Classification Term: 3738
Glucuronic acid derivatives (ontology term: CHEMONTID:0002094)
Compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid." []
found 33 associated metabolites at family metabolite taxonomy ontology rank level.
Ancestor: Sugar acids and derivatives
Child Taxonomies: Glucuronides
D-Glucuronate
Glucuronic acid (CAS: 6556-12-3) is a carboxylic acid that has the structure of a glucose molecule that has had its sixth carbon atom (of six total) oxidized. The salts of glucuronic acid are known as glucuronates. Glucuronic acid is highly soluble in water. In humans, glucuronic acid is often linked to toxic or poisonous substances to allow for subsequent elimination, and to hormones to allow for easier transport. These linkages involve O-glycosidic bonds. The process is known as glucuronidation, and the resulting substances are known as glucuronides (or glucuronosides). Glucuronidation uses UDP-glucuronic acid (glucuronic acid linked via a glycosidic bond to uridine diphosphate) as an intermediate. UDP-glucuronic acid is formed in the liver of all animals. D-Glucuronic acid is an important intermediate isolated from many gums. D-Glucuronic acid and its derivative glucuronolactone are as a liver antidote in the prophylaxis of human health. D-Glucuronic acid has an anti-inflammatory effect for the skin[1]. D-Glucuronic acid is an important intermediate isolated from many gums. D-Glucuronic acid and its derivative glucuronolactone are as a liver antidote in the prophylaxis of human health. D-Glucuronic acid has an anti-inflammatory effect for the skin[1].
Glucaric acid
Glucaric acid, also known as glucarate or D-saccharic acid, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Glucaric acid is a sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups. D-glucaric acid is found in fruits, vegetables, and mammals. The highest concentrations of glucaric acid are found in grapefruits, apples, oranges, and cruciferous vegetables (PMID: 18772850). Glucaric acid is produced through the oxidation of glucose. Cytochrome P450 is thought to be responsible for the production of D-glucaric acid in vivo (PMID: 3779687). In mammals, D-glucaric acid and D-glucaro-l,4-lactone are also known end-products of the D-glucuronic acid pathway (PMID: 18772850). Glucaric is available as a dietary supplement in the form of calcium D-glucarate and has been studied for therapeutic purposes including cholesterol reduction and cancer chemotherapy (PMID: 9101079). D-Glucaric acid has a potential use as a building block for a number of polymers, including new nylons and hyperbranched polyesters. D-glucaric acid produced from D-glucose has been successfully utilized to produce a hydroxylated nylon. A sugar acid derived from D-glucose in which both the aldehydic carbon atom and the carbon atom bearing the primary hydroxyl group are oxidized to carboxylic acid groups. [HMDB] KEIO_ID S025
Galacturonic acid
D-Glucuronic acid is an important intermediate isolated from many gums. D-Glucuronic acid and its derivative glucuronolactone are as a liver antidote in the prophylaxis of human health. D-Glucuronic acid has an anti-inflammatory effect for the skin[1]. D-Glucuronic acid is an important intermediate isolated from many gums. D-Glucuronic acid and its derivative glucuronolactone are as a liver antidote in the prophylaxis of human health. D-Glucuronic acid has an anti-inflammatory effect for the skin[1].
a-L-threo-4-Hex-4-enopyranuronosyl-D-galacturonic acid
a-L-threo-4-Hex-4-enopyranuronosyl-D-galacturonic acid is isolated from the enzymic hydrolysate of pectin produced by the pectin-trans eliminase from Bacillus polymyxa or commercial pectinase. Isolated from the enzymic hydrolysate of pectin produced by the pectin-trans eliminase from Bacillus polymyxa or commercial pectinase
Galactaric acid
Galactaric acid, also known as mucic acid or galactarate, belongs to the class of organic compounds known as glucuronic acid derivatives. Glucuronic acid derivatives are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Technically, galactaric acid is an aldaric acid obtained by oxidation of galactose. Galactaric acid exists as a white crystalline powder, which melts at 210 - 230 oC. It is insoluble in alcohol, and nearly insoluble in cold water (1 g/300 mL) but more soluble in hot water (1 g/60 mL).. Galactaric acid exists in all living organisms, ranging from bacteria to plants to humans. In plants, galactaric acid is commonly produced or utilized as an osmorgulator (PMID: 31505987). Galactaric acid has been detected, but not quantified in, several different foods, such as fruits, vegetables and bovine milk. A recent large-scale dietary study found that galactaric acid can serve as a biomarker for long-term dairy intake and for the consumption of carotenoid-rich vegetables (PMID: 33566801). In food production, galactaric acid can be used to replace tartaric acid in self-rising flour or fizzies. Present in ripe fruits of peach and pear. Formed in grapes and grape must by the action of Botrytis cinerea on galacturonic acid Acquisition and generation of the data is financially supported in part by CREST/JST. Mucic acid is an endogenous metabolite.
