Record Information |
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Version | 1.0 |
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Created at | 2006-08-12 22:03:45 UTC |
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Updated at | 2021-06-29 00:47:49 UTC |
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NP-MRD ID | NP0000652 |
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Secondary Accession Numbers | None |
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Natural Product Identification |
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Common Name | Beta-D-Glucose 6-phosphate |
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Description | Beta-D-Glucose 6 phosphate (b-G6P) is the beta-anomer of glucose-6-phosphate. There are two anomers of glucose 6 phosphate: The alpha anomer and the beta anomer. Specifically, beta-D-Glucose 6-phosphate is glucose sugar phosphorylated on carbon 6. It is a very common metabolite in cells as the vast majority of glucose entering a cell will become phosphorylated in this way. The primary reason for the immediate phosphorylation of glucose is to prevent diffusion out of the cell. The phosphorylation adds a charged phosphate group so the glucose 6-phosphate cannot easily cross the cell membrane. B-G6P is involved in glycolysis, gluconeogenesis, pentose phosphate, and glycogen and sucrose metabolic pathways. Beta-D-Glucose 6 phosphate can be generated through beta-D-fructose phosphate or alpha-D-glucose 6 phosphate (via glucose-6-phosphate isomerase) or beta-D glucose (via hexokinase). It can then be sent off to the pentose phosphate pathway which generates the useful cofactor NADPH as well as ribulose 5-phosphate, a carbon source for the synthesis of other molecules. Alternately, if the cell needs energy or carbon skeletons for synthesis then glucose 6-phosphate is targeted for glycolysis. A third route is to have glucose 6 phosphate stored or converted into glycogen, especially if blood glucose levels are high. |
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Structure | O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1 |
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Synonyms | Value | Source |
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6-H2PO3glcbeta | ChEBI | 6-O-Phosphono-beta-D-glucopyranose | ChEBI | beta-D-Glucose 6-(dihydrogen phosphate) | ChEBI | beta-D-Glucose 6-phosphic acid | ChEBI | BETA-D-GLUCOSE-6-phosphATE | ChEBI | 6-O-Phosphono-b-D-glucopyranose | Generator | 6-O-Phosphono-β-D-glucopyranose | Generator | b-D-Glucose 6-(dihydrogen phosphate) | Generator | b-D-Glucose 6-(dihydrogen phosphoric acid) | Generator | beta-D-Glucose 6-(dihydrogen phosphoric acid) | Generator | Β-D-glucose 6-(dihydrogen phosphate) | Generator | Β-D-glucose 6-(dihydrogen phosphoric acid) | Generator | b-D-Glucose 6-phosphate | Generator | b-D-Glucose 6-phosphoric acid | Generator | beta-D-Glucose 6-phosphoric acid | Generator | Β-D-glucose 6-phosphate | Generator | Β-D-glucose 6-phosphoric acid | Generator | b-D-GLUCOSE-6-phosphate | Generator | b-D-GLUCOSE-6-phosphoric acid | Generator | beta-D-GLUCOSE-6-phosphoric acid | Generator | Β-D-glucose-6-phosphate | Generator | Β-D-glucose-6-phosphoric acid | Generator |
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Chemical Formula | C6H13O9P |
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Average Mass | 260.1358 Da |
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Monoisotopic Mass | 260.02972 Da |
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IUPAC Name | {[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methoxy}phosphonic acid |
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Traditional Name | β-D-glucose 6-phosphate |
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CAS Registry Number | Not Available |
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SMILES | O[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H](O)[C@H]1O |
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InChI Identifier | InChI=1S/C6H13O9P/c7-3-2(1-14-16(11,12)13)15-6(10)5(9)4(3)8/h2-10H,1H2,(H2,11,12,13)/t2-,3-,4+,5-,6-/m1/s1 |
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InChI Key | NBSCHQHZLSJFNQ-VFUOTHLCSA-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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| Predicted Spectra |
