NCBI Taxonomy: 423307

Crescentieae (ncbi_taxid: 423307)

found 93 associated metabolites at tribe taxonomy rank level.

Ancestor: Tabebuia alliance

Child Taxonomies: Amphitecna, Crescentia, Parmentiera, Spirotecoma

Agnuside

((1S,4AR,5S,7AS)-5-HYDROXY-1-(((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2-YL)OXY)-1,4A,5,7A-TETRAHYDROCYCLOPENTA[C]PYRAN-7-YL)METHYL 4-HYDROXYBENZOATE

C22H26O11 (466.14750460000005)


Agnuside is a benzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with the primary hydroxy group of aucubin. It is an iridoid glycoside found in several Vitex plants including Vitex agnus-castus. It has a role as a plant metabolite, an anti-inflammatory agent, a pro-angiogenic agent and a cyclooxygenase 2 inhibitor. It is a terpene glycoside, an iridoid monoterpenoid, a benzoate ester, a member of phenols, a beta-D-glucoside, a cyclopentapyran and a monosaccharide derivative. It is functionally related to an aucubin. Agnuside is a natural product found in Crescentia cujete, Vitex peduncularis, and other organisms with data available. See also: Chaste tree fruit (part of); Vitex negundo leaf (part of). Isolated from Vitex agnus-castus (agnus castus). Agnuside is found in herbs and spices and fruits. Agnuside is found in fruits. Agnuside is isolated from Vitex agnus-castus (agnus castus). Agnuside is a compound isolated from Vitex negundo, down-regulates pro-inflammatory mediators PGE2 and LTB4, and reduces the expression of cytokines, with anti-arthritic activity[1]. Agnuside is used in the study of asthma, inflammation, and angiogenic diseases. Agnuside is an orally active compound that can be extracted from Vitex negundo[1][2][3][4]. Agnuside is a compound isolated from Vitex negundo, down-regulates pro-inflammatory mediators PGE2 and LTB4, and reduces the expression of cytokines, with anti-arthritic activity[1].

   

Sucrose

(2R,3R,4S,5S,6R)-2-(((2S,3S,4S,5R)-3,4-Dihydroxy-2,(2R,3R,4S,5S,6R)-2-{[(2S,3S,4S,5R)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C12H22O11 (342.1162062)


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

   

Aucubin

(2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C15H22O9 (346.1263762)


Aucubin is found in common verbena. Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety. Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally. Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis. The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1 Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety.; Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.; Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis.; The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1. Aucubin is an organic molecular entity. It has a role as a metabolite. Aucubin is a natural product found in Verbascum lychnitis, Plantago media, and other organisms with data available. See also: Chaste tree fruit (part of); Rehmannia glutinosa Root (part of); Plantago ovata seed (part of). Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3]. Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3].

   

Rutin

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

C27H30O16 (610.153378)


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

   

Kaempferol

3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one

C15H10O6 (286.047736)


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

   

Glycerol

propane-1,2,3-triol

C3H8O3 (92.0473418)


Glycerol or glycerin is a colourless, odourless, viscous liquid that is sweet-tasting and mostly non-toxic. It is widely used in the food industry as a sweetener and humectant and in pharmaceutical formulations. Glycerol is an important component of triglycerides (i.e. fats and oils) and of phospholipids. Glycerol is a three-carbon substance that forms the backbone of fatty acids in fats. When the body uses stored fat as a source of energy, glycerol and fatty acids are released into the bloodstream. The glycerol component can be converted into glucose by the liver and provides energy for cellular metabolism. Normally, glycerol shows very little acute toxicity and very high oral doses or acute exposures can be tolerated. On the other hand, chronically high levels of glycerol in the blood are associated with glycerol kinase deficiency (GKD). GKD causes the condition known as hyperglycerolemia, an accumulation of glycerol in the blood and urine. There are three clinically distinct forms of GKD: infantile, juvenile, and adult. The infantile form is the most severe and is associated with vomiting, lethargy, severe developmental delay, and adrenal insufficiency. The mechanisms of glycerol toxicity in infants are not known, but it appears to shift metabolism towards chronic acidosis. Acidosis typically occurs when arterial pH falls below 7.35. In infants with acidosis, the initial symptoms include poor feeding, vomiting, loss of appetite, weak muscle tone (hypotonia), and lack of energy (lethargy). These can progress to heart, liver, and kidney abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated GKD. Many affected children with organic acidemias experience intellectual disability or delayed development. Patients with the adult form of GKD generally have no symptoms and are often detected fortuitously. Glycerol. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=56-81-5 (retrieved 2024-07-01) (CAS RN: 56-81-5). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Isovanillic acid