Iduronic acid
Iduronic acid is a constituent of glycosaminoglycans heparin and heparan sulfate in varying proportions providing considerable diversity in sequence and biological function. The glycosaminoglycans (GAGs) are linear polysaccharides with alternating uronic acids (Iduronic acid and Glucuronic acid) and hexosamine residues, in which a limited set of monosaccharide units gives rise to a number of complex sequences by variable substitution with O-sulfate, N-sulfate, and N-acetyl groups. GAGs usually exist as the O-linked side-chains of proteoglycans, displaying a set of physiological functions which is remarkably wide and as yet incompletely explored. They may act as structural components of connective tissue and the extracellular matrix, or as specific ligands in the relationship between the cell surface and its surroundings. Heparan sulfate exists on the surface of most or all mammalian cells and can display a remarkable range of different sequence motifs; its range of interactions and possible functions reflect its structural complexity. The main repeat unit of heparin structurally resembles the protein binding sequences in heparan sulfate, but contains a higher percentage of sulfated residues. Utilized therapeutically as an anticoagulant and readily available in good quantities heparin serves as a useful model for heparan sulfate. Theoretical and experimental studies indicate that L-Iduronic acid residues of glycosaminoglycans are in equilibrium of different conformations, the relative proportion of conformers being a function of sulfation pattern and sequence. This unique conformational flexibility may provide an explanation for the stronger binding and associated higher biological activities of Iduronic acid-containing glycosaminoglycans (such as heparin, heparan sulfate and dermatan sulfate) as compared with other GAGs having similar charge density but with the more rigid glucuronic acid as the major uronic acid residue. Dermatan sulfates and heparins, which contain L-Iduronic acid in their backbone, show higher low-density lipoprotein (LDL)-affinity than chondroitin sulfates, which contain only D-glucuronic acid. Though confirming a non-specific, predominantly electrostatic interaction between GAGs and LDL, these results indicate modulation of LDL affinity by the polysaccharide backbone. Naturally oversulfated dermatan sulfate (SO3H/COOH ca. 1.2), mainly oversulfated at C-2 of Iduronic acid residues, show comparatively higher anticoagulant activity. (PMID: 3076283, 8466951, 8542607, 11087707). Iduronic acid is a constituent of glycosaminoglycans heparin and heparan sulfate in varying proportions providing considerable diversity in sequence and biological function.
1-Methyl 2-galloylgalactarate
1-Methyl 2-galloylgalactarate is found in fruits. 1-Methyl 2-galloylgalactarate is a constituent of the fruit of emblic (Phyllanthus emblica). Constituent of the fruit of emblic (Phyllanthus emblica). 1-Methyl 2-galloylgalactarate is found in fruits.
2-O-Galloylgalactaric acid
2-O-Galloylgalactaric acid is found in fruits. 2-O-Galloylgalactaric acid is a constituent of the fruit of emblic (Phyllanthus emblica). Constituent of the fruit of emblic (Phyllanthus emblica). 2-Galloylgalactaric acid is found in fruits.
6-Methyl 2-galloylgalactarate
6-Methyl 2-galloylgalactarate is found in fruits. 6-Methyl 2-galloylgalactarate is a constituent of the fruit of emblic (Phyllanthus emblica). Constituent of the fruit of emblic (Phyllanthus emblica). 6-Methyl 2-galloylgalactarate is found in fruits.
Dimethyl 2-galloylgalactarate
Dimethyl 2-galloylgalactarate is found in fruits. Dimethyl 2-galloylgalactarate is a constituent of the fruit of emblic (Phyllanthus emblica). Constituent of the fruit of emblic (Phyllanthus emblica). Dimethyl 2-galloylgalactarate is found in fruits.
