NCBI Taxonomy: 7055

Adenosine

C10H13N5O4 (267.0967)

Adenosine is a ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. It has a role as an anti-arrhythmia drug, a vasodilator agent, an analgesic, a human metabolite and a fundamental metabolite. It is a purines D-ribonucleoside and a member of adenosines. It is functionally related to an adenine. The structure of adenosine was first described in 1931, though the vasodilating effects were not described in literature until the 1940s. Adenosine is indicated as an adjunct to thallium-201 in myocardial perfusion scintigraphy, though it is rarely used in this indication, having largely been replaced by [dipyridamole] and [regadenson]. Adenosine is also indicated in the treatment of supraventricular tachycardia. Adenosine was granted FDA approval on 30 October 1989. Adenosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Adenosine is an Adenosine Receptor Agonist. The mechanism of action of adenosine is as an Adenosine Receptor Agonist. Adenosine is a natural product found in Smilax bracteata, Mikania laevigata, and other organisms with data available. Adenosine is a ribonucleoside comprised of adenine bound to ribose, with vasodilatory, antiarrhythmic and analgesic activities. Phosphorylated forms of adenosine play roles in cellular energy transfer, signal transduction and the synthesis of RNA. Adenosine is a nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer - as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate, cAMP. Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously, adenosine causes transient heart block in the AV node. Because of the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Adenosine is a metabolite found in or produced by Saccharomyces cerevisiae. A nucleoside that is composed of adenine and d-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. Adenosine itself is a neurotransmitter. See also: Adenosine; Niacinamide (component of); Adenosine; Glycerin (component of); Adenosine; ginsenosides (component of) ... View More ... Adenosine is a nucleoside that is composed of adenine and D-ribose. Adenosine or adenosine derivatives play many important biological roles in addition to being components of DNA and RNA. For instance, adenosine plays an important role in energy transfer as adenosine triphosphate (ATP) and adenosine diphosphate (ADP). It also plays a role in signal transduction as cyclic adenosine monophosphate (cAMP). Adenosine itself is both a neurotransmitter and potent vasodilator. When administered intravenously adenosine causes transient heart block in the AV node. Due to the effects of adenosine on AV node-dependent supraventricular tachycardia, adenosine is considered a class V antiarrhythmic agent. Overdoses of adenosine intake (as a drug) can lead to several side effects including chest pain, feeling faint, shortness of breath, and tingling of the senses. Serious side effects include a worsening dysrhythmia and low blood pressure. When present in sufficiently high levels, adenosine can act as an immunotoxin and a metabotoxin. An immunotoxin disrupts, limits the function, or destroys immune cells. A metabotoxin is an endogenous metabolite that causes adverse health effects at chronically high levels. Chronically high levels of adenosine are associated with adenosine deaminase deficiency. Adenosine is a precursor to deoxyadenosine, which is a precursor to dATP. A buildup of dATP in cells inhibits ribonucleotide reductase and prevents DNA synthesis, so cells are unable to divide. Since developing T cells and B cells are some of the most mitotically active cells, they are unable to divide and propagate to respond to immune challenges. High levels of deoxyadenosine also lead to an increase in S-adenosylhomocysteine, which is toxic to immature lymphocytes. Adenosine is a nucleoside composed of a molecule of adenine attached to a ribose sugar molecule (ribofuranose) moiety via a beta-N9-glycosidic bond. [Wikipedia]. Adenosine is found in many foods, some of which are borage, japanese persimmon, nuts, and barley. COVID info from PDB, Protein Data Bank, COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials A ribonucleoside composed of a molecule of adenine attached to a ribofuranose moiety via a beta-N(9)-glycosidic bond. Adenosine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-61-7 (retrieved 2024-06-29) (CAS RN: 58-61-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2].

Sucrose

C12H22O11 (342.1162)

Sucrose is a nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane (Saccharum officinarum), sugar beet (Beta vulgaris), and other plants and used extensively as a food and a sweetener. Sucrose is derived by crushing and extracting sugarcane with water or by extracting sugar beet with water, evaporating, and purifying with lime, carbon, and various liquids. Sucrose is also obtainable from sorghum. Sucrose occurs in low percentages in honey and maple syrup. Sucrose is used as a sweetener in foods and soft drinks, in the manufacture of syrups, in invert sugar, confectionery, preserves and jams, demulcent, pharmaceutical products, and caramel. Sucrose is also a chemical intermediate for detergents, emulsifying agents, and other sucrose derivatives. Sucrose is widespread in the seeds, leaves, fruits, flowers, and roots of plants, where it functions as an energy store for metabolism and as a carbon source for biosynthesis. The annual world production of sucrose is in excess of 90 million tons mainly from the juice of sugar cane (20\\\%) and sugar beet (17\\\%). In addition to its use as a sweetener, sucrose is used in food products as a preservative, antioxidant, moisture control agent, stabilizer, and thickening agent. BioTransformer predicts that sucrose is a product of 6-O-sinapoyl sucrose metabolism via a hydrolysis-of-carboxylic-acid-ester-pattern1 reaction occurring in human gut microbiota and catalyzed by the liver carboxylesterase 1 (P23141) enzyme (PMID: 30612223). Sucrose appears as white odorless crystalline or powdery solid. Denser than water. Sucrose is a glycosyl glycoside formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose. It has a role as an osmolyte, a sweetening agent, a human metabolite, an algal metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. A nonreducing disaccharide composed of glucose and fructose linked via their anomeric carbons. It is obtained commercially from sugarcane, sugar beet (beta vulgaris), and other plants and used extensively as a food and a sweetener. Sucrose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Sucrose is a natural product found in Haplophyllum ramosissimum, Cyperus esculentus, and other organisms with data available. Sucrose is a metabolite found in or produced by Saccharomyces cerevisiae. A nonreducing disaccharide composed of GLUCOSE and FRUCTOSE linked via their anomeric carbons. It is obtained commercially from SUGARCANE, sugar beet (BETA VULGARIS), and other plants and used extensively as a food and a sweetener. See also: Anise; ferrous disulfide; sucrose (component of); Phosphoric acid; sucrose (component of); Sucrose caramel (related) ... View More ... In chemistry, sugar loosely refers to a number of carbohydrates, such as monosaccharides, disaccharides, or oligosaccharides. In food, sugar refers to a class of edible crystalline carbohydrates, mainly sucrose, lactose, and fructose characterized by a sweet flavor. Other sugars are used in industrial food preparation, but are usually known by more specific names - glucose, fructose or fruit sugar, high fructose corn syrup, etc. Sugars is found in many foods, some of which are ucuhuba, butternut squash, common walnut, and miso. A glycosyl glycoside formed by glucose and fructose units joined by an acetal oxygen bridge from hemiacetal of glucose to the hemiketal of the fructose. Sucrose, a disaccharide, is a sugar composed of glucose and fructose subunits. It is produced naturally in plants and is the main constituent of white sugar. It has the molecular formula C 12H 22O 11. For human consumption, sucrose is extracted and refined from either sugarcane or sugar beet. Sugar mills – typically located in tropical regions near where sugarcane is grown – crush the cane and produce raw sugar which is shipped to other factories for refining into pure sucrose. Sugar beet factories are located in temperate climates where the beet is grown, and process the beets directly into refined sugar. The sugar-refining process involves washing the raw sugar crystals before dissolving them into a sugar syrup which is filtered and then passed over carbon to remove any residual colour. The sugar syrup is then concentrated by boiling under a vacuum and crystallized as the final purification process to produce crystals of pure sucrose that are clear, odorless, and sweet. Sugar is often an added ingredient in food production and recipes. About 185 million tonnes of sugar were produced worldwide in 2017.[6] Sucrose is particularly dangerous as a risk factor for tooth decay because Streptococcus mutans bacteria convert it into a sticky, extracellular, dextran-based polysaccharide that allows them to cohere, forming plaque. Sucrose is the only sugar that bacteria can use to form this sticky polysaccharide.[7] Sucrose. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=8030-20-4 (retrieved 2024-06-29) (CAS RN: 57-50-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

Gallic acid

C7H6O5 (170.0215)

Gallic acid is an odorless white solid. Sinks in water. (USCG, 1999) Gallic acid is a trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. It has a role as an astringent, a cyclooxygenase 2 inhibitor, a plant metabolite, an antioxidant, an antineoplastic agent, a human xenobiotic metabolite, an EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor, an apoptosis inducer and a geroprotector. It is a conjugate acid of a gallate. Gallic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Gallic Acid is a natural product found in Visnea mocanera, Ardisia paniculata, and other organisms with data available. Gallic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A colorless or slightly yellow crystalline compound obtained from nutgalls. It is used in photography, pharmaceuticals, and as an analytical reagent. See also: Gallic acid monohydrate (active moiety of); Paeonia lactiflora root (part of); Galium aparine whole (part of) ... View More ... Gallic acid is an organic acid, also known as 3,4,5-trihydroxybenzoic acid, found in gallnuts, sumac, witch hazel, tea leaves, oak bark, and other plants. The chemical formula is C6H2(OH)3CO2H. Gallic acid is widely distributed in plants and is found both free and as part of tannins. It is commonly used in the pharmaceutical industry. Gallic acid can also be used to synthesize the hallucinogenic alkaloid mescaline, also known as 3,4,5-trimethoxyphenethylamine. Salts and esters of gallic acid are termed gallates. Gallic acid has been found to be s metabolite of Aspergillus (PMID:24031294). A trihydroxybenzoic acid in which the hydroxy groups are at positions 3, 4, and 5. Present in red wine. Japan approved food antioxidant additive Gallic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=149-91-7 (retrieved 2024-07-01) (CAS RN: 149-91-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2]. Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2].

Protocatechuic acid

C7H6O4 (154.0266)

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.

Inosine

C10H12N4O5 (268.0808)

Inosine, also known as hypoxanthosine or inotin, belongs to the class of organic compounds known as purine nucleosides. Purine nucleosides are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety. Inosine is formed when hypoxanthine is attached to a ribose ring a beta-N9-glycosidic bond. Inosine is an intermediate in the degradation of purines and purine nucleosides to uric acid. Inosine is also an intermediate in the purine salvage pathway. Inosine occurs in the anticodon of certain transfer RNA molecules and is essential for proper translation of the genetic code in wobble base pairs. Inosine exists in all living species, ranging from bacteria to plants to humans. Inosine participates in a number of enzymatic reactions. In particular, inosine can be biosynthesized from inosinic acid through its interaction with the enzyme known as cytosolic purine 5-nucleotidase. In addition, inosine can be converted into hypoxanthine and ribose 1-phosphate through its interaction with the enzyme known as purine nucleoside phosphorylase. Altered levels of inosine have also been associated with purine nucleoside phosphorylase deficiency and xanthinuria type I, both of which are inborn errors of metabolism. Animal studies have suggested that inosine has neuroprotective properties. It has been proposed as a potential treatment for spinal cord injury (PMID: 16317421) and for administration after stroke, as inosine appears to induce axonal rewiring (PMID: 12084941). After ingestion, inosine is metabolized into uric acid, which has been found to be a natural antioxidant and peroxynitrite scavenger. As such, inosine may have potential benefits to patients with multiple sclerosis and Parkinson’s disease (PMID: 19425822). Inosine can also be produced by gut bacteria and appears to have a number of beneficial effects. Inosine, has been shown to activate peroxisome proliferator-activated receptor (PPAR)-gamma signaling in human colon epithelial cells. Furthermore, exogenous treatment of inosine has been found to protect against DSS-induced colitis in rodents by improving adenosine 2A receptor (A2AR)/PPAR-gamma-dependent mucosal barrier functions (PMID: 33820558). Microbiome-derived inosine has also been shown to modulate the response to checkpoint inhibitor immunotherapy in cancer models. In particular, decreased gut barrier function induced by immunotherapy increases systemic translocation of bacterially derived inosine and activates antitumor T cells. The effect of inosine is dependent on T cell expression of the adenosine A2A receptor and requires co-stimulation. Inosine appears to have other roles in non-mammalian system. For instance, it has been found to be an important feed stimulant by itself or in combination with certain amino acids in some species of farmed fish. For example, inosine and inosine-5-monophosphate have been reported as specific feeding stimulants for turbot fry, (Scophthalmus maximus) and Japanese amberjack. Inosine is a purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. It has a role as a human metabolite, a Saccharomyces cerevisiae metabolite, an Escherichia coli metabolite and a mouse metabolite. It is a purines D-ribonucleoside and a member of inosines. It is functionally related to a hypoxanthine and a ribofuranose. A purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed) Inosine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Inosine is a natural product found in Fritillaria thunbergii, Cichorium endivia, and other organisms with data available. Inosine is a metabolite found in or produced by Saccharomyces cerevisiae. A purine nucleoside that has hypoxanthine linked by the N9 nitrogen to the C1 carbon of ribose. It is an intermediate in the degradation of purines and purine nucleosides to uric acid and in pathways of purine salvage. It also occurs in the anticodon of certain transfer RNA molecules. (Dorland, 28th ed) G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06B - Chemotherapeutics for topical use > D06BB - Antivirals A purine nucleoside in which hypoxanthine is attached to ribofuranose via a beta-N(9)-glycosidic bond. COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials S - Sensory organs > S01 - Ophthalmologicals Present in meat extracts and sugar beet Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS [Spectral] Inosine (exact mass = 268.08077) and L-Methionine (exact mass = 149.05105) and Adenosine (exact mass = 267.09675) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Inosine (exact mass = 268.08077) and L-Tyrosine (exact mass = 181.07389) and Guanosine (exact mass = 283.09167) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Inosine (exact mass = 268.08077) and S-Adenosyl-L-homocysteine (exact mass = 384.12159) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Inosine (exact mass = 268.08077) and Guanosine (exact mass = 283.09167) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. CONFIDENCE standard compound; INTERNAL_ID 110 KEIO_ID I003 Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3].

