Identification |
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YMDB ID | YMDB00108 |
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Name | Fructose 1,6-bisphosphate |
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Species | Saccharomyces cerevisiae |
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Strain | Baker's yeast |
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Description | Fructose 1,6-bisphosphate (also known as Harden-young ester) is a fructose sugar phosphorylated on carbons 1 and 6. The β-D-form of this compound is very common in cells. The vast majority of glucose and fructose entering a cell will become converted to fructose 1,6-biphosphate at some point. Fructose 1,6-bisphosphate lies within the glycolysis metabolic pathway and is produced by phosphorylation of fructose 6-phosphate. It is, in turn, broken down into two compounds: glyceraldehyde 3-phosphate and dihydroxyacetone phosphate. It is an allosteric activator of pyruvate kinase. [Wikipedia] |
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Structure | |
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Synonyms | - D-Fructose 1,6-biphosphate
- D-Fructose 1,6-bis(dihydrogen phosphate)
- D-Fructose 1,6-bisphosphate
- D-Fructose 1,6-diphosphate
- D-fructose-1,6-bisphosphate
- D-fructose-1,6-diphosphate
- Diphosphofructose
- Esafosfan
- Esafosfina
- FDP
- Fosfructose
- Fructose 1,6-bis
- Fructose 1,6-bisphosphate
- Fructose 1,6-diphosphate
- Fructose 1,6-diphosphic acid
- Harden-Young ester
- 2,5-Anhydroglucitol-1,6-biphosphoric acid
- Fructose 1,6-bisphosphoric acid
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CAS number | 488-69-7 |
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Weight | Average: 324.1163 Monoisotopic: 324.001134314 |
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InChI Key | WSMBXSQDFPTODV-JGWLITMVSA-N |
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InChI | InChI=1S/C6H14O11P2/c7-5-3(1-15-18(9,10)11)17-4(6(5)8)2-16-19(12,13)14/h3-8H,1-2H2,(H2,9,10,11)(H2,12,13,14)/t3-,4+,5-,6-/m1/s1 |
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IUPAC Name | {[(2S,3S,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid |
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Traditional IUPAC Name | [(2S,3S,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid |
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Chemical Formula | C6H14O11P2 |
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SMILES | [H]O[C@@]1([H])[C@]([H])(O[H])[C@]([H])(O[C@@]1([H])C([H])([H])OP(=O)(O[H])O[H])C([H])([H])OP(=O)(O[H])O[H] |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose 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 | Pentose phosphates |
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Alternative Parents | |
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Substituents | - Pentose phosphate
- Pentose-5-phosphate
- C-glycosyl compound
- Glycosyl compound
- Monosaccharide phosphate
- Monoalkyl phosphate
- Phosphoric acid ester
- Organic phosphoric acid derivative
- Alkyl phosphate
- Tetrahydrofuran
- Secondary alcohol
- 1,2-diol
- Organoheterocyclic compound
- Oxacycle
- Ether
- Dialkyl ether
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State | Solid |
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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 | 94 mg/mL [sodium salt, HMP experimental] | PhysProp | LogP | Not Available | PhysProp |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations | |
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Organoleptic Properties | Not Available |
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SMPDB Pathways | |
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KEGG Pathways | Not Available |
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SMPDB Reactions | |
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KEGG Reactions | |
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Concentrations |
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Intracellular Concentrations | Intracellular Concentration | Substrate | Growth Conditions | Strain | Citation |
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90 ± 70 µM | Minimal medium supplemented with ammonia salts | aerobic;resting cells | Baker's yeast | PMID: 4578278 | 3800 ± 3200 µM | Minimal medium supplemented with ammonia salts and glucose | aerobic and anaerobic;resting cells | Baker's yeast | PMID: 4578278 | 50 ± 0 µM | Minimal medium supplemented with ammonia salts and ethanol | aerobic;growing cells | Baker's yeast | PMID: 4578278 | 3500 ± 1000 µM | Minimal medium supplemented with ammonia salts and (glucose or galactose) | aerobic;growing cells | Baker's yeast | PMID: 4578278 | 1700 ± 10 µM | Synthetic medium with 2% glucose | aerobic;growing cells | Baker's yeast | PMID: 6229402 | 410 ± 70 µM | Synthetic medium with 2% glucose | aerobic;resting cells | Baker's yeast | PMID: 6229402 | 530 ± 130 µM | Synthetic medium with 2% glucose | anaerobic;resting cells | Baker's yeast | PMID: 6229402 | 2700 ± 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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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9510000000-b61ac58bde76d2a1b23e | JSpectraViewer | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-0092-0249000000-eb939046a288ed654b99 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-004i-0900000000-5576a6262edb99fd1ef1 | JSpectraViewer | MoNA | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-004i-0900000000-5576a6262edb99fd1ef1 | JSpectraViewer | MoNA | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-1449000000-b8c014f1b120b99df234 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-004i-7394000000-8cf301778bf04bd017a9 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0fi0-7900000000-59986d4e4c4309b9f814 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00fr-6109000000-76c96c0eb2ab1ac20db1 | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-5677f1663b32f68073ad | JSpectraViewer | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-29c2267c283eb5e5b173 | JSpectraViewer | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | 1D NMR | 1H 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
- Blazquez, M. A., Lagunas, R., Gancedo, C., Gancedo, J. M. (1993). "Trehalose-6-phosphate, a new regulator of yeast glycolysis that inhibits hexokinases." FEBS Lett 329:51-54.8354408
- Goncalves, P., Planta, R. J. (1998). "Starting up yeast glycolysis." Trends Microbiol 6:314-319.9746941
- Fonzi, W. A., Shanley, M., Opheim, D. J. (1979). "Relationship of glycolytic intermediates, glycolytic enzymes, and ammonia to glycogen metabolism during sporulation in the yeast Saccharomyces cerevisiae." J Bacteriol 137:285-294.368017
- 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
- Inoue, Y., Watanabe, K., Shimosaka, M., Saikusa, T., Fukuda, Y., Murata, K., Kimura, A. (1985). "Metabolism of 2-oxoaldehydes in yeasts. Purification and characterization of lactaldehyde dehydrogenase from Saccharomyces cerevisiae." Eur J Biochem 153:243-247.3908097
- Gancedo, J. M., Gancedo, C. (1973). "Concentrations of intermediary metabolites in yeast." Biochimie 55:205-211.4578278
- 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
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Synthesis Reference: | Yan, Weiqun. Method for producing fructose-1,6-diphosphate (FDP). Faming Zhuanli Shenqing Gongkai Shuomingshu (2005), 7 pp. |
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