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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 21:22:55 UTC |
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HMDB ID | HMDB0001076 |
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Secondary Accession Numbers | - HMDB0062538
- HMDB01076
- HMDB62538
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Metabolite Identification |
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Common Name | Fructose 1-phosphate |
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Description | Fructose 1-phosphate, also known as D-fructose-1-p, 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-phosphate is an extremely weak basic (essentially neutral) compound (based on its pKa). Metabolism of fructose thus essentially results in intermediates of glycolysis. The final product of glycolysis (pyruvate) may then undergo gluconeogenesis, enter the TCA cycle or be stored as fatty acids. Fructose 1-phosphate exists in all living organisms, ranging from bacteria to humans. Within humans, fructose 1-phosphate participates in a number of enzymatic reactions. In particular, fructose 1-phosphate can be biosynthesized from D-fructose through the action of the enzyme ketohexokinase. In addition, fructose 1-phosphate can be converted into dihydroxyacetone phosphate and glyceraldehyde; which is catalyzed by the enzyme fructose-bisphosphate aldolase a. Because fructokinase has a high Vmax fructose entering cells is quickly phosphorylated to fructose 1-phosphate. In humans, fructose 1-phosphate is involved in fructose intolerance, hereditary. Hypoglycemia results from inhibition of glycogenolysis and gluconeogenesis. It is generated mainly by hepatic fructokinase but is also generated in smaller amounts in the small intestinal mucosa and proximal epithelium of the renal tubule. Aldolase B converts it into glyceraldehyde and dihydroxyacetone phosphate (DHAP). Symptoms of hereditary fructose intolerance are apathy, drowsiness, sweatiness and tremulousness. |
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Structure | |
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Synonyms | Value | Source |
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beta-D-Fructose 1-phosphate | ChEBI | b-D-Fructose 1-phosphate | Generator | b-D-Fructose 1-phosphoric acid | Generator | beta-D-Fructose 1-phosphoric acid | Generator | Β-D-fructose 1-phosphate | Generator | Β-D-fructose 1-phosphoric acid | Generator | Fructose 1-phosphoric acid | Generator | D-Fructose 1-phosphate | HMDB | D-Fructose-1-p | HMDB | D-Fructose-1-phosphate | HMDB | Fructose-1-p | HMDB | Fructose-1-phosphate | HMDB |
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Chemical Formula | C6H13O9P |
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Average Molecular Weight | 260.1358 |
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Monoisotopic Molecular Weight | 260.029718526 |
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IUPAC Name | {[(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxy}phosphonic acid |
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Traditional Name | [(2R,3S,4S,5R)-2,3,4-trihydroxy-5-(hydroxymethyl)oxolan-2-yl]methoxyphosphonic acid |
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CAS Registry Number | 15978-08-2 |
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SMILES | OC[C@H]1O[C@](O)(COP(O)(O)=O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C6H13O9P/c7-1-3-4(8)5(9)6(10,15-3)2-14-16(11,12)13/h3-5,7-10H,1-2H2,(H2,11,12,13)/t3-,4-,5+,6-/m1/s1 |
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InChI Key | RHKKZBWRNHGJEZ-ARQDHWQXSA-N |
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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
- Pentose phosphate
- Pentose-5-phosphate
- C-glycosyl compound
- Glycosyl compound
- Monosaccharide phosphate
- Pentose monosaccharide
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Alkyl phosphate
- Phosphoric acid ester
- Tetrahydrofuran
- Secondary alcohol
- Hemiacetal
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Alcohol
- Hydrocarbon derivative
- Organic oxide
- Primary alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | Not Available |
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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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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03di-9510000000-71d828159b61f8342118 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-001i-2912320000-08ffe3d23f5fa5d6162c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03dm-9470000000-18ac582a370338a3f5f1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01oy-7390000000-1a5a72af8bb734e50eb8 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-009y-9100000000-4f151f373d7730140f38 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0a6r-9270000000-5af91634007091008210 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9000000000-5cf3f457b8c6f6270b68 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-4e6feccf18943de8c419 | Spectrum |
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Biological Properties |
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Cellular Locations | - Cytoplasm (predicted from logP)
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Biospecimen Locations | Not Available |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022410 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 8575807 |
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KEGG Compound ID | C01094 |
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BioCyc ID | FRU1P |
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BiGG ID | 40936 |
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Wikipedia Link | Fructose 1-phosphate |
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METLIN ID | 378 |
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PubChem Compound | 10400369 |
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PDB ID | Not Available |
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ChEBI ID | 139419 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Hara, Yoshito. Ion exchange separation of fructose 1-phosphate by using borate as the eluant. Journal of Biochemistry (Tokyo, Japan) (1959), 46 571-3. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | - Alvarez E, Roncero I, Chowen JA, Vazquez P, Blazquez E: Evidence that glucokinase regulatory protein is expressed and interacts with glucokinase in rat brain. J Neurochem. 2002 Jan;80(1):45-53. [PubMed:11796742 ]
- Malaisse WJ: [Metabolic interactions between glucose and fructose]. Bull Mem Acad R Med Belg. 2002;157(7-9):349-52; discussion 352-3. [PubMed:12647375 ]
- Watford M: Small amounts of dietary fructose dramatically increase hepatic glucose uptake through a novel mechanism of glucokinase activation. Nutr Rev. 2002 Aug;60(8):253-7. [PubMed:12199300 ]
- 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 ]
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