Uridine

C9H12N2O6 (244.0695)

Uridine, also known as beta-uridine or 1-beta-D-ribofuranosylpyrimidine-2,4(1H,3H)-dione, is a member of the class of compounds known as pyrimidine nucleosides. Pyrimidine nucleosides are compounds comprising a pyrimidine base attached to a ribosyl or deoxyribosyl moiety. More specifically, uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine is soluble (in water) and a very weakly acidic compound (based on its pKa). Uridine can be synthesized from uracil. It is one of the five standard nucleosides which make up nucleic acids, the others being adenosine, thymidine, cytidine and guanosine. The five nucleosides are commonly abbreviated to their one-letter codes U, A, T, C and G respectively. Uridine is also a parent compound for other transformation products, including but not limited to, nikkomycin Z, 3-(enolpyruvyl)uridine 5-monophosphate, and 5-aminomethyl-2-thiouridine. Uridine can be found in most biofluids, including urine, breast milk, cerebrospinal fluid (CSF), and blood. Within the cell, uridine is primarily located in the mitochondria, in the nucleus and the lysosome. It can also be found in the extracellular space. As an essential nucleoside, uridine exists in all living species, ranging from bacteria to humans. In humans, uridine is involved in several metabolic disorders, some of which include dhydropyrimidinase deficiency, MNGIE (mitochondrial neurogastrointestinal encephalopathy), and beta-ureidopropionase deficiency. Moreover, uridine is found to be associated with Lesch-Nyhan syndrome, which is an inborn error of metabolism. Uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine plays a role in the glycolysis pathway of galactose. In humans there is no catabolic process to metabolize galactose. Therefore, galactose is converted to glucose and metabolized via the normal glucose metabolism pathways. More specifically, consumed galactose is converted into galactose 1-phosphate (Gal-1-P). This molecule is a substrate for the enzyme galactose-1-phosphate uridyl transferase which transfers a UDP molecule to the galactose molecule. The end result is UDP-galactose and glucose-1-phosphate. This process is continued to allow the proper glycolysis of galactose. Uridine is found in many foods (anything containing RNA) but is destroyed in the liver and gastrointestinal tract, and so no food, when consumed, has ever been reliably shown to elevate blood uridine levels. On the other hand, consumption of RNA-rich foods may lead to high levels of purines (adenine and guanosine) in blood. High levels of purines are known to increase uric acid production and may aggravate or lead to conditions such as gout. Uridine is a ribonucleoside composed of a molecule of uracil attached to a ribofuranose moiety via a beta-N(1)-glycosidic bond. It has a role as a human metabolite, a fundamental metabolite and a drug metabolite. It is functionally related to a uracil. Uridine is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Uridine is a Pyrimidine Analog. The chemical classification of uridine is Pyrimidines, and Analogs/Derivatives. Uridine is a natural product found in Ulva australis, Synechocystis, and other organisms with data available. Uridine is a nucleoside consisting of uracil and D-ribose and a component of RNA. Uridine has been studied as a rescue agent to reduce the toxicities associated with 5-fluorouracil (5-FU), thereby allowing the administration of higher doses of 5-FU in chemotherapy regimens. (NCI04) Uridine is a metabolite found in or produced by Saccharomyces cerevisiae. A ribonucleoside in which RIBOSE is linked to URACIL. Uridine is a molecule (known as a nucleoside) that is formed when uracil is attached to a ribose ring (also known as a ribofuranose) via a b-N1-glycosidic bond. ; Uridine is a molecule (known as a nucleoside) that is formed when uracil is attached to a ribose ring (also known as a ribofuranose) via a ?-N1-glycosidic bond. Uridine is found in many foods, some of which are celery leaves, canola, common hazelnut, and hickory nut. A ribonucleoside composed of a molecule of uracil attached to a ribofuranose moiety via a beta-N(1)-glycosidic bond. [Spectral] Uridine (exact mass = 244.06954) and Adenosine (exact mass = 267.09675) and Glutathione (exact mass = 307.08381) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] Uridine (exact mass = 244.06954) and Glutathione (exact mass = 307.08381) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Uridine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=58-96-8 (retrieved 2024-06-29) (CAS RN: 58-96-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond.

Kaempferol

C15H10O6 (286.0477)

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

Quercetin

C15H10O7 (302.0427)

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

Tyrosol

C8H10O2 (138.0681)

Tyrosol is a phenolic compound present in two of the traditional components of the Mediterranean diet: wine and virgin olive oil. The presence of tyrosol has been described in red and white wines. Tyrosol is also present in vermouth and beer. Tyrosol has been shown to be able to exert antioxidant activity in vitro studies. Oxidation of low-density lipoprotein (LDL) appears to occur predominantly in arterial intimae in microdomains sequestered from antioxidants of plasma. The antioxidant content of the LDL particle is critical for its protection. The ability of tyrosol to bind human LDL has been reported. The bioavailability of tyrosol in humans from virgin olive oil in its natural form has been demonstrated. Urinary tyrosol increases, reaching a peak at 0-4 h after virgin olive oil administration. Men and women show a different pattern of urinary excretion of tyrosol. Moreover, tyrosol is absorbed in a dose-dependent manner after sustained and moderate doses of virgin olive oil. Tyrosol from wine or virgin olive oil could exert beneficial effects on human health in vivo if its biological properties are confirmed (PMID 15134375). Tyrosol is a microbial metabolite found in Bifidobacterium, Escherichia and Lactobacillus (PMID:28393285). 2-(4-hydroxyphenyl)ethanol is a phenol substituted at position 4 by a 2-hydroxyethyl group. It has a role as an anti-arrhythmia drug, an antioxidant, a cardiovascular drug, a protective agent, a fungal metabolite, a geroprotector and a plant metabolite. It is functionally related to a 2-phenylethanol. 2-(4-Hydroxyphenyl)ethanol is a natural product found in Thalictrum petaloideum, Casearia sylvestris, and other organisms with data available. Tyrosol is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Sedum roseum root (part of); Rhodiola crenulata root (part of). D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents A phenol substituted at position 4 by a 2-hydroxyethyl group. D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].

Palmitic acid

C16H32O2 (256.2402)

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

Stigmasterol

C29H48O (412.3705)

Stigmasterol is a phytosterol, meaning it is steroid derived from plants. As a food additive, phytosterols have cholesterol-lowering properties (reducing cholesterol absorption in intestines), and may act in cancer prevention. Phytosterols naturally occur in small amount in vegetable oils, especially soybean oil. One such phytosterol complex, isolated from vegetable oil, is cholestatin, composed of campesterol, stigmasterol, and brassicasterol, and is marketed as a dietary supplement. Sterols can reduce cholesterol in human subjects by up to 15\\%. The mechanism behind phytosterols and the lowering of cholesterol occurs as follows : the incorporation of cholesterol into micelles in the gastrointestinal tract is inhibited, decreasing the overall amount of cholesterol absorbed. This may in turn help to control body total cholesterol levels, as well as modify HDL, LDL and TAG levels. Many margarines, butters, breakfast cereals and spreads are now enriched with phytosterols and marketed towards people with high cholesterol and a wish to lower it. Stigmasterol is found to be associated with phytosterolemia, which is an inborn error of metabolism. Stigmasterol is a 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. It has a role as a plant metabolite. It is a 3beta-sterol, a stigmastane sterol, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. It derives from a hydride of a stigmastane. Stigmasterol is a natural product found in Ficus auriculata, Xylopia aromatica, and other organisms with data available. Stigmasterol is a steroid derivative characterized by the hydroxyl group in position C-3 of the steroid skeleton, and unsaturated bonds in position 5-6 of the B ring, and position 22-23 in the alkyl substituent. Stigmasterol is found in the fats and oils of soybean, calabar bean and rape seed, as well as several other vegetables, legumes, nuts, seeds, and unpasteurized milk. See also: Comfrey Root (part of); Saw Palmetto (part of); Plantago ovata seed (part of). Stigmasterol is an unsaturated plant sterol occurring in the plant fats or oils of soybean, calabar bean, and rape seed, and in a number of medicinal herbs, including the Chinese herbs Ophiopogon japonicus (Mai men dong) and American Ginseng. Stigmasterol is also found in various vegetables, legumes, nuts, seeds, and unpasteurized milk. A 3beta-sterol that consists of 3beta-hydroxystigmastane having double bonds at the 5,6- and 22,23-positions. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol

Friedelin

C30H50O (426.3861)

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

Isorhamnetin

C16H12O7 (316.0583)

3,4,5,7-tetrahydroxy-3-methoxyflavone is a tetrahydroxyflavone having the 4-hydroxy groups located at the 3- 4- 5- and 7-positions as well as a methoxy group at the 2-position. It has a role as a metabolite and an antimicrobial agent. It is a tetrahydroxyflavone and a monomethoxyflavone. It is functionally related to a quercetin. It is a conjugate acid of a 3,4,5-trihydroxy-3-methoxyflavon-7-olate. 3-O-Methylquercetin is a natural product found in Lotus ucrainicus, Wollastonia biflora, and other organisms with data available. See also: Tobacco Leaf (part of). 3-O-Methylquercetin (3-MQ), a main constituent of Rhamnus nakaharai, inhibits total cAMP and cGMP-phosphodiesterase (PDE) of guinea pig trachealis. 3-O-Methylquercetin (3-MQ) exhibits IC50 values ranging from 1.6-86.9 μM for PDE isozymes (PDE1-5)[1]. 3-O-Methylquercetin (3-MQ), a main constituent of Rhamnus nakaharai, inhibits total cAMP and cGMP-phosphodiesterase (PDE) of guinea pig trachealis. 3-O-Methylquercetin (3-MQ) exhibits IC50 values ranging from 1.6-86.9 μM for PDE isozymes (PDE1-5)[1].

Enmein

C20H26O6 (362.1729)

Enmein is a delta-lactone. It has a role as a metabolite. Enmein is a natural product found in Isodon oresbius, Isodon serra, and other organisms with data available. A natural product found in Isodon eriocalyx.

Adenosine monophosphate

C10H14N5O7P (347.0631)

Adenosine monophosphate, also known as adenylic acid or amp, is a member of the class of compounds known as purine ribonucleoside monophosphates. Purine ribonucleoside monophosphates are nucleotides consisting of a purine base linked to a ribose to which one monophosphate group is attached. Adenosine monophosphate is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Adenosine monophosphate can be found in a number of food items such as kiwi, taro, alaska wild rhubarb, and skunk currant, which makes adenosine monophosphate a potential biomarker for the consumption of these food products. Adenosine monophosphate can be found primarily in most biofluids, including blood, feces, cerebrospinal fluid (CSF), and urine, as well as throughout all human tissues. Adenosine monophosphate exists in all living species, ranging from bacteria to humans. In humans, adenosine monophosphate is involved in several metabolic pathways, some of which include josamycin action pathway, methacycline action pathway, nevirapine action pathway, and aspartate metabolism. Adenosine monophosphate is also involved in several metabolic disorders, some of which include hyperornithinemia-hyperammonemia-homocitrullinuria [hhh-syndrome], molybdenum cofactor deficiency, xanthinuria type I, and mitochondrial DNA depletion syndrome. Adenosine monophosphate is a drug which is used for nutritional supplementation, also for treating dietary shortage or imbalanc. Adenosine monophosphate, also known as 5-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a Bitter Blocker additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem sweeter. This potentially makes lower calorie food products more palatable. [Spectral] AMP (exact mass = 347.06308) and Guanine (exact mass = 151.04941) and 3,4-Dihydroxy-L-phenylalanine (exact mass = 197.06881) and Glutathione disulfide (exact mass = 612.15196) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] AMP (exact mass = 347.06308) and Glutathione disulfide (exact mass = 612.15196) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. [Spectral] AMP (exact mass = 347.06308) and Adenine (exact mass = 135.0545) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Adenosine monophosphate. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=67583-85-1 (retrieved 2024-07-01) (CAS RN: 61-19-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Adenosine monophosphate is a key cellular metabolite regulating energy homeostasis and signal transduction. Adenosine monophosphate is a key cellular metabolite regulating energy homeostasis and signal transduction. Adenosine monophosphate is a key cellular metabolite regulating energy homeostasis and signal transduction.

Asparagine

C4H8N2O3 (132.0535)

Asparagine (Asn) or L-asparagine is an alpha-amino acid. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon). Amino acids are organic compounds that contain amino (–NH2) and carboxyl (–COOH) functional groups, along with a side chain (R group) specific to each amino acid. L-asparagine is one of 20 proteinogenic amino acids, i.e., the amino acids used in the biosynthesis of proteins. Asparagine is found in all organisms ranging from bacteria to plants to animals. In humans, asparagine is not an essential amino acid, which means that it can be synthesized from central metabolic pathway intermediates in humans and is not required in the diet. The precursor to asparagine is oxaloacetate. Oxaloacetate is converted to aspartate using a transaminase enzyme. This enzyme transfers the amino group from glutamate to oxaloacetate producing alpha-ketoglutarate and aspartate. The enzyme asparagine synthetase produces asparagine, AMP, glutamate, and pyrophosphate from aspartate, glutamine, and ATP. In the asparagine synthetase reaction, ATP is used to activate aspartate, forming beta-aspartyl-AMP. Glutamine donates an ammonium group which reacts with beta-aspartyl-AMP to form asparagine and free AMP. Since the asparagine side chain can make efficient hydrogen bond interactions with the peptide backbone, asparagines are often found near the beginning and end of alpha-helices, and in turn motifs in beta sheets. Its role can be thought as "capping" the hydrogen bond interactions which would otherwise need to be satisfied by the polypeptide backbone. Asparagine also provides key sites for N-linked glycosylation, a modification of the protein chain that is characterized by the addition of carbohydrate chains. A reaction between asparagine and reducing sugars or reactive carbonyls produces acrylamide (acrylic amide) in food when heated to sufficient temperature (i.e. baking). These occur primarily in baked goods such as French fries, potato chips, and roasted coffee. Asparagine was first isolated in 1806 from asparagus juice --hence its name. Asparagine was the first amino acid to be isolated. The smell observed in the urine of some individuals after the consumption of asparagus is attributed to a byproduct of the metabolic breakdown of asparagine, asparagine-amino-succinic-acid monoamide. However, some scientists disagree and implicate other substances in the smell, especially methanethiol. [Spectral] L-Asparagine (exact mass = 132.05349) and L-Aspartate (exact mass = 133.03751) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. One of the nonessential amino acids. Dietary supplement, nutrient. Widely distributed in the plant kingdom. Isolated from asparagus, beetroot, peas, beans, etc. (-)-Asparagine. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=70-47-3 (retrieved 2024-07-15) (CAS RN: 70-47-3). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). L-Asparagine ((-)-Asparagine) is a non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue. L-Asparagine ((-)-Asparagine) is a non-essential amino acid that is involved in the metabolic control of cell functions in nerve and brain tissue.

