Record Information |
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Version | 1.0 |
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Created at | 2020-11-23 18:24:54 UTC |
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Updated at | 2021-08-12 19:51:36 UTC |
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NP-MRD ID | NP0002596 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | D-Fructose-1,6-bisphosphate |
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Provided By | BMRB |
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Description | Fructose 1,6-bisphosphate, also known as fosfructose, 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. Fructose 1,6-bisphosphate exists in all living organisms, ranging from bacteria to humans. In humans, fructose 1,6-bisphosphate is involved in the metabolic disorder called the glycogen storage disease type 1A (gsd1a) or von gierke disease pathway. Fructose 1,6-bisphosphate is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. D-Fructose-1,6-bisphosphate is found in Mus musculus. It was first documented in 1993 (PMID: 8412001). Based on a literature review a significant number of articles have been published on Fructose 1,6-bisphosphate (PMID: 15882454) (PMID: 17984079) (PMID: 14693576) (PMID: 11916152). |
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Structure | O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1 |
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Synonyms | Value | Source |
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1,6-Di-O-phosphono-beta-D-fructofuranose | ChEBI | BETA FRUCTOSE 1,6-diphosphATE | ChEBI | beta-D-Fructose 1,6-bisphosphate | ChEBI | Fosfructose | ChEBI | 1,6-Di-O-phosphono-b-D-fructofuranose | Generator | 1,6-Di-O-phosphono-β-D-fructofuranose | Generator | b FRUCTOSE 1,6-diphosphate | Generator | b FRUCTOSE 1,6-diphosphoric acid | Generator | beta FRUCTOSE 1,6-diphosphoric acid | Generator | Β fructose 1,6-diphosphate | Generator | Β fructose 1,6-diphosphoric acid | Generator | b-D-Fructose 1,6-bisphosphate | Generator | b-D-Fructose 1,6-bisphosphoric acid | Generator | beta-D-Fructose 1,6-bisphosphoric acid | Generator | Β-D-fructose 1,6-bisphosphate | Generator | Β-D-fructose 1,6-bisphosphoric acid | Generator | Fructose 1,6-bisphosphoric acid | Generator | SR-FDP | MeSH, HMDB | Fructose 1,6-diphosphate | MeSH, HMDB | Fructose-1,6-diphosphate, (L)-isomer | MeSH, HMDB | Fructose-1,6-diphosphate, (alpha-D)-isomer | MeSH, HMDB | Fructose-1,6-diphosphate, barium (1:2) salt | MeSH, HMDB | Fructose-1,6-diphosphate, sodium salt, monohydrate | MeSH, HMDB | Fructose-1,6-diphosphate, tetrasodium salt | MeSH, HMDB | Strontium fructose-1,6-diphosphate | MeSH, HMDB | Fructose-1,6-diphosphate, calcium salt | MeSH, HMDB | Fructose-1,6-diphosphate, disodium salt | MeSH, HMDB | Fructose-1,6-diphosphate, trisodium salt | MeSH, HMDB | Fructose 1,6-bisphosphate | MeSH | Fructose-1,6-diphosphate, 2-(18)O-labeled | MeSH, HMDB | Fructose-1,6-diphosphate, calcium (1:2) salt | MeSH, HMDB | Fructose-1,6-diphosphate, monosodium salt | MeSH, HMDB | Strontium fructose 1,6-diphosphate | MeSH, HMDB | Fructose-1,6-diphosphate magnesium salt | MeSH, HMDB | Fructose-1,6-diphosphate, (beta-D)-isomer | MeSH, HMDB | Fructose-1,6-diphosphate, tetrapotassium salt | MeSH, HMDB | Fructose-1,6-diphosphate | MeSH, HMDB | D-Fructose 1,6-biphosphate | HMDB | D-Fructose 1,6-bisphosphate | HMDB | D-Fructose 1,6-diphosphate | HMDB | Diphosphofructose | HMDB | Fructose 1,6-bis(dihydrogen phosphate) | HMDB | beta-D-Fructofuranose 1,6-bisphosphate | HMDB | beta-D-Fructofuranose 1,6-diphosphate | HMDB | beta-D-Fructose 1,6-diphosphate | HMDB | β-D-Fructofuranose 1,6-bisphosphate | HMDB, Generator | β-D-Fructofuranose 1,6-diphosphate | HMDB | β-D-Fructose 1,6-diphosphate | HMDB | b-D-Fructofuranose 1,6-bisphosphate | Generator | b-D-Fructofuranose 1,6-bisphosphoric acid | Generator | beta-D-Fructofuranose 1,6-bisphosphoric acid | Generator | Β-D-fructofuranose 1,6-bisphosphoric acid | Generator |
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Chemical Formula | C6H14O12P2 |
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Average Mass | 340.1157 Da |
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Monoisotopic Mass | 339.99605 Da |
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IUPAC Name | {[(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxy}phosphonic acid |
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Traditional Name | [(2R,3S,4S,5R)-3,4,5-trihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]methoxyphosphonic acid |
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CAS Registry Number | Not Available |
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SMILES | O[C@H]1[C@H](O)[C@@](O)(COP(O)(O)=O)O[C@@H]1COP(O)(O)=O |
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InChI Identifier | InChI=1S/C6H14O12P2/c7-4-3(1-16-19(10,11)12)18-6(9,5(4)8)2-17-20(13,14)15/h3-5,7-9H,1-2H2,(H2,10,11,12)(H2,13,14,15)/t3-,4-,5+,6-/m1/s1 |
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InChI Key | RNBGYGVWRKECFJ-ARQDHWQXSA-N |
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Experimental Spectra |
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| Spectrum Type | Description | Depositor Email | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, simulated) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 400 MHz, D2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Predicted Spectra |
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| Not Available | Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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Species Where Detected | |
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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 | Not Available |
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Substituents | Not Available |
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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 | Not Available |
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Experimental Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - 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;2:18. [PubMed:15882454 ]
- Nakai A, Shigematsu Y, Liu YY, Kikawa Y, Sudo M: Urinary sugar phosphates and related organic acids in fructose-1,6-diphosphatase deficiency. J Inherit Metab Dis. 1993;16(2):408-14. [PubMed:8412001 ]
- Ulrich EL, Akutsu H, Doreleijers JF, Harano Y, Ioannidis YE, Lin J, Livny M, Mading S, Maziuk D, Miller Z, Nakatani E, Schulte CF, Tolmie DE, Kent Wenger R, Yao H, Markley JL: BioMagResBank. Nucleic Acids Res. 2008 Jan;36(Database issue):D402-8. doi: 10.1093/nar/gkm957. Epub 2007 Nov 4. [PubMed:17984079 ]
- Riedel BJ, Gal J, Ellis G, Marangos PJ, Fox AW, Royston D: Myocardial protection using fructose-1,6-diphosphate during coronary artery bypass graft surgery: a randomized, placebo-controlled clinical trial. Anesth Analg. 2004 Jan;98(1):20-9, table of contents. doi: 10.1213/01.ane.0000094336.97693.90. [PubMed:14693576 ]
- Acan NL, Ozer N: Modification of human erythrocyte pyruvate kinase by an active site-directed reagent: bromopyruvate. J Enzyme Inhib. 2001 Nov;16(5):457-64. doi: 10.1080/14756360109162395. [PubMed:11916152 ]
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