3-Hydroxy-4-methoxybenzoic acid

C8H8O4 (168.0422568)


Isovanillic acid is a metabolite of isovanillin. Isovanillin is a phenolic aldehyde, an organic compound and isomer of vanillin. It is a selective inhibitor of aldehyde oxidase. It is not a substrate of that enzyme, and is metabolized by aldehyde dehydrogenase into isovanillic acid. (Wikipedia) Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid isolated from isolated from Scrophularia ningpoensis, with Anti-inflammatory activity[1]. Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid isolated from isolated from Scrophularia ningpoensis, with Anti-inflammatory activity[1].

   

Biorobin

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

C27H30O15 (594.158463)


Isolated from Medicago subspecies, Trigonella subspecies and other plant subspecies Kaempferol 3-robinobioside is found in herbs and spices and pulses. Biorobin is found in herbs and spices. Biorobin is isolated from Medicago species, Trigonella species and other plant species.

   

(3,4,5,6-tetrahydroxyoxan-2-yl)methyl 4-hydroxybenzoate

(3,4,5,6-tetrahydroxyoxan-2-yl)methyl 4-hydroxybenzoate

C13H16O8 (300.0845136)


   

(R)-1-O-b-D-glucopyranosyl-1,3-octanediol

2-(hydroxymethyl)-6-[(3-hydroxyoctyl)oxy]oxane-3,4,5-triol

C14H28O7 (308.1834938)


(R)-1-O-b-D-glucopyranosyl-1,3-octanediol is found in pomes. (R)-1-O-b-D-glucopyranosyl-1,3-octanediol is a constituent of apples Constituent of apples. (R)-1-O-b-D-glucopyranosyl-1,3-octanediol is found in pomes.

   

(R)-1-O-[b-D-Glucopyranosyl-(1->6)-b-D-glucopyranoside]-1,3-octanediol

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

C20H38O12 (470.2363148)


(R)-1-O-[b-D-Glucopyranosyl-(1->6)-b-D-glucopyranoside]-1,3-octanediol is found in fruits. (R)-1-O-[b-D-Glucopyranosyl-(1->6)-b-D-glucopyranoside]-1,3-octanediol is a constituent of calabash tree (Crescentia cujete) fruits. Constituent of calabash tree (Crescentia cujete) fruits. (R)-1-O-[b-D-Glucopyranosyl-(1->6)-b-D-glucopyranoside]-1,3-octanediol is found in fruits.

   

3h-Sucrose

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

C12H22O11 (342.11620619999997)


Sweetening agent and food source assimilated by most organismsand is also used in food products as a preservative, antioxidant, moisture control agent, stabiliser and thickening agent. Widespread in seeds, leaves, fruits, flowers and roots of plants, where it functions as an energy store for metabolism and as a carbon source for biosynth. Annual world production is in excess of 90 x 106 tons mainly from the juice of sugar cane and sugar beet which contain respectively ca. 20\\% and ca. 17\\% of the sugar. Sucrose is found in many foods, some of which are rowanberry, brassicas, calabash, and hedge mustard.

   

Quercetin-3-o-rutinose

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

C27H30O16 (610.153378)


   

Kaempferol 3-rhamno-glucoside

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

C27H30O15 (594.158463)


Kaempferol 3-rhamno-glucoside, also known as nicotiflorin or kaempferol 3-rutinoside, is a member of the class of compounds known as flavonoid-3-o-glycosides. Flavonoid-3-o-glycosides are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. Kaempferol 3-rhamno-glucoside is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Kaempferol 3-rhamno-glucoside can be found in ginkgo nuts and tea, which makes kaempferol 3-rhamno-glucoside a potential biomarker for the consumption of these food products. Nicotiflorin is a flavonoid glycoside extracted from a traditional Chinese medicine Carthamus tinctorius. Nicotiflorin shows potent antiglycation activity and neuroprotection effects. Nicotiflorin is a flavonoid glycoside extracted from a traditional Chinese medicine Carthamus tinctorius. Nicotiflorin shows potent antiglycation activity and neuroprotection effects.