Isorhamnetin

C16H12O7 (316.0583)

Isorhamnetin is the methylated metabolite of quercetin. Quercetin is an important dietary flavonoid with in vitro antioxidant activity. However, it is found in human plasma as conjugates with glucuronic acid, sulfate or methyl groups, with no significant amounts of free quercetin present. Isorhamnetin prevents endothelial cell injuries from oxidized LDL via inhibition of lectin-like ox-LDL receptor-1 upregulation, interference of ox-LDL-mediated intracellular signaling pathway (p38MAPK activation, NF-kappaB nuclear translocation, eNOS expression) and the antioxidant activity of isorhamnetin. Isorhamnetin prevents endothelial dysfunction, superoxide production, and overexpression of p47phox induced by angiotensin II. Isorhamnetin appears to be a potent drug against esophageal cancer due to its in vitro potential to not only inhibit proliferation but also induce apoptosis of Eca-109 cells. (PMID: 15493462, 17368593, 17374653, 16963021). Isorhamnetin is a monomethoxyflavone that is quercetin in which the hydroxy group at position 3 is replaced by a methoxy group. It has a role as an EC 1.14.18.1 (tyrosinase) inhibitor, an anticoagulant and a metabolite. It is a 7-hydroxyflavonol, a tetrahydroxyflavone and a monomethoxyflavone. It is functionally related to a quercetin. It is a conjugate acid of an isorhamnetin(1-). Isorhamnetin is a natural product found in Lotus ucrainicus, Strychnos pseudoquina, and other organisms with data available. Isorhamnetin is a metabolite found in or produced by Saccharomyces cerevisiae. See also: Peumus boldus leaf (part of). Widespread flavonol found especially in bee pollen, chives, corn poppy leaves, garden cress, fennel, hartwort, red onions, pears, dillweed, parsley and tarragon. Isorhamnetin is found in many foods, some of which are italian sweet red pepper, carrot, yellow wax bean, and lemon balm. A monomethoxyflavone that is quercetin in which the hydroxy group at position 3 is replaced by a methoxy group. Acquisition and generation of the data is financially supported in part by CREST/JST. Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K. Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K.

Ellagic acid

C14H6O8 (302.0063)

Ellagic acid appears as cream-colored needles (from pyridine) or yellow powder. Odorless. (NTP, 1992) Ellagic acid is an organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. It has a role as an antioxidant, a food additive, a plant metabolite, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor, an EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor, an EC 2.4.1.1 (glycogen phosphorylase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor, an EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor, an EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor, a skin lightening agent, a fungal metabolite, an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor and a geroprotector. It is an organic heterotetracyclic compound, a cyclic ketone, a lactone, a member of catechols and a polyphenol. It is functionally related to a gallic acid. Ellagic acid is present in several fruits such as cranberries, strawberries, raspberries, and pomegranates. In pomegranates, there are several therapeutic compounds but ellagic acid is the most active and abundant. Ellagic acid is also present in vegetables. Ellagic acid is an investigational drug studied for treatment of Follicular Lymphoma (phase 2 trial), protection from brain injury of intrauterine growth restricted babies (phase 1 and 2 trial), improvement of cardiovascular function in adolescents who are obese (phase 2 trial), and topical treatment of solar lentigines. Ellagic acids therapeutic action mostly involves antioxidant and anti-proliferative effects. Ellagic acid is a natural product found in Fragaria chiloensis, Metrosideros perforata, and other organisms with data available. Ellagic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A fused four ring compound occurring free or combined in galls. Isolated from the kino of Eucalyptus maculata Hook and E. Hemipholia F. Muell. Activates Factor XII of the blood clotting system which also causes kinin release; used in research and as a dye. Ellagic acid is an organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. It has a role as an antioxidant, a food additive, a plant metabolite, an EC 5.99.1.2 (DNA topoisomerase) inhibitor, an EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor, an EC 1.14.18.1 (tyrosinase) inhibitor, an EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor, an EC 2.4.1.1 (glycogen phosphorylase) inhibitor, an EC 2.5.1.18 (glutathione transferase) inhibitor, an EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor, an EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor, an EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor, a skin lightening agent, a fungal metabolite and an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor. It is an organic heterotetracyclic compound, a cyclic ketone, a lactone, a member of catechols and a polyphenol. It derives from a gallic acid. Ellagic acid, also known as ellagate, belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit. The antiproliferative and antioxidant properties of ellagic acid have spurred preliminary research into the potential health benefits of ellagic acid consumption. Ellagic acids therapeutic action mostly involves antioxidant and anti-proliferative/anti-cancer effects. Ellagic acid is found, on average, in the highest concentration within a few different foods, such as chestnuts, common walnuts, and japanese walnuts and in a lower concentration in whiskies, arctic blackberries, and cloudberries. Ellagic acid has also been detected, but not quantified in several different foods, such as lowbush blueberries, bilberries, guava, strawberry guava, and bog bilberries. An organic heterotetracyclic compound resulting from the formal dimerisation of gallic acid by oxidative aromatic coupling with intramolecular lactonisation of both carboxylic acid groups of the resulting biaryl. It is found in many fruits and vegetables, including raspberries, strawberries, cranberries, and pomegranates. Widely distributed in higher plants especies dicotyledons. Intestinal astringent, dietary role disputed. Nutriceutical with anticancer and antioxidation props. Ellagic acid is a natural antioxidant, and acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM. Ellagic acid is a natural antioxidant, and acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM.

Cyclic AMP

C10H12N5O6P (329.0525)

Cyclic amp, also known as camp or adenosine 3,5-cyclic monophosphate, is a member of the class of compounds known as 3,5-cyclic purine nucleotides. 3,5-cyclic purine nucleotides are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group. Cyclic amp is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Cyclic amp can be found in a number of food items such as green vegetables, java plum, borage, and wakame, which makes cyclic amp a potential biomarker for the consumption of these food products. Cyclic amp can be found primarily in blood, cerebrospinal fluid (CSF), feces, and urine, as well as throughout all human tissues. Cyclic amp exists in all living species, ranging from bacteria to humans. In humans, cyclic amp is involved in several metabolic pathways, some of which include dopamine activation of neurological reward system, excitatory neural signalling through 5-HTR 4 and serotonin, intracellular signalling through PGD2 receptor and prostaglandin D2, and thioguanine action pathway. Cyclic amp is also involved in several metabolic disorders, some of which include adenosine deaminase deficiency, gout or kelley-seegmiller syndrome, purine nucleoside phosphorylase deficiency, and adenine phosphoribosyltransferase deficiency (APRT). Moreover, cyclic amp is found to be associated with chronic renal failure, headache, meningitis, and hypoxic-ischemic encephalopathy. Cyclic adenosine monophosphate (cAMP, cyclic AMP, or 3,5-cyclic adenosine monophosphate) is a second messenger important in many biological processes. cAMP is a derivative of adenosine triphosphate (ATP) and used for intracellular signal transduction in many different organisms, conveying the cAMP-dependent pathway. It should not be confused with 5-AMP-activated protein kinase (AMP-activated protein kinase) . Cyclic AMP (cAMP) or cyclic adenosine monophosphate is an adenine nucleotide containing one phosphate group which is esterified to both the 3- and 5-positions of the sugar moiety. cAMP is found in all organisms ranging from bacteria to plants to animals. In humans and other mammals it is a second messenger and a key intracellular regulator, functioning as a mediator of activity for a number of hormones, including epinephrine, glucagon and ACTH. cAMP is synthesized from ATP by adenylate cyclase. Adenylate cyclase is located at the inner side of cell membranes. Adenylate cyclase is activated by the hormones glucagon and adrenaline and by G protein. Liver adenylate cyclase responds more strongly to glucagon, and muscle adenylate cyclase responds more strongly to adrenaline. cAMP decomposition into AMP is catalyzed by the enzyme phosphodiesterase. cAMP is primarily used for intracellular signal transduction, such as transferring into cells the effects of hormones like glucagon and adrenaline, which cannot pass through the plasma membrane. cAMP is also involved in the activation of protein kinases. In addition, cAMP binds to and regulates the function of ion channels such as the HCN channels. Hyperpolarization-activated cyclic nucleotide–gated (HCN) channels are integral membrane proteins that serve as nonselective voltage-gated cation channels in the plasma membranes of heart and brain cells. HCN channels are sometimes referred to as pacemaker channels because they help to generate rhythmic activity within groups of heart and brain cells. [Spectral] 3,5-Cyclic AMP (exact mass = 329.05252) and Guanosine (exact mass = 283.09167) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3]. Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3]. Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3].

Tricin

C17H14O7 (330.0739)

[Raw Data] CBA24_Tricin_neg_50eV_1-6_01_1424.txt [Raw Data] CBA24_Tricin_pos_50eV_1-6_01_1397.txt [Raw Data] CBA24_Tricin_neg_10eV_1-6_01_1368.txt [Raw Data] CBA24_Tricin_pos_40eV_1-6_01_1396.txt [Raw Data] CBA24_Tricin_pos_20eV_1-6_01_1394.txt [Raw Data] CBA24_Tricin_neg_30eV_1-6_01_1422.txt [Raw Data] CBA24_Tricin_neg_20eV_1-6_01_1421.txt [Raw Data] CBA24_Tricin_pos_10eV_1-6_01_1357.txt [Raw Data] CBA24_Tricin_pos_30eV_1-6_01_1488.txt [Raw Data] CBA24_Tricin_neg_40eV_1-6_01_1423.txt Tricin is a natural flavonoid present in large amounts in Triticum aestivum. Tricin can inhibit human cytomegalovirus (HCMV) replication by inhibiting CDK9. Tricin inhibits the proliferation and invasion of C6 glioma cells via the upregulation of focal-adhesion-finase (FAK)-targeting microRNA-7[1][2][3]. Tricin is a natural flavonoid present in large amounts in Triticum aestivum. Tricin can inhibit human cytomegalovirus (HCMV) replication by inhibiting CDK9. Tricin inhibits the proliferation and invasion of C6 glioma cells via the upregulation of focal-adhesion-finase (FAK)-targeting microRNA-7[1][2][3].

Cholesterol

C27H46O (386.3548)

Cholesterol is a sterol (a combination steroid and alcohol) and a lipid found in the cell membranes of all body tissues and transported in the blood plasma of all animals. The name originates from the Greek chole- (bile) and stereos (solid), and the chemical suffix -ol for an alcohol. This is because researchers first identified cholesterol in solid form in gallstones in 1784. In the body, cholesterol can exist in either the free form or as an ester with a single fatty acid (of 10-20 carbons in length) covalently attached to the hydroxyl group at position 3 of the cholesterol ring. Due to the mechanism of synthesis, plasma cholesterol esters tend to contain relatively high proportions of polyunsaturated fatty acids. Most of the cholesterol consumed as a dietary lipid exists as cholesterol esters. Cholesterol esters have a lower solubility in water than cholesterol and are more hydrophobic. They are hydrolyzed by the pancreatic enzyme cholesterol esterase to produce cholesterol and free fatty acids. Cholesterol has vital structural roles in membranes and in lipid metabolism in general. It is a biosynthetic precursor of bile acids, vitamin D, and steroid hormones (glucocorticoids, estrogens, progesterones, androgens and aldosterone). In addition, it contributes to the development and functioning of the central nervous system, and it has major functions in signal transduction and sperm development. Cholesterol is a ubiquitous component of all animal tissues where much of it is located in the membranes, although it is not evenly distributed. The highest proportion of unesterified cholesterol is in the plasma membrane (roughly 30-50\\\\% of the lipid in the membrane or 60-80\\\\% of the cholesterol in the cell), while mitochondria and the endoplasmic reticulum have very low cholesterol contents. Cholesterol is also enriched in early and recycling endosomes, but not in late endosomes. The brain contains more cholesterol than any other organ where it comprises roughly a quarter of the total free cholesterol in the human body. Of all the organic constituents of blood, only glucose is present in a higher molar concentration than cholesterol. Cholesterol esters appear to be the preferred form for transport in plasma and as a biologically inert storage (de-toxified) form. They do not contribute to membranes but are packed into intracellular lipid particles. Cholesterol molecules (i.e. cholesterol esters) are transported throughout the body via lipoprotein particles. The largest lipoproteins, which primarily transport fats from the intestinal mucosa to the liver, are called chylomicrons. They carry mostly triglyceride fats and cholesterol that are from food, especially internal cholesterol secreted by the liver into the bile. In the liver, chylomicron particles give up triglycerides and some cholesterol. They are then converted into low-density lipoprotein (LDL) particles, which carry triglycerides and cholesterol on to other body cells. In healthy individuals, the LDL particles are large and relatively few in number. In contrast, large numbers of small LDL particles are strongly associated with promoting atheromatous disease within the arteries. (Lack of information on LDL particle number and size is one of the major problems of conventional lipid tests.). In conditions with elevated concentrations of oxidized LDL particles, especially small LDL particles, cholesterol promotes atheroma plaque deposits in the walls of arteries, a condition known as atherosclerosis, which is a major contributor to coronary heart disease and other forms of cardiovascular disease. There is a worldwide trend to believe that lower total cholesterol levels tend to correlate with lower atherosclerosis event rates (though some studies refute this idea). As a result, cholesterol has become a very large focus for the scientific community trying to determine the proper amount of cholesterol needed in a healthy diet. However, the primary association of atherosclerosis with c... Constituent either free or as esters, of fish liver oils, lard, dairy fats, egg yolk and bran Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

Isodonal

C22H28O7 (404.1835)

Methyl benzoate

C8H8O2 (136.0524)

Methyl benzoate is an ester with the chemical formula C6H5COOCH3. It is formed by the condensation of methanol and benzoic acid. It is a colorless to slightly yellow liquid that is insoluble with water, but miscible with most organic solvents. Methyl benzoate is found in allspice. Methyl benzoate is present in various flower oils, banana, cherry, pimento berry, ceriman (Monstera deliciosa), clove bud and stem, mustard, coffee, black tea, dill, starfruit and cherimoya (Annona cherimola). Methyl benzoate is used in flavourings. It is one of many compounds that is attractive to males of various species of orchid bees, who apparently gather the chemical to synthesize pheromones; it is commonly used as bait to attract and collect these bees for study. Present in various flower oils, banana, cherry, pimento berry, ceriman (Monstera deliciosa), clove bud and stem, mustard, coffee, black tea, dill, starfruit and cherimoya (Annona cherimola). It is used in flavourings

DL-Asparagine

C4H8N2O3 (132.0535)

DL-Asparagine is a racemic melange of the Aparagine L and D-enantiomers. DL-Asparagine has been used in growth-media for bacteria-growth[1]. DL-Asparagine is a racemic melange of the Aparagine L and D-enantiomers. DL-Asparagine has been used in growth-media for bacteria-growth[1].

Pentacosane

C25H52 (352.4069)

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].

L,L-Cyclo(leucylprolyl)

C11H18N2O2 (210.1368)

L,L-Cyclo(leucylprolyl) is found in alcoholic beverages. L,L-Cyclo(leucylprolyl) is produced by microorganisms and is a bitter component of sake and contributes to the flavour of beer. L,L-Cyclo(leucylprolyl), also known as cyclo(leu-pro) or cyclo(L-prolyl-L-leucyl), belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof. L,L-Cyclo(leucylprolyl) is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on L,L-Cyclo(leucylprolyl). L-Leucyl-L-proline lactam. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=2873-36-1 (retrieved 2024-07-10) (CAS RN: 2873-36-1). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Cyclo(L-Leu-L-Pro) is an inhibitory substance targeting to production of norsolorinic acid (NA，a precursor of aflatoxin)，which can be isolated from A. xylosoxidans NFRI-A1. Cyclo(L-Leu-L-Pro) inhibits accumulation of NA by A. parasiticus NFRI-95 and inhibits spore formation. Cyclo(L-Leu-L-Pro) inhibits aflatoxin production with an IC50 of 0.2 mg/mL in A. parasiticus SYS-4[1].

