoside that is quercetin with a beta-D-galactosyl residue attached at position 3. Isolated from Artemisia capillaris, it exhibits hepatoprotective activity. Occurs widely in plants, e.g. in apple peel and Hypericum perforatum (St Johns wort) Acquisition and generation of the data is financially supported in part by CREST/JST. Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2]. Hyperoside is a NF-κB inhibitor, found from Hypericum monogynum. Hyperoside shows anti-tumor, antifungal, anti-inflammatory, anti-viral, and anti-oxidative activities, and can induce apoptosis[1][2].

HEPTACOSANE

C27H56 (380.4381776)

A straight-chain alkane with 27 carbon atoms.

Nonanal

C9H18O (142.1357578)

Nonanal, also known as nonyl aldehyde or pelargonaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, nonanal is considered to be a fatty aldehyde lipid molecule. Nonanal acts synergistically with carbon dioxide in that regard. Nonanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Nonanal exists in all eukaryotes, ranging from yeast to humans. Nonanal is an aldehydic, citrus, and fat tasting compound. nonanal is found, on average, in the highest concentration in a few different foods, such as corns, tea, and gingers and in a lower concentration in sweet oranges, carrots, and limes. nonanal has also been detected, but not quantified, in several different foods, such as olives, cereals and cereal products, chinese cinnamons, common grapes, and oats. This could make nonanal a potential biomarker for the consumption of these foods. Nonanal has been identified as a compound that attracts Culex mosquitoes. Nonanal is a potentially toxic compound. Nonanal has been found to be associated with several diseases such as pervasive developmental disorder not otherwise specified, autism, crohns disease, and ulcerative colitis; also nonanal has been linked to the inborn metabolic disorders including celiac disease. Nonanal, also called nonanaldehyde, pelargonaldehyde or Aldehyde C-9, is an alkyl aldehyde. Although it occurs in several natural oils, it is produced commercially by hydroformylation of 1-octene. A colourless, oily liquid, nonanal is a component of perfumes. Nonanal is a clear brown liquid characterized by a rose-orange odor. Insoluble in water. Found in at least 20 essential oils, including rose and citrus oils and several species of pine oil. Nonanal is a saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. It has a role as a human metabolite and a plant metabolite. It is a saturated fatty aldehyde, a n-alkanal and a medium-chain fatty aldehyde. It is functionally related to a nonanoic acid. Nonanal is a natural product found in Teucrium montanum, Eupatorium cannabinum, and other organisms with data available. Nonanal is a uremic toxin. Uremic toxins can be subdivided into three major groups based upon their chemical and physical characteristics: 1) small, water-soluble, non-protein-bound compounds, such as urea; 2) small, lipid-soluble and/or protein-bound compounds, such as the phenols and 3) larger so-called middle-molecules, such as beta2-microglobulin. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease.Nonanal belongs to the family of Medium-chain Aldehydes. These are An aldehyde with a chain length containing between 6 and 12 carbon atoms. Found in various plant sources including fresh fruits, citrus peels, cassava (Manihot esculenta), rice (Oryza sativa). Flavouring ingredient A saturated fatty aldehyde formally arising from reduction of the carboxy group of nonanoic acid. Metabolite observed in cancer metabolism. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1]. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1].

Phenethyl rutinoside

C20H30O10 (430.183888)

Phenethyl rutinoside is found in citrus. Phenethyl rutinoside is isolated from Citrus unshiu (Satsuma mandarin Isolated from Citrus unshiu (Satsuma mandarin). Phenethyl rutinoside is found in citrus and pomegranate.

Limocitrin 3-glucoside

C23H24O13 (508.1216854)

Limocitrin 3-glucoside is found in citrus. Limocitrin 3-glucoside is a constituent of Citrus species fruit peels Constituent of Citrus subspecies fruit peels. Limocitrin 3-glucoside is found in lemon and citrus.

