Classification Term: 3745

Monosaccharides (ontology term: CHEMONTID:0001540)

Compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn." []

found 50 associated metabolites at category metabolite taxonomy ontology rank level.

Ancestor: Carbohydrates and carbohydrate conjugates

Child Taxonomies: Trioses, Tetroses, Pentoses, Hexoses, Heptoses, Octoses, Nonoses, Monosaccharide phosphates, Monosaccharide sulfates

1,5-anhydroglucitol (1,5-AG)

(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-3,4,5-triol

C6H12O5 (164.0685)


1,5-Anhydrosorbitol or 1,5-anhydroglucitol (1,5-AG) is a validated marker of short-term glycemic control. This substance is derived mainly from food, is well absorbed in the intestine, and is distributed to all organs and tissues. It is metabolically stable, being excreted in the urine when its level exceeds the renal threshold. It is reabsorbed in the renal tubules, and is competitively inhibited by glucosuria, which leads to a reduction in its level in serum. The correlation between this reduction and the amount of glucose present in urine is so close that 1,5 AG can be used as a sensitive, day-to-day, real-time marker of glycemic control. It provides useful information on current glycemic control and is superior to both hemoglobin A1C and fructosamine in detecting near-normoglycemia. 1,5-AG in human plasma has been proposed for several years as a short-term, retrospective marker of glycaemic control and seems to be the most suitable parameter for monitoring glucose excursions. The decrease in serum 1,5-AG is very sensitive to urinary glucose excretion. It is a metabolically inert polyol that competes with glucose for reabsorption in the kidneys. Otherwise stable levels of 1,5-AG are rapidly depleted as blood glucose levels exceed the renal threshold for glucosuria. 1,5-AG is also more tightly associated with glucose fluctuations and postprandial glucose. (PMID: 18088226, 12166605, 7783360, 8940824) [HMDB] 1, 5-Anhydrosorbitol or 1,5-anhydroglucitol (1,5-AG) is a validated marker of short-term glycemic control. This substance is derived mainly from food, is well absorbed in the intestine, and is distributed to all organs and tissues. It is metabolically stable, being excreted in the urine when its level exceeds the renal threshold. It is reabsorbed in the renal tubules and is competitively inhibited by glucosuria, which leads to a reduction in its level in serum. The correlation between this reduction and the amount of glucose present in urine is so close that 1,5 AG can be used as a sensitive, day-to-day, real-time marker of glycemic control. It provides useful information on current glycemic control and is superior to both hemoglobin A1C and fructosamine in detecting near-normoglycemia. 1,5-AG in human plasma has been proposed for several years as a short-term, retrospective marker of glycemic control and seems to be the most suitable parameter for monitoring glucose excursions. The decrease in serum 1,5-AG is very sensitive to urinary glucose excretion. It is a metabolically inert polyol that competes with glucose for reabsorption in the kidneys. Otherwise stable levels of 1,5-AG are rapidly depleted as blood glucose levels exceed the renal threshold for glucosuria. 1,5-AG is also more tightly associated with glucose fluctuations and postprandial glucose (PMID:18088226, 12166605, 7783360, 8940824). 1,5-Anhydrosorbitol is a short-term marker for glycemic control. 1,5-Anhydrosorbitol is a short-term marker for glycemic control.

   

(3R,4R,5R)-1,3,4,5,6-Pentahydroxyhexan-2-one

(3R,4S,5R)-1,3,4,5,6-pentahydroxyhexan-2-one

C6H12O6 (180.0634)


   

Glyceraldehyde

(2R)-2,3-dihydroxypropanal

C3H6O3 (90.0317)


DL-Glyceraldehyde is a monosaccharide. DL-Glyceraldehyde is the simplest aldose. DL-Glyceraldehyde can be used for various biochemical studies[1].

