b-D-Glucose (PAMDB000145)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 12:54:54 PM
Metabolite IDPAMDB000145
Identification
Name: b-D-Glucose
Description:B-D-glucose is a member of the chemical class known as Hexoses. These are monosaccharides in which the sugar unit is a hexose. Glucose (C6H12O6, also known as D-glucose, dextrose, or grape sugar) is a simple sugar (monosaccharide) and an important carbohydrate in biology. Cells use it as the primary source of energy and a metabolic intermediate. Glucose is one of the main products of photosynthesis and fuels for cellular respiration. Glucose exists in several different molecular structures, but all of these structures can be divided into two families of mirror-images (stereoisomers). Only one set of these isomers exists in nature, those derived from the right-handed form of glucose, denoted D-glucose. D-glucose is sometimes referred to as dextrose, although the use of this name is strongly discouraged. The term dextrose is derived from dextrorotatory glucose. This name is therefore confusing when applied to the enantiomer, which rotates light the opposite direction. Starch and cellulose are polymers derived from the dehydration of D-glucose. The other stereoisomer, called L-glucose, is hardly ever found in nature. (WikiPedia)
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • β-D-glucopyranose
  • β-glucose
  • 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol
  • B-D-Glucopyranose
  • b-delta-Glucopyranose
  • B-Dextrose
  • B-Glucose
  • b-δ-Glucopyranose
  • Beta-D-Glucopyranose
  • Beta-D-Glucose
  • Beta-delta-Glucopyranose
  • Beta-Dextrose
  • Beta-Glucose
  • D-glucose
  • D-Glucose-ring
  • Dextrose
  • Glc
  • Glc-ring
  • Glucose
  • Glucoside
  • β-D-Glucopyranose
  • β-D-Glucose
  • β-Dextrose
  • β-Glucose
  • β-δ-Glucopyranose
Chemical Formula: C6H12O6
Average Molecular Weight: 180.1559
Monoisotopic Molecular Weight: 180.063388116
InChI Key: WQZGKKKJIJFFOK-VFUOTHLCSA-N
InChI: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
CAS number: 492-61-5
IUPAC Name:(2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Name: glucoside
SMILES:OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monosaccharides. These 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.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct Parent Monosaccharides
Alternative Parents
Substituents
  • Oxane
  • Monosaccharide
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:-2.912PhysProp
Predicted Properties
PropertyValueSource
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
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Cellobiose + Water <>2 b-D-Glucose
Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate
alpha-D-Glucose <> b-D-Glucose
Cellulose + Water <> Cellulose + b-D-Glucose
3-Ketolactose + Water <> 3-Keto-beta-D-galactose + b-D-Glucose
b-D-Glucose <> D-glucose
Phosphoenolpyruvic acid + b-D-Glucose > Glucose 6-phosphate + Pyruvic acid
a &beta;-D glucoside + Water a non glucosylated glucose acceptor + b-D-Glucose
Cellobiose-6-phosphate + Water > Glucose 6-phosphate + b-D-Glucose
D-Glucose <> b-D-Glucose
Water + Melibiose > D-Galactose + b-D-Glucose
Maltotriose + D-Maltose <> Maltotetraose + b-D-Glucose
Water + alpha-Lactose > D-Galactose + b-D-Glucose
GDP-&alpha;-D-glucose + Water > Hydrogen ion + b-D-Glucose + Guanosine diphosphate
b-D-Glucose + a ubiquinone > Gluconolactone + a ubiquinol
b-D-Glucose + Adenosine triphosphate > Hydrogen ion + Glucose 6-phosphate + ADP
isoprimeverose + Water b-D-Glucose + D-Xylose
Gluconolactone + Hydrogen ion <> b-D-Glucose
Trehalose 6-phosphate + Water > Glucose 6-phosphate + b-D-Glucose
Trehalose + Water > b-D-Glucose + D-Glucose
Trehalose + Water > b-D-Glucose + alpha-D-Glucose
alpha-Lactose + Water > beta-D-Galactose + Beta-D-Glucose + b-D-Glucose
Beta-D-Glucose + Adenosine triphosphate + b-D-Glucose > Hydrogen ion + Adenosine diphosphate + beta-D-Glucose 6-phosphate + ADP
Melibiose + Water > Alpha-D-Galactose + Beta-D-Glucose + b-D-Glucose
α,α-trehalose + Water > alpha-D-Glucose + Beta-D-Glucose + b-D-Glucose
Beta-D-Glucose + HPr - phosphorylated + b-D-Glucose > beta-D-Glucose 6-phosphate + HPr
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01q9-0900000000-ecd0aedc67c9a2eec60fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03ea-2900000000-e4daf22c7320ccc41812View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0005-9200000000-91fc3940732f782a88bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-e9f3e728d1b340759a09View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-5900000000-c0a478f2b9c5bbc6c4baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-06852e2088bf1c6b38c4View in MoNA
MSMass Spectrum (Electron Ionization)splash10-03kc-9000000000-a60df7b043f8947d6909View in MoNA
References
References:
  • Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
  • Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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
External Links:
ResourceLink
CHEBI ID15903
HMDB IDHMDB00516
Pubchem Compound ID64689
Kegg IDC00221
ChemSpider ID58238
Wikipedia IDNot Available
BioCyc IDGLC
EcoCyc IDGLC
Ligand ExpoBGC

Enzymes

Protein Details
• Glucokinase
General function:
Involved in glucokinase activity
Specific function:
Not highly important in Pseudomonas aeruginosa as glucose is transported into the cell by the PTS system already as glucose 6-phosphate
Gene Name:
glk
Locus Tag:
PA3193
Molecular weight:
34.6 kDa
Reactions
ATP + D-glucose = ADP + D-glucose 6-phosphate.
Protein Details
• Periplasmic trehalase
General function:
Involved in catalytic activity
Specific function:
Provides the cells with the ability to utilize trehalose at high osmolarity by splitting it into glucose molecules that can subsequently be taken up by the phosphotransferase-mediated uptake system
Gene Name:
treA
Locus Tag:
PA2416
Molecular weight:
61.2 kDa
Reactions
Alpha,alpha-trehalose + H(2)O = 2 D-glucose.
Protein Details
• Quinoprotein glucose dehydrogenase
General function:
Involved in oxidoreductase activity, acting on CH-OH group of donors
Specific function:
GDH is probably involved in energy conservation rather than in sugar metabolism
Gene Name:
gcd
Locus Tag:
PA2290
Molecular weight:
86.2 kDa
Reactions
D-glucose + ubiquinone = D-glucono-1,5-lactone + ubiquinol.
Protein Details
• Periplasmic beta-glucosidase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal, non-reducing beta-D- glucosyl residues with release of beta-D-glucose
Gene Name:
bglX
Locus Tag:
PA1726
Molecular weight:
83 kDa
Reactions
Hydrolysis of terminal, non-reducing beta-D-glucosyl residues with release of beta-D-glucose.

Transporters