Record Information |
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Version | 1.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-07-01 14:27:12 UTC |
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NP-MRD ID | NP0000878 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Fructose 6-phosphate |
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Description | Fructose 6-phosphate (F6P) 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. F6P is a derivative of fructose, which has been phosphorylated at the 6-hydroxy group. Fructose 6-phosphate is a fundamental metabolite and exists in all living species, ranging from bacteria to plants to humans. The great majority of glucose is converted to fructose 6-phosphate as part of the glycolytic metabolic pathway (glycolysis). Specifically, F6P is produce is produced by the isomerisation of glucose 6-phosphate via the enzyme phosphoglucose isomerase. F6P is in turn further phosphorylated to fructose-1,6-bisphosphate by the enzyme phosphofructokinase-1. Glycolysis is the metabolic pathway that converts glucose into pyruvic acid. The free energy released in this process is used to form ATP and reduced nicotinamide adenine dinucleotide (NADH). In addition to its key involvement in glycolysis, fructose 6-phosphate can also be biosynthesized from glucosamine 6-phosphate via the enzyme glucosamine-6-phosphate isomerase 1. In addition, fructose 6-phosphate and L-glutamine can be converted into glucosamine 6-phosphate and L-glutamic acid through the action of the enzyme glutamine--fructose-6-phosphate aminotransferase. |
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Structure | OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1 |
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Synonyms | Value | Source |
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D-Fructose 6-phosphate | ChEBI | D-Fructose 6-phosphoric acid | ChEBI | Fructose-6-phosphate | ChEBI | Neuberg ester | ChEBI | Fructose-6-phosphoric acid | Generator | Fructose 6-phosphoric acid | Generator | D-Fructose 6-phosphorate | HMDB | D-Fructose-6-p | HMDB | D-Fructose-6-phosphate | HMDB | FPC | HMDB | Fru-6-p | HMDB | Fructose-6-p | HMDB | Fructose-6P | HMDB | Fructose-6-phosphate, (alpha-D)-isomer | HMDB | Fructose-6-phosphate, (beta-D)-isomer | HMDB | Fructose-6-phosphate, disodium salt, (D)-isomer | HMDB | Fructose-6-phosphate, (D)-isomer | HMDB | Fructose-6-phosphate, 1-(14)C-labeled, (D)-isomer | HMDB | Fructose-6-phosphate, 2-(14)C-labeled, (D)-isomer | HMDB | Fructose-6-phosphate, barium (1:1) salt, (D)-isomer | HMDB | Fructose-6-phosphate, barium salt, (D)-isomer | HMDB | Fructose-6-phosphate, sodium salt, (D)-isomer | HMDB | Fructose-6-phosphate, calcium salt, (D)-isomer | HMDB | Fructose-6-phosphate, magnesium (1:1) salt, (D)-isomer | HMDB | Fructose-6-phosphate, sodium salt | HMDB |
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Chemical Formula | C6H13O9P |
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Average Mass | 260.1358 Da |
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Monoisotopic Mass | 260.02972 Da |
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IUPAC Name | {[(2R,3R,4S)-2,3,4,6-tetrahydroxy-5-oxohexyl]oxy}phosphonic acid |
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Traditional Name | D-fructose 6-phosphate |
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CAS Registry Number | 643-13-0 |
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SMILES | OCC(=O)[C@@H](O)[C@H](O)[C@H](O)COP(O)(O)=O |
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InChI Identifier | InChI=1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h4-7,9-11H,1-2H2,(H2,12,13,14)/t4-,5-,6-/m1/s1 |
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InChI Key | GSXOAOHZAIYLCY-HSUXUTPPSA-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, 500 MHz, H2O, experimental) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 2D NMR | [1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, 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 | |
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Substituents | - Hexose phosphate
- Monosaccharide phosphate
- Monoalkyl phosphate
- Acyloin
- Beta-hydroxy ketone
- Organic phosphoric acid derivative
- Phosphoric acid ester
- Alkyl phosphate
- Alpha-hydroxy ketone
- Ketone
- Secondary alcohol
- Polyol
- Hydrocarbon derivative
- Organic oxide
- Carbonyl group
- Primary alcohol
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | |
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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 | 911 mg/mL | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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General References | - Sreekumar A, Poisson LM, Rajendiran TM, Khan AP, Cao Q, Yu J, Laxman B, Mehra R, Lonigro RJ, Li Y, Nyati MK, Ahsan A, Kalyana-Sundaram S, Han B, Cao X, Byun J, Omenn GS, Ghosh D, Pennathur S, Alexander DC, Berger A, Shuster JR, Wei JT, Varambally S, Beecher C, Chinnaiyan AM: Metabolomic profiles delineate potential role for sarcosine in prostate cancer progression. Nature. 2009 Feb 12;457(7231):910-4. doi: 10.1038/nature07762. [PubMed:19212411 ]
- 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 ]
- Roberts NB, Dutton J, Helliwell T, Rothwell PJ, Kavanagh JP: Pyrophosphate in synovial fluid and urine and its relationship to urinary risk factors for stone disease. Ann Clin Biochem. 1992 Sep;29 ( Pt 5):529-34. [PubMed:1332571 ]
- Sanchez B, Champomier-Verges MC, Anglade P, Baraige F, de Los Reyes-Gavilan CG, Margolles A, Zagorec M: Proteomic analysis of global changes in protein expression during bile salt exposure of Bifidobacterium longum NCIMB 8809. J Bacteriol. 2005 Aug;187(16):5799-808. [PubMed:16077128 ]
- Markuszewski MJ, Szczykowska M, Siluk D, Kaliszan R: Human red blood cells targeted metabolome analysis of glycolysis cycle metabolites by capillary electrophoresis using an indirect photometric detection method. J Pharm Biomed Anal. 2005 Sep 15;39(3-4):636-42. [PubMed:15925468 ]
- Wamelink MM, Struys EA, Huck JH, Roos B, van der Knaap MS, Jakobs C, Verhoeven NM: Quantification of sugar phosphate intermediates of the pentose phosphate pathway by LC-MS/MS: application to two new inherited defects of metabolism. J Chromatogr B Analyt Technol Biomed Life Sci. 2005 Aug 25;823(1):18-25. Epub 2005 Jan 23. [PubMed:16055050 ]
- Karlander S, Roovete A, Vranic M, Efendic S: Glucose and fructose 6-phosphate cycle in humans. Am J Physiol. 1986 Nov;251(5 Pt 1):E530-6. [PubMed:3777162 ]
- Gapparov MM, Virovets OA: [Nonenzymatic glycosylation of serum albumin and thymic DNA by food monosugars and their natural metabolites that form in the body]. Vopr Pitan. 1990 Jan-Feb;(1):36-40. [PubMed:2346009 ]
- Alton G, Hasilik M, Niehues R, Panneerselvam K, Etchison JR, Fana F, Freeze HH: Direct utilization of mannose for mammalian glycoprotein biosynthesis. Glycobiology. 1998 Mar;8(3):285-95. [PubMed:9451038 ]
- Gagnon M, Kheadr EE, Le Blay G, Fliss I: In vitro inhibition of Escherichia coli O157:H7 by bifidobacterial strains of human origin. Int J Food Microbiol. 2004 Apr 1;92(1):69-78. [PubMed:15033269 ]
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