NCBI Taxonomy: 5117

Valsaceae (ncbi_taxid: 5117)

found 227 associated metabolites at family taxonomy rank level.

Ancestor: Diaporthales

Child Taxonomies: Phomopsis, Valsa, Leucostoma, Waydora, Valsella, Cytospora, Phruensis, Apioporthe, Winterella, Rostraureum, Anisogramma, Lollipopaia, Endothiella, Valseutypella, Chrysoporthella, environmental samples, unclassified Valsaceae

Protocatechuic acid

3,4-dihydroxybenzoic 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.

   

Lovastatin

[(1S,3R,7S,8S,8aR)-8-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-3,7-dimethyl-1,2,3,7,8,8a-hexahydronaphthalen-1-yl] (2S)-2-methylbutanoate

C24H36O5 (404.2563)


Lovastatin is a fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). It has a role as an Aspergillus metabolite, a prodrug, an anticholesteremic drug and an antineoplastic agent. It is a polyketide, a statin (naturally occurring), a member of hexahydronaphthalenes, a delta-lactone and a fatty acid ester. It is functionally related to a (S)-2-methylbutyric acid and a mevastatin. Lovastatin, also known as the brand name product Mevacor, is a lipid-lowering drug and fungal metabolite derived synthetically from a fermentation product of Aspergillus terreus. Originally named Mevinolin, lovastatin belongs to the statin class of medications, which are used to lower the risk of cardiovascular disease and manage abnormal lipid levels by inhibiting the endogenous production of cholesterol in the liver. More specifically, statin medications competitively inhibit the enzyme hydroxymethylglutaryl-coenzyme A (HMG-CoA) Reductase, which catalyzes the conversion of HMG-CoA to mevalonic acid and is the third step in a sequence of metabolic reactions involved in the production of several compounds involved in lipid metabolism and transport including cholesterol, low-density lipoprotein (LDL) (sometimes referred to as "bad cholesterol"), and very low-density lipoprotein (VLDL). Prescribing of statin medications is considered standard practice following any cardiovascular events and for people with a moderate to high risk of development of CVD, such as those with Type 2 Diabetes. The clear evidence of the benefit of statin use coupled with very minimal side effects or long term effects has resulted in this class becoming one of the most widely prescribed medications in North America. Lovastatin and other drugs from the statin class of medications including [atorvastatin], [pravastatin], [rosuvastatin], [fluvastatin], and [simvastatin] are considered first-line options for the treatment of dyslipidemia. Increasing use of the statin class of drugs is largely due to the fact that cardiovascular disease (CVD), which includes heart attack, atherosclerosis, angina, peripheral artery disease, and stroke, has become a leading cause of death in high-income countries and a major cause of morbidity around the world. Elevated cholesterol levels, and in particular, elevated low-density lipoprotein (LDL) levels, are an important risk factor for the development of CVD. Use of statins to target and reduce LDL levels has been shown in a number of landmark studies to significantly reduce the risk of development of CVD and all-cause mortality. Statins are considered a cost-effective treatment option for CVD due to their evidence of reducing all-cause mortality including fatal and non-fatal CVD as well as the need for surgical revascularization or angioplasty following a heart attack. Evidence has shown that even for low-risk individuals (with <10\\\\% risk of a major vascular event occurring within 5 years) statins cause a 20\\\\%-22\\\\% relative reduction in major cardiovascular events (heart attack, stroke, coronary revascularization, and coronary death) for every 1 mmol/L reduction in LDL without any significant side effects or risks. While all statin medications are considered equally effective from a clinical standpoint, [rosuvastatin] is considered the most potent; doses of 10 to 40mg [rosuvastatin] per day were found in clinical studies to result in a 45.8\\\\% to 54.6\\\\% decrease in LDL cholesterol levels, while lovastatin has been found to have an average decrease in LDL-C of 25-40\\\\%. Potency is thought to correlate to tissue permeability as the more lipophilic statins such as lovastatin are thought to enter endothelial cells by passive diffusion, as opposed to hydrophilic statins such as [pravastatin] and [rosuvastatin] which are taken up into hepatocytes through OATP1B1 (org... Lovastatin is a cholesterol-lowering agent that belongs to the class of medications called statins. It was the second agent of this class discovered. It was discovered by Alfred Alberts and his team at Merck in 1978 after screening only 18 compounds over 2 weeks. The agent, also known as mevinolin, was isolated from the fungi Aspergillus terreus. Research on this compound was suddenly shut down in 1980 and the drug was not approved until 1987. Interesting, Akira Endo at Sankyo Co. (Japan) patented lovastatin isolated from Monascus ruber four months before Merck. Lovastatin was found to be 2 times more potent than its predecessor, mevastatin, the first discovered statin. Like mevastatin, lovastatin is structurally similar to hydroxymethylglutarate (HMG), a substituent of HMG-Coenzyme A (HMG-CoA), a substrate of the cholesterol biosynthesis pathway via the mevalonic acid pathway. Lovastatin is a competitive inhibitor of HMG-CoA reductase with a binding affinity 20,000 times greater than HMG-CoA. Lovastatin differs structurally from mevastatin by a single methyl group at the 6 position. Lovastatin is a prodrug that is activated by in vivo hydrolysis of the lactone ring. It, along with mevastatin, has served as one of the lead compounds for the development of the synthetic compounds used today. A fatty acid ester that is mevastatin carrying an additional methyl group on the carbobicyclic skeleton. It is used in as an anticholesteremic drug and has been found in fungal species such as Aspergillus terreus and Pleurotus ostreatus (oyster mushroom). C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain > C10AA - Hmg coa reductase inhibitors D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor D009676 - Noxae > D000963 - Antimetabolites CONFIDENCE standard compound; EAWAG_UCHEM_ID 3139 CONFIDENCE standard compound; INTERNAL_ID 2212 Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol. Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.

   

Uridine

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

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.

   

Fumaric acid

(2E)-but-2-enedioic acid

C4H4O4 (116.011)


Fumaric acid appears as a colorless crystalline solid. The primary hazard is the threat to the environment. Immediate steps should be taken to limit spread to the environment. Combustible, though may be difficult to ignite. Used to make paints and plastics, in food processing and preservation, and for other uses. Fumaric acid is a butenedioic acid in which the C=C double bond has E geometry. It is an intermediate metabolite in the citric acid cycle. It has a role as a food acidity regulator, a fundamental metabolite and a geroprotector. It is a conjugate acid of a fumarate(1-). Fumaric acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Fumaric acid is a precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase. Fumarate is converted by fumarase to malate. A fumarate is a salt or ester of the organic compound fumaric acid, a dicarboxylic acid. Fumarate has recently been recognized as an oncometabolite. (A15199). As a food additive, fumaric acid is used to impart a tart taste to processed foods. It is also used as an antifungal agent in boxed foods such as cake mixes and flours, as well as tortillas. Fumaric acid is also added to bread to increase the porosity of the final baked product. It is used to impart a sour taste to sourdough and rye bread. In cake mixes, it is used to maintain a low pH and prevent clumping of the flours used in the mix. In fruit drinks, fumaric acid is used to maintain a low pH which, in turn, helps to stabilize flavor and color. Fumaric acid also prevents the growth of E. coli in beverages when used in combination with sodium benzoate. When added to wines, fumaric acid helps to prevent further fermentation and yet maintain low pH and eliminate traces of metallic elements. In this fashion, it helps to stabilize the taste of wine. Fumaric acid can also be added to dairy products, sports drinks, jams, jellies and candies. Fumaric acid helps to break down bonds between gluten proteins in wheat and helps to create a more pliable dough. Fumaric acid is used in paper sizing, printer toner, and polyester resin for making molded walls. Fumaric acid is a dicarboxylic acid. It is a precursor to L-malate in the Krebs tricarboxylic acid (TCA) cycle. It is formed by the oxidation of succinic acid by succinate dehydrogenase. Fumarate is converted by the enzyme fumarase to malate. Fumaric acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by fumarate. Fumaric acid is found to be associated with fumarase deficiency, which is an inborn error of metabolism. It is also a metabolite of Aspergillus. Produced industrially by fermentation of Rhizopus nigricans, or manufactured by catalytic or thermal isomerisation of maleic anhydride or maleic acid. Used as an antioxidant, acidulant, leavening agent and flavouring agent in foods. Present in raw lean fish. Dietary supplement. Used in powdered products since fumaric acid is less hygroscopic than other acids. A precursor to L-malate in the Krebs tricarboxylic acid cycle. It is formed by the oxidation of succinate by succinate dehydrogenase (wikipedia). Fumaric acid is also found in garden tomato, papaya, wild celery, and star fruit. Fumaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=110-17-8 (retrieved 2024-07-01) (CAS RN: 110-17-8). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite. Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

   

4-Hydroxybenzoic acid

4-hydroxybenzoic acid

C7H6O3 (138.0317)


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

   

Succinic acid

butanedioic acid

C4H6O4 (118.0266)


Succinic acid appears as white crystals or shiny white odorless crystalline powder. pH of 0.1 molar solution: 2.7. Very acid taste. (NTP, 1992) Succinic acid is an alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle. It has a role as a nutraceutical, a radiation protective agent, an anti-ulcer drug, a micronutrient and a fundamental metabolite. It is an alpha,omega-dicarboxylic acid and a C4-dicarboxylic acid. It is a conjugate acid of a succinate(1-). A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawleys Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851) Succinic acid is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). Succinic acid is a dicarboxylic acid. The anion, succinate, is a component of the citric acid cycle capable of donating electrons to the electron transfer chain. Succinic acid is created as a byproduct of the fermentation of sugar. It lends to fermented beverages such as wine and beer a common taste that is a combination of saltiness, bitterness and acidity. Succinate is commonly used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. Succinate plays a role in the citric acid cycle, an energy-yielding process and is metabolized by succinate dehydrogenase to fumarate. Succinate dehydrogenase (SDH) plays an important role in the mitochondria, being both part of the respiratory chain and the Krebs cycle. SDH with a covalently attached FAD prosthetic group, binds enzyme substrates (succinate and fumarate) and physiological regulators (oxaloacetate and ATP). Oxidizing succinate links SDH to the fast-cycling Krebs cycle portion where it participates in the breakdown of acetyl-CoA throughout the whole Krebs cycle. Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e.g. malate. (A3509) Mutations in the four genes encoding the subunits of succinate dehydrogenase are associated with a wide spectrum of clinical presentations (i.e.: Huntingtons disease. (A3510). Succinate also acts as an oncometabolite. Succinate inhibits 2-oxoglutarate-dependent histone and DNA demethylase enzymes, resulting in epigenetic silencing that affects neuroendocrine differentiation. A water-soluble, colorless crystal with an acid taste that is used as a chemical intermediate, in medicine, the manufacture of lacquers, and to make perfume esters. It is also used in foods as a sequestrant, buffer, and a neutralizing agent. (Hawleys Condensed Chemical Dictionary, 12th ed, p1099; McGraw-Hill Dictionary of Scientific and Technical Terms, 4th ed, p1851) Succinic acid (succinate) is a dicarboxylic acid. It is an important component of the citric acid or TCA cycle and is capable of donating electrons to the electron transfer chain. Succinate is found in all living organisms ranging from bacteria to plants to mammals. In eukaryotes, succinate is generated in the mitochondria via the tricarboxylic acid cycle (TCA). Succinate can readily be imported into the mitochondrial matrix by the n-butylmalonate- (or phenylsuccinate-) sensitive dicarboxylate carrier in exchange with inorganic phosphate or another organic acid, e. g. malate (PMID 16143825). Succinate can exit the mitochondrial matrix and function in the cytoplasm as well as the extracellular space. Succinate has multiple biological roles including roles as a metabolic intermediate and roles as a cell signalling molecule. Succinate can alter gene expression patterns, thereby modulating the epigenetic landscape or it can exhibit hormone-like signaling functions (PMID: 26971832). As such, succinate links cellular metabolism, especially ATP formation, to the regulation of cellular function. Succinate can be broken down or metabolized into fumarate by the enzyme succinate dehydrogenase (SDH), which is part of the electron transport chain involved in making ATP. Dysregulation of succinate synthesis, and therefore ATP synthesis, can happen in a number of genetic mitochondrial diseases, such as Leigh syndrome, and Melas syndrome. Succinate has been found to be associated with D-2-hydroxyglutaric aciduria, which is an inborn error of metabolism. Succinic acid has recently been identified as an oncometabolite or an endogenous, cancer causing metabolite. High levels of this organic acid can be found in tumors or biofluids surrounding tumors. Its oncogenic action appears to due to its ability to inhibit prolyl hydroxylase-containing enzymes. In many tumours, oxygen availability becomes limited (hypoxia) very quickly due to rapid cell proliferation and limited blood vessel growth. The major regulator of the response to hypoxia is the HIF transcription factor (HIF-alpha). Under normal oxygen levels, protein levels of HIF-alpha are very low due to constant degradation, mediated by a series of post-translational modification events catalyzed by the prolyl hydroxylase domain-containing enzymes PHD1, 2 and 3, (also known as EglN2, 1 and 3) that hydroxylate HIF-alpha and lead to its degradation. All three of the PHD enzymes are inhibited by succinate. In humans, urinary succinic acid is produced by Escherichia coli, Pseudomonas aeruginosa, Klebsiella pneumonia, Enterobacter, Acinetobacter, Proteus mirabilis, Citrobacter frundii, Enterococcus faecalis (PMID: 22292465). Succinic acid is also found in Actinobacillus, Anaerobiospirillum, Mannheimia, Corynebacterium and Basfia (PMID: 22292465; PMID: 18191255; PMID: 26360870). Succinic acid is widely distributed in higher plants and produced by microorganisms. It is found in cheeses and fresh meats. Succinic acid is a flavouring enhancer, pH control agent [DFC]. Succinic acid is also found in yellow wax bean, swamp cabbage, peanut, and abalone. An alpha,omega-dicarboxylic acid resulting from the formal oxidation of each of the terminal methyl groups of butane to the corresponding carboxy group. It is an intermediate metabolite in the citric acid cycle. COVID info from PDB, Protein Data Bank Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID S004 Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2]. Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2].

