Reaction Process: BioCyc:META_PWY-5257

superpathway of pentose and pentitol degradation related metabolites

find 29 related metabolites which is associated with chemical reaction(pathway) superpathway of pentose and pentitol degradation

H2O + L-arabinono-1,4-lactone ⟶ H+ + L-arabinonate

D-Xylitol

(2R,3R,4S)-Pentane-1,2,3,4,5-pentaol

C5H12O5 (152.0685)


Xylitol is a five-carbon sugar alcohol that is obtained through the diet. It is not endogenously produced by humans. Xylitol is used as a diabetic sweetener which is roughly as sweet as sucrose with 33\\\\\\% fewer calories. Xylitol is naturally found in many fruits (strawberries, plums, raspberries) and vegetables (e.g. cauliflower). Because of fruit and vegetable consumption the human body naturally processes 15 grams of xylitol per day. Xylitol can be produced industrially starting from primary matters rich in xylan which is hydrolyzed to obtain xylose. It is extracted from hemicelluloses present in the corn raids, the almond hulls or the barks of birch (or of the by-products of wood: shavings hard, paper pulp). Of all polyols, it is the one that has the sweetest flavor (it borders that of saccharose). It gives a strong refreshing impression, making xylitol an ingredient of choice for the sugarless chewing gum industry. In addition to his use in confectionery, it is used in the pharmaceutical industry for certain mouthwashes and toothpastes and in cosmetics (creams, soaps, etc.). Xylitol is produced starting from xylose, the isomaltose, by enzymatic transposition of the saccharose (sugar). Xylitol is not metabolized by cariogenic (cavity-causing) bacteria and gum chewing stimulates the flow of saliva; as a result, chewing xylitol gum may prevent dental caries. Chewing xylitol gum for 4 to 14 days reduces the amount of dental plaque. The reduction in the amount of plaque following xylitol gum chewing within 2 weeks may be a transient phenomenon. Chewing xylitol gum for 6 months reduced mutans streptococci levels in saliva and plaque in adults (PMID:17426399, 15964535). Studies have also shown xylitol chewing gum can help prevent acute otitis media (ear aches and infections) as the act of chewing and swallowing assists with the disposal of earwax and clearing the middle ear, while the presence of xylitol prevents the growth of bacteria in the eustachian tubes. Xylitol is well established as a life-threatening toxin to dogs. The number of reported cases of xylitol toxicosis in dogs has significantly increased since the first reports in 2002. Dogs that have ingested foods containing xylitol (greater than 100 milligrams of xylitol consumed per kilogram of bodyweight) have presented with low blood sugar (hypoglycemia), which can be life-threatening. Xylitol is found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism. Occurs in a variety of plants, berries and fruits including plums, raspberries, cauliflower and endive; sweetening agent used in sugar free sweets and chewing gum 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 Ribitol is a crystalline pentose alcohol formed by the reduction of ribose. Enhancing the flux of D-glucose to the pentose phosphate pathway in Saccharomyces cerevisiae for the production of D-ribose and ribitol. Ribitol is a crystalline pentose alcohol formed by the reduction of ribose. Enhancing the flux of D-glucose to the pentose phosphate pathway in Saccharomyces cerevisiae for the production of D-ribose and ribitol. Xylitol can be classified as polyols and sugar alcohols. Xylitol can be classified as polyols and sugar alcohols.

   

D-Xylose

(3R,4S,5R)-Tetrahydro-2H-pyran-2,3,4,5-tetrol

C5H10O5 (150.0528)


