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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 | 2020-07-17 20:52:09 UTC |
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HMDB ID | HMDB0001254 |
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Secondary Accession Numbers | |
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Metabolite 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. 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 | |
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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 | Glucosamine 6-phosphoric acid | 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 | 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 | MeSH, HMDB |
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Chemical Formula | C6H14NO8P |
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Average Molecular Weight | 259.151 |
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Monoisotopic Molecular Weight | 259.045702941 |
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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 | 55722-81-1 |
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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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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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Ontology |
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Disposition | Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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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 | splash10-052b-9320000000-54466a568e39d51598c7 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0ik9-3912400000-c198d10e982d681785ed | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0970000000-095ba413dfd29c80b445 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-053r-9500000000-e4e82ba86236d6046d0d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001i-9000000000-bd232a0933f76298e943 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-03di-0190000000-778d1a36aaf5c9b3c846 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-08i0-1690000000-f08f9e49e698f1aa134d | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-002b-9010000000-8a6a96ec67621a842ce8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002b-9010000000-8a6a96ec67621a842ce8 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0190000000-280711606909adbb8814 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-08i0-1690000000-f08f9e49e698f1aa134d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0490000000-818ec0fe39e531f561a4 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dj-9850000000-40bb2cfef099c426fcbf | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0kmj-9500000000-9bb59bf1855e5fa76305 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0699-8950000000-68f380f4fab22160c728 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9110000000-4f7a2c18e5b29f9e6076 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-6fc65d9a14f58d847a4f | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 1D NMR | 13C NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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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 | DB02657 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB022515 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 388356 |
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KEGG Compound ID | C00352 |
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BioCyc ID | D-GLUCOSAMINE-6-P |
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BiGG ID | 34709 |
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Wikipedia Link | Not Available |
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METLIN ID | 6111 |
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PubChem Compound | 439217 |
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PDB ID | Not Available |
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ChEBI ID | 15873 |
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Food Biomarker Ontology | Not Available |
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VMH ID | GAM6P |
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MarkerDB ID | |
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References |
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Synthesis Reference | Cacioppo, F.; Pandolfo, L.; Arena, E. Synthesis of glucosamine 6-phosphate in tissues of rachitic rats. Giorn. Biochim. (1964), 13(4), 249-55. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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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 ]
- Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]
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