   

Tyrosol

4-hydroxy-Benzeneethanol;4-Hydroxyphenylethanol;beta-(4-Hydroxyphenyl)ethanol

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].

   

Ergosterol

(1R,3aR,7S,9aR,9bS,11aR)-1-[(2R,3E,5R)-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1H,2H,3H,3aH,6H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-ol

C28H44O (396.3392)


Ergosterol is a phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. It has a role as a fungal metabolite and a Saccharomyces cerevisiae metabolite. It is a 3beta-sterol, an ergostanoid, a 3beta-hydroxy-Delta(5)-steroid and a member of phytosterols. A steroid of interest both because its biosynthesis in FUNGI is a target of ANTIFUNGAL AGENTS, notably AZOLES, and because when it is present in SKIN of animals, ULTRAVIOLET RAYS break a bond to result in ERGOCALCIFEROL. Ergosterol is a natural product found in Gladiolus italicus, Ramaria formosa, and other organisms with data available. ergosterol is a metabolite found in or produced by Saccharomyces cerevisiae. A steroid occurring in FUNGI. Irradiation with ULTRAVIOLET RAYS results in formation of ERGOCALCIFEROL (vitamin D2). See also: Reishi (part of). Ergosterol, also known as provitamin D2, belongs to the class of organic compounds known as ergosterols and derivatives. These are steroids containing ergosta-5,7,22-trien-3beta-ol or a derivative thereof, which is based on the 3beta-hydroxylated ergostane skeleton. Thus, ergosterol is considered to be a sterol lipid molecule. Ergosterol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Ergosterol is the biological precursor to vitamin D2. It is turned into viosterol by ultraviolet light, and is then converted into ergocalciferol, which is a form of vitamin D. Ergosterol is a component of fungal cell membranes, serving the same function that cholesterol serves in animal cells. Ergosterol is not found in mammalian cell membranes. A phytosterol consisting of ergostane having double bonds at the 5,6-, 7,8- and 22,23-positions as well as a 3beta-hydroxy group. Ergosterol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=57-87-4 (retrieved 2024-07-12) (CAS RN: 57-87-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

   

3-4-hydroxyphenyl-propionate

3-(4-hydroxyphenyl)propanoic acid

C9H10O3 (166.063)


Desaminotyrosine, also known as 4-hydroxyphenylpropionic acid, is a normal constituent of human urine. It is a product of tyrosine metabolism; its concentration in urine increases in patients with gastrointestinal diseases. Desaminotyrosine is a major phenolic acid breakdown product of proanthocyanidin metabolism (PMID:15315398). Urinary desaminotyrosine is produced by Clostridium sporogenes and C. botulinum (PMID:29168502). Desaminotyrosine is also found in Acinetobacter, Bacteroides, Bifidobacteria, Bifidobacterium, Clostridium, Enterococcus, Escherichia, Eubacterium, Klebsiella, Lactobacillus, Pseudomonas, and Staphylococcus (PMID:29168502, 28393285, 19961416). Desaminotyrosine is a phenolic acid metabolite formed by the gut microflora detected after the consumption of whole grain. A normal constituent of human urine. A product of tyrosine metabolism; concentration in urine increases in patients with gastrointestinal diseases. (Dictionary of Organic Compounds) May also result from phenolic acid metabolism by colonic bacteria. (PMID 15315398) [HMDB]. Phloretic acid is found in many foods, some of which are arrowroot, olive, avocado, and peanut. Desaminotyrosine is a microbially associated metabolite protecting from influenza through augmentation of type I interferon signaling. Desaminotyrosine is a microbially associated metabolite protecting from influenza through augmentation of type I interferon signaling.

   

Mesoridazine

2-Methanesulphinyl-10-[2-(1-methyl-piperidin-2-yl)-ethyl]-10H-phenothiazine

C21H26N2OS2 (386.1486)


Mesoridazine is only found in individuals that have used or taken this drug. It is a phenothiazine antipsychotic with effects similar to chlorpromazine. [PubChem]Based upon animal studies, mesoridazine, as with other phenothiazines, acts indirectly on reticular formation, whereby neuronal activity into reticular formation is reduced without affecting its intrinsic ability to activate the cerebral cortex. In addition, the phenothiazines exhibit at least part of their activities through depression of hypothalamic centers. Neurochemically, the phenothiazines are thought to exert their effects by a central adrenergic blocking action. N - Nervous system > N05 - Psycholeptics > N05A - Antipsychotics > N05AC - Phenothiazines with piperidine structure D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents > D018492 - Dopamine Antagonists D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants C78272 - Agent Affecting Nervous System > C66883 - Dopamine Antagonist C78272 - Agent Affecting Nervous System > C29710 - Antipsychotic Agent

   

2-Furoic acid

furan-2-carboxylic acid

C5H4O3 (112.016)


Furoic acid is a metabolite that appears in the urine of workers occupationally exposed to furfural and is a marker of exposure to this compound. Furfural is a heterocyclic aldehyde that is commonly used as a solvent in industry. It is readily absorbed into the body via the lungs and has significant skin absorption. Furfural is an irritant of the eyes, mucous membranes, and skin and is a central nervous system depressant. Furfural as a confirmed animal carcinogen with unknown relevance to humans (It has been suggested that is a substance that produces hepatic cirrhosis). Once in the body, furfural is metabolized rapidly via oxidation to the metabolite furoic acid, which is then conjugated with glycine and excreted in the urine in both free and conjugated forms. (PMID: 3751566, 4630229, 12587683). 2-Furoic acid is a biomarker for the consumption of beer. 2-Furancarboxylic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=88-14-2 (retrieved 2024-07-10) (CAS RN: 88-14-2). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2].

   

Scytalone

3,4-Dihydro-3,6,8-trihydoroxy-1(2H)-napthalenone

C10H10O4 (194.0579)


   

6-Methylsalicylic acid

2-HYDROXY-6-METHYLBENZOIC ACID

C8H8O3 (152.0473)


A monohydroxybenzoic acid that is salicylic acid in which the hydrogen ortho to the carboxylic acid group is substituted by a methyl group. D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates

   

ent-8(14),15-Pimaradiene

7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene

C20H32 (272.2504)


ent-8(14),15-Pimaradiene is found in fruits. ent-8(14),15-Pimaradiene is a constituent of Aralia racemosa (American spikenard). Constituent of Aralia racemosa (American spikenard). ent-8(14),15-Pimaradiene is found in fruits.

   

Oblongolide

Oblongolide

C14H20O2 (220.1463)


   

fusicocca-2,10(14)-diene

3-Isopropyl-6,9,10a-trimethyl-1,2,4,5,6,6a,7,8,10,10a-decahydrodicyclopenta[a,d]cyclooctene

C20H32 (272.2504)


   

Phomopsin A

(2E)-2-{[(2E)-2-({[(2S)-1-[(3R,4S,7S,10S,11S)-14-chloro-3-ethyl-6,9,11,15-tetrahydroxy-3-methyl-10-(methylamino)-7-(prop-1-en-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),5,8,12,14-pentaene-4-carbonyl]-2,5-dihydro-1H-pyrrol-2-yl](hydroxy)methylidene}amino)-1-hydroxy-3-methylpent-2-en-1-ylidene]amino}but-2-enedioate

C36H45ClN6O12 (788.2784)


D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators Phomopsin A is a mycotoxin produced by Phomopsis leptostromiformi D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins

   

2,5-Furandicarboxylic acid

Furane-alpha,alpha-dicarboxylic acid

C6H4O5 (156.0059)


2,5-Furandicarboxylic acid is a normal urinary metabolite in humans. (PMID:14708889, 8087979, 2338430, 3711221). Dietary studies show that the furan derivatives or their precursors are of exogenous origin. They are originated from furan derivatives found in food prepared by strong heating. This may explain the absence of 2,5-furandicarboxylic acid in urine of breastfed children, and the absence of these acids in the urine of rats, pigs, cows, oxs, rabbits, and monkeys (PMID 4630229). 2,5-Furandicarboxylic acid is also a microbial metabolite, a product of the oxidation of hydroxymethylfurfural (HMF) by the enzyme furfural/HMF oxidoreductase which is found in the bacterium Cupriavidus basilensis. Cupriavidus basilensis is a gram-negative soil bacterium of the genus Cupriavidus and the family Burkholderiaceae. 2,5-Furandicarboxylic acid increases with the level of fructose consumed (PMID:20194784). 2,5-Furandicarboxylic acid is a normal urinary metabolite in humans. (PMIDs 14708889, 8087979, 2338430, 3711221) 2,5-Furandicarboxylic acid, detected in human urine, is an important renewable biotechnological building block because it serves as an environmentally friendly substitute for terephthalic acid in the production of polyesters[1].