   

Dihydroxyacetone

Summers brand OF dihydroxyacetone

C3H6O3 (90.0317)


Dihydroxyacetone, also known as 1,3-dihydroxy-2-propanone or glycerone, is a member of the class of compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. Dihydroxyacetone is soluble (in water) and a very weakly acidic compound (based on its pKa). Dihydroxyacetone can be found in a number of food items such as cauliflower, green bell pepper, black cabbage, and sweet basil, which makes dihydroxyacetone a potential biomarker for the consumption of these food products. Dihydroxyacetone can be found primarily in urine, as well as in human muscle and stratum corneum tissues. Dihydroxyacetone exists in all living species, ranging from bacteria to humans. Dihydroxyacetone is primarily used as an ingredient in sunless tanning products. It is often derived from plant sources such as sugar beets and sugar cane, and by the fermentation of glycerin . Dihydroxyacetone (also known as DHA) is a ketotriose compound. Its addition to blood preservation solutions results in better maintenance of 2,3-diphosphoglycerate levels during storage. It is readily phosphorylated to dihydroxyacetone phosphate by triokinase in erythrocytes. In combination with naphthoquinones, it acts as a sunscreening agent. Dihydroxyacetone is the simplest of all ketoses and, having no chiral centre, is the only one that has no optical activity. Dihydroxyacetone is a simple non-toxic sugar. It is often derived from plant sources such as sugar beets and sugar cane, by the fermentation of glycerin. Dihydroxyacetone is a white crystalline powder which is water soluble. 1,3-Dihydroxyacetone (DHA), the main active ingredient in sunless tanning skin-care preparations and an important precursor for the synthesis of various fine chemicals, is produced on an industrial scale by microbial fermentation of glycerol over Gluconobacter oxydans[1]. 1,3-Dihydroxyacetone (DHA), the main active ingredient in sunless tanning skin-care preparations and an important precursor for the synthesis of various fine chemicals, is produced on an industrial scale by microbial fermentation of glycerol over Gluconobacter oxydans[1].

   

Tartronate semialdehyde

2-hydroxy-3-oxopropanoic acid

C3H4O4 (104.011)


Tartronate semialdehyde is an intermediate in ascorbate and aldarate as well as glyoxylate and dicarboxylate metabolism. It is generated from 2-dehydro-3-deoxy-D-glucarate and 5-dehydro-4-deoxy-D-glucarate via the enzyme 2-dehydro-3-deoxyglucarate aldolase [EC:4.1.2.20]. [HMDB]. Tartronate semialdehyde is found in many foods, some of which are wild leek, common salsify, sunflower, and new zealand spinach. Tartronate semialdehyde is an intermediate in ascorbate and aldarate as well as glyoxylate and dicarboxylate metabolism. It is generated from 2-dehydro-3-deoxy-D-glucarate and 5-dehydro-4-deoxy-D-glucarate via the enzyme 2-dehydro-3-deoxyglucarate aldolase [EC:4.1.2.20].

   

L-Erythrulose

(3S)-1,3,4-Trihydroxybutan-2-one

C4H8O4 (120.0423)


L-Erythrulose is an extremely reactive ketose, which rapidly glycates and crosslinks proteins, and therefore may mediate the(L-ascorbate) AsA-dependent modification of protein (ascorbylation) seen in vitro, and also proposed to occur in vivo in human lens during diabetic and age-onset cataract formation.(PMID: 10727845) [HMDB] L-Erythrulose is an extremely reactive ketose, which rapidly glycates and crosslinks proteins, and therefore may mediate the(L-ascorbate) AsA-dependent modification of protein (ascorbylation) seen in vitro, and also proposed to occur in vivo in human lens during diabetic and age-onset cataract formation.(PMID: 10727845).

   

3-Mercaptolactic acid

(R)-2-hydroxy-3-mercaptopropanoic acid

C3H6O3S (122.0038)


3-Mercaptolactic acid is a thiol that has been confirmed to be found in urine (PMID 8852041). [HMDB] 3-Mercaptolactic acid is a thiol that has been confirmed to be found in urine (PMID 8852041).

