beta-D-Glucose 6-phosphate (PAMDB000506)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000506
Identification
Name: beta-D-Glucose 6-phosphate
Description:Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate, the alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. b-G6P is involved in the glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways [Kegg ID: C01172]. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted to glycogen.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • β-D-glucose-6-P
  • b-D-Glucose 6-(dihydrogen phosphate)
  • b-D-Glucose 6-(dihydrogen phosphoric acid)
  • b-D-Glucose 6-phosphate
  • b-D-Glucose 6-phosphoric acid
  • b-D-Glucose-6-P
  • Beta-D-Glucose 6-(dihydrogen phosphate)
  • beta-D-Glucose 6-(dihydrogen phosphoric acid)
  • Beta-D-Glucose 6-phosphate
  • beta-D-Glucose 6-phosphoric acid
  • Beta-D-Glucose-6-P
  • D-Glucose-6-P
  • D-Glucose-6-phosphate
  • D-Glucose-6-phosphoric acid
  • Glucose-6-P
  • Glucose-6-phosphate
  • Glucose-6-phosphoric acid
  • β-D-Glucose 6-(dihydrogen phosphate)
  • β-D-Glucose 6-(dihydrogen phosphoric acid)
  • β-D-Glucose 6-phosphate
  • β-D-Glucose 6-phosphoric acid
  • β-D-Glucose-6-P
Chemical Formula: C6H13O9P
Average Molecular Weight: 260.1358
Monoisotopic Molecular Weight: 260.029718526
InChI Key: NBSCHQHZLSJFNQ-VFUOTHLCSA-N
InChI:InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1
CAS number: Not Available
IUPAC Name:{[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Name: β-D-glucose 6-phosphate
SMILES:O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as monosaccharide phosphates. These are monosaccharides comprising a phosphated group linked to the carbohydrate unit.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassMonosaccharides
Direct Parent Monosaccharide phosphates
Alternative Parents
Substituents
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Alkyl phosphate
  • Phosphoric acid ester
  • Oxane
  • Organic phosphoric acid derivative
  • Organic phosphate
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
Experimental Properties:
PropertyValueSource
LogP:-3.643PhysProp
Predicted Properties
PropertyValueSource
Water Solubility31.4 mg/mLALOGPS
logP-2.1ALOGPS
logP-3.1ChemAxon
logS-0.92ALOGPS
pKa (Strongest Acidic)1.22ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count6ChemAxon
Polar Surface Area156.91 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m3·mol-1ChemAxon
Polarizability20.96 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate
beta-D-Glucose 1-phosphate <> beta-D-Glucose 6-phosphate
beta-D-Glucose 6-phosphate + NADP <> 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion
Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate
beta-D-Glucose 6-phosphate <> beta-D-Fructose 6-phosphate
Arbutin 6-phosphate + Water <> Hydroquinone + beta-D-Glucose 6-phosphate
Salicin 6-phosphate + Water <> Salicyl alcohol + beta-D-Glucose 6-phosphate
Alpha-D-glucose 6-phosphate > beta-D-Glucose 6-phosphate
beta-D-Glucose 6-phosphate + NADP > 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion + NADPH
beta-D-Glucose 6-phosphate > Fructose 6-phosphate + Fructose 6-phosphate
D-tagatofuranose 6-phosphate > beta-D-Glucose 6-phosphate
beta-D-Glucose 6-phosphate <>
Beta-D-Glucose + Adenosine triphosphate + b-D-Glucose > Hydrogen ion + Adenosine diphosphate + beta-D-Glucose 6-phosphate + ADP
D-Glucose + Adenosine triphosphate > Hydrogen ion + Adenosine diphosphate + beta-D-Glucose 6-phosphate + ADP
beta-D-Glucose 6-phosphate > β-D-glucose 1-phosphate
Beta-D-Glucose + HPr - phosphorylated + b-D-Glucose > beta-D-Glucose 6-phosphate + HPr
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-1a5b3049c27a2a9b8996View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-4940000000-cbc695bef22278b36879View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uka-8900000000-320e52be29673422365eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-6290000000-e76ad7d6142e19f5a9c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e27be76de6d71ada7083View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9540d84c7e74555e7a01View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
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
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID17719
HMDB IDHMDB03498
Pubchem Compound ID439427
Kegg IDC01172
ChemSpider ID388538
Wikipedia IDNot Available
BioCyc IDGLC-6-P
EcoCyc IDGLC-6-P
Ligand ExpoBG6

Enzymes

Protein Details
• Glucose-6-phosphate isomerase
General function:
Involved in glucose-6-phosphate isomerase activity
Specific function:
D-glucose 6-phosphate = D-fructose 6- phosphate
Gene Name:
pgi
Locus Tag:
PA4732
Molecular weight:
61.9 kDa
Reactions
D-glucose 6-phosphate = D-fructose 6-phosphate.
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
• Glucose-6-phosphate 1-dehydrogenase
General function:
Involved in glucose-6-phosphate dehydrogenase activity
Specific function:
D-glucose 6-phosphate + NADP(+) = D-glucono- 1,5-lactone 6-phosphate + NADPH
Gene Name:
zwf
Locus Tag:
PA3183
Molecular weight:
55.6 kDa
Reactions
D-glucose 6-phosphate + NADP(+) = 6-phospho-D-glucono-1,5-lactone + NADPH.