NCBI Taxonomy: 7638

Euechinoidea (ncbi_taxid: 7638)

found 245 associated metabolites at subclass taxonomy rank level.

Ancestor: Echinoidea

Child Taxonomies: Echinacea, Atelostomata, Calycina, Gnathostomata, Irregularia, Holasteroida, Acroechinoidea, unclassified Euechinoidea

Scopoletin

7-hydroxy-6-methoxy-2H-chromen-2-one

C10H8O4 (192.0422568)


Scopoletin is a hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. It has a role as a plant growth regulator and a plant metabolite. It is functionally related to an umbelliferone. Scopoletin is a natural product found in Ficus auriculata, Haplophyllum cappadocicum, and other organisms with data available. Scopoletin is a coumarin compound found in several plants including those in the genus Scopolia and the genus Brunfelsia, as well as chicory (Cichorium), redstem wormwood (Artemisia scoparia), stinging nettle (Urtica dioica), passion flower (Passiflora), noni (Morinda citrifolia fruit) and European black nightshade (Solanum nigrum) that is comprised of umbelliferone with a methoxy group substituent at position 6. Scopoletin is used to standardize and establish pharmacokinetic properties for products derived from the plants that produce it, such as noni extract. Although the mechanism(s) of action have not yet been established, this agent has potential antineoplastic, antidopaminergic, antioxidant, anti-inflammatory and anticholinesterase effects. Plant growth factor derived from the root of Scopolia carniolica or Scopolia japonica. See also: Arnica montana Flower (part of); Lycium barbarum fruit (part of); Viburnum opulus root (part of). Isolated from Angelica acutiloba (Dong Dang Gui). Scopoletin is found in many foods, some of which are lambsquarters, lemon, sunflower, and sherry. Scopoletin is found in anise. Scopoletin is isolated from Angelica acutiloba (Dong Dang Gui A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. Acquisition and generation of the data is financially supported in part by CREST/JST. [Raw Data] CBA72_Scopoletin_pos_20eV.txt [Raw Data] CBA72_Scopoletin_pos_40eV.txt [Raw Data] CBA72_Scopoletin_neg_30eV.txt [Raw Data] CBA72_Scopoletin_neg_50eV.txt [Raw Data] CBA72_Scopoletin_pos_50eV.txt [Raw Data] CBA72_Scopoletin_pos_10eV.txt [Raw Data] CBA72_Scopoletin_neg_40eV.txt [Raw Data] CBA72_Scopoletin_neg_10eV.txt [Raw Data] CBA72_Scopoletin_pos_30eV.txt [Raw Data] CBA72_Scopoletin_neg_20eV.txt Scopoletin. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=92-61-5 (retrieved 2024-07-12) (CAS RN: 92-61-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

Vanillic acid

4-hydroxy-3-methoxybenzoic 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].

   

Berberine

16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium

[C20H18NO4]+ (336.1235768)


Berberine is an organic heteropentacyclic compound, an alkaloid antibiotic, a botanical anti-fungal agent and a berberine alkaloid. It has a role as an antilipemic drug, a hypoglycemic agent, an antioxidant, a potassium channel blocker, an antineoplastic agent, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor, an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor, an EC 1.21.3.3 (reticuline oxidase) inhibitor, an EC 2.1.1.116 [3-hydroxy-N-methyl-(S)-coclaurine 4-O-methyltransferase] inhibitor, an EC 3.1.1.4 (phospholipase A2) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 2.7.11.10 (IkappaB kinase) inhibitor, an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor, a geroprotector and a metabolite. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. Berberine is a quaternary ammonia compound found in many botanical products, including goldenseal, barberry and Oregon grape, which is used for its purported antioxidant and antimicrobial properties for a host of conditions, including obesity, diabetes, hyperlipidemia, heart failure, H. pylori infection and colonic adenoma prevention. Berberine has not been linked to serum aminotransferase elevations during therapy nor to instances of clinically apparent liver injury. Berberine is a natural product found in Berberis poiretii, Thalictrum delavayi, and other organisms with data available. Berberine is a quaternary ammonium salt of an isoquinoline alkaloid and active component of various Chinese herbs, with potential antineoplastic, radiosensitizing, anti-inflammatory, anti-lipidemic and antidiabetic activities. Although the mechanisms of action through which berberine exerts its effects are not yet fully elucidated, upon administration this agent appears to suppress the activation of various proteins and/or modulate the expression of a variety of genes involved in tumorigenesis and inflammation, including, but not limited to transcription factor nuclear factor-kappa B (NF-kB), myeloid cell leukemia 1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), B-cell lymphoma-extra large (Bcl-xl), cyclooxygenase (COX)-2, tumor necrosis factor (TNF), interleukin (IL)-6, IL-12, inducible nitric oxide synthase (iNOS), intercellular adhesion molecule-1 (ICAM-1), E-selectin, monocyte chemoattractant protein-1 (MCP-1), C-X-C motif chemokine 2 (CXCL2), cyclin D1, activator protein (AP-1), hypoxia-inducible factor 1 (HIF-1), signal transducer and activator of transcription 3 (STAT3), peroxisome proliferator-activated receptor (PPAR), arylamine N-acetyltransferase (NAT), and DNA topoisomerase I and II. The modulation of gene expression may induce cell cycle arrest and apoptosis, and inhibit cancer cell proliferation. In addition, berberine modulates lipid and glucose metabolism. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. See also: Goldenseal (part of); Berberis aristata stem (part of). Berberine is a quaternary ammonium salt that belongs to the protoberberine group of benzylisoquinoline alkaloids. Chemically, berberine is classified as an isoquinoline alkaloid. More specifically, berberine is a plant alkaloid derived from tyrosine through a complex 8 step biosynthetic process. Berberine is found in plants such as Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape) and Hydrastis canadensis (goldenseal). Two other known berberine-containing plants are Phellodendron chinense and Phellodendron amurense. Berberine is usually found in the roots, rhizomes, stems, and bark of Berberis plants. Due to berberines intense yellow color, plants that contain berberine were traditionally used to dye wool, leather, and wood. Under ultraviolet light, berberine shows a strong yellow fluorescence, making it useful in histology for staining heparin in mast cells. Berberine is a bioactive plant compound that has been frequently used in traditional medicine. Among the known physiological effects or bioactivities are: 1) Antimicrobial action against bacteria, fungi, protozoa, viruses, helminthes, and Chlamydia; 2) Antagonism against the effects of cholera and E coli heat-stable enterotoxin; 3) Inhibition of intestinal ion secretion and of smooth muscle contraction; 4) Reduction of inflammation and 5) Stimulation of bile secretion and bilirubin discharge (PMID:32335802). Berberine can inhibit bacterial growth in the gut, including Helicobacter pylori, protect the intestinal epithelial barrier from injury, and ameliorate liver injury. Currently, berberine is sold as an Over-the-Counter (OTC) drug for treating gastrointestinal infections in China (PMID:18442638). Berberine also inhibits the proliferation of various types of cancer cells and impedes invasion and metastasis (PMID:32335802). Recent evidence has also confirmed that berberine improves the efficacy and safety of both chemo and radiotherapies for cancer treatment (PMID:32335802). Berberine has also been shown to regulate glucose and lipid metabolism in vitro and in vivo (PMID:18442638). In fact, berberine is the main active component of an ancient Chinese herb Coptis chinensis French, which has been used to treat diabetes for thousands of years. As an anti-diabetic, berberine increases glucose uptake by muscle fibers independent of insulin levels. It triggers AMPK activation and increases glycolysis, leading to decreased insulin resistance and decreased oxygen respiration. The same mechanism leads to a reduction in gluconeogenesis in the liver. AMPK activation by berberine also leads to an antiatherosclerotic effect in mice. Berberines AMPK activation may also underlie berberines anti-obesity effects and favorable influence on weight loss (PMID:18442638). While its use as a medication is widely touted, it is important to remember that berberine inhibits CYP2D6 and CYP3A4 enzymes, both of which are involved in the metabolism of many endogenous substances and xenobiotics, including a number of prescription drugs. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. [HMDB] COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials [Raw Data] CBA98_Berberine_pos_50eV.txt [Raw Data] CBA98_Berberine_pos_10eV.txt [Raw Data] CBA98_Berberine_pos_20eV.txt [Raw Data] CBA98_Berberine_pos_40eV.txt [Raw Data] CBA98_Berberine_pos_30eV.txt Berberine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=2086-83-1 (retrieved 2024-09-04) (CAS RN: 2086-83-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Vanillin

Vanillin melting point standard, Pharmaceutical Secondary Standard; Certified Reference Material

C8H8O3 (152.0473418)


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

   

Protocatechuic acid

3,4-dihydroxybenzoic 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.

   

linolenate(18:3)

(9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid

C18H30O2 (278.224568)


alpha-Linolenic acid (ALA) is a polyunsaturated fatty acid (PUFA). It is a member of the group of essential fatty acids called omega-3 fatty acids. alpha-Linolenic acid, in particular, is not synthesized by mammals and therefore is an essential dietary requirement for all mammals. Certain nuts (English walnuts) and vegetable oils (canola, soybean, flaxseed/linseed, olive) are particularly rich in alpha-linolenic acid. Omega-3 fatty acids get their name based on the location of one of their first double bond. In all omega-3 fatty acids, the first double bond is located between the third and fourth carbon atom counting from the methyl end of the fatty acid (n-3). Although humans and other mammals can synthesize saturated and some monounsaturated fatty acids from carbon groups in carbohydrates and proteins, they lack the enzymes necessary to insert a cis double bond at the n-6 or the n-3 position of a fatty acid. Omega-3 fatty acids like alpha-linolenic acid are important structural components of cell membranes. When incorporated into phospholipids, they affect cell membrane properties such as fluidity, flexibility, permeability, and the activity of membrane-bound enzymes. Omega-3 fatty acids can modulate the expression of a number of genes, including those involved with fatty acid metabolism and inflammation. alpha-Linolenic acid and other omega-3 fatty acids may regulate gene expression by interacting with specific transcription factors, including peroxisome proliferator-activated receptors (PPARs) and liver X receptors (LXRs). alpha-Linolenic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. α-Linolenic acid can be obtained by humans only through their diets. Humans lack the desaturase enzymes required for processing stearic acid into A-linoleic acid or other unsaturated fatty acids. Dietary α-linolenic acid is metabolized to stearidonic acid, a precursor to a collection of polyunsaturated 20-, 22-, 24-, etc fatty acids (eicosatetraenoic acid, eicosapentaenoic acid, docosapentaenoic acid, tetracosapentaenoic acid, 6,9,12,15,18,21-tetracosahexaenoic acid, docosahexaenoic acid).[12] Because the efficacy of n−3 long-chain polyunsaturated fatty acid (LC-PUFA) synthesis decreases down the cascade of α-linolenic acid conversion, DHA synthesis from α-linolenic acid is even more restricted than that of EPA.[13] Conversion of ALA to DHA is higher in women than in men.[14] α-Linolenic acid, also known as alpha-linolenic acid (ALA) (from Greek alpha meaning "first" and linon meaning flax), is an n−3, or omega-3, essential fatty acid. ALA is found in many seeds and oils, including flaxseed, walnuts, chia, hemp, and many common vegetable oils. In terms of its structure, it is named all-cis-9,12,15-octadecatrienoic acid.[2] In physiological literature, it is listed by its lipid number, 18:3 (n−3). It is a carboxylic acid with an 18-carbon chain and three cis double bonds. The first double bond is located at the third carbon from the methyl end of the fatty acid chain, known as the n end. Thus, α-linolenic acid is a polyunsaturated n−3 (omega-3) fatty acid. It is a regioisomer of gamma-linolenic acid (GLA), an 18:3 (n−6) fatty acid (i.e., a polyunsaturated omega-6 fatty acid with three double bonds). Alpha-linolenic acid is a linolenic acid with cis-double bonds at positions 9, 12 and 15. Shown to have an antithrombotic effect. It has a role as a micronutrient, a nutraceutical and a mouse metabolite. It is an omega-3 fatty acid and a linolenic acid. It is a conjugate acid of an alpha-linolenate and a (9Z,12Z,15Z)-octadeca-9,12,15-trienoate. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. alpha-Linolenic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Linolenic Acid is a natural product found in Prunus mume, Dipteryx lacunifera, and other organisms with data available. Linolenic Acid is an essential fatty acid belonging to the omega-3 fatty acids group. It is highly concentrated in certain plant oils and has been reported to inhibit the synthesis of prostaglandin resulting in reduced inflammation and prevention of certain chronic diseases. Alpha-linolenic acid (ALA) is a polyunsaturated omega-3 fatty acid. It is a component of many common vegetable oils and is important to human nutrition. A fatty acid that is found in plants and involved in the formation of prostaglandins. Seed oils are the richest sources of α-linolenic acid, notably those of hempseed, chia, perilla, flaxseed (linseed oil), rapeseed (canola), and soybeans. α-Linolenic acid is also obtained from the thylakoid membranes in the leaves of Pisum sativum (pea leaves).[3] Plant chloroplasts consisting of more than 95 percent of photosynthetic thylakoid membranes are highly fluid due to the large abundance of ALA, evident as sharp resonances in high-resolution carbon-13 NMR spectra.[4] Some studies state that ALA remains stable during processing and cooking.[5] However, other studies state that ALA might not be suitable for baking as it will polymerize with itself, a feature exploited in paint with transition metal catalysts. Some ALA may also oxidize at baking temperatures. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. Gamma-linolenic acid (γ-Linolenic acid) is an omega-6 (n-6), 18 carbon (18C-) polyunsaturated fatty acid (PUFA) extracted from Perilla frutescens. Gamma-linolenic acid supplements could restore needed PUFAs and mitigate the disease[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

