NCBI Taxonomy: 35718

Hypericin

C30H16O8 (504.0845)

Hypericin is found in alcoholic beverages. Hypericin is widespread in Hypericum species especially Hypericum perforatum (St Johns Wort) Hypericin is a red-coloured anthraquinone-derivative, which, together with hyperforin, is one of the principal active constituents of Hypericum (Saint Johns wort). Hypericin is believed to act as an antibiotic and non-specific kinase inhibitor. Hypericin may inhibit the action of the enzyme dopamine -hydroxylase, leading to increased dopamine levels, although thus possibly decreasing norepinephrine and epinephrine D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents Widespread in Hypericum subspecies especies Hypericum perforatum (St Johns Wort) D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D011838 - Radiation-Sensitizing Agents D000970 - Antineoplastic Agents C1907 - Drug, Natural Product D004791 - Enzyme Inhibitors Hypericin is a carbopolycyclic compound. It has a role as an antidepressant. It derives from a hydride of a bisanthene. Hypericin is a natural product found in Hypericum adenotrichum, Hypericum bithynicum, and other organisms with data available. Hypericin is an anthraquinone derivative that is naturally found in the yellow flower of Hypericum perforatum (St. Johns wort) with antidepressant, potential antiviral, antineoplastic and immunostimulating activities. Hypericin appears to inhibit the neuronal uptake of serotonin, norepinephrine, dopamine, gamma-amino butyric acid (GABA) and L-glutamate, which may contribute to its antidepressant effect. Hypericin may also prevent the replication of encapsulated viruses probably due to inhibition of the assembly and shedding of virus particles in infected cells. This agent also exerts potent phototoxic effects by triggering apoptotic signaling that results in formation of reactive oxygen species. Hypericin is a naturally occurring substance found in Hyperlcurn perforatum L. Hypericin is an inhibitor of PKC (protein kinase C), MAO (monoaminoxidase), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450). Hypericin shows antitumor, antiviral, antidepressive activities, and can induce apoptosis[1][2][3]. Hypericin is a naturally occurring substance found in Hyperlcurn perforatum L. Hypericin is an inhibitor of PKC (protein kinase C), MAO (monoaminoxidase), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450). Hypericin shows antitumor, antiviral, antidepressive activities, and can induce apoptosis[1][2][3].

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.

Ergosterol

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.

Orcinol

C7H8O2 (124.0524)

Orcinol is a 5-alkylresorcinol in which the alkyl group is specified as methyl. It has a role as an Aspergillus metabolite. It is a 5-alkylresorcinol and a dihydroxytoluene. Orcinol is a natural product found in Calluna vulgaris, Rumex patientia, and other organisms with data available. A 5-alkylresorcinol in which the alkyl group is specified as methyl. D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents relative retention time with respect to 9-anthracene Carboxylic Acid is 0.272 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.266 relative retention time with respect to 9-anthracene Carboxylic Acid is 0.263 KEIO_ID O013

4-hydroxyphenylacetate

C8H8O3 (152.0473)

p-Hydroxyphenylacetic acid, also known as 4-hydroxybenzeneacetate, is classified as a member of the 1-hydroxy-2-unsubstituted benzenoids. 1-Hydroxy-2-unsubstituted benzenoids are phenols that are unsubstituted at the 2-position. p-Hydroxyphenylacetic acid is considered to be slightly soluble (in water) and acidic.  p-Hydroxyphenylacetic acid can be synthesized from acetic acid. It is also a parent compound for other transformation products, including but not limited to, methyl 2-(4-hydroxyphenyl)acetate, ixerochinolide, and lactucopicrin 15-oxalate.  p-Hydroxyphenylacetic acid can be found in numerous foods such as olives, cocoa beans, oats, and mushrooms. p-Hydroxyphenylacetic acid can be found throughout all human tissues and in all biofluids. Within a cell, p-hydroxyphenylacetic acid is primarily located in the cytoplasm and in the extracellular space. p-Hydroxyphenylacetic acid is also a microbial metabolite produced by Acinetobacter, Clostridium, Klebsiella, Pseudomonas, and Proteus. Higher levels of this metabolite are associated with an overgrowth of small intestinal bacteria from Clostridia species including C. difficile, C. stricklandii, C. lituseburense, C. subterminale, C. putrefaciens, and C. propionicum (PMID: 476929, 12173102). p-Hydroxyphenylacetic acid is detected after the consumption of whole grain. 4-hydroxyphenylacetic acid is a monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. It has a role as a plant metabolite, a fungal metabolite, a human metabolite and a mouse metabolite. It is a monocarboxylic acid and a member of phenols. It is functionally related to an acetic acid. It is a conjugate acid of a 4-hydroxyphenylacetate. 4-Hydroxyphenylacetic acid is a natural product found in Guanomyces polythrix, Forsythia suspensa, and other organisms with data available. 4-Hydroxyphenylacetic acid is a metabolite found in or produced by Saccharomyces cerevisiae. A monocarboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by a 4-hydroxyphenyl group. Constituent of sweet clover (Melilotus officinalis) and yeast Hydroxyphenylacetic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=156-38-7 (retrieved 2024-07-02) (CAS RN: 156-38-7). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

2-Aminobenzoic acid

C7H7NO2 (137.0477)

2-Aminobenzoic acid, also known as anthranilic acid or O-aminobenzoate, belongs to the class of organic compounds known as aminobenzoic acids. These are benzoic acids containing an amine group attached to the benzene moiety. Within humans, 2-aminobenzoic acid participates in a number of enzymatic reactions. In particular, 2-aminobenzoic acid and formic acid can be biosynthesized from formylanthranilic acid through its interaction with the enzyme kynurenine formamidase. In addition, 2-aminobenzoic acid and L-alanine can be biosynthesized from L-kynurenine through its interaction with the enzyme kynureninase. It is a substrate of enzyme 2-Aminobenzoic acid hydroxylase in benzoate degradation via hydroxylation pathway (KEGG). In humans, 2-aminobenzoic acid is involved in tryptophan metabolism. Outside of the human body, 2-Aminobenzoic acid has been detected, but not quantified in several different foods, such as mamey sapotes, prairie turnips, rowals, natal plums, and hyacinth beans. This could make 2-aminobenzoic acid a potential biomarker for the consumption of these foods. 2-Aminobenzoic acid is a is a tryptophan-derived uremic toxin with multidirectional properties that can affect the hemostatic system. Uremic syndrome may affect any part of the body and can cause nausea, vomiting, loss of appetite, and weight loss. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. It can also cause changes in mental status, such as confusion, reduced awareness, agitation, psychosis, seizures, and coma. 2-Aminobenzoic acid is an organic compound. It is a substrate of enzyme anthranilate hydroxylase [EC 1.14.13.35] in benzoate degradation via hydroxylation pathway (KEGG). [HMDB]. Anthranilic acid is found in many foods, some of which are butternut squash, sunflower, ginger, and hyssop. Acquisition and generation of the data is financially supported in part by CREST/JST. D002491 - Central Nervous System Agents > D000927 - Anticonvulsants CONFIDENCE standard compound; INTERNAL_ID 8844 CONFIDENCE standard compound; INTERNAL_ID 8009 CONFIDENCE standard compound; INTERNAL_ID 115 KEIO_ID A010

Emodin

C15H10O5 (270.0528)