2-Nonenal

C9H16O (140.1201)

(E)-2-Nonenal is found in alcoholic beverages. (E)-2-Nonenal is widespread in nature, in beer, coffee, watermelon, cucumbers, redcurrants, orris oil, palm oil, potatoes etc. (E)-2-Nonenal is a flavouring ingredien. It has also been identified as a uremic toxin according to the European Uremic Toxin Working Group (PMID:22626821). 2-Nonenal is an unsaturated aldehyde which some research has associated with human body odor alterations during aging. The substance is also an important aroma component of aged beer and buckwheat. The odor of this substance is perceived as orris, fat and cucumber. 2-Nonenal is found in lemon.

4-Methyloctanoic acid

C9H18O2 (158.1307)

(±)-4-Methyloctanoic acid is a flavouring ingredien Flavouring ingredient 4-Methyloctanoic acid is a natural compound mainly responsible for the characteristic goaty sheepy flavour of sheep and goat milk[1].

Eicosane

C20H42 (282.3286)

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.

2-Nonen-1-ol

C9H18O (142.1358)

2-Nonen-1-ol is found in alcoholic beverages. 2-Nonen-1-ol is used in food flavouring. 2-Nonen-1-ol is present in melon, cucumber, chicken fat, armagnac, brown algae, nectarine and prickly pear (Opuntia ficus Indica). 2-Nonen-1-ol is used in food flavouring. It is found in melon, cucumber, chicken fat, armagnac, brown algae, nectarine and prickly pear (Opuntia ficus Indica).

Oridonin

C20H28O6 (364.1886)

Vidarabine phosphate

C10H14N5O7P (347.0631)

Adenosine monophosphate, also known as 5-adenylic acid and abbreviated AMP, is a nucleotide that is found in RNA. It is an ester of phosphoric acid with the nucleoside adenosine. AMP consists of the phosphate group, the pentose sugar ribose, and the nucleobase adenine. AMP can be produced during ATP synthesis by the enzyme adenylate kinase. AMP has recently been approved as a Bitter Blocker additive to foodstuffs. When AMP is added to bitter foods or foods with a bitter aftertaste it makes them seem sweeter. This potentially makes lower calorie food products more palatable [HMDB] Adenosine monophosphate is a key cellular metabolite regulating energy homeostasis and signal transduction. Adenosine monophosphate is a key cellular metabolite regulating energy homeostasis and signal transduction. Adenosine monophosphate is a key cellular metabolite regulating energy homeostasis and signal transduction.

1-[(2R,3S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

C9H12N2O6 (244.0695)

1-beta-D-Arabinofuranosyluracil (Uracil 1-β-D-arabinofuranoside) isolated from the Caribbean sponge Tectitethya crypta, is a methoxyadenosine derivative. 1-beta-D-Arabinofuranosyluracil has demonstrated a diverse bioactivity profile including anti-inflammatory activity, analgesic and vasodilation properties[1]. 1-beta-D-Arabinofuranosyluracil reduces a proliferation of mouse lymphoma cells[2]. 1-beta-D-Arabinofuranosyluracil (Uracil 1-β-D-arabinofuranoside) isolated from the Caribbean sponge Tectitethya crypta, is a methoxyadenosine derivative. 1-beta-D-Arabinofuranosyluracil has demonstrated a diverse bioactivity profile including anti-inflammatory activity, analgesic and vasodilation properties[1]. 1-beta-D-Arabinofuranosyluracil reduces a proliferation of mouse lymphoma cells[2]. 1-beta-D-Arabinofuranosyluracil (Uracil 1-β-D-arabinofuranoside) isolated from the Caribbean sponge Tectitethya crypta, is a methoxyadenosine derivative. 1-beta-D-Arabinofuranosyluracil has demonstrated a diverse bioactivity profile including anti-inflammatory activity, analgesic and vasodilation properties[1]. 1-beta-D-Arabinofuranosyluracil reduces a proliferation of mouse lymphoma cells[2].

Ara-HX

C10H12N4O5 (268.0808)

9-Arabinofuranosyladenine

C10H13N5O4 (267.0967)

Epi-Friedelanol

C30H52O (428.4018)

Friedelin

C30H50O (426.3861)

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

Nodosin

C20H26O6 (362.1729)

Hentriacontan-16-ol

C31H64O (452.4957)

Hentriacontan-16-ol is a member of the class of compounds known as long-chain fatty alcohols. Long-chain fatty alcohols are fatty alcohols that have an aliphatic tail of 13 to 21 carbon atoms. Thus, hentriacontan-16-ol is considered to be a fatty alcohol lipid molecule. Hentriacontan-16-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Hentriacontan-16-ol can be found in common pea and pepper (spice), which makes hentriacontan-16-ol a potential biomarker for the consumption of these food products.

Inosine

C10H12N4O5 (268.0808)

G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06B - Chemotherapeutics for topical use > D06BB - Antivirals COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3].

Uridine

C9H12N2O6 (244.0695)

C26170 - Protective Agent > C2459 - Chemoprotective Agent > C2080 - Cytoprotective Agent COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond.

Oridonin

C20H28O6 (364.1886)

Oridonin is an organic heteropentacyclic compound and ent-kaurane diterpenoid with formula C20H28O6 isolated from the leaves of the medicinal herb Rabdosia rubescens. It has a role as an antineoplastic agent, an angiogenesis inhibitor, an apoptosis inducer, an anti-asthmatic agent, a plant metabolite and an antibacterial agent. It is an organic heteropentacyclic compound, an enone, a cyclic hemiketal, a secondary alcohol and an ent-kaurane diterpenoid. Oridonin is a natural product found in Isodon rugosus, Isodon ternifolius, and other organisms with data available. An organic heteropentacyclic compound and ent-kaurane diterpenoid with formula C20H28O6 isolated from the leaves of the medicinal herb Rabdosia rubescens. Oridonin (NSC-250682), a diterpenoid isolated from Rabdosia rubescens, acts as an inhibitor of AKT, with IC50s of 8.4 and 8.9 μM for AKT1 and AKT2; Oridonin possesses anti-tumor, anti-bacterial and anti-inflammatory effects. Oridonin (NSC-250682), a diterpenoid isolated from Rabdosia rubescens, acts as an inhibitor of AKT, with IC50s of 8.4 and 8.9 μM for AKT1 and AKT2; Oridonin possesses anti-tumor, anti-bacterial and anti-inflammatory effects. Oridonin (NSC-250682), a diterpenoid isolated from Rabdosia rubescens, acts as an inhibitor of AKT, with IC50s of 8.4 and 8.9 μM for AKT1 and AKT2; Oridonin possesses anti-tumor, anti-bacterial and anti-inflammatory effects. Oridonin (NSC-250682), a diterpenoid isolated from Rabdosia rubescens, acts as an inhibitor of AKT, with IC50s of 8.4 and 8.9 μM for AKT1 and AKT2; Oridonin possesses anti-tumor, anti-bacterial and anti-inflammatory effects.

Adenolin A

C25H36O9 (480.2359)

A natural product found in Isodon adenolomus.

Palmitic Acid

C16H32O2 (256.2402)

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

METHYL BENZOATE

C8H8O2 (136.0524)

A benzoate ester obtained by condensation of benzoic acid and methanol.

sitosterol

C29H50O (414.3861)

A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3. C1907 - Drug, Natural Product > C28178 - Phytosterol > C68437 - Unsaturated Phytosterol D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents D009676 - Noxae > D000963 - Antimetabolites Beta-Sitosterol (purity>98\\%) is a plant sterol. Beta-Sitosterol (purity>98\\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1]. Beta-Sitosterol (purity>98\%) is a plant sterol. Beta-Sitosterol (purity>98\%) interfere with multiple cell signaling pathways, including cell cycle, apoptosis, proliferation, survival, invasion, angiogenesis, metastasis and inflammation[1].

Stigmasterol

C29H48O (412.3705)

Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong.

Quercetin

C15H10O7 (302.0427)

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

Isorhamnetin

C16H12O7 (316.0583)

Glucoside present in the leaves of Peumus boldus (boldo). Isorhamnetin 3-dirhamnoside is found in fruits. Annotation level-1 Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K. Isorhamnetin is a flavonoid compound extracted from the Chinese herb Hippophae rhamnoides L.. Isorhamnetin suppresses skin cancer through direct inhibition of MEK1 and PI3K.

Tricin

C17H14O7 (330.0739)

3,5-di-O-methyltricetin is the 3,5-di-O-methyl ether of tricetin. Known commonly as tricin, it is a constituent of rice bran and has been found to potently inhibit colon cancer cell growth. It has a role as an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor and a metabolite. It is a trihydroxyflavone, a dimethoxyflavone and a member of 3-methoxyflavones. It is functionally related to a tricetin. It is a conjugate acid of a 3,5-di-O-methyltricetin(1-). Tricin is a natural product found in Carex fraseriana, Smilax bracteata, and other organisms with data available. See also: Arnica montana Flower (part of); Elymus repens root (part of). The 3,5-di-O-methyl ether of tricetin. Known commonly as tricin, it is a constituent of rice bran and has been found to potently inhibit colon cancer cell growth. Isolated from Triticum dicoccum (emmer). Tricin 5-diglucoside is found in wheat and cereals and cereal products. From leaves of Oryza sativa (rice). 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one, also known as 3,5-O-dimethyltricetin or 5,7,4-trihydroxy-3,5-dimethoxy-flavone, is a member of the class of compounds known as 3-o-methylated flavonoids. 3-o-methylated flavonoids are flavonoids with methoxy groups attached to the C3 atom of the flavonoid backbone. Thus, 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is considered to be a flavonoid lipid molecule. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one can be synthesized from tricetin. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one is also a parent compound for other transformation products, including but not limited to, tricin 7-O-glucoside, 4-O-beta-glucosyl-7-O-(6-O-sinapoylglucosyl)tricin, and tricin 7-O-(6-O-malonyl)-beta-D-glucopyranoside. 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one can be found in barley, common wheat, oat, and rice, which makes 5,7-dihydroxy-2-(4-hydroxy-3,5-dimethoxyphenyl)-4h-chromen-4-one a potential biomarker for the consumption of these food products. Tricin is a natural flavonoid present in large amounts in Triticum aestivum. Tricin can inhibit human cytomegalovirus (HCMV) replication by inhibiting CDK9. Tricin inhibits the proliferation and invasion of C6 glioma cells via the upregulation of focal-adhesion-finase (FAK)-targeting microRNA-7[1][2][3]. Tricin is a natural flavonoid present in large amounts in Triticum aestivum. Tricin can inhibit human cytomegalovirus (HCMV) replication by inhibiting CDK9. Tricin inhibits the proliferation and invasion of C6 glioma cells via the upregulation of focal-adhesion-finase (FAK)-targeting microRNA-7[1][2][3].

Sorbicillin

C14H16O3 (232.1099)

4,6,8,10,16,18-Hexamethyldocosane

C28H58 (394.4538)

bisvertinoquinol

C28H34O8 (498.2254)

Dihydrosterculic acid

C19H36O2 (296.2715)

PENTACOS-9-ENE

C25H50 (350.3912)

Cholesterol

C27H46O (386.3548)

A cholestanoid consisting of cholestane having a double bond at the 5,6-position as well as a 3beta-hydroxy group. Disclaimer: While authors make an effort to ensure that the content of this record is accurate, the authors make no representations or warranties in relation to the accuracy or completeness of the record. This record do not reflect any viewpoints of the affiliation and organization to which the authors belong. Cholesterol is the major sterol in mammals. It is making up 20-25\\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3]. Cholesterol is the major sterol in mammals. It is making up 20-25\% of structural component of the plasma membrane. Plasma membranes are highly permeable to water but relatively impermeable to ions and protons. Cholesterol plays an important role in determining the fluidity and permeability characteristics of the membrane as well as the function of both the transporters and signaling proteins[1][2]. Cholesterol is also an endogenous estrogen-related receptor α (ERRα) agonist[3].

6-(2,4-dihydroxy-5-methylphenyl)-6-oxohexanoic acid

C13H16O5 (252.0998)

hentriacontan-16-ol

C31H64O (452.4957)

A fatty alcohol consisting of a hydroxy function at C-16 of an unbranched saturated chain of 31 carbon atoms.

4,6,8,10,16-Pentamethyldocosane

C27H56 (380.4382)

Pentacosane

C25H52 (352.4069)

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].

Adenosine

C10H13N5O4 (267.0967)

COVID info from PDB, Protein Data Bank, COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058913 - Purinergic Agonists D018373 - Peripheral Nervous System Agents > D018689 - Sensory System Agents D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D002491 - Central Nervous System Agents > D000700 - Analgesics D002317 - Cardiovascular Agents > D014665 - Vasodilator Agents C - Cardiovascular system > C01 - Cardiac therapy Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Formula(Parent): C10H13N5O4; Bottle Name:Adenosine; PRIME Parent Name:Adenosine; PRIME in-house No.:0040 R0018, Purines MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; OIRDTQYFTABQOQ_STSL_0143_Adenosine_0500fmol_180430_S2_LC02_MS02_33; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.113 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.109 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.097 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.096 Acquisition and generation of the data is financially supported by the Max-Planck-Society IPB_RECORD: 2621; CONFIDENCE confident structure Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2]. Adenosine (Adenine riboside), a ubiquitous endogenous autacoid, acts through the enrollment of four G protein-coupled receptors: A1, A2A, A2B, and A3. Adenosine affects almost all aspects of cellular physiology, including neuronal activity, vascular function, platelet aggregation, and blood cell regulation[1][2].

Inosine

C10H12N4O5 (268.0808)

G - Genito urinary system and sex hormones > G01 - Gynecological antiinfectives and antiseptics > G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids D - Dermatologicals > D06 - Antibiotics and chemotherapeutics for dermatological use > D06B - Chemotherapeutics for topical use > D06BB - Antivirals Formula(Parent): C10H12N4O5; Bottle Name:Inosine; PRIME Parent Name:Inosine; PRIME in-house No.:0256, Purines COVID info from COVID-19 Disease Map, clinicaltrial, clinicaltrials, clinical trial, clinical trials S - Sensory organs > S01 - Ophthalmologicals Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; UGQMRVRMYYASKQ_STSL_0164_Inosine_2000fmol_180430_S2_LC02_MS02_125; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.054 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.053 Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3]. Inosine is an endogenous purine nucleoside produced by catabolism of adenosine. Inosine has anti-inflammatory, antinociceptive, immunomodulatory and neuroprotective effects. Inosine is an agonist for adenosine A1 (A1R) and A2A (A2AR) receptors[1][2][3].