Xylose or wood sugar is an aldopentose - a monosaccharide containing five carbon atoms and an aldehyde functional group. It has chemical formula C5H10O5 and is 40\\\\% as sweet as sucrose. Xylose is found in the embryos of most edible plants. The polysaccharide xylan, which is closely associated with cellulose, consists practically entirely of d-xylose. Corncobs, cottonseed hulls, pecan shells, and straw contain considerable amounts of this sugar. Xylose is also found in mucopolysaccharides of connective tissue and sometimes in the urine. Xylose is the first sugar added to serine or threonine residues during proteoglycan type O-glycosylation. Therefore xylose is involved in the biosythetic pathways of most anionic polysaccharides such as heparan sulphate and chondroitin sulphate. In medicine, xylose is used to test for malabsorption by administering a xylose solution to the patient after fasting. If xylose is detected in the blood and/or urine within the next few hours, it has been absorbed by the intestines. Xylose is said to be one of eight sugars which are essential for human nutrition, the others being galactose, glucose, mannose, N-acetylglucosamine, N-acetylgalactosamine, fucose, and sialic acid. (Wikipedia). Xylose in the urine is a biomarker for the consumption of apples and other fruits. Xylose is a sugar first isolated from wood, and named for it. Xylose is classified as a monosaccharide of the aldopentose type, which means that it contains five carbon atoms and includes an aldehyde functional group. It is the precursor to hemicellulose, one of the main constituents of biomass. D-Xylopyranose is found in flaxseed. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose. D-(+)-xylose (Xylose) is a natural compound that is catalyzed by xylose isomerase to form xylulose, which is a key step in the anaerobic ethanol fermentation of xylose.

   

D-Arabinono-1,4-lactone

(3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-one

C5H8O5 (148.0372)


D-arabinono-1,4-lactone, also known as D-arabinonic acid, gamma-lactone, is a member of the class of compounds known as pentoses. Pentoses are monosaccharides in which the carbohydrate moiety contains five carbon atoms. D-arabinono-1,4-lactone is soluble (in water) and a very weakly acidic compound (based on its pKa). D-arabinono-1,4-lactone can be found in rice, which makes D-arabinono-1,4-lactone a potential biomarker for the consumption of this food product. D-arabinono-1,4-lactone may be a unique S.cerevisiae (yeast) metabolite.

   

Glycolaldehyde

Monomethylolformaldehyde

C2H4O2 (60.0211)


Glycolaldehyde, also known as hydroxyacetaldehyde or methylol formaldehyde, is a member of the class of compounds known as short-chain aldehydes. Short-chain aldehydes are an aldehyde with a chain length containing between 2 and 5 carbon atoms. Glycolaldehyde is soluble (in water) and a very weakly acidic compound (based on its pKa). Glycolaldehyde can be found in a number of food items such as acorn, elderberry, dandelion, and conch, which makes glycolaldehyde a potential biomarker for the consumption of these food products. Glycolaldehyde can be found primarily in human neuron tissue. Glycolaldehyde exists in all living organisms, ranging from bacteria to humans. In humans, glycolaldehyde is involved in the vitamin B6 metabolism. Glycolaldehyde is also involved in hypophosphatasia, which is a metabolic disorder. Glycolaldehyde is the organic compound with the formula HOCH2-CHO. It is the smallest possible molecule that contains both an aldehyde group and a hydroxyl group. It is a highly reactive molecule that occurs both in the biosphere and in the interstellar medium. It is normally supplied as a white solid. Although it conforms to the general formula for carbohydrates, Cn(H2O)n, it is not generally considered to be a saccharide . Glycolaldehyde (HOCH2-CH=O, IUPAC name 2-hydroxyethanal) is a type of diose (2-carbon monosaccharide). Glycolaldehyde is readily converted to acetyl coenzyme A. It has an aldehyde and a hydroxyl group. However, it is not actually a sugar, because there is only one hydroxyl group. Glycolaldehyde is formed from many sources, including the amino acid glycine and from purone catabolism. It can form by action of ketolase on fructose 1,6-bisphosphate in an alternate glycolysis pathway. This compound is transferred by thiamin pyrophosphate during the pentose phosphate shunt.