   

Rutin

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one;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].

   

Chlorogenic acid

Chlorogenic acid (constituent of echinacea angustifolia root, echinacea pallida root, echinacea purpurea root and echinacea purpurea aerial parts)

C16H18O9 (354.0950778)


Chlorogenic acid is a cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin. It has a role as a plant metabolite and a food component. It is a cinnamate ester and a tannin. It is functionally related to a (-)-quinic acid and a trans-caffeic acid. It is a conjugate acid of a chlorogenate. Chlorogenic Acid has been used in trials studying the treatment of Advanced Cancer and Impaired Glucose Tolerance. Chlorogenic Acid is a natural product found in Pavetta indica, Fragaria nipponica, and other organisms with data available. Chlorogenic Acid is a polyphenol and the ester of caffeic acid and quinic acid that is found in coffee and black tea, with potential antioxidant and chemopreventive activities. Chlorogenic acid scavenges free radicals, which inhibits DNA damage and may protect against the induction of carcinogenesis. In addition, this agent may upregulate the expression of genes involved in the activation of the immune system and enhances activation and proliferation of cytotoxic T-lymphocytes, macrophages, and natural killer cells. Chlorogenic acid also inhibits the activity of matrix metalloproteinases. A naturally occurring phenolic acid which is a carcinogenic inhibitor. It has also been shown to prevent paraquat-induced oxidative stress in rats. (From J Chromatogr A 1996;741(2):223-31; Biosci Biotechnol Biochem 1996;60(5):765-68). See also: Arctium lappa Root (part of); Cynara scolymus leaf (part of); Lonicera japonica flower (part of) ... View More ... Chlorogenic acid is an ester of caffeic acid and quinic acid. Chlorogenic acid is the major polyphenolic compound in coffee, isolated from the leaves and fruits of dicotyledonous plants. This compound, long known as an antioxidant, also slows the release of glucose into the bloodstream after a meal. Coffee is a complex mixture of chemicals that provides significant amounts of chlorogenic acid. The chlorogenic acid content of a 200 ml (7-oz) cup of coffee has been reported to range from 70-350 mg, which would provide about 35-175 mg of caffeic acid. The results of epidemiological research suggest that coffee consumption may help prevent several chronic diseases, including type 2 diabetes mellitus, Parkinsons disease and liver disease (cirrhosis and hepatocellular carcinoma). Most prospective cohort studies have not found coffee consumption to be associated with significantly increased cardiovascular disease risk. However, coffee consumption is associated with increases in several cardiovascular disease risk factors, including blood pressure and plasma homocysteine. At present, there is little evidence that coffee consumption increases the risk of cancer. (PMID:16507475, 17368041). A cinnamate ester obtained by formal condensation of the carboxy group of trans-caffeic acid with the 3-hydroxy group of quinic acid. It is an intermediate metabolite in the biosynthesis of lignin. [Raw Data] CBA08_Chlorogenic-aci_pos_10eV_1-1_01_209.txt [Raw Data] CBA08_Chlorogenic-aci_neg_30eV_1-1_01_218.txt [Raw Data] CBA08_Chlorogenic-aci_neg_20eV_1-1_01_217.txt [Raw Data] CBA08_Chlorogenic-aci_pos_30eV_1-1_01_211.txt [Raw Data] CBA08_Chlorogenic-aci_neg_40eV_1-1_01_219.txt [Raw Data] CBA08_Chlorogenic-aci_pos_20eV_1-1_01_210.txt [Raw Data] CBA08_Chlorogenic-aci_pos_50eV_1-1_01_213.txt [Raw Data] CBA08_Chlorogenic-aci_neg_50eV_1-1_01_220.txt [Raw Data] CBA08_Chlorogenic-aci_neg_10eV_1-1_01_216.txt [Raw Data] CBA08_Chlorogenic-aci_pos_40eV_1-1_01_212.txt Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb. It is an orally active antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension compound[1][2][3]. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension.

   

Caffeic acid

(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoic 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).

   

Ferulic acid

(E)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoic acid

C10H10O4 (194.057906)


trans-Ferulic acid is a highly abundant phenolic phytochemical which is present in plant cell walls. Ferulic acid is a phenolic acid that can be absorbed by the small intestine and excreted through the urine. It is one of the most abundant phenolic acids in plants, varying from 5 g/kg in wheat bran to 9 g/kg in sugar-beet pulp and 50 g/kg in corn kernel. It occurs primarily in seeds and leaves both in its free form (albeit rarely) and covalently linked to lignin and other biopolymers. It is usually found as ester cross-links with polysaccharides in the cell wall, such as arabinoxylans in grasses, pectin in spinach and sugar beet, and xyloglucans in bamboo. It also can cross-link with proteins. Due to its phenolic nucleus and an extended side chain conjugation (carbohydrates and proteins), it readily forms a resonance-stabilized phenoxy radical which accounts for its potent antioxidant potential. Food supplementation with curcumin and ferulic acid is considered a nutritional approach to reducing oxidative damage and amyloid pathology in Alzheimer disease (PMID:17127365, 1398220, 15453708, 9878519). Ferulic acid can be found in Pseudomonas and Saccharomyces (PMID:8395165). Ferulic acid is a ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. It has a role as an antioxidant, a MALDI matrix material, a plant metabolite, an anti-inflammatory agent, an apoptosis inhibitor and a cardioprotective agent. It is a conjugate acid of a ferulate. Ferulic acid is a natural product found in Haplophyllum griffithianum, Visnea mocanera, and other organisms with data available. Ferulic acid is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Angelica sinensis root (part of). Widely distributed in plants, first isolated from Ferula foetida (asafoetida). Antioxidant used to inhibit oxidn. of fats, pastry products, etc. Antifungal agent used to prevent fruit spoilage. trans-Ferulic acid is found in many foods, some of which are deerberry, peach, shea tree, and common bean. A ferulic acid consisting of trans-cinnamic acid bearing methoxy and hydroxy substituents at positions 3 and 4 respectively on the phenyl ring. D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D005765 - Gastrointestinal Agents > D002756 - Cholagogues and Choleretics D002317 - Cardiovascular Agents > D000959 - Antihypertensive Agents D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents D002491 - Central Nervous System Agents > D000700 - Analgesics D000975 - Antioxidants > D016166 - Free Radical Scavengers D006401 - Hematologic Agents > D000925 - Anticoagulants D020011 - Protective Agents > D000975 - Antioxidants D000893 - Anti-Inflammatory Agents D018501 - Antirheumatic Agents Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID H074 (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

   

Scopolin

6-methoxy-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-2-one

C16H18O9 (354.0950778)


Scopolin is a member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a monosaccharide derivative, a member of coumarins and a beta-D-glucoside. It is functionally related to a scopoletin. Scopolin is a natural product found in Artemisia ordosica, Astragalus onobrychis, and other organisms with data available. See also: Chamaemelum nobile flower (part of). A member of the class of coumarins that is scopoletin attached to a beta-D-glucopyranosyl residue at position 7 via a glycosidic linkage. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2].

   

4-Hydroxybenzoic acid

4-hydroxybenzoic acid

C7H6O3 (138.03169259999999)


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

   

Coniferin

(2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-(4-((E)-3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy)tetrahydro-2H-pyran-3,4,5-triol

C16H22O8 (342.1314612)


Coniferin (CAS: 531-29-3), also known as abietin or coniferoside, belongs to the class of organic compounds known as phenolic glycosides. These are organic compounds containing a phenolic structure attached to a glycosyl moiety. Some examples of phenolic structures include lignans and flavonoids. Among the sugar units found in natural glycosides are D-glucose, L-fructose, and L-rhamnose. Coniferin is an extremely weak basic (essentially neutral) compound (based on its pKa). Coniferin is a monosaccharide derivative consisting of coniferol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. Coniferin is found in asparagus and has been isolated from Scorzonera hispanica (black salsify). Coniferin is a monosaccharide derivative that is coniferol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. It has a role as a plant metabolite. It is a cinnamyl alcohol beta-D-glucoside, an aromatic ether and a monosaccharide derivative. It is functionally related to a coniferol. Coniferin is a natural product found in Salacia chinensis, Astragalus onobrychis, and other organisms with data available. A monosaccharide derivative that is coniferol attached to a beta-D-glucopyranosyl residue at position 1 via a glycosidic linkage. Isolated from Scorzonera hispanica (scorzonera) Coniferin (Laricin) is a glucoside of coniferyl alcohol. Coniferin inhibits fungal growth and melanization[1]. Coniferin (Laricin) is a glucoside of coniferyl alcohol. Coniferin inhibits fungal growth and melanization[1].

   

Coniferyl alcohol

2-PROPEN-1-OL, 3-(4-HYDROXY-3-METHOXYPHENYL)-, (E)-

C10H12O3 (180.0786402)


Coniferyl alcohol (CAS: 458-35-5), also known as coniferol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Coniferyl alcohol is an organic compound. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. Coniferyl alcohol is an intermediate in the biosynthesis of eugenol, stilbenoids, and coumarin. Outside of the human body, coniferyl alcohol has been detected, but not quantified in, several different foods, such as common sages, chestnuts, cereals and cereal products, gingers, and cashew nuts. This could make coniferyl alcohol a potential biomarker for the consumption of these foods. Gum benzoin contains a significant amount of coniferyl alcohol and its esters. Coniferyl alcohol is an organic compound. This colourless crystalline solid is a phytochemical, one of the monolignols. It is synthesized via the phenylpropanoid biochemical pathway. Coniferol is a phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring. It has a role as a monolignol, a mouse metabolite, a pheromone, an animal metabolite, a plant metabolite and a volatile oil component. It is a phenylpropanoid and a member of guaiacols. It is functionally related to an (E)-cinnamyl alcohol. Coniferyl alcohol is a natural product found in Asparagus cochinchinensis, Xanthium spinosum, and other organisms with data available. See also: Polignate Sodium (monomer of); Ammonium lignosulfonate (monomer of); Calcium lignosulfonate (50000 MW) (monomer of) ... View More ... Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbene and coumarin. Gum benzoin contains significant amount of coniferyl alcohol and its esters.; Coniferyl alcohol is an organic compound. This colourless crystalline solid is a phytochemical, one of the monolignols. It is synthetized via the phenylpropanoid biochemical pathway. When copolymerized with related aromatic compounds, coniferyl alcohol forms lignin or lignans. [HMDB]. Coniferyl alcohol is found in many foods, some of which are canada blueberry, eggplant, winged bean, and flaxseed. A phenylpropanoid that is one of the main monolignols, produced by the reduction of the carboxy functional group in cinnamic acid and the addition of a hydroxy and a methoxy substituent to the aromatic ring. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin[1]. Coniferyl alcohol specifically inhibits fungal growth[1]. Coniferyl alcohol is an intermediate in biosynthesis of eugenol and of stilbenoids and coumarin[1]. Coniferyl alcohol specifically inhibits fungal growth[1].

