Classification Term: 3726

Sugar acids and derivatives (ontology term: CHEMONTID:0000215)

Compounds containing a saccharide unit which bears a carboxylic acid group." []

found 51 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Carbohydrates and carbohydrate conjugates

Child Taxonomies: Sugar amino acids and derivatives, Glucuronic acid derivatives

2,3-Diphosphoglyceric acid

2,3-DIPHOSPHO-D-GLYCERIC ACID PENTASODIUM SALT

C3H8O10P2 (265.9592728)


2,3-Bisphosphoglycerate (2,3-BPG, also known as 2,3-diphosphoglycerate or 2,3-DPG) is a three carbon isomer of the glycolytic intermediate 1,3-bisphosphoglycerate and is present at high levels in the human red blood cell (RBC; erythrocyte)--at the same molar concentration as hemoglobin. It is notable because it binds to deoxygenated hemoglobin in RBCs. In doing so, it allosterically upregulates the ability of RBCs to release oxygen near tissues that need it most. Its function was discovered in 1967 by Reinhold Benesch and Ruth Benesch. [HMDB] 2,3-Bisphosphoglycerate (CAS: 138-81-8), also known as 2,3-BPG or 2,3-diphosphoglycerate, is a three-carbon isomer of the glycolytic intermediate 1,3-bisphosphoglycerate and is present at high levels in the human red blood cell (RBC; erythrocyte) at the same molar concentration as hemoglobin. It is notable because it binds to deoxygenated hemoglobin in RBCs. In doing so, it allosterically upregulates the ability of RBCs to release oxygen near tissues that need it most. Its function was discovered in 1967 by Reinhold Benesch and Ruth Benesch. KEIO_ID D017

   

D-Glycerate 3-phosphate

(2R)-2-Hydroxy-3-(phosphonatooxy)propanoic acid

C3H7O7P (185.9929402)


3-phospho-d-glyceric acid, also known as 3-phosphoglycerate or D-glycerate 3-phosphate, belongs to sugar acids and derivatives class of compounds. Those are compounds containing a saccharide unit which bears a carboxylic acid group. 3-phospho-d-glyceric acid is soluble (in water) and a moderately acidic compound (based on its pKa). 3-phospho-d-glyceric acid can be found in a number of food items such as towel gourd, orange mint, guava, and mulberry, which makes 3-phospho-d-glyceric acid a potential biomarker for the consumption of these food products. 3-phospho-d-glyceric acid can be found primarily in saliva. 3-phospho-d-glyceric acid exists in all living species, ranging from bacteria to humans. (2R)-2-Hydroxy-3-(phosphonatooxy)propanoate, also known as 3-phospho-(R)-glycerate or D-glycerate 3-phosphate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group (2R)-2-Hydroxy-3-(phosphonatooxy)propanoate is a drug (2R)-2-hydroxy-3-(phosphonatooxy)propanoate has been detected, but not quantified, in several different foods, such as poppies, small-leaf lindens, lupines, pomegranates, and kombus. These are compounds containing a saccharide unit which bears a carboxylic acid group.

   

Glycerate

(2R)-2,3-dihydroxypropanoic acid

C3H6O4 (106.0266076)


Glyceric acid is a colourless syrupy acid, obtained from oxidation of glycerol. It is a compound that is secreted excessively in the urine by patients suffering from D-glyceric aciduria, an inborn error of metabolism, and D-glycerate anemia. Deficiency of human glycerate kinase leads to D-glycerate acidemia/D-glyceric aciduria. Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive, and metabolic acidosis. At sufficiently high levels, glyceric acid can act as an acidogen and a metabotoxin. An acidogen is an acidic compound that induces acidosis, which has multiple adverse effects on many organ systems. A metabotoxin is an endogenously produced metabolite that causes adverse health effects at chronically high levels. Glyceric acid is an organic acid. Abnormally high levels of organic acids in the blood (organic acidemia), urine (organic aciduria), the brain, and other tissues lead to general metabolic 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 abnormalities, seizures, coma, and possibly death. These are also the characteristic symptoms of untreated glyceric aciduria. Many affected children with organic acidemias experience intellectual disability or delayed development. In adults, acidosis or acidemia is characterized by headaches, confusion, feeling tired, tremors, sleepiness, and seizures. Elevated values may also be due to microbial sources such as yeast (Aspergillus, Penicillium, probably Candida) or due to dietary sources containing glycerol (glycerine). Glyceric acid is isolated from various plants (e.g. brassicas, pulses, and Vicia faba). A colorless syrupy acid, obtained from oxidation of glycerol. It is a compound that is secreted excessively in the urine by patients suffering from D-glyceric aciduria and D-glycerate anemia. Deficiency of human glycerate kinase leads to D-glycerate acidemia/D-glyceric aciduria. Symptoms of the disease include progressive neurological impairment, hypotonia, seizures, failure to thrive and metabolic acidosis.; Glyceric acid is a natural three-carbon sugar acid. Salts and esters of glyceric acid are known as glycerates. Glyceric acid is found in many foods, some of which are peanut, common grape, garden tomato (variety), and french plantain. Glyceric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=473-81-4 (retrieved 2024-06-29) (CAS RN: 473-81-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Muramic acid