Emodin appears as orange needles or powder. (NTP, 1992) Emodin is a trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs. It has a role as a tyrosine kinase inhibitor, an antineoplastic agent, a laxative and a plant metabolite. It is functionally related to an emodin anthrone. It is a conjugate acid of an emodin(1-). Emodin has been investigated for the treatment of Polycystic Kidney. Emodin is a natural product found in Rumex dentatus, Rhamnus davurica, and other organisms with data available. Emodin is found in dock. Emodin is present in Cascara sagrada.Emodin is a purgative resin from rhubarb, Polygonum cuspidatum, the buckthorn and Japanese Knotweed (Fallopia japonica). The term may also refer to any one of a series of principles isomeric with the emodin of rhubarb. (Wikipedia) Emodin has been shown to exhibit anti-inflammatory, signalling, antibiotic, muscle building and anti-angiogenic functions (A3049, A7853, A7854, A7855, A7857). Purgative anthraquinone found in several plants, especially RHAMNUS PURSHIANA. It was formerly used as a laxative, but is now used mainly as a tool in toxicity studies. See also: Reynoutria multiflora root (part of); Frangula purshiana Bark (part of). A trihydroxyanthraquinone that is 9,10-anthraquinone which is substituted by hydroxy groups at positions 1, 3, and 8 and by a methyl group at position 6. It is present in the roots and barks of numerous plants (particularly rhubarb and buckthorn), moulds, and lichens. It is an active ingredient of various Chinese herbs. Emodin is found in dock. Emodin is present in Cascara sagrada.Emodin is a purgative resin from rhubarb, Polygonum cuspidatum, the buckthorn and Japanese Knotweed (Fallopia japonica). The term may also refer to any one of a series of principles isomeric with the emodin of rhubarb. (Wikipedia C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor D004791 - Enzyme Inhibitors > D047428 - Protein Kinase Inhibitors D005765 - Gastrointestinal Agents > D002400 - Cathartics Present in Cascara sagrada CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8540; ORIGINAL_PRECURSOR_SCAN_NO 8539 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8561; ORIGINAL_PRECURSOR_SCAN_NO 8559 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5082; ORIGINAL_PRECURSOR_SCAN_NO 5079 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8572; ORIGINAL_PRECURSOR_SCAN_NO 8570 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5104; ORIGINAL_PRECURSOR_SCAN_NO 5099 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8558; ORIGINAL_PRECURSOR_SCAN_NO 8556 ORIGINAL_PRECURSOR_SCAN_NO 5094; CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8554; ORIGINAL_PRECURSOR_SCAN_NO 8550 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5096; ORIGINAL_PRECURSOR_SCAN_NO 5093 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 8556; ORIGINAL_PRECURSOR_SCAN_NO 8554 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5090; ORIGINAL_PRECURSOR_SCAN_NO 5089 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5085; ORIGINAL_PRECURSOR_SCAN_NO 5082 CONFIDENCE standard compound; INTERNAL_ID 999; DATASET 20200303_ENTACT_RP_MIX507; DATA_PROCESSING MERGING RMBmix ver. 0.2.7; DATA_PROCESSING PRESCREENING Shinyscreen ver. 0.8.0; ORIGINAL_ACQUISITION_NO 5097; ORIGINAL_PRECURSOR_SCAN_NO 5094 [Raw Data] CB029_Emodin_pos_50eV_CB000015.txt [Raw Data] CB029_Emodin_pos_10eV_CB000015.txt [Raw Data] CB029_Emodin_pos_20eV_CB000015.txt [Raw Data] CB029_Emodin_pos_30eV_CB000015.txt [Raw Data] CB029_Emodin_pos_40eV_CB000015.txt [Raw Data] CB029_Emodin_neg_50eV_000008.txt [Raw Data] CB029_Emodin_neg_20eV_000008.txt [Raw Data] CB029_Emodin_neg_40eV_000008.txt [Raw Data] CB029_Emodin_neg_30eV_000008.txt [Raw Data] CB029_Emodin_neg_10eV_000008.txt CONFIDENCE standard compound; ML_ID 38 Emodin (Frangula emodin), an anthraquinone derivative, is an anti-SARS-CoV compound. Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 (ACE2) interaction[1]. Emodin inhibits casein kinase-2 (CK2). Anti-inflammatory and anticancer effects[2]. Emodin is a potent selective 11β-HSD1 inhibitor with the IC50 of 186 and 86 nM for human and mouse 11β-HSD1, respectively. Emodin ameliorates metabolic disorder in diet-induced obese mice[3]. Emodin (Frangula emodin), an anthraquinone derivative, is an anti-SARS-CoV compound. Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 (ACE2) interaction[1]. Emodin inhibits casein kinase-2 (CK2). Anti-inflammatory and anticancer effects[2]. Emodin is a potent selective 11β-HSD1 inhibitor with the IC50 of 186 and 86 nM for human and mouse 11β-HSD1, respectively. Emodin ameliorates metabolic disorder in diet-induced obese mice[3].

Citrinin

C13H14O5 (250.0841)

Citrinin is a mycotoxin originally isolated from Penicillium citrinum. It has since been found to be produced by a variety of other fungi which are found or used in the production of human foods, such as grain, cheese, sake and red pigments. Citrinin has also been found in commercial red yeast rice supplements, and also in Aspergillus niveus and Aspergillus terreus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987). D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins Citrinin is a mycotoxin which causes contamination in the food and is associated with different toxic effects. Citrinin is usually found together with another nephrotoxic mycotoxin, Ochratoxin A. Citrinin is also reported to possess a broad spectrum of bioactivities, including antibacterial, antifungal, and potential anticancer and neuro-protective effects in vitro[1][2].

Sterigmatocystin

C18H12O6 (324.0634)

Sterigmatocystin is a mycotoxin of Aspergillus versicolor and Chaetomium species Sterigmatocystin is a poison of the type dermatoxin, from the fungi genus Aspergillus. It appears on crusts of cheese with mold. Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins (compare general fact sheet number 2), and consists of a xanthone nucleus attached to a bifuran structure. Sterigmatocystin is mainly produced by the fungi Aspergillus nidulans and A. versicolor. It has been reported in mouldy grain, green coffee beans and cheese although information on its occurrence in foods is limited. It appears to occur much less frequently than the aflatoxins, although analytical methods for its determination have not been as sensitive until recently, and so it is possible that small concentrations in food commodities may not always have been detected. Although it is a potent liver carcinogen similar to aflatoxin B1, current knowledge suggests that it is nowhere near as widespread in its occurrence. If this is the true situation it would be justified to consider sterigmatocystin as no more than a risk to consumers in special or unusual circumstances. Sterigmatocystin is a number of closely related compounds such o-methyl sterigmatocystin are known and some may also occur naturally. The IARC-classification of sterigmatocystin is group 2B, which means it is possibly carcinogenic to humans. In practice, the risk is quite low however, because this substance only appears on cheese crusts with mold, and because of that the chance of daily exposure is very low. Sterigmatocystin is a molded crust is best not to be consumed in whole, but after removing the crust, the cheese can still be consumed. Sterigmatocystin is a different kind of mold than that which appears on cheese itself, which can simply be removed before further consumption D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2320

aphidicolin

C20H34O4 (338.2457)

A tetracyclic diterpenoid that has an tetradecahydro-8,11a-methanocyclohepta[a]naphthalene skeleton with two hydroxymethyl substituents at positions 4 and 9, two methyl substituents at positions 4 and 11b and two hydroxy substituents at positions 3 and 9. An antibiotic with antiviral and antimitotical properties. Aphidicolin is a reversible inhibitor of eukaryotic nuclear DNA replication. D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D004791 - Enzyme Inhibitors

Myriocin

C21H39NO6 (401.2777)

An amino acid-based antibiotic derived from certain thermophilic fungi; acts as a potent inhibitor of serine palmitoyltransferase, the first step in sphingosine biosynthesis. Myriocin also possesses immunosuppressant activity. D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents D000890 - Anti-Infective Agents > D000935 - Antifungal Agents [Raw Data] CBA29_Myriocin_pos_20eV_1-3_01_1557.txt [Raw Data] CBA29_Myriocin_neg_40eV_1-3_01_1590.txt [Raw Data] CBA29_Myriocin_pos_10eV_1-3_01_1546.txt [Raw Data] CBA29_Myriocin_neg_30eV_1-3_01_1589.txt [Raw Data] CBA29_Myriocin_pos_40eV_1-3_01_1559.txt [Raw Data] CBA29_Myriocin_pos_30eV_1-3_01_1558.txt [Raw Data] CBA29_Myriocin_pos_50eV_1-3_01_1560.txt [Raw Data] CBA29_Myriocin_neg_10eV_1-3_01_1578.txt [Raw Data] CBA29_Myriocin_neg_20eV_1-3_01_1588.txt Myriocin (Thermozymocidin), a fungal metabolite could be isolated from Myriococcum albomyces, Isaria sinclairi and Mycelia sterilia, is a potent inhibitor of serine-palmitoyl-transferase (SPT) and a key enzyme in de novo synthesis of sphingolipids. Myriocin suppresses replication of both the subgenomic HCV-1b replicon and the JFH-1 strain of genotype 2a infectious HCV, with an IC50 of 3.5 μg/mL for inhibiting HCV infection[1][2][3].

