Record Information |
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Version | 1.0 |
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Creation date | 2011-09-21 00:15:11 UTC |
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Update date | 2019-11-26 03:21:04 UTC |
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Primary ID | FDB022515 |
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Secondary Accession Numbers | Not Available |
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Chemical Information |
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FooDB Name | Glucosamine 6-phosphate |
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Description | Glucosamine 6-phosphate is normally produced in endothelial cells via the 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) [HMDB] |
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CAS Number | 3616-42-0 |
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Structure | |
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Synonyms | Synonym | 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 | 2-amino-2-Deoxy-6-O-ONO-a-D-glucopyranose | Generator | 2-amino-2-Deoxy-6-O-ONO-alpha-D-glucopyranose | ChEBI | 2-amino-2-Deoxy-6-O-ONO-α-D-glucopyranose | Generator | 2-amino-2-Deoxy-D-glucose 6-ate | HMDB | 2-amino-2-Deoxyglucose 6-ate | HMDB | 2-amino-D-Glucose-6-ate | HMDB | a-D-Glucosamine 6-(dihydrogen ate) | Generator | a-D-Glucosamine 6-(dihydrogen ic acid) | Generator | alpha-D-Glucosamine 6-(dihydrogen ate) | ChEBI | alpha-D-Glucosamine 6-(dihydrogen ic acid) | Generator | D-Glucosamine 6-ate | HMDB | D-Glucosamine ate | HMDB | D-Glucosamine-6-ate | HMDB | Glucosamine 6 -ate | HMDB | GLUCOSAMINE 6-ATE | ChEBI | GLUCOSAMINE 6-ic acid | Generator | Glucosamine 6-Phosphate | hmdb | Glucosamine 6-phosphic acid | hmdb | Glucosamine-6-ate | HMDB | glucosamine-6-P | hmdb | glucosamine-6-phosphate | hmdb | Glucose-6-orate | HMDB | Glucose-6-oric acid | HMDB | Oric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester | HMDB | α-D-glucosamine 6-(dihydrogen ate) | Generator | α-D-glucosamine 6-(dihydrogen ic acid) | Generator |
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Predicted Properties | |
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Chemical Formula | C6H14NO8P |
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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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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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Isomeric 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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Average Molecular Weight | 259.151 |
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Monoisotopic Molecular Weight | 259.045702941 |
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Classification |
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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 | Biological location: Source: |
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Role | Industrial application: |
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Physico-Chemical Properties - Experimental |
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Physico-Chemical Properties - Experimental | Property | Value | Reference |
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Physical state | Solid | |
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Physical Description | Not Available | |
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Mass Composition | Not Available | |
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Melting Point | Not Available | |
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Boiling Point | Not Available | |
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Experimental Water Solubility | Not Available | |
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Experimental logP | Not Available | |
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Experimental pKa | Not Available | |
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Isoelectric point | Not Available | |
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Charge | Not Available | |
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Optical Rotation | Not Available | |
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Spectroscopic UV Data | Not Available | |
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Density | Not Available | |
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Refractive Index | Not Available | |
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Spectra |
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Spectra | |
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EI-MS/GC-MS | Type | Description | Splash Key | View |
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Predicted GC-MS | Glucosamine 6-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | splash10-052b-9320000000-54466a568e39d51598c7 | Spectrum | Predicted GC-MS | Glucosamine 6-phosphate, 3 TMS, Predicted GC-MS Spectrum - 70eV, Positive | splash10-0ik9-3912400000-c198d10e982d681785ed | Spectrum | Predicted GC-MS | Glucosamine 6-phosphate, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive | Not Available | Spectrum |
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MS/MS | Type | Description | Splash Key | View |
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MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0970000000-095ba413dfd29c80b445 | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-053r-9500000000-e4e82ba86236d6046d0d | Spectrum | MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001i-9000000000-bd232a0933f76298e943 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-03di-0190000000-778d1a36aaf5c9b3c846 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-08i0-1690000000-f08f9e49e698f1aa134d | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-002b-9010000000-8a6a96ec67621a842ce8 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002b-9010000000-8a6a96ec67621a842ce8 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0190000000-280711606909adbb8814 | Spectrum | MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-08i0-1690000000-f08f9e49e698f1aa134d | Spectrum | MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-03di-3190000000-0f9d6942fba86f12422e | Spectrum | MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-03fr-2790000000-7fe42a3d5900a5984d04 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0490000000-818ec0fe39e531f561a4 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dj-9850000000-40bb2cfef099c426fcbf | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0kmj-9500000000-9bb59bf1855e5fa76305 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0699-8950000000-68f380f4fab22160c728 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9110000000-4f7a2c18e5b29f9e6076 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-6fc65d9a14f58d847a4f | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0790000000-d9873144345380710376 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-006x-9810000000-32a2cffa4a376910fdb3 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01ot-9000000000-7be390edddedcba28a23 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-054k-9040000000-fd7b28df2dbc578cfc0b | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-9010000000-f0f082b70bb688bd4b38 | Spectrum | Predicted MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-a5e502a2627af2048a1f | Spectrum |
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NMR | |
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External Links |
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ChemSpider ID | 388356 |
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ChEMBL ID | Not Available |
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KEGG Compound ID | C00352 |
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Pubchem Compound ID | 439217 |
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Pubchem Substance ID | Not Available |
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ChEBI ID | 15873 |
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Phenol-Explorer ID | Not Available |
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DrugBank ID | Not Available |
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HMDB ID | HMDB01254 |
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CRC / DFC (Dictionary of Food Compounds) ID | Not Available |
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EAFUS ID | Not Available |
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Dr. Duke ID | Not Available |
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BIGG ID | 34709 |
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KNApSAcK ID | Not Available |
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HET ID | GLP |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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Flavornet ID | Not Available |
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GoodScent ID | Not Available |
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SuperScent ID | Not Available |
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Wikipedia ID | Not Available |
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Phenol-Explorer Metabolite ID | Not Available |
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Duplicate IDS | Not Available |
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Old DFC IDS | Not Available |
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Associated Foods |
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Food | Content Range | Average | Reference |
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Food | | | Reference |
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Biological Effects and Interactions |
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Health Effects / Bioactivities | Not Available |
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Enzymes | Name | Gene Name | UniProt ID |
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Glucokinase | GCK | P35557 | Hexokinase-3 | HK3 | P52790 | Hexokinase-2 | HK2 | P52789 | Hexokinase-1 | HK1 | P19367 | Glucosamine-6-phosphate isomerase 2 | GNPDA2 | Q8TDQ7 | Putative N-acetylglucosamine-6-phosphate deacetylase | AMDHD2 | Q9Y303 | Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 2 | GFPT2 | O94808 | Glutamine--fructose-6-phosphate aminotransferase [isomerizing] 1 | GFPT1 | Q06210 | Glucosamine 6-phosphate N-acetyltransferase | GNPNAT1 | Q96EK6 |
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Pathways | |
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Metabolism | Not Available |
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Biosynthesis | Not Available |
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Organoleptic Properties |
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Flavours | Not Available |
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Files |
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MSDS | show |
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References |
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Synthesis Reference | Not Available |
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General Reference | Not Available |
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Content Reference | |
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