   

Nonacosane

Nonacosane; Celidoniol, deoxy- (7CI); n-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].

   

beta-D-Galactopyranosyl-(1->4)-beta-D-galactopyranosyl-(1->4)-D-galactose

2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C18H32O16 (504.1690272)


beta-D-Galactopyranosyl-(1->4)-beta-D-galactopyranosyl-(1->4)-D-galactose, also known as b-D-galactopyranosyl-(1->4)-b-D-galactopyranosyl-(1->4)-D-galactose belongs to the class of organic compounds known as oligosaccharides or glycans. These are carbohydrates made up of 3 to 10 monosaccharide units linked to each other through glycosidic bonds. beta-D-galactopyranosyl-(1->4)-beta-D-galactopyranosyl-(1->4)-D-galactose has been detected, but not quantified, in root vegetables. Beta-D-Galactopyranosyl-(1->4)-beta-D-galactopyranosyl-(1->4)-D-galactose is an oligosaccharide. Maltotriose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Maltotriose is a natural product found in Lycium barbarum, Polygonum aviculare, and other organisms with data available. Maltotriose is a metabolite found in or produced by Saccharomyces cerevisiae. Maltotriose, the second most abundant sugar present in brewing, is an inducer of the maltose regulon of Escherichia coli. Maltotriose can induce beta-galactosidase synthesis[1][2]. Maltotriose, the second most abundant sugar present in brewing, is an inducer of the maltose regulon of Escherichia coli. Maltotriose can induce beta-galactosidase synthesis[1][2].

   

Palmitoleic acid

cis-Delta(9)-Hexadecenoic acid

C16H30O2 (254.224568)


Cis-9-palmitoleic acid, also known as palmitoleate or (Z)-9-hexadecenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, cis-9-palmitoleic acid is considered to be a fatty acid lipid molecule. Cis-9-palmitoleic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-9-palmitoleic acid can be found in a number of food items such as mixed nuts, carrot, hedge mustard, and chanterelle, which makes cis-9-palmitoleic acid a potential biomarker for the consumption of these food products. Cis-9-palmitoleic acid can be found primarily in most biofluids, including urine, blood, saliva, and feces, as well as in human adipose tissue, prostate and skeletal muscle tissues. Cis-9-palmitoleic acid exists in all living species, ranging from bacteria to humans. Moreover, cis-9-palmitoleic acid is found to be associated with isovaleric acidemia. Palmitoleic acid, or (9Z)-hexadec-9-enoic acid, is an omega-7 monounsaturated fatty acid (16:1n-7) with the formula CH3(CH2)5CH=CH(CH2)7COOH that is a common constituent of the glycerides of human adipose tissue. Present in all tissues, it is generally found in higher concentrations in the liver. Macadamia oil (Macadamia integrifolia) and sea buckthorn oil (Hippophae rhamnoides) are botanical sources of palmitoleic acid, containing 22 and 40\\\\\% respectively. Palmitoleic acid is found to be associated with isovaleric acidemia, which is an inborn error of metabolism. Palmitoleic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=373-49-9 (retrieved 2024-07-15) (CAS RN: 373-49-9). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats. Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.

   

Syringic acid

InChI=1/C9H10O5/c1-13-6-3-5(9(11)12)4-7(14-2)8(6)10/h3-4,10H,1-2H3,(H,11,12

C9H10O5 (198.052821)


Syringic acid, also known as syringate or cedar acid, belongs to the class of organic compounds known as gallic acid and derivatives. Gallic acid and derivatives are compounds containing a 3,4,5-trihydroxybenzoic acid moiety. Outside of the human body, Syringic acid is found, on average, in the highest concentration within a few different foods, such as common walnuts, swiss chards, and olives and in a lower concentration in apples, tarragons, and peanuts. Syringic acid has also been detected, but not quantified in several different foods, such as sweet marjorams, silver lindens, bulgurs, annual wild rices, and barley. This could make syringic acid a potential biomarker for the consumption of these foods. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Research suggests that phenolics from wine may play a positive role against oxidation of low-density lipoprotein (LDL), which is a key step in the development of atherosclerosis. Syringic acid is a phenol present in some distilled alcohol beverages. It is also a product of microbial (gut) metabolism of anthocyanins and other polyphenols that have been consumed (in fruits and alcoholic beverages - PMID:18767860). Syringic acid is also a microbial metabolite that can be found in Bifidobacterium (PMID:24958563). Syringic acid is a dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. It has a role as a plant metabolite. It is a member of benzoic acids, a dimethoxybenzene and a member of phenols. It is functionally related to a gallic acid. It is a conjugate acid of a syringate. Syringic acid is a natural product found in Visnea mocanera, Pittosporum illicioides, and other organisms with data available. Syringic acid is a metabolite found in or produced by Saccharomyces cerevisiae. Present in various plants free and combined, e.g. principal phenolic constituent of soyabean meal (Glycine max) A dimethoxybenzene that is 3,5-dimethyl ether derivative of gallic acid. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents KEIO_ID S018 Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation.

   

Hydrastine

3-((5R)-6-methyl(5,6,7,8-tetrahydro-2H-1,3-dioxoleno[4,5-g]isoquinolin-5-yl))( 3S)-6,7-dimethoxy-3-hydroisobenzofuran-1-one

C21H21NO6 (383.13688060000004)


Hydrastine is a member of isoquinolines. It has a role as a metabolite. Hydrastine is a natural product found in Hydrastis canadensis, Fumaria indica, and other organisms with data available. See also: Goldenseal (part of). A natural product found in Hydrastis canadensis. Origin: Plant; SubCategory_DNP: Isoquinoline alkaloids, Benzylisoquinoline alkaloids relative retention time with respect to 9-anthracene Carboxylic Acid is 0.582 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.578 Hydrastine is a natural alkaloid which is present in Hydrastis canadensis and other plants of the ranunculaceae family.

   

Picein

1-(4-(((2S,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethanone

C14H18O7 (298.10524780000003)


Picein is a glycoside. Picein is a natural product found in Salix candida, Halocarpus biformis, and other organisms with data available. Picein, isolated from Picrorhiza kurroa, is a naturally occurring antioxidant[1]. Picein, isolated from Picrorhiza kurroa, is a naturally occurring antioxidant[1].

   

echinacoside

echinacoside

C35H46O20 (786.2582316)


Echinacoside, one of the phenylethanoids isolated from the stems of Cistanche deserticola, effectively inhibits Wnt/β-catenin signaling. Echinacoside elicits neuroprotection by activating Trk receptors and their downstream signal pathways. Antiosteoporotic activity[1][2][3]. Echinacoside, one of the phenylethanoids isolated from the stems of Cistanche deserticola, effectively inhibits Wnt/β-catenin signaling. Echinacoside elicits neuroprotection by activating Trk receptors and their downstream signal pathways. Antiosteoporotic activity[1][2][3].

   

Hentriacontane

N-Hentriacontane

C31H64 (436.5007744)


Hentriacontane is found in black elderberry. Hentriacontane, also called untriacontane, is a solid, long-chain alkane hydrocarbon with the structural formula CH3(CH2)29CH3. It is found in a variety of plants, including peas (pisum sativum), gum arabic (acacia senegal) and others, and also comprises about 8-9\\% of beeswax. It has 10,660,307,791 constitutional isomers Hentriacontane, also called untriacontane, is a solid, long-chain alkane hydrocarbon with the structural formula CH3(CH2)29CH3. It is found in a variety of plants, including peas (pisum sativum), gum arabic (acacia senegal) and others, and also comprises about 8-9\\% of beeswax. It has 10,660,307,791 constitutional isomers.

   

Tritriacontane

N-tritriacontane

C33H68 (464.5320728)


Tritriacontane 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, tritriacontane is considered to be a hydrocarbon lipid molecule. Tritriacontane can be found in cardamom, garden tomato (variety), and papaya, which makes tritriacontane 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 . Tritriacontane, also known as CH3-[CH2]31-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, tritriacontane is a hydrocarbon lipid molecule that is very hydrophobic, practically insoluble in water, and relatively neutral. Tritriacontane has been detected in cardamoms, garden tomato (var.), and papaya. This could make tritriacontane a potential biomarker for the consumption of these foods. Tritriacontane is also found in Medicago arabica (PMID: 17793563).

   

Danielone

2-hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)ethan-1-one

C10H12O5 (212.06847019999998)


Phytoalexin isolated from the fruits of papaya (Carica papaya). Danielone is found in papaya and fruits. Danielone is found in fruits. Phytoalexin isolated from the fruits of papaya (Carica papaya

   

Tricosane

CH3-[CH2]21-CH3

C23H48 (324.37558079999997)


N-tricosane, also known as ch3-[ch2]21-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, N-tricosane is considered to be a hydrocarbon lipid molecule. N-tricosane is an alkane and waxy tasting compound and can be found in a number of food items such as kohlrabi, papaya, coconut, and ginkgo nuts, which makes N-tricosane a potential biomarker for the consumption of these food products. N-tricosane can be found primarily in saliva. 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 . Tricosane belongs to the class of organic compounds known as acyclic alkanes. These are acyclic hydrocarbons consisting only of n carbon atoms and m hydrogen atoms where m=2*n + 2.

   

β-Pinene

(1S,5S)-7,7-dimethyl-4-methylidene-bicyclo[3.1.1]heptane

C10H16 (136.1251936)


An isomer of pinene with an exocyclic double bond. It is a component of essential oils from many plants. Widely distributed in plants, usually associated with a-Pinene JPV84-W but in smaller amounts. Found in lime peel oil, ginger, nutmeg, mace, bitter fennel, rosemary and sage. Flavour ingredient β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2]. β-Pinene ((-)-β-Pinene), a major component of turpentine, inhibit infectious bronchitis virus (IBV) with an IC50 of 1.32 mM. β-Pinene presents antimicrobial activity[1][2].

   

HEPTACOSANE

HEPTACOSANE

C27H56 (380.4381776)


A straight-chain alkane with 27 carbon atoms.

   

Caftaric acid

Butanedioic acid, 2-[[(2E)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3-hydroxy-, (2R,3R)- (9CI); Butanedioic acid, 2-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-3-hydroxy-, [R-[R*,R*-(E)]]-; (2R,3R)-2-[[(2E)-3-(3,4-Dihydroxyphenyl)-1-oxo-2-propen-1-yl]oxy]-3-hydroxybutanedioic acid; trans-Caftaric acid

C13H12O9 (312.0481302)


Caftaric acid is a hydroxycinnamic acid. Caftaric acid is a natural product found in Vitis rotundifolia, Vitis cinerea var. helleri, and other organisms with data available. Caftaric acid is a metabolite found in or produced by Saccharomyces cerevisiae. Caftaric acid is a non-flavanoid that impacts the color of white wine. Many believe this molecule is responsible for the yellowish-gold color seen in some whites wines[citation needed]. Aside from wine, it is abundantly present in raisins. Caftaric acid is a natural compound. Caftaric acid is a natural compound.

   

Pentacosane

2A4605C9-A088-458C-AD58-AA987FF6C408

C25H52 (352.4068792)


Constituent of many naturally occurring waxes. A colorless solid at ambient conditions. Pentacosane is an alkane consisting of an unbranched chain of 25 carbon atoms. It has a role as a semiochemical and a plant metabolite. Pentacosane is a natural product found in Cryptotermes brevis, Erucaria microcarpa, and other organisms with data available. See also: Moringa oleifera leaf oil (part of). An alkane consisting of an unbranched chain of 25 carbon atoms. Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1]. Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1].