Benzyl salicylate

C14H12O3 (228.0786402)

Benzyl salicylate is found in cloves. Benzyl salicylate is isolated from essential oils e.g. Dianthus caryophyllus, Populus, Primula species Fixative in perfumes and flavourings Benzyl salicylate is a salicylic acid benzyl ester, a chemical compound most frequently used in cosmetics. It appears as an almost colourless liquid and is rather faint or odorless in nature Isolated from essential oils e.g. Dianthus caryophyllus, Populus, Primula subspecies Fixative in perfumes and flavourings D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates Benzyl salicylate?is a salicylic acid benzyl ester. It can be used as a fragrance additive or UV light absorber. Benzyl salicylate?is a salicylic acid benzyl ester. It can be used as a fragrance additive or UV light absorber.

cis-Caffeic acid

C9H8O4 (180.0422568)

Caffeic acid, also known as caffeate, belongs to the class of organic compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. Caffeic acid exists in all living species, ranging from bacteria to humans. It is the precursor to ferulic acid, coniferyl alcohol, and sinapyl alcohol, all of which are significant building blocks in lignin. Outside of the human body, caffeic acid has been detected, but not quantified in fats and oils and nuts. Caffeic acid is formally rated as a possible carcinogen (by IARC 2B) and is also a potentially toxic compound. Caffeic acid has a variety of potential pharmacological effects in in vitro studies and in animal models, and the inhibitory effect of caffeic acid on cancer cell proliferation by an oxidative mechanism in the human HT-1080 fibrosarcoma cell line has recently been established. It occurs at high levels in black chokeberry (141 mg per 100 g) and in fairly high level in lingonberry (6 mg per 100 g). D020011 - Protective Agents > D000975 - Antioxidants Found in olive oil, peanuts and other plant sources Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

7-Glucosyl-luteolin

C21H20O12 (464.09547200000003)

Friedelin

C30H50O (426.386145)

Friedelin is a member of the class of compounds known as triterpenoids. Triterpenoids are terpene molecules containing six isoprene units. Friedelin is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Friedelin can be found in a number of food items such as apple, pear, mammee apple, and sugar apple, which makes friedelin a potential biomarker for the consumption of these food products. Friedelin is a triterpenoid chemical compound found in Azima tetracantha, Orostachys japonica, and Quercus stenophylla. Friedelin is also found in the roots of the Cannabis plant .

Quercetin 3-O-rhamnoside

C21H20O11 (448.100557)

Heptacosane

C27H56 (380.4381776)

Heptacosane, also known as CH3-[CH2]25-CH3, belongs to the class of organic compounds known as alkanes. These are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2, and consist entirely of hydrogen atoms and saturated carbon atoms. Thus, heptacosane is a hydrocarbon lipid molecule, is very hydrophobic, practically insoluble in water, and relatively neutral. Heptacosane has been detected in avocado, sunflowers, peachs, sweet cherries, and wild carrots. This could make heptacosane a potential biomarker for the consumption of these foods. Heptacosane, in addition to other flavonoids, alkaloids and sugars, extracted from the root of Trichosanthes dioica, exhibited antimicrobial activity against Proteus mirabilis and Bacillus subtilis http://www.phytojournal.com/archives/?year=2016&vol=5&issue=5&part=F&ArticleId=985 Heptacosane, also known as ch3-[ch2]25-ch3, is a member of the class of compounds known as alkanes. Alkanes are acyclic branched or unbranched hydrocarbons having the general formula CnH2n+2 , and therefore consisting entirely of hydrogen atoms and saturated carbon atoms. Thus, heptacosane is considered to be a hydrocarbon lipid molecule. Heptacosane can be found in a number of food items such as wild carrot, linden, sweet cherry, and papaya, which makes heptacosane a potential biomarker for the consumption of these food products. The term higher alkanes is sometimes used literally as "alkanes with a higher number of carbon atoms". One definition distinguishes the higher alkanes as the n-alkanes that are solid under natural conditions .

Benzyl alcohol beta-D-rutinoside

C19H28O10 (416.16823880000004)

Benzyl alcohol beta-d-rutinoside is a member of the class of compounds known as O-glycosyl compounds. O-glycosyl compounds are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Benzyl alcohol beta-d-rutinoside is soluble (in water) and a very weakly acidic compound (based on its pKa). Benzyl alcohol beta-d-rutinoside can be found in common grape, which makes benzyl alcohol beta-d-rutinoside a potential biomarker for the consumption of this food product.

beta-Phenylethanol beta-D-rutinoside

C20H30O10 (430.183888)

Beta-phenylethanol beta-d-rutinoside is a member of the class of compounds known as O-glycosyl compounds. O-glycosyl compounds are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Beta-phenylethanol beta-d-rutinoside is soluble (in water) and a very weakly acidic compound (based on its pKa). Beta-phenylethanol beta-d-rutinoside can be found in common grape, which makes beta-phenylethanol beta-d-rutinoside a potential biomarker for the consumption of this food product.