   

Water

oxidane

H2O (18.0106)


Water is a chemical substance that is essential to all known forms of life. It appears colorless to the naked eye in small quantities, though it is actually slightly blue in color. It covers 71\\% of Earths surface. Current estimates suggest that there are 1.4 billion cubic kilometers (330 million m3) of it available on Earth, and it exists in many forms. It appears mostly in the oceans (saltwater) and polar ice caps, but it is also present as clouds, rain water, rivers, freshwater aquifers, lakes, and sea ice. Water in these bodies perpetually moves through a cycle of evaporation, precipitation, and runoff to the sea. Clean water is essential to human life. In many parts of the world, it is in short supply. From a biological standpoint, water has many distinct properties that are critical for the proliferation of life that set it apart from other substances. It carries out this role by allowing organic compounds to react in ways that ultimately allow replication. All known forms of life depend on water. Water is vital both as a solvent in which many of the bodys solutes dissolve and as an essential part of many metabolic processes within the body. Metabolism is the sum total of anabolism and catabolism. In anabolism, water is removed from molecules (through energy requiring enzymatic chemical reactions) in order to grow larger molecules (e.g. starches, triglycerides and proteins for storage of fuels and information). In catabolism, water is used to break bonds in order to generate smaller molecules (e.g. glucose, fatty acids and amino acids to be used for fuels for energy use or other purposes). Water is thus essential and central to these metabolic processes. Water is also central to photosynthesis and respiration. Photosynthetic cells use the suns energy to split off waters hydrogen from oxygen. Hydrogen is combined with CO2 (absorbed from air or water) to form glucose and release oxygen. All living cells use such fuels and oxidize the hydrogen and carbon to capture the suns energy and reform water and CO2 in the process (cellular respiration). Water is also central to acid-base neutrality and enzyme function. An acid, a hydrogen ion (H+, that is, a proton) donor, can be neutralized by a base, a proton acceptor such as hydroxide ion (OH-) to form water. Water is considered to be neutral, with a pH (the negative log of the hydrogen ion concentration) of 7. Acids have pH values less than 7 while bases have values greater than 7. Stomach acid (HCl) is useful to digestion. However, its corrosive effect on the esophagus during reflux can temporarily be neutralized by ingestion of a base such as aluminum hydroxide to produce the neutral molecules water and the salt aluminum chloride. Human biochemistry that involves enzymes usually performs optimally around a biologically neutral pH of 7.4. (Wikipedia). Water, also known as purified water or dihydrogen oxide, is a member of the class of compounds known as homogeneous other non-metal compounds. Homogeneous other non-metal compounds are inorganic non-metallic compounds in which the largest atom belongs to the class of other nonmetals. Water can be found in a number of food items such as caraway, oxheart cabbage, alaska wild rhubarb, and japanese walnut, which makes water a potential biomarker for the consumption of these food products. Water can be found primarily in most biofluids, including ascites Fluid, blood, cerebrospinal fluid (CSF), and lymph, as well as throughout all human tissues. Water exists in all living species, ranging from bacteria to humans. In humans, water is involved in several metabolic pathways, some of which include cardiolipin biosynthesis CL(20:4(5Z,8Z,11Z,14Z)/18:0/20:4(5Z,8Z,11Z,14Z)/18:2(9Z,12Z)), cardiolipin biosynthesis cl(i-13:0/i-15:0/i-20:0/i-24:0), cardiolipin biosynthesis CL(18:0/18:0/20:4(5Z,8Z,11Z,14Z)/22:5(7Z,10Z,13Z,16Z,19Z)), and cardiolipin biosynthesis cl(a-13:0/i-18:0/i-13:0/i-19:0). Water is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis tg(i-21:0/i-13:0/21:0), de novo triacylglycerol biosynthesis tg(22:0/20:0/i-20:0), de novo triacylglycerol biosynthesis tg(a-21:0/i-20:0/i-14:0), and de novo triacylglycerol biosynthesis tg(i-21:0/a-17:0/i-12:0). Water is a drug which is used for diluting or dissolving drugs for intravenous, intramuscular or subcutaneous injection, according to instructions of the manufacturer of the drug to be administered [fda label]. Water plays an important role in the world economy. Approximately 70\\% of the freshwater used by humans goes to agriculture. Fishing in salt and fresh water bodies is a major source of food for many parts of the world. Much of long-distance trade of commodities (such as oil and natural gas) and manufactured products is transported by boats through seas, rivers, lakes, and canals. Large quantities of water, ice, and steam are used for cooling and heating, in industry and homes. Water is an excellent solvent for a wide variety of chemical substances; as such it is widely used in industrial processes, and in cooking and washing. Water is also central to many sports and other forms of entertainment, such as swimming, pleasure boating, boat racing, surfing, sport fishing, and diving .

