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Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-05-23 00:28:27 UTC
HMDB IDHMDB0000516
Secondary Accession Numbers
  • HMDB0003340
  • HMDB00516
  • HMDB0062170
  • HMDB03340
  • HMDB62170
Metabolite Identification
Common Namebeta-D-Glucose
Descriptionbeta-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. Classification of the glucosides is quite difficult. One system based on the chemical constitution of the non-glucose part of the molecules has been proposed. This system outlines four groups: (1) ethylene derivatives, (2) benzene derivatives, (3) styrolene derivatives, and (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 particular, plants of allied genera contain similar compounds.
Structure
Data?1558571307
Synonyms
ValueSource
beta-D-GlucopyranoseKegg
b-D-GlucopyranoseGenerator
b-D-GlucoseGenerator
Β-D-glucoseGenerator
GlucoseHMDB
b-DextroseHMDB
b-GlucoseHMDB
beta-delta-GlucopyranoseHMDB
beta-DextroseHMDB
beta-GlucoseHMDB
D GlucoseHMDB
Glucose, (beta-D)-isomerHMDB
DextroseHMDB
Monohydrate, glucoseHMDB
Anhydrous dextroseHMDB
Glucose, (DL)-isomerHMDB
Glucose, (alpha-D)-isomerHMDB
D-GlucoseHMDB
Dextrose, anhydrousHMDB
Glucose monohydrateHMDB
D-GlucopyranoseHMDB
D-GlucopyranosideHMDB
beta-D-GlucopyranosideHMDB
beta-D-GlucoseHMDB
β-D-GlucopyranosideHMDB
β-DextroseHMDB
β-GlucoseHMDB
Chemical FormulaC6H12O6
Average Molecular Weight180.1559
Monoisotopic Molecular Weight180.063388116
IUPAC Name(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional Nameglucoside
CAS Registry Number492-61-5
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 KeyWQZGKKKJIJFFOK-VFUOTHLCSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexoses
Alternative Parents
Substituents
  • Hexose monosaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP-3.24SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility782 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.92 m³·mol⁻¹ChemAxon
Polarizability16.35 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9721000000-6ca4df9ac892160d11c5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9621000000-fff85ff382393ec04a54JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9721000000-6ca4df9ac892160d11c5JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9621000000-fff85ff382393ec04a54JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0np0-9700000000-e8d638dc817e46b97d7bJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-004i-6122690000-eaf6f7adf34ccd0c667bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4JSpectraViewer | MoNA
MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-a60df7b043f8947d6909JSpectraViewer | MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)MaleNormal details
FecesDetected but not Quantified Adult (>18 years old)FemaleNormal details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
FecesDetected but not Quantified Adult (>18 years old)Both
Normal
details
SalivaDetected but not Quantified Adult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Adult (>18 years old)MaleGout details
FecesDetected but not Quantified Adult (>18 years old)Femaleankylosing spondylitis details
FecesDetected but not Quantified Adult (>18 years old)Femalerheumatoid arthritis details
FecesDetected but not Quantified Adult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not Quantified Adult (>18 years old)Both
Irritable bowel syndrome
details
FecesDetected but not Quantified Adult (>18 years old)Both
Ulcerative colitis
details
Associated Disorders and Diseases
Disease References
Irritable bowel syndrome
  1. Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
  2. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Ulcerative colitis
  1. Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
Gout
  1. Shao T, Shao L, Li H, Xie Z, He Z, Wen C: Combined Signature of the Fecal Microbiome and Metabolome in Patients with Gout. Front Microbiol. 2017 Feb 21;8:268. doi: 10.3389/fmicb.2017.00268. eCollection 2017. [PubMed:28270806 ]
Rheumatoid arthritis
  1. Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70 [Link]
Associated OMIM IDs
DrugBank IDDB02379
Phenol Explorer Compound IDNot Available
FoodDB IDFDB011824
KNApSAcK IDNot Available
Chemspider ID58238
KEGG Compound IDC00221
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID3755
PubChem Compound64689
PDB IDNot Available
ChEBI ID15903
References
Synthesis ReferenceWenck, 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
  1. Siewert G, Westphal O: [New synthesis of 3,6-didesoxy-D-xylo-hexose (abequose)]. Justus Liebigs Ann Chem. 1969;720:171-6. [PubMed:5798985 ]
  2. ZORBACH WW, CIAUDELLI JP: 2-DEOXY SUGARS. IV. 2,6-DIDEOXY-D-ARABINO-HEXOSE. J Org Chem. 1965 Feb;30:451-2. [PubMed:14267295 ]
  3. Horton D, Weckerle W: Synthesis of 3-amino-2,3,6-trideoxy-D-ribo-hexose hydrochloride. Carbohydr Res. 1976 Feb;46(2):227-35. [PubMed:1260789 ]
  4. Walker TE, Ehler DS, Unkefer CJ: Synthesis of 2-deoxy-D-arabino-(6-13C)hexose. Carbohydr Res. 1988 Oct 1;181:125-34. [PubMed:3208249 ]
  5. Fahrenheim G, Westphal O: [Para-nitro-phenylglycoside from 3-desoxy-D-arabino-, -D-ribo- and -D-xylo-hexose]. Justus Liebigs Ann Chem. 1969;720:177-87. [PubMed:5798986 ]
  6. Lehmann J, Schroter E: [Enzymatic conversion of 2-deoxy-D-lyxo-hexose (2-deoxy-D-galactose) to 3,6-anhydro-2-deoxy-D-lyxo-hexose (D-isogalactal)]. Carbohydr Res. 1974 Sep;36(2):303-10. [PubMed:4609608 ]
  7. Baer HH, Georges FF: A synthesis of 3-amino-2,3,6-trideoxy-D-ribo-hexose (D-ristosamine) hydrochloride. Carbohydr Res. 1977 May;55:253-8. [PubMed:193644 ]
  8. Kulhanek M, Tadra M, Linek K, Kucar S: 2-Deoxy-D-lyxo-hexonic acid from 2-deoxy-D-lyxo-hexose by Pseudomonas aeruginosa fermentation. Folia Microbiol (Praha). 1979;24(2):185-7. [PubMed:110658 ]
  9. Scruel O, Sener A, Malaisse WJ: Hexose metabolism in pancreatic islets: effect of D-glucose upon D-fructose metabolism. Mol Cell Biochem. 1999 Jul;197(1-2):209-16. [PubMed:10485341 ]
  10. Brimacombe JS, Portsmouth D: A synthesis of chromose D (3-O-acetyl-2,6-dideoxy-D-lyxo-hexose). Chem Ind. 1965 Mar 13;11:468. [PubMed:5825537 ]

Only showing the first 10 proteins. There are 16 proteins in total.

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-phosphatedetails
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-phosphatedetails
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-phosphatedetails
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-phosphatedetails
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)Hdetails
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 monophosphatedetails
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-Glucosedetails
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91
Reactions
beta-D-Glucose → 4-O-alpha-D-Glucopyranuronosyl-D-galactosedetails
beta-D-Glucose → 3-O-beta-D-Galactopyranuronosyl-D-galactosedetails
beta-D-Glucose → 2-O-beta-D-Glucopyranuronosyl-D-mannosedetails
beta-D-Glucose → Acaciabiuronic aciddetails
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

Only showing the first 10 proteins. There are 16 proteins in total.