Uridine

C9H12N2O6 (244.0695)

C26170 - Protective Agent > C2459 - Chemoprotective Agent > C2080 - Cytoprotective Agent COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; DRTQHJPVMGBUCF_STSL_0179_Uridine_8000fmol_180506_S2_LC02_MS02_83; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. MS2 deconvoluted using CorrDec from all ion fragmentation data, MetaboLights identifier MTBLS1040; Spectrum acquired as described in Naz et al 2017 PMID 28641411. Preparation and submission to MassBank of North America by Chaleckis R. and Tada I. relative retention time with respect to 9-anthracene Carboxylic Acid is 0.088 Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond. Uridine (β-Uridine) is a glycosylated pyrimidine-analog containing uracil attached to a ribose ring (or more specifically, aribofuranose) via a β-N1-glycosidic bond.

Ellagic Acid

C14H6O8 (302.0063)

Origin: Plant, Ellagic acids, Benzopyranoids, Pyrans Ellagic acid is a natural antioxidant, and acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM. Ellagic acid is a natural antioxidant, and acts as a potent and ATP-competitive CK2 inhibitor, with an IC50 of 40 nM and a Ki of 20 nM.

cyclic amp

C10H12N5O6P (329.0525)

COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS CONFIDENCE standard compound; INTERNAL_ID 127 Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3]. Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3]. Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3].

Sucrose

C12H22O11 (342.1162)

D000074385 - Food Ingredients > D005503 - Food Additives D010592 - Pharmaceutic Aids > D005421 - Flavoring Agents COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

5-Methyluridine

C10H14N2O6 (258.0852)

CONFIDENCE standard compound; INTERNAL_ID 320 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids. 5-Methyluridine is a is an endogenous methylated nucleoside found in human fluids.

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266)

5-Methyluridine

C10H15N3O5 (257.1012)

Adenosine monophosphate

C10H14N5O7P (347.0631)

Hexadecanoic acid

C16H32O2 (256.2402)

16-hentriacontanol

C31H64O (452.4957)

(2E)-2-Nonenal

C9H16O (140.1201)

Coriandrol

C10H18O (154.1358)

3-Methylpentacosane

C26H54 (366.4225)

FOH 31:0

C31H64O (452.4957)

2-phenylacetonitrile

C8H7N (117.0578)

Farnesene

C15H24 (204.1878)

Isol. (without stereochemical distinction) from oil of Cymbopogon nardus (citronella), Cananga odorata (ylang ylang) and others (E)-β-Farnesene (trans-β-Farnesene) is a volatile sesquiterpene hydrocarbon which can be found in Phlomis aurea Decne essential oil. (E)-β-Farnesene can be used as a feeding stimulant for the sand fly Lutzomyia longipalpis[1][2]. (E)-β-Farnesene (trans-β-Farnesene) is a volatile sesquiterpene hydrocarbon which can be found in Phlomis aurea Decne essential oil. (E)-β-Farnesene can be used as a feeding stimulant for the sand fly Lutzomyia longipalpis[1][2].

GALOP

C7H6O5 (170.0215)

C26170 - Protective Agent > C275 - Antioxidant Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2]. Gallic acid (3,4,5-Trihydroxybenzoic acid) is a natural polyhydroxyphenolic compound and an free radical scavenger to inhibit cyclooxygenase-2 (COX-2)[1]. Gallic acid has various activities, such as antimicrobial, antioxidant, antimicrobial, anti-inflammatory, and anticance activities[2].

Pirod

C4H4N2O2 (112.0273)

COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA. Uracil is a common and naturally occurring pyrimidine derivative and one of the four nucleobases in the nucleic acid of RNA.

Tyrosol

C8H10O2 (138.0681)

Tyrosol, also known as 4-hydroxyphenylethanol or 4-(2-hydroxyethyl)phenol, is a member of the class of compounds known as tyrosols. Tyrosols are organic aromatic compounds containing a phenethyl alcohol moiety that carries a hydroxyl group at the 4-position of the benzene group. Tyrosol is soluble (in water) and a very weakly acidic compound (based on its pKa). Tyrosol can be synthesized from 2-phenylethanol. Tyrosol is also a parent compound for other transformation products, including but not limited to, hydroxytyrosol, crosatoside B, and oleocanthal. Tyrosol is a mild, sweet, and floral tasting compound and can be found in a number of food items such as breadnut tree seed, sparkleberry, loquat, and savoy cabbage, which makes tyrosol a potential biomarker for the consumption of these food products. Tyrosol can be found primarily in feces and urine, as well as in human prostate tissue. Tyrosol exists in all eukaryotes, ranging from yeast to humans. Tyrosol present in wine is also shown to be cardioprotective. Samson et al. has shown that tyrosol-treated animals showed significant increase in the phosphorylation of Akt, eNOS and FOXO3a. In addition, tyrosol also induced the expression of longevity protein SIRT1 in the heart after myocardial infarction in a rat MI model. Hence tyrosols SIRT1, Akt and eNOS activating power adds another dimension to the wine research, because it adds a great link to the French paradox. In conclusion these findings suggest that tyrosol induces myocardial protection against ischemia related stress by inducing survival and longevity proteins that may be considered as anti-aging therapy for the heart . D002317 - Cardiovascular Agents > D000889 - Anti-Arrhythmia Agents D020011 - Protective Agents > D000975 - Antioxidants Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1]. Tyrosol is a derivative of phenethyl alcohol. Tyrosol attenuates pro-inflammatory cytokines from cultured astrocytes and NF-κB activation. Anti-oxidative and anti-inflammatory effects[1].

hentriacontan-16-ol

C31H64O (452.4957)

2-nonenal

C9H16O (140.1201)

2-amino-3-(2-methylidenecyclopropyl)propanoic acid

C7H11NO2 (141.079)

Adenolin B

C22H30O8 (422.1941)

A natural product found in Isodon adenolomus.

Hypoglycine a

C7H11NO2 (141.079)

D009676 - Noxae > D011042 - Poisons > D007005 - Hypoglycins

Cyclic adenosine monophosphate

C10H12N5O6P (329.0525)

cAMP. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=60-92-4 (retrieved 2024-07-02) (CAS RN: 60-92-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3]. Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3]. Cyclic AMP (Cyclic adenosine monophosphate), adenosine triphosphate derivative, is an intracellular signaling molecule responsible for directing cellular responses to extracellular signals. Cyclic AMP is an important second messenger in many biological processes[1][2][3].

[(1s,2r,6s)-2-hydroxy-6-(11-hydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl)-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (3s)-3-hydroxybutanoate

C26H40O7 (464.2774)

(1r,2s,4r,5r,7r,8s,9s,10s,11r)-4,7,9-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-10-yl acetate

C22H32O6 (392.2199)

2-{[2-({2-[(2-{[1,3-dihydroxy-2-({1-hydroxy-2-[(1-hydroxyethylidene)amino]-2-methylpropylidene}amino)propylidene]amino}-1-hydroxypropylidene)amino]-1-hydroxy-2-methylpropylidene}amino)-1-hydroxy-2-methylpropylidene]amino}-n-[1-({1-[(1-{[({1-[(1-{2-[(1-{[1-({1-[(1-{[1-hydroxy-3-(4-hydroxyphenyl)propan-2-yl]-c-hydroxycarbonimidoyl}-3-(c-hydroxycarbonimidoyl)propyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-c-hydroxycarbonimidoyl)-1-methylethyl]-c-hydroxycarbonimidoyl}-3-methylbutyl)-c-hydroxycarbonimidoyl]pyrrolidin-1-yl}-2-methyl-1-oxopropan-2-yl)-c-hydroxycarbonimidoyl]-3-methylbutyl}-c-hydroxycarbonimidoyl)methyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl}-c-hydroxycarbonimidoyl)-1-methylethyl]pentanediimidic acid

C83H138N20O23 (1783.0243)

(1r,2r,7r,8r,10s,11z)-5,10-dihydroxy-11-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-8,10-dimethyl-3-oxatricyclo[6.2.2.0²,⁷]dodec-5-ene-4,9,12-trione

C19H20O7 (360.1209)

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

C29H48O (412.3705)

(1's,3r,3ar,4s,5r,6'r,7'r,7ar,9's)-5,7'-dihydroxy-7a-methyl-10'-methylidene-2',11'-dioxo-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecan]-3-yl acetate

C22H28O8 (420.1784)

3,7-dihydroxy-1-(hydroxymethyl)-9-methoxybenzo[c]chromen-6-one

C15H12O6 (288.0634)

(1r,6r,9s,10s)-6,10-dihydroxy-15-methyl-8,16-dioxatricyclo[7.7.1.0²,⁷]heptadec-2(7)-en-3-one

C16H24O5 (296.1624)

2-hydroxy-n-(3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadeca-4,8-dien-2-yl)hexadecanimidic acid

C40H75NO9 (713.5442)

15-(5,6-dimethylhept-3-en-2-yl)-5,10-dihydroxy-2-methyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-11-ene-16-carboxylic acid

C28H42O5 (458.3032)

(2r,5s)-5-hydroxy-2-[(1e)-oct-1-en-1-yl]-3,5,6,7-tetrahydro-2h-1-benzofuran-4-one

C16H24O3 (264.1725)

2-(4-{1-hydroxy-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-4-yl}phenoxy)-5-(hydroxymethyl)oxolane-3,4-diol

C26H33NO7 (471.2257)

[3-(acetyloxy)-9,10-dihydroxy-6-(methoxymethyl)-12-methyl-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-12-yl]methyl acetate

C25H36O9 (480.2359)

4,8,14,15,15-pentamethyltetracyclo[9.3.1.0¹,⁹.0⁵,⁸]pentadec-4-en-6-one

C20H30O (286.2297)

2-(2-methylpropyl)-5-phenyl-1h-pyrrole

C14H17N (199.1361)

(1s,5r,6s)-1-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

C22H30O5 (374.2093)

(1s,3s,4r,6s,8r,9r,10s,11r,13s)-3,8,11-trihydroxy-5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl acetate

C22H32O6 (392.2199)

n-[1-({1-[2-({2-hydroxy-1-[(1-{[1-(2-{[1-({1-[(1-{2-[(1-hydroxy-3-methylbutan-2-yl)-c-hydroxycarbonimidoyl]pyrrolidin-1-yl}-2-methyl-1-oxopropan-2-yl)-c-hydroxycarbonimidoyl]-3-methylbutyl}-c-hydroxycarbonimidoyl)-1-methylethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl)-2-methyl-1-oxopropan-2-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl)-c-hydroxycarbonimidoyl]ethyl}-c-hydroxycarbonimidoyl)pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl}-c-hydroxycarbonimidoyl)-3-methylbutyl]-2-({1-hydroxy-2-[(1-hydroxyethylidene)amino]-2-methylpropylidene}amino)pentanediimidic acid

C68H117N15O17 (1415.8751)

6-hydroxy-2-(1-hydroxy-6-oxoheptyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one

C16H24O5 (296.1624)

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

C27H30O15 (594.1585)

4,12,18,19-tetrahydroxy-13-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-6-methylpentacyclo[8.7.4.0¹,¹⁰.0³,⁸.0¹¹,¹⁶]henicosa-3,5,7,11(16),12,20-hexaene-2,9,14,15-tetrone

C37H40O9 (628.2672)

(1s,5r,6s)-5-hydroxy-1-(11-hydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl)-4-methyl-7-oxabicyclo[4.1.0]hept-3-en-2-one

C22H34O4 (362.2457)

4-(1-hydroxyhex-4-en-1-yl)-3-methyl-5h-furan-2-one

C11H16O3 (196.1099)

(1s)-7,8-dihydroxy-6-methoxy-1-pentyl-1,4-dihydro-2-benzopyran-3-one

C15H20O5 (280.1311)

({5-[(1e)-2-carboxyeth-1-en-1-yl]-6-oxabicyclo[3.1.0]hex-2-en-3-yl}amino)methylidene

C9H9NO3 (179.0582)

1-hydroxy-3-(2-methylpropyl)-3h,6h,7h,8h,8ah-pyrrolo[1,2-a]pyrazin-4-one

C11H18N2O2 (210.1368)

7-acetyl-1,3,6-trihydroxyanthracene-9,10-dione

C16H10O6 (298.0477)

(1r,4s,5z,7r,8s)-7-[(4e)-hex-4-enoyl]-3-hydroxy-8-[(2s)-3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl]-5-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione

C28H34O8 (498.2254)

(1r,2s,5r,7r,8s,9s,10s,11r)-7,9-dihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-10-yl acetate

C22H32O5 (376.225)

[(1r,6s)-6-{[(1s,4as,8as)-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (3s)-3-hydroxybutanoate

C26H36O6 (444.2512)

7-hydroxy-7-(6-hydroxy-5-oxo-2,3,4,6,7,8-hexahydro-1-benzopyran-2-yl)heptanoic acid

C16H24O6 (312.1573)

(1r,2s,3r,5s,6r,8r,9r,10s,11s,12r)-8,10-dihydroxy-13,13-dimethyl-7-methylidene-4,18-dioxahexacyclo[8.6.2.1⁶,⁹.0¹,¹².0²,⁹.0³,⁵]nonadecan-11-yl acetate

C22H30O6 (390.2042)

methyl 1-({[5-({[2-(methoxycarbonyl)pyrrolidin-1-yl]imino}methyl)furan-2-yl]methylidene}amino)pyrrolidine-2-carboxylate

C18H24N4O5 (376.1747)

(1r,1's,2r,6's,7'r,9's)-7'-hydroxy-3,3-dimethyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecane]-2-carbaldehyde

C20H26O5 (346.178)

(2s,6s)-6-hydroxy-2-[(1s)-1-hydroxy-6-oxoheptyl]-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one

C16H24O5 (296.1624)

n-{1-[({[1-({1-[({[({1-[(1-{[({1-[(1-hydroxy-4-methylpentan-2-yl)-c-hydroxycarbonimidoyl]-2-methylbutyl}-c-hydroxycarbonimidoyl)methyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl}-c-hydroxycarbonimidoyl)methyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-1-methylpropyl}octanimidic acid

C51H93N11O12 (1051.7005)

epicholestrol

C27H46O (386.3548)

2,3-dimethoxy-6-(2-methylprop-1-en-1-yl)phenyl acetate

C14H18O4 (250.1205)

(4as,5r,8r,8as)-n-(7,8-dimethoxy-2-oxochromen-3-yl)-4a,5,8-trihydroxy-4,5,8,8a-tetrahydro-1,2-benzoxazine-3-carboxamide

C20H20N2O9 (432.1169)

(2r,7r)-7-hydroxy-2-[(1e)-oct-1-en-1-yl]-3,5,6,7-tetrahydro-2h-1-benzofuran-4-one

C16H24O3 (264.1725)

8-hydroxy-2-(1-hydroxyheptyl)-4-methoxy-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one

C17H28O5 (312.1937)