   

7-Hydroxy-(S)-usnate

7-Hydroxy-(S)-usnate

C18H16O7 (344.0896)


   

Mevalonolactone

(+/-) tetrahydro-4-hydroxy-4-methyl-2H-pyran-2-one

C6H10O3 (130.063)


Mevalonolactone is a substance obtained by the dehydration of mevalonic acid and is rapidly converted back into mevalonic acid in water. Mevaolonic acid exists in equilibrium with mevalolactone, which is formed by internal condensation of mevalonic acids terminal alcohol and carboxylic acid functional groups. Mevalonic acid is a key intermediate in the biosynthesis of terpenes and steroids. Mevalonolactone is known ot inhibit HMG-CoA reductase activity. [HMDB] Mevalonolactone is a substance obtained by the dehydration of mevalonic acid and is rapidly converted back into mevalonic acid in water. Mevaolonic acid exists in equilibrium with mevalolactone, which is formed by internal condensation of mevalonic acids terminal alcohol and carboxylic acid functional groups. Mevalonic acid is a key intermediate in the biosynthesis of terpenes and steroids. Mevalonolactone is known ot inhibit HMG-CoA reductase activity. DL-Mevalonolactone ((±)-Mevalonolactone;Mevalolactone) is the δ-lactone form of mevalonic acid, a precursor in the mevalonate pathway. DL-Mevalonolactone (Mevalonolactone) decreases mitochondrial membrane potential (?Ψm), NAD(P)H content and the capacity to retain Ca2+ in the brain, besides inducing mitochondrial swelling[1][2].

   

Ergosterol peroxide

5-[(3E)-5,6-dimethylhept-3-en-2-yl]-6,10-dimethyl-16,17-dioxapentacyclo[13.2.2.0¹,⁹.0²,⁶.0¹⁰,¹⁵]nonadec-18-en-13-ol

C28H44O3 (428.329)


Ergosterol peroxide is found in fruits. Ergosterol peroxide is obtained from leaves of Ananas comosus (pineapple obtained from leaves of Ananas comosus (pineapple). Ergosterol peroxide is found in pineapple and fruits.

   

Phomopsin B

(2E)-2-[(2E)-2-{[(2S)-1-[(3R,4S,7S,10S,11S)-3-ethyl-11,15-dihydroxy-3-methyl-10-(methylamino)-6,9-dioxo-7-(prop-1-en-2-yl)-2-oxa-5,8-diazabicyclo[10.3.1]hexadeca-1(16),12,14-triene-4-carbonyl]-2,5-dihydro-1H-pyrrol-2-yl]formamido}-3-methylpent-2-enamido]but-2-enedioic acid

C36H46N6O12 (754.3174)


D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents Phomopsin B is a mycotoxin from Phomopsis leptostromiformis. D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins

   

2-hydroxy-Alternariol

2-hydroxy-Alternariol

C14H10O6 (274.0477)


   

But-2-enedioic acid

but-2-enedioic acid

C4H4O4 (116.011)


   

Cytosporone B

Ethyl 2-(3,5-dihydroxy-2-octanoylphenyl)acetic acid

C18H26O5 (322.178)


Cytosporone B (Csn-B; Dothiorelone G) is a naturally occurring nuclear orphan receptor Nur77/NR4A1 agonist with an EC50 of 0.278 nM.

   

usnic acid

4,10-diacetyl-11,13-dihydroxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),6,10,12-tetraene-3,5-dione

C18H16O7 (344.0896)


   

Mellein

(3R)-8-hydroxy-3-methyl-3,4-dihydro-1H-2-benzopyran-1-one

C10H10O3 (178.063)


Mellein, also known as (R)-mellein, is a member of the class of compounds known as 2-benzopyrans. 2-benzopyrans are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 2-position. Mellein is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Mellein can be found in cocoa powder, which makes mellein a potential biomarker for the consumption of this food product. Mellein is a dihydroisocoumarin, a phenolic compound produced by Aspergillus ochraceus .

   

ent-Sandaracopimaradiene

(4aS,4bS,7R,10aS)-7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene

C20H32 (272.2504)


Ent-sandaracopimaradiene, also known as (-)-8(14),15-isopimaradiene or (-)-isopimara-8(14),15-diene, is a member of the class of compounds known as diterpenoids. Diterpenoids are terpene compounds formed by four isoprene units. Thus, ent-sandaracopimaradiene is considered to be an isoprenoid lipid molecule. Ent-sandaracopimaradiene can be found in rice, which makes ent-sandaracopimaradiene a potential biomarker for the consumption of this food product.

   

Uridine

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

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.

   

Mellein

8-hydroxy-3-methyl-3,4-dihydroisochromen-1-one

C10H10O3 (178.063)


D009676 - Noxae > D011042 - Poisons > D009793 - Ochratoxins D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE isolated standard

   

Dicerandrol A

Dicerandrol A

C34H34O14 (666.1948)


A biaryl that is 5,5,7,7,9,9,10a,10a-octahydro-6H,6H-2,2-bixanthene substituted by acetoxy groups at C-5 and C-5, hydroxy groups at C-1, C-1, C-8 and C-8, hydroxymethyl groups at C-10a and C-10a, methyl groups at C-6 and C-6 and oxo groups at C-9 and C-9 respectively. A dimeric tetrahydroxanthone derivative isolated from Phomopsis longicolla, it exhibits antibacterial and cytotoxic activities.

   

Phomoxanthone B

(-)-Phomoxanthone B

C38H38O16 (750.216)


A member of the class of xanthones that is a dimer isolated from Phomopsis. It exhibits cytotoxic, antimalarial and antitubercular activities.

   

Phomoxanthone A

Phomoxanthone A

C38H38O16 (750.216)


A member of the class of xanthones that is a dimer isolated from Phomopsis. It exhibits cytotoxic, antimalarial and antitubercular activities.

   

5-Methylmellein

5-Methylmellein

C11H12O3 (192.0786)


   

Dicerandrol C

Dicerandrol C

C38H38O16 (750.216)


A biaryl that is 5,5,7,7,9,9,10a,10a-octahydro-6H,6H-2,2-bixanthene substituted by acetyloxy groups at C-5 and C-5, (acetyloxy)methyl group at C-10a and C-10a, hydroxy groups at C-1, C-1, C-8 and C-8, methyl groups at C-6 and C-6 and oxo groups at C-9 and C-9 respectively. A dimeric tetrahydroxanthone derivative isolated from Phomopsis longicolla, it exhibits antibacterial and cytotoxic activities.

   

Dicerandrol B

Dicerandrol B

C36H36O15 (708.2054)


A biaryl that is 5,5,7,7,9,9,10a,10a-octahydro-6H,6H-2,2-bixanthene substituted by acetyloxy groups at C-5 and C-5, (acetyloxy)methyl group at C-10a, hydroxy groups at C-1, C-1, C-8 and C-8, hydroxymethyl group at C-10a, methyl groups at C-6 and C-6 and oxo groups at C-9 and C-9 respectively. A dimeric tetrahydroxanthone derivative isolated from Phomopsis longicolla, it exhibits antibacterial and cytotoxic activities.

   

cytosporone C

cytosporone C

C16H22O4 (278.1518)


   

Phomonitroester

Phomonitroester

C11H13NO5 (239.0794)


   

Orsellic acid

2,4-Dihydroxy-6-methylbenzoic acid

C8H8O4 (168.0423)


Orsellinic acid is a compound produced by Lecanoric acid treated with alcohols. Lecanoric acid is a lichen depside isolated from a Parmotrema tinctorum specimen[1].

   

CYTOSPORONE B

CYTOSPORONE B

C18H26O5 (322.178)


Cytosporone B (Csn-B; Dothiorelone G) is a naturally occurring nuclear orphan receptor Nur77/NR4A1 agonist with an EC50 of 0.278 nM.

   

barceloneic acid A

2-hydroxy-6-[2-hydroxy-6-(hydroxymethyl)-4-methoxyphenoxy]-4-methylbenzoic acid

C16H16O7 (320.0896)


D000893 - Anti-Inflammatory Agents > D000894 - Anti-Inflammatory Agents, Non-Steroidal > D012459 - Salicylates

   

Xanthepinone

Xanthepinone

C16H12O8 (332.0532)


   

Phomosine G

Phomosine G

C18H18O6 (330.1103)


   

Ergosterol peroxide

Ergosterol peroxide

C28H44O3 (428.329)


   

Gladiolic acid

Gladiolic acid

C11H10O5 (222.0528)


   

barceloneic acid B

barceloneic acid B

C16H14O8 (334.0689)


   

6-hydroxy-6-isopropylcyclohex-1-enecarboxylic acid

6-hydroxy-6-isopropylcyclohex-1-enecarboxylic acid

C10H16O3 (184.1099)


   

oblongolide W2

oblongolide W2

C16H24O4 (280.1675)


   

Phomosine D

Phomosine D

C18H20O7 (348.1209)


   

Cytosporone O

Cytosporone O

C16H22O5 (294.1467)


   

4-[5-(1-hydroxyethyl)furan-2-yl]-4-oxobutanoic acid

4-[5-(1-hydroxyethyl)furan-2-yl]-4-oxobutanoic acid

C10H12O5 (212.0685)


   

6-O-Methyl-2-deprenylrheediaxanthone B

6-O-Methyl-2-deprenylrheediaxanthone B

C19H18O6 (342.1103)


An organic heterotetracyclic compound that is 1,2-dihydro-6H-furo[2,3-c]xanthene substituted by hydroxy groups at positions 5 and 10, a methoxy group at position 9 and methyl groups at positions 1, 1 and 2 and an oxo group at position 6. Isolated from the stem barks of Garcinia vieillardii, it exhibits antioxidant activity.

   

phomalevone A

phomalevone A

C30H26O10 (546.1526)


A biaryl that is 5,5,10a,10a-tetrahydro-9H,9H-2,2-bixanthene-9,9-dione substituted by hydroxy groups at positions 1, 1, 5, 5, 8 and 8 and methyl groups at positions 3, 3, 10a and 10a. Isolated from the cultures of a Hawaiian isolate of the fungus Phoma species, it exhibits antibacterial activity.

   

phomalevone C

phomalevone C

C30H24O10 (544.1369)


A biaryl that is 5,10a-dihydro-9H,9H-2,2-bixanthene-5,9,9(10aH)-trione substituted by hydroxy groups at positions 1, 1, 5, 8 and 8 and methyl groups at positions 3, 3, 10a and 10a. Isolated from the cultures of a Hawaiian isolate of the fungus Phoma species, it exhibits antibacterial and antifungal activities.

   

Phomalevone B

Phomalevone B

C30H26O10 (546.1526)


A member of the class of biphenyls that is 6,6-dimethylbiphenyl-2,2,4,4-tetrol which has been substituted by 3,6-dihydroxy-2-methylbenzoyl groups at positions 3 and 3. Isolated from the cultures of a Hawaiian isolate of the fungus Phoma species, it exhibits antibacterial and antifungal activities.

   

phomoarcherin C

phomoarcherin C

C23H30O4 (370.2144)


A natural product found in Phomopsis archeri.