(2R)-2-{[(2R,3R,4S,5S,6R)-3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

C9H17NO7 (251.1004972)


Muramic acid is an amino sugar acid. In terms of chemical composition, it is the ether of lactic acid and glucosamine. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls. Muramic acid, also known as muramate or murexide, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Muramic acid is an amino sugar acid. It occurs naturally as N-acetylmuramic acid in peptidoglycan, whose primary function is a structural component of many typical bacterial cell walls. In terms of chemical composition, it is the ether of lactic acid and glucosamine. Muramic acid is a marker of bacterial peptidoglycan, in environmental and clinical specimens. (PMID: 10778926) [HMDB] Muramic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=1114-41-6 (retrieved 2024-07-01) (CAS RN: 1114-41-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

Gluconic acid

(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoic acid

C6H12O7 (196.0583002)


Gluconic acid, also known as D-gluconic acid, D-gluconate or (2R,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanoic acid (also named dextronic acid), is the C1-oxidized form of D-glucose where the aldehyde group has become oxidized to the corresponding carboxylic acid. Gluconic acid belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. In aqueous solution, gluconic acid exists in equilibrium with the cyclic ester glucono delta-lactone. Gluconic acid occurs naturally in fruit, honey, kombucha tea and wine. The salts of gluconic acid are known as "gluconates". Gluconic acid, gluconate salts, and gluconate esters occur widely in nature because such species arise from the oxidation of glucose. Gluconic acid exists in all living species, ranging from bacteria to plants to humans. The metabolism of gluconate is well characterized in prokaryotes where it is known to be degraded following phosphorylation by gluconokinase. Glucokinase activity has also been detected in mammals, including humans (PMID: 24896608). Gluconic acid is produced in the gluconate shunt pathway. In the gluconate shunt, glucose is oxidized by glucose dehydrogenase (also called glucose oxidase) to furnish gluconate, the form in which D-gluconic acid is present at physiological pH. Subsequently, gluconate is phosphorylated by the action of gluconate kinase to produce 6-phosphogluconate, which is the second intermediate of the pentose phosphate pathway. This gluconate shunt is mainly found in plants, algae, cyanobacteria and some bacteria, which all use the Entner–Doudoroff pathway to degrade glucose or gluconate; this generates 2-keto-3-deoxygluconate-6-phosphate, which is then cleaved to generate pyruvate and glyceraldehyde 3-phosphate. Glucose dehydrogenase and gluconate kinase activities are also present in mammals, fission yeast, and flies. Gluconic acid has many industrial uses. It is used as a drug as part of electrolyte supplementation in total parenteral nutrition. It is also used in cleaning products where it helps cleaning up mineral deposits. Gluconic acid or Gluconic acid is used to maintain the cation-anion balance on electrolyte solutions. In humans, gluconic acid is involved in the metabolic disorder called the transaldolase deficiency. Gluconic acid has been found to be a metabolite in Aspergillus (Hugo Vanden Bossche, D.W.R. Mackenzie and G. Cauwenbergh. Aspergillus and Aspergillosis, 1987). [Spectral] D-Gluconic acid (exact mass = 196.0583) and Guanine (exact mass = 151.04941) were not completely separated on HPLC under the present analytical conditions as described in AC$XXX. Additionally some of the peaks in this data contains dimers and other unidentified ions. Dietary supplement, acidity regulator approved in Japan. Component of bottle rinsing formulations Acquisition and generation of the data is financially supported in part by CREST/JST. KEIO_ID G031

   

D-Tartaric acid

L-(+)-Tartaric acid

C4H6O6 (150.01643760000002)


DL-Tartaric acid is a non-racemic mixture of L- and D-tartaric acids with antioxidant activities[1][2].