Pectic acid
Pectic acid is a water insoluble, transparent gelatinous acid existing in ripe fruit and some vegetables. Pectic acid exists in the cell walls of plant tissues, and these substances are ingested from vegetables, fruits, etc. Pectic substances are dealt with as dietary fibers, but other physiological functions are not clear. Pectic acid is degraded in the digestive tract of man and it is considered that digestion is by the action of intestinal bacteria. Pectic acid is mainly degraded to 4,5-unsaturated digalacturonic acid and perhaps to 4,5-unsaturated trigalacturonic acid, by the action of the enzymes from bacteria such as Bacteroides sp. and Clostridium sp. in the human digestive tract. Then, they are used as carbon sources by these pectic-acid-using bacteria. (PMID: 12111144). Present in cell walls of all plant tissues. Up to 30\\% w/w of this polysaccharide can be isolated from orange and lemon rind. It is used in food processing as a gelling agent, stabiliser, thickener and emusifier [DFC] D000074385 - Food Ingredients > D005503 - Food Additives > D010368 - Pectins
Pectin
Pectin, also known as galacturonate or D-lyxose, is a structural acidic heteropolysaccharide contained in the primary and middle lamella and cell walls of terrestrial plants. Its main component is galacturonic acid, a sugar acid derived from galactose. It was first isolated and described in 1825 by Henri Braconnot. It is produced commercially as a white to light brown powder, mainly extracted from citrus fruits, and is used in food as a gelling agent, particularly in jams and jellies. It is also used in dessert fillings, medicines, sweets, as a stabiliser in fruit juices and milk drinks, and as a source of dietary fibre. In plant biology, pectin consists of a complex set of polysaccharides (see below) that are present in most primary cell walls and are particularly abundant in the non-woody parts of terrestrial plants. Pectin is a major component of the middle lamella, where it helps to bind cells together, but is also found in primary cell walls. Pectin is deposited by exocytosis into the cell wall via vesicles produced in the golgi. Pectin is a natural part of the human diet, but does not contribute significantly to nutrition. The daily intake of pectin from fruits and vegetables can be estimated to be around 5g if approximately 500g of fruits and vegetables are consumed per day. Pectin is a heterosaccharide derived from the cell wall of plants. Pectins vary in their chain lengths, complexity and the order of each of the monosaccharide units. The characteristic structure of pectin is a linear chain of alpha(1-4)linked D-galacturonic acid that forms the pectin-backbone, a homogalacturonan. [HMDB] COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS
Losartan N2-glucuronide
Losartan N2-glucuronide is only found in individuals that have used or taken Losartan. Losartan N2-glucuronide is a metabolite of Losartan. Losartan n2-glucuronide belongs to the family of Pyranoid Amino Acids and Derivatives. These are compounds containing a (hydro)pyran ring bearing unprotected amino and carboxylic acid functionalities.
Alginic acid
Alginic acid, also referred to as algin or alginate, is a hydrophilic, anionic polysaccharide that occurs naturally in brown seaweeds (Laminaria sp., Macrocystis sp., Lessonia sp., and others). It is normally present on the cell walls and in the intracellular spaces of these seaweeds (PMID: 30000910). Alginate forms a viscous gel when mixed with water. It is mainly used as a thickener and stabilizer in foods, pharmaceuticals, and cosmetics. It has a unique ability to absorb and conform to small details making it ideal for creating dental impressions, hands, feet or other small-scale items. Alginate is also used as a thickening agent for soups, ice-cream, cosmetics, jellies, drinks and pharmaceutical preparations, including Gaviscon, which is used to inhibit acid reflux (PMID: 2258131, 231639, 4738939, 6483217, 13224336). Alginate is also used as a pharmaceutical ingredient to treat a variety of health conditions including diabetes, cholesterol, obesity, and digestive tract problems (PMID: 27738945, 6355904, 22054948). Its principal function in biomedical applications is as a hydrogel to treat wound healing and in tissue engineering (PMID: 23020277, 1724711, 31841826, 391598, 19235799, 30959985).
