Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:57:58 -0600 |
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Update Date | 2015-06-03 15:54:20 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | 2-Deoxyglucose |
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Description | 2-Deoxyglucose is a glucose molecule that has the 2-hydroxyl group replaced by hydrogen, so that it cannot undergo further glycolysis. It can be used as a glycolysis inhibitor. 2-deoxyglucose is taken up by E. coli and is phosphorylated to 2-deoxyglucose-6P. Glucosamine, mannose and 2-deoxyglucose enter Escherichia coli by the component of the phosphotransferase system coded for by the gene ptsM. 2-Deoxyglucose is an unnatural glucose analog and is not considered a natural E. coli substrate or metabolite. 2-Deoxyglucose is a relatively rare yet natural monosaccharide that can be made from D-glucose, D-aminoglucose and a variety of amino-polysaccharides. |
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Structure | |
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Synonyms: | - 2-Deoxy-D-arabino-hexopyranose
- 2-Deoxy-D-arabino-hexose
- 2-Deoxy-D-arabinohexose
- 2-Deoxy-D-glucose
- 2-Deoxy-D-mannose
- 2-deoxyglucose
- 2-Deoxyhexose
- 2-Desoxy-D-glucose
- D-2-Deoxyglucose
- D-2dGlc
- D-Arabino-2-Deoxyhexose
- D-Arabino-Hexose, 2-deoxy- ( )
- Deoxyglucose
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Chemical Formula: | C6H12O5 |
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Weight: | Average: 164.1565 Monoisotopic: 164.068473494 |
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InChI Key: | VRYALKFFQXWPIH-PBXRRBTRSA-N |
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InChI: | InChI=1S/C6H12O5/c7-2-1-4(9)6(11)5(10)3-8/h2,4-6,8-11H,1,3H2/t4-,5-,6+/m1/s1 |
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CAS number: | 154-17-6 |
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IUPAC Name: | (3R,4S,5R)-3,4,5,6-tetrahydroxyhexanal |
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Traditional IUPAC Name: | deoxyglucose |
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SMILES: | [H]C([H])(C=O)[C@@]([H])(O)[C@]([H])(O)[C@]([H])(O)CO |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as fatty alcohols. These are aliphatic alcohols consisting of a chain of a least six carbon atoms. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Fatty Acyls |
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Sub Class | Fatty alcohols |
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Direct Parent | Fatty alcohols |
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Alternative Parents | |
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Substituents | - Fatty alcohol
- Medium-chain aldehyde
- Beta-hydroxy aldehyde
- Alpha-hydrogen aldehyde
- Secondary alcohol
- Polyol
- Organic oxygen compound
- Organic oxide
- Hydrocarbon derivative
- Primary alcohol
- Organooxygen compound
- Carbonyl group
- Aldehyde
- Alcohol
- Aliphatic acyclic compound
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Molecular Framework | Aliphatic acyclic compounds |
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External Descriptors | Not Available |
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Physical Properties |
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State: | Solid |
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Charge: | 0 |
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Melting point: | 146.5 °C |
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Experimental Properties: | |
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Predicted Properties | |
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Biological Properties |
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Cellular Locations: | Cytoplasm |
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Reactions: | |
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SMPDB Pathways: | |
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KEGG Pathways: | Not Available |
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EcoCyc Pathways: | Not Available |
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Concentrations |
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| Not Available |
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Spectra |
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Spectra: | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 4 TMS) | splash10-0q29-1951000000-06cc16a9680628545167 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 4 TMS) | splash10-0lkc-0951000000-39e56efe41d6473040e4 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0fr5-0920000000-5f7dfef22a1b59cae284 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0ktb-0920000000-6f9638179f688d51022e | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0ir0-9400000000-0d9dd630f3590782a74e | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-054t-9258700000-0738ee18a80ba8e5b90a | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | View in JSpectraViewer |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-014j-3900000000-45865b9816a45604d811 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-01ow-9200000000-7b5a5cbd361ec11efbbf | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0707-9000000000-c9e6d3430eb1073f0d79 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0w29-5900000000-90300437f9ab1170e562 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0k96-9400000000-a11cb0518964ee7a83dd | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-b4574a9d519fced6b332 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-004i-6900000000-319e473c192f4b110b8d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0006-9000000000-d161d9b754ebaeb29a74 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0006-9000000000-0a62c56f2a4845f4d597 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-08ml-9700000000-9df4724be189ef01f655 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0abc-9000000000-e85603d6bed71b3882e0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0006-9000000000-4ed5058ebfd661cb8c61 | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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1D NMR | 13C NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882
- van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
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Synthesis Reference: | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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Links |
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External Links: | |
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