   

Threonic acid

2,3,4-Trihydroxy-(threo)-butanoic acid

C4H8O5 (136.0371718)


Threonic acid, also known as threonate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. Threonic acid is a sugar acid derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). One study suggested that because L-threonate inhibits DKK1 expression in vitro, it may have potential in the treatment of androgenic alopecia (PMID:21034532). Threonic acid is probably derived from glycated proteins or from degradation of ascorbic acid. It is a normal component in aqueous humour and blood (PMID:10420182). Threonic acid is a substrate of L-threonate 3-dehydrogenase (EC 1.1.1.129) in the ascorbate and aldarate metabolism pathway (KEGG). It has been found to be a microbial metabolite (PMID:20615997). L-threonic acid, also known as L-threonate or L-threonic acid magnesium salt, belongs to sugar acids and derivatives class of compounds. Those are compounds containing a saccharide unit which bears a carboxylic acid group. L-threonic acid is soluble (in water) and a weakly acidic compound (based on its pKa). L-threonic acid can be found in a number of food items such as buffalo currant, yam, purslane, and bayberry, which makes L-threonic acid a potential biomarker for the consumption of these food products. L-threonic acid can be found primarily in blood. Threonic acid is a sugar acid derived from threose. The L-isomer is a metabolite of ascorbic acid (vitamin C). One study suggested that because L-threonate inhibits DKK1 expression in vitro, it may have potential in treatment of androgenic alopecia .

   

2-Keto-L-gluconate

(3S,4S,5R)-3,4,5,6-tetrahydroxy-2-oxohexanoic acid

C6H10O7 (194.042651)


2-Keto-L-gluconate is a derivative of gluconic acid, which occurs naturally in fruit, honey and wine and is used as a food additive, an acidity regulator. It is also used in cleaning products where it helps cleaning up mineral deposits. It is a strong chelating agent, especially in alkaline solution. It chelates the anions of calcium, iron, aluminium, copper, and other heavy metals. [HMDB] 2-Keto-L-gluconate is a derivative of gluconic acid, which occurs naturally in fruit, honey and wine and is used as a food additive, an acidity regulator. It is also used in cleaning products where it helps cleaning up mineral deposits. It is a strong chelating agent, especially in alkaline solution. It chelates the anions of calcium, iron, aluminium, copper, and other heavy metals.

   

2-Phospho-D-glyceric acid

(2R)-3-Hydroxy-2-(phosphonooxy)propanoic acid

C3H7O7P (185.9929402)


2-Phosphoglyceric acid (2PG), or 2-phosphoglycerate, is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate.; 2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site. (PMID: 8994873, Wikipedia). 2-Phosphoglycerate is found in rice. 2-Phospho-D-glycerate or 2PG is an intermediate in gluconeogenesis. It is a glyceric acid which serves as the substrate in the ninth step of glycolysis. 2PG is converted by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. More specifically, 2PG can be generated from Glycerate-3-phosphate via phosphoglycerate mutase or from phosphoenolpyrvate via alpha enolase. KEIO_ID P029

   

D-Xylonic acid

(2R,3S,4R)-2,3,4,5-tetrahydroxypentanoic acid

C5H10O6 (166.04773600000001)


D-​Xylonic acid belongs to the family of hydroxy fatty acids. These are fatty acids in which the chain bears an hydroxyl group. ​D-​Xylonic acid has been identified in the human placenta (PMID: 32033212).

   

3-Dehydro-L-gulonate

(2S,4R,5S)-2,4,5,6-tetrahydroxy-3-oxohexanoic acid

C6H10O7 (194.042651)


3-Dehydro-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 3-Dehydro-L-gulonate is the 4th to last step in the synthesis of D-Xylulose 5-phosphate and is converted from 2,3-Diketo-L-gulonate via the enzyme 3-dehydro-L-gulonate 2-dehydrogenase (EC 1.1.1.130). It is then converted to 3-Dehydro-L-gulonate 6-phosphate via the enzyme L-xylulokinase (EC 2.7.1.53). [HMDB] 3-Dehydro-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 3-Dehydro-L-gulonate is the 4th to last step in the synthesis of D-Xylulose 5-phosphate and is converted from 2,3-Diketo-L-gulonate via the enzyme 3-dehydro-L-gulonate 2-dehydrogenase (EC 1.1.1.130). It is then converted to 3-Dehydro-L-gulonate 6-phosphate via the enzyme L-xylulokinase (EC 2.7.1.53).

   

3-deoxy-D-manno-octulosonate

(4R,5R,6R,7R)-4,5,6,7,8-pentahydroxy-2-oxooctanoic acid

C8H14O8 (238.0688644)


3-deoxy-d-manno-octulosonate, also known as kdo or 2-dehydro-3-deoxy-D-octonate, belongs to sugar acids and derivatives class of compounds. Those are compounds containing a saccharide unit which bears a carboxylic acid group. 3-deoxy-d-manno-octulosonate is soluble (in water) and a moderately acidic compound (based on its pKa). 3-deoxy-d-manno-octulosonate can be found in a number of food items such as peppermint, okra, horseradish tree, and hazelnut, which makes 3-deoxy-d-manno-octulosonate a potential biomarker for the consumption of these food products. 3-deoxy-d-manno-octulosonate may be a unique E.coli metabolite.