2-Furoic 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].

Phenylacetaldehyde

C8H8O (120.0575)

Phenylacetaldehyde is one important oxidation-related aldehyde. Exposure to styrene gives phenylacetaldehyde as a secondary metabolite. Styrene has been implicated as reproductive toxicant, neurotoxicant, or carcinogen in vivo or in vitro. Phenylacetaldehyde could be formed by diverse thermal reactions during the cooking process together with C8 compounds is identified as a major aroma- active compound in cooked pine mushroom. Phenylacetaldehyde is readily oxidized to phenylacetic acid. Therefore will eventually be hydrolyzed and oxidized to yield phenylacetic acid that will be excreted primarily in the urine in conjugated form. (PMID: 16910727, 7818768, 15606130). Found in some essential oils, e.g. Citrus subspecies, Tagetes minuta (Mexican marigold) and in the mushroom Phallus impudicus (common stinkhorn). Flavouring ingredient COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Chrysophanol

C15H10O4 (254.0579)

Chrysophanic acid appears as golden yellow plates or brown powder. Melting point 196 °C. Slightly soluble in water. Pale yellow aqueous solutions turn red on addition of alkali. Solutions in concentrated sulfuric acid are red. (NTP, 1992) Chrysophanol is a trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity. It has a role as an antiviral agent, an anti-inflammatory agent and a plant metabolite. It is functionally related to a chrysazin. Chrysophanol is a natural product found in Rumex dentatus, Ageratina altissima, and other organisms with data available. See also: Frangula purshiana Bark (part of). A trihydroxyanthraquinone that is chrysazin with a methyl substituent at C-3. It has been isolated from Aloe vera and exhibits antiviral and anti-inflammatory activity. Constituent of Rumex, Rheum subspecies Chrysophanol is found in dock, garden rhubarb, and sorrel. Chrysophanol is found in dock. Chrysophanol is a constituent of Rumex, Rheum species D009676 - Noxae > D009153 - Mutagens Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K. Chrysophanol (Chrysophanic acid) is a natural anthraquinone, which inhibits EGF-induced phosphorylation of EGFR and suppresses activation of AKT and mTOR/p70S6K.

Patulin

C7H6O4 (154.0266)

Patulin is found in pomes. Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice Patulin is a mycotoxin produced by a variety of molds, particularly Aspergillus and Penicillium. It is commonly found in rotting apples, and the amount of patulin in apple products is generally viewed as a measure of the quality of the apples used in production. It is not a particularly potent toxin, but a number of studies have shown that it is genotoxic, which has led to some theories that it may be a carcinogen, though animal studies have remained inconclusive. Patulin is also an antibiotic. Several countries have instituted patulin restrictions in apple products. The World Health Organization recommends a maximum concentration of 50 µg/L in apple juice Mycotoxin, found as a contaminant of foods, e.g. apple juice. Sometimes detd. in apple juice D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins D009676 - Noxae > D009153 - Mutagens Patulin (Terinin) is a mycotoxin produced by fungi including the Aspergillus, Penicillium, and Byssochlamys species, is suspected to be clastogenic, mutagenic, teratogenic and cytotoxic. Patulin induces autophagy-dependent apoptosis through lysosomal-mitochondrial axis, and causes DNA damage[1][2][3][4].

Geosmin

C12H22O (182.1671)

Geosmin is found in corn. Implicated in off-flavour of shellfish, freshwater fish, drinking water and some vegetables.Geosmin, which literally translates to "earth smell", is an organic compound with a distinct earthy flavour and aroma, and is responsible for the earthy taste of beets and a contributor to the strong scent that occurs in the air when rain falls after a dry spell of weather (petrichor) or when soil is disturbed. The human nose is extremely sensitive to geosmin and is able to detect it at concentrations as low as 5 parts per trillion. Implicated in off-flavour of shellfish, freshwater fish, drinking water and some vegetables

O-Methylsterigmatocystin

C19H14O6 (338.079)

O-Methylsterigmatocystin is a mycotoxin of Aspergillus flavu D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins

Citreorosein

C15H10O6 (286.0477)

Citreorosein is found in green vegetables. Citreorosein is found in roots of Polygonum cuspidatum (Japanese knotweed Found in roots of Polygonum cuspidatum (Japanese knotweed)

Mollicellin C

C22H20O8 (412.1158)

A member of the class of depsidones that is 11H-dibenzo[b,e][1,4]dioxepine substituted by hydroxy groups at positions 3 and 9, a methoxy group at position 8, methyl groups at positions 1 and 6, a 3-methylbut-2-enoyl group at position 7, an oxo group at position 11 and a formyl group at position 4. Isolated from Chaetomium brasiliense, it exhibits antimalarial and cytotoxic activities.

Sumiki's acid

C6H6O4 (142.0266)

Sumikis acid is a naturally occurring human metabolite (PMID:949837). Sumikis acid was first identified in the urine of a leukemic patient who was excreting an abnormal amount of its glycine derivative (PMID:5043270). Sumikis acid was found to be excreted by normal subjects after a phenylalanine loading, while heterozygotes for phenylketonuria dont excrete it (instead, they excrete 2-hydroxybenzeneacetic acid) (PMID:4708049). Patients receiving furan-containing sugar solutions i.v. convert 50\\\\% of the 5-hydroxymethyl-2-furfural into Sumikis acid (PMID:4202014). Sumikis acid has been found to be a byproduct of the fungus Aspergillus and probably other species of fungi and yeast as well. Sumikis acid is a naturally occurring human metabolite. (PMID: 949837) Sumikis acid was first identified in the urine of a leukemic patient who was excreting an abnormal amount of its glycine derivative. (PMID: 5043270) 5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally. 5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally.

Penitrem C

C37H44ClNO4 (601.2959)

Ergosterol peroxide

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.

Brevianamide B

C21H23N3O3 (365.1739)

Brevianamide A is a mycotoxin from Penicillium brevi-compactum and some other Penicillium specie

Mollicellin C

C22H20O8 (412.1158)

Mollicellin C is produced by Chaetomium species and mutagenic mycotoxin. Production by Chaetomium subspecies and mutagenic mycotoxin.

Mollicellin B

C21H18O7 (382.1052)

Mollicellin B is produced by Chaetomium species and mutagenic mycotoxin. Production by Chaetomium subspecies and mutagenic mycotoxin.

Mollicellin E

C22H19ClO8 (446.0768)

Mollicellin E is produced by Chaetomium species and mutagenic mycotoxin. Production by Chaetomium subspecies and mutagenic mycotoxin.

Mollicellin H

C21H20O6 (368.126)

Mollicellin H is produced by Chaetomium species and mutagenic mycotoxin. Production by Chaetomium subspecies and mutagenic mycotoxin.

Mollicellin D

C21H21ClO6 (404.1027)

Mollicellin D is produced by Chaetomium species and mycotoxin. Production by Chaetomium subspecies and mycotoxin.

Mollicellin I

C21H22O6 (370.1416)

Mollicellin J

C21H19ClO6 (402.087)

Eugenitin

C12H12O4 (220.0736)

From Eugenia caryophyllata (clove). Eugenitin is found in herbs and spices and cloves. Eugenitin is found in cloves. Eugenitin is from Eugenia caryophyllata (clove

Cladosporin

C16H20O5 (292.1311)

D004791 - Enzyme Inhibitors

radicicol

C18H17ClO6 (364.0714)

D000890 - Anti-Infective Agents > D000977 - Antiparasitic Agents > D000981 - Antiprotozoal Agents D000890 - Anti-Infective Agents > D000935 - Antifungal Agents D004791 - Enzyme Inhibitors An antifungal macrolactone antibiotic, obtained from Diheterospora chlamydosporia and Chaetomium chiversii that inhibits protein tyrosine kinase and heat shock protein 90 (Hsp90). C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor > C129824 - Antineoplastic Protein Inhibitor C254 - Anti-Infective Agent > C514 - Antifungal Agent

Alternariol monomethyl ether

C15H12O5 (272.0685)

Chetomin

C31H30N6O6S4 (710.111)

An organic heteropentacyclic compound of the class of epipolythiodioxopiperazine. Isolated from Chaetomium globosum and Farrowia seminuda, it exhibits immunosuppressive activity.