   

Docosane

InChI=1/C22H46/c1-3-5-7-9-11-13-15-17-19-21-22-20-18-16-14-12-10-8-6-4-2/h3-22H2,1-2H

C22H46 (310.3599316)


N-docosane, also known as ch3-[ch2]20-ch3 or dokosan, 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, N-docosane is considered to be a hydrocarbon lipid molecule. N-docosane is an alkane and waxy tasting compound and can be found in a number of food items such as lemon balm, linden, allspice, and sunflower, which makes N-docosane a potential biomarker for the consumption of these food products. N-docosane can be found primarily in saliva. 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 . Docosane, also known as CH3-[CH2]20-CH3 or dokosan, 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. Docosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, docosane is considered to be a hydrocarbon lipid molecule. Docosane is an alkane and waxy tasting compound. Docosane is found, on average, in the highest concentration within lemon balms. Docosane has also been detected, but not quantified, in several different foods, such as allspices, lindens, papaya, and sunflowers. This could make docosane a potential biomarker for the consumption of these foods. A straight-chain alkane with 22 carbon atoms. N-docosane is a solid. Insoluble in water. Used in organic synthesis, calibration, and temperature sensing equipment. Docosane is a straight-chain alkane with 22 carbon atoms. It has a role as a plant metabolite. Docosane is a natural product found in Lonicera japonica, Erucaria microcarpa, and other organisms with data available. See also: Moringa oleifera leaf oil (part of). A straight-chain alkane with 22 carbon atoms. Docosane, a straight chain alkane, can be used to synthesize structural composites with thermal energy storage/release capability[1][2]. Docosane, a straight chain alkane, can be used to synthesize structural composites with thermal energy storage/release capability[1][2].

   

2-Tridecanone

Dimethoxy methyldopa hydrochloride(DMMD)

C13H26O (198.1983546)


2-tridecanone is a white crystalline solid. (NTP, 1992) Tridecan-2-one is a methyl ketone that is tridecane in which the methylene hydrogens at position 2 are replaced by an oxo group. It has a role as a plant metabolite and a flavouring agent. It derives from a hydride of a tridecane. 2-Tridecanone is a natural product found in Hedychium spicatum, Azadirachta indica, and other organisms with data available. 2-Tridecanone is found in citrus. 2-Tridecanone is isolated from plant oils, e.g. palm oil, coconut oil. Also found in American cranberry, rabbiteye, blueberry, raspberry, grapefruit, onion, ginger and cheeses. 2-Tridecanone is used as a flavouring essence. Isolated from plant oils, e.g. palm oil, coconut oiland is also found in American cranberry, rabbiteye, blueberry, raspberry, grapefruit, onion, ginger and cheeses. It is used as a flavouring essence. A methyl ketone that is tridecane in which the methylene hydrogens at position 2 are replaced by an oxo group. 2-Tridecanone, a nonalkaloid insecticide, is isolated from the wild tomato Lycopersicon hirsutum f. glabratum. 2-Tridecanone is a volatile organic compound[1][2]. 2-Tridecanone, a nonalkaloid insecticide, is isolated from the wild tomato Lycopersicon hirsutum f. glabratum. 2-Tridecanone is a volatile organic compound[1][2].

   

Heneicosane

(S)-(-)-2,2-Bis(diphenylphosphino)-5,5,6,6,7,7,8,8-octahydro-1,1-binaphthyl (R)-H8-BINAP

C21H44 (296.3442824)


Heneicosane, also known as CH3-[CH2]19-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. Thus, heneicosane is considered to be a hydrocarbon lipid molecule. Heneicosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Heneicosane is an alkane and waxy tasting compound. Heneicosane is found, on average, in the highest concentration within a few different foods, such as black elderberries, common oregano, and lemon balms. Heneicosane has also been detected, but not quantified, in several different foods, such as sunflowers, kohlrabis, orange bell peppers, lindens, and pepper (c. annuum). This could make heneicosane a potential biomarker for the consumption of these foods. An alkane that has 21 carbons and a straight-chain structure. Heneicosane, also known as ch3-[ch2]19-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, heneicosane is considered to be a hydrocarbon lipid molecule. Heneicosane is an alkane and waxy tasting compound and can be found in a number of food items such as orange bell pepper, yellow bell pepper, lemon balm, and pepper (c. annuum), which makes heneicosane a potential biomarker for the consumption of these food products. Heneicosane can be found primarily in saliva. 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 . Crystals. (NTP, 1992) Henicosane is an alkane that has 21 carbons and a straight-chain structure. It has been isolated from plants like Periploca laevigata and Carthamus tinctorius. It has a role as a pheromone, a plant metabolite and a volatile oil component. Heneicosane is a natural product found in Erucaria microcarpa, Microcystis aeruginosa, and other organisms with data available. See also: Moringa oleifera leaf oil (part of). An alkane that has 21 carbons and a straight-chain structure. It has been isolated from plants like Periploca laevigata and Carthamus tinctorius. Heneicosane is an aroma component isolated from Streptomyces philanthi RL-1-178 or Serapias cordigera. Heneicosane is a pheromone and inhibits aflatoxin production[1][2][3]. Heneicosane is an aroma component isolated from Streptomyces philanthi RL-1-178 or Serapias cordigera. Heneicosane is a pheromone and inhibits aflatoxin production[1][2][3].

   

2-Pentadecanone

Methyl tridecyl ketone

C15H30O (226.22965299999998)


2-Pentadecanone is found in cereals and cereal products. 2-Pentadecanone is isolated from hop (Humulus lupulus), coconut (Cocos nucifera) and other oils. Also found in American cranberry, feijoa fruit, quince, asparagus, ginger, wheat bread, soybean, cooked rice and cheeses. 2-Pentadecanone is a flavouring ingredien Isolated from hop (Humulus lupulus), coconut (Cocos nucifera) and other oilsand is also found in American cranberry, feijoa fruit, quince, asparagus, ginger, wheat bread, soybean, cooked rice and cheeses. Flavouring ingredient.

   

Octacosane

CH3-[CH2]26-CH3

C28H58 (394.4538268)


Octacosane, also known as ch3-[ch2]26-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, octacosane is considered to be a hydrocarbon lipid molecule. Octacosane can be found in a number of food items such as peach, linden, apple, and carrot, which makes octacosane a potential biomarker for the consumption of these food products. Octacosane can be found primarily in saliva. 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 . Octacosane, also known as CH3-[CH2]26-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. Octacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, octacosane is considered to be a hydrocarbon lipid molecule. Octacosane has been detected, but not quantified, in several different foods, such as peachs, coconuts, apples, sweet cherries, and lindens. This could make octacosane a potential biomarker for the consumption of these foods. A straight-chain alkane containing 28 carbon atoms.

   

Hexacosane

CH3-[CH2]24-CH3

C26H54 (366.4225284)


Hexacosane, also known as ch3-[ch2]24-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, hexacosane is considered to be a hydrocarbon lipid molecule. Hexacosane can be found in a number of food items such as black elderberry, sunflower, papaya, and sweet cherry, which makes hexacosane a potential biomarker for the consumption of these food products. Hexacosane can be found primarily in saliva. 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 . Hexacosane, also known as CH3-[CH2]24-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. Thus, hexacosane is considered to be a hydrocarbon lipid molecule. Hexacosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Hexacosane has been detected, but not quantified, in several different foods, such as peachs, sunflowers, parsnips, coconuts, and papaya. This could make hexacosane a potential biomarker for the consumption of these foods. A straight-chain alkane comprising of 26 carbon atoms.

   

methyl 3-(4-hydroxyphenyl)prop-2-enoate

methyl 3-(4-hydroxyphenyl)prop-2-enoate

C10H10O3 (178.062991)


   

1-Pentadecene

Pentadec-1-ene

C15H30 (210.234738)


1-Pentadecene, also known as pentadec-1-ene, belongs to the class of organic compounds known as unsaturated aliphatic hydrocarbons. These are aliphatic Hydrocarbons that contains one or more unsaturated carbon atoms. 1-Pentadecene is an unbranched fifteen-carbon alkene with one double bond between C-1 and C-2. These compounds contain one or more double or triple bonds. Thus, 1-pentadecene is considered to be a hydrocarbon lipid molecule. 1-Pentadecene is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. 1-Pentadecene is found, on average, in the highest concentration within safflowers. 1-Pentadecene has also been detected, but not quantified, in burdocks and watermelons. This could make 1-pentadecene a potential biomarker for the consumption of these foods. Occurs in beef and oakmoss oleoresin. 1-Pentadecene is found in many foods, some of which are animal foods, burdock, safflower, and watermelon.

   

Nonadecane

Unknown branched fragment OF phospholipid

C19H40 (268.31298400000003)


Nonadecane, also known as CH3-[CH2]17-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. Nonadecane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, nonadecane is considered to be a hydrocarbon lipid molecule. Nonadecane is an alkane and bland tasting compound. nonadecane has been detected, but not quantified, in several different foods, such as pomes, watermelons, yellow bell peppers, allspices, and papaya. This could make nonadecane a potential biomarker for the consumption of these foods. Nonadecane has been linked to the inborn metabolic disorders including celiac disease. Isolated from apple wax. Nonadecane is found in many foods, some of which are pepper (c. annuum), red bell pepper, papaya, and dill.

   

Eicosane

CH3-[CH2]18-CH3

C20H42 (282.3286332)


Eicosane, also known as ch3-[ch2]18-ch3 or octyldodecane, 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, eicosane is considered to be a hydrocarbon lipid molecule. Eicosane is an alkane and waxy tasting compound and can be found in a number of food items such as linden, papaya, dill, and lemon balm, which makes eicosane a potential biomarker for the consumption of these food products. Eicosane can be found primarily in feces and saliva. Icosanes size, state or chemical inactivity does not exclude it from the traits its smaller alkane counterparts have. It is a colorless, non-polar molecule, nearly unreactive except when it burns. It is less dense than and insoluble in water. Its non-polar trait means it can only perform weak intermolecular bonding (hydrophobic/van der Waals forces) . Eicosane, also known as CH3-[CH2]18-CH3 or octyldodecane, 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. Eicosane is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Thus, eicosane is considered to be a hydrocarbon lipid molecule. Eicosane is an alkane and waxy tasting compound. Eicosane is found, on average, in the highest concentration within lemon balms. Eicosane has also been detected, but not quantified, in several different foods, such as allspices, papaya, coconuts, lindens, and hyssops. This could make eicosane a potential biomarker for the consumption of these foods. These are acyclic hydrocarbons consisting only of n carbon atoms and m hydrogen atoms where m=2*n + 2.

   

Dotriacontane

CH3-[CH2]30-CH3

C32H66 (450.5164236)


Constituent of Mentha aquatica (water mint). Dotriacontane is found in many foods, some of which are papaya, coconut, garden tomato (variety), and tea. Dotriacontane is found in coconut. Dotriacontane is a constituent of Mentha aquatica (water mint).

   

Listrocol

1,4-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid

C25H24O12 (516.1267703999999)


   

Echinacoside

6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C35H46O20 (786.2582316)


   

Hydrastine

6,7-dimethoxy-3-{6-methyl-2H,5H,6H,7H,8H-[1,3]dioxolo[4,5-g]isoquinolin-5-yl}-1,3-dihydro-2-benzofuran-1-one

C21H21NO6 (383.13688060000004)


   

Quercetin-3-o-rutinose

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

C27H30O16 (610.153378)


   

Verbascoside

6-[2-(3,4-Dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-3-yl 3-(3,4-dihydroxyphenyl)prop-2-enoic acid

C29H36O15 (624.2054106)


   

Heptacosane

CH3-[CH2]25-CH3

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 .