   

Alphachloralose

1-[6-hydroxy-2-(trichloromethyl)-tetrahydro-2H-furo[2,3-d][1,3]dioxol-5-yl]ethane-1,2-diol

C8H11Cl3O6 (307.9621)


D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D006993 - Hypnotics and Sedatives D002491 - Central Nervous System Agents > D002492 - Central Nervous System Depressants > D000777 - Anesthetics Bird repellant in grain seed

   

L-Sorbose

(2R,3S,4R,5S)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol

C6H12O6 (180.0634)


L-Sorbose, also known as L-sorbinose or L-xylo-hexulose, belongs to the class of organic compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. L-Sorbose exists in all living species, ranging from bacteria to humans. The commercial production of vitamin C (ascorbic acid) often begins with sorbose. L-Sorbose (CAS: 87-79-6) is a ketose belonging to the group of sugars known as monosaccharides. Sorbose has been found to be a metabolite of Ketogulonicigenium (PMID:15785002). Indirect food additive arising from its use as a constituent of cotton, cotton fabrics, paper and paperboard in contact with dry food

   

D-Tagatose

(2R,3S,4S,5R)-2-(hydroxymethyl)oxane-2,3,4,5-tetrol

C6H12O6 (180.0634)


D-Tagatose (CAS: 87-81-0), a rare natural hexoketose, is an isomer of D-galactose. D-Tagatose occurs naturally in Sterculia setigera gum, and it is also found in small quantities in various foods such as sterilized and powdered cows milk, hot cocoa, and a variety of cheeses, yogurts, and other dairy products. It can be synthesized from D-galactose by isomerization under alkaline conditions in the presence of calcium. D-Tagatose has numerous health benefits, including promotion of weight loss; no glycemic effect; anti-plaque, non-cariogenic, anti-halitosis, prebiotic, and anti-biofilm properties; organ transplants; enhancement of flavor; improvement of pregnancy and fetal development; obesity treatment; and reduction in symptoms associated with type 2 diabetes, hyperglycemia, anemia, and hemophilia (PMID:17492284). GRAS status for use as a sweetener, humectant, texturiser or stabiliser in food, especies low calorie products D064449 - Sequestering Agents > D002614 - Chelating Agents > D007502 - Iron Chelating Agents

   

(2R,4S,5S)-1,2,4,5,6-Pentahydroxyhexan-3-one

1,2,4,5,6-pentahydroxyhexan-3-one

C6H12O6 (180.0634)


   

D-altro-D-manno-Heptose

2-(4-(Hydroxy(oxido)amino)benzylidene)malononitrile

C7H14O7 (210.0739)


D-altro-D-manno-Heptose is found combined in bakers yeas D000970 - Antineoplastic Agents > D020032 - Tyrphostins

   

Fructosamine

(2R,3S,4R,5R)-2-(aminomethyl)oxane-2,3,4,5-tetrol

C6H13NO5 (179.0794)


Fructosamine is a compound which can be considered as the result of a reaction between fructose and ammonia or an amine (with a molecule of water being released). A fructosamine is also formed when carbonyl group of glucose reacts with an amino group of a protein, as the double bond to oxygen moves from the end carbon atom to the next carbon atom and water is released. Fructosamines formed from blood proteins such as serum albumin are known as Glycated Serum Protein (GSP) or Glycated Albumin, and are used to identify the plasma glucose concentration over time and so assess diabetic control (wikipedia). Glucose molecules are joined to protein molecules to form stable ketoamines, or fructosamines, through glycation, a nonenzymatic mechanism involving a labile Schiff base intermediate and the Amadori rearrangement. The amount of fructosamine in serum is increased in diabetes mellitus owing to the abnormally high concentration of sugar in blood. The concentration of fructosamine in serum thus reflects the degree of glycemic control attained by the diabetic patient and is useful in monitoring the effectiveness of therapy in diabetes over a period of several weeks, in a manner analogous to the determination of glycated hemoglobin. Of the analytical approaches used to measure fructosamine, affinity chromatography with m-aminophenylboronic acid and the nitroblue tetrazolium reduction method appear to be the most practical means for clinical chemists to assay fructosamine quickly, economically, and accurately. Fructosamine values can readily distinguish normal individuals and diabetic patients in good glycemic control from diabetics in poor control. Unlike glycated hemoglobin, which reflects the average blood sugar concentration over the past six to eight weeks, fructosamine reflects the average blood sugar concentration over the past two to three weeks. Thus a clinical advantage is that fructosamine responds more quickly to changes in therapy, thereby allowing for improved glycemic control. Fructosamine is used in conjunction with determinations of blood sugar and (or) of glycated hemoglobin, or by itself, the fructosamine assay can provide clinically useful information for the detection and control of diabetes (PMID: 3319287). Fructosamine is found to be associated with 11-beta-hydroxylase deficiency, which is an inborn error of metabolism. Fructosamine is a compound which can be considered as the result of a reaction between fructose and ammonia or an amine (with a molecule of water being released). A fructosamine is also formed when carbonyl group of glucose reacts with an amino group of a protein, as the double bond to oxygen moves from the end carbon atom to the next carbon atom and water is released. Fructosamines formed from blood proteins such as serum albumin are known as Glycated Serum Protein (GSP) or Glycated Albumin, and are used to identify the plasma glucose concentration over time and so assess diabetic control. (wikipedia)