   

D-Xylono-1,5-lactone

(3R,4S,5R)-3,4,5-trihydroxyoxan-2-one

C5H8O5 (148.0372)


D-xylonolactone is a lactone derivative of xylonic acid. It is an intermediate in the pentose and glucuronate interconversion pathway and can be formed from either D-xylonic acid or D-xylose. D-xylose is a simple 5 carbon sugar that is found in a variety of edible plants. It is also frequently used in intestinal absorption tests to help diagnose problems that prevent the small intestine from absorbing nutrients in food. Xylose is also the first saccharide added to the serine or threonine in the proteoglycan type O-glycosylation and so it is the first saccharide in biosynthetic pathways of most anionic polysaccharides such as heparan sulfate and chondroitin sulfate. D-xylose is normally easily absorbed by the intestines where it can be converted to D-xylonolactone by intestinal D-xylose 1-dehydrogenase (EC 1.1.1.175). [HMDB] D-xylonolactone is a lactone derivative of xylonic acid. It is an intermediate in the pentose and glucuronate interconversion pathway and can be formed from either D-xylonic acid or D-xylose. D-xylose is a simple 5 carbon sugar that is found in a variety of edible plants. It is also frequently used in intestinal absorption tests to help diagnose problems that prevent the small intestine from absorbing nutrients in food. Xylose is also the first saccharide added to the serine or threonine in the proteoglycan type O-glycosylation and so it is the first saccharide in biosynthetic pathways of most anionic polysaccharides such as heparan sulfate and chondroitin sulfate. D-xylose is normally easily absorbed by the intestines where it can be converted to D-xylonolactone by intestinal D-xylose 1-dehydrogenase (EC 1.1.1.175).

   

D-Arabitol

D-Arabinitol - L-arabinitol (1:1)

C5H12O5 (152.0685)


D-Arabitol is a polyol. Polyols are sugar alcohols linked to the pentose phosphate pathway (PPP). They are classified on the basis of the number of carbon atoms. Polyols occur in body fluids. A patient with leukoencephalopathy and peripheral neuropathy has been identified as suffering from ribose-5-phosphate isomerase (RPI) deficiency, a defect in the PPP. In this disorder, highly elevated concentrations of the C5 polyols such as D-arabitol are found in body fluids. In addition, transaldolase deficiency, another defect in the PPP, has been diagnosed in a patient with mainly liver problems among others. This patient had increased concentrations of polyols, mainly D-arabitol. So far, the pathophysiological role of polyols is relatively unknown. It is thought that D-arabitol is a metabolic end-product in humans. The strong brain-CSF-plasma gradient of polyols in the patient with RPI deficiency suggested a primary metabolic disorder. The mechanisms of brain and neuronal damage in RPI deficiency remain to be elucidated. A neurotoxic effect due to the accumulation of the polyols may play a role. D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the pentose and glucuronate interconversion pathway (PMID: 16435225, J Inherit Metab Dis. 2005;28(6):1181-3). D-Arabitol has also been found to be a fungal metabolite, urinary D-Arabinitol is a marker for invasive candidiasis or infection by Candida fungal species (PMID: 15183861; PMID: 10647119). It can also a metabolite in Debaryomyces, Pichia and Zygosaccharomyces (PMID: 25809659). D-Arabitol is a polyol. Polyols are sugar alcohols linked to the pentose phosphate pathway (PPP). They are classified on the basis of the number of carbon atoms. Polyols occur in body fluids. A patient with leukoencephalopathy and peripheral neuropathy has been identified as suffering from ribose-5-phosphate isomerase (RPI) deficiency, a defect in the PPP. In this disorder, highly elevated concentrations of the C5 polyols such as D-arabitol are found in body fluids. In addition, transaldolase deficiency, another defect in the PPP, has been diagnosed in a patient with mainly liver problems among others had increased concentrations of polyols, mainly D-arabitol. So far, the pathophysiological role of polyols is relatively unknown. It is thought that D-arabitol is a metabolic end-product in humans. The strong brain-CSF-plasma gradient of polyols in the patient with RPI deficiency suggested a primary metabolic disorder. The mechanisms of brain and neuronal damage in RPI deficiency remain to be elucidated. A neurotoxic effect due to accumulation of the polyols may play a role. D-Arabitol is a product of the enzyme D-arabinitol 4-dehydrogenase (EC 1.1.1.11) in the Pentose and glucuronate interconversion pathway. (PMID: 16435225, J Inherit Metab Dis. 2005;28(6):1181-3). D-Arabitol is a polyol and its accumulation may cause a neurotoxic effect in human. D-Arabitol is a polyol and its accumulation may cause a neurotoxic effect in human.