   

4-butoxy-6-(1-hydroxypentyl)-5,6-dihydro-2H-pyran-2-one

4-butoxy-6-(1-hydroxypentyl)-5,6-dihydro-2H-pyran-2-one

C14H24O4 (256.1675)


   

Topopyrone B

Topopyrone B

C18H9ClO7 (372.0037)


A naphthochromene that is 4H-naphtho[2,3-g]chromene-4,6,11-trione substituted by a chloro group at position 8, hydroxy groups at positions 5, 7 and 9 and a methyl group at position 2. It is isolated from a fungal strain Phoma sp.BAUA2861 and acts as an inhibitor of the enzyme topoisomerase I. D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059004 - Topoisomerase I Inhibitors D004791 - Enzyme Inhibitors

   

Topopyrone A

Topopyrone A

C18H9ClO7 (372.0037)


A naphthochromene that is 4H-naphtho[2,3-h]chromene-4,7,12-trione substituted by a chloro group at position 10, hydroxy groups at positions 5, 9 and 11 and a methyl group at position 2. It is isolated from a fungal strain Phoma sp.BAUA2861 and acts as an inhibitor of the enzyme topoisomerase I. D000970 - Antineoplastic Agents > D059003 - Topoisomerase Inhibitors > D059004 - Topoisomerase I Inhibitors D004791 - Enzyme Inhibitors

   

Cytosporone Q

Cytosporone Q

C15H20O6 (296.126)


   

Cytosporone D

Cytosporone D

C16H22O5 (294.1467)


   

Cytosporone P

Cytosporone P

C15H20O6 (296.126)


   

oblongolide Y

oblongolide Y

C17H26O3 (278.1882)


   

Phomosine A

Phomosine A

C18H18O7 (346.1052)


   

Phomosine F

Phomosine F

C20H22O8 (390.1315)


   

2,4-Dihydroxy-3,6-dimethylbenzaldehyde

2,4-Dihydroxy-3,6-dimethylbenzaldehyde

C9H10O3 (166.063)


   

oblongolide X

oblongolide X

C16H24O4 (280.1675)


   

Cytosporone E

Cytosporone E

C15H20O5 (280.1311)


   

Phomopsin A

Phomopsin A

C36H45ClN6O12 (788.2784)


D050258 - Mitosis Modulators > D050256 - Antimitotic Agents > D050257 - Tubulin Modulators D000970 - Antineoplastic Agents > D050256 - Antimitotic Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins

   

Cytosporone A

Cytosporone A

C16H22O5 (294.1467)


   

2-Methyl-3-(2-formyl-3-hydroxy-5-methylphenoxy)-4,6-dihydroxybenzoic acid methyl ester

2-Methyl-3-(2-formyl-3-hydroxy-5-methylphenoxy)-4,6-dihydroxybenzoic acid methyl ester

C17H16O7 (332.0896)


   

cytosporic acid

cytosporic acid

C22H34O6 (394.2355)


A monocarboxylic acid that is 3,8-dimethyl-5-oxo-1,2,3,4,4a,8a-hexahydronaphthalene-1-carboxylic acid substituted by a (2R)-hexan-2-yl at position 7, a hydroxy group at position 6 and a 3-hydroxypropanoyl group at position 8. It is a fungal metabolite produced by Cytospora with HIV-1 integrase inhibitory activity.

   

oblongolide Z

oblongolide Z

C24H32O3 (368.2351)


   

Ergosterol

(3S,9S,10R,13R,14R,17R)-17-[(E,2R,5R)-5,6-dimethylhept-3-en-2-yl]-10,13-dimethyl-2,3,4,9,11,12,14,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-3-ol

C28H44O (396.3392)


Indicator of fungal contamination, especies in cereals. Occurs in yeast and fungi. The main fungal steroidand is also found in small amts. in higher plant prods., e.g. palm oil [DFC]. D018977 - Micronutrients > D014815 - Vitamins > D000072664 - Provitamins 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. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects. Ergosterol is the primary sterol found in fungi, with antioxidative, anti-proliferative, and anti-inflammatory effects.

   

Lovastatin

Lovastatin (Mevacor)

C24H36O5 (404.2563)


C - Cardiovascular system > C10 - Lipid modifying agents > C10A - Lipid modifying agents, plain > C10AA - Hmg coa reductase inhibitors D057847 - Lipid Regulating Agents > D000960 - Hypolipidemic Agents > D000924 - Anticholesteremic Agents D004791 - Enzyme Inhibitors > D019161 - Hydroxymethylglutaryl-CoA Reductase Inhibitors C78276 - Agent Affecting Digestive System or Metabolism > C29703 - Antilipidemic Agent C471 - Enzyme Inhibitor > C1655 - HMG-CoA Reductase Inhibitor CONFIDENCE standard compound; INTERNAL_ID 2212 D009676 - Noxae > D000963 - Antimetabolites relative retention time with respect to 9-anthracene Carboxylic Acid is 1.415 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.416 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.421 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.419 Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol. Lovastatin is a cell-permeable HMG-CoA reductase inhibitor used to lower cholesterol.

   

Uridine

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

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.

   

4-hydroxybenzoate

4-Hydroxybenzoic acid

C7H6O3 (138.0317)


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

   

Succinic acid

Succinic acid

C4H6O4 (118.0266)


Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2]. Succinic acid is a potent and orally active anxiolytic agent. Succinic acid is an intermediate product of the tricarboxylic acid cycle. Succinic acid can be used as a precursor of many industrially important chemicals in food, chemical and pharmaceutical industries[1][2].

   

(1R)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione

NCGC00380847-01!(1R)-2-chloro-1,7-dihydroxy-3,9-dimethoxy-1-methylbenzo[c]chromene-4,6-dione

C16H13ClO7 (352.035)


   

p-Hydroxybenzoic acid

p-Hydroxybenzoic acid

C7H6O3 (138.0317)


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

   

Fumaric Acid

(2Z)-2-Butenedioic acid

C4H4O4 (116.011)


Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite. Fumaric acid, associated with fumarase deficiency, is identified as an oncometabolite or an endogenous, cancer causing metabolite.

   

2,5-Furandicarboxylic acid

furan-2,5-dicarboxylic acid

C6H4O5 (156.0059)


2,5-Furandicarboxylic acid, detected in human urine, is an important renewable biotechnological building block because it serves as an environmentally friendly substitute for terephthalic acid in the production of polyesters[1].

   

mesoridazine

10-[2-(1-methylpiperidin-2-yl)ethyl]-2-methylsulfinylphenothiazine

C21H26N2OS2 (386.1486)


N - Nervous system > N05 - Psycholeptics > N05A - Antipsychotics > N05AC - Phenothiazines with piperidine structure D002492 - Central Nervous System Depressants > D014149 - Tranquilizing Agents > D014150 - Antipsychotic Agents D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D014149 - Tranquilizing Agents D018377 - Neurotransmitter Agents > D015259 - Dopamine Agents > D018492 - Dopamine Antagonists D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants C78272 - Agent Affecting Nervous System > C66883 - Dopamine Antagonist C78272 - Agent Affecting Nervous System > C29710 - Antipsychotic Agent

   

phloroglucinol

benzene-1,3,5-triol

C6H6O3 (126.0317)


A - Alimentary tract and metabolism > A03 - Drugs for functional gastrointestinal disorders > A03A - Drugs for functional gastrointestinal disorders D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents A benzenetriol with hydroxy groups at position 1, 3 and 5.

   

3,4-Dihydroxybenzoic acid

3,4-Dihydroxybenzoic acid

C7H6O4 (154.0266)


   

3-Hydroxypropanoic acid

3-Hydroxypropanoic acid

C3H6O3 (90.0317)


   

orsellinic acid

orsellinic acid

C8H8O4 (168.0423)


   

Mevalonolactone

D-Mevalonolactone

C6H10O3 (130.063)


   

ent-8(14),15-Pimaradiene

7-ethenyl-1,1,4a,7-tetramethyl-1,2,3,4,4a,4b,5,6,7,9,10,10a-dodecahydrophenanthrene

C20H32 (272.2504)


   

Phomopsidin

(2E,4E)-5-[(1S,2R,4aS,5S,8S,8aS)-2-[(E)-but-2-en-2-yl]-5-hydroxy-3,8-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalen-1-yl]penta-2,4-dienoic acid

C21H30O3 (330.2195)


   

4-hydroxy-4-methyloxan-2-one

4-hydroxy-4-methyloxan-2-one

C6H10O3 (130.063)


A member of the class of 2-pyranones that is tetrahydro-2H-pyran-2-one substituted by a methyl and hydroxy group at position 4.

   

Tyrosol

InChI=1\C8H10O2\c9-6-5-7-1-3-8(10)4-2-7\h1-4,9-10H,5-6H

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].

   

furoic acid

InChI=1\C5H4O3\c6-5(7)4-2-1-3-8-4\h1-3H,(H,6,7

C5H4O3 (112.016)


2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2]. 2-Furoic acid (Furan-2-carboxylic acid) is an organic compound produced through furfural oxidation[1]. 2-Furoic acid exhibits hypolipidemic effet, lowers both serum cholesterol and serum triglyceride levels in rats[2].

   

Malyngamide A

Malyngamide A

C29H45ClN2O6 (552.2966)


A natural product found in Lyngbya majuscula.

   

7-Epi-Zeaenol

7-Epi-Zeaenol

C19H24O7 (364.1522)


A macrolide that is a C-7 epimer of zeaenol. Isolated from Fungi, it exhibits inhibitory activity against NF-kappaB.

   

Furan-2,5-dicarboxylic acid

Furan-2,5-dicarboxylic acid

C6H4O5 (156.0059)


A member of the class of furans carrying two carboxy substituents at positions 2 and 5.

   

3-Nitropropanoic acid

3-Nitropropanoic acid

C3H5NO4 (119.0219)


A C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.

   

(3s)-8-hydroxy-7-methoxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

(3s)-8-hydroxy-7-methoxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

C12H14O4 (222.0892)


   

7,8-dihydroxy-10-methyl-7,8,9,10-tetrahydrooxecin-2-one

7,8-dihydroxy-10-methyl-7,8,9,10-tetrahydrooxecin-2-one

C10H14O4 (198.0892)


   

2-hydroxy-3,6,6,7b-tetramethyl-1h,2h,7h,7ah-cyclobuta[e]inden-4-one

2-hydroxy-3,6,6,7b-tetramethyl-1h,2h,7h,7ah-cyclobuta[e]inden-4-one

C15H20O2 (232.1463)


   

2-methoxy-3-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-methylidenecyclohexyl 4,5-dihydroxyhex-2-enoate

2-methoxy-3-[2-methyl-3-(3-methylbut-2-en-1-yl)oxiran-2-yl]-4-methylidenecyclohexyl 4,5-dihydroxyhex-2-enoate

C22H34O6 (394.2355)


   

[(1r,7ar)-1-[(1s)-1-[(2r,3s,4s)-3-hydroxy-4,5,5-trimethyloxolan-2-yl]ethyl]-7a-methyl-5-oxo-2,3,6,7-tetrahydro-1h-inden-4-yl]acetic acid

[(1r,7ar)-1-[(1s)-1-[(2r,3s,4s)-3-hydroxy-4,5,5-trimethyloxolan-2-yl]ethyl]-7a-methyl-5-oxo-2,3,6,7-tetrahydro-1h-inden-4-yl]acetic acid

C21H32O5 (364.225)


   

(2r)-2,3-dihydroxypropyl (2e,4e,8e,13s)-13-hydroxytetradeca-2,4,8-trienoate

(2r)-2,3-dihydroxypropyl (2e,4e,8e,13s)-13-hydroxytetradeca-2,4,8-trienoate

C17H28O5 (312.1937)


   

2-(2-hydroxyethyl)-6-(hydroxymethyl)-4-(3-methoxy-5-methylphenoxy)phenol

2-(2-hydroxyethyl)-6-(hydroxymethyl)-4-(3-methoxy-5-methylphenoxy)phenol

C17H20O5 (304.1311)


   

5,6,16-trihydroxy-7,9,12,13-tetramethyl-14-(2-methylpropyl)-5h,6h,7h,8h,10ah,13h,13ah,14h-oxacyclododeca[2,3-d]isoindol-2-one

5,6,16-trihydroxy-7,9,12,13-tetramethyl-14-(2-methylpropyl)-5h,6h,7h,8h,10ah,13h,13ah,14h-oxacyclododeca[2,3-d]isoindol-2-one