   

Lacto-N-decaose

N-[(3R,5S,6R)-6-Ethyl-4-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-2-{[(3R,5R)-2-({[(3R,4R,6R)-6-ethyl-5-{[(3R,5R,6S)-4-{[(3R,5S,6R)-6-ethyl-4-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-5-methyloxan-2-yl]oxy}-6-({[(3R,4R,6R)-6-ethyl-5-{[(3R,4S,5R,6R)-6-ethyl-3,4,5-trimethyloxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-methyloxan-2-yl]oxy}methyl)-3,5-dimethyloxan-2-yl]oxy}-3-[(1-hydroxyethylidene)amino]-4-methyloxan-2-yl]oxy}methyl)-3,5-dimethyl-6-{[(2R,4R,5R)-2,4,5,6-tetramethyloxan-3-yl]oxy}oxan-4-yl]oxy}-5-methyloxan-3-yl]ethanimidate

C95H168N4O23 (1733.2099)


Lacto-N-decaose is an oligosaccharide characterized in breast milk. Oligosaccharides in human milk represent a group of bioactive molecules that have evolved to be an abundant and diverse component of human milk, even though they have no direct nutritive value to the infant. A recent hypothesis proposes that they could be substrates for the development of the intestinal microflora and the mucosal immune system. (PMID: 15629115, 11787695, 14530096, 17002410) [HMDB] Lacto-N-decaose is an oligosaccharide characterized in breast milk. Oligosaccharides in human milk represent a group of bioactive molecules that have evolved to be an abundant and diverse component of human milk, even though they have no direct nutritive value to the infant. A recent hypothesis proposes that they could be substrates for the development of the intestinal microflora and the mucosal immune system. (PMID: 15629115, 11787695, 14530096, 17002410).

   

1-Methoxy-3-methylene-2-pentanone

1-methoxy-3-methylidenepentan-2-one

C7H12O2 (128.0837)


1-Methoxy-3-methylene-2-pentanone is found in fruits. 1-Methoxy-3-methylene-2-pentanone is a constituent of Actinidia chinensis (kiwi fruit), Phaseolus lunatus (butter bean) and Jasminum sambac (Arabian Jasmine)

   

(±)-5-Hydroxy-4-octanone

5-hydroxyoctan-4-one

C8H16O2 (144.115)


(±)-5-Hydroxy-4-octanone is a flavouring agent Flavouring agent

   

7-(1,3-Cyclohexadienyl)-5-hydroxy-2,6-dimethyl-2-hepten-4-one

7-(cyclohexa-1,3-dien-1-yl)-5-hydroxy-2,6-dimethylhept-2-en-4-one

C15H22O2 (234.162)


7-(1,3-Cyclohexadienyl)-5-hydroxy-2,6-dimethyl-2-hepten-4-one is found in herbs and spices. 7-(1,3-Cyclohexadienyl)-5-hydroxy-2,6-dimethyl-2-hepten-4-one is a constituent of the oil of turmeric, Curcuma longa. Constituent of the oil of turmeric, Curcuma longa. 7-(1,3-Cyclohexadienyl)-5-hydroxy-2,6-dimethyl-2-hepten-4-one is found in herbs and spices.

