Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:45:48 -0600 |
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Update Date | 2015-06-03 15:53:45 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | 6-Phosphonoglucono-D-lactone |
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Description | 6-phosphoglucono-delta-lactone (d-6PGL) is the immediate product of the Glucose-6-phosphate dehydrogenase (G-6-PD), the first enzyme of the hexose monophosphate pathway. (PMID 3711719) |
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Structure | |
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Synonyms: | - 6-(Dihydrogen phosphate)-(8CI)-D-Gluconate delta-lactone
- 6-(Dihydrogen phosphate)-(8ci)-D-gluconate δ-lactone
- 6-(Dihydrogen phosphate)-(8CI)-D-Gluconic acid delta-lactone
- 6-(Dihydrogen phosphate)-(9CI)-D-Gluconate D-lactone
- 6-(Dihydrogen phosphate)-(9ci)-D-gluconate delta-lactone
- 6-(Dihydrogen phosphate)-(9ci)-D-gluconate δ-lactone
- 6-(Dihydrogen phosphate)-(9CI)-D-Gluconic acid D-lactone
- 6-(dihydrogen phosphate)-(9CI)-D-Gluconic acid delta-lactone
- 6-(Dihydrogen phosphate)-D-Gluconate delta-lactone
- 6-(Dihydrogen phosphate)-D-gluconate δ-lactone
- 6-(Dihydrogen phosphate)-D-Gluconic acid delta-lactone
- 6-(Dihydrogen phosphoric acid)-(8ci)-D-gluconic acid delta-lactone
- 6-(Dihydrogen phosphoric acid)-(8ci)-D-gluconic acid δ-lactone
- 6-(Dihydrogen phosphoric acid)-(9ci)-D-gluconic acid D-lactone
- 6-(Dihydrogen phosphoric acid)-(9ci)-D-gluconic acid delta-lactone
- 6-(Dihydrogen phosphoric acid)-(9ci)-D-gluconic acid δ-lactone
- 6-(Dihydrogen phosphoric acid)-D-gluconic acid delta-lactone
- 6-(Dihydrogen phosphoric acid)-D-gluconic acid δ-lactone
- 6-Pgdl
- 6-Phospho-D-glucono-1,5-lactone
- 6-Phosphoglucono-delta-lactone
- 6-phosphoglucono-δ-Lactone
- 6-Phosphogluconolactone
- 6-Phosphonoglucono-delta-lactone
- 6-phosphonoglucono-δ-Lactone
- D-6-P-glucono-δ-lactone
- D-6-P-Glucono-delta-lactone
- D-6-P-glucono-δ-Lactone
- D-6-phospho-glucono-δ-lactone
- D-6-Phospho-glucono-delta-lactone
- D-6-phospho-glucono-δ-Lactone
- D-6-phosphoglucono-δ-lactone
- D-6-Phosphoglucono-delta-lactone
- D-6-phosphoglucono-δ-Lactone
- D-glucono-δ-lactone-6-phosphate
- D-glucono-δ-lactone-6-phosphoric acid
- D-Glucono-1,5-lactone 6-phosphate
- D-glucono-1,5-Lactone 6-phosphoric acid
- D-Glucono-1,5-lactone-6-phosphate
- D-glucono-1,5-Lactone-6-phosphoric acid
- D-Glucono-delta-lactone-6-phosphate
- D-glucono-delta-Lactone-6-phosphoric acid
- D-glucono-δ-Lactone-6-phosphate
- D-glucono-δ-Lactone-6-phosphoric acid
- Delta-Gluconolactone 6-phosphate
- delta-Gluconolactone 6-phosphoric acid
- δ-Gluconolactone 6-phosphate
- δ-Gluconolactone 6-phosphoric acid
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Chemical Formula: | C6H11O9P |
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Weight: | Average: 258.1199 Monoisotopic: 258.014068462 |
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InChI Key: | IJOJIVNDFQSGAB-SQOUGZDYSA-N |
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InChI: | InChI=1S/C6H11O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-5,7-9H,1H2,(H2,11,12,13)/t2-,3-,4+,5-/m1/s1 |
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CAS number: | 2641-81-8 |
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IUPAC Name: | {[(2R,3S,4S,5R)-3,4,5-trihydroxy-6-oxooxan-2-yl]methoxy}phosphonic acid |
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Traditional IUPAC Name: | 6-phosphogluconolactone |
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SMILES: | O[C@H]1[C@H](O)[C@@H](COP(O)(O)=O)OC(=O)[C@@H]1O |
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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
- Gluconolactone
- Monosaccharide phosphate
- Delta valerolactone
- Delta_valerolactone
- Monoalkyl phosphate
- Alkyl phosphate
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Oxane
- Secondary alcohol
- Carboxylic acid ester
- Lactone
- Organoheterocyclic compound
- Carboxylic acid derivative
- Monocarboxylic acid or derivatives
- Oxacycle
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Alcohol
- Carbonyl group
- 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: | Solid |
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Charge: | -2 |
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Melting point: | Not Available |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | |
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KEGG Pathways: | - Glutathione metabolism ec00480
- Metabolic pathways eco01100
- Microbial metabolism in diverse environments ec01120
- Pentose phosphate pathway ec00030
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EcoCyc Pathways: | |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9410000000-eed74c30dd7f6e1f6308 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0gb9-4962700000-904ef84e4218dd793e1f | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0a4l-0490000000-b7b9499f5fb3885d4a30 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-06r7-5940000000-effb433b86b6c959da1d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0ukc-7900000000-4009a042c78eba5dae17 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a6r-7290000000-09bacc885b7c74c16ece | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-5f41258b7bf2096e04fd | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-82b3c16e1939174dae85 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-5090000000-381acc8a668fbac0de38 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-056s-9030000000-d9d231d9c36c323e6446 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-f53a8156649b945c2aee | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dl-0900000000-8f89af904744e22d72b5 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03di-3900000000-8d2bf1400d030127126a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0002-9000000000-95f15475c3f10c3ac1bd | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Beutler, E., Kuhl, W. (1986). "Characteristics and significance of the reverse glucose-6-phosphate dehydrogenase reaction." J Lab Clin Med 107:502-507. Pubmed: 3711719
- 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
- Miclet E, Stoven V, Michels PA, Opperdoes FR, Lallemand JY, Duffieux F: NMR spectroscopic analysis of the first two steps of the pentose-phosphate pathway elucidates the role of 6-phosphogluconolactonase. J Biol Chem. 2001 Sep 14;276(37):34840-6. Epub 2001 Jul 16. Pubmed: 11457850
- Nakayama Y, Kinoshita A, Tomita M: Dynamic simulation of red blood cell metabolism and its application to the analysis of a pathological condition. Theor Biol Med Model. 2005 May 9;2(1):18. Pubmed: 15882454
- Rakitzis ET, Papandreou P: Kinetic analysis of 6-phosphogluconolactone hydrolysis in hemolysates. Biochem Mol Biol Int. 1995 Nov;37(4):747-55. Pubmed: 8589648
- Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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