C25H37NO5 (431.2672)


   

(4s)-8-hydroxy-5-(hydroxymethyl)-6-methoxy-4-methyl-3-methylidene-4h-2-benzopyran-1-one

(4s)-8-hydroxy-5-(hydroxymethyl)-6-methoxy-4-methyl-3-methylidene-4h-2-benzopyran-1-one

C13H14O5 (250.0841)


   

methyl 4-hydroxy-6-(2-hydroxyethyl)-8-methoxy-9-oxoxanthene-3-carboxylate

methyl 4-hydroxy-6-(2-hydroxyethyl)-8-methoxy-9-oxoxanthene-3-carboxylate

C18H16O7 (344.0896)


   

(2s)-5-[(2r,3s,6e,8r,9r)-3,8-dihydroxy-9-methyl-10-oxo-2,3,4,5,8,9-hexahydrooxecin-2-yl]pentan-2-yl acetate

(2s)-5-[(2r,3s,6e,8r,9r)-3,8-dihydroxy-9-methyl-10-oxo-2,3,4,5,8,9-hexahydrooxecin-2-yl]pentan-2-yl acetate

C17H28O6 (328.1886)


   

(3s,3ar,5ar,7s,9as,9br)-3,3a-dihydroxy-7,9b-dimethyl-3h,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

(3s,3ar,5ar,7s,9as,9br)-3,3a-dihydroxy-7,9b-dimethyl-3h,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

C14H20O4 (252.1362)


   

1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4,7-dihydroxy-6-[(4-hydroxy-4,6-dimethyloct-2-enoyl)oxy]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4,7-dihydroxy-6-[(4-hydroxy-4,6-dimethyloct-2-enoyl)oxy]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

C33H44O13 (648.2782)


   

3-hydroxy-4-(hydroxymethyl)-7-methoxy-6-methyl-3h-2-benzofuran-1-one

3-hydroxy-4-(hydroxymethyl)-7-methoxy-6-methyl-3h-2-benzofuran-1-one

C11H12O5 (224.0685)


   

3-[(7s,13s,21s,24r,27r)-5,8,11,14,22,25,28-heptahydroxy-24-(c-hydroxycarbonimidoylmethyl)-10,30-bis(2-hydroxyethyl)-27-[(1s)-1-hydroxyethyl]-21-(hydroxymethyl)-7-methyl-17,31-dioxo-3-(tetradecan-2-yl)-1-oxa-6,9,12,15,20,23,26,29-octaazacyclotritriaconta-5,8,11,14,22,25,28-heptaen-13-yl]propanoic acid

3-[(7s,13s,21s,24r,27r)-5,8,11,14,22,25,28-heptahydroxy-24-(c-hydroxycarbonimidoylmethyl)-10,30-bis(2-hydroxyethyl)-27-[(1s)-1-hydroxyethyl]-21-(hydroxymethyl)-7-methyl-17,31-dioxo-3-(tetradecan-2-yl)-1-oxa-6,9,12,15,20,23,26,29-octaazacyclotritriaconta-5,8,11,14,22,25,28-heptaen-13-yl]propanoic acid

C51H89N9O17 (1099.6376)


   

methyl 3-{2-[(acetyloxy)methyl]-3-hydroxy-5-methylphenoxy}-4,6-dihydroxy-2,5-dimethylbenzoate

methyl 3-{2-[(acetyloxy)methyl]-3-hydroxy-5-methylphenoxy}-4,6-dihydroxy-2,5-dimethylbenzoate

C20H22O8 (390.1315)


   

7,16-dihydroxy-14-methoxy-5-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one

7,16-dihydroxy-14-methoxy-5-methyl-2,10-dioxatricyclo[10.4.0.0³,⁸]hexadeca-1(16),3,5,7,12,14-hexaen-9-one

C16H14O6 (302.079)


   

3-heptyl-4,5,6-trihydroxy-3h-2-benzofuran-1-one

3-heptyl-4,5,6-trihydroxy-3h-2-benzofuran-1-one

C15H20O5 (280.1311)


   

8-hydroxy-7,9b-dimethyl-3h,3ah,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

8-hydroxy-7,9b-dimethyl-3h,3ah,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

C14H20O3 (236.1412)


   

2,6-dimethoxy-4-(5-methoxy-3,4-dimethyloxolan-2-yl)phenol

2,6-dimethoxy-4-(5-methoxy-3,4-dimethyloxolan-2-yl)phenol

C15H22O5 (282.1467)


   

8,14,23,25,28-pentahydroxy-6,21-dimethoxyoctacyclo[14.11.1.0²,¹¹.0²,¹⁵.0⁴,⁹.0¹³,¹⁷.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-4,6,8,19,21,23,25-heptaene-3,10,12,18,27-pentone

8,14,23,25,28-pentahydroxy-6,21-dimethoxyoctacyclo[14.11.1.0²,¹¹.0²,¹⁵.0⁴,⁹.0¹³,¹⁷.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-4,6,8,19,21,23,25-heptaene-3,10,12,18,27-pentone

C30H22O12 (574.1111)


   

methyl 4,8-dihydroxy-6-(2-hydroxyethyl)-9-oxoxanthene-3-carboxylate

methyl 4,8-dihydroxy-6-(2-hydroxyethyl)-9-oxoxanthene-3-carboxylate

C17H14O7 (330.0739)


   

ethyl (2e,4e,8e)-13-hydroxytetradeca-2,4,8-trienoate

ethyl (2e,4e,8e)-13-hydroxytetradeca-2,4,8-trienoate

C16H26O3 (266.1882)


   

(1s,13r,14s,19r)-10-hydroxy-1,14,18,18-tetramethyl-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9-triene-7,17-dione

(1s,13r,14s,19r)-10-hydroxy-1,14,18,18-tetramethyl-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3(11),4(8),9-triene-7,17-dione

C23H28O5 (384.1937)


   

methyl 2-(3,5-dihydroxy-2-octylphenyl)acetate

methyl 2-(3,5-dihydroxy-2-octylphenyl)acetate

C17H26O4 (294.1831)


   

(3s,3ar,4s,5r,6s,6ar,10s,12r,15r,15ar)-3-benzyl-1,5,6,12-tetrahydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

(3s,3ar,4s,5r,6s,6ar,10s,12r,15r,15ar)-3-benzyl-1,5,6,12-tetrahydroxy-4,5,10,12-tetramethyl-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

C30H41NO6 (511.2934)


   

4,7-dihydroxy-1-[4-hydroxy-3-(2-methyl-3-phenylpropylidene)butyl]-6-[(3-hydroxy-6-methyloctanoyl)oxy]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

4,7-dihydroxy-1-[4-hydroxy-3-(2-methyl-3-phenylpropylidene)butyl]-6-[(3-hydroxy-6-methyloctanoyl)oxy]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

C32H44O14 (652.2731)


   

(3as,5ar,7r,8r,9as,9br)-8-hydroxy-7,9b-dimethyl-3h,3ah,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

(3as,5ar,7r,8r,9as,9br)-8-hydroxy-7,9b-dimethyl-3h,3ah,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

C14H20O3 (236.1412)


   

{1-acetyl-1-hydroxy-9b-methyl-3h,3ah,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-7-yl}methyl acetate

{1-acetyl-1-hydroxy-9b-methyl-3h,3ah,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-7-yl}methyl acetate

C18H26O5 (322.178)


   

7,8-dihydroxy-10-(1-hydroxypropyl)-7,8,9,10-tetrahydrooxecin-2-one

7,8-dihydroxy-10-(1-hydroxypropyl)-7,8,9,10-tetrahydrooxecin-2-one

C12H18O5 (242.1154)


   

methyl 3-(2-formyl-3-hydroxy-5-methylphenoxy)-4,6-dihydroxy-2-methylbenzoate

methyl 3-(2-formyl-3-hydroxy-5-methylphenoxy)-4,6-dihydroxy-2-methylbenzoate

C17H16O7 (332.0896)


   

8,10,14,23,25,28-hexahydroxy-6,21-dimethoxyoctacyclo[14.11.1.0²,¹¹.0²,¹⁵.0⁴,⁹.0¹³,¹⁷.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone

8,10,14,23,25,28-hexahydroxy-6,21-dimethoxyoctacyclo[14.11.1.0²,¹¹.0²,¹⁵.0⁴,⁹.0¹³,¹⁷.0¹⁷,²⁶.0¹⁹,²⁴]octacosa-4,6,8,10,19,21,23,25-octaene-3,12,18,27-tetrone

C30H22O12 (574.1111)


   

(2s,7r)-4,10-diacetyl-11-hydroxy-7,13-dimethoxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),10,12-triene-3,5-dione

(2s,7r)-4,10-diacetyl-11-hydroxy-7,13-dimethoxy-2,12-dimethyl-8-oxatricyclo[7.4.0.0²,⁷]trideca-1(9),10,12-triene-3,5-dione

C20H22O8 (390.1315)


   

(3r,6r,7r)-3-[(3e)-1,2-dihydroxypent-3-en-1-yl]-6,7-dihydroxy-7-methyl-4,6-dihydro-3h-2-benzopyran-8-one

(3r,6r,7r)-3-[(3e)-1,2-dihydroxypent-3-en-1-yl]-6,7-dihydroxy-7-methyl-4,6-dihydro-3h-2-benzopyran-8-one

C15H20O6 (296.126)


   

3-(hydroxymethyl)-6,8-dimethoxyisochromen-1-one

3-(hydroxymethyl)-6,8-dimethoxyisochromen-1-one

C12H12O5 (236.0685)


   

2-{2,6-dihydroxy-7,7a-dimethyl-2h,6h,7h,7bh-naphtho[1,2-b]oxiren-1a-yl}prop-2-en-1-yl acetate

2-{2,6-dihydroxy-7,7a-dimethyl-2h,6h,7h,7bh-naphtho[1,2-b]oxiren-1a-yl}prop-2-en-1-yl acetate

C17H22O5 (306.1467)


   

8-methoxy-2-methyl-5h-chromeno[4,3-b]pyridine-10-carboxylic acid

8-methoxy-2-methyl-5h-chromeno[4,3-b]pyridine-10-carboxylic acid

C15H13NO4 (271.0845)


   

7,11,14,15-tetramethyl-3,6-dioxatetracyclo[12.4.0.0⁴,¹⁸.0⁵,⁷]octadeca-10,17-diene-4,17-diol

7,11,14,15-tetramethyl-3,6-dioxatetracyclo[12.4.0.0⁴,¹⁸.0⁵,⁷]octadeca-10,17-diene-4,17-diol

C20H30O4 (334.2144)


   

10-hydroxy-1,14,18,18-tetramethyl-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-triene-7,17-dione

10-hydroxy-1,14,18,18-tetramethyl-2,6-dioxapentacyclo[11.8.0.0³,¹¹.0⁴,⁸.0¹⁴,¹⁹]henicosa-3,8,10-triene-7,17-dione

C23H28O5 (384.1937)


   

(1r,3r,4s,7e,11s,12s,13s)-3,4,7,11-tetramethyl-14,18-dioxatetracyclo[9.6.1.0⁴,¹⁶.0¹³,¹⁷]octadeca-7,16-diene-12,13-diol

(1r,3r,4s,7e,11s,12s,13s)-3,4,7,11-tetramethyl-14,18-dioxatetracyclo[9.6.1.0⁴,¹⁶.0¹³,¹⁷]octadeca-7,16-diene-12,13-diol

C20H30O4 (334.2144)


   

7-hydroxy-8-methoxy-2-methyl-5h-chromeno[4,3-b]pyridine-10-carboxylic acid

7-hydroxy-8-methoxy-2-methyl-5h-chromeno[4,3-b]pyridine-10-carboxylic acid

C15H13NO5 (287.0794)