3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one

C20H22N2O9S2 (498.0767)

methyl 1-{[(5-{[5-({[2-(methoxycarbonyl)pyrrolidin-1-yl]imino}methyl)-4-{[5-({[2-(methoxycarbonyl)pyrrolidin-1-yl]imino}methyl)furan-2-yl]methyl}furan-2-yl]methyl}furan-2-yl)methylidene]amino}pyrrolidine-2-carboxylate

C35H42N6O9 (690.3013)

(2s,4r,5s,6s,9r)-4-hexyl-5,9-dihydroxy-3,7-dioxatricyclo[6.4.0.0²,⁶]dodec-1(8)-en-12-one

C16H24O5 (296.1624)

(4s,6r,8r,10s,16s)-4,6,8,10,16-pentamethyldocosane

C27H56 (380.4382)

2-hydroxy-2-{[4-(1-hydroxyocta-2,4-dien-1-ylidene)-1-methyl-3,5-dioxopyrrolidin-2-yl]methyl}-3-methylbutanoic acid

C19H27NO6 (365.1838)

10-hexyl-11,12-dioxatricyclo[7.2.1.0¹,⁶]dodecane-2,5-diol

C16H28O4 (284.1987)

(e)-n-{[4-methoxy-3-(methylsulfanyl)-6-phenylpyridin-2-yl]methylidene}hydroxylamine

C14H14N2O2S (274.0776)

4,5-dihydroxy-3-(1-hydroxyhex-4-en-1-yl)-2,5-dimethylcyclopent-2-en-1-one

C13H20O4 (240.1362)

7,9,10a-trihydroxy-3-methyl-1h-benzo[g]isochromen-10-one

C14H12O5 (260.0685)

2-ethyl-3-methyl-5h,6h,7h,8h-imidazo[1,2-a]pyridine

C10H16N2 (164.1313)

tetracosa-9,10-diene

C24H46 (334.3599)

(1r,8s,9s,11s,14r)-4,8,14,15,15-pentamethyltetracyclo[9.3.1.0¹,⁹.0⁵,⁸]pentadec-4-en-6-one

C20H30O (286.2297)

6,10-dihydroxy-15-methyl-8,16-dioxatricyclo[7.7.1.0²,⁷]heptadec-2(7)-en-3-one

C16H24O5 (296.1624)

(1s,4r,7r,8s,9r)-n-(7,8-dimethoxy-2-oxochromen-3-yl)-7,9-dihydroxy-12-oxa-2,3-dithia-11-azatricyclo[6.2.2.0⁴,⁹]dodec-5-ene-1-carboximidic acid

C20H20N2O8S2 (480.0661)

4-hydroxy-3-methyl-6-[(1e,3e)-penta-1,3-dien-1-yl]pyran-2-one

C11H12O3 (192.0786)

3-hydroxy-7a-methyl-10'-methylidene-hexahydro-3'-oxaspiro[2-benzofuran-4,5'-tricyclo[7.2.1.0¹,⁶]dodecane]-2',11'-dione

C20H26O5 (346.178)

(1r,2s,4s,5r,7s,8s,9s,10s,11r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-4,7,9,10-tetrol

C20H30O5 (350.2093)

(3r)-3-methylpentacosane

C26H54 (366.4225)

5-(1-hydroxyethyl)-1-isocyano-3,7-dioxatricyclo[4.1.0.0²,⁴]heptan-5-ol

C8H9NO4 (183.0532)

(5s)-3-(dimethylamino)-5-ethenyl-5-hydroxycyclopent-2-en-1-one

C9H13NO2 (167.0946)

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

C29H50O (414.3861)

(9e,12e)-11-oxooctadeca-9,12-dienoic acid

C18H30O3 (294.2195)

(1s,2s,3r,5s,8s,9s,10s,11r,15s)-15-(acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-3-yl acetate

C24H32O8 (448.2097)

(2s)-n-[(1s,2s)-1-({1-[(2s)-2-{[(1s)-2-hydroxy-1-{[(1s,2s)-1-({1-[(2s)-2-{[(1s)-1-{[(1s)-1-({1-[(2s)-2-{[(2s)-1-hydroxy-4-methylpentan-2-yl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl}-c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl}-c-hydroxycarbonimidoyl)-2-methylbutyl]-c-hydroxycarbonimidoyl}ethyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl}-c-hydroxycarbonimidoyl)-2-methylbutyl]-2-({1-hydroxy-2-[(1-hydroxyethylidene)amino]-2-methylpropylidene}amino)butanediimidic acid

C70H121N15O17 (1443.9064)

(2e,4e)-1-(2,4-dihydroxy-3-methylphenyl)hexa-2,4-dien-1-one

C13H14O3 (218.0943)

n-{1-[({[(1s)-1-{[1-({[({[(1s)-1-({1-[({[(1s,2s)-1-{[(2s)-1-hydroxy-4-methylpentan-2-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]methyl}-c-hydroxycarbonimidoyl)-1-methylethyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-1-methylethyl}octanimidic acid

C50H91N11O12 (1037.6848)

(1r,2s,8r,27r,39r)-1,2,14,15,16,19,20,21,29,35,36-undecahydroxy-2-(2-oxopropyl)-7,10,25,28,31,40-hexaoxaoctacyclo[35.2.1.0⁵,³⁹.0⁸,²⁷.0⁹,³⁰.0¹²,¹⁷.0¹⁸,²³.0³³,³⁸]tetraconta-4,12,14,16,18(23),19,21,33,35,37-decaene-3,6,11,24,32-pentone

C37H28O23 (840.1021)

6-(3-hydroxy-2,3-dimethylcyclopentyl)-2-methylheptane-2,3,6-triol

C15H30O4 (274.2144)

(2s,4r,8r)-8-hydroxy-2-[(1s)-1-hydroxyheptyl]-4-methoxy-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one

C17H28O5 (312.1937)

[(1r,6s)-6-{[(1s,4ar,6r,8ar)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (3s)-3-hydroxybutanoate

C26H36O7 (460.2461)

4-hexyl-5,9-dihydroxy-3,7-dioxatricyclo[6.4.0.0²,⁶]dodec-1(8)-en-12-one

C16H24O5 (296.1624)

(1r,2s,3s,5r,6r,8r,9s,10s,11s,12r)-11-(acetyloxy)-10-hydroxy-13,13-dimethyl-7-methylidene-4,18-dioxahexacyclo[8.6.2.1⁶,⁹.0¹,¹².0²,⁹.0³,⁵]nonadecan-8-yl acetate

C24H32O7 (432.2148)

2-amino-4-methylhex-5-ynoic acid

C7H11NO2 (141.079)

2-hydroxy-n-[(4z,8z)-3-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}octadeca-4,8-dien-2-yl]hexadecanimidic acid

C40H75NO9 (713.5442)

(2s,3r,4s,5r)-2-{4-[(6s,6ar,8r,10s,10ar)-1-hydroxy-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-4-yl]phenoxy}-5-(hydroxymethyl)oxolane-3,4-diol

C26H33NO7 (471.2257)

{8-formyl-11-hydroxy-7,7-dimethyl-14-methylidene-2,15-dioxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl}methyl acetate

C22H28O7 (404.1835)

{6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate

C26H36O8 (476.241)

trichoviridin

C8H9NO4 (183.0532)

(1s,3s,4r,6s,8r,9r,10s,11r,13s)-6-(acetyloxy)-3,11-dihydroxy-5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-8-yl acetate

C24H34O7 (434.2304)

(1r,2r,4r,8s,9r,10s,11s,13s,16r)-2,8,11,16-tetrahydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one

C20H30O5 (350.2093)

(2s,4s,6s)-6-hydroxy-2-({hydroxy[(2s)-1-[(2r)-2-methyldecanoyl]pyrrolidin-2-yl]methylidene}amino)-n-{1-[(1-{[(1s)-1-{[(1s)-1-({1-[(1-{[(2s)-1-[(2-hydroxyethyl)(methyl)amino]propan-2-yl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-4-methyl-8-oxodecanimidic acid

C59H108N10O12 (1148.8148)

(1r,2r,5s,6r,9r,10r)-10-hexyl-11,12-dioxatricyclo[7.2.1.0¹,⁶]dodecane-2,5-diol

C16H28O4 (284.1987)

(2r)-2-hydroxy-n-[(2s,3s,4r)-1,3,4-trihydroxyoctadecan-2-yl]tetracosanimidic acid

C42H85NO5 (683.6427)

(5r)-5-[(3z)-dodeca-3,11-dien-1-yl]oxolan-2-one

C16H26O2 (250.1933)

(1s,6r)-1-{[(1s,4ar,6r,8ar)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-ene-2,5-dione

C22H30O5 (374.2093)

[(1s,2r,6s)-6-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-2-hydroxy-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (2r,3s)-2,3-dihydroxybutanoate

C26H36O8 (476.241)

6-hydroxy-2-({hydroxy[1-(2-methyldecanoyl)pyrrolidin-2-yl]methylidene}amino)-n-{1-[(1-{[1-({1-[(1-{[1-({1-[(2-hydroxyethyl)(methyl)amino]propan-2-yl}-c-hydroxycarbonimidoyl)-1-methylethyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl}-c-hydroxycarbonimidoyl)-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-4-methyl-8-oxodecanimidic acid

C60H110N10O12 (1162.8304)

6-(2,4-dihydroxy-5-methylphenyl)-6-oxohex-2-enoic acid

C13H14O5 (250.0841)

(1s,2s,5r,7r,8s,10s,11r,13r)-10-hydroxy-12,12-dimethyl-6-methylidene-9,16-dioxo-14-oxapentacyclo[11.2.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-yl acetate

C22H28O6 (388.1886)

(1r,3s,4r,7r,8s,12s)-3,4,7,16-tetrahydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one

C20H22N2O9S2 (498.0767)

methyl 1-{[(5-{[5-({[2-(methoxycarbonyl)pyrrolidin-1-yl]imino}methyl)furan-2-yl]methyl}furan-2-yl)methylidene]amino}pyrrolidine-2-carboxylate

C23H28N4O6 (456.2009)

(1s,5r,6s)-1-(10,11-dihydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl)-5-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-en-2-one

C22H34O5 (378.2406)

methyl 1-({[5-(hydroxymethyl)furan-2-yl]methylidene}amino)pyrrolidine-2-carboxylate

C12H16N2O4 (252.111)

(1r,2r,4s,5s,9r,10s,12r,13s,16r)-2,12,16-trihydroxy-5-(hydroxymethyl)-5,9-dimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-11,15-dione

C20H28O6 (364.1886)

(1r,2r,5r,6s)-1-(11-hydroxy-3,7,11-trimethyldodeca-2,6-dien-1-yl)-4-methyl-7-oxabicyclo[4.1.0]hept-3-ene-2,5-diol

C22H36O4 (364.2613)

(1s,3s,4s,9r,10s,11s,13s)-3,11-dihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-6,15-dione

C20H28O4 (332.1987)

(1s,3r,4r,7r,8s,12s)-3,7,16-trihydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-4-iodo-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one

C20H21IN2O8S2 (607.9784)

(1r,3s,4s,7r,8s)-7-[(2e,4e)-hexa-2,4-dienoyl]-3-hydroxy-8-[(2r)-3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl]-5-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione

C28H32O8 (496.2097)

8,17-dihydroxy-14-(3-hydroxy-4,5-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.0¹,¹¹.0³,⁵.0³,⁹]octadeca-6,17-dien-12-one

C20H20N2O8S2 (480.0661)

{2-hydroxy-6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 2,3-dihydroxybutanoate

C26H38O8 (478.2567)

methyl (2s)-1-{[(5-{[5-({[(2s)-2-(methoxycarbonyl)pyrrolidin-1-yl]imino}methyl)-4-{[5-({[(2s)-2-(methoxycarbonyl)pyrrolidin-1-yl]imino}methyl)furan-2-yl]methyl}furan-2-yl]methyl}furan-2-yl)methylidene]amino}pyrrolidine-2-carboxylate

C35H42N6O9 (690.3013)

(1r,2s,3r)-3-[(2s)-2-hydroxy-6-methylhept-5-en-2-yl]-1,2-dimethylcyclopentan-1-ol

C15H28O2 (240.2089)

(1s,2r,7r,9r,11r)-1,2,5-trimethyl-12-methylidene-8-oxatricyclo[7.2.1.0²,⁷]dodec-5-en-11-yl acetate

C17H24O3 (276.1725)

(1s,3s,4s,6s,9r,10s,11s,13s)-3,11-dihydroxy-5,5,9-trimethyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-6-yl acetate

C22H32O5 (376.225)

(1s,3r,4r,6z,8s,10r,11r,13z)-3,10-dihydroxy-6,13-bis[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,4,8-trimethyl-2,9-dioxapentacyclo[8.4.0.0³,⁸.0⁴,¹⁴.0⁷,¹¹]tetradecane-5,12-dione

C27H30O8 (482.1941)

1-isopropyl-4,8-dimethylspiro[4.5]dec-8-ene-2,7-diol

C15H26O2 (238.1933)

methyl (2r,4ar,5s,5'z,8's,8ar)-5,8'-dihydroxy-5'-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1',8'-dimethyl-3,6',7'-trioxo-4a,5,6,8a-tetrahydrospiro[1,4-benzodioxine-2,2'-bicyclo[2.2.2]octane]-7-carboxylate

C25H28O10 (488.1682)

(2s,4r)-2-amino-4-hydroxyhept-6-ynoic acid

C7H11NO3 (157.0739)

(1s,3s,4r,6s,8s,9r,10r,11s,13s,15r)-6-(acetyloxy)-3,8,15-trihydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-11-yl acetate

C24H36O7 (436.2461)

(2s)-2-({1-hydroxy-2-[(1-hydroxyethylidene)amino]-2-methylpropylidene}amino)-n-[(1s,2s)-1-{[(1s,2s)-1-({1-[(2r)-2-{[(1s)-1-{[(1s)-1-({1-[(2s)-2-{[(2s)-1-hydroxy-4-methylpentan-2-yl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl}-c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}-3-methylbutyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl}-c-hydroxycarbonimidoyl)-2-methylbutyl]-c-hydroxycarbonimidoyl}-2-methylbutyl]pentanediimidic acid

C59H104N12O13 (1188.7845)

(1s,3r,4r,6e,8s,10r,11r,13e)-3,10-dihydroxy-6,13-bis[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,4,8,11-tetramethyl-2,9-dioxapentacyclo[8.4.0.0³,⁸.0⁴,¹⁴.0⁷,¹¹]tetradecane-5,12-dione

C28H32O8 (496.2097)

1-(2,4-dihydroxy-5-methylphenyl)hexa-2,4-dien-1-one

C13H14O3 (218.0943)

(1r,2s,6s,7s,8s,9s,12e)-2-[(2e,4e)-hexa-2,4-dienoyl]-5,6,9-trihydroxy-12-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,4,6,9-tetramethyltricyclo[6.2.2.0²,⁷]dodec-4-ene-3,10,11-trione