   

4-Hydroxybenzoyl glucose

(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4-hydroxybenzoate

C13H16O8 (300.0845136)


4-hydroxybenzoyl glucose, also known as 1-O-P-hydroxybenzoyl-β-D-glucose, is a member of the class of compounds known as hexoses. Hexoses are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. 4-hydroxybenzoyl glucose is soluble (in water) and a very weakly acidic compound (based on its pKa). 4-hydroxybenzoyl glucose can be found in common thyme, which makes 4-hydroxybenzoyl glucose a potential biomarker for the consumption of this food product.

   

Scopolin

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

C16H18O9 (354.0950778)


Scopolin is a member of the class of compounds known as coumarin glycosides. Coumarin glycosides are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Scopolin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Scopolin can be found in a number of food items such as sweet potato, oat, wild celery, and potato, which makes scopolin a potential biomarker for the consumption of these food products. Scopolin is a glucoside of scopoletin formed by the action of the enzyme scopoletin glucosyltransferase . Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2]. Scopolin is a coumarin isolated from Arabidopsis thaliana (Arabidopsis) roots[1]. Scopolin attenuated hepatic steatosis through activation of SIRT1-mediated signaling cascades[2].

   

Verbascoside

[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C29H36O15 (624.2054106)


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

   

Echinacoside

[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C35H46O20 (786.2582316)


Echinacoside is an oligosaccharide. Echinacoside is a phenylethanoid glycoside isolated from Echinacea angustifolia in 1950, and currently being investigated for the treatment of Parkinsons, Alzheimers, atherosclerosis, osteoporosis, acute colitis, wound treatment, and hepatitis. Echinacoside has demonstrated inhibition of apoptosis in neural cell lines, demonstrating potential for use in the treatment of neurological conditions. Echinacoside is a natural product found in Jasminum mesnyi, Pedicularis plicata, and other organisms with data available. Echinacoside, one of the phenylethanoids isolated from the stems of Cistanche deserticola, effectively inhibits Wnt/β-catenin signaling. Echinacoside elicits neuroprotection by activating Trk receptors and their downstream signal pathways. Antiosteoporotic activity[1][2][3]. Echinacoside, one of the phenylethanoids isolated from the stems of Cistanche deserticola, effectively inhibits Wnt/β-catenin signaling. Echinacoside elicits neuroprotection by activating Trk receptors and their downstream signal pathways. Antiosteoporotic activity[1][2][3].

   

9-Hexadecenoic acid

Hexadec-9-enoic acid

C16H30O2 (254.224568)


   

Vanillin

4-hydroxy-3-methoxybenzaldehyde

C8H8O3 (152.0473418)


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

   

Chlorogenic Acid

Malonyl-caffeoylquinic acid

C16H18O9 (354.0950778)


IPB_RECORD: 1901; CONFIDENCE confident structure Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb. It is an orally active antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension compound[1][2][3]. Chlorogenic acid is a major phenolic compound in Lonicera japonica Thunb.. It plays several important and therapeutic roles such as antioxidant activity, antibacterial, hepatoprotective, cardioprotective, anti-inflammatory, antipyretic, neuroprotective, anti-obesity, antiviral, anti-microbial, anti-hypertension.

   

PENTADECA-8,11-DIEN-2-ONE

PENTADECA-8,11-DIEN-2-ONE

C15H26O (222.1983546)


   

Rutin

2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-2-tetrahydropyranyl]oxymethyl]-2-tetrahydropyranyl]oxy]-4-chromenone

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].

   

12-hydroxyheptadeca-8,10,14-trienoic acid

12-hydroxyheptadeca-8,10,14-trienoic acid

C17H28O3 (280.2038338)


   

TRIACONTANE

TRIACONTANE

C30H62 (422.48512519999997)


A straight-chain alkane with 30 carbon atoms.

   

Pentacosane

EINECS 211-123-6

C25H52 (352.4068792)


Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1]. Pentacosane is one of the major components in the acetone extract from Curcuma raktakanda and is also in the essential oil from the leaves of Malus domestica. Pentacosane exhibit anti-cancer activities[1].

   

Berberine

Berberine

[C20H18NO4]+ (336.1235768)


Origin: Plant; SubCategory_DNP: Isoquinoline alkaloids, Benzylisoquinoline alkaloids COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2521; CONFIDENCE confident structure IPB_RECORD: 821; CONFIDENCE confident structure

   

Scopoletin

Scopoletin

C10H8O4 (192.0422568)


relative retention time with respect to 9-anthracene Carboxylic Acid is 0.636 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.637 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.629 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.631 IPB_RECORD: 1582; CONFIDENCE confident structure Scopoletin is an inhibitor of acetylcholinesterase (AChE). Scopoletin is an inhibitor of acetylcholinesterase (AChE).

   

4-hydroxybenzoate

4-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)


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

   

Ferulic acid

4-hydroxy-3-methoxycinnamic acid

C10H10O4 (194.057906)


(E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. (E)-Ferulic acid is a isomer of Ferulic acid which is an aromatic compound, abundant in plant cell walls. (E)-Ferulic acid causes the phosphorylation of β-catenin, resulting in proteasomal degradation of β-catenin and increases the expression of pro-apoptotic factor Bax and decreases the expression of pro-survival factor survivin. (E)-Ferulic acid shows a potent ability to remove reactive oxygen species (ROS) and inhibits lipid peroxidation. (E)-Ferulic acid exerts both anti-proliferation and anti-migration effects in the human lung cancer cell line H1299[1]. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively. Ferulic acid is a novel fibroblast growth factor receptor 1 (FGFR1) inhibitor with IC50s of 3.78 and 12.5 μM for FGFR1 and FGFR2, respectively.

   

Vanillic Acid

Vanillic acid hexoside

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].

   

Palmitoleic acid

Trans-Hexa-dec-2-enoic acid

C16H30O2 (254.224568)


A hexadec-9-enoic acid in which the double bond at position C-9 has cis configuration. In humans fatty acids are predominantly formed in the liver and adipose tissue, and mammary glands during lactation. Trans-hexa-dec-2-enoic acid is an intermediate in fatty acid biosynthesis. Specifically, trans-hexa-dec-2-enoic acid converted from (R)-3-Hydroxy-hexadecanoic acid via two enzymes; fatty-acid Synthase and 3- Hydroxypalmitoyl- [acyl-carrier-protein] dehydratase (EC: 2.3.1.85 and EC: 4.2.1.61). [HMDB] Cis-9-palmitoleic acid, also known as palmitoleate or (Z)-9-hexadecenoic acid, is a member of the class of compounds known as long-chain fatty acids. Long-chain fatty acids are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Thus, cis-9-palmitoleic acid is considered to be a fatty acid lipid molecule. Cis-9-palmitoleic acid is practically insoluble (in water) and a weakly acidic compound (based on its pKa). Cis-9-palmitoleic acid can be found in a number of food items such as red huckleberry, highbush blueberry, butternut, and macadamia nut (m. tetraphylla), which makes cis-9-palmitoleic acid a potential biomarker for the consumption of these food products. Cis-9-palmitoleic acid can be found primarily in most biofluids, including blood, saliva, feces, and urine, as well as in human adipose tissue, prostate and skeletal muscle tissues. Cis-9-palmitoleic acid exists in all living species, ranging from bacteria to humans. Moreover, cis-9-palmitoleic acid is found to be associated with isovaleric acidemia. CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5949; ORIGINAL_PRECURSOR_SCAN_NO 5948 INTERNAL_ID 900; CONFIDENCE standard compound; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5959; ORIGINAL_PRECURSOR_SCAN_NO 5958 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5959; ORIGINAL_PRECURSOR_SCAN_NO 5958 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5926; ORIGINAL_PRECURSOR_SCAN_NO 5924 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5944; ORIGINAL_PRECURSOR_SCAN_NO 5943 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5997; ORIGINAL_PRECURSOR_SCAN_NO 5996 CONFIDENCE standard compound; INTERNAL_ID 900; DATASET 20200303_ENTACT_RP_MIX508; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5943; ORIGINAL_PRECURSOR_SCAN_NO 5941 Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats. Palmitoleic acid, a composition of fatty acid, is implicated in the prevention of death from cerebrovascular disorders in SHRSP rats.

   
   

p-Hydroxybenzoic acid

p-Hydroxybenzoic acid

C7H6O3 (138.03169259999999)


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

   

α-Linolenic acid

alpha-Linolenic acid

C18H30O2 (278.224568)


α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1]. α-Linolenic acid, isolated from Perilla frutescens, is an essential fatty acid that cannot be synthesized by humans. α-Linolenic acid can affect the process of thrombotic through the modulation of PI3K/Akt signaling. α-Linolenic acid possess the anti-arrhythmic properties and is related to cardiovascular disease and cancer[1].

   

Syringic acid

Syringic acid

C9H10O5 (198.052821)


Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation. Syringic acid is correlated with high antioxidant activity and inhibition of LDL oxidation.

   

3,4-Dihydroxybenzoic acid

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266076)


   
   

Coniferyl alcohol

Coniferyl alcohol

C10H12O3 (180.0786402)


   
   

caryophyllene

(-)-beta-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.

   

Caftaric acid

(2R,3R)-2-{[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-hydroxybutanedioic acid

C13H12O9 (312.0481302)


Caftaric acid is a natural compound. Caftaric acid is a natural compound.

   

4,5-DCQA

(1R,3R,4S,5R)-3,4-bis({[(2E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-1,5-dihydroxycyclohexane-1-carboxylic acid

C25H24O12 (516.1267703999999)


3,4-Dicaffeoylquinic acid (3,4-Di-O-caffeoylquinic acid), naturally isolated from Laggera alata, has antioxidative, DNA protective, neuroprotective and hepatoprotective properties. 3,4-Dicaffeoylquinic acid exerts apoptosis-mediated cytotoxicity and α-glucosidase inhibitory effects. 3,4-Dicaffeoylquinic acid possesses a unique mechanism of anti-influenza viral activity, that is, enhancing viral clearance by increasing TRAIL[1][2][3]. 3,4-Dicaffeoylquinic acid (3,4-Di-O-caffeoylquinic acid), naturally isolated from Laggera alata, has antioxidative, DNA protective, neuroprotective and hepatoprotective properties. 3,4-Dicaffeoylquinic acid exerts apoptosis-mediated cytotoxicity and α-glucosidase inhibitory effects. 3,4-Dicaffeoylquinic acid possesses a unique mechanism of anti-influenza viral activity, that is, enhancing viral clearance by increasing TRAIL[1][2][3]. 4,5-Dicaffeoylquinic acid (Isochlorogenic acid C) is an antioxidant, can be isolated from Gynura divaricata and Laggera alata. 4,5-Dicaffeoylquinic acid reduces islet cell apoptosis and improves pancreatic function in type 2 diabetic mice, and has obvious inhibitory activities against yeast α-glucosidase. 4,5-Dicaffeoylquinic acid inhibits prostate cancer cells through cell cycle arrest. 4,5-Dicaffeoylquinic acid also has anti-apoptotic, anti-injury and anti-hepatitis B virus effects[1][2][3]. 4,5-Dicaffeoylquinic acid (Isochlorogenic acid C) is an antioxidant, can be isolated from Gynura divaricata and Laggera alata. 4,5-Dicaffeoylquinic acid reduces islet cell apoptosis and improves pancreatic function in type 2 diabetic mice, and has obvious inhibitory activities against yeast α-glucosidase. 4,5-Dicaffeoylquinic acid inhibits prostate cancer cells through cell cycle arrest. 4,5-Dicaffeoylquinic acid also has anti-apoptotic, anti-injury and anti-hepatitis B virus effects[1][2][3].

   

2-Pentadecanone

Methyl tridecyl ketone

C15H30O (226.22965299999998)


   

2-Tridecanone

Methyl n-undecyl ketone

C13H26O (198.1983546)


2-Tridecanone, a nonalkaloid insecticide, is isolated from the wild tomato Lycopersicon hirsutum f. glabratum. 2-Tridecanone is a volatile organic compound[1][2]. 2-Tridecanone, a nonalkaloid insecticide, is isolated from the wild tomato Lycopersicon hirsutum f. glabratum. 2-Tridecanone is a volatile organic compound[1][2].