   

5,13-dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadecane-2,10-dione

5,13-dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadecane-2,10-dione

C16H28O6 (316.1886)


   

16-hydroxy-5,9,12,13,16-pentamethyl-4-oxatricyclo[10.3.1.0³,⁵]hexadeca-1(15),8-dien-2-one

16-hydroxy-5,9,12,13,16-pentamethyl-4-oxatricyclo[10.3.1.0³,⁵]hexadeca-1(15),8-dien-2-one

C20H30O3 (318.2195)


   

(1s,2s,4s)-4-isopropyl-1-methylcyclohexane-1,2,4-triol

(1s,2s,4s)-4-isopropyl-1-methylcyclohexane-1,2,4-triol

C10H20O3 (188.1412)


   

3-[(1s,2s,4ar,6s,8as)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-5-{2,5-dihydroxy-7-oxabicyclo[4.1.0]heptan-2-yl}-1,4-dihydroxypyridin-2-one

3-[(1s,2s,4ar,6s,8as)-2,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydronaphthalene-1-carbonyl]-5-{2,5-dihydroxy-7-oxabicyclo[4.1.0]heptan-2-yl}-1,4-dihydroxypyridin-2-one

C24H31NO7 (445.21)


   

methyl 4-hydroxy-5,8-dimethoxy-9-oxo-6-(1,3,4-trihydroxybutan-2-yl)xanthene-1-carboxylate

methyl 4-hydroxy-5,8-dimethoxy-9-oxo-6-(1,3,4-trihydroxybutan-2-yl)xanthene-1-carboxylate

C21H22O10 (434.1213)


   

(5s,7s,10as,13s,13as,14s,16as)-5,16-dihydroxy-7-(hydroxymethyl)-9,12,13-trimethyl-14-(2-methylpropyl)-5h,6h,7h,8h,10ah,13h,13ah,14h-oxacyclododeca[3,2-d]isoindol-2-one

(5s,7s,10as,13s,13as,14s,16as)-5,16-dihydroxy-7-(hydroxymethyl)-9,12,13-trimethyl-14-(2-methylpropyl)-5h,6h,7h,8h,10ah,13h,13ah,14h-oxacyclododeca[3,2-d]isoindol-2-one

C25H37NO5 (431.2672)


   

3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one

3,4,8-trihydroxy-6-methoxy-3,4-dihydro-2h-naphthalen-1-one

C11H12O5 (224.0685)


   

(1r,4s,9s,10s,13r)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane

(1r,4s,9s,10s,13r)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane

C20H32 (272.2504)


   

(5r,5as,7s,9as,9br)-5-hydroxy-7,9b-dimethyl-3h,5h,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

(5r,5as,7s,9as,9br)-5-hydroxy-7,9b-dimethyl-3h,5h,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

C14H20O3 (236.1412)


   

1-(5-benzyl-4,6-dihydroxy-3-methylidenehexyl)-6-[(4,6-dimethyloct-2-enoyl)oxy]-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

1-(5-benzyl-4,6-dihydroxy-3-methylidenehexyl)-6-[(4,6-dimethyloct-2-enoyl)oxy]-4,7-dihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

C33H44O14 (664.2731)


   

4-hydroxy-2-(hydroxymethyl)-8,10b-dimethyl-2h,4h,4ah,6ah,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-1-one

4-hydroxy-2-(hydroxymethyl)-8,10b-dimethyl-2h,4h,4ah,6ah,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-1-one

C16H24O4 (280.1675)


   

(3r,4s)-8-hydroxy-4-methoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

(3r,4s)-8-hydroxy-4-methoxy-3-methyl-3,4-dihydro-2-benzopyran-1-one

C11H12O4 (208.0736)


   

4-methoxy-7-propyl-5h,7h,8h-pyrano[3,2-c]pyran-2-one

4-methoxy-7-propyl-5h,7h,8h-pyrano[3,2-c]pyran-2-one

C12H16O4 (224.1049)


   

7-hydroxy-7,9b-dimethyl-3h,3ah,5ah,6h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

7-hydroxy-7,9b-dimethyl-3h,3ah,5ah,6h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

C14H20O3 (236.1412)


   

7-hydroxyoct-2-enoic acid

7-hydroxyoct-2-enoic acid

C8H14O3 (158.0943)


   

(13r)-13-hydroxypentadeca-6,7-dien-9,11-diynoic acid

(13r)-13-hydroxypentadeca-6,7-dien-9,11-diynoic acid

C15H18O3 (246.1256)


   

(1s,3s,4s,5r,6r,7r)-1-[(3e)-3,5-dimethyl-6-phenylhex-3-en-1-yl]-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

(1s,3s,4s,5r,6r,7r)-1-[(3e)-3,5-dimethyl-6-phenylhex-3-en-1-yl]-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

C23H28O11 (480.1632)


   

(2r,3s,5r,6r,8r)-8-[(1e)-dec-1-en-1-yl]-4,9-dioxatricyclo[5.3.0.0³,⁵]dec-1(7)-ene-2,6-diol

(2r,3s,5r,6r,8r)-8-[(1e)-dec-1-en-1-yl]-4,9-dioxatricyclo[5.3.0.0³,⁵]dec-1(7)-ene-2,6-diol

C18H28O4 (308.1987)


   

3-methyl-2-(methylamino)-n-[6,12,18-trihydroxy-14-(hydroxymethyl)-2,17-diisopropyl-10,16,20,22,26-pentamethyl-5,11,23-tris(2-methylpropyl)-3,9,15,21,24,28-hexaoxo-8-(sec-butyl)-1,4,25-trioxa-7,10,13,16,19,22-hexaazacyclooctacosa-6,12,18-trien-27-yl]pentanimidic acid

3-methyl-2-(methylamino)-n-[6,12,18-trihydroxy-14-(hydroxymethyl)-2,17-diisopropyl-10,16,20,22,26-pentamethyl-5,11,23-tris(2-methylpropyl)-3,9,15,21,24,28-hexaoxo-8-(sec-butyl)-1,4,25-trioxa-7,10,13,16,19,22-hexaazacyclooctacosa-6,12,18-trien-27-yl]pentanimidic acid

C54H96N8O14 (1080.7046)


   

6-[(4e,6e,12e,14e)-3,9-dihydroxy-6,8,10,14,16,18-hexamethylicosa-4,6,12,14-tetraen-2-yl]-3-[3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-hydroxypyran-2-one

6-[(4e,6e,12e,14e)-3,9-dihydroxy-6,8,10,14,16,18-hexamethylicosa-4,6,12,14-tetraen-2-yl]-3-[3,4-dihydroxy-6-(hydroxymethyl)oxan-2-yl]-4-hydroxypyran-2-one

C37H58O9 (646.4081)


   

(1s,6s,7r)-6,7-dihydroxy-1-[(1r)-1-hydroxybutyl]-3,5,6,7-tetrahydro-1h-2-benzofuran-4-one

(1s,6s,7r)-6,7-dihydroxy-1-[(1r)-1-hydroxybutyl]-3,5,6,7-tetrahydro-1h-2-benzofuran-4-one

C12H18O5 (242.1154)


   

4-{5-[(1r)-1-hydroxyethyl]furan-2-yl}-4-oxobutanoic acid

4-{5-[(1r)-1-hydroxyethyl]furan-2-yl}-4-oxobutanoic acid

C10H12O5 (212.0685)


   

(1s,3r,5s,6s,15r,18e,21s,23s)-5,10-dihydroxy-6,12,17,17,21,27-hexamethyl-7,22,24,28-tetraoxahexacyclo[21.4.3.0¹,²³.0³,²¹.0⁶,¹⁵.0⁸,¹³]triaconta-8,10,12,18,26-pentaene-25,29-dione

(1s,3r,5s,6s,15r,18e,21s,23s)-5,10-dihydroxy-6,12,17,17,21,27-hexamethyl-7,22,24,28-tetraoxahexacyclo[21.4.3.0¹,²³.0³,²¹.0⁶,¹⁵.0⁸,¹³]triaconta-8,10,12,18,26-pentaene-25,29-dione

C32H40O8 (552.2723)


   

(3s,5r,8z,12s,13s,14s,16r)-14,16-dihydroxy-5,9,12,13,16-pentamethyl-4-oxatricyclo[10.3.1.0³,⁵]hexadeca-1(15),8-dien-2-one

(3s,5r,8z,12s,13s,14s,16r)-14,16-dihydroxy-5,9,12,13,16-pentamethyl-4-oxatricyclo[10.3.1.0³,⁵]hexadeca-1(15),8-dien-2-one

C20H30O4 (334.2144)


   

(1s,4'r)-4',5-dihydroxy-2,3-dihydrospiro[naphthalene-1,2'-oxolane]-4,5'-dione

(1s,4'r)-4',5-dihydroxy-2,3-dihydrospiro[naphthalene-1,2'-oxolane]-4,5'-dione

C13H12O5 (248.0685)


   

2-(3,7-dihydroxy-2,2,4,6-tetramethyl-1,3-dihydroinden-5-yl)ethyl acetate

2-(3,7-dihydroxy-2,2,4,6-tetramethyl-1,3-dihydroinden-5-yl)ethyl acetate

C17H24O4 (292.1675)


   

(1s,2r,5r,6s)-5-(2-hydroxypropan-2-yl)-2-methyl-7-oxabicyclo[4.1.0]heptan-2-ol

(1s,2r,5r,6s)-5-(2-hydroxypropan-2-yl)-2-methyl-7-oxabicyclo[4.1.0]heptan-2-ol

C10H18O3 (186.1256)


   

(1s,5r,6r)-5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-chloro-2-hydroxybenzoate

(1s,5r,6r)-5,6-dihydroxy-3-(hydroxymethyl)-2-oxocyclohex-3-en-1-yl 3-chloro-2-hydroxybenzoate

C14H13ClO7 (328.035)


   

3-(2-{[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}propyl)-8-hydroxy-6-methoxyisochromen-1-one

3-(2-{[3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy}propyl)-8-hydroxy-6-methoxyisochromen-1-one

C20H26O10 (426.1526)


   

2-(hydroxymethyl)-5-methoxy-7-(3-methyl-2-oxobut-3-en-1-yl)naphthalene-1-carbaldehyde

2-(hydroxymethyl)-5-methoxy-7-(3-methyl-2-oxobut-3-en-1-yl)naphthalene-1-carbaldehyde

C18H18O4 (298.1205)


   

1,6-dihydroxy-10a-(methylsulfanyl)-3-(phenylmethylidene)-5ah,6h,10h-pyrazino[1,2-a]indol-4-one

1,6-dihydroxy-10a-(methylsulfanyl)-3-(phenylmethylidene)-5ah,6h,10h-pyrazino[1,2-a]indol-4-one

C19H18N2O3S (354.1038)


   

7,8-dihydroxy-4-methoxy-10-propyl-3,4,7,8,9,10-hexahydrooxecin-2-one

7,8-dihydroxy-4-methoxy-10-propyl-3,4,7,8,9,10-hexahydrooxecin-2-one

C13H22O5 (258.1467)


   

(1r,9r,17s,20r)-17-(chloromethyl)-13,16,16,20-tetramethyl-2,15,18-trioxapentacyclo[8.8.1.1¹,⁹.0³,⁸.0¹⁴,¹⁹]icosa-3,5,7,10,12,14(19)-hexaene-7,9,11-triol