Anthemoside

C21H20O10 (432.105642)

Constituent of Anthemis nobilis (Roman chamomile). Anthemoside is found in herbs and spices.

Ursolic Acid

C30H48O3 (456.36032579999994)

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

Gossypetin 7,8-dimethyl ether 4-glucoside

C23H24O13 (508.1216854)

Gossypetin 7,8-dimethyl ether 3-glucoside

C23H24O13 (508.1216854)

Gossypetin 3-rutinoside

C27H30O17 (626.148293)

Apigenin

C15H10O5 (270.052821)

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.

Hirsutrin

C21H20O12 (464.09547200000003)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Isoquercetin (Quercetin 3-glucoside) is a naturally occurring polyphenol that has antioxidant, anti-proliferative, and anti-inflammatory properties. Isoquercetin alleviates ethanol-induced hepatotoxicity, oxidative stress, and inflammatory responses via the Nrf2/ARE antioxidant signaling pathway[1]. Isoquercetin regulates the expression of nitric oxide synthase 2 (NO2) via modulating the nuclear factor-κB (NF-κB) transcription regulation system. Isoquercetin has high bioavailability and low toxicity, is a promising candidate agent to prevent birth defects in diabetic pregnancies[2]. Isoquercetin (Quercetin 3-glucoside) is a naturally occurring polyphenol that has antioxidant, anti-proliferative, and anti-inflammatory properties. Isoquercetin alleviates ethanol-induced hepatotoxicity, oxidative stress, and inflammatory responses via the Nrf2/ARE antioxidant signaling pathway[1]. Isoquercetin regulates the expression of nitric oxide synthase 2 (NO2) via modulating the nuclear factor-κB (NF-κB) transcription regulation system. Isoquercetin has high bioavailability and low toxicity, is a promising candidate agent to prevent birth defects in diabetic pregnancies[2]. Isoquercitrin (Isoquercitroside) is an effective antioxidant and an eosinophilic inflammation suppressor. Isoquercitrin (Isoquercitroside) is an effective antioxidant and an eosinophilic inflammation suppressor.

hyperin

C21H20O12 (464.09547200000003)

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

Quercitrin

C21H20O11 (448.100557)

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 (302.042651)

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

Isoquercetin

C21H20O12 (464.09547200000003)

COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Isoquercetin (Quercetin 3-glucoside) is a naturally occurring polyphenol that has antioxidant, anti-proliferative, and anti-inflammatory properties. Isoquercetin alleviates ethanol-induced hepatotoxicity, oxidative stress, and inflammatory responses via the Nrf2/ARE antioxidant signaling pathway[1]. Isoquercetin regulates the expression of nitric oxide synthase 2 (NO2) via modulating the nuclear factor-κB (NF-κB) transcription regulation system. Isoquercetin has high bioavailability and low toxicity, is a promising candidate agent to prevent birth defects in diabetic pregnancies[2]. Isoquercetin (Quercetin 3-glucoside) is a naturally occurring polyphenol that has antioxidant, anti-proliferative, and anti-inflammatory properties. Isoquercetin alleviates ethanol-induced hepatotoxicity, oxidative stress, and inflammatory responses via the Nrf2/ARE antioxidant signaling pathway[1]. Isoquercetin regulates the expression of nitric oxide synthase 2 (NO2) via modulating the nuclear factor-κB (NF-κB) transcription regulation system. Isoquercetin has high bioavailability and low toxicity, is a promising candidate agent to prevent birth defects in diabetic pregnancies[2]. Isoquercitrin (Isoquercitroside) is an effective antioxidant and an eosinophilic inflammation suppressor. Isoquercitrin (Isoquercitroside) is an effective antioxidant and an eosinophilic inflammation suppressor.