C28H32O8 (496.2097)

methyl (2r,4ar,5s,5'z,8's,8ar)-5,8'-dihydroxy-5'-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1',8'-dimethyl-3,6',7'-trioxo-4a,5,8,8a-tetrahydrospiro[1,4-benzodioxine-2,2'-bicyclo[2.2.2]octane]-7-carboxylate

C25H28O10 (488.1682)

(1r,2s,4s,5r,7r,8s,9s,10s,11r)-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecane-4,7,9,10-tetrol

C20H30O5 (350.2093)

6,9-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

C20H26O6 (362.1729)

4-(4-hydroxyphenyl)-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-1-ol

C21H25NO3 (339.1834)

4-(3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl)-2-methylbut-2-enoic acid

C15H22O3 (250.1569)

8-hydroxy-2-(1-hydroxyheptyl)-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one

C16H26O4 (282.1831)

2-hydroxy-n-(1,3,4-trihydroxyoctadecan-2-yl)tetracosanimidic acid

C42H85NO5 (683.6427)

9,14-dihydroxy-7,7-dimethyl-17-methylidene-2,18-dioxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-19-yl acetate

C22H28O8 (420.1784)

{2-hydroxy-6-[(6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl)methyl]-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl}methyl 3-hydroxybutanoate

C26H38O7 (462.2617)

2-hydroxy-2-{[(2r)-4-(1-hydroxyocta-2,4-dien-1-ylidene)-1-methyl-3,5-dioxopyrrolidin-2-yl]methyl}-3-methylbutanoic acid

C19H27NO6 (365.1838)

10-hexyl-11,12-dioxatricyclo[7.2.1.0¹,⁶]dodecane-2,4-diol

C16H28O4 (284.1987)

(1r,2s,3r,5s,6r,8r,9s,10s,11s,12r)-8,10-dihydroxy-13,13-dimethyl-7-methylidene-4,18-dioxahexacyclo[8.6.2.1⁶,⁹.0¹,¹².0²,⁹.0³,⁵]nonadecan-11-yl acetate

C22H30O6 (390.2042)

(2e)-6-(2,4-dihydroxy-5-methylphenyl)-6-oxohex-2-enoic acid

C13H14O5 (250.0841)

(1r,2r,3z,5r,7s,9r,10r,12e)-9,10-dihydroxy-3,12-bis[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,5,7-trimethyl-8-oxatetracyclo[7.4.0.0²,⁷.0⁵,¹⁰]tridecane-4,6,11,13-tetrone

C27H28O9 (496.1733)

(1r,2r,4s,5s,8s,9r,10s,13s,16r)-2,8,16-trihydroxy-9-(hydroxymethyl)-5-methyl-14-methylidene-15-oxotetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane-5-carbaldehyde

C20H28O6 (364.1886)

(1r,2r,4r,8s,9r,10s,13s,14s,16s)-2,8,16-trihydroxy-9,14-bis(hydroxymethyl)-5,5-dimethyltetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one

C20H32O6 (368.2199)

[(1r,2s,4s,5r,8r,9s,10s,11r,12r,18r)-4,9,10,18-tetrahydroxy-12-methyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-12-yl]methyl acetate

C22H30O8 (422.1941)

methyl (2s)-1-({[5-(hydroxymethyl)furan-2-yl]methylidene}amino)pyrrolidine-2-carboxylate

C12H16N2O4 (252.111)

n-{[4-methoxy-3-(methylsulfanyl)-6-phenylpyridin-2-yl]methylidene}hydroxylamine

C14H14N2O2S (274.0776)

7-(hexa-2,4-dienoyl)-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-(1-hydroxyhexa-2,4-dien-1-ylidene)-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione

C28H32O8 (496.2097)

[(1r,4r,8r,9r,10r,11s,13r)-11-hydroxy-8-(hydroxymethyl)-7,7-dimethyl-14-methylidene-2,15-dioxo-3-oxatetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-9-yl]methyl acetate

C22H30O7 (406.1991)

(1r,3s,5s,8r,9s,13s)-8,17-dihydroxy-14-(2-hydroxy-3,4-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.0¹,¹¹.0³,⁵.0³,⁹]octadeca-6,17-dien-12-one

C20H20N2O8S2 (480.0661)

(1s,2s,5r,10s,11r,15s,18r)-9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-15-yl acetate

C22H30O7 (406.1991)

2,10-dihydroxy-11-(1-hydroxyhexa-2,4-dien-1-ylidene)-5-(hydroxymethyl)-5-methoxy-8,10-dimethyl-4-oxatricyclo[6.2.2.0²,⁷]dodecane-9,12-dione

C21H28O8 (408.1784)

(4e)-5-(1,3-oxazol-4-yl)pent-4-ene-2,3-diol

C8H11NO3 (169.0739)

1,2,8-trihydroxy-6-methyl-1,2,3,4,4a,9a-hexahydroanthracene-9,10-dione

C15H16O5 (276.0998)

8,17-dihydroxy-14-(2-hydroxy-3,4-dimethoxyphenyl)-4,10-dioxa-15,16-dithia-11,18-diazapentacyclo[11.3.2.0¹,¹¹.0³,⁵.0³,⁹]octadeca-6,17-dien-12-one

C20H20N2O8S2 (480.0661)

(2r,4s,5r,6r,9r)-4-hexyl-5,9-dihydroxy-3,7-dioxatricyclo[6.4.0.0²,⁶]dodec-1(8)-en-12-one

C16H24O5 (296.1624)

n-[(1r)-1-[({[(1s)-1-{[1-({[({[(1s)-1-({1-[({[(1s,2s)-1-{[(2s)-1-hydroxy-4-methylpentan-2-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]methyl}-c-hydroxycarbonimidoyl)-1-methylethyl]-c-hydroxycarbonimidoyl}-2-methylpropyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-1-methylpropyl]octanimidic acid

C51H93N11O12 (1051.7005)

(1r,2s,5s,7r,8r,10s,11z)-2,10-dihydroxy-11-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-5-(hydroxymethyl)-5-methoxy-8,10-dimethyl-4-oxatricyclo[6.2.2.0²,⁷]dodecane-9,12-dione

C21H28O8 (408.1784)

(1s,5r,6s)-1-{[(1s,4ar,6r,8ar)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-(hydroxymethyl)-7-oxabicyclo[4.1.0]hept-3-en-2-one

C22H32O5 (376.225)

(2e,4e)-1-(2,4-dihydroxy-5-methylphenyl)hexa-2,4-dien-1-one

C13H14O3 (218.0943)

(9z)-9-pentacosene

C25H50 (350.3912)

(1r,2s,3r,5s,8r,9r,10s,11s,12r)-8,10-dihydroxy-13,13-dimethyl-7-methylidene-4,18-dioxahexacyclo[8.6.2.1⁶,⁹.0¹,¹².0²,⁹.0³,⁵]nonadecan-11-yl acetate

C22H30O6 (390.2042)

(1r,2r,5s,7r,9s,10r,15r,16s)-15-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-5,10-dihydroxy-2-methyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-11-ene-16-carboxylic acid

C28H42O5 (458.3032)

(z)-n-{[4-methoxy-3-(methylsulfanyl)-6-phenylpyridin-2-yl]methylidene}hydroxylamine

C14H14N2O2S (274.0776)

methyl (2s)-1-{[(5-{[5-({[(2s)-2-(methoxycarbonyl)pyrrolidin-1-yl]imino}methyl)furan-2-yl]methyl}furan-2-yl)methylidene]amino}pyrrolidine-2-carboxylate

C23H28N4O6 (456.2009)

(1s,4r,6s,8s,9s,12s,13s,16r,17s)-6,9-dihydroxy-7,7,17-trimethyl-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

C20H28O6 (364.1886)

4-(hexa-2,4-dienoyl)-3,6-dihydroxy-2,6-dimethylcyclohexa-2,4-dien-1-one

C14H16O4 (248.1049)

(1s,2s,5r,7r,8s,9s,10s,11r,15r)-10-(acetyloxy)-9,15-dihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-yl acetate

C24H34O7 (434.2304)

7-hydroxy-2-(oct-1-en-1-yl)-3,5,6,7-tetrahydro-2h-1-benzofuran-4-one

C16H24O3 (264.1725)

3-ethyl-2-methyl-5h,6h,7h,8h-imidazo[1,2-a]pyridine

C10H16N2 (164.1313)

6-hydroxy-2-({hydroxy[1-(2-methyldecanoyl)pyrrolidin-2-yl]methylidene}amino)-n-{1-[(1-{[1-({1-[(1-{[1-({1-[(2-hydroxyethyl)(methyl)amino]propan-2-yl}-c-hydroxycarbonimidoyl)-1-methylethyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-4-methyl-8-oxodecanimidic acid

C59H108N10O12 (1148.8148)

(2s,5s,8r,13r,14s,15r)-13,14,19-trihydroxy-16,16-dimethyl-6-methylidene-10,12-dioxahexacyclo[9.8.0.0¹,¹⁵.0²,⁸.0⁵,⁹.0⁸,¹³]nonadecan-7-one

C20H26O6 (362.1729)

heptacosa-9,10-diene

C27H52 (376.4069)

(1s,4s,6s,8r,9s,12s,13s,16r)-6,9-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

C20H26O6 (362.1729)

5,10-dihydroxy-11-(1-hydroxyhexa-2,4-dien-1-ylidene)-8,10-dimethyl-3-oxatricyclo[6.2.2.0²,⁷]dodec-5-ene-4,9,12-trione

C19H20O7 (360.1209)

(5r)-5-[(1z)-oct-1-en-1-yl]oxolan-2-one

C12H20O2 (196.1463)

7'-hydroxy-3,3-dimethyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecane]-2-carbaldehyde

C20H26O5 (346.178)

(1r,2r,4s,6r,9r,10s)-10-hexyl-11,12-dioxatricyclo[7.2.1.0¹,⁶]dodecane-2,4-diol

C16H28O4 (284.1987)

(1s,2s,8s,9r,11r)-3,9,10,15-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

C20H28O6 (364.1886)

(2r,6e)-2,5-dihydroxy-6-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,4-dimethylcyclohex-4-ene-1,3-dione

C14H16O5 (264.0998)

(1s,2r,4s,5s)-1-isopropyl-4,8-dimethylspiro[4.5]dec-8-ene-2,7-diol

C15H26O2 (238.1933)

(2s,3r,5s,8s,9s,10s,11r,15s)-15-(acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-3-yl acetate

C24H32O8 (448.2097)

4-(hexa-2,4-dien-1-yl)-3-(hydroxymethyl)-5h-furan-2-one

C11H14O3 (194.0943)

2-phenyl-5-(sec-butyl)-1h-pyrrole

C14H17N (199.1361)

(2s,5s)-5-hydroxy-2-[(1e)-oct-1-en-1-yl]-3,5,6,7-tetrahydro-2h-1-benzofuran-4-one

C16H24O3 (264.1725)

5-(dodeca-3,11-dien-1-yl)oxolan-2-one

C16H26O2 (250.1933)

n-[1-({1-[2-({2-hydroxy-1-[(1-{[1-(2-{[1-({1-[(1-{2-[(1-hydroxy-4-methylpentan-2-yl)-c-hydroxycarbonimidoyl]pyrrolidin-1-yl}-2-methyl-1-oxopropan-2-yl)-c-hydroxycarbonimidoyl]-3-methylbutyl}-c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl)-2-methyl-1-oxopropan-2-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl)-c-hydroxycarbonimidoyl]ethyl}-c-hydroxycarbonimidoyl)pyrrolidin-1-yl]-2-methyl-1-oxopropan-2-yl}-c-hydroxycarbonimidoyl)-2-methylbutyl]-2-({1-hydroxy-2-[(1-hydroxyethylidene)amino]-2-methylpropylidene}amino)butanediimidic acid

C70H121N15O17 (1443.9064)

[(4s)-4-{[(1s,4ar,6r,8ar)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4-hydroxy-3,6-dioxocyclohex-1-en-1-yl]methyl (3s)-3-hydroxybutanoate

C26H38O7 (462.2617)

1-(2,4-dihydroxy-3-methylphenyl)hexa-2,4-dien-1-one

C13H14O3 (218.0943)

(6r)-6-[(1r,2s,3r)-3-hydroxy-2,3-dimethylcyclopentyl]-2-methylheptane-2,3,6-triol

C15H30O4 (274.2144)

(7s)-7-hydroxy-7-[(2s,6s)-6-hydroxy-5-oxo-2,3,4,6,7,8-hexahydro-1-benzopyran-2-yl]heptanoic acid

C16H24O6 (312.1573)

(2e)-4-[(2s,3s,3as,7ar)-3,6-dimethyl-2,3,3a,4,5,7a-hexahydro-1-benzofuran-2-yl]-2-methylbut-2-enoic acid

C15H22O3 (250.1569)

(1r,3r,4r,7r,8s,12s)-4-chloro-3,7,17-trihydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15,16-trithia-10,18-diazatetracyclo[10.4.2.0¹,¹⁰.0³,⁸]octadeca-5,17-dien-11-one

C20H21ClN2O8S3 (548.0149)

(1r,2r,4e,6s,7r,9s)-13-[(4e)-hex-4-enoyl]-6,7,10,12-tetrahydroxy-4-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-10,12-diene-3,5-dione

C28H34O9 (514.2203)

(2s,4r,6e)-2-({hydroxy[(2s)-1-[(2r)-2-methyldecanoyl]pyrrolidin-2-yl]methylidene}amino)-n-{1-[(1-{[(1s,2s)-1-{[(1s)-1-({1-[(1-{[(2s)-1-[(2-hydroxyethyl)(methyl)amino]propan-2-yl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-4-methyl-8-oxodec-6-enimidic acid

C60H108N10O11 (1144.8199)

n-{1-[({[1-({1-[({[({1-[(1-{[({1-[(1-hydroxy-4-methylpentan-2-yl)-c-hydroxycarbonimidoyl]-2-methylbutyl}-c-hydroxycarbonimidoyl)methyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl}-c-hydroxycarbonimidoyl)methyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}methyl)-c-hydroxycarbonimidoyl]-1-methylethyl}octanimidic acid

C50H91N11O12 (1037.6848)

stigmast-5-en-3-ol, (3β)-

C29H50O (414.3861)

[(1r,6s)-6-{[(1s,4ar,8ar)-5,5,8a-trimethyl-2-methylidene-6-oxo-hexahydronaphthalen-1-yl]methyl}-2,5-dioxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]methyl (2r,3s)-2,3-dihydroxybutanoate

C26H34O8 (474.2254)