Botryolide E

C10H14O5 (214.0841)

Botryolide D

C10H16O5 (216.0998)

Chaetocin

C30H28N6O6S4 (696.0953)

Chaetopyranin

C19H24O4 (316.1675)

A chromenol that is 3,4-dihydro-2H-chromene substituted by a hydroxy group at position 6, a 3-hydroxybut-1-en-1-yl at position 2, a formyl group at position 5 and a prenyl group at position 7. Isolated from Chaetomium globosum, it exhibits radical scavenging and cytotoxic activity towards several tumour cell lines.

EI-1941-3

C12H16O5 (240.0998)

Chaetoxanthone B

C20H18O6 (354.1103)

A bridged organic heteropentacyclic compound that is 3,4,5,6-tetrahydro-2H,8H-2,6-epoxyoxocino[3,2-b]xanthen-8-one substituted by a hydroxy group at position 7, a methoxy group at position 9 and a methyl group at position 2. It is isolated from the marine derived fungus Chaetomium and has antiprotozoal activity.

Thielavin J

C29H30O10 (538.1839)

Botryolide A

C10H14O5 (214.0841)

Orsellic 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].

4-Hydroxyphenylacetic acid

C8H8O3 (152.0473)

4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1]. 4-hydroxyphenylacetic acid, a major microbiota-derived metabolite of polyphenols, is involved in the antioxidative action. 4-hydroxyphenylacetic acid induces expression of Nrf2[1].

chaetoxanthone A

C20H18O7 (370.1052)

A bridged organic heteropentacyclic compund that is 3,4,5,6-tetrahydro-2H,8H-2,6-epoxyoxocino[3,2-b]xanthen-8-one substituted by hydroxy groups at positions 4 and 7, a methoxy group at position 9 and a methyl group at position 2 (the 2S,4R,6S stereoisomer). It is isolated from the marine derived fungus Chaetomium and has antiprotozoal activity.

chaetoxanthone C

C20H19ClO6 (390.087)

A member of the class xanthones that is 9H-xanthen-9-one substituted by a chloro group at position 4, hydroxy groups at positions 1 and 3, a methoxy group at position 8 and a (2R,6R)-6-methyltetrahydropyran-2-yl group at position 2. It is isolated from the marine derived fungus Chaetomium and has antiprotozoal activity.

physcion

C16H12O5 (284.0685)

Physcion, also known as emodin monomethyl ether or parienin, is a member of the class of compounds known as anthraquinones. Anthraquinones are organic compounds containing either anthracene-9,10-quinone, 1,4-anthraquinone, or 1,2-anthraquinone. Physcion is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). Physcion can be synthesized from 2-methylanthraquinone. Physcion can also be synthesized into torososide B and physcion 8-gentiobioside. Physcion can be found in common sage, garden rhubarb, and sorrel, which makes physcion a potential biomarker for the consumption of these food products. Physcion has also been shown to protect lichens against UV-B light, at high altitudes in Alpine regions. The UV-B light stimulates production of parietin and the parietin protects the lichens from damage. Lichens in arctic regions such as Svarlbard retain this capability though they do not encounter damaging levels of UV-B, a capability that could help protect the lichens in case of Ozone layer thinning .

Erythroglaucin

C16H12O6 (300.0634)

A trihydroxyanthraquinone that is anthracene-9,10-dione substituted by hydroxy groups at positions 1, 4 and 5, a methoxy group at position 7 and a methyl group at position 2. It has been isolated from Chaetomium globosum and other fungal species.

Chaetochromin

C30H26O10 (546.1526)

Ergosterol peroxide

C28H44O3 (428.329)

Chaetoviridin D

C23H29ClO8 (468.1551)

globosuxanthone B

C16H16O8 (336.0845)

A member of the class of xanthones that is methyl-9-oxo-2,3,4,9-tetrahydro-1H-xanthene-1-carboxylate substituted by hydroxy groups at positions 1, 2 and 8 and a methoxy group at position 3 (the 1R,2R,3S stereoisomer). It has been isolated from Chaetomium globosum.

mollicellin L

C22H20O7 (396.1209)

A member of the class of depsidones that is 11H-dibenzo[b,e][1,4]dioxepine substituted by a hydroxy group at position 3, a methoxy group at position 7, methyl groups at positions 1 and 9, a 3-methylbut-2-enoyl group at position 8, a formyl group at position 4 and an oxo group at position 11. Isolated from Chaetomium brasiliense, it exhibits antimalarial and cytotoxic activities.

globosuxanthone D

C14H8O5 (256.0372)

A member of the class of xanthones that is 9H-xanthene substituted by a hydroxy group at position 8, an oxo group at position 9 and a carboxy group at position 1. It has been isolated from Chaetomium globosum.

chaetomugilin D

C23H27ClO6 (434.1496)

An azaphilone isolated from Chaetomium globosum and has been shown to exhibit inhibitory activity against the brine shrimp (Artemia salina) and Mucor miehei.

Aureonitol

C13H18O2 (206.1307)

Acremine D

C12H14O3 (206.0943)

Chaetoviridin C

C23H27ClO6 (434.1496)

An azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a 3-hydroxy-2-methylbutanoyl group at position 9, a methyl group at position 6a and a 3-methylpent-1-en-1yl group at position 3. It has been isolated from Chaetomium globosum.

globosumone A

C13H14O5 (250.0841)

A benzoate ester obtained by the formal condensation of o-orsellinic acid with (3E)-1-hydroxypent-3-en-2-one. Isolated from Chaetomium globosum, it exhibits cytotoxic activity towards cancer cell lines.

methyl 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate

C16H12O5 (284.0685)

A member of the class of xanthones that is 9H-xanthene substituted by a hydroxy group at position 8. a methyl group at position 6, an oxo group at position 9 and a methoxy carbonyl at position 1. It has been isolated from the fungus Aspergillus sydowii.

Mollicellin G

C21H20O6 (368.126)

Mollicellin K

C21H18O7 (382.1052)

A member of the class of depsidones that is 11H-dibenzo[b,e][1,4]dioxepine substituted by hydroxy groups at positions 3 and 7, methyl groups at positions 1 and 9, a 3-methylbut-2-enoyl group at position 8, a formyl group at position 4 and an oxo group at position 11. Isolated from Chaetomium brasiliense, it exhibits antimalarial, antimycobacterial and cytotoxic activities.

Amidepsine D

C26H24O10 (496.1369)

5-O-Methylsclerone

C11H12O3 (192.0786)

chaetoviridin E

C23H23ClO5 (414.1234)

An azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a methyl group at position 6a, a 2-methylbut-2-enoyl group at position 9 and a 3-methylpent-1-en-1-yl group at position 3. It has been isolated from Chaetomium globosum.

3,4,5-trihydroxypentan-2-yl 2,4-dihydroxy-6-methylbenzoate

C13H18O7 (286.1052)

Oosporein

C14H10O8 (306.0376)

Globosuxanthone C

C14H10O5 (258.0528)

A member of the class of xanthones that is 9H-xanthen-9-one substituted by hydroxy group at positions 1 and 8 and a methoxy group at position 2. It has been isolated from Chaetomium globosum.( Compound class : xanthenone)

Rheoemodin

C14H8O6 (272.0321)

Isotetrahydroauroglaucin

C19H26O3 (302.1882)

A member of the class of benzaldehydes that is benzaldehyde substituted by hydroxy groups at positions 3 and 6, a prenyl group at position 5 and a a hept-5-en-1-yl at position 2. Isolated from Chaetomium globosum and other fungal species, it exhibits radical scavenging activities.

globosuxanthone A

C15H12O7 (304.0583)

A member of the class of xanthones that is methyl 9-oxo-2,9-dihydro-1H-xanthene-1-carboxylate substituted by hydroxy groups at positions 1, 2 and 8 (the 1R,2R stereoisomer). Isolated from Chaetomium globosum, it exhibits cytotoxicity towards human tumour cell lines.