   

Diketogulonic acid

(4R,5S)-2,3-Dioxo-4,5,6-trihydroxyhexanoic acid

C6H8O7 (192.0270018)


Diketogulonic acid (DKG) is a metabolite of the degradation of vitamin C, the nonenzymatic hydrolysis-product of dehydroascorbate. Dehydroascorbate can be reduced back to ascorbate or hydrolyzed to DKG; the latter reaction is irreversible and DKG is devoid of antiscorbutic activity. The degradation pathway of vitamin C continues to produce l-erythrulose and oxalate as final products. DKG appears in human urine and represents approximately 20\\% of the vitamin C by-products (oxalate being approximately 44\\% and dehydroascorbate 20\\%). A major catabolic event in man is the cleavage of the molecule (presumably a spontaneous cleavage of DKG) between C2 and C3, with little if any decarboxylation. The oxalate formed in this way may contribute to the formation of kidney stones in susceptible individuals. However, the association between ascorbate supplementation and increased risk of kidney stone formation remains a matter of controversy. (PMID: 16698813, 17222174)

   

Arabonate/xylonate

(2S,3R,4R)-2,3,4,5-tetrahydroxypentanoic acid

C5H10O6 (166.047736)


Arabinonic acid (CAS: 13752-83-5) is a substrate of L-arabinonate dehydratase [EC 4.2.1.25] in the pathway ascorbate and aldarate metabolism (KEGG). Arabinonic acid is a substrate of L-arabinonate dehydratase [EC 4.2.1.25] in pathway ascorbate and aldarate metabolism. (KEGG) [HMDB]

   

3-phosphoglycerate

3-(Dihydrogen phosphoric acid)glyceric acid

C3H7O7P (185.9929402)


3-Phosphoglyceric acid, also known as 3PG, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 3PG is the conjugate acid of glycerate 3-phosphate (GP or G3P). It is a solid that is soluble in water. 3-Phosphoglyceric acid exists in all living species, ranging from bacteria to humans. The glycerate is a biochemically significant metabolic intermediate in both glycolysis and the Calvin cycle. This is the first compound formed during the C3 or Calvin cycle. Glycerate 3-phosphate is also a precursor for serine, which, in turn, can create cysteine and glycine through the homocysteine cycle. Within humans, 3-phosphoglyceric acid participates in a number of enzymatic reactions. In particular, 3-phosphoglyceric acid can be biosynthesized from glyceric acid 1,3-biphosphate, which is mediated by the enzyme phosphoglycerate kinase 1. In addition, 3PG can be converted into 2-phospho-D-glyceric acid, which is catalyzed by the enzyme phosphoglycerate mutase 2. 3-phosphoglyceric acid is involved in the Warburg effect (aerobic glycolysis), a metabolic shift that is a hallmark of cancer (PMID: 29362480). 3-phosphoglyceric acid (3PG) is a 3-carbon molecule that is a metabolic intermediate in both glycolysis and the Calvin cycle. This chemical is often termed PGA when referring to the Calvin cycle. In the Calvin cycle, two glycerate 3-phosphate molecules are reduced to form two molecules of glyceraldehyde 3-phosphate (GALP). (wikipedia) [HMDB] KEIO_ID P028

   

Ribonic acid

(2R,3R,4R)-2,3,4,5-tetrahydroxypentanoic acid

C5H10O6 (166.04773600000001)


Ribonic acid (CAS: 17812-24-7) is a product of the enzyme ribose 1-dehydrogenase (NADP+) [EC 1.1.1.115] (KEGG). Ribonic acid is a product of the enzyme ribose 1-dehydrogenase (NADP+) [EC 1.1.1.115] (KEGG). [HMDB]

   

Tartaric acid

(2R,3R)-2,3-dihydroxybutanedioic acid

C4H6O6 (150.0164376)


