Classification Term: 2836

Pyrimidine nucleotide sugars (ontology term: CHEMONTID:0001296)

Pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group." []

found 30 associated metabolites at sub_class metabolite taxonomy ontology rank level.

Ancestor: Pyrimidine nucleotides

Child Taxonomies: There is no child term of current ontology term.

Deoxythymidine diphosphate-L-rhamnose

[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl]methyl (2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl dihydrogen diphosphate (non-preferred name)

C16H26N2O15P2 (548.0808)


Deoxythymidine diphosphate-L-rhamnose (dTDP-L-rhamnose) is the precursor of L-rhamnose, a saccharide required for the virulence of some pathogenic bacteria. In gram-negative bacteria such as Salmonella enterica, Vibrio cholerae, or Escherichia coli 075:K5, L-rhamnose is an important residue in the O-antigen of lipopolysaccharides, which are essential for resistance to serum killing and colonization. In gram-positive bacteria such as streptococci, the capsule is a recognized virulence factor. For example, L-rhamnose is known to be present in the capsule of Streptococcus suis, a causative agent of meningitis in humans. In Streptococcus mutans, L-rhamnose containing polysaccharides have been implicated in tooth surface colonization and adherence to kidney, muscle, and heart tissues. In mycobacteria, L-rhamnose is fundamental to the structural integrity of the cell wall since it connects the inner peptidoglycan layer to the arabinogalactan polysaccharides. dTDP-L-rhamnose is synthesized from glucose-1-phosphate and deoxythymidine triphosphate (dTTP) via a pathway involving four distinct enzymes. Whereas common sugars such as glucose, fructose, and mannose are all D-configured, bacteria commonly utilize the L-configured carbohydrates in pharmacologically active compounds and their cell-wall structures. The bacterial cell wall is unique to bacteria; neither the cell wall nor the enzymes and chemical intermediates in its formation have analogues in humans. The enzymes involved in dTDP-L-rhamnose synthesis are potential targets for the design of new therapeutic agents (PMID: 10802738, 12773151). 2-deoxy-thymidine-beta-l-rhamnose, also known as dtdp-6-deoxy-L-mannose or thymidine diphosphate-L-rhamnose, is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. 2-deoxy-thymidine-beta-l-rhamnose is soluble (in water) and a moderately acidic compound (based on its pKa). 2-deoxy-thymidine-beta-l-rhamnose can be found in a number of food items such as black salsify, dill, roman camomile, and tea leaf willow, which makes 2-deoxy-thymidine-beta-l-rhamnose a potential biomarker for the consumption of these food products. DTDP-beta-L-rhamnose is the beta-anomer of dTDP-L-rhamnose. It has a role as an Escherichia coli metabolite. It is functionally related to a dTDP-L-mannose. It is a conjugate acid of a dTDP-6-deoxy-beta-L-mannose(2-). Deoxythymidine diphosphate-L-rhamnose is a metabolite found in or produced by Escherichia coli (strain K12, MG1655). The beta-anomer of dTDP-L-rhamnose.

   

Uridine diphosphate glucose

[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

C15H24N2O17P2 (566.055)


