Record Information
Version2.0
Creation Date2012-05-31 13:59:22 -0600
Update Date2015-06-03 15:54:24 -0600
Secondary Accession Numbers
  • ECMDB03498
Identification
Name:beta-D-Glucose 6-phosphate
DescriptionBeta-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
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
Weight:Average: 260.1358
Monoisotopic: 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
Description belongs to the class of organic compounds known as hexose phosphates. These are carbohydrate derivatives containing a hexose substituted by one or more phosphate groups.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentHexose phosphates
Alternative Parents
Substituents
  • Hexose phosphate
  • Monosaccharide phosphate
  • Monoalkyl phosphate
  • Organic phosphoric acid derivative
  • Alkyl phosphate
  • Oxane
  • Phosphoric acid ester
  • Hemiacetal
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Hydrocarbon derivative
  • Alcohol
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic 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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity46.8 m³·mol⁻¹ChemAxon
Polarizability20.96 ųChemAxon
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
beta-D-Glucose 1-phosphate > 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-Fructose 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
beta-D-Glucose 6-phosphate + NADP <>6 6-Phosphonoglucono-D-lactone + NADPH + Hydrogen ion
Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate
Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate
Adenosine triphosphate + b-D-Glucose <> ADP + beta-D-Glucose 6-phosphate
Glucose 6-phosphate + Alpha-D-glucose 6-phosphate <> beta-D-Glucose 6-phosphate
SMPDB Pathways:
Amino sugar and nucleotide sugar metabolism IIIPW000895 ThumbThumb?image type=greyscaleThumb?image type=simple
Galactose metabolismPW000821 ThumbThumb?image type=greyscaleThumb?image type=simple
Pentose PhosphatePW000893 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary metabolites: Trehalose Biosynthesis and MetabolismPW000968 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW000941 ThumbThumb?image type=greyscaleThumb?image type=simple
colanic acid building blocks biosynthesisPW000951 ThumbThumb?image type=greyscaleThumb?image type=simple
galactose degradation/Leloir PathwayPW000884 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolismPW000914 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IIPW000915 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism III (sn-glycero-3-phosphoethanolamine)PW000916 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism IV (glycerophosphoglycerol)PW000917 ThumbThumb?image type=greyscaleThumb?image type=simple
glycerol metabolism V (glycerophosphoserine)PW000918 ThumbThumb?image type=greyscaleThumb?image type=simple
glycolysis and pyruvate dehydrogenasePW000785 ThumbThumb?image type=greyscaleThumb?image type=simple
inner membrane transportPW000786 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
EcoCyc Pathways:
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9740000000-a6e81224fb97751dc2e6View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-5572890000-1bd34b89c6cb6aadc13cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-9060000000-b446300429049a22bea4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d5aaca13a836cb9f1725View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dm-0970000000-40dbaf3d3c72cf65bf47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-7900000000-00bc03290b6c0bfb7f84View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9000000000-7a6ff6606f1dbc2f0ae4View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
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

General function:
Involved in glucose-6-phosphate isomerase activity
Specific function:
D-glucose 6-phosphate = D-fructose 6- phosphate
Gene Name:
pgi
Uniprot ID:
P0A6T1
Molecular weight:
61529
Reactions
D-glucose 6-phosphate = D-fructose 6-phosphate.
General function:
Involved in glucokinase activity
Specific function:
Not highly important in E.coli as glucose is transported into the cell by the PTS system already as glucose 6-phosphate
Gene Name:
glk
Uniprot ID:
P0A6V8
Molecular weight:
34723
Reactions
ATP + D-glucose = ADP + D-glucose 6-phosphate.
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
Uniprot ID:
P0AC53
Molecular weight:
55704
Reactions
D-glucose 6-phosphate + NADP(+) = 6-phospho-D-glucono-1,5-lactone + NADPH.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Can hydrolyze salicin and arbutin
Gene Name:
bglB
Uniprot ID:
P11988
Molecular weight:
53161
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolyzes a wide variety of P-beta-glucosides including cellobiose-6P, salicin-6P, arbutin-6P, gentiobiose-6P, methyl- beta-glucoside-6P and p-nitrophenyl-beta-D-glucopyranoside-6P. Is also able to hydrolyze phospho-N,N'-diacetylchitobiose
Gene Name:
chbF
Uniprot ID:
P17411
Molecular weight:
50512
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Can hydrolyze salicin, cellobiose, and probably arbutin
Gene Name:
ascB
Uniprot ID:
P24240
Molecular weight:
53935
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
Involved in sugar:hydrogen symporter activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport
Gene Name:
crr
Uniprot ID:
P69783
Molecular weight:
18251
Reactions
Protein EIIA N(pi)-phospho-L-histidine + protein EIIB = protein EIIA + protein EIIB N(pi)-phospho-L-histidine/cysteine.
General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
Gene Name:
ptsG
Uniprot ID:
P69786
Molecular weight:
50676
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.
General function:
Involved in beta-phosphoglucomutase activity
Specific function:
Reversible transformation of glucose 6-phosphate and beta-glucose 1-phosphate
Gene Name:
ycjU
Uniprot ID:
P77366
Molecular weight:
23565
Reactions
Beta-D-glucose 1-phosphate = beta-D-glucose 6-phosphate.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate
Gene Name:
bglA
Uniprot ID:
Q46829
Molecular weight:
55361
Reactions
6-phospho-beta-D-glucosyl-(1,4)-D-glucose + H(2)O = D-glucose + D-glucose 6-phosphate.
General function:
Not Available
Specific function:
Not Available
Gene Name:
yeaD
Uniprot ID:
P39173
Molecular weight:
Not Available

Transporters

General function:
Involved in protein-N(PI)-phosphohistidine-sugar phosphotransferase activity
Specific function:
The phosphoenolpyruvate-dependent sugar phosphotransferase system (sugar PTS), a major carbohydrate active -transport system, catalyzes the phosphorylation of incoming sugar substrates concomitantly with their translocation across the cell membrane. This system is involved in glucose transport. This enzyme is also a chemoreceptor monitoring the environment for changes in sugar concentration
Gene Name:
ptsG
Uniprot ID:
P69786
Molecular weight:
50676
Reactions
Protein EIIB N(pi)-phospho-L-histidine/cysteine + sugar = protein EIIB + sugar phosphate.