   

isovanillic acid

InChI=1\C8H8O4\c1-12-7-3-2-5(8(10)11)4-6(7)9\h2-4,9H,1H3,(H,10,11

C8H8O4 (168.0422568)


Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid isolated from isolated from Scrophularia ningpoensis, with Anti-inflammatory activity[1]. Isovanillic acid (3-Hydroxy-4-methoxybenzoic acid) is a phenolic acid isolated from isolated from Scrophularia ningpoensis, with Anti-inflammatory activity[1].

   

Agnuside

((1S,4AR,5S,7AS)-5-HYDROXY-1-(((2S,3R,4S,5S,6R)-3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)TETRAHYDRO-2H-PYRAN-2-YL)OXY)-1,4A,5,7A-TETRAHYDROCYCLOPENTA[C]PYRAN-7-YL)METHYL 4-HYDROXYBENZOATE

C22H26O11 (466.14750460000005)


Agnuside is a benzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with the primary hydroxy group of aucubin. It is an iridoid glycoside found in several Vitex plants including Vitex agnus-castus. It has a role as a plant metabolite, an anti-inflammatory agent, a pro-angiogenic agent and a cyclooxygenase 2 inhibitor. It is a terpene glycoside, an iridoid monoterpenoid, a benzoate ester, a member of phenols, a beta-D-glucoside, a cyclopentapyran and a monosaccharide derivative. It is functionally related to an aucubin. Agnuside is a natural product found in Crescentia cujete, Vitex peduncularis, and other organisms with data available. See also: Chaste tree fruit (part of); Vitex negundo leaf (part of). A benzoate ester resulting from the formal condensation of the carboxy group of 4-hydroxybenzoic acid with the primary hydroxy group of aucubin. It is an iridoid glycoside found in several Vitex plants including Vitex agnus-castus. Agnuside is a compound isolated from Vitex negundo, down-regulates pro-inflammatory mediators PGE2 and LTB4, and reduces the expression of cytokines, with anti-arthritic activity[1]. Agnuside is used in the study of asthma, inflammation, and angiogenic diseases. Agnuside is an orally active compound that can be extracted from Vitex negundo[1][2][3][4]. Agnuside is a compound isolated from Vitex negundo, down-regulates pro-inflammatory mediators PGE2 and LTB4, and reduces the expression of cytokines, with anti-arthritic activity[1].

   

Aucubin

(2S,3R,4S,5S,6R)-2-(((1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl)oxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

C15H22O9 (346.1263762)


Aucubin is an organic molecular entity. It has a role as a metabolite. Aucubin is a natural product found in Verbascum lychnitis, Plantago media, and other organisms with data available. See also: Chaste tree fruit (part of); Rehmannia glutinosa Root (part of); Plantago ovata seed (part of). Origin: Plant; SubCategory_DNP: Monoterpenoids, Iridoid monoterpenoids SubCategory_DNP: Monoterpenoids, Iridoid monoterpenoids; Origin: Plant Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3]. Aucubin, an iridoid glucoside, is isolated from Plantago asiatica, Eucommia ulmoides, the leaves of Aucuba japonica and more recently from butterfly larva. Aucubin has many biological activities, such as antioxidant, anti-aging, anti-inflammatory, antimicrobial, anti-fibrotic, anti-cancer, hepatoprotective, neuroprotective and osteoprotective effects[1][2][3].

   

Rutin

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

C27H30O16 (610.153378)


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

   

Sucrose

Sucrose

C12H22O11 (342.11620619999997)


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

   

glycerol

glycerol

C3H8O3 (92.0473418)


A triol with a structure of propane substituted at positions 1, 2 and 3 by hydroxy groups.

   

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

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

C12H22O11 (342.11620619999997)


   

3-Hydroxy-4-methoxybenzoic acid

3-Hydroxy-4-methoxybenzoic acid

C8H8O4 (168.0422568)


   

(R)-1-O-b-D-glucopyranosyl-1,3-octanediol

2-(hydroxymethyl)-6-[(3-hydroxyoctyl)oxy]oxane-3,4,5-triol

C14H28O7 (308.1834938)


   

(R)-1-O-[b-D-Glucopyranosyl-(1->6)-b-D-glucopyranoside]-1,3-octanediol

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

C20H38O12 (470.2363148)


   

Acanthoside D

Eleutheroside E

C34H46O18 (742.2684016000001)


Isolated from Siberian ginseng (Eleutherococcus (Acanthopanax) senticosus). Acanthoside D is found in tea.