Uridine diphosphate glucose, also known as UDP-glucose or UDP-alpha-D-glucose, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Uridine diphosphate glucose exists in all living species, ranging from bacteria to plants to humans. Uridine diphosphate glucose is a key intermediate in carbohydrate metabolism. For instance, UDP-glucose is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid. UDP-glucose can also be used as a precursor for the biosynthesis of sucrose, lipopolysaccharides and glycosphingolipids. Within humans, uridine diphosphate glucose participates in a number of enzymatic reactions. In particular, ceramide (D18:1/18:0) and uridine diphosphate glucose can be converted into glucosylceramide (D18:1/18:0) and uridine 5-diphosphate through the action of the enzyme ceramide glucosyltransferase. In addition, glucosylceramide (D18:1/18:0) and uridine diphosphate glucose can be biosynthesized from lactosylceramide (D18:1/18:0) and uridine 5-diphosphate through its interaction with the enzyme Beta-1,4-galactosyltransferase 6. A key intermediate in carbohydrate metabolism. Serves as a precursor of glycogen, can be metabolized into UDPgalactose and UDPglucuronic acid which can then be incorporated into polysaccharides as galactose and glucuronic acidand is also serves as a precursor of sucrose lipopolysaccharides, and glycosphingolipids.; It is a precursor of glycogen and can be converted into UDP-galactose and UDP-glucuronic acid, which can then be used as substrates by the enzymes that make polysaccharides containing galactose and glucuronic acid.; Uridine diphosphate glucose (uracil-diphosphate glucose, UDP-glucose) is a nucleotide sugar. It is involved in glycosyltransferase reactions in metabolism. Udp-glucose is found in many foods, some of which are skunk currant, black salsify, winter squash, and red algae. Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

Uridine diphosphate-N-acetylglucosamine

(2R,3R,4R,5S,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphoric acid (non-preferred name)

C17H27N3O17P2 (607.0816)


Uridine diphosphate-N-acetylglucosamine (uridine 5-diphosphate-GlcNAc, or UDP-Glc-NAc) is an acetylated aminosugar nucleotide. UDP-GlcNAc is the donor substrate for modification of nucleocytoplasmic proteins at serine and threonine residues with N-acetylglucosamine (O-GlcNAc). Nutrient sensing in mammals is done through the hexosamine biosynthetic pathway (HSP), which produces uridine 5-diphospho-N-acetylglucosamine (UDP-Glc-NAc) as its end product. Mammals respond to nutrient excess by activating O-GlcNAcylation (addition of O-linked N-acetylglucosamine). O-GlcNAc addition (and removal) is key to histone remodeling, transcription, proliferation, apoptosis, and proteasomal degradation. This nutrient-responsive signaling pathway also modulates important cellular pathways, including the insulin signaling cascade in. Alterations in O-GlcNAc metabolism are associated with various human diseases including diabetes mellitus and neurodegeneration. (PMID: 16317114) Due to the chemical makeup of UDP-GlcNAc, it is well positioned to serve as a glucose sensor in that it is a high-energy compound that requires and/or responds to glucose, amino acid, fatty acid and nucleotide metabolism for synthesis. Elevated levels of O-GlcNAc have an effect on insulin-stimulated glucose uptake. (PMID: 12678487). Uridine 5-diphosphate-GlcNAc (UDP-Glc-NAc )respond to nutrient excess to activate O-GlcNAcylation (addition of O-linked N-acetylglucosamine) in the hexosamine signaling pathway (HSP). O-GlcNAc addition (and removal) is key to histone remodeling, transcription, proliferation, apoptosis, and proteasomal degradation. This nutrient-responsive signaling pathway also modulates important cellular pathways, including the insulin signaling cascade in. Alterations in O-GlcNAc metabolism are associated with various human diseases including diabetes mellitus and neurodegeneration. (PMID: 16317114) Acquisition and generation of the data is financially supported in part by CREST/JST.

   

UDP-L-rhamnose

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}({[hydroxy({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid

C15H24N2O16P2 (550.0601)


UDP-L-rhamnose is synthesized from UDP-D-glucose. [HMDB]. UDP-L-rhamnose is found in many foods, some of which are maitake, orange bell pepper, common mushroom, and horseradish tree. Acquisition and generation of the data is financially supported in part by CREST/JST. UDP-L-rhamnose is synthesized from UDP-D-glucose.