   

L-Arabitol

(2S,4S)-pentane-1,2,3,4,5-pentol

C5H12O5 (152.0685)


L-Arabitol, also known as L-arabinitol or L-lyxitol, is a member of the class of compounds known as sugar alcohols. Sugar alcohols are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone reducing sugar) has been reduced to a primary or secondary hydroxyl group. L-Arabitol is soluble in water. L-Arabitol can be found in a number of food items such as sweet potato, deerberry, moth bean, and European chestnut, which makes L-arabitol a potential biomarker for the consumption of these food products. L-Arabitol can be found in most biofluids, including urine, cerebrospinal fluid (CSF), saliva, and blood. L-Arabitol exists in all living species, ranging from bacteria to humans. Moreover, L-arabitol is found to be associated with Alzheimers disease and ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism. L-Arabitol can be formed by the reduction of either arabinose or lyxose. L-Arabitol has been reported in pentosuric acidemia (PMID:13525419). L-Arabinosinuia has been described in a patient, presented at the age of 16 months with delayed motor development and facial dysmorphism (PMID:12359133) Congenital liver cirrhosis has been recently described in a patient with highly elevated plasma and urine levels of arabitol due to transaldolase deficiency (Inherit Metab Dis 23(Suppl. 1):172, 2000). L-Arabitol has been reported in pentosuric acidemia (PMID 13525419). L-Arabinosinuia has been described in a patient, presented at the age of 16 months with delayed motor development and facial dysmorphism. (PMID 12359133) Congenital liver cirrhosis has been recently described in a patient with highly elevated plasma and urine levels of arabitol due to transaldolase deficiency. (Inherit Metab Dis 23(Suppl. 1):172, 2000.) [HMDB]. L-Arabitol is found in many foods, some of which are red raspberry, sweet orange, dandelion, and hyssop. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS L-Arabinitol is a potential biomarker for the comsuption of the food products such as sweet potato, deerberry, moth bean, and is also associated with Alzheimer's disease and ribose-5-phosphate isomerase deficiency.

   

Hydrogen Ion

Hydrogen cation

H+ (1.0078)