5-hydroxy-2-methyl-4H-chromen-4-one

C10H8O3 (176.0473418)

Rutin

C27H30O16 (610.153378)

C - Cardiovascular system > C05 - Vasoprotectives > C05C - Capillary stabilizing agents > C05CA - Bioflavonoids CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2352 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.724 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.728 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 1921; CONFIDENCE confident structure Rutin (Rutoside) is a flavonoid found in many plants and shows a wide range of biological activities including anti-inflammatory, antidiabetic, antioxidant, neuroprotective, nephroprotective, hepatoprotective and reducing Aβ oligomer activities. Rutin can cross the blood brain barrier. Rutin attenuates vancomycin-induced renal tubular cell apoptosis via suppression of apoptosis, mitochondrial dysfunction, and oxidative stress[1][2][3]. Rutin (Rutoside) is a flavonoid found in many plants and shows a wide range of biological activities including anti-inflammatory, antidiabetic, antioxidant, neuroprotective, nephroprotective, hepatoprotective and reducing Aβ oligomer activities. Rutin can cross the blood brain barrier. Rutin attenuates vancomycin-induced renal tubular cell apoptosis via suppression of apoptosis, mitochondrial dysfunction, and oxidative stress[1][2][3].

1-(2,6-dihydroxyphenyl)butan-1-one

C10H12O3 (180.0786402)

8-Methoxynaphthalene-1-ol

C11H10O2 (174.06807600000002)

1,8-dimethoxynaphthalene

C12H12O2 (188.0837252)

Benzyl salicylate

C14H12O3 (228.0786402)

D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4381; ORIGINAL_PRECURSOR_SCAN_NO 4379 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4375; ORIGINAL_PRECURSOR_SCAN_NO 4373 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4383; ORIGINAL_PRECURSOR_SCAN_NO 4379 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4381; ORIGINAL_PRECURSOR_SCAN_NO 4376 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4396; ORIGINAL_PRECURSOR_SCAN_NO 4394 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 4398; ORIGINAL_PRECURSOR_SCAN_NO 4397 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9607; ORIGINAL_PRECURSOR_SCAN_NO 9606 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9642; ORIGINAL_PRECURSOR_SCAN_NO 9638 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9614; ORIGINAL_PRECURSOR_SCAN_NO 9611 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9638; ORIGINAL_PRECURSOR_SCAN_NO 9635 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9641; ORIGINAL_PRECURSOR_SCAN_NO 9638 CONFIDENCE standard compound; INTERNAL_ID 962; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 9646; ORIGINAL_PRECURSOR_SCAN_NO 9641 Benzyl salicylate?is a salicylic acid benzyl ester. It can be used as a fragrance additive or UV light absorber. Benzyl salicylate?is a salicylic acid benzyl ester. It can be used as a fragrance additive or UV light absorber.

Hyperoside

C21H20O12 (464.09547200000003)

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

Caffeate

C9H8O4 (180.0422568)

D020011 - Protective Agents > D000975 - Antioxidants KEIO_ID C107 Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

Caffeic Acid

C9H8O4 (180.0422568)

A hydroxycinnamic acid that is cinnamic acid in which the phenyl ring is substituted by hydroxy groups at positions 3 and 4. It exists in cis and trans forms; the latter is the more common. 3,4-dihydroxycinnamic acid, also known as caffeic acid or trans-caffeate, is a member of the class of compounds known as hydroxycinnamic acids. Hydroxycinnamic acids are compounds containing an cinnamic acid where the benzene ring is hydroxylated. 3,4-dihydroxycinnamic acid is slightly soluble (in water) and a weakly acidic compound (based on its pKa). 3,4-dihydroxycinnamic acid can be found in fats and oils and nuts, which makes 3,4-dihydroxycinnamic acid a potential biomarker for the consumption of these food products. 3,4-dihydroxycinnamic acid exists in all eukaryotes, ranging from yeast to humans. Caffeic acid is an organic compound that is classified as a hydroxycinnamic acid. This yellow solid consists of both phenolic and acrylic functional groups. It is found in all plants because it is a key intermediate in the biosynthesis of lignin, one of the principal components of plant biomass and its residues . Caffeic acid is a polyphenol present in normal human urine positively correlated to coffee consumption and influenced by the dietary intake of diverse types of food. (PMID:16870009) [HMDB]. Caffeic acid is found in many foods, some of which are cardoon, coriander, common persimmon, and irish moss. D020011 - Protective Agents > D000975 - Antioxidants Annotation level-2 CONFIDENCE standard compound; INTERNAL_ID 167 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.412 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.403 Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