   

Cytidine 5'-monophosphate-N-acetylneuraminic acid

(2R,4S,5R,6R)-2-[({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-acetamido-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid

C20H31N4O16P (614.1473)


Cytidine 5-monophosphate-N-acetylneuraminic acid (CMP-Neu5Ac), also known as CMP-N-acetyl-β-neuraminic acid, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. CMP-Neu5Ac is an extremely weak basic (essentially neutral) compound (based on its pKa). CMP-Neu5Ac donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein. A nucleoside monophosphate sugar which donates N-acetylneuraminic acid to the terminal sugar of a ganglioside or glycoprotein. [HMDB] COVID info from WikiPathways Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

CDP-glucose

{[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}({[hydroxy({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl]oxy})phosphinic acid

C15H25N3O16P2 (565.071)


CDP-glucose is a substrate for Uridine diphosphate glucose pyrophosphatase. [HMDB] CDP-glucose is a substrate for Uridine diphosphate glucose pyrophosphatase.

   

dTDP-D-glucose

{[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

C16H26N2O16P2 (564.0758)


Deoxythymidine diphosphate-glucose is an intermediate in the nucleotide sugar metabolism pathway (KEGG). It is a substrate for the enzyme dTDP-D-glucose 4,6-dehydratase which catalyzes the reaction: dTDP-glucose = dTDP-4-dehydro-6-deoxy-D-glucose + H2O. Deoxythymidine diphosphate-glucose is an intermediate in the Nucleotide sugars metabolism pathway (KEGG) [HMDB]

   

UDP-N-acetylmuraminate

(2r)-2-{[(2r,3r,4r,5s,6r)-3-(Acetylamino)-2-{[(S)-{[(R)-{[(2r,3s,4r,5r)-5-(2,4-Dioxo-3,4-Dihydropyrimidin-1(2h)-Yl)-3,4-Dihydroxytetrahydrofuran-2-Yl]methoxy}(Hydroxy)phosphoryl]oxy}(Hydroxy)phosphoryl]oxy}-5-Hydroxy-6-(Hydroxymethyl)tetrahydro-2h-Pyran-4-Yl]oxy}propanoic Acid

C20H31N3O19P2 (679.1027)


UDP-N-acetylmuraminate is a nucleoside diphosphate sugar which is formed from UDP-N-acetylglucosamine and phosphoenolpyruvate. It serves as the building block upon which peptidoglycan is formed. UDP-N-acetylmuraminate, also known as UDP-MurNAc, is a key molecule in the biosynthesis of bacterial cell walls. It is a nucleotide sugar, which means it consists of a nucleotide (uridine diphosphate, UDP) linked to a sugar molecule (N-acetylmuramic acid, MurNAc). This compound plays a critical role in the formation of peptidoglycan, the essential structural component of the bacterial cell wall. Here are some key points about UDP-N-acetylmuraminate: Biosynthesis: UDP-MurNAc is synthesized from UDP-N-acetylglucosamine (UDP-GlcNAc) through a series of enzymatic reactions. The addition of a lactyl group to UDP-GlcNAc forms UDP-MurNAc. Peptidoglycan Precursor: It serves as a precursor for the synthesis of peptidoglycan, which is a polymer made up of alternating units of N-acetylglucosamine (GlcNAc) and N-acetylmuramic acid (MurNAc). The peptide chains attached to MurNAc units cross-link to provide structural strength to the cell wall. Enzymatic Processing: UDP-MurNAc is further processed by enzymes such as Mur synthases, which add amino acids to form the pentapeptide chain attached to the MurNAc residue. This pentapeptide is crucial for the cross-linking of peptidoglycan layers. Target for Antibiotics: Since peptidoglycan synthesis is unique to bacteria, enzymes involved in the biosynthesis and processing of UDP-MurNAc are targets for antibiotics. Inhibiting these enzymes can prevent proper cell wall formation, leading to bacterial cell death. Importance in Bacterial Growth: The availability of UDP-MurNAc is essential for bacterial growth and cell division, as it is a direct precursor to the building blocks of the cell wall. Research and Applications: Understanding the biosynthesis and function of UDP-MurNAc is important for developing new antibiotics, as well as for basic research in bacterial cell biology. UDP-N-acetylmuraminate is a vital molecule in the construction of the bacterial cell wall, and its biosynthesis and function are of significant interest in both basic research and the development of antibacterial therapies. A nucleoside diphosphate sugar which is formed from UDP-N-acetylglucosamine and phosphoenolpyruvate. It serves as the building block upon which peptidoglycan is formed [HMDB]

