Common Name

Beta-D-Glucose Description

Beta-D-Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. It is used therapeutically in fluid and nutrient replacement. A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. This group contains a benzene and also an ethylene group, being derived from styrolene. Coniferin, C16H22O8, occurs in the cambium of conifer wood. Emlisin converts it into glucose and coniferyl alcohol, while oxidation gives glycovanillin, which yields with emlisin glucose and vanillin. Syringin, which occurs in the bark of Syringe vligaris, is a methoxyconiferin. Phloridzus occurs in the root-bark of various fruit trees; it hydrolyses to glucose and phloretin, which is the phloroglucin ester of paraoxyhydratropic acid. It is related to the pentosides naringin, C21HEOi1, which hydrolyses to rhamnose and naringenin, the phioroglucin ester of para-oxycinnamic acid, and hesperidin, which hydrolyses to rhamnose and hesperetin, the phloroglucin ester of meta-oxy-para-methoxycinnamic acid or isoferliic acid, C10H10O4. Classification of the glucosides is a matter of some difficlity. One based on the chemical constitution of the non-glucose part of the moleclies has been proposed that frames four groups: (I) ethylene derivatives, (2) benzene derivatives, (3) styrolene derivatives, (4) anthracene derivatives. A group may also be made to include the cyanogenetic glucosides, i.e. those containing prussic acid. Other classifications follow a botanical classification, which has several advantages; in particliar, plants of allied genera contain similar compounds. In this article the chemical classification will be followed, and only the more important compounds will be discussed here. Structure

Synonyms

Value Source GlucoseChEMBL b-D-GlucoseGenerator β-D-glucoseGenerator b-D-GlucopyranoseHMDB b-DextroseHMDB b-GlucoseHMDB beta-D-GlucopyranoseHMDB beta-delta-GlucopyranoseHMDB beta-DextroseHMDB beta-GlucoseHMDB D GlucoseMeSH Glucose, (beta-D)-isomerMeSH DextroseMeSH Glucose, (L)-isomerMeSH Monohydrate, glucoseMeSH Anhydrous dextroseMeSH Glucose, (DL)-isomerMeSH Glucose, (alpha-D)-isomerMeSH L GlucoseMeSH D-GlucoseMeSH Dextrose, anhydrousMeSH Glucose monohydrateMeSH L-GlucoseMeSH

Chemical Formlia

C6H12O6 Average Molecliar Weight

180.1559 Monoisotopic Molecliar Weight

180.063388116 IUPAC Name

(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol Traditional Name

glucoside CAS Registry Number

492-61-5 SMILES

OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O

InChI Identifier

InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6-/m1/s1

InChI Key

WQZGKKKJIJFFOK-VFUOTHLCSA-N Chemical Taxonomy Description

This compound belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. Kingdom

Organic compounds Super Class

Organic oxygen compounds Class

Organooxygen compounds Sub Class

Carbohydrates and carbohydrate conjugates Direct Parent

Hexoses Alternative Parents

  • Oxanes
  • Secondary alcohols
  • Hemiacetals
  • Polyols
  • Oxacyclic compounds
  • Primary alcohols
  • Hydrocarbon derivatives
  • Substituents

  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
  • Molecliar Framework

    Aliphatic heteromonocyclic compounds External Descriptors

  • D-glucopyranose (CHEBI:15903 )
  • Ontology Status

    Detected but not Quantified Origin

  • Endogenous
  • Biofunction

    Not Available Application

    Not Available Cellliar locations

  • Cytoplasm
  • Physical Properties State

    Solid Experimental Properties

    Property Value Reference Melting PointNot AvailableNot Available Boiling PointNot AvailableNot Available Water SolubilityNot AvailableNot Available LogP-3.24SANGSTER (1994)

    Predicted Properties

    Property Value Source Water Solubility782.0 mg/mLALOGPS logP-2.6ALOGPS logP-2.9ChemAxon logS0.64ALOGPS pKa (Strongest Acidic)11.3ChemAxon pKa (Strongest Basic)-3ChemAxon Physiological Charge0ChemAxon Hydrogen Acceptor Count6ChemAxon Hydrogen Donor Count5ChemAxon Polar Surface Area110.38 Å2ChemAxon Rotatable Bond Count1ChemAxon Refractivity35.92 m3·mol-1ChemAxon Polarizability16.43 Å3ChemAxon Number of Rings1ChemAxon Bioavailability1ChemAxon Rlie of FiveYesChemAxon Ghose FilterYesChemAxon Vebers RlieYesChemAxon MDDR-like RlieYesChemAxon

    Spectra Spectra

    Spectrum Type Description Splash Key Predicted GC-MS

    Predicted GC-MS Spectrum – GC-MSNot Available GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-00di-9721000000-6ca4df9ac892160d11c5View in MoNA GC-MS