   

beta-D-Galactopyranosyl-(1->4)-beta-D-galactopyranosyl-(1->4)-D-galactose

2-{[4,5-dihydroxy-2-(hydroxymethyl)-6-{[4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxan-3-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C18H32O16 (504.1690272)


   

Docosane

n-Docosane

C22H46 (310.3599316)


Docosane, a straight chain alkane, can be used to synthesize structural composites with thermal energy storage/release capability[1][2]. Docosane, a straight chain alkane, can be used to synthesize structural composites with thermal energy storage/release capability[1][2].

   

Heneicosane

Heneicosane

C21H44 (296.3442824)


Heneicosane is an aroma component isolated from Streptomyces philanthi RL-1-178 or Serapias cordigera. Heneicosane is a pheromone and inhibits aflatoxin production[1][2][3]. Heneicosane is an aroma component isolated from Streptomyces philanthi RL-1-178 or Serapias cordigera. Heneicosane is a pheromone and inhibits aflatoxin production[1][2][3].

   

HEXACOSANE

HEXACOSANE

C26H54 (366.4225284)


A straight-chain alkane comprising of 26 carbon atoms.

   

OCTACOSANE

OCTACOSANE

C28H58 (394.4538268)


A straight-chain alkane containing 28 carbon atoms.

   

1-PENTADECENE

1-PENTADECENE

C15H30 (210.234738)


An unbranched fifteen-carbon alkene with one double bond between C-1 and C-2.

   

DOTRIACONTANE

DOTRIACONTANE

C32H66 (450.5164236)


   

HENTRIACONTANE

HENTRIACONTANE

C31H64 (436.5007744)


   

NONADECANE

NONADECANE

C19H40 (268.31298400000003)


A straight-chain alkane with 19 carbon atoms. It has been found as a component of essential oils isolated from Artemisia armeniaca.

   

TETRACOSANE

TETRACOSANE

C24H50 (338.39123)


A straight-chain alkane containing 24 carbon atoms.

   

TRICOSANE

TRICOSANE

C23H48 (324.37558079999997)


A straight chain alkane containing 23 carbon atoms.

   
   

Chrysanthemin

cyanidin 3-O-glucoside

C21H21O11 (449.10838160000003)


   

octadeca-9,12,15-trienoic acid

octadeca-9,12,15-trienoic acid

C18H30O2 (278.224568)


   

Vanillate

4-Hydroxy-3-methoxybenzoic acid

C8H8O4 (168.0422568)


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

   

Nonacosane

EINECS 211-126-2

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].

   

linoleic

9,12-Octadecadienoic acid, (9E,12E)-

C18H32O2 (280.2402172)


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

   

Berberine

16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium

C20H18NO4+ (336.1235768)


Berberine is an organic heteropentacyclic compound, an alkaloid antibiotic, a botanical anti-fungal agent and a berberine alkaloid. It has a role as an antilipemic drug, a hypoglycemic agent, an antioxidant, a potassium channel blocker, an antineoplastic agent, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor, an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor, an EC 1.21.3.3 (reticuline oxidase) inhibitor, an EC 2.1.1.116 [3-hydroxy-N-methyl-(S)-coclaurine 4-O-methyltransferase] inhibitor, an EC 3.1.1.4 (phospholipase A2) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 2.7.11.10 (IkappaB kinase) inhibitor, an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor, a geroprotector and a metabolite. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. Berberine is a quaternary ammonia compound found in many botanical products, including goldenseal, barberry and Oregon grape, which is used for its purported antioxidant and antimicrobial properties for a host of conditions, including obesity, diabetes, hyperlipidemia, heart failure, H. pylori infection and colonic adenoma prevention. Berberine has not been linked to serum aminotransferase elevations during therapy nor to instances of clinically apparent liver injury. Berberine is a natural product found in Berberis poiretii, Thalictrum delavayi, and other organisms with data available. Berberine is a quaternary ammonium salt of an isoquinoline alkaloid and active component of various Chinese herbs, with potential antineoplastic, radiosensitizing, anti-inflammatory, anti-lipidemic and antidiabetic activities. Although the mechanisms of action through which berberine exerts its effects are not yet fully elucidated, upon administration this agent appears to suppress the activation of various proteins and/or modulate the expression of a variety of genes involved in tumorigenesis and inflammation, including, but not limited to transcription factor nuclear factor-kappa B (NF-kB), myeloid cell leukemia 1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), B-cell lymphoma-extra large (Bcl-xl), cyclooxygenase (COX)-2, tumor necrosis factor (TNF), interleukin (IL)-6, IL-12, inducible nitric oxide synthase (iNOS), intercellular adhesion molecule-1 (ICAM-1), E-selectin, monocyte chemoattractant protein-1 (MCP-1), C-X-C motif chemokine 2 (CXCL2), cyclin D1, activator protein (AP-1), hypoxia-inducible factor 1 (HIF-1), signal transducer and activator of transcription 3 (STAT3), peroxisome proliferator-activated receptor (PPAR), arylamine N-acetyltransferase (NAT), and DNA topoisomerase I and II. The modulation of gene expression may induce cell cycle arrest and apoptosis, and inhibit cancer cell proliferation. In addition, berberine modulates lipid and glucose metabolism. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. See also: Goldenseal (part of); Berberis aristata stem (part of). Berberine is a quaternary ammonium salt that belongs to the protoberberine group of benzylisoquinoline alkaloids. Chemically, berberine is classified as an isoquinoline alkaloid. More specifically, berberine is a plant alkaloid derived from tyrosine through a complex 8 step biosynthetic process. Berberine is found in plants such as Berberis vulgaris (barberry), Berberis aristata (tree turmeric), Mahonia aquifolium (Oregon grape) and Hydrastis canadensis (goldenseal). Two other known berberine-containing plants are Phellodendron chinense and Phellodendron amurense. Berberine is usually found in the roots, rhizomes, stems, and bark of Berberis plants. Due to berberines intense yellow color, plants that contain berberine were traditionally used to dye wool, leather, and wood. Under ultraviolet light, berberine shows a strong yellow fluorescence, making it useful in histology for staining heparin in mast cells. Berberine is a bioactive plant compound that has been frequently used in traditional medicine. Among the known physiological effects or bioactivities are: 1) Antimicrobial action against bacteria, fungi, protozoa, viruses, helminthes, and Chlamydia; 2) Antagonism against the effects of cholera and E coli heat-stable enterotoxin; 3) Inhibition of intestinal ion secretion and of smooth muscle contraction; 4) Reduction of inflammation and 5) Stimulation of bile secretion and bilirubin discharge (PMID:32335802). Berberine can inhibit bacterial growth in the gut, including Helicobacter pylori, protect the intestinal epithelial barrier from injury, and ameliorate liver injury. Currently, berberine is sold as an Over-the-Counter (OTC) drug for treating gastrointestinal infections in China (PMID:18442638). Berberine also inhibits the proliferation of various types of cancer cells and impedes invasion and metastasis (PMID:32335802). Recent evidence has also confirmed that berberine improves the efficacy and safety of both chemo and radiotherapies for cancer treatment (PMID:32335802). Berberine has also been shown to regulate glucose and lipid metabolism in vitro and in vivo (PMID:18442638). In fact, berberine is the main active component of an ancient Chinese herb Coptis chinensis French, which has been used to treat diabetes for thousands of years. As an anti-diabetic, berberine increases glucose uptake by muscle fibers independent of insulin levels. It triggers AMPK activation and increases glycolysis, leading to decreased insulin resistance and decreased oxygen respiration. The same mechanism leads to a reduction in gluconeogenesis in the liver. AMPK activation by berberine also leads to an antiatherosclerotic effect in mice. Berberines AMPK activation may also underlie berberines anti-obesity effects and favorable influence on weight loss (PMID:18442638). While its use as a medication is widely touted, it is important to remember that berberine inhibits CYP2D6 and CYP3A4 enzymes, both of which are involved in the metabolism of many endogenous substances and xenobiotics, including a number of prescription drugs. An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal. [HMDB] COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Hexadec-9-enoic acid

Hexadec-9-enoic acid

C16H30O2 (254.224568)


A hexadecenoic acid in which the double bond is located at position 9.

   

Danielone

Danielone

C10H12O5 (212.06847019999998)


An aromatic ketone that is 2-hydroxy-1-phenylethanone substituted by a hydroxy group at position 4 and methoxy groups at positions 3 and 5. It is a phytoalexin isolated from the papaya fruit and exhibits antifungal activity.

   

8-Hydroxy-3,9-dimethoxypterocarpan

8-Hydroxy-3,9-dimethoxypterocarpan

C17H16O5 (300.0997686)


   

(2e,4z)-n-(2-methylbutyl)dodeca-2,4-dien-8,10-diynimidic acid

(2e,4z)-n-(2-methylbutyl)dodeca-2,4-dien-8,10-diynimidic acid

C17H23NO (257.1779548)


   

(2e,9z)-n-ethylhexadeca-2,9-dien-12,14-diynimidic acid

(2e,9z)-n-ethylhexadeca-2,9-dien-12,14-diynimidic acid

C18H25NO (271.193604)


   

(2e,4e)-n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

(2e,4e)-n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

C15H19NO (229.14665639999998)


   

(9e)-8-hydroxypentadec-9-en-11,13-diyn-2-one

(9e)-8-hydroxypentadec-9-en-11,13-diyn-2-one

C15H20O2 (232.14632200000003)


   

tetradec-8-en-11,13-diyn-2-one

tetradec-8-en-11,13-diyn-2-one

C14H18O (202.1357578)


   

(2e,4e)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

(2e,4e)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

C16H25NO (247.193604)


   

n-(2-methylbutyl)dodec-2-en-8,10-diynimidic acid

n-(2-methylbutyl)dodec-2-en-8,10-diynimidic acid

C17H25NO (259.193604)


   

(8z)-tetradec-8-en-11,13-diyn-2-one

(8z)-tetradec-8-en-11,13-diyn-2-one

C14H18O (202.1357578)


   

(2e,4z,10z)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

(2e,4z,10z)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

C16H23NO (245.17795479999998)


   

1-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

1-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

C20H24O8 (392.1471104)


   

1-(4-hydroxy-3-methoxyphenyl)-2-{4-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy}propane-1,3-diol

1-(4-hydroxy-3-methoxyphenyl)-2-{4-[3-(hydroxymethyl)-5-(3-hydroxyprop-1-en-1-yl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy}propane-1,3-diol

C31H36O11 (584.2257506)


   

(2e,14e)-n-(2-methylpropyl)hexadeca-2,9,12,14-tetraenimidic acid

(2e,14e)-n-(2-methylpropyl)hexadeca-2,9,12,14-tetraenimidic acid

C20H33NO (303.25620080000004)


   

2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)ethanone

2-hydroxy-1-(4-hydroxy-3-methoxyphenyl)ethanone

C9H10O4 (182.057906)


   

(2e,4e,10e)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

(2e,4e,10e)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

C16H25NO (247.193604)


   

n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

C16H23NO (245.17795479999998)


   

pentadeca-8,13-dien-11-yn-2-one

pentadeca-8,13-dien-11-yn-2-one

C15H22O (218.1670562)


   

10-hydroxy-9-isopropyl-1,6-dimethyl-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-8-yl 3-phenylprop-2-enoate

10-hydroxy-9-isopropyl-1,6-dimethyl-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-8-yl 3-phenylprop-2-enoate

C24H32O5 (400.2249622)


   

(2e)-n-[(2s)-2-methylbutyl]dodec-2-en-8,10-diynimidic acid

(2e)-n-[(2s)-2-methylbutyl]dodec-2-en-8,10-diynimidic acid

C17H25NO (259.193604)


   

(2z)-n-(2-methylpropyl)undec-2-en-8,10-diynimidic acid

(2z)-n-(2-methylpropyl)undec-2-en-8,10-diynimidic acid

C15H21NO (231.1623056)