   

UDP-4-dehydro-6-deoxy-D-glucose

{[(2R,3S,4R,5R)-3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}[({[(2R,3R,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}(hydroxy)phosphoryl)oxy]phosphinic acid

C15H22N2O16P2 (548.0445)


UDP-4-dehydro-6-deoxy-D-glucose, also known as UDP-4-keto-6-deoxy-D-glucose, belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. UDP-4-dehydro-6-deoxy-D-glucose is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, UDP-4-dehydro-6-deoxy-D-glucose has been detected, but not quantified in, several different foods, such as Oregon yampahs, oriental wheat, Chinese mustards, blackcurrants, and pomegranates. This could make UDP-4-dehydro-6-deoxy-D-glucose a potential biomarker for the consumption of these foods. UDP-4-dehydro-6-deoxy-D-glucose is synthesized from UDP-glucose via the enzyme UDP-glucose 4,6-dehydratase. UDP-4-dehydro-6-deoxy-D-glucose is synthesized from UDP-glucose through the enzyme UDP-glucose 4,6-dehydratase. [HMDB]. UDP-4-dehydro-6-deoxy-D-glucose is found in many foods, some of which are alaska wild rhubarb, soy bean, ginkgo nuts, and common beet.

   

dTDP-4-acetamido-4,6-dideoxy-D-galactose

{[(3R,4S,6R)-5-acetamido-3,4-dihydroxy-6-methyloxan-2-yl]oxy}({[hydroxy({[3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid

C18H29N3O15P2 (589.1074)


dTDP-4-acetamido-4,6-dideoxy-D-galactose reacts with undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate to produce undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate and dTDP. The reaction is catalyzed by certain members of the fucosyltransferase family of enzymes. [HMDB] dTDP-4-acetamido-4,6-dideoxy-D-galactose reacts with undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate to produce undecaprenyl N-acetyl-glucosaminyl-N-acetyl-mannosaminuronate-4-acetamido-4,6-dideoxy-D-galactose pyrophosphate and dTDP. The reaction is catalyzed by certain members of the fucosyltransferase family of enzymes.

   

Uridine diphosphategalactose

[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

C15H24N2O17P2 (566.055)


Uridine diphosphategalactose (UDPgal) is a nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. UDPgal is a pivotal compound in the metabolism of galactose. UDPgal is a product of the galactose-l-phosphate uridyl transferase (EC 2.7.7.10) reaction but may also be made from Glucose-l-P, involving uridine diphosphate galactose-4-epimerase (EC 5.1.3.2). UDPgal is the necessary galactosyl donor of galactose in the metabolism to incorporate it into complex oligosaccharides, glycoproteins and glycolipids (galactosides). Defective galactosylation of complex glycoconjugates exists in tissues from galactosemic patients. There is a tendency for galactosemic red cell UDPgal to be in the low normal range with a high uridine diphosphate glucose to UDP-gal ratio. This may reflect an inability of red cell UDPgal-4-epimerase to maintain a normal ratio and consequently higher levels of UDPgal. In the more complex white blood cells and cultured fibroblasts, the UDPgal content and the uridine diphosphate glucose to UDPgal ratio of galactosemics are normal. Therefore, defective galactosylation observed in galactosemic fibroblasts must result from a defect in the transfer of galactose from UDPgal to these moieties. (PMID: 2122114, 7671968) [HMDB] Uridine diphosphategalactose (UDPgal) is a nucleoside diphosphate sugar which can be epimerized into UDPglucose for entry into the mainstream of carbohydrate metabolism. UDPgal is a pivotal compound in the metabolism of galactose. UDPgal is a product of the galactose-l-phosphate uridyl transferase (EC 2.7.7.10) reaction but may also be made from Glucose-l-P, involving uridine diphosphate galactose-4-epimerase (EC 5.1.3.2). UDPgal is the necessary galactosyl donor of galactose in the metabolism to incorporate it into complex oligosaccharides, glycoproteins and glycolipids (galactosides). Defective galactosylation of complex glycoconjugates exists in tissues from galactosemic patients. There is a tendency for galactosemic red cell UDPgal to be in the low normal range with a high uridine diphosphate glucose to UDP-gal ratio. This may reflect an inability of red cell UDPgal-4-epimerase to maintain a normal ratio and consequently higher levels of UDPgal. In the more complex white blood cells and cultured fibroblasts, the UDPgal content and the uridine diphosphate glucose to UDPgal ratio of galactosemics are normal. Therefore, defective galactosylation observed in galactosemic fibroblasts must result from a defect in the transfer of galactose from UDPgal to these moieties. (PMID: 2122114, 7671968). Acquisition and generation of the data is financially supported in part by CREST/JST. COVID info from COVID-19 Disease Map Corona-virus Coronavirus SARS-CoV-2 COVID-19 SARS-CoV COVID19 SARS2 SARS

