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| Identification |
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| YMDB ID | YMDB00044 |
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| Name | Glucosamine 6-phosphate |
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| Species | Saccharomyces cerevisiae |
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| Strain | Baker's yeast |
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| Description | Glucosamine 6-phosphate, also known as glucose-6-phosphoric acid or GLCN-6-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. Glucosamine 6-phosphate is a very strong basic compound (based on its pKa). Glucosamine 6-phosphate exists in all living species, ranging from bacteria to humans. |
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| Structure | |
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| Synonyms | - 2-amino-2-Deoxy-6-O-phosphono-a-D-glucopyranose
- 2-amino-2-Deoxy-6-O-phosphono-alpha-D-glucopyranose
- 2-amino-2-Deoxy-6-O-phosphono-α-D-glucopyranose
- 2-Amino-2-deoxy-D-glucose 6-phosphate
- 2-Amino-2-deoxyglucose 6-phosphate
- 2-Amino-D-glucose-6-phosphate
- a-D-Glucosamine 6-(dihydrogen phosphate)
- a-D-Glucosamine 6-(dihydrogen phosphoric acid)
- alpha-D-Glucosamine 6-(dihydrogen phosphate)
- alpha-D-Glucosamine 6-(dihydrogen phosphoric acid)
- D-Glucosamine 6-phosphate
- D-Glucosamine phosphate
- D-Glucosamine-6-phosphate
- GLCN-6-P
- Glucosamine 6 -phosphate
- Glucosamine 6-Phosphate
- Glucosamine 6-phosphate, disodium salt
- Glucosamine 6-phosphate, monosodium salt
- Glucosamine 6-phosphic acid
- Glucosamine 6-phosphoric acid
- glucosamine-6-P
- glucosamine-6-phosphate
- Glucose-6-phosphorate
- Glucose-6-phosphoric acid
- Phosphoric acid mono-((2R,3S,4R,5R)-5-amino-2,3,4-trihydroxy-6-oxo-hexyl) ester
- α-D-glucosamine 6-(dihydrogen phosphate)
- α-D-glucosamine 6-(dihydrogen phosphoric acid)
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| CAS number | 3616-42-0 |
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| Weight | Average: 259.151
Monoisotopic: 259.045702941 |
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| InChI Key | XHMJOUIAFHJHBW-UKFBFLRUSA-N |
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| InChI | 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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| IUPAC Name | {[(2R,3S,4R,5R,6S)-5-amino-3,4,6-trihydroxyoxan-2-yl]methoxy}phosphonic acid |
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| Traditional IUPAC Name | α-D-glucosamine 6-phosphate |
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| Chemical Formula | C6H14NO8P |
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| SMILES | [H]O[C@@]1([H])O[C@]([H])(C([H])([H])OP(=O)(O[H])O[H])[C@@]([H])(O[H])[C@]([H])(O[H])[C@@]1([H])N([H])[H] |
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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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| Charge | 0 |
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| Melting point | Not Available |
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| Experimental Properties | | Property | Value | Reference |
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| Water Solubility | Not Available | PhysProp | | LogP | Not Available | PhysProp |
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| Predicted Properties | |
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| Biological Properties |
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| Cellular Locations | |
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| Organoleptic Properties | Not Available |
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| SMPDB Pathways | | Amino sugar and nucleotide sugar metabolism | PW002413 |    |
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| KEGG Pathways | | Alanine, aspartate and glutamate metabolism | ec00250 |  | | Amino sugar and nucleotide sugar metabolism | ec00520 |  |
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| SMPDB Reactions | |
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| KEGG Reactions | |
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| Concentrations |
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| Intracellular Concentrations | Not Available |
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| Extracellular Concentrations | Not Available |
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| Spectra |
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| Spectra | | 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 | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive | splash10-0ik9-3912400000-c198d10e982d681785ed | JSpectraViewer | | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | JSpectraViewer | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-004i-0970000000-095ba413dfd29c80b445 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-053r-9500000000-e4e82ba86236d6046d0d | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-001i-9000000000-bd232a0933f76298e943 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positive | splash10-03di-0190000000-778d1a36aaf5c9b3c846 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, Positive | splash10-08i0-1690000000-f08f9e49e698f1aa134d | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative | splash10-002b-9010000000-8a6a96ec67621a842ce8 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , negative | splash10-002b-9010000000-8a6a96ec67621a842ce8 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-03di-0190000000-280711606909adbb8814 | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - LC-ESI-QTOF , positive | splash10-08i0-1690000000-f08f9e49e698f1aa134d | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-03di-3190000000-0f9d6942fba86f12422e | JSpectraViewer | MoNA | | LC-MS/MS | LC-MS/MS Spectrum - 30V, Positive | splash10-03fr-2790000000-7fe42a3d5900a5984d04 | JSpectraViewer | MoNA | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-03di-0490000000-818ec0fe39e531f561a4 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dj-9850000000-40bb2cfef099c426fcbf | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0kmj-9500000000-9bb59bf1855e5fa76305 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0699-8950000000-68f380f4fab22160c728 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004i-9110000000-4f7a2c18e5b29f9e6076 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-6fc65d9a14f58d847a4f | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-0006-0790000000-d9873144345380710376 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-006x-9810000000-32a2cffa4a376910fdb3 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01ot-9000000000-7be390edddedcba28a23 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-054k-9040000000-fd7b28df2dbc578cfc0b | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-004j-9010000000-f0f082b70bb688bd4b38 | JSpectraViewer | | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004i-9000000000-a5e502a2627af2048a1f | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 1H NMR Spectrum | Not Available | JSpectraViewer | | 1D NMR | 13C NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | JSpectraViewer | | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | JSpectraViewer |
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| References |
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| References: | - UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
- Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
- Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
- Dummitt, B., Micka, W. S., Chang, Y. H. (2005). "Yeast glutamine-fructose-6-phosphate aminotransferase (Gfa1) requires methionine aminopeptidase activity for proper function." J Biol Chem 280:14356-14360.15699032
- Mio, T., Yamada-Okabe, T., Arisawa, M., Yamada-Okabe, H. (1999). "Saccharomyces cerevisiae GNA1, an essential gene encoding a novel acetyltransferase involved in UDP-N-acetylglucosamine synthesis." J Biol Chem 274:424-429.9867860
- Watzele, G., Tanner, W. (1989). "Cloning of the glutamine:fructose-6-phosphate amidotransferase gene from yeast. Pheromonal regulation of its transcription." J Biol Chem 264:8753-8758.2656689
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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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| External Links: | |
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