   

1-Hydroxy-2-pentanone

1-hydroxypentan-2-one

C5H10O2 (102.0681)


1-hydroxy-2-pentanone belongs to the family of Alpha Ketoaldehydes. These are organic compounds containing an aldehyde substituted with a keto group on the adjacent carbon.

   
   

(2R,3S,4R,5R)-2,3,4,5,6-Pentahydroxyhexanoyl Fluoride

2,3,4,5,6-pentahydroxyhexanoyl fluoride

C6H11FO6 (198.054)


   

(2R,4R,5R)-2,4,5,6-Tetrahydroxy-1-sulfanylhexan-3-one

(2R,4R,5R)-2,4,5,6-Tetrahydroxy-1-sulphanylhexan-3-one

C6H12O5S (196.0405)


   

1,5-Anhydro-d-mannitol

2-(hydroxymethyl)oxane-3,4,5-triol

C6H12O5 (164.0685)


1,5-anhydro-d-mannitol, also known as 1,5-sorbitan or 1-deoxy-D-glucopyranose, is a member of the class of compounds known as monosaccharides. Monosaccharides are compounds containing one carbohydrate unit not glycosidically linked to another such unit, and no set of two or more glycosidically linked carbohydrate units. Monosaccharides have the general formula CnH2nOn. 1,5-anhydro-d-mannitol is very soluble (in water) and a very weakly acidic compound (based on its pKa). 1,5-anhydro-d-mannitol can be found in a number of food items such as half-highbush blueberry, deerberry, vaccinium (blueberry, cranberry, huckleberry), and amaranth, which makes 1,5-anhydro-d-mannitol a potential biomarker for the consumption of these food products.

   

2-Hydroxy-4-methylthiobutyric acid

2-hydroxypentanethioic S-acid

C5H10O2S (134.0401)


   

2,3-Dihydroxypropanamide

2,3-Dihydroxypropanimidate

C3H7NO3 (105.0426)


   

3-O-Methyl-D-glucopyranose

6-(hydroxymethyl)-4-methoxyoxane-2,3,5-triol

C7H14O6 (194.079)


   

4-Amino-4-deoxyarabinose

4-amino-2,3,5-trihydroxypentanal

C5H11NO4 (149.0688)


   

5-Deoxy-D-ribose

2,3,4-trihydroxypentanal

C5H10O4 (134.0579)


   

5-Thio-D-Glucose

Ethyl4-acetyl-2-amino-5-methyl-3-furoate

C6H12O5S (196.0405)


   

arachidonoylethanolamine

1-amino-2-hydroxydocosa-7,10,13,16-tetraen-3-one

C22H37NO2 (347.2824)


   

D-Erythrose

Erythrose, (S-(r*,s*))-isomer

C4H8O4 (120.0423)


   

D-Psicose

2-(hydroxymethyl)oxane-2,3,4,5-tetrol

C6H12O6 (180.0634)


   

D-Threo-3-Pentulose

1,2,4,5-Tetrahydroxy-3-pentanone

C5H10O5 (150.0528)


   

Diethylaminoethyl-Sephacel

3-[2-(diethylamino)ethoxy]-6-{[2-(diethylamino)ethoxy]methyl}oxane-2,4,5-triol

C18H38N2O6 (378.273)


   

Docosahexaenoylethanolamine

1-amino-2-hydroxytetracosa-4,6,8,10,12,14-hexaen-3-one

C24H37NO2 (371.2824)


   

D-Gluconamide

2,3,4,5,6-pentahydroxyhexanamide

C6H13NO6 (195.0743)


   

Glycerylphosphorylinositol

7-(2,3-dihydroxypropanoyl)-1,2,3,4,5,6-hexahydroxy-7lambda5-phosphabicyclo[4.1.0]heptan-7-one

C9H15O10P (314.0403)


   

(2R,4R,5R)-1-Fluoro-1,2,4,5,6-pentahydroxyhexan-3-one

1-fluoro-1,2,4,5,6-pentahydroxyhexan-3-one

C6H11FO6 (198.054)


   