Hypericin

C30H16O8 (504.0845)

Hypericin is a carbopolycyclic compound. It has a role as an antidepressant. It derives from a hydride of a bisanthene. Hypericin is a natural product found in Hypericum adenotrichum, Hypericum bithynicum, and other organisms with data available. Hypericin is an anthraquinone derivative that is naturally found in the yellow flower of Hypericum perforatum (St. Johns wort) with antidepressant, potential antiviral, antineoplastic and immunostimulating activities. Hypericin appears to inhibit the neuronal uptake of serotonin, norepinephrine, dopamine, gamma-amino butyric acid (GABA) and L-glutamate, which may contribute to its antidepressant effect. Hypericin may also prevent the replication of encapsulated viruses probably due to inhibition of the assembly and shedding of virus particles in infected cells. This agent also exerts potent phototoxic effects by triggering apoptotic signaling that results in formation of reactive oxygen species. D002491 - Central Nervous System Agents > D011619 - Psychotropic Drugs > D000928 - Antidepressive Agents D007155 - Immunologic Factors > D007166 - Immunosuppressive Agents C274 - Antineoplastic Agent > C1931 - Antineoplastic Plant Product D000890 - Anti-Infective Agents > D000998 - Antiviral Agents D011838 - Radiation-Sensitizing Agents D000970 - Antineoplastic Agents C1907 - Drug, Natural Product D004791 - Enzyme Inhibitors Hypericin is a naturally occurring substance found in Hyperlcurn perforatum L. Hypericin is an inhibitor of PKC (protein kinase C), MAO (monoaminoxidase), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450). Hypericin shows antitumor, antiviral, antidepressive activities, and can induce apoptosis[1][2][3]. Hypericin is a naturally occurring substance found in Hyperlcurn perforatum L. Hypericin is an inhibitor of PKC (protein kinase C), MAO (monoaminoxidase), dopamine-beta-hydroxylase, reverse transcriptase, telomerase and CYP (cytochrome P450). Hypericin shows antitumor, antiviral, antidepressive activities, and can induce apoptosis[1][2][3].

mollicellin N

C21H18O8 (398.1002)

A member of the class of depsidones that is 3,4-dihydro-2H,11H-chromeno[6,7-b][1,4]benzodioxepine substituted by hydroxy groups at positions 8 and 13, methyl groups at positions 2, 2, 5 and 10, oxo groups at positions 4 and 11 and a formyl group at position 7. Isolated from Chaetomium brasiliense, it exhibits cytotoxic activity.

2-hydroxyvertixanthone

C15H10O6 (286.0477)

A member of the class of xanthones that is methyl 9H-xanthene-1-carboxylate substituted by hydroxy groups at positions 2 and 8 and an oxo group at position 9. It has been isolated from Chaetomium globosum.

Sterigmatocystin

C18H12O6 (324.0634)

An organic heteropentacyclic compound whose skeleton comprises a xanthene ring system ortho-fused to a dihydrofuranofuran moiety. The parent of the class of sterigmatocystins. D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE Reference Standard (Level 1)

Ergosterol

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.

Citrinin

C13H14O5 (250.0841)

CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 11 D000890 - Anti-Infective Agents > D000900 - Anti-Bacterial Agents D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE Citrinin is a mycotoxin which causes contamination in the food and is associated with different toxic effects. Citrinin is usually found together with another nephrotoxic mycotoxin, Ochratoxin A. Citrinin is also reported to possess a broad spectrum of bioactivities, including antibacterial, antifungal, and potential anticancer and neuro-protective effects in vitro[1][2].

Emodin

C15H10O5 (270.0528)

C471 - Enzyme Inhibitor > C1404 - Protein Kinase Inhibitor > C1967 - Tyrosine Kinase Inhibitor D004791 - Enzyme Inhibitors > D047428 - Protein Kinase Inhibitors D005765 - Gastrointestinal Agents > D002400 - Cathartics CONFIDENCE isolated standard relative retention time with respect to 9-anthracene Carboxylic Acid is 1.288 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.291 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.286 relative retention time with respect to 9-anthracene Carboxylic Acid is 1.293 Emodin (Frangula emodin), an anthraquinone derivative, is an anti-SARS-CoV compound. Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 (ACE2) interaction[1]. Emodin inhibits casein kinase-2 (CK2). Anti-inflammatory and anticancer effects[2]. Emodin is a potent selective 11β-HSD1 inhibitor with the IC50 of 186 and 86 nM for human and mouse 11β-HSD1, respectively. Emodin ameliorates metabolic disorder in diet-induced obese mice[3]. Emodin (Frangula emodin), an anthraquinone derivative, is an anti-SARS-CoV compound. Emodin blocks the SARS coronavirus spike protein and angiotensin-converting enzyme 2 (ACE2) interaction[1]. Emodin inhibits casein kinase-2 (CK2). Anti-inflammatory and anticancer effects[2]. Emodin is a potent selective 11β-HSD1 inhibitor with the IC50 of 186 and 86 nM for human and mouse 11β-HSD1, respectively. Emodin ameliorates metabolic disorder in diet-induced obese mice[3].

4-hydroxybenzoate

C7H6O3 (138.0317)

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

1,3-dihydroxy-6-(hydroxymethyl)-8-methoxyanthracene-9,10-dione

C16H12O6 (300.0634)

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.

Helvolic acid

C33H44O8 (568.3036)

A steroid C-21 acid having a 29-nordammarane skeleton substituted with an acetoxy group at C-16 and oxo groups at C-3 and -7, with double bonds at C-1, -17(20) and -24.

2-FUROIC ACID

C5H4O3 (112.016)

A furoic acid having the carboxylic acid group located at position 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]. 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].

phenylacetaldehyde

C8H8O (120.0575)

An aldehyde that consists of acetaldehyde bearing a methyl substituent; the parent member of the phenylacetaldehyde class of compounds. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

Danthron

C14H8O4 (240.0423)

A - Alimentary tract and metabolism > A06 - Drugs for constipation > A06A - Drugs for constipation > A06AB - Contact laxatives D005765 - Gastrointestinal Agents > D002400 - Cathartics D009676 - Noxae > D009153 - Mutagens Danthron is a natural product extracted from the traditional Chinese medicine Salvia miltiorrhiza Bunge. Danthron functions in regulating glucose and lipid metabolism by activating AMPK. Danthron is a natural product extracted from the traditional Chinese medicine Salvia miltiorrhiza Bunge. Danthron functions in regulating glucose and lipid metabolism by activating AMPK. Danthron is a natural product extracted from the traditional Chinese medicine Salvia miltiorrhiza Bunge. Danthron functions in regulating glucose and lipid metabolism by activating AMPK.

patulin

C7H6O4 (154.0266)

D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE standard compound; INTERNAL_ID 5971 D009676 - Noxae > D009153 - Mutagens CONFIDENCE Reference Standard (Level 1) Patulin (Terinin) is a mycotoxin produced by fungi including the Aspergillus, Penicillium, and Byssochlamys species, is suspected to be clastogenic, mutagenic, teratogenic and cytotoxic. Patulin induces autophagy-dependent apoptosis through lysosomal-mitochondrial axis, and causes DNA damage[1][2][3][4].

orsellinic acid

C8H8O4 (168.0423)

Chaetoviridin A

C23H25ClO6 (432.134)

An azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a 3-hydroxy-2-methylbutanoyl group at position 9, a methyl group at position 6a and a 3-methylpent-1-en-1yl group at position 3. Isolated from Chaetomium globosum, it exhibits natifungal activity against plant pathogenic fungi. CONFIDENCE isolated standard

2-aminobenzoic acid

C7H7NO2 (137.0477)

MS2 deconvoluted using MS2Dec from all ion fragmentation data, MetaboLights identifier MTBLS1040; RWZYAGGXGHYGMB-UHFFFAOYSA-N_STSL_0017_Anthranilic Acid_8000fmol_180410_S2_LC02_MS02_91; 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.

eugenitin

C12H12O4 (220.0736)

A natural product found in Cyperus teneriffae.

