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Record Information |
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Version | 4.0 |
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Status | Detected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2019-01-11 19:14:39 UTC |
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HMDB ID | HMDB0000516 |
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Secondary Accession Numbers | - HMDB0003340
- HMDB00516
- HMDB03340
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Metabolite Identification |
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Common Name | Beta-D-Glucose |
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Description | Beta-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. It is used therapeutically in fluid and nutrient replacement. A glucoside is a glycoside that is derived from glucose. Glucosides are common in plants, but rare in animals. Glucose is produced when a glucoside is hydrolysed by purely chemical means, or decomposed by fermentation or enzymes. This group contains a benzene and also an ethylene group, being derived from styrolene. Coniferin, C16H22O8, occurs in the cambium of conifer wood. Emulsin converts it into glucose and coniferyl alcohol, while oxidation gives glycovanillin, which yields with emulsin glucose and vanillin. Syringin, which occurs in the bark of Syringe vulgaris, is a methoxyconiferin. Phloridzus occurs in the root-bark of various fruit trees; it hydrolyses to glucose and phloretin, which is the phloroglucin ester of paraoxyhydratropic acid. It is related to the pentosides naringin, C21HEOi1, which hydrolyses to rhamnose and naringenin, the phioroglucin ester of para-oxycinnamic acid, and hesperidin, which hydrolyses to rhamnose and hesperetin, the phloroglucin ester of meta-oxy-para-methoxycinnamic acid or isoferulic acid, C10H10O4. Classification of the glucosides is a matter of some difficulty. One based on the chemical constitution of the non-glucose part of the molecules has been proposed that frames four groups: (I) ethylene derivatives, (2) benzene derivatives, (3) styrolene derivatives, (4) anthracene derivatives. A group may also be made to include the cyanogenetic glucosides, i.e. those containing prussic acid. Other classifications follow a botanical classification, which has several advantages; in particular, plants of allied genera contain similar compounds. In this article the chemical classification will be followed, and only the more important compounds will be discussed here. |
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Structure | |
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Synonyms | Value | Source |
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Glucose | ChEMBL | b-D-Glucose | Generator | β-D-glucose | Generator | b-D-Glucopyranose | HMDB | b-Dextrose | HMDB | b-Glucose | HMDB | beta-D-Glucopyranose | HMDB | beta-delta-Glucopyranose | HMDB | beta-Dextrose | HMDB | beta-Glucose | HMDB | D Glucose | MeSH | Glucose, (beta-D)-isomer | MeSH | Dextrose | MeSH | Glucose, (L)-isomer | MeSH | Monohydrate, glucose | MeSH | Anhydrous dextrose | MeSH | Glucose, (DL)-isomer | MeSH | Glucose, (alpha-D)-isomer | MeSH | L Glucose | MeSH | D-Glucose | MeSH | Dextrose, anhydrous | MeSH | Glucose monohydrate | MeSH | L-Glucose | MeSH |
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Chemical Formula | C6H12O6 |
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Average Molecular Weight | 180.1559 |
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Monoisotopic Molecular Weight | 180.063388116 |
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IUPAC Name | (2R,3R,4S,5S,6R)-6-(hydroxymethyl)oxane-2,3,4,5-tetrol |
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Traditional Name | glucoside |
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CAS Registry Number | 492-61-5 |
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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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InChI Identifier | 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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InChI Key | WQZGKKKJIJFFOK-VFUOTHLCSA-N |
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Chemical Taxonomy |
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Description | This compound 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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Ontology |
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Disposition | Route of exposure: Source: Biological location: |
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Process | Naturally occurring process: |
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Role | Industrial application: |
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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 | -3.24 | SANGSTER (1994) |
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Predicted Properties | |
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Spectra | |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Feces | Detected but not Quantified | | Adult (>18 years old) | Male | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Female | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Normal | | details | Saliva | Detected but not Quantified | | Adult (>18 years old) | Not Specified | Normal | | details |
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Abnormal Concentrations |
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Feces | Detected but not Quantified | | Adult (>18 years old) | Male | Gout | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Female | ankylosing spondylitis | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Female | rheumatoid arthritis | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Irritable bowel syndrome | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Irritable bowel syndrome | | details | Feces | Detected but not Quantified | | Adult (>18 years old) | Both | Ulcerative colitis | | details |
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Associated Disorders and Diseases |
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Disease References | Irritable bowel syndrome |
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- Ponnusamy K, Choi JN, Kim J, Lee SY, Lee CH: Microbial community and metabolomic comparison of irritable bowel syndrome faeces. J Med Microbiol. 2011 Jun;60(Pt 6):817-27. doi: 10.1099/jmm.0.028126-0. Epub 2011 Feb 17. [PubMed:21330412 ]
- Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
| Ulcerative colitis |
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- Le Gall G, Noor SO, Ridgway K, Scovell L, Jamieson C, Johnson IT, Colquhoun IJ, Kemsley EK, Narbad A: Metabolomics of fecal extracts detects altered metabolic activity of gut microbiota in ulcerative colitis and irritable bowel syndrome. J Proteome Res. 2011 Sep 2;10(9):4208-18. doi: 10.1021/pr2003598. Epub 2011 Aug 8. [PubMed:21761941 ]
| Gout |
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- Shao T, Shao L, Li H, Xie Z, He Z, Wen C: Combined Signature of the Fecal Microbiome and Metabolome in Patients with Gout. Front Microbiol. 2017 Feb 21;8:268. doi: 10.3389/fmicb.2017.00268. eCollection 2017. [PubMed:28270806 ]
| Rheumatoid arthritis |
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- Tie-juan ShaoZhi-xing HeZhi-jun XieHai-chang LiMei-jiao WangCheng-ping Wen. Characterization of ankylosing spondylitis and rheumatoid arthritis using 1H NMR-based metabolomics of human fecal extracts. Metabolomics. April 2016, 12:70 [Link]
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Associated OMIM IDs | |
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External Links |
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DrugBank ID | DB02379 |
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Phenol Explorer Compound ID | Not Available |
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FoodDB ID | FDB011824 |
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KNApSAcK ID | Not Available |
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Chemspider ID | 58238 |
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KEGG Compound ID | C00221 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Not Available |
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METLIN ID | 3755 |
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PubChem Compound | 64689 |
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PDB ID | BGC |
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ChEBI ID | 15903 |
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References |
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Synthesis Reference | Wenck, Helmut; Kinedt, Claudia; Bader, Hans Joachim. Production of b-D-glucose. Praxis der Naturwissenschaften, Chemie (1986), 35(4), 23. |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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