    GC-MS Spectrum – GC-EI-TOFsplash10-00di-9621000000-fff85ff382393ec04a54View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09View in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baView in MoNA Predicted LC-MS/MS

    Predicted LC-MS/MS Spectrum – 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4View in MoNA MS

    Mass Spectrum (Electron Ionization)splash10-03kc-9000000000-a60df7b043f8947d6909View in MoNA

    Biological Properties Cellliar Locations

  • Cytoplasm
  • Biofluid Locations

  • Feces
  • Saliva
  • Tissue Location

    Not Available Pathways

    Name SMPDB Link KEGG Link Fanconi-bickel syndromeSMP00572Not Available Fructose-1,6-diphosphatase deficiencySMP00562Not Available GluconeogenesisSMP00128map00010 Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke DiseaseSMP00374Not Available Glycogenosis, Type IA. Von gierke diseaseSMP00581Not Available Glycogenosis, Type IBSMP00573Not Available Glycogenosis, Type ICSMP00574Not Available Glycogenosis, Type VII. Tarui diseaseSMP00531Not Available GlycolysisSMP00040map00010 Phosphoenolpyruvate carboxykinase deficiency 1 (PEPCK1)SMP00560Not Available Trehalose DegradationSMP00467Not Available Triosephosphate isomeraseSMP00563Not Available

    Normal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details FecesDetected but not Quantified Adlit (>18 years old)Both

    Normal

  • 18052033
  • details FecesDetected but not Quantified Adlit (>18 years old)Both

    Normal

  • 21330412
  • details FecesDetected but not Quantified Adlit (>18 years old)Both

    Normal

  • 21761941
  • details SalivaDetected but not Quantified Adlit (>18 years old)Not SpecifiedNormal

  • 12097436
  • details

    Abnormal Concentrations

    Biofluid Status Value Age Sex Condition Reference Details FecesDetected but not Quantified Adlit (>18 years old)Both

    Irritable bowel syndrome

  • 21330412
  • details FecesDetected but not Quantified Adlit (>18 years old)Both

    Irritable bowel syndrome

  • 21761941
  • details FecesDetected but not Quantified Adlit (>18 years old)Both

    Ulcerative colitis

  • 21761941
  • details

    Associated Disorders and Diseases Disease References

    None Associated OMIM IDs

    None External Links DrugBank ID

    Not Available DrugBank Metabolite ID

    Not Available Phenol Explorer Compound ID

    Not Available Phenol Explorer Metabolite ID

    Not Available FoodDB ID

    FDB011824 KNApSAcK ID

    Not Available Chemspider ID

    58238 KEGG Compound ID

    C00221 BioCyc ID

    Not Available BiGG ID

    Not Available Wikipedia Link

    Not Available NuGOwiki Link

    HMDB00516 Metagene Link

    HMDB00516 METLIN ID

    3755 PubChem Compound

    64689 PDB ID

    BGC ChEBI ID

    15903

    Product: BFH772

    References Synthesis Reference Wenck, Helmut; Kinedt, Claudia; Bader, Hans Joachim. Production of b-D-glucose. Praxis der Naturwissenschaften, Chemie (1986), 35(4), 23. Material Safety Data Sheet (MSDS) Not Available General References Not Available

