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Identification
YMDB IDYMDB00311
NameBeta-D-Glucose 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Descriptionbeta-D-Glucose 6-phosphate, also known as b-D-glucose 6-phosphoric acid or 6-O-phosphono-b-D-glucopyranose, 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. beta-D-Glucose 6-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). beta-D-Glucose 6-phosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • beta-D-glucose 6-(dihydrogen phosphate)
  • beta-D-Glucose 6-phosphate
  • beta-D-Glucose 6-phosphic acid
  • 6-H2PO3glcbeta
  • 6-O-Phosphono-beta-D-glucopyranose
  • BETA-D-GLUCOSE-6-phosphATE
  • 6-O-Phosphono-b-D-glucopyranose
  • 6-O-Phosphono-β-D-glucopyranose
  • b-D-Glucose 6-(dihydrogen phosphate)
  • b-D-Glucose 6-(dihydrogen phosphoric acid)
  • beta-D-Glucose 6-(dihydrogen phosphoric acid)
  • Β-D-glucose 6-(dihydrogen phosphate)
  • Β-D-glucose 6-(dihydrogen phosphoric acid)
  • b-D-Glucose 6-phosphate
  • b-D-Glucose 6-phosphoric acid
  • beta-D-Glucose 6-phosphoric acid
  • Β-D-glucose 6-phosphate
  • Β-D-glucose 6-phosphoric acid
  • b-D-GLUCOSE-6-phosphate
  • b-D-GLUCOSE-6-phosphoric acid
  • beta-D-GLUCOSE-6-phosphoric acid
  • Β-D-glucose-6-phosphate
  • Β-D-glucose-6-phosphoric acid
CAS numberNot Available
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyNBSCHQHZLSJFNQ-VFUOTHLCSA-N
InChIInChI=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
IUPAC Name{[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Nameβ-D-glucose 6-phosphate
Chemical FormulaC6H13O9P
SMILES[H]O[C@]1([H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])O[H]
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
StateSolid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
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
Organoleptic PropertiesNot Available
SMPDB Pathways
Amino sugar and nucleotide sugar metabolismPW002413 ThumbThumb?image type=greyscaleThumb?image type=simple
Ethanol fermentationPW002448 ThumbThumb?image type=greyscaleThumb?image type=simple
Fructose MetabolismPW002390 ThumbThumb?image type=greyscaleThumb?image type=simple
Glycolysis IPW002386 ThumbThumb?image type=greyscaleThumb?image type=simple
Starch and sucrose metabolismPW002481 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways
Amino sugar and nucleotide sugar metabolismec00520 Map00520
Glycolysis / Gluconeogenesisec00010 Map00010
Pentose phosphate pathwayec00030 Map00030
Starch and sucrose metabolismec00500 Map00500
SMPDB Reactions
Adenosine triphosphate + Beta-D-GlucoseADP + Beta-D-Glucose 6-phosphate
Beta-D-Glucose 6-phosphateFructose 6-phosphate
Fructose 6-phosphateBeta-D-Glucose 6-phosphate
sucrose-6-phosphate + waterD-Fructose + Beta-D-Glucose 6-phosphate
Beta-D-Glucose 6-phosphateGlucose 1-phosphate
KEGG Reactions
Adenosine triphosphate + D-GlucoseBeta-D-Glucose 6-phosphate + hydron + ADP
aldehydo-D-glucose 6-phosphateBeta-D-Glucose 6-phosphate
Beta-D-Glucose 6-phosphateFructose 6-phosphate
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0005-9740000000-a6e81224fb97751dc2e6JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-001i-5572890000-1bd34b89c6cb6aadc13cJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-1a5b3049c27a2a9b8996JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-4940000000-cbc695bef22278b36879JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uka-8900000000-320e52be29673422365eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-6290000000-e76ad7d6142e19f5a9c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-e27be76de6d71ada7083JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9540d84c7e74555e7a01JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6s-9060000000-b446300429049a22bea4JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-d5aaca13a836cb9f1725JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-a5e502a2627af2048a1fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03dm-0970000000-40dbaf3d3c72cf65bf47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01ot-7900000000-00bc03290b6c0bfb7f84JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9000000000-7a6ff6606f1dbc2f0ae4JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Maitra, P. K., Lobo, Z. (1983). "Genetics of yeast glucokinase." Genetics 105:501-515.6357942
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17719
HMDB IDHMDB03498
Pubchem Compound ID439427
Kegg IDC01172
ChemSpider ID25057696
FOODB IDFDB031291
WikipediaGlucose_6-phosphate
BioCyc IDNot Available

Enzymes

General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose. Can also act on mannose
Gene Name:
PGM2
Uniprot ID:
P37012
Molecular weight:
63088.0
Reactions
Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-phosphate.
General function:
Involved in intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose. Can also act on mannose
Gene Name:
PGM1
Uniprot ID:
P33401
Molecular weight:
63111.30078
Reactions
Alpha-D-glucose 1-phosphate → alpha-D-glucose 6-phosphate.
General function:
Involved in glucose-6-phosphate isomerase activity
Specific function:
D-glucose 6-phosphate = D-fructose 6- phosphate
Gene Name:
PGI1
Uniprot ID:
P12709
Molecular weight:
61298.89844
Reactions
D-glucose 6-phosphate → D-fructose 6-phosphate.
General function:
Involved in ATP binding
Specific function:
Putative glucokinase involved in phosphorylation of aldohexoses and glucose uptake. Involved in sporulation. Required for the full activation of the early meiotic inducer IME1
Gene Name:
EMI2
Uniprot ID:
Q04409
Molecular weight:
55920.30078
Reactions
ATP + D-glucose → ADP + D-glucose 6-phosphate.
General function:
Involved in ATP binding
Specific function:
Two isoenzymes, hexokinase-1 and hexokinase-2, can phosphorylate keto- and aldohexoses in yeast, whereas a third isoenzyme, GLK, is specific for aldohexoses. All glucose phosphorylating enzymes are involved in glucose uptake
Gene Name:
GLK1
Uniprot ID:
P17709
Molecular weight:
55376.89844
Reactions
ATP + D-glucose → ADP + D-glucose 6-phosphate.
General function:
Involved in isomerase activity
Specific function:
Catalyzes the interconversion between the alpha and beta anomers from at least three hexose 6-phosphate sugars (Glc6P, Gal6P, and Man6P)
Gene Name:
Not Available
Uniprot ID:
Q03161
Molecular weight:
33955.69922
Reactions
Alpha-D-glucose 6-phosphate → beta-D-glucose 6-phosphate.
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal non-reducing beta-D- fructofuranoside residues in beta-D-fructofuranosides
Gene Name:
SUC2
Uniprot ID:
P00724
Molecular weight:
60638.89844
Reactions