   

dTDP-4-oxo-6-deoxy-D-glucose

{[(2R,3R,4R,6R)-3,4-dihydroxy-6-methyl-5-oxooxan-2-yl]oxy}({[hydroxy({[(2R,3S,5R)-3-hydroxy-5-(5-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy})phosphinic acid

C16H24N2O15P2 (546.0652)


dTDP-4-oxo-6-deoxy-D-glucose belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Outside of the human body, dTDP-4-oxo-6-deoxy-D-glucose has been detected, but not quantified in, several different foods, such as common thymes, kumquats, cascade huckleberries, red huckleberries, and lotus. This could make dTDP-4-oxo-6-deoxy-D-glucose a potential biomarker for the consumption of these foods. dTDP-4-oxo-6-deoxy-D-glucose is a product of the enzyme TDP-glucose 4,6-dehydratase (EC 4.2.1.46) in the nucleotide sugars metabolism pathway. 4,6-Dideoxy-4-oxo-dTDP-D-glucose is a product of the enzyme TDP-glucose 4,6-dehydratase [EC:4.2.1.46] in the Nucleotide sugars metabolism (KEGG) [HMDB]

   

UDP-D-galacturonic acid

(2S,3R,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

C15H22N2O18P2 (580.0343)


UDP-D-galacturonic acid (UDP-GalA), belongs to the class of organic compounds known as pyrimidine nucleotide sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. UDP-D-galacturonic acid is known to be formed by the 4-epimerization of UDP-D-glucuronic acid. UDP-D-galacturonic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, UDP-D-galacturonic acid has been detected, but not quantified in, several different foods, such as peaches, apples, Cucurbita (gourd), agaves, and oats. This could make UDP-D-galacturonic acid a potential biomarker for the consumption of these foods. UDP-D-galacturonate, the activated form of this sugar, is known to be formed by the 4-epimerization of UDP-D-glucuronate. [HMDB]. UDP-D-galacturonate is found in many foods, some of which are japanese persimmon, borage, chives, and caraway.

   

UDP-L-iduronate

(2R,3S,4S,5R,6R)-6-({[({[(2R,3S,4R,5R)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

C15H22N2O18P2 (580.0343)


UDP-L-iduronate is converted from UDP-n-glucuronic acid. n-Iduronic and n-glucuronic acid have been identified as the hexuronic acid components of dermatan sulfate. UDP-Dglucose is the metabolic precursor of both uranic acids . Conversion of UDP-u-glucose to UDP-n-glucuronic acid and the subsequent C-5 inversion of UDP-n-glucuronic acid to UDP-Liduronic acid is catalyzed by extracts of mammalian tissues. However, UDP-n-iduronic acid has never been isolated and its role in the polymerization of L-iduronic acid-containing polymers has remained hypothetical. [HMDB] UDP-L-iduronate is converted from UDP-n-glucuronic acid. n-Iduronic and n-glucuronic acid have been identified as the hexuronic acid components of dermatan sulfate. UDP-Dglucose is the metabolic precursor of both uranic acids. Conversion of UDP-u-glucose to UDP-n-glucuronic acid and the subsequent C-5 inversion of UDP-n-glucuronic acid to UDP-Liduronic acid is catalyzed by extracts of mammalian tissues. However, UDP-n-iduronic acid has never been isolated and its role in the polymerization of L-iduronic acid-containing polymers has remained hypothetical.