Citreorosein

C15H10O6 (286.0477)

5-Hydroxymethyl-2-furancarboxylic acid

C6H6O4 (142.0266)

5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally. 5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally.

Sclerotiorin

C21H23ClO5 (390.1234)

Brevianamide B

C21H23N3O3 (365.1739)

mollicellin B

C21H18O7 (382.1052)

A member of the class of depsidones that is 3,4-dihydro-2H,7H-chromeno[7,6-b][1,4]benzodioxepine substituted by a hydroxy group at position 10, methyl groups at positions 2, 2, 5 and 8, a formyl group at position 11 and oxo groups at positions 4 and 7. Isolated from Chaetomium brasiliense it exhibits antimalarial and cytotoxic activities.

Mollicellin E

C22H19ClO8 (446.0768)

A member of the class of depsidones that is 11H-dibenzo[b,e][1,4]dioxepine substituted by a chloro group at position 2, hydroxy groups at positions 3 and 9, a methoxy group at position 8, methyl groups at positions 1 and 6, a 3-methylbut-2-enoyl group at position 7, an oxo group at position 11 and a formyl group at position 4. Isolated from Chaetomium brasiliense, it exhibits antimalarial and cytotoxic activities.

Mollicellin D

C21H21ClO6 (404.1027)

mollicellin H

C21H20O6 (368.126)

A member of the class of depsidones that is 11H-dibenzo[b,e][1,4]dioxepine substituted by hydroxy groups at position 3 and 7, methyl group at positions 1 and 9, a prenyl group at position 8, an oxo group at position 11 and a formyl group at position 4. Isolated from Chaetomium brasiliense it exhibits cytotoxic activity.

Chaetominine

C22H18N4O4 (402.1328)

An organic heterotetracyclic compound that consists of 4,5,5a,9c-tetrahydro-3H-2a,9b-diazacyclopenta[jk]fluorene-1,3(2H)-dione substituted by a hydroxy group at position 5, a methyl group at position 2 and a 4-oxoquinazolin-3(4H)-yl group at position 4 (the 2S,4R,5aS,9cS stereoisomer). It is a cytotoxic alkaloid isolated from the endophytic fungus Chaetomium.

Heminigerone

C16H14O5 (286.0841)

Ergosteryl palmitate

C44H74O2 (634.5689)

A ergosteryl ester obtained by formal condensation of the 3-hydroxy group of ergosterol with the carboxy group of hexadecanoic (palmitic) acid. A natural product found in Chaetomium globosum and Chaetomium longirostre.

Rotiorinol A

C23H26O5 (382.178)

An azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, a hydroxy group at position 9, a 3,5-dimethylhepta-1,3-dien-1-yl group at position 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity.

Rotiorinol C

C23H26O6 (398.1729)

An azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, a hydroxy group at position 9, a 7-hydroxy-3,5-dimethylhepta-1,3-dien-1-yl group at position 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity.

(-)-Rotiorin

C23H24O5 (380.1624)

An azaphilone that is 9,9a-dihydro-2H-furo[3,2-g]isochromen-2-one substituted by an acetyl group at position 3, an oxo group at position 9, a 3,5-dimethylhepta-1,3-dien-1-yl group at position 6 and a methyl group at position 9a. It has been isolated from Chaetomium cupreum and exhibits antifungal activity.

epi-isochromophilone II

C22H27ClO4 (390.1598)

An azaphilone that is 7,8-dihydro-6H-isochromen-6-one substituted by a chloro group at position 5, a 3,5-dimethylhepta-1,3-dien-1-yl group at position 3, a hydroxy group at position 7, a methyl group at position 7 and a 2-oxopropyl group at position 8. Isolated from Chaetomium cupreum, it exhibits antifungal activity.

Rubrorotiorin

C23H23ClO5 (414.1234)

An azaphilone that is 6,6a-dihydro-8H-furo[2,3-h]isochromen-6,8(6aH)-dione substituted by an acetyl group at position 9, a chloro group a position 5, a 3,5-dimethylhepta-1,3-dien-1-yl group at position 3 and a methyl group at position 6a. Isolated from Chaetomium cupreum, it exhibits antifungal activity.

chaetomugilin A

C23H27ClO7 (450.1445)

An azaphilone isolated from Chaetomium globosum and has been shown to exhibit inhibitory activity against the brine shrimp (Artemia salina) and Mucor miehei.

Sumikis acid

C6H6O4 (142.0266)

5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally. 5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally.

furoic acid

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].

Geosmin

C12H22O (182.1671)

Chaetoviridin H

C23H26O6 (398.1729)

An azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a 3-hydroxy-2-methylbutanoyl group at position 9, a methyl group at position 6a and a 3-methylpent-1-en-1yl group at position 3. It has been isolated from Chaetomium globosum.

Chaetoviridin I

C23H27ClO8 (466.1394)

An azaphilone found in Chaetomium globosum.

longirostrerone C

C32H38O6 (518.2668)

An azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a 6-methyl-2-oxocyclohex-3-en-1-yl group at position 3, a methyl group at position 6a and a 4,6,8-trimethyldeca-2,4-dienoyl group at position 9. Isolated from Chaetomium longirostre, it exhibits cytotoxic and antimalarial activities.

longirostrerone D

C32H38O7 (534.2617)

A natural product found in Chaetomium longirostre. An azaphilone that is 6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a 4-hydroxy-2-methyl-6-oxocyclohexyl group at position 3, a methyl group at position 6a, and a 4,6,8-trimethyldeca-2,4-dienoyl group at position 9. Isolated from Chaetomium longirostre, it exhibits cytotoxic activities.

Chaetoviridin G

C23H25ClO5 (416.139)

An azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a chloro group at position 5, a methyl group at position 6a, a 2-methylbut-2-enoyl group at position 9 and a 3-methylpent-1-en-1-yl group at position 3. It has been isolated from Chaetomium globosum.

Longirostrerone A

C32H40O7 (536.2774)

An azaphilone that is 9,9a-dihydro-6H-furo[2,3-h]isochromene-6,8(6aH)-dione substituted by a 4-hydroxy-2-methyl-6-oxocyclohexyl group at position 3, a methyl group at position 6a and a 4,6,8-trimethyldeca-2,4-dienoyl group at position 9. Isolated from Chaetomium longirostre, it exhibits cytotoxic and antimalarial activities.

Longirostrerone B

C31H42O6 (510.2981)

An azaphilone that is 7,8-dihydro-6H-isochromen-6-one substituted by a hydroxy group at position 7, a 4-hydroxy-2-methyl-6-oxocyclohexyl group at position 3, a methyl group at position 7 and a 5,7,9-trimethyl-2-oxoundeca-3,5-dien-1-yl group at position 8. Isolated from Chaetomium longirostre, it exhibits cytotoxic and antimalarial activities.

5-hydroxy-6-(3-methylbut-2-en-1-yl)-2-[(1E)-pent-1-en-1-yl]-1-benzofuran-4-carbaldehyde

C19H22O3 (298.1569)

globosumone B

C13H16O6 (268.0947)

A benzoate ester obtained by the formal condensation of o-orsellinic acid with (4S)-1,4-dihydroxypentan-2-one. Isolated from Chaetomium globosum, it exhibits cytotoxic activity towards cancer cell lines.

globosumone C

C13H16O7 (284.0896)

A benzoate ester obtained by the formal condensation of o-orsellinic acid with (3S,4S)-1,3,4-trihydroxypentan-2-one. It has been isolated from Chaetomium globosum.

O-Methylsterigmatocystin

C19H14O6 (338.079)

D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins

Antimycin

C13H14O5 (250.0841)

methyl 2-(4-hydroxyphenyl)acetate

C9H10O3 (166.063)

A methyl ester resulting from the formal condensation of the carboxy group of 4-hydroxyphenylacetic acid with methanol. It has been isolated from Penicillium chrysogenum.

