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Identification |
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YMDB ID | YMDB00947 |
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Name | Glucose 6-phosphate |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Glucose 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. |
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Structure | |
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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
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CAS number | 56-73-5 |
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Weight | Average: 260.1358 Monoisotopic: 260.029718526 |
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InChI Key | NBSCHQHZLSJFNQ-GASJEMHNSA-N |
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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 |
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IUPAC Name | {[(2R,3S,4S,5R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid |
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Traditional IUPAC Name | glucose 6-phosphate |
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Chemical Formula | C6H13O9P |
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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] |
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Chemical Taxonomy |
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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. |
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Kingdom | Organic compounds |
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Super Class | Organic oxygen compounds |
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Class | Organooxygen compounds |
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Sub Class | Carbohydrates and carbohydrate conjugates |
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Direct Parent | Hexose phosphates |
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Alternative Parents | |
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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
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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Physical Properties |
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State | Liquid |
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Charge | 0 |
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Melting point | Not Available |
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Experimental Properties | Property | Value | Reference |
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Water Solubility | Not Available | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | Not Available |
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Organoleptic Properties | Not Available |
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SMPDB Pathways |
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KEGG Pathways | Amino sugar and nucleotide sugar metabolism | ec00520 | | Galactose metabolism | ec00052 | | Glycolysis / Gluconeogenesis | ec00010 | | Inositol phosphate metabolism | ec00562 | | Pentose phosphate pathway | ec00030 | |
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SMPDB Reactions |
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KEGG Reactions | Not Available |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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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 | aerobic | Baker's yeast | PMID: 11135551 | 2300 ± 200 µM | Synthetic medium with 2% glucose | aerobic;growing cells | Baker's yeast | PMID: 6229402 | 560 ± 80 µM | Synthetic medium with 2% glucose | aerobic;resting cells | Baker's yeast | PMID: 6229402 | 340 ± 130 µM | Synthetic medium with 2% glucose | anaerobic;resting cells | Baker's yeast | PMID: 6229402 | 1360 ± 600 µM | Synthetic medium with 2% galactose | aerobic;resting cells | Baker's yeast | PMID: 6229402 | Conversion Details Here |
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Extracellular Concentrations | Not Available |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS) | splash10-000b-1932000000-59f4881b86595037d013 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS) | splash10-0f7t-1933000000-4894135f21c21c369428 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS; 1 MEOX) | splash10-00di-9522000000-81266970683faa1f2aaf | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (6 TMS; 1 MEOX) | splash10-00di-9412000000-2f2a0e772025b48bf6f3 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS) | splash10-000j-1956000000-692b4df2b9c16f6a780c | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 6 TMS) | splash10-000i-1957000000-bd94955ffc1474153a48 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (6 TMS) | splash10-0v0a-0596000000-676527ddfc1d596e78f8 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-000b-1932000000-59f4881b86595037d013 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0f7t-1933000000-4894135f21c21c369428 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9522000000-81266970683faa1f2aaf | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00di-9412000000-2f2a0e772025b48bf6f3 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-000j-1956000000-692b4df2b9c16f6a780c | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-000i-1957000000-bd94955ffc1474153a48 | JSpectraViewer | MoNA | GC-MS | GC-MS Spectrum - GC-MS (Non-derivatized) | splash10-0v0a-0596000000-676527ddfc1d596e78f8 | JSpectraViewer | MoNA | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0005-9740000000-a6e81224fb97751dc2e6 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-001i-6252790000-ef5662fb1886367e07f2 | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated) | splash10-03di-0090000000-5653def80d1b5ff0eebb | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated) | splash10-000b-9200000000-66741d773ac31b347625 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated) | splash10-000t-9000000000-068809fcfaff0d387e6b | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative | splash10-0a4i-1090000000-d6e539d78b38c01dafea | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative | splash10-0002-9210000000-8b9ff1c5095f48a81fef | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative | splash10-0002-9000000000-f6e1147852f75db4c0a4 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative | splash10-002b-9000000000-1c52fd659f8a2b795e51 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Negative | splash10-004i-9000000000-d3f6a05e18ea6d56c56d | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive | splash10-0006-0890000000-5f3047c92c970dfe6927 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive | splash10-004i-0900000000-b84eb7685667fa7ee85e | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive | splash10-004i-2900000000-d4a0d51bb6e2da28533a | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive | splash10-004i-6900000000-dfb5bcbd9a7439c32352 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive | splash10-03gi-9600000000-a0922c82e185f6b5aa67 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-0006-0290000000-7ac7b397c52f29cd3822 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-052b-6590000000-5cdbc23378480ac55c4f | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive | splash10-004i-1900000000-b74270f21c6086362227 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-002b-9000000000-bc69e8fa215a3b82dcf2 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0a4i-0090000000-d6e539d78b38c01dafea | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QQ , negative | splash10-0002-9210000000-10019f92fd1eca143bab | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0490000000-94ea79ec673f4688b7a0 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dm-5940000000-c649262446626dcb8d6e | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0uka-9800000000-aae2cb792906d2dec6cd | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a6r-8290000000-8e20219f94b3fe964e38 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-b19b64f5cb4124047baf | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-ecb75a44e3d25affdf31 | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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References |
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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
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Synthesis Reference: | Not Available |
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External Links: | |
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