Tartaric acid is a white crystalline organic acid. It occurs naturally in many plants, particularly grapes and tamarinds, and is one of the main acids found in wine. It is added to other foods to give a sour taste, and is used as an antioxidant. Salts of tartaric acid are known as tartrates. It is a dihydroxy derivative of dicarboxylic acid. Tartaric acid is a muscle toxin, which works by inhibiting the production of malic acid, and in high doses causes paralysis and death. The minimum recorded fatal dose for a human is about 12 grams. In spite of that, it is included in many foods, especially sour-tasting sweets. As a food additive, tartaric acid is used as an antioxidant with E number E334, tartrates are other additives serving as antioxidants or emulsifiers. Naturally-occurring tartaric acid is chiral, meaning that it has molecules that are non-superimposable on their mirror-images. It is a useful raw material in organic chemistry for the synthesis of other chiral molecules. The naturally occurring form of the acid is L-(+)-tartaric acid or dextrotartaric acid. The mirror-image (enantiomeric) form, levotartaric acid or D-(-)-tartaric acid, and the achiral form, mesotartaric acid, can be made artificially. Tartarate is believed to play a role in inhibiting kidney stone formation. Most tartarate that is consumed by humans is metabolized by bacteria in the gastrointestinal tract -- primarily in the large instestine. Only about 15-20\\\\\\% of consumed tartaric acid is secreted in the urine unchanged. Tartaric acid is a biomarker for the consumption of wine and grapes (PMID:24507823). Tartaric acid is also a fungal metabolite, elevated levels in the urine (especially in children) may be due to the presence of yeast (in the gut or bladder). It can be produced by Agrobacterium, Nocardia, Rhizobium, Saccharomyces as well (PMID:7628083) (https://link.springer.com/article/10.1023/A:1005592104426). High levels of tartaric acid have been found in autistic children. In adults, tartaric acid may be due to the consumption of wine (https://www.greatplainslaboratory.com/articles-1/2015/11/13/candida-and-overgrowth-the-problem-bacteria-by-products) (PMID:15738524; PMID:24507823; PMID:7628083). Present in many fruits, wines and coffee. Acidulant for beverages, foods and pharmaceuticals,used to enhance natural and synthetic fruit flavours, especies in grape- and lime-flavoured drinks and candies. Firming agent, humectant. It is used in leavening systems including baking powders. Stabiliising agent for ground spices and cheeses to prevent discoloration. Chelating agent in fatty foods. Synergist with antioxidants, pH control agent in milk, jams and jellies, moisture-control agent. *Metatartaric* acid (a mixture of polyesters obtained by the controlled dehydration of (+)-tartaric acid, together with unchanged (+)-tartaric acid) is permitted in wine in UK (+)-Tartaric acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=87-69-4 (retrieved 2024-07-01) (CAS RN: 87-69-4). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0). DL-Tartaric acid is a non-racemic mixture of L- and D-tartaric acids with antioxidant activities[1][2]. L-Tartaric acid (L-(+)-Tartaric acid) is an endogenous metabolite. L-Tartaric acid is the primary nonfermentable soluble acid in grapes and the principal acid in wine. L-Tartaric acid can be used as a flavorant and antioxidant for a range of foods and beverages[1]. L-Tartaric acid (L-(+)-Tartaric acid) is an endogenous metabolite. L-Tartaric acid is the primary nonfermentable soluble acid in grapes and the principal acid in wine. L-Tartaric acid can be used as a flavorant and antioxidant for a range of foods and beverages[1].

   

2,3-Diketo-L-gulonate

(4R,5S)-4,5,6-Trihydroxy-2,3-dioxohexanoic acid

C6H8O7 (192.0270018)


2,3-Diketo-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 2,3-Diketo-L-gulonate is produced from Dehydroascorbate and then converted to L-Xylonate via the enzyme Lyases (EC 4.1.1.-). [HMDB] 2,3-Diketo-L-gulonate is an intermediate in Ascorbate and aldarate metabolism. 2,3-Diketo-L-gulonate is produced from Dehydroascorbate and then converted to L-Xylonate via the enzyme Lyases (EC 4.1.1.-). COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

L-Lyxonic acid

(2R,3R,4S)-2,3,4,5-tetrahydroxypentanoic acid

C5H10O6 (166.04773600000001)


L-​Lyxonic acid belongs to the family of sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.

   

L-Xylonic acid

(2S,3R,4S)-2,3,4,5-tetrahydroxypentanoic acid

C5H10O6 (166.04773600000001)


L-Xylonic acid belongs to the family of sugar acids and derivatives. These are compounds containing a saccharide unit which bears a carboxylic acid group.

   

Erythronic acid

(R*,r*)-2,3,4-trihydroxy-butanoic acid

C4H8O5 (136.0371718)


Erythronic acid is a sugar component of aqueous humour (eye). It may be derived from glycated proteins or from degradation of ascorbic acid. Erythronic acid is a normal organic acid present in a healthy adult and pediatric population. It has been found in urine, plasma, CSF, and synovial fluid (PMID: 14708889, 8087979, 8376520, 10420182). Erythronic acid is formed when N-acetyl-D-glucosamine (GlcNAc) is oxidized. GlcNAc is a constituent of hyaluronic acid (HA), a polysaccharide consisting of alternating units of glucuronic acid and GlcNAc, present as an aqueous solution in synovial fluid. In the synovial fluid of patients suffering from rheumatoid arthritis, HA is thought to be degraded either by radicals generated by Fenton chemistry (Fe2+/H2O2) or by NaOCl generated by myeloperoxidase (PMID: 10614067). Erythronic acid is a sugar component of aqueous humour (eye). It may be derived from glycated proteins or from degradation of ascorbic acid. Erythronic acid is a normal organic acid present in a healthy adult and pediatric population. It has been found in urine, plasma, CSF and synovial fluid. (PMID: 14708889, 8087979, 8376520, 10420182) Erythronic acid. CAS Common Chemistry. CAS, a division of the American Chemical Society, n.d. https://commonchemistry.cas.org/detail?cas_rn=13752-84-6 (retrieved 2024-07-10) (CAS RN: 13752-84-6). Licensed under the Attribution-Noncommercial 4.0 International License (CC BY-NC 4.0).

