You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Yeast Metabolome Database.
Identification
YMDB IDYMDB00947
NameGlucose 6-phosphate
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
DescriptionGlucose 6-phosphate, also known as robison ester or GLC6P, 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. Glucose 6-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Glucose 6-phosphate exists in all living species, ranging from bacteria to humans.
Structure
Thumb
Synonyms
  • a-D-glucose 6- phosphate
  • alpha-D-glucose 6- phosphate
  • alpha-D-glucose 6-phosphate
  • alpha-D-Hexose 6-phosphate
  • D-Glucose 6-phosphate
  • D-Glucose-6-dihydrogen phosphate
  • D-Hexose 6-phosphate
  • D(+)-Glucopyranose 6-phosphate
  • Glucose 6-phosphate
  • Glucose 6-phosphic acid
  • Glucose-6-phosphate
  • Robison ester
  • 6-O-Phosphono-D-glucopyranose
  • GLC6p
  • D-Glucose 6-phosphoric acid
  • Glucose 6-phosphoric acid
  • D-Glucopyranose 6-phosphoric acid
CAS number56-73-5
WeightAverage: 260.1358
Monoisotopic: 260.029718526
InChI KeyNBSCHQHZLSJFNQ-GASJEMHNSA-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)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid
Traditional IUPAC Nameglucose 6-phosphate
Chemical FormulaC6H13O9P
SMILES[H]OC1([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
StateLiquid
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Polarizability21 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular LocationsNot Available
Organoleptic PropertiesNot Available
SMPDB Pathways
Leloir PathwayPW002397 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
Galactose metabolismec00052 Map00052
Glycolysis / Gluconeogenesisec00010 Map00010
Inositol phosphate metabolismec00562 Map00562
Pentose phosphate pathwayec00030 Map00030
SMPDB Reactions
Glucose 6-phosphate1D-myo-inositol 3-phosphate
Glucose 6-phosphate1D-myo-inositol 3-phosphate
KEGG ReactionsNot Available
Concentrations
Intracellular Concentrations
Intracellular ConcentrationSubstrateGrowth ConditionsStrainCitation
2050 ± 110 µM 20 ml 2% (wt/vol) glucose, 0.5% (wt/vol) ammonium sulfate, 0.17% (wt/vol) yeast nitrogen base without amino acids (Difco, Detroit, MI) and 100 mM potassium phthalate at pH 5.0, supplemented with required nutrients (40 mg/L uracil, 40 mg/L Ltryptophan, 60 aerobicBaker's yeastPMID: 11135551
2300 ± 200 µM Synthetic medium with 2% glucoseaerobic;growing cellsBaker's yeastPMID: 6229402
560 ± 80 µM Synthetic medium with 2% glucoseaerobic;resting cellsBaker's yeastPMID: 6229402
340 ± 130 µM Synthetic medium with 2% glucoseanaerobic;resting cellsBaker's yeastPMID: 6229402
1360 ± 600 µM Synthetic medium with 2% galactoseaerobic;resting cellsBaker's yeastPMID: 6229402
Conversion Details Here
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-000b-1932000000-59f4881b86595037d013JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS)splash10-0f7t-1933000000-4894135f21c21c369428JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS; 1 MEOX)splash10-00di-9522000000-81266970683faa1f2aafJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS; 1 MEOX)splash10-00di-9412000000-2f2a0e772025b48bf6f3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)splash10-000j-1956000000-692b4df2b9c16f6a780cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 6 TMS)splash10-000i-1957000000-bd94955ffc1474153a48JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (6 TMS)splash10-0v0a-0596000000-676527ddfc1d596e78f8JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000b-1932000000-59f4881b86595037d013JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f7t-1933000000-4894135f21c21c369428JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9522000000-81266970683faa1f2aafJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-00di-9412000000-2f2a0e772025b48bf6f3JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000j-1956000000-692b4df2b9c16f6a780cJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-1957000000-bd94955ffc1474153a48JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0v0a-0596000000-676527ddfc1d596e78f8JSpectraViewer | MoNA
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-6252790000-ef5662fb1886367e07f2JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-03di-0090000000-5653def80d1b5ff0eebbJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-000b-9200000000-66741d773ac31b347625JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-000t-9000000000-068809fcfaff0d387e6bJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negativesplash10-0a4i-1090000000-d6e539d78b38c01dafeaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negativesplash10-0002-9210000000-8b9ff1c5095f48a81fefJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negativesplash10-0002-9000000000-f6e1147852f75db4c0a4JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negativesplash10-002b-9000000000-1c52fd659f8a2b795e51JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negativesplash10-004i-9000000000-d3f6a05e18ea6d56c56dJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0006-0890000000-5f3047c92c970dfe6927JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-004i-0900000000-b84eb7685667fa7ee85eJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-004i-2900000000-d4a0d51bb6e2da28533aJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-004i-6900000000-dfb5bcbd9a7439c32352JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-03gi-9600000000-a0922c82e185f6b5aa67JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0290000000-7ac7b397c52f29cd3822JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-052b-6590000000-5cdbc23378480ac55c4fJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004i-1900000000-b74270f21c6086362227JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-002b-9000000000-bc69e8fa215a3b82dcf2JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0a4i-0090000000-d6e539d78b38c01dafeaJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , negativesplash10-0002-9210000000-10019f92fd1eca143babJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0490000000-94ea79ec673f4688b7a0JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03dm-5940000000-c649262446626dcb8d6eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0uka-9800000000-aae2cb792906d2dec6cdJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a6r-8290000000-8e20219f94b3fe964e38JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9000000000-b19b64f5cb4124047bafJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-ecb75a44e3d25affdf31JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableJSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Raamsdonk, L. M., Teusink, B., Broadhurst, D., Zhang, N., Hayes, A., Walsh, M. C., Berden, J. A., Brindle, K. M., Kell, D. B., Rowland, J. J., Westerhoff, H. V., van Dam, K., Oliver, S. G. (2001). "A functional genomics strategy that uses metabolome data to reveal the phenotype of silent mutations." Nat Biotechnol 19:45-50.11135551
  • Coevoet, M. A., Hervagault, J. F. (1997). "Irreversible metabolic transitions: the glucose 6-phosphate metabolism in yeast cell-free extracts." Biochem Biophys Res Commun 234:162-166.9168982
  • Eschrich, K., Schellenberger, W., Hofmann, E. (1990). "A hysteretic cycle in glucose 6-phosphate metabolism observed in a cell-free yeast extract." Eur J Biochem 188:697-703.2158887
  • Thevelein, J. M., Hohmann, S. (1995). "Trehalose synthase: guard to the gate of glycolysis in yeast?" Trends Biochem Sci 20:3-10.7878741
  • Vaseghi, S., Baumeister, A., Rizzi, M., Reuss, M. (1999). "In vivo dynamics of the pentose phosphate pathway in Saccharomyces cerevisiae." Metab Eng 1:128-140.10935926
  • Senac, T., Hahn-Hagerdal, B. (1990). "Intermediary Metabolite Concentrations in Xylulose- and Glucose-Fermenting Saccharomyces cerevisiae Cells." Appl Environ Microbiol 56:120-126.16348083
  • Lagunas, R., Gancedo, C. (1983). "Role of phosphate in the regulation of the Pasteur effect in Saccharomyces cerevisiae." Eur J Biochem 137:479-483.6229402
  • Castrillo, J. I., Zeef, L. A., Hoyle, D. C., Zhang, N., Hayes, A., Gardner, D. C., Cornell, M. J., Petty, J., Hakes, L., Wardleworth, L., Rash, B., Brown, M., Dunn, W. B., Broadhurst, D., O'Donoghue, K., Hester, S. S., Dunkley, T. P., Hart, S. R., Swainston, N., Li, P., Gaskell, S. J., Paton, N. W., Lilley, K. S., Kell, D. B., Oliver, S. G. (2007). "Growth control of the eukaryote cell: a systems biology study in yeast." J Biol 6:4.17439666
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID4170
HMDB IDHMDB01401
Pubchem Compound ID208
Kegg IDC00668
ChemSpider ID25057696
FOODB IDFDB021818
WikipediaGlucose_6-phosphate
BioCyc IDGLC-6-P

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 ATP binding
Specific function:
Main glucose phosphorylating enzyme. May play a regulatory role in both induction and repression of gene expression by glucose
Gene Name:
HXK2
Uniprot ID:
P04807
Molecular weight:
53942.0
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-phosphate
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
Not Available
Uniprot ID:
Q06204
Molecular weight:
48968.80078
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
General function:
Involved in ATP binding
Specific function:
ATP + D-hexose = ADP + D-hexose 6-phosphate
Gene Name:
HXK1
Uniprot ID:
P04806
Molecular weight:
53737.89844
Reactions
ATP + D-hexose → ADP + D-hexose 6-phosphate.
ATP + D-fructose → ADP + D-fructose 1-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 catalytic activity
Specific function:
Synthase catalytic subunit of the trehalose synthase complex that catalyzes the production of trehalose from glucose-6- phosphate and UDP-glucose in a two step process. Can function independently of the complex
Gene Name:
TPS1
Uniprot ID:
Q00764
Molecular weight:
56147.5
Reactions
UDP-glucose + D-glucose 6-phosphate → UDP + alpha,alpha-trehalose 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 intramolecular transferase activity, phosphotransferases
Specific function:
This enzyme participates in both the breakdown and synthesis of glucose
Gene Name:
Not Available
Uniprot ID:
Q03262
Molecular weight:
71068.60156
Reactions
Alpha-D-glucose 1-phosphate → alpha-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
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:
ZWF1
Uniprot ID:
P11412
Molecular weight:
57521.10156
Reactions
D-glucose 6-phosphate + NADP(+) → 6-phospho-D-glucono-1,5-lactone + NADPH.
General function:
Involved in inositol-3-phosphate synthase activity
Specific function:
D-glucose 6-phosphate = 1D-myo-inositol 3- phosphate
Gene Name:
INO1
Uniprot ID:
P11986
Molecular weight:
59641.60156
Reactions
D-glucose 6-phosphate → 1D-myo-inositol 3-phosphate.