   

8-hydroxypentadeca-9,13-dien-11-yn-2-one

8-hydroxypentadeca-9,13-dien-11-yn-2-one

C15H22O2 (234.1619712)


   

(1r,2s)-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(2s,3s)-3-(hydroxymethyl)-5-[(1e)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy}propane-1,3-diol

(1r,2s)-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(2s,3s)-3-(hydroxymethyl)-5-[(1e)-3-hydroxyprop-1-en-1-yl]-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy}propane-1,3-diol

C31H36O11 (584.2257506)


   

n-(2-methylpropyl)pentadeca-2,9-dien-12,14-diynimidic acid

n-(2-methylpropyl)pentadeca-2,9-dien-12,14-diynimidic acid

C19H27NO (285.2092532)


   

{6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5-hydroxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

{6-[2-(3,4-dihydroxyphenyl)ethoxy]-3-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-5-hydroxy-4-[(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy]oxan-2-yl}({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})methyl 3-(3,4-dihydroxyphenyl)prop-2-enoate

C44H52O24 (964.2848392000001)


   

(8r,9e)-8-hydroxypentadec-9-en-11,13-diyn-2-one

(8r,9e)-8-hydroxypentadec-9-en-11,13-diyn-2-one

C15H20O2 (232.14632200000003)


   

(2r,3s,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

(2r,3s,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-4,5-dihydroxy-2-(hydroxymethyl)oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C23H26O11 (478.14750460000005)


   

n-[(2r)-2-methylbutyl]dodeca-2,4-dienimidic acid

n-[(2r)-2-methylbutyl]dodeca-2,4-dienimidic acid

C17H31NO (265.2405516)


   

(2e,4z)-n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

(2e,4z)-n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

C15H19NO (229.14665639999998)


   

(2e,9z)-n-(2-methylpropyl)pentadeca-2,9-dien-12,14-diynimidic acid

(2e,9z)-n-(2-methylpropyl)pentadeca-2,9-dien-12,14-diynimidic acid

C19H27NO (285.2092532)


   

(2e,4e,8z)-n-(2-methylpropyl)dodeca-2,4,8-trienimidic acid

(2e,4e,8z)-n-(2-methylpropyl)dodeca-2,4,8-trienimidic acid

C16H27NO (249.20925319999998)


   

2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-{[3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

C23H20O12 (488.09547200000003)


   

1,4-bis(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol

1,4-bis(4-hydroxy-3-methoxyphenyl)-tetrahydro-1h-furo[3,4-c]furan-3a-ol

C20H22O7 (374.1365462)


   

(2e,4e,8e,10z)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

(2e,4e,8e,10z)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

C16H25NO (247.193604)


   

(2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

(2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-{[(2e)-3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

C22H18O11 (458.0849078)


   

(3e)-heptadeca-1,3-diene

(3e)-heptadeca-1,3-diene

C17H32 (236.2503872)


   

heptadeca-1,3,5-triene

heptadeca-1,3,5-triene

C17H30 (234.234738)


   

n-(2-methylpropyl)dodeca-2,4-dienimidic acid

n-(2-methylpropyl)dodeca-2,4-dienimidic acid

C16H29NO (251.2249024)


   

8-hydroxypentadec-9-en-11,13-diyn-2-one

8-hydroxypentadec-9-en-11,13-diyn-2-one

C15H20O2 (232.14632200000003)


   

(2e,4z)-n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

(2e,4z)-n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

C16H21NO (243.1623056)


   

1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy]propane-1,3-diol

1-(4-hydroxy-3-methoxyphenyl)-2-[4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy]propane-1,3-diol

C20H24O7 (376.1521954)


   

1-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)-2-hydroxyethanone

1-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)-2-hydroxyethanone

C20H24O9 (408.14202539999997)


   

(1r)-1,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid

(1r)-1,3-bis({[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic acid

C25H24O12 (516.1267703999999)


   

(9e,13z)-pentadeca-9,13-dien-11-yne-2,8-dione

(9e,13z)-pentadeca-9,13-dien-11-yne-2,8-dione

C15H20O2 (232.14632200000003)


   

(2e,4e,8z,10z)-n-(2-methylpropyl)tetradeca-2,4,8,10-tetraenimidic acid

(2e,4e,8z,10z)-n-(2-methylpropyl)tetradeca-2,4,8,10-tetraenimidic acid

C18H29NO (275.2249024)


   

(2e,9z)-n-(2-methylpropyl)hexadeca-2,9-dien-12,14-diynimidic acid

(2e,9z)-n-(2-methylpropyl)hexadeca-2,9-dien-12,14-diynimidic acid

C20H29NO (299.2249024)


   

n-(2-methylpropyl)hexadeca-2,9-dien-12,14-diynimidic acid

n-(2-methylpropyl)hexadeca-2,9-dien-12,14-diynimidic acid

C20H29NO (299.2249024)


   

(2e,4e,10z)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

(2e,4e,10z)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

C16H23NO (245.17795479999998)


   

heptadeca-1,3-diene

heptadeca-1,3-diene

C17H32 (236.2503872)


   

(8r,9e,13z)-8-hydroxypentadeca-9,13-dien-11-yn-2-one

(8r,9e,13z)-8-hydroxypentadeca-9,13-dien-11-yn-2-one

C15H22O2 (234.1619712)


   

(2e,6z,8e,10e)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

(2e,6z,8e,10e)-n-(2-methylpropyl)dodeca-2,6,8,10-tetraenimidic acid

C16H25NO (247.193604)


   

(9e)-pentadec-9-en-11,13-diyne-2,8-dione

(9e)-pentadec-9-en-11,13-diyne-2,8-dione

C15H18O2 (230.1306728)


   

2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

2-{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-{[3-(4-hydroxyphenyl)prop-2-enoyl]oxy}butanedioic acid

C22H18O11 (458.0849078)


   

1-(4-{[1,3-dihydroxy-1-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

1-(4-{[1,3-dihydroxy-1-(3-methoxy-4-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

C26H34O13 (554.1999314)


   

2-{3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl}-4-hydroxybut-2-en-1-yl acetate

2-{3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl}-4-hydroxybut-2-en-1-yl acetate

C22H36O4 (364.2613456)


   

(2z)-2-[(2r,3as,5as,9ar,9br)-3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl]-4-hydroxybut-2-en-1-yl acetate

(2z)-2-[(2r,3as,5as,9ar,9br)-3a,6,6,9a-tetramethyl-octahydro-1h-naphtho[2,1-b]furan-2-yl]-4-hydroxybut-2-en-1-yl acetate

C22H36O4 (364.2613456)


   

n-(2-methylbutyl)trideca-2,7-dien-10,12-diynimidic acid

n-(2-methylbutyl)trideca-2,7-dien-10,12-diynimidic acid

C18H25NO (271.193604)


   

(8z,11z)-pentadeca-8,11-dien-2-one

(8z,11z)-pentadeca-8,11-dien-2-one

C15H26O (222.1983546)


   

pentadeca-9,13-dien-11-yne-2,8-dione

pentadeca-9,13-dien-11-yne-2,8-dione

C15H20O2 (232.14632200000003)


   

n-(2-methylpropyl)trideca-2,6,8-trien-10,12-diynimidic acid

n-(2-methylpropyl)trideca-2,6,8-trien-10,12-diynimidic acid

C17H21NO (255.1623056)


   

(8z,13z)-pentadeca-8,13-dien-11-yn-2-one

(8z,13z)-pentadeca-8,13-dien-11-yn-2-one

C15H22O (218.1670562)


   

(2e,9z)-n-(2-hydroxy-2-methylpropyl)pentadeca-2,9-dien-12,14-diynimidic acid

(2e,9z)-n-(2-hydroxy-2-methylpropyl)pentadeca-2,9-dien-12,14-diynimidic acid

C19H27NO2 (301.20416819999997)


   

(1s,3r,4r,5s)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

(1s,3r,4r,5s)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic acid

C16H18O9 (354.0950778)


   

(2e,9z,12z,14e)-n-(2-methylpropyl)hexadeca-2,9,12,14-tetraenimidic acid

(2e,9z,12z,14e)-n-(2-methylpropyl)hexadeca-2,9,12,14-tetraenimidic acid

C20H33NO (303.25620080000004)


   

(1z,6z,8s)-8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

(1z,6z,8s)-8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

C15H24 (204.18779039999998)


   

n-(2-methylpropyl)hexadeca-2,9,12,14-tetraenimidic acid

n-(2-methylpropyl)hexadeca-2,9,12,14-tetraenimidic acid

C20H33NO (303.25620080000004)


   

(2e,4z)-n-[(2s)-2-methylbutyl]dodeca-2,4-dien-8,10-diynimidic acid

(2e,4z)-n-[(2s)-2-methylbutyl]dodeca-2,4-dien-8,10-diynimidic acid

C17H23NO (257.1779548)


   

(8r,9e)-8-hydroxytetradec-9-en-11,13-diyn-2-one

(8r,9e)-8-hydroxytetradec-9-en-11,13-diyn-2-one

C14H18O2 (218.1306728)


   

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4-hydroxybenzoate

3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl 4-hydroxybenzoate

C13H16O8 (300.0845136)


   

1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

C26H34O13 (554.1999314)


   

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

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

C44H52O24 (964.2848392000001)


   

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

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

C29H36O15 (624.2054106)


   

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

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

C35H46O20 (786.2582316)


   

5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

5,7-dihydroxy-2-(4-hydroxy-3-oxidophenyl)-3-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1λ⁴-chromen-1-ylium

C21H20O11 (448.100557)


   

n-(2-methylpropyl)dodec-2-en-8,10-diynimidic acid

n-(2-methylpropyl)dodec-2-en-8,10-diynimidic acid

C16H23NO (245.17795479999998)


   

n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

C15H19NO (229.14665639999998)


   

(2e)-n-(2-methylpropyl)undec-2-en-8,10-diynimidic acid

(2e)-n-(2-methylpropyl)undec-2-en-8,10-diynimidic acid

C15H21NO (231.1623056)


   

(2e,4z,10e)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

(2e,4z,10e)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

C16H23NO (245.17795479999998)


   

8-hydroxytetradec-9-en-11,13-diyn-2-one

8-hydroxytetradec-9-en-11,13-diyn-2-one

C14H18O2 (218.1306728)


   

2-({3-[2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

2-({3-[2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C27H34O11 (534.2101014)


   

(8z,10e,12r,14z)-12-hydroxyheptadeca-8,10,14-trienoic acid

(8z,10e,12r,14z)-12-hydroxyheptadeca-8,10,14-trienoic acid

C17H28O3 (280.2038338)


   

(1r,2s)-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(1e)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}propane-1,3-diol

(1r,2s)-1-(4-hydroxy-3-methoxyphenyl)-2-{4-[(1e)-3-hydroxyprop-1-en-1-yl]-2-methoxyphenoxy}propane-1,3-diol

C20H24O7 (376.1521954)


   

(1r,2r,3s,4r,6e,10s)-2-hydroxy-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-4-yl (2e)-3-phenylprop-2-enoate

(1r,2r,3s,4r,6e,10s)-2-hydroxy-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-4-yl (2e)-3-phenylprop-2-enoate

C24H32O4 (384.2300472)


   

n-(2-methylpropyl)trideca-2,7-dien-10,12-diynimidic acid

n-(2-methylpropyl)trideca-2,7-dien-10,12-diynimidic acid

C17H23NO (257.1779548)


   

pentadec-9-en-11,13-diyne-2,8-dione

pentadec-9-en-11,13-diyne-2,8-dione

C15H18O2 (230.1306728)


   

(2z)-n-[(2s)-2-methylbutyl]dodec-2-en-8,10-diynimidic acid

(2z)-n-[(2s)-2-methylbutyl]dodec-2-en-8,10-diynimidic acid

C17H25NO (259.193604)