   

UDP-N-acetyl-D-mannosamine

[({[(2S,3R,4S,5S)-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[(3R,4S,5R,6S)-3-acetamido-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

C17H27N3O17P2 (607.0816)


UDP-N-acetyl-D-mannosamine is involved in teichoic acid (poly-glycerol) biosynthesis pathway and enterobacterial common antigen biosynthesis pathway. It serves as both enzymatic reactants and products in those two pathways. In teichoic acid (poly-glycerol) biosynthesis pathway, UDP-N-acetyl-mannosamine is synthesized from UDP-N-acetyl-glocasamine by UDP-N-acetylglucosamine 2-epimerase, encoded by the mnaA gene. UDP-N-acetyl-D-mannosamine is involved in teichoic acid (poly-glycerol) biosynthesis pathway and enterobacterial common antigen biosynthesis pathway. It serves as both enzymatic reactants and products in those two pathways.

   

CMP-N-glycoloyl-beta-neuraminate(2-)

2-[({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-5-[(1,2-dihydroxyethylidene)amino]-4-hydroxy-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

C20H31N4O17P (630.1422)


CMP-N-glycoloyl-beta-neuraminate(2-) is also known as CMP-N-Glycoloyl-beta-neuraminic acid. CMP-N-glycoloyl-beta-neuraminate(2-) is considered to be soluble (in water) and acidic

   

Uridine diphosphate-N-acetylgalactosamine

N-[2-({[({[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanimidate

C17H27N3O17P2 (607.0816)


Uridine diphosphate-N-acetylgalactosamine (UDP-GalNAc) is a sugar donor metabolite, transferring N-acetylgalactosamine (GalNAc, an O-glycan) from UDP-GalNAc to serine and threonine residues, forming an alpha-anomeric linkage in a reaction catalyzed by enzymes known as UDP-N-acetylgalactosamine: polypeptide N-acetylgalactosaminyltransferases. The addition of GalNAc to serine or threonine represents the first committed step in mucin biosynthesis. O-Glycans impart unique structural features to mucin glycoproteins and numerous membrane receptors, and resistance to thermal change and proteolytic attack in a number of diverse proteins. O-Linked carbohydrate side chains function as ligands for receptors, lymphocyte and leukocyte homing, and as signals for protein sorting (PMID: 12634319). Animal studies suggest that overactivity of the hexosamine pathway, resulting in increased UDP-hexosamines (i.e. UDP-GalNAc) is an important mechanism by which hyperglycemia causes insulin resistance. However, to date, human studies concerning the role of the hexosamine pathway in hyperglycemia-induced insulin resistance are scarce and restricted to measurements of glutamine fructose-6-phosphate amidotransferase (GFAT) enzyme activity. Both positive and negative correlations between GFAT activity in human muscle tissue from patients with type 2 DM and glucose disposal rate have been reported (PMID: 12414889). Uridine diphosphate-N-acetylgalactosamine (UDP-GalNAc) is a sugar donor metabolite, transferring N-acetylgalactosamine (GalNAc, an O-glycan) from UDP-GalNAc to serine and threonine residues, forming an alpha anomeric linkage in a reaction catalyzed by enzymes known as UDP-N-acetylgalactosamine: polypeptide N-acetylgalactosaminyltransferases; addition of GalNAc to serine or threonine represents the first committed step in mucin biosynthesis. O-glycans impart unique structural features to mucin glycoproteins and numerous membrane receptors, and resistance to thermal change and proteolytic attack in a number of diverse proteins. O-linked carbohydrate side chains function as ligands for receptors; lymphocyte and leukocyte homing and as signals for protein sorting. (PMID: 12634319)