(2R,4R,5S)-1,4,5,6-Tetrahydroxy-2-sulfanylhexan-3-one

(2R,4R,5S)-1,4,5,6-Tetrahydroxy-2-sulphanylhexan-3-one

C6H12O5S (196.0405)


   

(2R,5S)-5-Amino-1,2,6,7-tetrahydroxyoctane-3,4-dione

5-amino-1,2,6,7-tetrahydroxyoctane-3,4-dione

C8H15NO6 (221.0899)


   

(4R,5R)-1-Aminooxy-2,4,5,6-tetrahydroxyhexan-3-one

1-(aminooxy)-2,4,5,6-tetrahydroxyhexan-3-one

C6H13NO6 (195.0743)


   

2,3,4,5-Tetrahydroxy-6-(1,2,3,4-tetrahydroxybutyl)oxane-2-carbaldehyde

2,3,4,5-tetrahydroxy-6-(1,2,3,4-tetrahydroxybutyl)oxane-2-carbaldehyde

C10H18O10 (298.09)


   

Palmitoylethanolamine

1-amino-2-hydroxyoctadecan-3-one

C18H37NO2 (299.2824)


   

Phosphohexose

6-(hydroxymethyl)-2-phosphooxane-2,3,4,5-tetrol

C6H11O8P (242.0192)


   

Pugnac

N-[4,5-Dihydroxy-6-(hydroxymethyl)-2-{[(phenyl-C-hydroxycarbonimidoyl)oxy]imino}oxan-3-yl]ethanimidate

C15H19N3O7 (353.1223)


   

1,4-Dihydroxy-3,3-dimethylbutan-2-one

1,4-dihydroxy-3,3-dimethylbutan-2-one

C6H12O3 (132.0786)


   

Zanosar

2,4,5-Trihydroxy-6-(hydroxymethyl)-N-methyl-N-nitrosooxane-3-carbamimidate

C8H15N3O7 (265.091)


   

Thioglucose

2,3,4,5,6-pentahydroxyhexanethial

C6H12O5S (196.0405)


   

6-(1,2,3,4-Tetrahydroxybutyl)oxane-2,3,4,5-tetrol

6-(1,2,3,4-tetrahydroxybutyl)oxane-2,3,4,5-tetrol

C9H18O9 (270.0951)


   

Xylan

(2R,3R,5S,6S)-tetrahydropyran-2,3,4,5,6-pentol

C5H10O6 (166.0477)


Xylan is a group of hemicelluloses, representing the third most abundant biopolymer on Earth. It is found in plants, in the secondary cell walls of dicotyledonous plants and in all cell walls of grasses (monocotyledonous). Xylans are polysaccharides made up of β-1,4-linked xylose (a pentose sugar) residues with side branches of α-arabinofuranose and α-glucuronic acids and contribute to cross-linking of cellulose microfibrils and lignin through ferulic acid residues. On the basis of the substituting groups, xylan can be categorized into three classes i) glucuronoxylan (GX) ii) neutral arabinoxylan (AX) and iii) glucuronoarabinoxylan (GAX). The quality of cereal flours and the hardness of dough are largely affected by the amount of xylan. Xylan is one of the foremost anti-nutritional factors in commonly used feedstuff raw materials. It is a major component of plant secondary cell walls which is a major source of renewable energy especially for second generation biofuels. However, since microorganisms like yeast cannot ferment pentoses naturally, xylose (the pentose backbone of xylan) results hard to ferment in biofuel production, reducing its use in renewable energy production (PMID: 18299887, PMID: 31077637). Occurs in all land plants, component of dietary roughage

   

alpha-D-xylose 1-phosphate

3,4,5-Trihydroxyoxan-2-yl phosphoric acid

C5H9O8P (228.0035)


beta-l-arabinose 1-phosphate is soluble (in water) and a moderately acidic compound (based on its pKa). beta-l-arabinose 1-phosphate can be found in a number of food items such as climbing bean, rubus (blackberry, raspberry), loganberry, and garland chrysanthemum, which makes beta-l-arabinose 1-phosphate a potential biomarker for the consumption of these food products.