   

n-(2-methylbutyl)undeca-2,4-dien-8,10-diynimidic acid

n-(2-methylbutyl)undeca-2,4-dien-8,10-diynimidic acid

C16H21NO (243.1623056)


   

(6e)-2,6-dimethyl-10-methylidenedodeca-2,6-diene

(6e)-2,6-dimethyl-10-methylidenedodeca-2,6-diene

C15H26 (206.2034396)


   

(1s,2r,3s,4r,6z,10s)-2-hydroxy-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-4-yl (2e)-3-phenylprop-2-enoate

(1s,2r,3s,4r,6z,10s)-2-hydroxy-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-4-yl (2e)-3-phenylprop-2-enoate

C24H32O4 (384.2300472)


   

(1s,3ar,6r,7s,8r,8ar)-1,8-dihydroxy-7-isopropyl-1-methyl-4-methylidene-octahydroazulen-6-yl (2e)-3-phenylprop-2-enoate

(1s,3ar,6r,7s,8r,8ar)-1,8-dihydroxy-7-isopropyl-1-methyl-4-methylidene-octahydroazulen-6-yl (2e)-3-phenylprop-2-enoate

C24H32O4 (384.2300472)


   

(2e)-n-(2-methylbutyl)dodec-2-en-8,10-diynimidic acid

(2e)-n-(2-methylbutyl)dodec-2-en-8,10-diynimidic acid

C17H25NO (259.193604)


   

(1s,3r,4s,5s,6r,7r)-5-hydroxy-4-isopropyl-1-methyl-7-(3-oxobutyl)bicyclo[4.1.0]heptan-3-yl (2e)-3-phenylprop-2-enoate

(1s,3r,4s,5s,6r,7r)-5-hydroxy-4-isopropyl-1-methyl-7-(3-oxobutyl)bicyclo[4.1.0]heptan-3-yl (2e)-3-phenylprop-2-enoate

C24H32O4 (384.2300472)


   

1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

1-(4-{[(1r,2s)-1,3-dihydroxy-1-(3-methoxy-4-{[(2s,3s,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

C26H34O13 (554.1999314)


   

(2e)-n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

(2e)-n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

C16H21NO (243.1623056)


   

(1s,3r,4s,5r,6r,7r)-5-hydroxy-4-isopropyl-1-methyl-7-(3-oxobutyl)bicyclo[4.1.0]heptan-3-yl (2e)-3-phenylprop-2-enoate

(1s,3r,4s,5r,6r,7r)-5-hydroxy-4-isopropyl-1-methyl-7-(3-oxobutyl)bicyclo[4.1.0]heptan-3-yl (2e)-3-phenylprop-2-enoate

C24H32O4 (384.2300472)


   
   

(2e,6e,8z)-n-(2-methylpropyl)trideca-2,6,8-trien-10,12-diynimidic acid

(2e,6e,8z)-n-(2-methylpropyl)trideca-2,6,8-trien-10,12-diynimidic acid

C17H21NO (255.1623056)


   

(2e,4e)-n-(2-methylpropyl)dodeca-2,4-dienimidic acid

(2e,4e)-n-(2-methylpropyl)dodeca-2,4-dienimidic acid

C16H29NO (251.2249024)


   

(2e)-n-(2-methylpropyl)dodec-2-en-8,10-diynimidic acid

(2e)-n-(2-methylpropyl)dodec-2-en-8,10-diynimidic acid

C16H23NO (245.17795479999998)


   

n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

C16H21NO (243.1623056)


   

(2e,4z)-n-[(2s)-2-methylbutyl]undeca-2,4-dien-8,10-diynimidic acid

(2e,4z)-n-[(2s)-2-methylbutyl]undeca-2,4-dien-8,10-diynimidic acid

C16H21NO (243.1623056)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.386145)


   

(2e,4z)-n-(2-methylbutyl)undeca-2,4-dien-8,10-diynimidic acid

(2e,4z)-n-(2-methylbutyl)undeca-2,4-dien-8,10-diynimidic acid

C16H21NO (243.1623056)


   

(2e,7z)-n-(2-methylpropyl)trideca-2,7-dien-10,12-diynimidic acid

(2e,7z)-n-(2-methylpropyl)trideca-2,7-dien-10,12-diynimidic acid

C17H23NO (257.1779548)


   

(2e)-n-(2-methylpropyl)tetradec-2-en-10,12-diynimidic acid

(2e)-n-(2-methylpropyl)tetradec-2-en-10,12-diynimidic acid

C18H27NO (273.2092532)


   

2-hydroxy-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-4-yl 3-phenylprop-2-enoate

2-hydroxy-3-isopropyl-6,10-dimethyl-11-oxabicyclo[8.1.0]undec-6-en-4-yl 3-phenylprop-2-enoate

C24H32O4 (384.2300472)


   

(2e,7z)-n-[(2s)-2-methylbutyl]trideca-2,7-dien-10,12-diynimidic acid

(2e,7z)-n-[(2s)-2-methylbutyl]trideca-2,7-dien-10,12-diynimidic acid

C18H25NO (271.193604)


   

(2e,4e)-n-[(2r)-2-methylbutyl]dodeca-2,4-dienimidic acid

(2e,4e)-n-[(2r)-2-methylbutyl]dodeca-2,4-dienimidic acid

C17H31NO (265.2405516)


   

(2r,3r,4s,5s,6r)-2-{[(2e)-3-[(2r,3s)-2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(2e)-3-[(2r,3s)-2-(3,4-dimethoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydro-1-benzofuran-5-yl]prop-2-en-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C27H34O11 (534.2101014)


   

1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid

1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid

C25H24O12 (516.1267703999999)


   

n-(2-methylpropyl)undec-2-en-8,10-diynimidic acid

n-(2-methylpropyl)undec-2-en-8,10-diynimidic acid

C15H21NO (231.1623056)


   

(1r,3s,4r,5s)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid

(1r,3s,4r,5s)-1,4-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-3,5-dihydroxycyclohexane-1-carboxylic acid

C25H24O12 (516.1267703999999)


   

(2e,4e,8z,10e)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

(2e,4e,8z,10e)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

C16H25NO (247.193604)


   

6'-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5,5'-tetrahydroxy-6-methyl-2'-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-[2,4'-bioxan]-3'-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

6'-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5,5'-tetrahydroxy-6-methyl-2'-({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-[2,4'-bioxan]-3'-yl 3-(3,4-dihydroxyphenyl)prop-2-enoate

C35H46O19 (770.2633166)


   
   

(1s,4s,6r,8r,9s,10r,11r)-10-hydroxy-9-isopropyl-1,6-dimethyl-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-8-yl (2e)-3-phenylprop-2-enoate

(1s,4s,6r,8r,9s,10r,11r)-10-hydroxy-9-isopropyl-1,6-dimethyl-5,12-dioxatricyclo[9.1.0.0⁴,⁶]dodecan-8-yl (2e)-3-phenylprop-2-enoate

C24H32O5 (400.2249622)


   

3-{[(2s,5s)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

3-{[(2s,5s)-6-{[(2-carboxyacetyl)oxy]methyl}-3,4,5-trihydroxyoxan-2-yl]oxy}-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-1λ⁴-chromen-1-ylium

[C24H23O14]+ (535.1087758)


   

(3e,5e)-heptadeca-1,3,5-triene

(3e,5e)-heptadeca-1,3,5-triene

C17H30 (234.234738)


   

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

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

C29H36O15 (624.2054106)


   

1,8-dihydroxy-7-isopropyl-1-methyl-4-methylidene-octahydroazulen-6-yl 3-phenylprop-2-enoate

1,8-dihydroxy-7-isopropyl-1-methyl-4-methylidene-octahydroazulen-6-yl 3-phenylprop-2-enoate

C24H32O4 (384.2300472)


   

(4e)-n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

(4e)-n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

C15H19NO (229.14665639999998)


   

n-(2-methylpropyl)tetradec-2-en-10,12-diynimidic acid

n-(2-methylpropyl)tetradec-2-en-10,12-diynimidic acid

C18H27NO (273.2092532)


   

1-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

1-(4-{[(1r,2s)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)ethanone

C20H24O8 (392.1471104)


   

(2z)-n-(2-methylbutyl)undec-2-en-8,10-diynimidic acid

(2z)-n-(2-methylbutyl)undec-2-en-8,10-diynimidic acid

C16H23NO (245.17795479999998)


   

8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

8-isopropyl-1-methyl-5-methylidenecyclodeca-1,6-diene

C15H24 (204.18779039999998)


   

(2z,4e,10z)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

(2z,4e,10z)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

C16H23NO (245.17795479999998)


   

(2z,4e)-n-(2-methylbutyl)undeca-2,4-dien-8,10-diynimidic acid

(2z,4e)-n-(2-methylbutyl)undeca-2,4-dien-8,10-diynimidic acid

C16H21NO (243.1623056)


   

(2e,4e)-n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

(2e,4e)-n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

C16H21NO (243.1623056)


   

(2z,4e)-n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

(2z,4e)-n-(2-methylpropyl)undeca-2,4-dien-8,10-diynimidic acid

C15H19NO (229.14665639999998)


   

2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy]oxane-3,4,5-triol

2-(hydroxymethyl)-6-[4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenoxy]oxane-3,4,5-triol

C16H22O8 (342.1314612)


   

5-hydroxy-4-isopropyl-1-methyl-7-(3-oxobutyl)bicyclo[4.1.0]heptan-3-yl 3-phenylprop-2-enoate

5-hydroxy-4-isopropyl-1-methyl-7-(3-oxobutyl)bicyclo[4.1.0]heptan-3-yl 3-phenylprop-2-enoate

C24H32O4 (384.2300472)


   

(2z,4e)-n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

(2z,4e)-n-(2-methylpropyl)dodeca-2,4-dien-8,10-diynimidic acid

C16H21NO (243.1623056)


   

(2e,4e,10e)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

(2e,4e,10e)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

C16H23NO (245.17795479999998)


   

n-(2-hydroxy-2-methylpropyl)pentadeca-2,9-dien-12,14-diynimidic acid

n-(2-hydroxy-2-methylpropyl)pentadeca-2,9-dien-12,14-diynimidic acid

C19H27NO2 (301.20416819999997)


   

1-(4-hydroxy-3-methoxyphenyl)-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethanone

1-(4-hydroxy-3-methoxyphenyl)-2-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethanone

C15H20O9 (344.110727)


   

n-(2-methylbutyl)dodeca-2,4-dien-8,10-diynimidic acid

n-(2-methylbutyl)dodeca-2,4-dien-8,10-diynimidic acid

C17H23NO (257.1779548)


   

(2e)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

(2e)-n-(2-methylpropyl)dodeca-2,4,10-trien-8-ynimidic acid

C16H23NO (245.17795479999998)


   

1-(4-hydroxy-3-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethanone

1-(4-hydroxy-3-methoxyphenyl)-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}ethanone

C15H20O9 (344.110727)


   

n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

C16H25NO (247.193604)


   

(2r,2'r,3r,3's,4r,4's,5r,5'r,6s,6'r)-6'-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5,5'-tetrahydroxy-6-methyl-2'-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-[2,4'-bioxan]-3'-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

(2r,2'r,3r,3's,4r,4's,5r,5'r,6s,6'r)-6'-[2-(3,4-dihydroxyphenyl)ethoxy]-3,4,5,5'-tetrahydroxy-6-methyl-2'-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)-[2,4'-bioxan]-3'-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

C35H46O19 (770.2633166)


   

(2e,4e,8z,10z)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

(2e,4e,8z,10z)-n-(2-methylpropyl)dodeca-2,4,8,10-tetraenimidic acid

C16H25NO (247.193604)


   

1-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)-2-hydroxyethanone

1-(4-{[1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy}-3,5-dimethoxyphenyl)-2-hydroxyethanone

C20H24O9 (408.14202539999997)


   

(2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

(2r,3r)-2-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-3-{[(2e)-3-(4-hydroxy-3-methoxyphenyl)prop-2-enoyl]oxy}butanedioic acid

C23H20O12 (488.09547200000003)