Mollicellin J

C21H19ClO6 (402.087)

A member of the class of depsidones that is 11H-dibenzo[b,e][1,4]dioxepine substituted by a chloro group at position 2, hydroxy groups at position 3 and 7, methyl group at positions 1 and 9, a prenyl group at position 8, an oxo group at position 11 and a formyl group at position 4. Isolated from Chaetomium brasiliense it exhibits cytotoxic activity.

chaetochromin C

C29H24O10 (532.1369)

A biaryl that is 2,2,3,3-tetrahydro-4H,4H-9,9-bibenzo[g]chromene-4,4-dione substituted by hydroxy groups at positions 5, 5, 6, 6, 8 and 8 and methyl groups at positions 2, 2 and 3 (the 2R,3R stereoisomer). It has been isolated from Chaetomium gracile.

5-Hydroxymethyl-2-furoic acid

C6H6O4 (142.0266)

A member of the class of furoic acids that is 2-furoic acid substituted at position 5 by a hydroxymethyl group. 5-(Hydroxymethyl)-2-furancarboxylic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=6338-41-6 (retrieved 2024-07-16) (CAS RN: 6338-41-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). 5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally. 5-Hydroxymethyl-2-furancarboxylic acid is the main metabolite of 5-hydroxymethyl-2-furfural (HMF) in the body and eliminated renally.

5,6,8-trihydroxy-2,3-dimethyl-9-{5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl}benzo[g]chromen-4-one

C30H24O10 (544.1369)

(3r)-6,8-dihydroxy-3-{[(2r,5r,6s)-5-hydroxy-6-methyloxan-2-yl]methyl}-3,4-dihydro-2-benzopyran-1-one

C16H20O6 (308.126)

(6s,8as,10s)-10-hydroxy-6,9,9,12b-tetramethyl-2-[(4e)-3-oxohex-4-en-2-yl]-5,6,7,8,8a,10,11,12-octahydro-oxatetraphene-1,4-dione

C27H36O5 (440.2563)

(1s)-1-[(2s,3ar,6r,6as)-6-(hydroxymethyl)-hexahydro-2h-cyclopenta[b]furan-2-yl]propan-1-ol

C11H20O3 (200.1412)

(1s,10s,12r,13r,14r,17r)-12-hydroxy-5-[(1e,3r,4r)-4-hydroxy-3-methylpent-1-en-1-yl]-10,13,14-trimethyl-4,11,15-trioxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁷]heptadeca-2,5,7-triene-9,16-dione

C23H28O7 (416.1835)

6-chloro-5,12-dihydroxy-7,15,15,19-tetramethyl-9,17-dioxo-2,10,14-trioxatetracyclo[9.8.0.0³,⁸.0¹³,¹⁸]nonadeca-1(19),3,5,7,11,13(18)-hexaene-4-carbaldehyde

C21H17ClO8 (432.0612)

3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,8,14,16-tetramethyl-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,7,11,18-pentaen-17-one

C32H37N3O3 (511.2835)

(4r,6s,8s,11e)-16-chloro-17,19-dihydroxy-4-methyl-3,7-dioxatricyclo[13.4.0.0⁶,⁸]nonadeca-1(19),11,15,17-tetraene-2,13-dione

C18H19ClO6 (366.087)

6-hydroxy-2-(3-hydroxybut-1-en-1-yl)-7-(3-methylbut-2-en-1-yl)-3,4-dihydro-2h-1-benzopyran-5-carbaldehyde

C19H24O4 (316.1675)

3,9-dihydroxy-5-(1h-indol-3-ylmethyl)-7,8,14,16-tetramethyl-22-oxa-4,21-diazapentacyclo[16.2.1.1⁵,⁸.0²,⁶.0²,¹⁰]docosa-1(20),3,11,15,18-pentaen-17-one

C32H35N3O4 (525.2627)

1-[(3r)-2,3-dihydroxy-5-(3-methylbut-2-en-1-yl)indol-3-yl]propan-2-one

C16H19NO3 (273.1365)

3-(5-hydroxy-7-methoxy-2-methyl-4-oxochromen-6-yl)-2-methylpropanoic acid

C15H16O6 (292.0947)

(1s,4r,8r,9s,11e,14s,16r,17s,18r,19s)-6,21-dihydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azapentacyclo[11.8.0.0¹,¹⁸.0⁴,⁸.0¹⁴,¹⁶]henicosa-6,11,20-triene-2,5-dione

C32H36N2O5 (528.2624)

(3s,6s)-3-{[5,7-bis(3-methylbut-2-en-1-yl)-2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methyl}-6-methyl-3,6-dihydropyrazine-2,5-diol

C29H39N3O2 (461.3042)

5-hydroxy-6-(5-hydroxy-2-methyl-3-oxohexyl)-7-methoxy-2-methylchromen-4-one

C18H22O6 (334.1416)

(1s,3s,11r,14s)-14-(hydroxymethyl)-3-(3-{[(1r,4s)-4-(hydroxymethyl)-5,7-dimethyl-6,8-dioxo-2,3-dithia-5,7-diazabicyclo[2.2.2]octan-1-yl]methyl}indol-1-yl)-18-methyl-15,16-dithia-10,12,18-triazapentacyclo[12.2.2.0¹,¹².0³,¹¹.0⁴,⁹]octadeca-4,6,8-triene-13,17-dione

C31H30N6O6S4 (710.111)

7,8-dihydroxy-3-propyl-4,6,7,8-tetrahydro-3h-2-benzopyran-1,5-dione

C12H16O5 (240.0998)

(2s)-2-{[hydroxy(2-hydroxy-6-methylphenyl)methylidene]amino}-3-methylbutanoic acid

C13H17NO4 (251.1158)

methyl 4-[4-(4,6-dimethyl-7-oxohepta-1,5-dien-1-yl)-3,5-dihydroxy-1-(1h-indol-3-ylmethyl)-7-methyl-6-methylidene-4,5,7,7a-tetrahydro-1h-isoindol-3a-yl]-4-oxobutanoate

C33H40N2O6 (560.2886)

methyl 5,7,12,20,22-pentahydroxy-24-methyl-9,18,27-trioxo-14-oxaheptacyclo[15.10.2.0¹,¹⁹.0³,¹⁶.0⁶,¹⁵.0⁸,¹³.0²¹,²⁶]nonacosa-3(16),4,6(15),7,19,21,23,25,28-nonaene-13-carboxylate

C31H24O11 (572.1319)

5-chloro-9-(3-hydroxy-2-methylbutanoyl)-6a-methyl-3-(3-methylpent-1-en-1-yl)-9h,9ah-furo[2,3-h]isochromene-6,8-dione

C23H27ClO6 (434.1496)

3-hydroxy-8-(hydroxymethyl)-5-(1h-indol-3-ylmethyl)-7,14,16-trimethyl-4,21-diazatetracyclo[16.2.1.0²,⁶.0²,¹⁰]henicosa-1(20),3,8,11,15,18-hexaen-17-one

C32H35N3O3 (509.2678)

6,21-dihydroxy-19-(1h-indol-3-ylmethyl)-7,9,16,17-tetramethyl-15-oxa-20-azatetracyclo[11.8.0.0¹,¹⁸.0¹⁴,¹⁶]henicosa-3,7,11,20-tetraene-2,5-dione

C32H36N2O5 (528.2624)

(z)-3',5,5',6'-tetrahydroxy-4,4'-dimethyl-[1,1'-bi(cyclohexylidene)]-3',4,5'-triene-2,2',3,6-tetrone

C14H10O8 (306.0376)

(6as)-5-chloro-9-[(2r,3r)-3-hydroxy-2-methylbutanoyl]-2-(2-hydroxyethyl)-6a-methyl-3-[(3s)-3-methylpent-1-en-1-yl]furo[2,3-h]isoquinoline-6,8-dione

C25H30ClNO6 (475.1762)

4'-epichaetoviridin f

C23H25ClO5 (416.139)

3-heptyl-7-methyl-6,8-dioxoisochromen-7-yl octanoate

C25H36O5 (416.2563)

(1r,2'r,3s,4''s,5r,6s)-4''-methyl-2-methylidene-5''-oxodispiro[bicyclo[3.1.1]heptane-6,4':2',2''-bis(oxolane)]-3-yl 3-hydroxy-2,2-dimethylbutanoate

C21H30O6 (378.2042)

9-(3-hydroxy-2-methylbutanoyl)-6a-methyl-3-(3-methylpent-1-en-1-yl)furo[2,3-h]isochromene-6,8-dione

