Record Information |
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Version | 2.0 |
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Creation Date | 2012-05-31 13:58:38 -0600 |
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Update Date | 2015-09-13 12:56:12 -0600 |
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Secondary Accession Numbers | |
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Identification |
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Name: | alpha-D-Glucose |
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Description | Alpha-D-Glucose is a primary source of energy for living organisms. It is naturally occurring and is found in fruits and other parts of plants in its free state. Alpha-D-Glucose is an intermediate in glycolysis/gluconeogenesis pathway where it is converted to beta-D-glucose via galactose-1-epimerase (mutarotase) (EC:5.1.3.3). It is also involved in several other metabolic pathways: fructose and mannose metabolism, galactose metabolism, starch and sucrose metabolism and amino sugar and nucleotide sugar metabolism. |
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Structure | |
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Synonyms: | - α-glucose
- 6-(Hydroxymethyl)tetrahydropyran-2,3,4,5-tetraol
- A-D-Glucopyranose
- A-D-Glucose
- a-delta-Glucopyranose
- a-delta-Glucose
- A-Dextrose
- A-Glucose
- a-δ-Glucopyranose
- a-δ-Glucose
- Alpha-D-Glucopyranose
- Alpha-D-Glucose
- Alpha-delta-Glucopyranose
- Alpha-delta-Glucose
- Alpha-Dextrose
- Alpha-Glucose
- D-glucose
- Glucose
- Hexopyranose
- α-D-Glucopyranose
- α-D-Glucose
- α-Dextrose
- α-Glucose
- α-δ-Glucopyranose
- α-δ-Glucose
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Chemical Formula: | C6H12O6 |
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Weight: | Average: 180.1559 Monoisotopic: 180.063388116 |
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InChI Key: | WQZGKKKJIJFFOK-DVKNGEFBSA-N |
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InChI: | InChI=1S/C6H12O6/c7-1-2-3(8)4(9)5(10)6(11)12-2/h2-11H,1H2/t2-,3-,4+,5-,6+/m1/s1 |
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CAS number: | 492-62-6 |
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IUPAC Name: | (2S,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol |
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Traditional IUPAC Name: | α-glucose |
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SMILES: | OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@@H]1O |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hexoses. These are monosaccharides in which the sugar unit is a is a six-carbon containing moeity. |
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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 | Hexoses |
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Alternative Parents | |
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Substituents | - Hexose monosaccharide
- Oxane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Hydrocarbon derivative
- Primary alcohol
- Alcohol
- 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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Charge: | 0 |
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Melting point: | 146 °C |
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Experimental Properties: | Property | Value | Source |
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Water Solubility: | 500 mg/mL at 20 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] | PhysProp |
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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: | Amino sugar and nucleotide sugar metabolism II | PW000887 | | Amino sugar and nucleotide sugar metabolism III | PW000895 | | Galactose metabolism | PW000821 | | Secondary metabolites: Trehalose Biosynthesis and Metabolism | PW000968 | | Starch and sucrose metabolism | PW000941 | | galactose degradation/Leloir Pathway | PW000884 | |
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KEGG Pathways: | - Amino sugar and nucleotide sugar metabolism ec00520
- Fructose and mannose metabolism ec00051
- Galactose metabolism ec00052
- Glycolysis / Gluconeogenesis ec00010
- Metabolic pathways eco01100
- Microbial metabolism in diverse environments ec01120
- Starch and sucrose metabolism ec00500
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EcoCyc Pathways: | |
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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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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0np0-9700000000-e8d638dc817e46b97d7b | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positive | splash10-004i-6122690000-eaf6f7adf34ccd0c667b | 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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LC-MS/MS | LC-MS/MS Spectrum - 10V, Negative | splash10-0a4i-9100000000-57ee067515dbaeec1e27 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0ab9-9100000000-311a61760b7c0dc3a7e1 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0ab9-9100000000-f2beec08615d57ac1a02 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 35V, Negative | splash10-0ab9-9100000000-eb694004566014e0b267 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 20V, Negative | splash10-0a4i-9000000000-906b2fd231873b000e08 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - 40V, Negative | splash10-0a4i-9000000000-3cd19dc7a445df26b86d | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-9100000000-53278ff57ca00e1b5d1a | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-0079-9000000000-c4182c64988208ac78b0 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-2900000000-a4ec4f0b1e29e360a952 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-01t9-6900000000-7b3ea9c64ecc8d4ac867 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-052f-9100000000-ec2bf4918640a0a36398 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-004i-2900000000-2448926b508622464fe7 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-056r-8900000000-4c073cb93b78120113e6 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0a4l-9000000000-ece70093ab5d3c331ac4 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01q9-0900000000-b0bc47623e7b2ca31c02 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03ea-3900000000-648e1637af29cf2a3518 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0007-9200000000-9e6f46a1cbf52d6e347a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01qa-0900000000-04ceb34d441ff6a75763 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03dl-9400000000-a8f1ceab155611f949c1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01ow-9000000000-358f68fc2b7a72c27546 | View in MoNA |
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1D NMR | 1H 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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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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2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | View in JSpectraViewer |
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References |
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References: | - Dalmau SR, Freitas CS: Sugar inhibition of the lectin jacalin: comparison of three assays. Braz J Med Biol Res. 1989;22(5):601-10. Pubmed: 2620170
- Georgiou S, Pasmatzi E, Monastirli A, Sakkis T, Alachioti S, Tsambaos D: Age-related alterations in the carbohydrate residue composition of the cell surface in the unexposed normal human epidermis. Gerontology. 2005 May-Jun;51(3):155-60. Pubmed: 15832040
- Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510
- 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
- Onyshchenko AM, Korobkova KS, Kovalenko NK, Kasumova SO, Skrypal' IH: [The role of the carbohydrate composition of the glycocalyx in some species of lactobacilli in the manifestation of their adhesive properties] Mikrobiol Z. 1999 Nov-Dec;61(6):22-8. Pubmed: 10733280
- Skrypal' IH, Tokovenko IP, Malynovs'ka LP: [Carbohydrate receptors for Mycoplasma fermentans adhesion on human epithelial tissues] Mikrobiol Z. 1995 Jul-Aug;57(4):17-22. Pubmed: 8548067
- Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
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Synthesis Reference: | Simmons, Blake A.; Volponi, Joanne V.; Ingersoll, David; Walker, Andrew. Conversion of sucrose to b-D-glucose using three-stage immobilized enzyme process. U.S. (2007), 12pp. |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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Links |
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External Links: | |
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