   

UDP-N-acetyl-alpha-D-galactosamine

(2R,3R,4R,5R,6R)-3-(Acetylamino)-4,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl [(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen diphosphoric acid (non-preferred name)

C17H27N3O17P2 (607.0816)


This compound belongs to the family of Pyrimidine Nucleotide Sugars. These are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group.

   

DTDP-alpha-D-glucose(2-)

{[hydroxy({[3-hydroxy-5-(4-hydroxy-5-methyl-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy})phosphoryl]oxy}({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

C16H26N2O16P2 (564.0758)


DTDP-alpha-D-glucose(2-) is also known as dTDP-a-D-Glucose or dTDP-Glucose dianion. DTDP-alpha-D-glucose(2-) is considered to be soluble (in water) and acidic. DTDP-alpha-D-glucose(2-) can be found throughout numerous foods such as Common walnuts, Sacred lotus, Ryes, and Tea. DTDP-alpha-D-glucose(2-) may be a unique E.coli metabolite

   

Cmp-nana

2-[({[3,4-dihydroxy-5-(2-hydroxy-4-imino-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-4-hydroxy-5-[(1-hydroxyethylidene)amino]-6-(1,2,3-trihydroxypropyl)oxane-2-carboxylic acid

C20H31N4O16P (614.1473)


   

Glucose-uridine-C1,5'-diphosphate

[({[3,4-dihydroxy-5-(4-hydroxy-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]({[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphinic acid

C15H24N2O17P2 (566.055)


   

(2R,3R,4R,5S,6R)-6-[[[(2S,3R,4R,5R)-5-(2,4-Dioxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid

6-({[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-3,4,5-trihydroxyoxane-2-carboxylic acid

C15H22N2O18P2 (580.0343)


   

CMP-3-deoxy-D-manno-octulosonate

2-[({[3,4-dihydroxy-5-(4-imino-2-oxido-1,4-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy]-6-(1,2-dihydroxyethyl)-4,5-dihydroxyoxane-2-carboxylic acid

C17H24N3O15P (541.0945)


Cmp-3-deoxy-d-manno-octulosonate is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Cmp-3-deoxy-d-manno-octulosonate is soluble (in water) and a moderately acidic compound (based on its pKa). Cmp-3-deoxy-d-manno-octulosonate can be found in a number of food items such as brassicas, oregon yampah, cloud ear fungus, and shea tree, which makes cmp-3-deoxy-d-manno-octulosonate a potential biomarker for the consumption of these food products.

   

dTDP-alpha-D-glucose

1-[(2R,4S,5R)-4-hydroxy-5-({[hydroxy({[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy})phosphoryl phosphonato]oxy}methyl)oxolan-2-yl]-5-methyl-2-oxo-1,2-dihydropyrimidin-4-olate

C16H24N2O16P2 (562.0601)


Tdp-glucose, also known as dtdp-glucose dianion or dtdp-A-D-glucose, is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Tdp-glucose is soluble (in water) and a moderately acidic compound (based on its pKa). Tdp-glucose can be found in a number of food items such as bog bilberry, red rice, grass pea, and highbush blueberry, which makes tdp-glucose a potential biomarker for the consumption of these food products. Tdp-glucose exists in all living organisms, ranging from bacteria to humans.

   

UDP-3-O-(3-hydroxymyristoyl)-alpha-D-glucosamine

1-[(2R,3R,4S,5R)-5-[({[({[(2R,3R,4R,5S,6R)-3-amino-5-hydroxy-6-(hydroxymethyl)-4-{[(3R)-3-hydroxytetradecanoyl]oxy}oxan-2-yl]oxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-3,4-dihydroxyoxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-olate

C29H50N3O18P2 (790.2564)


Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine is slightly soluble (in water) and a moderately acidic compound (based on its pKa). Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine can be found in a number of food items such as chickpea, pineapple, sea-buckthornberry, and savoy cabbage, which makes udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine a potential biomarker for the consumption of these food products. Udp-3-o-(3-hydroxytetradecanoyl)-d-glucosamine may be a unique E.coli metabolite.