(1r,9r,17s,20r)-17-(chloromethyl)-13,16,16,20-tetramethyl-2,15,18-trioxapentacyclo[8.8.1.1¹,⁹.0³,⁸.0¹⁴,¹⁹]icosa-3,5,7,10,12,14(19)-hexaene-7,9,11-triol

C22H23ClO6 (418.1183)


   

(5s,8r,13s,16r)-5,13-dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadecane-2,10-dione

(5s,8r,13s,16r)-5,13-dihydroxy-8,16-dimethyl-1,9-dioxacyclohexadecane-2,10-dione

C16H28O6 (316.1886)


   

(3r)-6-chloro-5,8-dihydroxy-3-propyl-3,4-dihydro-2-benzopyran-1-one

(3r)-6-chloro-5,8-dihydroxy-3-propyl-3,4-dihydro-2-benzopyran-1-one

C12H13ClO4 (256.0502)


   

6-[(4,6-dimethyloct-2-enoyl)oxy]-4,7-dihydroxy-1-(3-{[(1-hydroxyethylidene)amino]methyl}-5-methyl-6-phenylhex-3-en-1-yl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

6-[(4,6-dimethyloct-2-enoyl)oxy]-4,7-dihydroxy-1-(3-{[(1-hydroxyethylidene)amino]methyl}-5-methyl-6-phenylhex-3-en-1-yl)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

C35H47NO13 (689.3047)


   

ethyl 13-hydroxytetradeca-2,4,8-trienoate

ethyl 13-hydroxytetradeca-2,4,8-trienoate

C16H26O3 (266.1882)


   

1-[(2r,3s,5r,6r,8r)-2,6-dihydroxy-4,9-dioxatricyclo[5.3.0.0³,⁵]dec-1(7)-en-8-yl]decan-2-one

1-[(2r,3s,5r,6r,8r)-2,6-dihydroxy-4,9-dioxatricyclo[5.3.0.0³,⁵]dec-1(7)-en-8-yl]decan-2-one

C18H28O5 (324.1937)


   

4,6,7-trihydroxy-1-[4-hydroxy-3-(2-methyl-3-phenylpropylidene)butyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

4,6,7-trihydroxy-1-[4-hydroxy-3-(2-methyl-3-phenylpropylidene)butyl]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

C23H28O12 (496.1581)


   

(2s,3s)-2-[(1r,6s,7r,8s)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]-6-oxo-2,3-dihydropyran-3-yl acetate

(2s,3s)-2-[(1r,6s,7r,8s)-8-methyl-9-oxabicyclo[4.2.1]nona-2,4-dien-7-yl]-6-oxo-2,3-dihydropyran-3-yl acetate

C16H18O5 (290.1154)


   

[(5s,5's,6s,6's,10as,10'as)-5,5'-bis(acetyloxy)-1,1',9,9'-tetrahydroxy-10'a-(hydroxymethyl)-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[4,4'-bixanthen]-10a-yl]methyl acetate

[(5s,5's,6s,6's,10as,10'as)-5,5'-bis(acetyloxy)-1,1',9,9'-tetrahydroxy-10'a-(hydroxymethyl)-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[4,4'-bixanthen]-10a-yl]methyl acetate

C36H36O15 (708.2054)


   

7-(hydroxymethyl)-9b-methyl-3h,3ah,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

7-(hydroxymethyl)-9b-methyl-3h,3ah,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

C14H20O3 (236.1412)


   

(1r,4s,9s,10s,13s)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane

(1r,4s,9s,10s,13s)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane

C20H32 (272.2504)


   

1-[(1s,2s,4ar,6r,8as)-1,2,6-trimethyl-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl]-2,3-dihydroxypropan-1-one

1-[(1s,2s,4ar,6r,8as)-1,2,6-trimethyl-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl]-2,3-dihydroxypropan-1-one

C16H26O3 (266.1882)


   

1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

1-(3,5-dimethyl-6-phenylhex-3-en-1-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

C23H28O11 (480.1632)


   

8-hydroxy-7-methoxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

8-hydroxy-7-methoxy-3,5-dimethyl-3,4-dihydro-2-benzopyran-1-one

C12H14O4 (222.0892)


   

(2s,3s)-2-[(1z)-4-hydroxy-3-oxopent-1-en-1-yl]-6-oxo-2,3-dihydropyran-3-yl (2e)-2-methylbut-2-enoate

(2s,3s)-2-[(1z)-4-hydroxy-3-oxopent-1-en-1-yl]-6-oxo-2,3-dihydropyran-3-yl (2e)-2-methylbut-2-enoate

C15H18O6 (294.1103)


   

4,9-dihydroxy-10-(4-hydroxypentyl)-3-methyl-3,4,7,8,9,10-hexahydrooxecin-2-one

4,9-dihydroxy-10-(4-hydroxypentyl)-3-methyl-3,4,7,8,9,10-hexahydrooxecin-2-one

C15H26O5 (286.178)


   

{8-[5-(acetyloxy)-1,9-dihydroxy-10a-(hydroxymethyl)-6-methyl-8-oxo-6,7-dihydro-5h-xanthen-2-yl]-5-hydroxy-2-(3-methyl-5-oxooxolan-2-yl)-4-oxo-3h-1-benzopyran-2-yl}methyl acetate

{8-[5-(acetyloxy)-1,9-dihydroxy-10a-(hydroxymethyl)-6-methyl-8-oxo-6,7-dihydro-5h-xanthen-2-yl]-5-hydroxy-2-(3-methyl-5-oxooxolan-2-yl)-4-oxo-3h-1-benzopyran-2-yl}methyl acetate

C34H34O14 (666.1948)


   

4-hydroxy-3,5-dimethyl-6-(3-methylpent-1-en-1-yl)oxan-2-one

4-hydroxy-3,5-dimethyl-6-(3-methylpent-1-en-1-yl)oxan-2-one

C13H22O3 (226.1569)


   

3-methyl-2-(methylamino)-n-[6,12,18-trihydroxy-14-(1-hydroxyethyl)-2,8,17-triisopropyl-10,16,20,22,26-pentamethyl-5,11,23-tris(2-methylpropyl)-3,9,15,21,24,28-hexaoxo-1,4,25-trioxa-7,10,13,16,19,22-hexaazacyclooctacosa-6,12,18-trien-27-yl]pentanimidic acid

3-methyl-2-(methylamino)-n-[6,12,18-trihydroxy-14-(1-hydroxyethyl)-2,8,17-triisopropyl-10,16,20,22,26-pentamethyl-5,11,23-tris(2-methylpropyl)-3,9,15,21,24,28-hexaoxo-1,4,25-trioxa-7,10,13,16,19,22-hexaazacyclooctacosa-6,12,18-trien-27-yl]pentanimidic acid

C54H96N8O14 (1080.7046)


   

(3r,3ar,4r,5s,7as)-7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl (2e)-3-[(2r,3r)-3-methyloxiran-2-yl]prop-2-enoate

(3r,3ar,4r,5s,7as)-7a-hydroxy-3-(1-hydroxy-4-methylpent-3-en-1-yl)-4-methoxy-3-methyl-hexahydro-2-benzofuran-5-yl (2e)-3-[(2r,3r)-3-methyloxiran-2-yl]prop-2-enoate

C22H34O7 (410.2304)


   

(1r)-1-heptyl-6,8-dihydroxy-4-[(4r)-4,7,9,10-tetrahydroxy-3-methylidene-1-oxo-4h-naphtho[2,3-c]pyran-6-yl]-1h-isochromene-3,7-dione

(1r)-1-heptyl-6,8-dihydroxy-4-[(4r)-4,7,9,10-tetrahydroxy-3-methylidene-1-oxo-4h-naphtho[2,3-c]pyran-6-yl]-1h-isochromene-3,7-dione

C30H28O11 (564.1632)


   

16-benzyl-5,7,14-trimethyl-13-methylidene-17-azatetracyclo[9.7.0.0¹,¹⁵.0³,¹⁰]octadeca-4,17-diene-2,9,12,18-tetrol

16-benzyl-5,7,14-trimethyl-13-methylidene-17-azatetracyclo[9.7.0.0¹,¹⁵.0³,¹⁰]octadeca-4,17-diene-2,9,12,18-tetrol

C28H37NO4 (451.2722)


   

methyl 11,16,18,23-tetrahydroxy-7-(1-hydroxy-4-methoxy-4-oxobutyl)-20-methyl-9,14-dioxo-6-oxahexacyclo[11.10.2.0¹,¹⁵.0³,¹².0⁵,¹⁰.0¹⁷,²²]pentacosa-3,5(10),11,15,17,19,21,24-octaene-7-carboxylate

methyl 11,16,18,23-tetrahydroxy-7-(1-hydroxy-4-methoxy-4-oxobutyl)-20-methyl-9,14-dioxo-6-oxahexacyclo[11.10.2.0¹,¹⁵.0³,¹².0⁵,¹⁰.0¹⁷,²²]pentacosa-3,5(10),11,15,17,19,21,24-octaene-7-carboxylate

C32H30O12 (606.1737)


   

3-{hydroxy[1,3,6-trimethyl-2-(penta-1,3-dien-1-yl)-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl]methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione

3-{hydroxy[1,3,6-trimethyl-2-(penta-1,3-dien-1-yl)-4a,5,6,7,8,8a-hexahydro-2h-naphthalen-1-yl]methylidene}-5-(hydroxymethyl)-1-methylpyrrolidine-2,4-dione

C25H35NO4 (413.2566)


   

8a-hydroxy-5-[5-hydroxy-4-(oct-1-en-3-yl)-2-oxopyrrole-3-carbonyl]-4,6-dimethyl-2,3,4,4a,5,6-hexahydro-1h-naphthalene-2-carboxylic acid

8a-hydroxy-5-[5-hydroxy-4-(oct-1-en-3-yl)-2-oxopyrrole-3-carbonyl]-4,6-dimethyl-2,3,4,4a,5,6-hexahydro-1h-naphthalene-2-carboxylic acid

C26H35NO6 (457.2464)


   

(2r,3s)-2-hydroxy-4-oxo-3-phenylheptanedioic acid

(2r,3s)-2-hydroxy-4-oxo-3-phenylheptanedioic acid

C13H14O6 (266.079)


   

1-(5-benzyl-6-hydroxy-3-methylhex-3-en-1-yl)-4,7-dihydroxy-6-[(4-methyloct-2-enoyl)oxy]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

1-(5-benzyl-6-hydroxy-3-methylhex-3-en-1-yl)-4,7-dihydroxy-6-[(4-methyloct-2-enoyl)oxy]-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid

C32H42O13 (634.2625)


   

7,7a-dihydroxy-3,6,6,7b-tetramethyl-1h,2h,7h-cyclobuta[e]inden-4-one

7,7a-dihydroxy-3,6,6,7b-tetramethyl-1h,2h,7h-cyclobuta[e]inden-4-one

C15H20O3 (248.1412)


   

(1s,2r,5r,6s,7r,8r)-6,7-dihydroxy-5-methyl-2-pentyl-3,11-dioxabicyclo[6.2.1]undecan-4-one

(1s,2r,5r,6s,7r,8r)-6,7-dihydroxy-5-methyl-2-pentyl-3,11-dioxabicyclo[6.2.1]undecan-4-one

C15H26O5 (286.178)


   

(2s,3s)-n-[(2s,5s,8s,11s,14s,17s,20s,23s,26r,27s)-8-[(2s)-butan-2-yl]-6,12,18-trihydroxy-14-(hydroxymethyl)-2,17-diisopropyl-10,16,20,22,26-pentamethyl-5,11,23-tris(2-methylpropyl)-3,9,15,21,24,28-hexaoxo-1,4,25-trioxa-7,10,13,16,19,22-hexaazacyclooctacosa-6,12,18-trien-27-yl]-3-methyl-2-(methylamino)pentanimidic acid

