| Record Information |
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| Version | 4.0 |
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| Status | Expected but not Quantified |
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| Creation Date | 2005-11-16 15:48:42 UTC |
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| Update Date | 2020-02-26 21:22:53 UTC |
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| HMDB ID | HMDB0001047 |
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| Secondary Accession Numbers | |
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| Metabolite Identification |
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| Common Name | D-Fructose 2,6-bisphosphate |
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| Description | D-Fructose 2,6-bisphosphate, also known as phosphofructokinase activator, 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. D-Fructose 2,6-bisphosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). D-Fructose 2,6-bisphosphate exists in all living species, ranging from bacteria to humans. D-fructose 2,6-bisphosphate can be converted into fructose 6-phosphate; which is mediated by the enzyme 6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 1. In humans, D-fructose 2,6-bisphosphate is involved in fructose intolerance, hereditary. The breakdown of Fru-2,6-P2 is catalyzed by the phosphorylation of the bifunctional enzyme, which allows FBPase-2 to dephosphorylate fructose 2,6-bisphosphate to produce fructose 6-phosphate and Pi. Fru-2,6-P2 production is activated when plants are in the dark and photosynthesis and triose phosphates are not produced. The remaining 1/6 of triose phosphate can be converted into sucrose or stored as starch. One such gene is for the expression of TP53-induced glycolysis and apoptosis regulator (TIGAR); an enzyme that inhibits glycolysis, monitors the cellular levels of reactive oxygen species, and protects cells from apoptosis. This kinase phosphorylates the PFK-2/FBPase-2 enzyme at an NH2-terminal Ser residue with ATP to activate the FBPase-2 activity and inhibit the PFK-2 activity of the enzyme, thus reducing levels of Fru-2,6-P2 in the cell. |
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| Structure | |
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| Synonyms | | Value | Source |
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| 2,6-Di-O-phosphono-beta-D-fructofuranose | ChEBI | | 2,6-Di-O-phosphono-b-D-fructofuranose | Generator | | 2,6-Di-O-phosphono-β-D-fructofuranose | Generator | | D-Fructose 2,6-bisphosphoric acid | Generator | | b-D-Fructose 2,6-bisphosphate | HMDB | | beta-D-Fructose 2,6-bisphosphate | HMDB | | Fru 2,6-P2, fructose 2,6-diphosphate | HMDB | | Fructose 2,6-bisphosphate | HMDB | | Fructose 2,6-biphosphate | HMDB | | Fructose 2,6-diphosphate | HMDB | | Phosphofructokinase activation factor | HMDB | | Phosphofructokinase activator | HMDB | | Fructose-2,6-diphosphate | HMDB |
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| Chemical Formula | C6H14O12P2 |
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| Average Molecular Weight | 340.1157 |
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| Monoisotopic Molecular Weight | 339.996048936 |
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| IUPAC Name | {[(2R,3S,4S,5S)-3,4-dihydroxy-5-(hydroxymethyl)-5-(phosphonooxy)oxolan-2-yl]methoxy}phosphonic acid |
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| Traditional Name | fructose-2,6-diphosphate |
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| CAS Registry Number | Not Available |
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| SMILES | OC[C@@]1(OP(O)(O)=O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O |
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| InChI Identifier | InChI=1S/C6H14O12P2/c7-2-6(18-20(13,14)15)5(9)4(8)3(17-6)1-16-19(10,11)12/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 | YXWOAJXNVLXPMU-ZXXMMSQZSA-N |
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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
- Organoheterocyclic compound
- Oxacycle
- Primary alcohol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Aliphatic heteromonocyclic compound
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| Molecular Framework | Aliphatic heteromonocyclic compounds |
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| External Descriptors | |
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| Ontology |
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| Disposition | Source: Biological location: |
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| Process | Naturally occurring process: |
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| Physical Properties |
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| State | Solid |
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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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| | Spectrum Type | Description | Splash Key | View |
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| GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-01dj-0963000000-090736f476a618727455 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00tb-0972000000-e47c74a14376eaabd8c3 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-01dj-0963000000-090736f476a618727455 | Spectrum | | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-00tb-0972000000-e47c74a14376eaabd8c3 | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0002-9512000000-82418e0e398490357c5e | Spectrum | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0006-2190010000-53cf738181713979e181 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-3797000000-cb11e27ce8d0be902a39 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0002-9132000000-b908246df46f54e31180 | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-00dm-9600000000-19262e5981934144e1aa | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-002r-7409000000-0240bd8771cde252759c | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-8930f98e412f1b68e30b | Spectrum | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-fb204edc71835bcbaaad | Spectrum | | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum |
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| Synthesis Reference | Shulman, Hagit; Makarov, Carina; Ogawa, Anthony K.; Romesberg, Floyd; Keinan, Ehud. Chemically Reactive Immunogens Lead to Functional Convergence of the Immune Response. Journal of the American Chemical Society (2000), 122(44), 10743-10753. |
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