   

2-Phosphoglyceric acid

3-Hydroxy-2-(phosphonooxy)propanoic acid

C3H7O7P (185.9929402)


2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site. (PMID: 8994873, Wikipedia) [HMDB] 2-Phosphoglyceric acid (2PGA) is a glyceric acid which serves as the substrate in the ninth step of glycolysis. It is catalyzed by enolase into phosphoenolpyruvate (PEP), the penultimate step in the conversion of glucose to pyruvate. Enolase catalyzes the beta-elimination reaction in a stepwise manner wherein OH- is eliminated from C3 of a discrete carbanion (enolate) intermediate. This intermediate is created by removal of the proton from C2 of 2PGA by a base in the active site (PMID: 8994873, Wikipedia).

   

Sambucus nigra Degraded cyanogenic glycosides (2'-Epimer)

Methyl 3-[(S)-cyano(phenyl)methoxy]-2-hydroxy-3-[(3-hydroxy-1-methoxy-1-oxopropan-2-yl)oxy]propanoic acid

C16H19NO8 (353.1110614)


Sambucus nigra Degraded cyanogenic glycosides (2-Epimer) is found in fruits. Sambucus nigra Degraded cyanogenic glycosides (2-Epimer) is isolated from Sambucus nigra (elderberry Isolated from Sambucus nigra (elderberry). Sambucus nigra Degraded cyanogenic glycosides (2-Epimer) is found in fruits.

   

2,3,4,5,6,7-Hexahydroxyheptanoic acid

(3R,4S,5R,6R)-2,3,4,5,6,7-hexahydroxyheptanoic acid

C7H14O8 (226.0688644)


2,3,4,5,6,7-Hexahydroxyheptanoic acid, also known as (2XI)-D-glycero-D-gulo-heptonic acid or (2XI)-D-gluco-heptonate, belongs to the class of organic compounds known as sugar acids and derivatives. Sugar acids and derivatives are compounds containing a saccharide unit which bears a carboxylic acid group. 2,3,4,5,6,7-Hexahydroxyheptanoic acid is soluble (in water) and a weakly acidic compound (based on its pKa).

   

3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid

(4S,5R,6R,7R,8S)-4,5,6,7,8,9-hexahydroxy-2-oxononanoic acid

C9H16O9 (268.0794286)


3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) is a sialic acid (Sia) that is ubiquitously expressed in vertebrates during normal development and tumorigenesis. Its expression is thought to be regulated by multiple biosynthetic steps catalyzed by several enzymes, including CMP-Sia synthetase. (PMID 11479279) Sialic acids are frequently the terminal sugars on secreted and cell surface glycoproteins and glycolipids, and their presence can have considerable influence on the biological properties of a cell. For example, the temporal appearance and disappearance of polysialic polymers has been intimately linked with the proper development of neural tissues during embryogenesis. In pathogenic diseases, including meningitis and gastric inflammation, particular microbes recognize cell surface sialic acids when invading host cells. Sialic acid residues can also mask recognition sites such as galactose residues on glycoproteins to prevent their in vivo removal by asialoglycoprotein receptors. In certain cancers, changes in sialic acid amounts, types, and linkages have been associated with tumorogenesis and cancer metastasis. (PMID 10749855) [HMDB] 3-Deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) is a sialic acid (Sia) that is ubiquitously expressed in vertebrates during normal development and tumorigenesis. Its expression is thought to be regulated by multiple biosynthetic steps catalyzed by several enzymes, including CMP-Sia synthetase. (PMID 11479279) Sialic acids are frequently the terminal sugars on secreted and cell surface glycoproteins and glycolipids, and their presence can have considerable influence on the biological properties of a cell. For example, the temporal appearance and disappearance of polysialic polymers has been intimately linked with the proper development of neural tissues during embryogenesis. In pathogenic diseases, including meningitis and gastric inflammation, particular microbes recognize cell surface sialic acids when invading host cells. Sialic acid residues can also mask recognition sites such as galactose residues on glycoproteins to prevent their in vivo removal by asialoglycoprotein receptors. In certain cancers, changes in sialic acid amounts, types, and linkages have been associated with tumorogenesis and cancer metastasis. (PMID 10749855).