    Enzymes

    General function:
    Involved in ATP binding
    Specific function:
    Catalyzes the initial step in utilization of glucose by the beta-cell and liver at physiological glucose concentration. Glucokinase has a high Km for glucose, and so it is effective only when glucose is abundant. The role of GCK is to provide G6P for the synthesis of glycogen. Pancreatic glucokinase plays an important role in modulating insulin secretion. Hepatic glucokinase helps to facilitate the uptake and conversion of glucose by acting as an insulin-sensitive determinant of hepatic glucose usage.
    Gene Name:
    GCK
    Uniprot ID:
    P35557
    Molecular weight:
    52191.07
    Reactions
    Adenosine triphosphate + Beta-D-Glucose → ADP + Beta-D-Glucose 6-phosphate details
    General function:
    Involved in ATP binding
    Specific function:
    Not Available
    Gene Name:
    HK3
    Uniprot ID:
    P52790
    Molecular weight:
    99024.56
    Reactions
    Adenosine triphosphate + Beta-D-Glucose → ADP + Beta-D-Glucose 6-phosphate details
    General function:
    Involved in ATP binding
    Specific function:
    Not Available
    Gene Name:
    HK2
    Uniprot ID:
    P52789
    Molecular weight:
    102379.06
    Reactions
    Adenosine triphosphate + Beta-D-Glucose → ADP + Beta-D-Glucose 6-phosphate details
    General function:
    Involved in ATP binding
    Specific function:
    Not Available
    Gene Name:
    HK1
    Uniprot ID:
    P19367
    Molecular weight:
    102485.1
    Reactions
    Adenosine triphosphate + Beta-D-Glucose → ADP + Beta-D-Glucose 6-phosphate details
    General function:
    Involved in 6-phosphogluconolactonase activity
    Specific function:
    Oxidizes glucose-6-phosphate and glucose, as well as other hexose-6-phosphates.
    Gene Name:
    H6PD
    Uniprot ID:
    O95479
    Molecular weight:
    88891.99
    Reactions
    Beta-D-Glucose + NAD(P)(+) → Gluconolactone + NAD(P)H details
    General function:
    Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
    Specific function:
    LPH splits lactose in the small intestine.
    Gene Name:
    LCT
    Uniprot ID:
    P09848
    Molecular weight:
    218584.77
    General function:
    Involved in phosphotransferase activity, alcohol group as acceptor
    Specific function:
    Catalyzes the phosphorylation of D-glucose to D-glucose 6-phosphate using ADP as the phosphate donor. GDP and CDP can replace ADP, but with reduced efficiency (By similarity).
    Gene Name:
    ADPGK
    Uniprot ID:
    Q9BRR6
    Molecular weight:
    53960.185
    Reactions
    Beta-D-Glucose + ADP → Beta-D-Glucose 6-phosphate + Adenosine monophosphate details
    General function:
    Involved in catalytic activity
    Specific function:
    Intestinal trehalase is probably involved in the hydrolysis of ingested trehalose.
    Gene Name:
    TREH
    Uniprot ID:
    O43280
    Molecular weight:
    66567.26
    Reactions
    Trehalose + Water → Beta-D-Glucose + Alpha-D-Glucose details
    General function:
    Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
    Specific function:
    Cleaves beta-linked terminal galactosyl residues from gangliosides, glycoproteins, and glycosaminoglycans.Isoform 2 has no beta-galactosidase catalytic activity, but plays functional roles in the formation of extracellular elastic fibers (elastogenesis) and in the development of connective tissue. Seems to be identical to the elastin-binding protein (EBP), a major component of the non-integrin cell surface receptor expressed on fibroblasts, smooth muscle cells, chondroblasts, leukocytes, and certain cancer cell types. In elastin producing cells, associates with tropoelastin intracellularly and functions as a recycling molecular chaperone which facilitates the secretions of tropoelastin and its assembly into elastic fibers.
    Gene Name:
    GLB1
    Uniprot ID:
    P16278
    Molecular weight:
    Not Available
    General function:
    Involved in catalytic activity
    Specific function:
    Not Available
    Gene Name:
    GBA
    Uniprot ID:
    P04062
    Molecular weight:
    59715.745
    General function:
    Involved in enzyme inhibitor activity
    Specific function:
    Inhibits glucokinase by forming an inactive complex with this enzyme
    Gene Name:
    GCKR
    Uniprot ID:
    Q14397
    Molecular weight:
    68700.7
    General function:
    Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
    Specific function:
    Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
    Gene Name:
    GBA3
    Uniprot ID:
    Q9H227
    Molecular weight:
    Not Available
    Reactions
    Cellobiose + Water → Beta-D-Glucose details Cellulose + Water → Cellulose + Beta-D-Glucose details Dhurrin + Water → (S)-4-Hydroxymandelonitrile + Beta-D-Glucose details Lotaustralin + Water → (2R)-2-Hydroxy-2-methylbutanenitrile + Beta-D-Glucose details Linamarin + Water → Acetone cyanohydrin + Beta-D-Glucose details
    General function:
    Involved in catalytic activity
    Specific function:
    May serve as an alternate pathway for starch digestion when luminal alpha-amylase activity is reduced because of immaturity or malnutrition. May play a unique role in the digestion of malted dietary oligosaccharides used in food manufacturing.
    Gene Name:
    MGAM
    Uniprot ID:
    O43451
    Molecular weight:
    Not Available
    General function:
    Involved in isomerase activity
    Specific function:
    Mutarotase converts alpha-aldose to the beta-anomer. It is active on D-glucose, L-arabinose, D-xylose, D-galactose, maltose and lactose (By similarity).
    Gene Name:
    GALM
    Uniprot ID:
    Q96C23
    Molecular weight:
    37765.365
    Reactions
    Alpha-D-Glucose → Beta-D-Glucose details
    General function:
    Not Available
    Specific function:
    Not Available
    Gene Name:
    HKDC1
    Uniprot ID:
    Q2TB90
    Molecular weight:
    102513.88
    Reactions
    Adenosine triphosphate + Beta-D-Glucose → ADP + Beta-D-Glucose 6-phosphate details

    PMID: 26366439