Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2013-04-19 22:40:22 UTC
HMDB IDHMDB00516
Secondary Accession Numbers
  • HMDB03340
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. 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
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 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 IUPAC 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
KingdomOrganic Compounds
Super ClassCarbohydrates and Carbohydrate Conjugates
ClassMonosaccharides
Sub ClassHexoses
Other Descriptors
  • Aliphatic Heteromonocyclic Compounds
  • Carbohydrates and Carbohydrate Conjugates
  • D-galactopyranose(ChEBI)
Substituents
  • 1,2 Diol
  • Hemiacetal
  • Oxane
  • Primary Alcohol
  • Secondary Alcohol
Direct ParentHexoses
Ontology
StatusExpected and Not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
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 area110.38ChemAxon
rotatable bond count1ChemAxon
refractivity35.92ChemAxon
polarizability16.43ChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
GluconeogenesisSMP00128map00010
GlycolysisSMP00040map00010
Trehalose DegradationSMP00467Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB011824
KNApSAcK IDNot Available
Chemspider ID58238
KEGG Compound IDC00221
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB00516
Metagene LinkHMDB00516
METLIN ID3755
PubChem Compound64689
PDB IDBGC
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 ReferencesNot Available

Enzymes

Gene Name:
GCK
Uniprot ID:
P35557
Reactions
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphatedetails
Gene Name:
HK3
Uniprot ID:
P52790
Reactions
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphatedetails
Gene Name:
HK2
Uniprot ID:
P52789
Reactions
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphatedetails
Gene Name:
HK1
Uniprot ID:
P19367
Reactions
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphatedetails
Gene Name:
H6PD
Uniprot ID:
O95479
Reactions
Beta-D-Glucose + NAD(P)(+) unknown Gluconolactone + NAD(P)Hdetails
Gene Name:
LCT
Uniprot ID:
P09848
Gene Name:
ADPGK
Uniprot ID:
Q9BRR6
Reactions
Beta-D-Glucose + ADP unknown Beta-D-Glucose 6-phosphate + Adenosine monophosphatedetails
Gene Name:
TREH
Uniprot ID:
O43280
Reactions
Trehalose + Water unknown Beta-D-Glucose + Alpha-D-Glucosedetails
Gene Name:
GLB1
Uniprot ID:
P16278
Gene Name:
GBA
Uniprot ID:
P04062
Gene Name:
GCKR
Uniprot ID:
Q14397
Gene Name:
GBA3
Uniprot ID:
Q9H227
Reactions
Cellobiose + Water unknown Beta-D-Glucosedetails
Cellulose + Water unknown Cellulose + Beta-D-Glucosedetails
Dhurrin + Water unknown (S)-4-Hydroxymandelonitrile + Beta-D-Glucosedetails
Lotaustralin + Water unknown (2R)-2-Hydroxy-2-methylbutanenitrile + Beta-D-Glucosedetails
Linamarin + Water unknown Acetone cyanohydrin + Beta-D-Glucosedetails
Gene Name:
MGAM
Uniprot ID:
O43451
Gene Name:
GALM
Uniprot ID:
Q96C23
Reactions
Alpha-D-Glucose unknown Beta-D-Glucosedetails
Gene Name:
HKDC1
Uniprot ID:
Q2TB90
Reactions
Adenosine triphosphate + Beta-D-Glucose unknown ADP + Beta-D-Glucose 6-phosphatedetails