Record Information |
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Version | 2.0 |
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Created at | 2005-11-16 15:48:42 UTC |
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Updated at | 2021-06-29 00:46:56 UTC |
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NP-MRD ID | NP0001436 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Glucosamine 6-phosphate |
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Description | Glucosamine 6-phosphate (CAS: 3616-42-0) Is normally produced in endothelial cells via de novo glucosamine synthesis by the enzyme fructose-6-phosphate amidotransferase and the modulation of this pathway by hyperglycemia and glutamine. Glutamine-fructose-6-phosphate amidotransferase (GFAT) catalyzes the first committed step in the pathway for biosynthesis of hexosamines in mammals.It is a member of the N-terminal nucleophile class of amidotransferases, GFAT transfers the amino group from the L-glutamine amide to D-fructose 6-phosphate, producing glutamic acid and glucosamine 6-phosphate. As glucosamine inhibits endothelial nitric oxide synthesis it has important implications for impaired endothelium-dependent relaxation and vascular dysfunction in diabetes mellitus (PMID: 11270676 , 11842094 ). |
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Structure | N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1 |
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Synonyms | Value | Source |
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2-Amino-2-deoxy-6-O-phosphono-alpha-D-glucopyranose | ChEBI | alpha-D-Glucosamine 6-(dihydrogen phosphate) | ChEBI | 2-Amino-2-deoxy-6-O-phosphono-a-D-glucopyranose | Generator | 2-Amino-2-deoxy-6-O-phosphono-α-D-glucopyranose | Generator | a-D-Glucosamine 6-(dihydrogen phosphate) | Generator | a-D-Glucosamine 6-(dihydrogen phosphoric acid) | Generator | alpha-D-Glucosamine 6-(dihydrogen phosphoric acid) | Generator | Α-D-glucosamine 6-(dihydrogen phosphate) | Generator | Α-D-glucosamine 6-(dihydrogen phosphoric acid) | Generator | Glucosamine 6-phosphoric acid | Generator | 2-Amino-2-deoxy-D-glucose 6-phosphate | HMDB | 2-Amino-2-deoxyglucose 6-phosphate | HMDB | 2-Amino-D-glucose-6-phosphate | HMDB | D-Glucosamine 6-phosphate | HMDB | D-Glucosamine phosphate | HMDB | D-Glucosamine-6-phosphate | HMDB | Glucosamine 6 -phosphate | HMDB | Glucosamine-6-p | HMDB | Glucosamine-6-phosphate | HMDB | Glucose-6-phosphorate | HMDB | Glucose-6-phosphoric acid | HMDB | Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester | HMDB | GLCN-6-p | HMDB |
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Chemical Formula | C6H14NO8P |
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Average Mass | 259.1510 Da |
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Monoisotopic Mass | 259.04570 Da |
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IUPAC Name | {[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid |
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Traditional Name | α-D-glucosamine 6-phosphate |
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CAS Registry Number | 3616-42-0 |
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SMILES | N[C@H]1[C@@H](O)O[C@H](COP(O)(O)=O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C6H14NO8P/c7-3-5(9)4(8)2(15-6(3)10)1-14-16(11,12)13/h2-6,8-10H,1,7H2,(H2,11,12,13)/t2-,3-,4-,5-,6+/m1/s1 |
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InChI Key | XHMJOUIAFHJHBW-UKFBFLRUSA-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
- Amino saccharide
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Oxane
- Phosphoric acid ester
- Alkyl phosphate
- Hemiacetal
- 1,2-diol
- Secondary alcohol
- 1,2-aminoalcohol
- Organoheterocyclic compound
- Oxacycle
- Polyol
- Hydrocarbon derivative
- Organonitrogen compound
- Organopnictogen compound
- Primary aliphatic amine
- Organic nitrogen compound
- Organic oxide
- Amine
- Primary amine
- Alcohol
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | - 2-amino-2-deoxy-D-glucopyranose 6-phosphate (CHEBI:15873 )
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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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General References | - Wu G, Haynes TE, Yan W, Meininger CJ: Presence of glutamine:fructose-6-phosphate amidotransferase for glucosamine-6-phosphate synthesis in endothelial cells: effects of hyperglycaemia and glutamine. Diabetologia. 2001 Feb;44(2):196-202. [PubMed:11270676 ]
- Broschat KO, Gorka C, Page JD, Martin-Berger CL, Davies MS, Huang Hc HC, Gulve EA, Salsgiver WJ, Kasten TP: Kinetic characterization of human glutamine-fructose-6-phosphate amidotransferase I: potent feedback inhibition by glucosamine 6-phosphate. J Biol Chem. 2002 Apr 26;277(17):14764-70. Epub 2002 Feb 12. [PubMed:11842094 ]
- Furchak JR, Yang P, Jennings C, Walter NG, Kennedy RT: Assay for glucosamine 6-phosphate using a ligand-activated ribozyme with fluorescence resonance energy transfer or CE-laser-induced fluorescence detection. Anal Chem. 2008 Nov 1;80(21):8195-201. doi: 10.1021/ac801410k. Epub 2008 Oct 9. [PubMed:18842060 ]
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