(2s,3s)-n-[(2s,5s,8s,11s,14s,17s,20s,23s,26r,27s)-8-[(2s)-butan-2-yl]-6,12,18-trihydroxy-14-(hydroxymethyl)-2,17-diisopropyl-10,16,20,22,26-pentamethyl-5,11,23-tris(2-methylpropyl)-3,9,15,21,24,28-hexaoxo-1,4,25-trioxa-7,10,13,16,19,22-hexaazacyclooctacosa-6,12,18-trien-27-yl]-3-methyl-2-(methylamino)pentanimidic acid

C54H96N8O14 (1080.7046)


   

7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde

7-methoxy-6-methyl-1-oxo-3h-2-benzofuran-4-carbaldehyde

C11H10O4 (206.0579)


   

3-methyl-2-(n-methylacetamido)-n-[6,12,18-trihydroxy-14-(1-hydroxyethyl)-2,17-diisopropyl-10,16,20,22,26-pentamethyl-5,11,23-tris(2-methylpropyl)-3,9,15,21,24,28-hexaoxo-8-(sec-butyl)-1,4,25-trioxa-7,10,13,16,19,22-hexaazacyclooctacosa-6,12,18-trien-27-yl]pentanimidic acid

3-methyl-2-(n-methylacetamido)-n-[6,12,18-trihydroxy-14-(1-hydroxyethyl)-2,17-diisopropyl-10,16,20,22,26-pentamethyl-5,11,23-tris(2-methylpropyl)-3,9,15,21,24,28-hexaoxo-8-(sec-butyl)-1,4,25-trioxa-7,10,13,16,19,22-hexaazacyclooctacosa-6,12,18-trien-27-yl]pentanimidic acid

C57H100N8O15 (1136.7308)


   

(3r,4s,7r,10r)-4,10-dihydroxy-9,9-dimethyl-5-pentyl-2,8-dioxatricyclo[5.4.0.0¹,³]undec-5-ene-6-carbaldehyde

(3r,4s,7r,10r)-4,10-dihydroxy-9,9-dimethyl-5-pentyl-2,8-dioxatricyclo[5.4.0.0¹,³]undec-5-ene-6-carbaldehyde

C17H26O5 (310.178)


   

3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

3-benzyl-1,6,12-trihydroxy-4,10,12-trimethyl-5-methylidene-3h,3ah,4h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

C30H39NO5 (493.2828)


   

4,5-dihydroxy-1-(5-oxo-2h-furan-2-yl)hex-2-en-1-yl 2-methylbut-2-enoate

4,5-dihydroxy-1-(5-oxo-2h-furan-2-yl)hex-2-en-1-yl 2-methylbut-2-enoate

C15H20O6 (296.126)


   

heptadeca-8,9-dien-11,13-diynoic acid

heptadeca-8,9-dien-11,13-diynoic acid

C17H22O2 (258.162)


   

(4r)-3-[(1s)-1-hydroxybutyl]-2,4-dimethylcyclopent-2-en-1-one

(4r)-3-[(1s)-1-hydroxybutyl]-2,4-dimethylcyclopent-2-en-1-one

C11H18O2 (182.1307)


   

(1r,4ar,6as,8r,10ar,10bs)-1-hydroxy-1-(hydroxymethyl)-8,10b-dimethyl-4h,4ah,6ah,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-2-one

(1r,4ar,6as,8r,10ar,10bs)-1-hydroxy-1-(hydroxymethyl)-8,10b-dimethyl-4h,4ah,6ah,7h,8h,9h,10h,10ah-naphtho[2,1-c]pyran-2-one

C16H24O4 (280.1675)


   

(1r)-6-(2-hydroxyethyl)-1-methoxy-2,2,5,7-tetramethyl-1,3-dihydroinden-4-ol

(1r)-6-(2-hydroxyethyl)-1-methoxy-2,2,5,7-tetramethyl-1,3-dihydroinden-4-ol

C16H24O3 (264.1725)


   

(3ar,5ar,7s,9as,9br)-3a-hydroxy-7,9b-dimethyl-3h,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

(3ar,5ar,7s,9as,9br)-3a-hydroxy-7,9b-dimethyl-3h,5ah,6h,7h,8h,9h,9ah-naphtho[1,2-c]furan-1-one

C14H20O3 (236.1412)


   

[5'-(acetyloxy)-1,1',5,9,9'-pentahydroxy-10'a-(hydroxymethyl)-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthen]-10a-yl]methyl acetate

[5'-(acetyloxy)-1,1',5,9,9'-pentahydroxy-10'a-(hydroxymethyl)-6,6'-dimethyl-8,8'-dioxo-5h,5'h,6h,6'h,7h,7'h-[2,2'-bixanthen]-10a-yl]methyl acetate

C34H34O14 (666.1948)


   

(3r,4r,5s,6r)-4-hydroxy-6-[(1e)-3-hydroxy-3-methylpent-1-en-1-yl]-3,5-dimethyloxan-2-one

(3r,4r,5s,6r)-4-hydroxy-6-[(1e)-3-hydroxy-3-methylpent-1-en-1-yl]-3,5-dimethyloxan-2-one

C13H22O4 (242.1518)


   

methyl (2r)-7-[(4,5-dihydroxy-7-methyl-9,10-dioxoanthracen-1-yl)methyl]-5-hydroxy-4-oxo-2-[(2s)-5-oxooxolan-2-yl]-3h-1-benzopyran-2-carboxylate

methyl (2r)-7-[(4,5-dihydroxy-7-methyl-9,10-dioxoanthracen-1-yl)methyl]-5-hydroxy-4-oxo-2-[(2s)-5-oxooxolan-2-yl]-3h-1-benzopyran-2-carboxylate

C31H24O11 (572.1319)


   

(1's,2s,2's,4'r,9's,11'e,15'r)-2',20'-dihydroxy-1',3,9',13',13',18'-hexamethyl-5-oxo-8',23'-dioxaspiro[furan-2,6'-tetracyclo[13.8.0.0⁴,⁹.0¹⁷,²²]tricosane]-11',17',19',21'-tetraen-7'-ylideneacetic acid

(1's,2s,2's,4'r,9's,11'e,15'r)-2',20'-dihydroxy-1',3,9',13',13',18'-hexamethyl-5-oxo-8',23'-dioxaspiro[furan-2,6'-tetracyclo[13.8.0.0⁴,⁹.0¹⁷,²²]tricosane]-11',17',19',21'-tetraen-7'-ylideneacetic acid

C32H40O8 (552.2723)


   

(3r)-3,6,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

(3r)-3,6,8-trihydroxy-3,4-dihydro-2h-naphthalen-1-one

C10H10O4 (194.0579)


   

(3s,3ar,6s,6ar,10s,12r,15r,15ar)-3-benzyl-1,6,12-trihydroxy-4,5,10,12-tetramethyl-3h,3ah,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

(3s,3ar,6s,6ar,10s,12r,15r,15ar)-3-benzyl-1,6,12-trihydroxy-4,5,10,12-tetramethyl-3h,3ah,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindol-15-yl acetate

C30H39NO5 (493.2828)


   

(3s,3ar,4s,5s,6s,6ar,10s,12r,15r,15as)-3-benzyl-4,5,10,12-tetramethyl-3h,3ah,5h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-1,4,6,12,15-pentol

(3s,3ar,4s,5s,6s,6ar,10s,12r,15r,15as)-3-benzyl-4,5,10,12-tetramethyl-3h,3ah,5h,6h,6ah,9h,10h,11h,15h-cycloundeca[d]isoindole-1,4,6,12,15-pentol

C28H39NO5 (469.2828)


   

2-ethyl-1,6,7-trihydroxy-3-methoxy-6-methyl-7,8-dihydro-5h-anthracene-9,10-dione

2-ethyl-1,6,7-trihydroxy-3-methoxy-6-methyl-7,8-dihydro-5h-anthracene-9,10-dione

C18H20O6 (332.126)


   

(1s,4s,9s,10s,13s)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane

(1s,4s,9s,10s,13s)-5,5,9-trimethyl-14-methylidenetetracyclo[11.2.1.0¹,¹⁰.0⁴,⁹]hexadecane

C20H32 (272.2504)


   

3,8-dihydroxy-6-methoxy-3,4,5-trimethyl-4h-2-benzopyran-1-one

3,8-dihydroxy-6-methoxy-3,4,5-trimethyl-4h-2-benzopyran-1-one

C13H16O5 (252.0998)


   

5-{6,7-dihydroxy-5-methyl-4-oxo-3,11-dioxabicyclo[6.2.1]undecan-2-yl}pentyl acetate

5-{6,7-dihydroxy-5-methyl-4-oxo-3,11-dioxabicyclo[6.2.1]undecan-2-yl}pentyl acetate

C17H28O7 (344.1835)


   

(4r)-6-[(1r)-1-heptyl-6,7,8-trihydroxy-3-oxo-1h-2-benzopyran-4-ylidene]-4,9,10-trihydroxy-3-methylidene-4h-naphtho[2,3-c]pyran-1,7-dione

(4r)-6-[(1r)-1-heptyl-6,7,8-trihydroxy-3-oxo-1h-2-benzopyran-4-ylidene]-4,9,10-trihydroxy-3-methylidene-4h-naphtho[2,3-c]pyran-1,7-dione

C30H28O11 (564.1632)


   

(3s,4s,5r,7s,9r,10s,13s,16r,17s,19r,23s,30r)-22-hydroxy-5,7,11,13,14,16-hexamethyl-2-oxa-21-azaheptacyclo[23.2.2.1³,¹⁰.0⁴,⁹.0¹²,¹⁶.0¹⁹,²³.0¹⁷,³⁰]triaconta-1(27),11,14,21,25,28-hexaene-18,20-dione

(3s,4s,5r,7s,9r,10s,13s,16r,17s,19r,23s,30r)-22-hydroxy-5,7,11,13,14,16-hexamethyl-2-oxa-21-azaheptacyclo[23.2.2.1³,¹⁰.0⁴,⁹.0¹²,¹⁶.0¹⁹,²³.0¹⁷,³⁰]triaconta-1(27),11,14,21,25,28-hexaene-18,20-dione

C34H41NO4 (527.3035)


   

4,10-dihydroxy-9,9-dimethyl-5-pentyl-2,8-dioxatricyclo[5.4.0.0¹,³]undec-5-ene-6-carbaldehyde

4,10-dihydroxy-9,9-dimethyl-5-pentyl-2,8-dioxatricyclo[5.4.0.0¹,³]undec-5-ene-6-carbaldehyde

C17H26O5 (310.178)


   

methyl 2,3,5-trihydroxytridecanoate

methyl 2,3,5-trihydroxytridecanoate

C14H28O5 (276.1937)


   

(4ar,4br,6ar,7r,10ar)-4a,6a-dimethyl-7-[(2r,5r)-4,5,6-trimethylhept-3-en-2-yl]-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione

(4ar,4br,6ar,7r,10ar)-4a,6a-dimethyl-7-[(2r,5r)-4,5,6-trimethylhept-3-en-2-yl]-3h,4h,4bh,5h,6h,7h,8h,9h,11h-indeno[1,7a-a]naphthalene-2,10,12-trione

C29H42O3 (438.3134)


   

8-hydroxy-4-methoxy-7-propyl-5h,7h,8h-pyrano[3,2-c]pyran-2-one

8-hydroxy-4-methoxy-7-propyl-5h,7h,8h-pyrano[3,2-c]pyran-2-one

C12H16O5 (240.0998)