Myricetin

C15H10O8 (318.037566)

COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS relative retention time with respect to 9-anthracene Carboxylic Acid is 0.783 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.784 Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities. Myricetin is a common plant-derived flavonoid with a wide range of activities including strong anti-oxidant, anticancer, antidiabetic and anti-inflammatory activities.

Catechol

C15H14O6 (290.0790344)

Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM. Catechin ((+)-Catechin) inhibits cyclooxygenase-1 (COX-1) with an IC50 of 1.4 μM.

Apigetrin

C21H20O10 (432.105642)

Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

Octanol

C8H18O (130.1357578)

D012997 - Solvents 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2]. 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2].

Pyrogallol

C6H6O3 (126.0316926)

caryophyllene

C15H24 (204.18779039999998)

A beta-caryophyllene in which the stereocentre adjacent to the exocyclic double bond has S configuration while the remaining stereocentre has R configuration. It is the most commonly occurring form of beta-caryophyllene, occurring in many essential oils, particularly oil of cloves. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents β-Caryophyllene is a CB2 receptor agonist. β-Caryophyllene is a CB2 receptor agonist.

Nonanal

C9H18O (142.1357578)

Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1]. Nonanal is a saturated fatty aldehyde with antidiarrhoeal activity[1].

1-OCTEN-3-OL

C8H16O (128.1201086)

Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2]. Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2].

Limocitrin 3-glucoside

C23H24O13 (508.1216854)

Octan-1-ol

C8H18O (130.1357578)

An octanol carrying the hydroxy group at position 1.

Jyperin

C21H20O12 (464.09547200000003)

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

FOH 8:1

C8H16O (128.1201086)

Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2]. Oct-1-en-3-ol, a fatty acid fragrant, is a self-stimulating oxylipin messenger. Oct-1-en-3-ol serves as a signaling molecule in plant cellular responses, plant-herbivore interactions, and plant-plant interactions. Oct-1-en-3-ol causes dopamine neuron degeneration through disruption of dopamine handling[1][2].

FOH 8:0

C8H18O (130.1357578)

D012997 - Solvents 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2]. 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2].

Chrysanthemin

C21H21O11 (449.10838160000003)

cosmetin

C21H20O10 (432.105642)

Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2]. Apigenin-7-glucoside (Apigenin-7-O-β-D-glucopyranoside) exhibits significant anti-proliferative and antioxidant activity and scavenges reactive oxygen species (ROS)[1][2].

Versulin

C15H10O5 (270.052821)

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.

Quertin

C15H10O7 (302.042651)

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 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].

99-50-3

C7H6O4 (154.0266076)

D020011 - Protective Agents > D016588 - Anticarcinogenic Agents D000970 - Antineoplastic Agents Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect. Protocatechuic acid is a phenolic compound which exhibits neuroprotective effect.

Piral

C6H6O3 (126.0316926)

D020011 - Protective Agents > D000975 - Antioxidants Pyrogallol is a polyphenol compound, which has anti-fungal and anti-psoriatic properties. Pyrogallol is a reductant that is able to generate free radicals, in particular superoxide anions. Pyrogallol is a polyphenol compound, which has anti-fungal and anti-psoriatic properties. Pyrogallol is a reductant that is able to generate free radicals, in particular superoxide anions.

Vanillate

C8H8O4 (168.0422568)

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

AI3-63211

C9H8O4 (180.0422568)

D020011 - Protective Agents > D000975 - Antioxidants Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO). Caffeic acid is an inhibitor of both TRPV1 ion channel and 5-Lipoxygenase (5-LO).

Urson

C30H48O3 (456.36032579999994)

D018501 - Antirheumatic Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D016861 - Cyclooxygenase Inhibitors C274 - Antineoplastic Agent > C129839 - Apoptotic Pathway-targeting Antineoplastic Agent 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 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.

