alpha-D-Glucose (PAMDB000492)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000492
Identification
Name: alpha-D-Glucose
Description:Alpha-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. Alpha-D-Glucose is an intermediate in glycolysis/gluconeogenesis pathway where it is converted to beta-D-glucose via galactose-1-epimerase (mutarotase) (EC:5.1.3.3). It is also involved in several other metabolic pathways: fructose and mannose metabolism, galactose metabolism, starch and sucrose metabolism and amino sugar and nucleotide sugar metabolism.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • α-glucose
  • 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol
  • A-D-Glucopyranose
  • A-D-Glucose
  • a-delta-Glucopyranose
  • a-delta-Glucose
  • A-Dextrose
  • A-Glucose
  • a-δ-Glucopyranose
  • a-δ-Glucose
  • Alpha-D-Glucopyranose
  • Alpha-D-Glucose
  • Alpha-delta-Glucopyranose
  • Alpha-delta-Glucose
  • Alpha-Dextrose
  • Alpha-Glucose
  • D-glucose
  • Glucose
  • Hexopyranose
  • α-D-Glucopyranose
  • α-D-Glucose
  • α-Dextrose
  • α-Glucose
  • α-δ-Glucopyranose
  • α-δ-Glucose
Chemical Formula: C6H12O6
Average Molecular Weight: 180.1559
Monoisotopic Molecular Weight: 180.063388116
InChI Key: WQZGKKKJIJFFOK-DVKNGEFBSA-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: 492-62-6
IUPAC Name:(2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol
Traditional IUPAC Name: α-glucose
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: 146 °C
Experimental Properties:
PropertyValueSource
Water Solubility:500 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
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
Polarizability16.09 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
D-Maltose + Water <>2 alpha-D-Glucose
Sucrose + Water <> beta-D-Fructose + alpha-D-Glucose
alpha-D-Glucose <> D-Fructose
Glucose 1-phosphate + Water <> alpha-D-Glucose + Phosphate
alpha-D-Glucose <> b-D-Glucose
alpha-Lactose + Water <> alpha-D-Glucose + D-Galactose
Adenosine triphosphate + alpha-D-Glucose <> ADP + Glucose 6-phosphate
D-Glucoside + Water <> ROH + alpha-D-Glucose
Neohancoside D + Water <> beta-D-Fructose + alpha-D-Glucose
Trehalose + Water > b-D-Glucose + alpha-D-Glucose
α,α-trehalose + Water > alpha-D-Glucose + Beta-D-Glucose + b-D-Glucose
alpha-D-Glucose + HPr - phosphorylated > α-D-glucose 6-phosphate + HPr + Mannose 6-phosphate
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9100000000-53278ff57ca00e1b5d1aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0079-9000000000-c4182c64988208ac78b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • Dalmau SR, Freitas CS: Sugar inhibition of the lectin jacalin: comparison of three assays. Braz J Med Biol Res. 1989;22(5):601-10. Pubmed: 2620170
  • Georgiou S, Pasmatzi E, Monastirli A, Sakkis T, Alachioti S, Tsambaos D: Age-related alterations in the carbohydrate residue composition of the cell surface in the unexposed normal human epidermis. Gerontology. 2005 May-Jun;51(3):155-60. Pubmed: 15832040
  • 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
  • Onyshchenko AM, Korobkova KS, Kovalenko NK, Kasumova SO, Skrypal' IH: [The role of the carbohydrate composition of the glycocalyx in some species of lactobacilli in the manifestation of their adhesive properties] Mikrobiol Z. 1999 Nov-Dec;61(6):22-8. Pubmed: 10733280
  • Skrypal' IH, Tokovenko IP, Malynovs'ka LP: [Carbohydrate receptors for Mycoplasma fermentans adhesion on human epithelial tissues] Mikrobiol Z. 1995 Jul-Aug;57(4):17-22. Pubmed: 8548067
  • Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference: Simmons, Blake A.; Volponi, Joanne V.; Ingersoll, David; Walker, Andrew. Conversion of sucrose to b-D-glucose using three-stage immobilized enzyme process. U.S. (2007), 12pp.
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID17925
HMDB IDHMDB03345
Pubchem Compound ID79025
Kegg IDC00267
ChemSpider ID71358
Wikipedia IDNot Available
BioCyc IDALPHA-GLUCOSE
EcoCyc IDALPHA-GLUCOSE
Ligand ExpoGLC

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
• 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