Human Metabolome Database Version 3.5

Showing metabocard for Beta-D-Glucose (HMDB00516)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-04-19 16:40:22 -0600
HMDB ID HMDB00516
Secondary Accession Numbers
  • HMDB03340
Metabolite Identification
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. Emulsin converts it into glucose and coniferyl alcohol, while oxidation gives glycovanillin, which yields with emulsin glucose and vanillin. Syringin, which occurs in the bark of Syringe vulgaris, 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 isoferulic acid, C10H10O4. Classification of the glucosides is a matter of some difficulty. One based on the chemical constitution of the non-glucose part of the molecules 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 particular, 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 Thumb
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. b-D-Glucopyranose
  2. b-Dextrose
  3. b-Glucose
  4. beta-D-Glucopyranose
  5. beta-D-Glucose
  6. beta-delta-Glucopyranose
  7. beta-Dextrose
  8. beta-Glucose
Chemical Formula C6H12O6
Average Molecular Weight 180.1559
Monoisotopic Molecular Weight 180.063388116
IUPAC Name (2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC 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
Kingdom Organic Compounds
Super Class Carbohydrates and Carbohydrate Conjugates
Class Monosaccharides
Sub Class Hexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • D-galactopyranose(ChEBI)
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
Direct Parent Hexoses
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
Biofunction Not Available
Application Not Available
Cellular locations
  • Cytoplasm
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point Not Available Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP -3.24 SANGSTER (1994)
Predicted Properties
Property Value Source
Water Solubility 782 g/L ALOGPS
LogP -2.57 ALOGPS
LogP -2.9 ChemAxon
LogS 0.64 ALOGPS
pKa (strongest acidic) 11.3 ChemAxon
pKa (strongest basic) -3 ChemAxon
Hydrogen Acceptor Count 6 ChemAxon
Hydrogen Donor Count 5 ChemAxon
Polar Surface Area 110.38 A2 ChemAxon
Rotatable Bond Count 1 ChemAxon
Refractivity 35.92 ChemAxon
Polarizability 16.43 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 0 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid Locations Not Available
Tissue Location Not Available
Pathways
Name SMPDB Link KEGG Link
Glycolysis SMP00040 map00010 Link_out
Gluconeogenesis SMP00128 map00010 Link_out
Trehalose Degradation SMP00467 Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
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 Link_out
KEGG Compound ID C00221 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB00516 Link_out
Metagene Link HMDB00516 Link_out
METLIN ID 3755 Link_out
PubChem Compound 64689 Link_out
PDB ID BGC Link_out
ChEBI ID 15903 Link_out
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
Name: Glucokinase
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: GCK
Uniprot ID: P35557 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-3
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: HK3
Uniprot ID: P52790 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-2
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: HK2
Uniprot ID: P52789 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Hexokinase-1
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: HK1
Uniprot ID: P19367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: GDH/6PGL endoplasmic bifunctional protein
Reactions:
Beta-D-Glucose + NAD(P)(+) unknown Gluconolactone + NAD(P)H details
Gene Name: H6PD
Uniprot ID: O95479 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Lactase-phlorizin hydrolase
Reactions: Not Available
Gene Name: LCT
Uniprot ID: P09848 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: ADP-dependent glucokinase
Reactions:
Beta-D-Glucose + ADP unknown Beta-D-Glucose 6-phosphate + Adenosine monophosphate details
Gene Name: ADPGK
Uniprot ID: Q9BRR6 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Trehalase
Reactions:
Trehalose + Water unknown Beta-D-Glucose + Alpha-D-Glucose details
Gene Name: TREH
Uniprot ID: O43280 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Beta-galactosidase
Reactions: Not Available
Gene Name: GLB1
Uniprot ID: P16278 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucosylceramidase
Reactions: Not Available
Gene Name: GBA
Uniprot ID: P04062 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Glucokinase regulatory protein
Reactions: Not Available
Gene Name: GCKR
Uniprot ID: Q14397 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytosolic beta-glucosidase
Reactions:
Cellobiose + Water unknown Beta-D-Glucose details
Cellulose + Water unknown Cellulose + Beta-D-Glucose details
Dhurrin + Water unknown (S)-4-Hydroxymandelonitrile + Beta-D-Glucose details
Lotaustralin + Water unknown (2R)-2-Hydroxy-2-methylbutanenitrile + Beta-D-Glucose details
Linamarin + Water unknown Acetone cyanohydrin + Beta-D-Glucose details
Gene Name: GBA3
Uniprot ID: Q9H227 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Maltase-glucoamylase, intestinal
Reactions: Not Available
Gene Name: MGAM
Uniprot ID: O43451 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Aldose 1-epimerase
Reactions:
Alpha-D-Glucose unknown Beta-D-Glucose details
Gene Name: GALM
Uniprot ID: Q96C23 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Putative hexokinase HKDC1
Reactions:
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphate details
Gene Name: HKDC1
Uniprot ID: Q2TB90 Link_out
Protein Sequence: FASTA