L-Altruronic acid
L-Altruronic acid is produced during pectin saponification, by epimerisation of
5-(3',4'-Dihydroxyphenyl)-gamma-valerolactone-3'-O-methyl-4'-O-glucuronide
5-(3,4-Dihydroxyphenyl)-gamma-valerolactone-3-O-methyl-4-O-glucuronide is a conjugate of 5-(3,4-dihydroxyphenyl)-gamma-valerolactone-3-O-methyl and glucuronide. A glucuronide, also known as glucuronoside, is any substance produced by linking glucuronic acid to another substance via a glycosidic bond. The glucuronides belong to the glycosides. (Wikipedia)
Zileuton O-glucuronide
Zileuton O-glucuronide is a metabolite of zileuton. Zileuton (trade name ZYFLO) is an orally active inhibitor of 5-lipoxygenase, and thus inhibits leukotrienes (LTB4, LTC4, LTD4, and LTE4) formation. Zileuton is used for the maintenance treatment of asthma. Zileuton was introduced in 1996 by Abbott Laboratories and is now marketed in two formulations by Cornerstone Therapeutics Inc. under the brand names ZYFLO and ZYFLO CR. The original immediate-release formulation of zileuton, known as ZYFLO, is taken four times per day. (Wikipedia)
Pyridine N-oxide glucuronide
C11H14NO7+ (272.07702340000003)
Pyridine N-oxide glucuronide is a metabolite of sorafenib. Sorafenib (co-developed and co-marketed by Bayer and Onyx Pharmaceuticals as Nexavar), is a drug approved for the treatment of primary kidney cancer and advanced primary liver cancer. (Wikipedia)
Aldehydo-L-iduronate
Aldehydo-L-iduronate is also known as aldehydo-L-Iduronic acid. Aldehydo-L-iduronate is considered to be soluble (in water) and acidic
(2R,3R,4R,5S,6S)-3,4,5,6-Tetrahydroxyoxane-2-carboxylic acid
Glucuronic acid sulfate
C6H10O10S (273.99946800000004)
Iduronate 2-sulfate
C6H10O10S (273.99946800000004)
Minoxidil Glucuronide
N-Hydroxymexiletine glucuronide
(2S,3S,4S,5R)-3,4,5-Trihydroxy-6-sulfooxyoxane-2-carboxylic acid
C6H10O10S (273.99946800000004)
Belinostat glucuronide
C21H22N2O10S (494.09951120000005)
4-O-Methylglucuronic acid
4-o-methylglucuronic acid belongs to glucuronic acid derivatives class of compounds. Those are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. 4-o-methylglucuronic acid is soluble (in water) and a weakly acidic compound (based on its pKa). 4-o-methylglucuronic acid can be found in cashew nut and european plum, which makes 4-o-methylglucuronic acid a potential biomarker for the consumption of these food products.
2-trans-O-Feruloylglucaric acid
2-trans-o-feruloylglucaric acid belongs to glucuronic acid derivatives class of compounds. Those are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. 2-trans-o-feruloylglucaric acid is slightly soluble (in water) and a moderately acidic compound (based on its pKa). 2-trans-o-feruloylglucaric acid can be found in sweet orange, which makes 2-trans-o-feruloylglucaric acid a potential biomarker for the consumption of this food product.
Mannuronic acid
Mannuronic acid, also known as mannuronate, belongs to glucuronic acid derivatives class of compounds. Those are compounds containing a glucuronic acid moiety (or a derivative), which consists of a glucose moiety with the C6 carbon oxidized to a carboxylic acid. Mannuronic acid is soluble (in water) and a weakly acidic compound (based on its pKa). Mannuronic acid can be found in flaxseed, which makes mannuronic acid a potential biomarker for the consumption of this food product.
Sodium alginate
Stabiliser, emulsifier, thickener, formulation aid [DFC]. The chemical compound sodium alginate is the sodium salt of alginic acid. Sodium alginate is a gum, extracted from the cell walls of brown algae. As a flavorless gum, it is used by the foods industry to increase viscosity and as an emulsifier. As a food additive, sodium alginate is used especially in the production of gel-like foods. For example, bakers Chellies are often gelled alginate jam. [Wikipedia] Stabiliser, emulsifier, thickener, formulation aid [DFC]
Calcium galactarate
Potential cause of turbidity in mucic acid rich wines. Calcium galactarate is found in alcoholic beverages.
alpha-D-glucuronate 1-phosphate
alpha-d-glucuronate 1-phosphate is also known as alpha-D-glucuronic acid 1-phosphoric acid. alpha-d-glucuronate 1-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). alpha-d-glucuronate 1-phosphate can be found in a number of food items such as lingonberry, tronchuda cabbage, eggplant, and medlar, which makes alpha-d-glucuronate 1-phosphate a potential biomarker for the consumption of these food products.