   

(3,4,5,6-tetrahydroxyoxan-2-yl)methyl 4-hydroxybenzoate

(3,4,5,6-tetrahydroxyoxan-2-yl)methyl 4-hydroxybenzoate

C13H16O8 (300.0845136)


   

(1s,2s,4s,5s,6r,10r)-10-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]decan-5-yl benzoate

(1s,2s,4s,5s,6r,10r)-10-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]decan-5-yl benzoate

C16H18O6 (306.11033280000004)


   

7-hydroxy-14-(hydroxymethyl)-12,16-dioxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-1(10),3,5,7,11(15),13-hexaene-2,9-dione

7-hydroxy-14-(hydroxymethyl)-12,16-dioxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-1(10),3,5,7,11(15),13-hexaene-2,9-dione

C15H8O6 (284.0320868)


   

2-(hydroxymethyl)-6-{[4-(hydroxymethyl)-3ah,4h,6ah-cyclopenta[b]furan-5-yl]methoxy}oxane-3,4,5-triol

2-(hydroxymethyl)-6-{[4-(hydroxymethyl)-3ah,4h,6ah-cyclopenta[b]furan-5-yl]methoxy}oxane-3,4,5-triol

C15H22O8 (330.1314612)


   

(2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H24O10 (364.13694039999996)


   

[(3as,4s,6ar)-5-(hydroxymethyl)-3ah,4h,6ah-cyclopenta[b]furan-4-yl]methanol

[(3as,4s,6ar)-5-(hydroxymethyl)-3ah,4h,6ah-cyclopenta[b]furan-4-yl]methanol

C9H12O3 (168.0786402)


   

(2s,3r,4s,5s,6s)-2-{4-[(1s,3ar,4s,6ar)-4-(3,5-dimethoxy-4-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6s)-2-{4-[(1s,3ar,4s,6ar)-4-(3,5-dimethoxy-4-{[(2s,3s,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)-hexahydrofuro[3,4-c]furan-1-yl]-2,6-dimethoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C34H46O18 (742.2684016000001)


   

(1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

(1s,4ar,5r,7s,7as)-7-hydroxy-7-methyl-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H28O11 (468.16315380000003)


   

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

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

C11H22O7 (266.1365462)


   

[5-(hydroxymethyl)-3ah,4h,6ah-cyclopenta[b]furan-4-yl]methanol

[5-(hydroxymethyl)-3ah,4h,6ah-cyclopenta[b]furan-4-yl]methanol

C9H12O3 (168.0786402)


   

2-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]benzoic acid

2-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]benzoic acid

C13H16O7 (284.0895986)


   

(2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol

(2r,3s,4s,5r,6r)-5-{[(2s,3r,4r)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4-diol

C19H36O11 (440.22575059999997)


   

2-(hydroxymethyl)-6-[(4-hydroxypentan-2-yl)oxy]oxane-3,4,5-triol

2-(hydroxymethyl)-6-[(4-hydroxypentan-2-yl)oxy]oxane-3,4,5-triol

C11H22O7 (266.1365462)


   

[(4as,7as)-5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate

[(4as,7as)-5-hydroxy-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-7-yl]methyl 4-hydroxybenzoate

C22H26O11 (466.14750460000005)


   

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

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

C11H20O7 (264.120897)


   

2-[(4-hydroxypentan-2-yl)oxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol

2-[(4-hydroxypentan-2-yl)oxy]-6-{[(3,4,5-trihydroxyoxan-2-yl)oxy]methyl}oxane-3,4,5-triol

C16H30O11 (398.178803)


   

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

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

C11H20O7 (264.120897)


   

2-hydroxy-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[(4-hydroxybenzoyloxy)methyl]oxan-2-yl]oxy}benzoic acid

2-hydroxy-6-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-[(4-hydroxybenzoyloxy)methyl]oxan-2-yl]oxy}benzoic acid