   

4-Deoxyerythronic acid

(+/-)-erythro-2,3-dihydroxybutyric acid

C4H8O4 (120.0422568)


4-Deoxyerythronic acid is a normal organic acid present in human biofluids (PMIDs 2338430, 3829393, 3525594, 14708889, 1560100, 6725493), derived presumably from L-threonine. (PMID 2947647) It has been associated with uremia (PMID 1149237) and diabetes mellitus type 1. (PMID 2947647) [HMDB] 4-Deoxyerythronic acid is a normal organic acid present in human biofluids (PMIDs 2338430, 3829393, 3525594, 14708889, 1560100, 6725493), derived presumably from L-threonine. (PMID 2947647) It has been associated with uremia (PMID 1149237) and diabetes mellitus type 1. (PMID 2947647).

   

4-Deoxythreonic acid

(2R,3S)-Rel-2,3-dihydroxy--butanoic acid

C4H8O4 (120.0422568)


4-Deoxythreonic acid is a normally occurring carboxylic acid in human. (PMID: 3829393, 6725493). Metabolic profiling of urinary organic acids from patients with juvenile-onset (Type 1) diabetes mellitus have revealed significantly elevated levels of 4-deoxythreonic acid. (PMID: 2947647). The normal urinary constituent 4-deoxythreonic acid was found to diminish in urine incubated with E. coli. (PMID: 3910670). 4-Deoxythreonic acid is a normally occurring carboxylic acid in human. (PMID: 3829393, 6725493)

   

Glycerate

(2S)-2,3-Dihydroxy-propanoic acid

C3H6O4 (106.0266076)


L-glyceric acid is a human urinary metabolite present in patients with L-Glyceric aciduria. The formation of L-glyceric acid from accumulated hydroxypyruvate is due to deficiency of human glyoxylate reductase/hydroxypyruvate reductase (GRHPR, EC 1.1.1.81), a D-2-hydroxy-acid dehydrogenase that plays a critical role in the removal of the metabolic by-product glyoxylate from within the liver. Deficiency of this enzyme is the underlying cause of primary hyperoxaluria type 2 (PH2) and leads to increased urinary oxalate levels, formation of kidney stones and renal failure. (PMID: 16756993) [HMDB] L-glyceric acid is a human urinary metabolite present in patients with L-Glyceric aciduria. The formation of L-glyceric acid from accumulated hydroxypyruvate is due to deficiency of human glyoxylate reductase/hydroxypyruvate reductase (GRHPR, EC 1.1.1.81), a D-2-hydroxy-acid dehydrogenase that plays a critical role in the removal of the metabolic by-product glyoxylate from within the liver. Deficiency of this enzyme is the underlying cause of primary hyperoxaluria type 2 (PH2) and leads to increased urinary oxalate levels, formation of kidney stones and renal failure. (PMID: 16756993).

   

3-carboxy-2,3-dihydroxypropanoate

(R*,r*)-(+-)-2,3-dihydroxybutanedioic acid, monoammonium monosodium salt

C4H6O6 (150.01643760000002)


3-carboxy-2,3-dihydroxypropanoate is classified as a sugar acid or a Sugar acid derivative. Sugar acids are compounds containing a saccharide unit which bears a carboxylic acid group. 3-carboxy-2,3-dihydroxypropanoate is considered to be soluble (in water) and acidic L-Tartaric acid (L-(+)-Tartaric acid) is an endogenous metabolite. L-Tartaric acid is the primary nonfermentable soluble acid in grapes and the principal acid in wine. L-Tartaric acid can be used as a flavorant and antioxidant for a range of foods and beverages[1]. L-Tartaric acid (L-(+)-Tartaric acid) is an endogenous metabolite. L-Tartaric acid is the primary nonfermentable soluble acid in grapes and the principal acid in wine. L-Tartaric acid can be used as a flavorant and antioxidant for a range of foods and beverages[1].

   

3'-phosphonato-5'-adenylyl Sulfate(4-)

[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]sulfonic acid

C10H15N5O13P2S (506.98623200000003)


3-phosphonato-5-adenylyl Sulfate(4-) is also known as 3-Phosphonatoadenosine 5-phosphosulfate or PAPS. 3-phosphonato-5-adenylyl Sulfate(4-) is considered to be slightly soluble (in water) and acidic. 3-phosphonato-5-adenylyl Sulfate(4-) can be found throughout numerous foods such as Pigeon pea, New Zealand spinachs, White lupines, and Allspices

   

2,3-diketogulonate

4,5,6-trihydroxy-2,3-dioxohexanoic acid

C6H8O7 (192.0270018)


2,3-diketogulonate is also known as 2,3-dioxo-L-Gulonic. 2,3-diketogulonate is considered to be soluble (in water) and acidic