C23H26O6 (398.1729)

(2s,3r,4s,5s,6r)-2-(3-chloro-6-hydroxy-4-methoxy-2-propylphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C16H23ClO8 (378.1081)

3-(2-hydroxypropyl)-5-methoxy-2-methylcyclohexa-2,5-diene-1,4-dione

C11H14O4 (210.0892)

methyl 6-hydroxy-7-methoxy-3-methyl-10-oxo-1h-pyrano[4,3-b]chromene-9-carboxylate

C16H14O7 (318.0739)

(3s)-5-chloro-6,8-dihydroxy-3,7-dimethyl-3,4-dihydro-2-benzopyran-1-one

C11H11ClO4 (242.0346)

(3ar,7r,16as)-2,7-dihydroxy-3-[(2s)-1-hydroxypropan-2-yl]-6,10,14,16a-tetramethyl-3ah,4h,7h,8h,9h,12h,13h,16h-cyclopenta[15]annulen-1-one

C25H38O4 (402.277)

(1s,14s)-5-methyl-3,6-dioxo-4-sulfanylidene-11-oxa-2,5-diazatricyclo[7.5.0.0²,⁷]tetradeca-7,9,12-trien-14-yl 3-(5-formyl-2-methoxyphenoxy)-4-methoxybenzoate

C28H22N2O9S (562.1046)

(3r,5e)-14,16-dihydroxy-3-methyl-4,7,8,9,10,12-hexahydro-3h-2-benzoxacyclotetradecine-1,11-dione

C18H22O5 (318.1467)

4-[4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-methoxy-3,5,6-trimethylbenzoyloxy]-2-methoxy-3,6-dimethylbenzoic acid

C30H32O10 (552.1995)

(5-amino-3,4,6-trihydroxyoxan-2-yl)methoxyphosphonic acid

C6H14NO8P (259.0457)

7'-(acetyloxy)-3,3'-bis(4-hydroxypentyl)-7,7'-dimethyl-6,6',8,8'-tetraoxo-[5,5'-biisochromen]-7-yl acetate

C34H38O12 (638.2363)

(1s,10s,12r,13r,14r,17r)-8-chloro-12-hydroxy-10,13,14-trimethyl-5-[(1e,3r)-3-methylpent-1-en-1-yl]-4,11,15-trioxatetracyclo[8.7.0.0²,⁷.0¹²,¹⁷]heptadeca-2,5,7-triene-9,16-dione

C23H27ClO6 (434.1496)

(3z,4s,5r,7r)-7-(hydroxymethyl)-3-[(2e)-pent-2-en-1-ylidene]-1,6-dioxaspiro[4.4]nonan-4-ol

C13H20O4 (240.1362)

(2e,6e)-7-[(1as,2r,2ar,5s,5ar,6s,6ar)-3-hydroxy-5-(1h-indol-3-ylmethyl)-6,6a-dimethyl-2a-(1h-pyrrol-2-yl)-1ah,2h,5h,5ah,6h-oxireno[2,3-f]isoindol-2-yl]-2,4-dimethylhepta-2,6-dienal

C32H37N3O3 (511.2835)

(3s,3ar,6s,6ar,10s,13r,17as)-1,6,13-trihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,6h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione

C32H36N2O5 (528.2624)

(2r,3s)-4-[(6as)-6a-methyl-3-[(1e,3s)-3-methylpent-1-en-1-yl]-6,8-dioxofuro[2,3-h]isochromen-9-yl]-3-methyl-4-oxobutan-2-yl (2r)-2-methoxy-2-phenylacetate

C32H34O8 (546.2254)

(3r,5s)-5-(deca-1,3,6,8-tetraen-5-yl)-3-hydroxyoxolan-2-one

C14H18O3 (234.1256)

6-hydroxy-3-[(5-hydroxy-6-methyloxan-2-yl)methyl]-8-methoxy-3,4-dihydro-2-benzopyran-1-one

C17H22O6 (322.1416)

(2r,3r,7s)-3-hydroxy-7-methyl-2-[(1e)-prop-1-en-1-yl]-2h,3h,6h,7h-pyrano[2,3-b]pyran-4,5-dione

C12H14O5 (238.0841)

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

C11H20O10 (312.1056)

4-[4-(2,4-dihydroxy-3,6-dimethylbenzoyloxy)-2-methoxy-3,6-dimethylbenzoyloxy]-2-hydroxy-3,6-dimethylbenzoic acid

C28H28O10 (524.1682)

(3s,5s,6r,10r)-6-hydroxy-3-methyl-10-[(1e)-prop-1-en-1-yl]-2-oxaspiro[4.5]dec-8-ene-1,4,7-trione

C13H14O5 (250.0841)

5-chloro-2-[2-(2-hydroxyethoxy)ethyl]-6a-methyl-3-(3-methylpent-1-en-1-yl)-9-propanoylfuro[2,3-h]isoquinoline-6,8-dione

C25H30ClNO6 (475.1762)

methyl 4-(acetyloxy)-3-hydroxycyclohex-1-ene-1-carboxylate

C10H14O5 (214.0841)

2-ethoxy-5-hydroxy-6-methyl-4-oxooxan-3-yl 2,4-dihydroxy-6-methylbenzoate

C16H20O8 (340.1158)

1,13-dihydroxy-3-(1h-indol-3-ylmethyl)-4,5,10,12-tetramethyl-3h,3ah,4h,6ah,9h,10h,13h-cyclotrideca[d]isoindole-14,17-dione

C32H36N2O4 (512.2675)

methyl (6as,8r,9r,9as)-5-chloro-8-hydroxy-8-[(2r,3r)-3-hydroxybutan-2-yl]-6a-methyl-3-[(1e,3s)-3-methylpent-1-en-1-yl]-6-oxo-9h,9ah-furo[2,3-h]isochromene-9-carboxylate

C24H31ClO7 (466.1758)

10-hydroxy-3-methoxy-4-methylidene-11-[(1e)-prop-1-en-1-yl]-6-oxa-3-azatricyclo[5.3.1.0¹,⁵]undecane-2,9-dione

C14H17NO5 (279.1107)

(5s)-3-[(1r,2s,4as,6s,8ar)-2-(but-2-en-2-yl)-3,4a,6-trimethyl-2,5,6,7,8,8a-hexahydro-1h-naphthalene-1-carbonyl]-5-methoxy-5-(2-methylpropyl)pyrrol-2-ol

C27H41NO3 (427.3086)

7,15-dihydroxy-4-methoxy-13-methyl-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-one

C16H14O5 (286.0841)

6,15-dihydroxy-4,7-dimethoxy-13-methyl-9-oxatricyclo[9.4.0.0³,⁸]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-one

C17H16O6 (316.0947)

(5r,6r,10z)-6-hydroxy-2-methoxy-3-methylidene-10-propylidene-2-azaspiro[4.5]dec-8-ene-1,4,7-trione

C14H15NO5 (277.095)

(1r,9ar,9br,11ar)-1-[(2r,3e,5s)-6-hydroxy-5,6-dimethylhept-3-en-2-yl]-9a,11a-dimethyl-1h,2h,3h,8h,9h,9bh,10h,11h-cyclopenta[a]phenanthren-7-one

C28H40O2 (408.3028)

5-hydroxy-6,8,10-trimethoxy-2-methyl-2h,3h-naphtho[2,3-b]pyran-4-one

C17H18O6 (318.1103)

6-[(6,8-dihydroxy-3,7-dimethyl-1-oxo-3,4-dihydro-2-benzopyran-5-yl)methyl]-5-hydroxy-7-methoxy-2-methylchromen-4-one

C23H22O8 (426.1315)

(2s,3r)-5,6,8-trihydroxy-2,3-dimethyl-9-[(2r,3r)-5,6,8-trihydroxy-2,3-dimethyl-4-oxo-2h,3h-naphtho[2,3-b]pyran-9-yl]-2h,3h-naphtho[2,3-b]pyran-4-one

C30H26O10 (546.1526)

(3s,6z)-3-methyl-6-{[2-(2-methylbut-3-en-2-yl)-1h-indol-3-yl]methylidene}-3h-pyrazine-2,5-diol

C19H21N3O2 (323.1634)