C20H20O11 (436.100557)


   

2-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl 4-hydroxybenzoate

2-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl 4-hydroxybenzoate

C16H20O6 (308.125982)


   

(2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(1s,4ar,5r,7s,7as)-5,7-dihydroxy-7-methyl-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H24O9 (348.14202539999997)


   

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

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

C20H38O12 (470.2363148)


   

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

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

C17H30O12 (426.173718)


   

6-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-(4-hydroxybenzoyloxy)-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexa-2,4-diene-1-carboxylic acid

6-{[(2r,3r,4s,5r,6r)-3,5-dihydroxy-4-(4-hydroxybenzoyloxy)-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexa-2,4-diene-1-carboxylic acid

C20H22O11 (438.11620619999997)


   

7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

7-(hydroxymethyl)-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H26O11 (466.14750460000005)


   

2-({4-hydroxy-2,10-dioxatricyclo[5.3.1.0⁴,⁸]undec-5-en-9-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

2-({4-hydroxy-2,10-dioxatricyclo[5.3.1.0⁴,⁸]undec-5-en-9-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O9 (346.1263762)


   

(2s,3r,4s,5s,6r)-2-{[(1r,4s,7s,8s,9s)-4-hydroxy-2,10-dioxatricyclo[5.3.1.0⁴,⁸]undec-5-en-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(1r,4s,7s,8s,9s)-4-hydroxy-2,10-dioxatricyclo[5.3.1.0⁴,⁸]undec-5-en-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O9 (346.1263762)


   

(4r,5r)-4-hydroxy-5-(2-hydroxyethyl)-2-(hydroxymethyl)cyclopent-1-ene-1-carboxylic acid

(4r,5r)-4-hydroxy-5-(2-hydroxyethyl)-2-(hydroxymethyl)cyclopent-1-ene-1-carboxylic acid

C9H14O5 (202.08411940000002)


   

(1s,4ar,5r,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

(1s,4ar,5r,7as)-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H26O11 (466.14750460000005)


   

(4r,5r)-4-hydroxy-5-(2-hydroxyethyl)-2-methylcyclopent-1-ene-1-carboxylic acid

(4r,5r)-4-hydroxy-5-(2-hydroxyethyl)-2-methylcyclopent-1-ene-1-carboxylic acid

C9H14O4 (186.0892044)


   

4-hydroxy-5-(2-hydroxyethyl)-2-methylcyclopent-1-ene-1-carboxylic acid

4-hydroxy-5-(2-hydroxyethyl)-2-methylcyclopent-1-ene-1-carboxylic acid

C9H14O4 (186.0892044)


   

5-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-[(3-hydroxyoctyl)oxy]oxane-3,4-diol

5-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-2-(hydroxymethyl)-6-[(3-hydroxyoctyl)oxy]oxane-3,4-diol

C19H36O11 (440.22575059999997)


   

(2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4,5-triol

(2r,3s,4s,5r,6r)-2-(hydroxymethyl)-6-{[(3r)-3-hydroxyoctyl]oxy}oxane-3,4,5-triol

C14H28O7 (308.1834938)


   

(1s,2s,4s,5s,6r,10s)-10-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]decan-5-yl benzoate

(1s,2s,4s,5s,6r,10s)-10-hydroxy-2-(hydroxymethyl)-3,9-dioxatricyclo[4.4.0.0²,⁴]decan-5-yl benzoate

C16H18O6 (306.11033280000004)


   

(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxybenzoate

(6-{[3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxybenzoate

C19H26O13 (462.13733460000003)


   

(3ar,4s,9as,9br)-9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

(3ar,4s,9as,9br)-9-(hydroxymethyl)-6-methyl-3-methylidene-2,7-dioxo-3ah,4h,5h,9ah,9bh-azuleno[4,5-b]furan-4-yl 2-methylprop-2-enoate

C19H20O6 (344.125982)


   

[(2r,3s,4s,5r,6r)-6-{[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxybenzoate

[(2r,3s,4s,5r,6r)-6-{[(2s,3s,4s,5r)-3,4-dihydroxy-2,5-bis(hydroxymethyl)oxolan-2-yl]oxy}-3,4,5-trihydroxyoxan-2-yl]methyl 4-hydroxybenzoate