Nonacosane

C29H60 (408.469476)

Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1]. Nonacosane, isolated from Baphia massaiensis, exhibits weak activities against E. coli, B. subtilis, P. aeruginosa and S. aureus[1].

viminalol

C30H50O (426.386145)

Alpha-amyrin is a pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group. It is a pentacyclic triterpenoid and a secondary alcohol. It derives from a hydride of an ursane. alpha-Amyrin is a natural product found in Ficus septica, Ficus virens, and other organisms with data available. See also: Calendula Officinalis Flower (part of); Viburnum opulus bark (part of); Eupatorium perfoliatum whole (part of) ... View More ...

AI3-36283

C27H56 (380.4381776)

AI3-00517

C14H12O3 (228.0786402)

D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates Benzyl salicylate?is a salicylic acid benzyl ester. It can be used as a fragrance additive or UV light absorber. Benzyl salicylate?is a salicylic acid benzyl ester. It can be used as a fragrance additive or UV light absorber.

Caryophyllene oxide

C15H24O (220.18270539999997)

Constituent of oil of cloves (Eugenia caryophyllata)and is) also in oils of Betula alba, Mentha piperita (peppermint) and others. Caryophyllene alpha-oxide is found in many foods, some of which are spearmint, cloves, ceylon cinnamon, and herbs and spices. Caryophyllene beta-oxide is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Caryophyllene beta-oxide is practically insoluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Within the cell, caryophyllene beta-oxide is primarily located in the membrane (predicted from logP). It can also be found in the extracellular space. Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1]. Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1].

Benzyl alcohol beta-D-rutinoside

C19H28O10 (416.16823880000004)

Benzyl alcohol beta-d-rutinoside is a member of the class of compounds known as O-glycosyl compounds. O-glycosyl compounds are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Benzyl alcohol beta-d-rutinoside is soluble (in water) and a very weakly acidic compound (based on its pKa). Benzyl alcohol beta-d-rutinoside can be found in common grape, which makes benzyl alcohol beta-d-rutinoside a potential biomarker for the consumption of this food product.

2-Phenylethyl D-rutinoside

C20H30O10 (430.183888)

epoxide

C15H24O (220.18270539999997)

Caryophyllene oxide is an epoxide. It has a role as a metabolite. Caryophyllene oxide is a natural product found in Xylopia emarginata, Eupatorium altissimum, and other organisms with data available. See also: Cannabis sativa subsp. indica top (part of). A natural product found in Cupania cinerea. Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1]. Caryophyllene oxide, isolated from from Hymenaea courbaril, possesses analgesic and anti-inflammatory activity[1].

1-octanol

C8H18O (130.1357578)

D012997 - Solvents 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2]. 1-Octanol (Octanol), a saturated fatty alcohol, is a T-type calcium channels (T-channels) inhibitor with an IC50 of 4 μM for native T-currents[1]. 1-Octanol is a highly attractive biofuel with diesel-like properties[2].

Caryophyllene epoxide

C15H24O (220.18270539999997)

Vitamin P

C27H30O16 (610.153378)

Oct-1-en-3-ol

C8H16O (128.1201086)

An alkenyl alcohol with a structure based on a C8 unbranched chain with the hydroxy group at C-2 and unsaturation at C-1-C-2. It is a major volatile compound present in many mushrooms and fungi.

1-(2,6-dihydroxyphenyl)-3-hydroxybutan-1-one

C10H12O4 (196.0735552)

2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-3-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]chromen-4-one

C22H22O12 (478.1111212)

3,5-dihydroxy-2-(3-hydroxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-7,8-dimethoxychromen-4-one

C23H24O13 (508.1216854)

(2r,3r)-2-(3,4-dihydroxyphenyl)-3,5-dihydroxy-7,8-dimethoxy-2,3-dihydro-1-benzopyran-4-one

C17H16O8 (348.0845136)

[(2r,3r,4r,5s,6s)-6-{[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxochromen-3-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxybenzoate

C28H24O14 (584.1166003999999)

(6s)-2-[2-(4-hydroxyphenyl)ethyl]-6-[2-(4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)ethyl]-5,6-dihydropyran-4-one

C27H32O9 (500.2046222)