   

UDP-N-acetyl-alpha-D-glucosamine

N-[2-({[({[3,4-dihydroxy-5-(4-oxido-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]ethanecarboximidic acid

C17H25N3O17P2 (605.0659)


Udp-n-acetyl-alpha-d-glucosamine is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Udp-n-acetyl-alpha-d-glucosamine is soluble (in water) and a moderately acidic compound (based on its pKa). Udp-n-acetyl-alpha-d-glucosamine can be found in a number of food items such as daikon radish, napa cabbage, wasabi, and avocado, which makes udp-n-acetyl-alpha-d-glucosamine a potential biomarker for the consumption of these food products.

   

UDP-alpha-D-galactose

[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl {[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl phosphonato]oxy}phosphonate

C15H22N2O17P2 (564.0394)


Udp-alpha-d-galactose is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Udp-alpha-d-galactose is soluble (in water) and a moderately acidic compound (based on its pKa). Udp-alpha-d-galactose can be found in a number of food items such as hard wheat, sourdough, common pea, and mango, which makes udp-alpha-d-galactose a potential biomarker for the consumption of these food products.

   

UDP-alpha-D-sulfoquinovopyranose

(6-{[({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphinato]oxy}-3,4,5-trihydroxyoxan-2-yl)methanesulfonate

C15H21N2O19P2S (626.9934)


Udp-alpha-d-sulfoquinovopyranose is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Udp-alpha-d-sulfoquinovopyranose is soluble (in water) and an extremely strong acidic compound (based on its pKa). Udp-alpha-d-sulfoquinovopyranose can be found in a number of food items such as garland chrysanthemum, sesbania flower, feijoa, and sunburst squash (pattypan squash), which makes udp-alpha-d-sulfoquinovopyranose a potential biomarker for the consumption of these food products.

   

UDP-alpha-D-xylose

1-{3,4-dihydroxy-5-[({hydroxy[(3,4,5-trihydroxyoxan-2-yl)oxy]phosphoryl phosphonato}oxy)methyl]oxolan-2-yl}-2-oxo-1,2-dihydropyrimidin-4-olic acid

C14H20N2O16P2 (534.0288)


Udp-alpha-d-xylose is a member of the class of compounds known as pyrimidine ribonucleoside diphosphates. Pyrimidine ribonucleoside diphosphates are pyrimidine ribonucleotides with diphosphate group linked to the ribose moiety. Udp-alpha-d-xylose is soluble (in water) and a moderately acidic compound (based on its pKa). Udp-alpha-d-xylose can be found in a number of food items such as pak choy, turmeric, arrowhead, and agar, which makes udp-alpha-d-xylose a potential biomarker for the consumption of these food products.

   

UDP-beta-L-arabinofuranose

1-(5-{[({[3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}(hydroxy)phosphoryl phosphonato)oxy]methyl}-3,4-dihydroxyoxolan-2-yl)-2-oxo-1,2-dihydropyrimidin-4-olic acid

C14H20N2O16P2 (534.0288)


Udp-beta-l-arabinofuranose is a member of the class of compounds known as pyrimidine nucleotide sugars. Pyrimidine nucleotide sugars are pyrimidine nucleotides bound to a saccharide derivative through the terminal phosphate group. Udp-beta-l-arabinofuranose is soluble (in water) and a moderately acidic compound (based on its pKa). Udp-beta-l-arabinofuranose can be found in a number of food items such as turnip, leek, lowbush blueberry, and mammee apple, which makes udp-beta-l-arabinofuranose a potential biomarker for the consumption of these food products.