C19H26O13 (462.13733460000003)


   

(1r,2r)-2-(2-hydroxyethyl)-3-(hydroxymethyl)-4-methylcyclopent-3-en-1-yl 4-hydroxybenzoate

(1r,2r)-2-(2-hydroxyethyl)-3-(hydroxymethyl)-4-methylcyclopent-3-en-1-yl 4-hydroxybenzoate

C16H20O5 (292.13106700000003)


   

(2r,3r,4s,5s,6r)-2-{[(2r,4s)-4-hydroxypentan-2-yl]oxy}-6-({[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(2r,4s)-4-hydroxypentan-2-yl]oxy}-6-({[(2s,3r,4s,5r)-3,4,5-trihydroxyoxan-2-yl]oxy}methyl)oxane-3,4,5-triol

C16H30O11 (398.178803)


   

benzoyl-β-d-glucoside

benzoyl-β-d-glucoside

C13H16O7 (284.0895986)


   

(1s,4ar,5s,7as)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-6-yl 4-hydroxybenzoate

(1s,4ar,5s,7as)-5-hydroxy-7-(hydroxymethyl)-1-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,7ah-cyclopenta[c]pyran-6-yl 4-hydroxybenzoate

C22H26O12 (482.14241960000004)


   

7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

7-hydroxy-7-methyl-1-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-5-yl 4-hydroxybenzoate

C22H28O11 (468.16315380000003)


   

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

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

C17H32O12 (428.1893672)


   

(2s,3r,4s,5s,6r)-2-{[(1s,3s,7s,8s,9s)-3-hydroxy-2,10-dioxatricyclo[5.3.1.0⁴,⁸]undec-5-en-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(1s,3s,7s,8s,9s)-3-hydroxy-2,10-dioxatricyclo[5.3.1.0⁴,⁸]undec-5-en-9-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O9 (346.1263762)


   

(1r,2r)-2-(2-hydroxyethyl)-3-(hydroxymethyl)-4-methylcyclopent-3-en-1-yl benzoate

(1r,2r)-2-(2-hydroxyethyl)-3-(hydroxymethyl)-4-methylcyclopent-3-en-1-yl benzoate

C16H20O4 (276.13615200000004)


   

14-(hydroxymethyl)-12,16-dioxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-1(10),3,5,7,11(15),13-hexaene-2,9-dione

14-(hydroxymethyl)-12,16-dioxatetracyclo[8.6.0.0³,⁸.0¹¹,¹⁵]hexadeca-1(10),3,5,7,11(15),13-hexaene-2,9-dione

C15H8O5 (268.0371718)


   

4-hydroxy-5-(2-hydroxyethyl)-2-(hydroxymethyl)cyclopent-1-ene-1-carboxylic acid

4-hydroxy-5-(2-hydroxyethyl)-2-(hydroxymethyl)cyclopent-1-ene-1-carboxylic acid

C9H14O5 (202.08411940000002)


   

[5-(hydroxymethyl)-2h,3h,3ah,4h,6ah-cyclopenta[b]furan-4-yl]methanol

[5-(hydroxymethyl)-2h,3h,3ah,4h,6ah-cyclopenta[b]furan-4-yl]methanol

C9H14O3 (170.0942894)


   

4-(2-hydroxyethyl)-5-(hydroxymethyl)-1-methylcyclopentane-1,3-diol

4-(2-hydroxyethyl)-5-(hydroxymethyl)-1-methylcyclopentane-1,3-diol

C9H18O4 (190.1205028)


   

(4ar,5r)-5-hydroxy-7-methyl-3h,4h,4ah,5h,6h-cyclopenta[c]pyran-1-one

(4ar,5r)-5-hydroxy-7-methyl-3h,4h,4ah,5h,6h-cyclopenta[c]pyran-1-one

C9H12O3 (168.0786402)


   

stigmast-5-en-3-ol, (3β)-

stigmast-5-en-3-ol, (3β)-

C29H50O (414.386145)


   

(2s,3r,4s,5s,6r)-2-{[(1r,2s,4s,5s,8r,10s,11s)-5-hydroxy-3,7,9-trioxatetracyclo[6.3.1.0²,⁴.0⁵,¹¹]dodecan-10-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2s,3r,4s,5s,6r)-2-{[(1r,2s,4s,5s,8r,10s,11s)-5-hydroxy-3,7,9-trioxatetracyclo[6.3.1.0²,⁴.0⁵,¹¹]dodecan-10-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O10 (362.1212912)