2-(4-hydroxy-3,5-dimethoxyphenyl)-3,6-bis(hydroxymethyl)-hexahydro-2h-pyrano[2,3-b][1,4]dioxine-7,8-diol

C17H24O10 (388.13694039999996)

(3s,7s)-3,7-dihydroxy-1,9-bis(4-hydroxyphenyl)nonan-5-one

C21H26O5 (358.17801460000004)

apigetrin

C21H20O10 (432.105642)

{"Ingredient_id": "HBIN016480","Ingredient_name": "apigetrin","Alias": "CHEMBL487995; SR-05000002285; Galactosyl-7-apigenin; EINECS 209-430-5; 5-Hydroxy-2-(4-hydroxyphenyl)-7-(4,5,6-trihydroxy-3-(hydroxymethyl)(2-oxanyloxy))-4H-chromen-4-one; Cosemetin; 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one; COSMOSIIN; 4H-1-Benzopyran-4-one, 7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)- (9CI); Apigenin, 7-beta-D-glucopyranoside; Apigenin 7-O-beta-D-glucopyranoside; 7-(beta-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one; Cosmosiine; 7-O-(beta-D-Glucosyl)apigenin; Thalictiin; SR-05000002285-3; A831652; Cosmosioside; 23598-21-2; NSC 407303; Apigetrin; NCGC00163513-01; CCG-208379; 62532-75-6; 5-hydroxy-2-(4-hydroxyphenyl)-7-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-1-benzopyran-4-one; UNII-7OF2S66PCH; SR-05000002285-2; 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-chromen-4-one; AC1NUZ8G; Apigenin, 7-beta-D-galactopyranoside; 7-[(2S,3R,4S,5R,6R)-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]oxy-2-(4-hydroxyphenyl)-5-oxidanyl-chromen-4-one; 7OF2S66PCH; Cosmosiin (8CI)","Ingredient_formula": "C21H20O10","Ingredient_Smile": "C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O","Ingredient_weight": "432.4 g/mol","OB_score": "NA","CAS_id": "NA","SymMap_id": "SMIT19095","TCMID_id": "30618","TCMSP_id": "NA","TCM_ID_id": "21625","PubChem_id": "12304093","DrugBank_id": "NA"}

8-methoxynaphthalen-1-ol

C11H10O2 (174.06807600000002)

3-(4-hydroxy-3,5-dimethoxyphenyl)-2,6-bis(hydroxymethyl)-hexahydro-2h-pyrano[2,3-b][1,4]dioxine-7,8-diol

C17H24O10 (388.13694039999996)

(2r,3r,4s,5s,6r)-2-{[(1s,2r)-1,3-dihydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C18H28O11 (420.16315380000003)

(2s)-2,6-bis[2-(4-hydroxyphenyl)ethyl]-2,3-dihydropyran-4-one

C21H22O4 (338.1518012)

(3r)-3-(2,3-dihydroxyphenoxy)butanoic acid

C10H12O5 (212.06847019999998)

(3r,7r)-3-hydroxy-1,9-bis(4-hydroxyphenyl)-7-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonan-5-one

C27H36O10 (520.2308356)

(2s,3s,4as,6r,7s,8s,8ar)-2-(4-hydroxy-3,5-dimethoxyphenyl)-3,6-bis(hydroxymethyl)-hexahydro-2h-pyrano[2,3-b][1,4]dioxine-7,8-diol

C17H24O10 (388.13694039999996)

5,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-8-methoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C23H24O13 (508.1216854)

3-hydroxy-1,9-bis(4-hydroxyphenyl)-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}nonan-5-one

C27H36O10 (520.2308356)

6-(but-2-en-2-yl)-4-hydroxy-3,3,5-trimethyloxan-2-one

C12H20O3 (212.14123700000002)

(4s,5r,6r)-6-[(2e)-but-2-en-2-yl]-4-hydroxy-3,3,5-trimethyloxan-2-one

C12H20O3 (212.14123700000002)

2-(3,5-dihydroxy-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}phenyl)-5,7-dihydroxychromen-4-one

C21H20O11 (448.100557)