2-({1-hydroxy-2-[(1-hydroxyethylidene)amino]-2-methylpropylidene}amino)-n-{1-[(1-{[1-(2-{[1-({1-[(1-{2-[(1-hydroxy-4-methylpentan-2-yl)-c-hydroxycarbonimidoyl]pyrrolidin-1-yl}-2-methyl-1-oxopropan-2-yl)-c-hydroxycarbonimidoyl]-3-methylbutyl}-c-hydroxycarbonimidoyl)-3-methylbutyl]-c-hydroxycarbonimidoyl}pyrrolidin-1-yl)-2-methyl-1-oxopropan-2-yl]-c-hydroxycarbonimidoyl}-2-methylbutyl)-c-hydroxycarbonimidoyl]-2-methylbutyl}pentanediimidic acid

C59H104N12O13 (1188.7845)

3-isopropyl-5h,6h,7h,8h-imidazo[1,2-a]pyridine

C10H16N2 (164.1313)

(4r,5s)-3-ethyl-4,5-dihydroxycyclopent-2-en-1-one

C7H10O3 (142.063)

(2s,6s,7r,9s,13z)-4-[(2e,4e)-hexa-2,4-dienoyl]-6,7,12-trihydroxy-13-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-3,11-diene-5,10-dione

C28H32O8 (496.2097)

methyl (2s)-1-({[5-({[(2s)-2-(methoxycarbonyl)pyrrolidin-1-yl]imino}methyl)furan-2-yl]methylidene}amino)pyrrolidine-2-carboxylate

C18H24N4O5 (376.1747)

2-isopropyl-5-(2-methylpropyl)-1h-pyrrole

C11H19N (165.1517)

8-(hydroxymethyl)-1-isopropyl-4-methylspiro[4.5]dec-8-en-7-ol

C15H26O2 (238.1933)

(6s)-4-[(2e,4e)-hexa-2,4-dienoyl]-3,6-dihydroxy-2,6-dimethylcyclohexa-2,4-dien-1-one

C14H16O4 (248.1049)

(1r,2r,5s,7r,8r,10s,11z)-2,10-dihydroxy-11-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-5-(hydroxymethyl)-5-methoxy-8,10-dimethyl-4-oxatricyclo[6.2.2.0²,⁷]dodecane-9,12-dione

C21H28O8 (408.1784)

(1r,2s,3s,5s,7r,8s,9s,10s,11r,15s)-7,9,10,15-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-3-yl acetate

C22H32O7 (408.2148)

(1s,4s,5s,7r)-8-(hydroxymethyl)-1-isopropyl-4-methylspiro[4.5]dec-8-en-7-ol

C15H26O2 (238.1933)

(1s,4s,8r,9r,12s,13s,14s,16s)-14-hydroxy-9-methoxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

C21H28O6 (376.1886)

7,9,18-trihydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-10-yl acetate

C22H32O6 (392.2199)

(4e)-1-(2,4-dihydroxy-5-methylphenyl)hex-4-en-1-one

C13H16O3 (220.1099)

(1s,4s,5s,7r,8r)-8-(hydroxymethyl)-1-isopropyl-4-methylspiro[4.5]dec-9-ene-7,8-diol

C15H26O3 (254.1882)

8-[(1r,2s)-2-octylcyclopropyl]octanoic acid

C19H36O2 (296.2715)

(1s,2r,5s,8s,9s,11s)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-3-yl acetate

C22H30O6 (390.2042)

2,5,10-trihydroxy-11-(1-hydroxyhexa-2,4-dien-1-ylidene)-5-(hydroxymethyl)-8,10-dimethyl-4-oxatricyclo[6.2.2.0²,⁷]dodecane-9,12-dione

C20H26O8 (394.1628)

3,7,16-trihydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-4-iodo-9-oxa-14,15-dithia-10,17-diazatetracyclo[10.3.2.0¹,¹⁰.0³,⁸]heptadeca-5,16-dien-11-one

C20H21IN2O8S2 (607.9784)

9,10,18-trihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-15-yl acetate

C22H30O7 (406.1991)

5-hydroxy-2-(oct-1-en-1-yl)-3,5,6,7-tetrahydro-2h-1-benzofuran-4-one

C16H24O3 (264.1725)

(1s,1's,2r,6's,7's,9's)-7'-hydroxy-3,3-dimethyl-10'-methylidene-2',11'-dioxo-3'-oxaspiro[cyclohexane-1,5'-tricyclo[7.2.1.0¹,⁶]dodecane]-2-carbaldehyde

C20H26O5 (346.178)

(1s,2s,3r,5s,6s,8s,9s,10s,11r,15s)-3,9,10,15-tetrahydroxy-6-(methoxymethyl)-12,12-dimethyl-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

C21H32O7 (396.2148)

(2e)-3-hydroxy-2-(1,3-oxazol-4-ylmethylidene)butanal

C8H9NO3 (167.0582)

(1s,4s,8r,12s,13s,16s)-9,14-dihydroxy-7,7-dimethyl-17-methylidene-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

C20H26O6 (362.1729)

5-{[2-amino-4-methyl-3-(sulfooxy)pentyl]oxy}-15-(5,6-dimethylhept-3-en-2-yl)-10-hydroxy-2-methyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-11-ene-16-carboxylic acid

C34H55NO9S (653.3597)

1-isopropyl-4,8-dimethylspiro[4.5]dec-8-en-7-ol

C15H26O (222.1984)

(1s,4s,9r,13s,14s,16s,17s)-9,14-dihydroxy-17-(methoxymethyl)-7,7-dimethyl-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

C21H30O7 (394.1991)

(4s,5s)-4,5-dihydroxy-3-[(1r,4e)-1-hydroxyhex-4-en-1-yl]-2,5-dimethylcyclopent-2-en-1-one

C13H20O4 (240.1362)

(2s,4s)-2-amino-4-hydroxyhept-6-ynoic acid

C7H11NO3 (157.0739)

9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-3-yl acetate

C22H30O6 (390.2042)

(1s,3r,4r,8s,10r,11r)-13-[(4e)-hex-4-enoyl]-3,10,12-trihydroxy-6-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,4,8,11-tetramethyl-2,9-dioxapentacyclo[8.4.0.0³,⁸.0⁴,¹⁴.0⁷,¹¹]tetradec-12-en-5-one

C28H34O8 (498.2254)

(1r,2r,4r,9r,10s,11r,12r,13r,16r)-2,11,12,16-tetrahydroxy-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecan-15-one

C20H30O5 (350.2093)

(2s,7r)-7-hydroxy-2-[(1e)-oct-1-en-1-yl]-3,5,6,7-tetrahydro-2h-1-benzofuran-4-one

C16H24O3 (264.1725)

3-(2-hydroxy-6-methylhept-5-en-2-yl)-1,2-dimethylcyclopentan-1-ol

C15H28O2 (240.2089)

n-(7,8-dimethoxy-2-oxochromen-3-yl)-4a,5,8-trihydroxy-4,5,8,8a-tetrahydro-1,2-benzoxazine-3-carboxamide

C20H20N2O9 (432.1169)

(4as,6as,6br,8as,10s,12ar,12bs,14br)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,7,8,8a,10,11,12,12b,13,14b-tetradecahydropicene-4a-carboxylic acid

C30H48O3 (456.3603)

9,9,14,14-tetramethyl-19-methylidene-5,13,15-trioxahexacyclo[16.2.1.0¹,⁶.0²,¹⁶.0³,⁸.0³,¹²]henicosane-6,7,20-triol

C23H34O6 (406.2355)

(1r,3s,4s,5e,7r,8s)-7-[(2e,4e)-hexa-2,4-dienoyl]-3-hydroxy-8-[(2s)-3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl]-5-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione

C28H32O8 (496.2097)

{3,9,10,15-tetrahydroxy-12-methyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-12-yl}methyl acetate

C22H30O8 (422.1941)

(2s,4s,6s)-6-hydroxy-2-({hydroxy[(2s)-1-[(2r)-2-methyldecanoyl]pyrrolidin-2-yl]methylidene}amino)-n-{1-[(1-{[(1s,2s)-1-{[(1s)-1-({1-[(1-{[(2s)-1-[(2-hydroxyethyl)(methyl)amino]propan-2-yl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-c-hydroxycarbonimidoyl)-2-methylpropyl]-c-hydroxycarbonimidoyl}-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-4-methyl-8-oxodecanimidic acid

C60H110N10O12 (1162.8304)

7,8-dihydroxy-6-methoxy-1-pentyl-1,4-dihydro-2-benzopyran-3-one

C15H20O5 (280.1311)

10-hydroxy-12,12-dimethyl-6-methylidene-9,16-dioxo-14-oxapentacyclo[11.2.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-yl acetate

C22H28O6 (388.1886)

n-(7,8-dimethoxy-2-oxochromen-3-yl)-7,9-dihydroxy-12-oxa-2,3-dithia-11-azatricyclo[6.2.2.0⁴,⁹]dodec-5-ene-1-carboximidic acid

C20H20N2O8S2 (480.0661)

(10as)-7,9,10a-trihydroxy-3-methyl-1h-benzo[g]isochromen-10-one

C14H12O5 (260.0685)

(1r,2r,5s,7r,9s,10r,15r,16s)-5-{[(2r,3s)-2-amino-4-methyl-3-(sulfooxy)pentyl]oxy}-15-[(2r,3e,5r)-5,6-dimethylhept-3-en-2-yl]-10-hydroxy-2-methyl-8-oxapentacyclo[9.7.0.0²,⁷.0⁷,⁹.0¹²,¹⁶]octadec-11-ene-16-carboxylic acid

C34H55NO9S (653.3597)

(6s,6ar,8r,10s,10ar)-4-(4-hydroxyphenyl)-6,8,10-trimethyl-6h,6ah,7h,8h,9h,10h,10ah-isochromeno[4,3-c]pyridin-1-ol

C21H25NO3 (339.1834)

(1r,2s,5s,7r,8r,10s,11z)-2,5,10-trihydroxy-11-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-5-(hydroxymethyl)-8,10-dimethyl-4-oxatricyclo[6.2.2.0²,⁷]dodecane-9,12-dione

C20H26O8 (394.1628)

2-({hydroxy[1-(2-methyldecanoyl)pyrrolidin-2-yl]methylidene}amino)-n-{1-[(1-{[1-({1-[(1-{[1-({1-[(2-hydroxyethyl)(methyl)amino]propan-2-yl}-c-hydroxycarbonimidoyl)-1-methylethyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-2-methylpropyl}-c-hydroxycarbonimidoyl)-2-methylbutyl]-c-hydroxycarbonimidoyl}-1-methylethyl)-c-hydroxycarbonimidoyl]-1-methylethyl}-4-methyl-8-oxodec-6-enimidic acid

C60H108N10O11 (1144.8199)

(1s,4s,6s,8r,9r,12s,13s,14s,16s,17s)-9,14-dihydroxy-17-(methoxymethyl)-7,7-dimethyl-2,18-dioxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-6-yl acetate

C23H32O9 (452.2046)

(2s,8r)-8-hydroxy-2-[(1s)-1-hydroxyheptyl]-2,3,4,6,7,8-hexahydro-1-benzopyran-5-one

C16H26O4 (282.1831)

3-(dimethylamino)-5-ethenyl-5-hydroxycyclopent-2-en-1-one

C9H13NO2 (167.0946)

13-(hex-4-enoyl)-6,7,10,12-tetrahydroxy-4-(1-hydroxyhexa-2,4-dien-1-ylidene)-2,6,9,11-tetramethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-10,12-diene-3,5-dione

C28H34O9 (514.2203)

(1r,2s,3r,10s,11r,15s)-15-(acetyloxy)-9,10-dihydroxy-12,12-dimethyl-6-methylidene-7-oxo-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-3-yl acetate

C24H32O8 (448.2097)

1-[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-5-methylpyrimidin-2-one

C10H14N2O6 (258.0852)

4-chloro-3,7,17-trihydroxy-13-(2-hydroxy-3,4-dimethoxyphenyl)-9-oxa-14,15,16-trithia-10,18-diazatetracyclo[10.4.2.0¹,¹⁰.0³,⁸]octadeca-5,17-dien-11-one

C20H21ClN2O8S3 (548.0149)

(1r,10r,18r,19r)-13-{[(1s,4ar,6r,8ar)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-4,12,18,19-tetrahydroxy-6-methylpentacyclo[8.7.4.0¹,¹⁰.0³,⁸.0¹¹,¹⁶]henicosa-3,5,7,11(16),12,20-hexaene-2,9,14,15-tetrone

C37H40O9 (628.2672)

(1s,4s,8r,9r,12s,13s,14s,16s)-9-hydroxy-7,7-dimethyl-17-methylidene-2,18-dioxo-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecan-14-yl acetate

C22H28O7 (404.1835)

(1s,2s,3r,5s,8s,9s,10s,11r,15s)-3,9,10,15-tetrahydroxy-12,12-dimethyl-6-methylidene-17-oxapentacyclo[7.6.2.1⁵,⁸.0¹,¹¹.0²,⁸]octadecan-7-one

C20H28O6 (364.1886)

(1s,4s,8r,9r,12s,13s,14s,16s,17s)-9,14-dihydroxy-17-(methoxymethyl)-7,7-dimethyl-3,10-dioxapentacyclo[14.2.1.0¹,¹³.0⁴,¹².0⁸,¹²]nonadecane-2,18-dione

C21H30O7 (394.1991)

hexacosa-9,10-diene

C26H50 (362.3912)

5-(oct-1-en-1-yl)oxolan-2-one

C12H20O2 (196.1463)

(1r,3s,4s,5e,7r,8s)-7-[(2e,4e)-hexa-2,4-dienoyl]-3-hydroxy-8-(3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl)-5-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-1,3-dimethylbicyclo[2.2.2]octane-2,6-dione

C28H32O8 (496.2097)

(1s,5r,6s)-1-{[(1s,4ar,6r,8ar)-6-hydroxy-5,5,8a-trimethyl-2-methylidene-hexahydro-1h-naphthalen-1-yl]methyl}-5-hydroxy-4-methyl-7-oxabicyclo[4.1.0]hept-3-en-2-one

C22H32O4 (360.23)

8-(hydroxymethyl)-1-isopropyl-4-methylspiro[4.5]dec-9-ene-7,8-diol

C15H26O3 (254.1882)

pentacosa-9,10-diene

C25H48 (348.3756)

(1r,3s,4s,5z,7r,8s)-7-[(2e,4e)-hexa-2,4-dienoyl]-3-hydroxy-8-[(2s)-3-hydroxy-2,4-dimethyl-5-oxofuran-2-yl]-5-[(2e,4e)-1-hydroxyhexa-2,4-dien-1-ylidene]-3-methylbicyclo[2.2.2]octane-2,6-dione

C27H30O8 (482.1941)

3-ethyl-4,5-dihydroxycyclopent-2-en-1-one

C7H10O3 (142.063)

5,7-dihydroxy-3-methyl-2-(2-oxopropyl)naphthalene-1,4-dione

C14H12O5 (260.0685)

(4s,6r,8r,10s,16r,18s)-4,6,8,10,16,18-hexamethyldocosane

C28H58 (394.4538)