   

2-{[5,7-dihydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

2-{[5,7-dihydroxy-7-(hydroxymethyl)-1h,4ah,5h,6h,7ah-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H24O10 (364.13694039999996)


   

(2r,3r,4s,5s,6r)-2-{[(3ar,4s,6ar)-4-(hydroxymethyl)-2h,3h,3ah,4h,6ah-cyclopenta[b]furan-5-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(3ar,4s,6ar)-4-(hydroxymethyl)-2h,3h,3ah,4h,6ah-cyclopenta[b]furan-5-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H24O8 (332.1471104)


   

(2r,3r,4s,5s,6r)-2-{[(3as,4s,6ar)-4-(hydroxymethyl)-3ah,4h,6ah-cyclopenta[b]furan-5-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

(2r,3r,4s,5s,6r)-2-{[(3as,4s,6ar)-4-(hydroxymethyl)-3ah,4h,6ah-cyclopenta[b]furan-5-yl]methoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O8 (330.1314612)


   

(1r,2r)-2-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl 4-hydroxybenzoate

(1r,2r)-2-(2-hydroxyethyl)-3,4-bis(hydroxymethyl)cyclopent-3-en-1-yl 4-hydroxybenzoate

C16H20O6 (308.125982)


   

(4r)-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}pentan-2-one

(4r)-4-{[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-({[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}methyl)oxan-2-yl]oxy}pentan-2-one

C17H30O12 (426.173718)


   

2-({5-hydroxy-3,7,9-trioxatetracyclo[6.3.1.0²,⁴.0⁵,¹¹]dodecan-10-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

2-({5-hydroxy-3,7,9-trioxatetracyclo[6.3.1.0²,⁴.0⁵,¹¹]dodecan-10-yl}oxy)-6-(hydroxymethyl)oxane-3,4,5-triol

C15H22O10 (362.1212912)


   

[(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 4-hydroxybenzoate

[(2r,3s,4s,5r,6s)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 4-hydroxybenzoate

C13H16O8 (300.0845136)


   

2-(hydroxymethyl)-6-{[4-(hydroxymethyl)-2h,3h,3ah,4h,6ah-cyclopenta[b]furan-5-yl]methoxy}oxane-3,4,5-triol

2-(hydroxymethyl)-6-{[4-(hydroxymethyl)-2h,3h,3ah,4h,6ah-cyclopenta[b]furan-5-yl]methoxy}oxane-3,4,5-triol

C15H24O8 (332.1471104)


   

[(3ar,4s,6ar)-5-(hydroxymethyl)-2h,3h,3ah,4h,6ah-cyclopenta[b]furan-4-yl]methanol

[(3ar,4s,6ar)-5-(hydroxymethyl)-2h,3h,3ah,4h,6ah-cyclopenta[b]furan-4-yl]methanol

C9H14O3 (170.0942894)


   

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

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

C45H80O2 (652.615798)


   

(4ar,5s,6s,7r,7ar)-5,6,7-trihydroxy-7-(hydroxymethyl)-hexahydrocyclopenta[c]pyran-3-one

(4ar,5s,6s,7r,7ar)-5,6,7-trihydroxy-7-(hydroxymethyl)-hexahydrocyclopenta[c]pyran-3-one

C9H14O6 (218.0790344)


   

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

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

C17H32O12 (428.1893672)


   

(1r,4ar,5s,6r,7r,7as)-7-(hydroxymethyl)-hexahydro-1h-cyclopenta[c]pyran-1,5,6,7-tetrol

(1r,4ar,5s,6r,7r,7as)-7-(hydroxymethyl)-hexahydro-1h-cyclopenta[c]pyran-1,5,6,7-tetrol

C9H16O6 (220.0946836)


   

(1s,3r,4r,5r)-4-(2-hydroxyethyl)-5-(hydroxymethyl)-1-methylcyclopentane-1,3-diol

(1s,3r,4r,5r)-4-(2-hydroxyethyl)-5-(hydroxymethyl)-1-methylcyclopentane-1,3-diol

C9H18O4 (190.1205028)