| Revision as of 09:40, 2 December 2010 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Script assisted update of identifiers from ChemSpider, CommonChemistry and FDA for the Chem/Drugbox validation project - Updated: InChI1->InChI StdInChI StdInChIKey.← Previous edit |
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{{chembox |
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{{chembox |
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| verifiedrevid = 400096119 |
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|ImageFile=Fructose-1-phosphate.png |
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| ImageFile = Fructose-1-phosphate.png |
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|ImageSize= |
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| ImageSize = |
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|IUPACName=methoxyphosphonic acid |
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| IUPACName = Fructose 1-(dihydrogen phosphate) |
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|OtherNames= |
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| SystematicName = (3''S'',4''R'',5''R'')-3,4,5,6-Tetrahydroxy-2-oxohexyl dihydrogen phosphate |
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|Section1= {{Chembox Identifiers |
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| ChemSpiderID = 58741 |
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| OtherNames = |
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|Section1={{Chembox Identifiers |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 58741 |
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| InChI = 1/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3,5-8,10-11H,1-2H2,(H2,12,13,14)/t3-,5-,6-/m1/s1 |
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| InChI = 1/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3,5-8,10-11H,1-2H2,(H2,12,13,14)/t3-,5-,6-/m1/s1 |
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| InChIKey = ZKLLSNQJRLJIGT-UYFOZJQFBV |
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| InChIKey = ZKLLSNQJRLJIGT-UYFOZJQFBV |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3,5-8,10-11H,1-2H2,(H2,12,13,14)/t3-,5-,6-/m1/s1 |
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| StdInChI = 1S/C6H13O9P/c7-1-3(8)5(10)6(11)4(9)2-15-16(12,13)14/h3,5-8,10-11H,1-2H2,(H2,12,13,14)/t3-,5-,6-/m1/s1 |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = ZKLLSNQJRLJIGT-UYFOZJQFSA-N |
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| StdInChIKey = ZKLLSNQJRLJIGT-UYFOZJQFSA-N |
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| CASNo=15978-08-2 |
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| CASNo = 15978-08-2 |
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| PubChem = 65246 |
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| PubChem = 65246 |
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| SMILES = O=P(O)(O)OCC(=O)(O)(O)(O)CO |
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| SMILES = O=P(O)(O)OCC(=O)(O)(O)(O)CO |
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| MeSHName=Fructose-1-phosphate |
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| MeSHName = Fructose-1-phosphate |
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|Section2= {{Chembox Properties |
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|Section2={{Chembox Properties |
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| Formula=C<sub>6</sub>H<sub>13</sub>O<sub>9</sub>P |
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| Formula=C<sub>6</sub>H<sub>13</sub>O<sub>9</sub>P |
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| MolarMass=260.136 |
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| MolarMass=260.136 |
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|Section3= {{Chembox Hazards |
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|Section3={{Chembox Hazards |
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'''Fructose-1-phosphate''' is a derivative of ]. It is generated mainly by ] but is also generated in smaller amounts in the small intestinal mucosa and proximal epithelium of the renal tubule.<ref name="Marks"/> It is an important intermediate of glucose metabolism. Because fructokinase has a high ] fructose entering cells is quickly phosphorylated to fructose 1-phosphate.<ref name="Marks">"Marks A. Basic Medical Biochemistry: a clinical approach, 3rd ed. p.540</ref> In this form it is usually accumulated in the liver until it undergoes further conversion by ] (the rate limiting enzyme of fructose metabolism). |
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'''Fructose-1-phosphate''' is a derivative of ]. It is generated by ]. |
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Aldolase B converts it into ] and ] (DHAP). Glyceraldehyde is then phosphorylated by triose kinase to glyceraldehyde 3-phosphate. Metabolism of fructose thus essentially results in intermediates of ]. This means that fructose has the same fate as glucose after it gets metabolised. The final product of glycolysis (pyruvate) may then undergo ], enter the ] or be stored as fatty acids. |
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It is converted by ] into ] and ] (DHAP). |
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==Clinical significance== |
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In ] caused by defects in aldolase B, fructose 1-phosphate accumulates in the liver and causes a number of adverse defects. Hypoglycemia results from inhibition of glycogenolysis and gluconeogenesis. It depletes intracellular phosphate reserves which leads to loss of ATP and inhibition of biosynthetic pathways. Symptoms of hereditary fructose intolerance are apathy, drowsiness, sweatiness and tremulousness.<ref name="Marks"/> |
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== References== |
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{{reflist}} |
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{{biochem-stub}} |
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{{Fructose and galactose metabolic intermediates}} |
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{{Fructose and galactose metabolic intermediates}} |
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{{DEFAULTSORT:Fructosephosphate1}} |
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