Hydrogen ion, also known as proton or h+, is a member of the class of compounds known as other non-metal hydrides. Other non-metal hydrides are inorganic compounds in which the heaviest atom bonded to a hydrogen atom is belongs to the class of other non-metals. Hydrogen ion can be found in a number of food items such as lowbush blueberry, groundcherry, parsley, and tarragon, which makes hydrogen ion a potential biomarker for the consumption of these food products. Hydrogen ion exists in all living organisms, ranging from bacteria to humans. In humans, hydrogen ion is involved in several metabolic pathways, some of which include cardiolipin biosynthesis cl(i-13:0/a-25:0/a-21:0/i-15:0), cardiolipin biosynthesis cl(a-13:0/a-17:0/i-13:0/a-25:0), cardiolipin biosynthesis cl(i-12:0/i-13:0/a-17:0/a-15:0), and cardiolipin biosynthesis CL(16:1(9Z)/22:5(4Z,7Z,10Z,13Z,16Z)/18:1(11Z)/22:5(7Z,10Z,13Z,16Z,19Z)). Hydrogen ion is also involved in several metabolic disorders, some of which include de novo triacylglycerol biosynthesis TG(20:3(8Z,11Z,14Z)/22:6(4Z,7Z,10Z,13Z,16Z,19Z)/22:5(7Z,10Z,13Z,16Z,19Z)), de novo triacylglycerol biosynthesis TG(18:2(9Z,12Z)/20:0/20:4(5Z,8Z,11Z,14Z)), de novo triacylglycerol biosynthesis TG(18:4(6Z,9Z,12Z,15Z)/18:3(9Z,12Z,15Z)/18:4(6Z,9Z,12Z,15Z)), and de novo triacylglycerol biosynthesis TG(24:0/20:5(5Z,8Z,11Z,14Z,17Z)/24:0). A hydrogen ion is created when a hydrogen atom loses or gains an electron. A positively charged hydrogen ion (or proton) can readily combine with other particles and therefore is only seen isolated when it is in a gaseous state or a nearly particle-free space. Due to its extremely high charge density of approximately 2×1010 times that of a sodium ion, the bare hydrogen ion cannot exist freely in solution as it readily hydrates, i.e., bonds quickly. The hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions . Hydrogen ion is recommended by IUPAC as a general term for all ions of hydrogen and its isotopes. Depending on the charge of the ion, two different classes can be distinguished: positively charged ions and negatively charged ions. Under aqueous conditions found in biochemistry, hydrogen ions exist as the hydrated form hydronium, H3O+, but these are often still referred to as hydrogen ions or even protons by biochemists. [Wikipedia])

   

L-Arabonolactone

L-Arabinono-1,4-lactone

C5H8O5 (148.0372)


   

D-Xylonate

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

C5H9O6- (165.0399)


   

D-Ribulose

erythro-2-Pentulose (9CI)

C5H10O5 (150.0528)


The D-stereoisomer of ribulose.

   

D-Xylulose

D-Xylulose

C5H10O5 (150.0528)


The D-enantiomer of xylulose.

   

Nicotinamide adenine dinucleotide

Nicotinamide adenine dinucleotide

C21H26N7O14P2- (662.1013)


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Coenzyme II

Coenzyme II

C21H25N7O17P3-3 (740.052)


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Pyruvate

Pyruvate

C3H3O3- (87.0082)


A 2-oxo monocarboxylic acid anion that is the conjugate base of pyruvic acid, arising from deprotonation of the carboxy group.

   

Glycolate

Glycolate

C2H3O3- (75.0082)


A hydroxy monocarboxylic acid anion that is acetate where the methyl group has been hydroxylated. D003879 - Dermatologic Agents > D007641 - Keratolytic Agents

   

L-Ribulose

D-(−)-Ribulose

C5H10O5 (150.0528)


   
   

Glycerone phosphate(2-)

Glycerone phosphate(2-)

C3H5O6P-2 (167.9824)


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beta-NADH

beta-NADH

C21H27N7O14P2-2 (663.1091)


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L-Xylulose

L-(+)-Ribulose

C5H10O5 (150.0528)


   

D-Arabinonate

D-Arabinonate

C5H9O6- (165.0399)


   

Xylulose 5-phosphate

Xylulose 5-phosphate

C5H9O8P-2 (228.0035)


   

L-Arabinonate

L-Arabinonate

C5H9O6- (165.0399)


   

2-Dehydro-3-deoxy-L-arabinonate

2-Dehydro-3-deoxy-L-arabinonate

C5H7O5- (147.0293)


   

D-ribulose 1-phosphate(2-)

D-ribulose 1-phosphate(2-)

C5H9O8P-2 (228.0035)


   

2-Dehydro-3-deoxy-D-arabinonate

2-Dehydro-3-deoxy-D-arabinonate

C5H7O5- (147.0293)


   

5-O-phosphonato-L-ribulose

5-O-phosphonato-L-ribulose

C5H9O8P-2 (228.0035)