   

D-Xylonate

(2R,3S,4R)-2,3,4,5-tetrahydroxypentanoate

C5H9O6- (165.0399114)


   

L-Xylonate

(2S,3R,4S)-2,3,4,5-tetrahydroxypentanoate

C5H9O6- (165.0399114)


   

Keto-3-deoxy-D-manno-octulosonic acid

Ion(1-),(D)-isomer OF 2-keto-3-deoxyoctonate

C8H14O8 (238.0688644)


   

2,3-Dihydroxybutanoic acid

2,3-Dihydroxybutanoic acid

C4H8O4 (120.0422568)


   

2,3,4-Trihydroxybutanoic acid

2,3,4-trihydroxybutanoic acid

C4H8O5 (136.0371718)


   

3-Diphosphoglyceric acid

2,3-dihydroxy-3,3-diphosphopropanoic acid

C3H4O8P2 (229.93814440000003)


   

alpha-Muramic acid

2-{[3-amino-2,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy}propanoic acid

C9H17NO7 (251.1004972)


   

Daumone

(-)-6-(3,5-Dihydroxy-6-methyltetrahydropyran-2-yloxy) heptanoic acid

C13H24O6 (276.1572804)


   

Fructose lactate

3,4,5,6-Tetrahydroxy-6-(hydroxymethyl)oxan-2-yl 2-hydroxypropanoic acid

C9H16O9 (268.0794286)


   

galactose lactate

2,3,4,5-tetrahydroxy-6-(hydroxymethyl)oxan-2-yl 2-hydroxypropanoate

C9H16O9 (268.0794286)


   

Glucoheptonic acid

2,3,4,5,6,7-hexahydroxyheptanoic acid

C7H14O8 (226.0688644)


   

Glycerylmonooleate

2,3-dihydroxypropanoyl octadec-9-enoate

C21H38O5 (370.2719098)


   

monoacetone

2,3-dihydroxypropanoyl acetate

C5H8O5 (148.0371718)


   

3-Carboxyoxy-2-hydroxypropanoic acid

3-(carboxyoxy)-2-hydroxypropanoic acid

C4H6O6 (150.01643760000002)


   

sorbitol lactate

1,2,3,4,5,6-Hexahydroxyhexyl 2-hydroxypropanoic acid

C9H18O9 (270.0950778)


   

Aceneuramic acid

4,6,7,8,9-Pentahydroxy-5-[(1-hydroxyethylidene)amino]-2-oxononanoate

C11H19NO9 (309.10597640000003)


   

Sodium glucoheptonate

Sodium (3R,4S,5R,6R)-2,3,4,5,6,7-hexahydroxyheptanoic acid

C7H13NaO8 (248.05080980000002)


It is used as a food additive .

   

2,3-dioxo-L-gulonate

4,5,6-trihydroxy-2,3-dioxohexanoic acid

C6H7O7- (191.0191772)


2,3-dioxo-l-gulonate belongs to sugar acids and derivatives class of compounds. Those are compounds containing a saccharide unit which bears a carboxylic acid group. 2,3-dioxo-l-gulonate is soluble (in water) and a moderately acidic compound (based on its pKa). 2,3-dioxo-l-gulonate can be found in a number of food items such as gram bean, oriental wheat, agave, and horseradish, which makes 2,3-dioxo-l-gulonate a potential biomarker for the consumption of these food products.

   

2-carboxy-L-xylonolactone

3,4-Dihydroxy-5-(hydroxymethyl)-2-oxooxolane-3-carboxylic acid

C6H7O7- (191.0191772)


2-carboxy-l-xylonolactone belongs to sugar acids and derivatives class of compounds. Those are compounds containing a saccharide unit which bears a carboxylic acid group. 2-carboxy-l-xylonolactone is soluble (in water) and a moderately acidic compound (based on its pKa). 2-carboxy-l-xylonolactone can be found in a number of food items such as apricot, mentha (mint), allspice, and hedge mustard, which makes 2-carboxy-l-xylonolactone a potential biomarker for the consumption of these food products.

   

2-phospho-D-glycerate

3-hydroxy-2-(phosphonatooxy)propanoate

C3H4O7P (182.9694664)


2-phospho-d-glycerate, also known as 2-phosphonatoglyceric acid(3-), belongs to sugar acids and derivatives class of compounds. Those are compounds containing a saccharide unit which bears a carboxylic acid group. 2-phospho-d-glycerate is soluble (in water) and an extremely strong acidic compound (based on its pKa). 2-phospho-d-glycerate can be found in a number of food items such as wasabi, sea-buckthornberry, black chokeberry, and sweet potato, which makes 2-phospho-d-glycerate a potential biomarker for the consumption of these food products.