(2r,3r,4as,6r,7s,8s,8ar)-3-(4-hydroxy-3,5-dimethoxyphenyl)-2,6-bis(hydroxymethyl)-hexahydro-2h-pyrano[2,3-b][1,4]dioxine-7,8-diol

C17H24O10 (388.13694039999996)

5-hydroxy-2-(hydroxymethyl)chromen-4-one

C10H8O4 (192.0422568)

taxifolin 3'-glucoside

C21H22O12 (466.1111212)

2-(3,4-dihydroxy-5-methoxyphenyl)-5,7-dihydroxy-8-methoxy-3-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

C23H24O13 (508.1216854)

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

C21H20O12 (464.09547200000003)

2-(3,4-dihydroxyphenyl)-5-hydroxy-7,8-dimethoxy-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C23H24O13 (508.1216854)

β-caryophyllene oxide

C15H24O (220.18270539999997)

5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-8-methoxy-3-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one

C24H26O13 (522.1373346)

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

C21H22O12 (466.1111212)

2,6-bis[2-(4-hydroxyphenyl)ethyl]-2,3-dihydropyran-4-one

C21H22O4 (338.1518012)

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-methoxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C22H22O13 (494.1060362)

2-{3,5-dihydroxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]phenyl}-5,7-dihydroxychromen-4-one

C21H20O11 (448.100557)

(2r,4s)-4-(4-hydroxy-5-methoxynaphthalen-1-yl)-2-methyl-3,4-dihydro-2h-1-benzopyran-5-ol

C21H20O4 (336.13615200000004)

5,7-dihydroxy-8-methoxy-3-{[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-2-(3,4,5-trihydroxyphenyl)chromen-4-one

C22H22O13 (494.1060362)

2-(3,4-dihydroxyphenyl)-5,7,8-trihydroxy-3-{[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy}chromen-4-one

C27H30O17 (626.148293)

3,5,7-trihydroxy-8-methoxy-2-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one

C23H24O13 (508.1216854)

2,4,6-trimethyloct-6-ene-3,5-diol

C11H22O2 (186.1619712)

1-[2,6-dihydroxy-3-(5-hydroxy-2-methyl-3,4-dihydro-2h-1-benzopyran-4-yl)phenyl]butan-1-one

C20H22O5 (342.1467162)

4-(1-hydroxy-8-methoxynaphthalen-2-yl)-2-methyl-3,4-dihydro-2h-1-benzopyran-5-ol

C21H20O4 (336.13615200000004)

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

C22H22O12 (478.1111212)

3,5,7-trihydroxy-8-methoxy-2-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)chromen-4-one

C23H24O13 (508.1216854)

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

C27H30O17 (626.148293)

1-{2,6-dihydroxy-3-[(2s,4r)-5-hydroxy-2-methyl-3,4-dihydro-2h-1-benzopyran-4-yl]phenyl}butan-1-one

C20H22O5 (342.1467162)

(2r,4s)-4-(1-hydroxy-8-methoxynaphthalen-2-yl)-2-methyl-3,4-dihydro-2h-1-benzopyran-5-ol

C21H20O4 (336.13615200000004)

2-(3,4-dihydroxyphenyl)-5-hydroxy-7,8-dimethoxy-3-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C23H24O13 (508.1216854)

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

C21H22O13 (482.1060362)

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

C21H22O13 (482.1060362)

{5-hydroxy-2-[4-hydroxy-3-(sulfooxy)phenyl]-7,8-dimethoxy-4-oxochromen-3-yl}oxidanesulfonic acid

C17H14O14S2 (505.9824984)

2-{[1,3-dihydroxy-1-(3,4,5-trimethoxyphenyl)propan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C18H28O11 (420.16315380000003)

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-methoxy-3-{[(2s,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}chromen-4-one

C22H22O13 (494.1060362)

4-(4-hydroxy-5-methoxynaphthalen-1-yl)-2-methyl-3,4-dihydro-2h-1-benzopyran-5-ol

C21H20O4 (336.13615200000004)

(3r,4r,5r,6e)-2,4,6-trimethyloct-6-ene-3,5-diol

C11H22O2 (186.1619712)

(3s)-1-(2,6-dihydroxyphenyl)-3-hydroxybutan-1-one

C10H12O4 (196.0735552)