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| Spectrum Type | Description | Depositor ID | Depositor Organization | Depositor | Deposition Date | View |
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1D NMR | 13C NMR Spectrum (1D, 25 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 252 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 50 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 75 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 101 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 126 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 151 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 176 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 201 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 226 MHz, D2O, predicted) | Wishart Lab | Wishart Lab | David Wishart | 2021-06-20 | View Spectrum |
| Chemical Shift Submissions |
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| Not Available | Species |
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Species of Origin | |
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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
- Monoalkyl phosphate
- Organic phosphoric acid derivative
- Alkyl phosphate
- Oxane
- Phosphoric acid ester
- Hemiacetal
- Secondary alcohol
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Alcohol
- Organic oxide
- Aliphatic heteromonocyclic compound
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Molecular Framework | Aliphatic heteromonocyclic compounds |
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External Descriptors | |
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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 | -3.643 | Not Available |
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Predicted Properties | |
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General References | - von Gunten S, Smith DF, Cummings RD, Riedel S, Miescher S, Schaub A, Hamilton RG, Bochner BS: Intravenous immunoglobulin contains a broad repertoire of anticarbohydrate antibodies that is not restricted to the IgG2 subclass. J Allergy Clin Immunol. 2009 Jun;123(6):1268-76.e15. doi: 10.1016/j.jaci.2009.03.013. Epub 2009 May 13. [PubMed:19443021 ]
- Jandus P, Boligan KF, Smith DF, de Graauw E, Grimbacher B, Jandus C, Abdelhafez MM, Despont A, Bovin N, Simon D, Rieben R, Simon HU, Cummings RD, von Gunten S: The architecture of the IgG anti-carbohydrate repertoire in primary antibody deficiencies. Blood. 2019 Nov 28;134(22):1941-1950. doi: 10.1182/blood.2019001705. [PubMed:31537530 ]
- Witkin JM, Ornstein PL, Mitch CH, Li R, Smith SC, Heinz BA, Wang XS, Xiang C, Carter JH, Anderson WH, Li X, Broad LM, Pasqui F, Fitzjohn SM, Sanger HE, Smith JL, Catlow J, Swanson S, Monn JA: In vitro pharmacological and rat pharmacokinetic characterization of LY3020371, a potent and selective mGlu2/3 receptor antagonist. Neuropharmacology. 2017 Mar 15;115:100-114. doi: 10.1016/j.neuropharm.2015.12.021. Epub 2015 Dec 31. [PubMed:26748052 ]
- Duan X, Zhang X, Chen J, Xiao M, Zhao W, Liu S, Sui G: Association of PM2.5 with Insulin Resistance Signaling Pathways on a Microfluidic Liver-Kidney Microphysiological System (LK-MPS) Device. Anal Chem. 2021 Jul 20;93(28):9835-9844. doi: 10.1021/acs.analchem.1c01384. Epub 2021 Jul 7. [PubMed:34232631 ]
- Nemeth Z, Kulcsar L, Flipphi M, Orosz A, Aguilar-Pontes MV, de Vries RP, Karaffa L, Fekete E: l-Arabinose induces d-galactose catabolism via the Leloir pathway in Aspergillus nidulans. Fungal Genet Biol. 2019 Feb;123:53-59. doi: 10.1016/j.fgb.2018.11.004. Epub 2018 Nov 26. [PubMed:30496805 ]
- Mercaldi GF, Dawson A, Hunter WN, Cordeiro AT: The structure of a Trypanosoma cruzi glucose-6-phosphate dehydrogenase reveals differences from the mammalian enzyme. FEBS Lett. 2016 Aug;590(16):2776-86. doi: 10.1002/1873-3468.12276. Epub 2016 Jul 19. [PubMed:27391210 ]
- Elsasser B, Dohmeier-Fischer S, Fels G: Theoretical investigation of the enzymatic phosphoryl transfer of beta-phosphoglucomutase: revisiting both steps of the catalytic cycle. J Mol Model. 2012 Jul;18(7):3169-79. doi: 10.1007/s00894-011-1344-5. Epub 2012 Jan 12. [PubMed:22238068 ]
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