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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 | 2020-02-26 21:21:50 UTC |
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HMDB ID | HMDB0000055 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Cellobiose |
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Description | Cellobiose, also known as GLCB1-4GLCB or cellose, belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. Cellobiose is an extremely weak basic (essentially neutral) compound (based on its pKa). Cellobiose exists in all living species, ranging from bacteria to humans. Outside of the human body, cellobiose has been detected, but not quantified in, several different foods, such as okra, common chokecherries, other bread, cherry tomato, and welsh onions. This could make cellobiose a potential biomarker for the consumption of these foods. Cellobiose can be used as an indicator carbohydrate for Crohn's disease and malabsorption syndrome. It can be hydrolyzed to glucose enzymatically or with acid. Cellobiose is a disaccharide with the formula C12H22O11. Cellobiose has eight free alcohol (OH) groups, one acetal linkage and one hemiacetal linkage, which give rise to strong inter- and intramolecular hydrogen bonds. Cellobiose, a reducing sugar, consists of two β-glucose molecules linked by a β(1→4) bond. It can be obtained by enzymatic or acidic hydrolysis of cellulose and cellulose rich materials such as cotton, jute, or paper. Treatment of cellulose with acetic anhydride and sulfuric acid, gives cellobiose octoacetate, which is no longer a hydrogen bond donor (though it is still a hydrogen bond acceptor) and is soluble in nonpolar organic solvents. |
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Structure | |
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Synonyms | Value | Source |
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1-beta-D-Glucopyranosyl-4-beta-D-glucopyranose | ChEBI | 4-O-beta-D-Glucopyranosyl-beta-D-glucopyranose | ChEBI | beta-D-GLC-(1->4)-beta-D-GLC | ChEBI | beta-D-GLCP-(1->4)-beta-D-GLCP | ChEBI | beta-D-Glucosyl-(1->4)-beta-D-glucose | ChEBI | GLCB1-4GLCB | ChEBI | Glcbeta1-4glcbeta | ChEBI | 1-b-D-Glucopyranosyl-4-b-D-glucopyranose | Generator | 1-Β-D-glucopyranosyl-4-β-D-glucopyranose | Generator | 4-O-b-D-Glucopyranosyl-b-D-glucopyranose | Generator | 4-O-Β-D-glucopyranosyl-β-D-glucopyranose | Generator | b-D-GLC-(1->4)-b-D-GLC | Generator | Β-D-GLC-(1->4)-β-D-GLC | Generator | b-D-GLCP-(1->4)-b-D-GLCP | Generator | Β-D-GLCP-(1->4)-β-D-GLCP | Generator | b-D-Glucosyl-(1->4)-b-D-glucose | Generator | Β-D-glucosyl-(1->4)-β-D-glucose | Generator | 4-(b-D-Glucosido)-D-glucose | HMDB | 4-(b-delta-Glucosido)-delta-glucose | HMDB | 4-(beta-D-Glucosido)-D-glucose | HMDB | 4-(beta-delta-Glucosido)-delta-glucose | HMDB | 4-beta-D-Glucopyranosyl-D-glucopyranose | HMDB | 4-beta-delta-Glucopyranosyl-delta-glucopyranose | HMDB | 4-O-b-D-Glucopyranosyl-D-glucose | HMDB | 4-O-beta-D-Glucopyranosyl-D-glucose | HMDB | 4-O-beta-delta-Glucopyranosyl-delta-glucose | HMDB | Cellose | HMDB | D-(+)-Cellobiose | HMDB | D-Cellobiose | HMDB | D-Glucosyl-b-(1->4)-D-glucose | HMDB | D-Glucosyl-beta-(1-4)-D-glucose | HMDB | D-Glucosyl-beta-(1->4)-D-glucose | HMDB | delta-(+)-Cellobiose | HMDB | delta-Cellobiose | HMDB | delta-Glucosyl-beta-(1-4)-delta-glucose | HMDB | delta-Glucosyl-beta-(1->4)-delta-glucose | HMDB | 4 O beta D Glucopyranosyl D glucopyranose | HMDB | 4-O-beta-D-Glucopyranosyl-D-glucopyranose | HMDB | b-Cellobiose | HMDB | Β-cellobiose | HMDB | CELLOBIOSE | ChEBI |
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Chemical Formula | C12H22O11 |
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Average Molecular Weight | 342.2965 |
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Monoisotopic Molecular Weight | 342.116211546 |
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IUPAC Name | (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-{[(2R,3S,4R,5R,6R)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxy}oxane-3,4,5-triol |
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Traditional Name | β-cellobiose |
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CAS Registry Number | 528-50-7 |
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SMILES | OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O |
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InChI Identifier | InChI=1S/C12H22O11/c13-1-3-5(15)6(16)9(19)12(22-3)23-10-4(2-14)21-11(20)8(18)7(10)17/h3-20H,1-2H2/t3-,4-,5-,6+,7-,8-,9-,10-,11-,12+/m1/s1 |
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InChI Key | GUBGYTABKSRVRQ-QRZGKKJRSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as o-glycosyl compounds. These are glycoside in which a sugar group is bonded through one carbon to another group via a O-glycosidic bond. |
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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 | O-glycosyl compounds |
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Alternative Parents | |
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Substituents | - O-glycosyl compound
- Disaccharide
- Oxane
- Secondary alcohol
- Hemiacetal
- Oxacycle
- Organoheterocyclic compound
- Polyol
- Acetal
- 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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Physical Properties |
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State | Solid |
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Experimental Properties | Property | Value | Reference |
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Melting Point | 229 - 230 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 111 mg/mL at 15 °C | Not Available | LogP | Not Available | Not Available |
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Predicted Properties | |
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Spectra |
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| Spectrum Type | Description | Splash Key | View |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 8 TMS) | splash10-0wmi-1794000000-0677096b4c9ccf48f063 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 8 TMS) | splash10-0uxr-1793000000-4b9e3693e06370d25b79 | Spectrum | GC-MS | GC-MS Spectrum - GC-MS (8 TMS) | splash10-0udi-0592000000-fd6c9b6fc37768f90f50 | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0uxs-0951000000-5a3ac52d468ddc5c332a | Spectrum | GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0uxr-0951000000-c862eeafae784cc54fa3 | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03e9-4897000000-332d470623cd7f1e1ced | Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-014i-3222149000-51b76bf2eab425e81425 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-0901000000-4f5e21e94576c46b5a30 | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-9300000000-e62e4ba03fc46e7f06bc | Spectrum | LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9000000000-ca047c1ce7b82c7aa87c | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01tc-0419000000-7756e1f28bcc76e75af1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03fr-1915000000-f7a01cbe1a1eba1f39b1 | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01we-4920000000-0dcd848ee51f4218f67a | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-2379000000-abb41b2f1a43083992ca | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0200-3923000000-87a71f93194716a7f75d | Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004l-6900000000-a0954b0f7ffc379d1dee | Spectrum | 1D NMR | 1H NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,1H] 2D NMR Spectrum | Not Available | Spectrum | 2D NMR | [1H,13C] 2D NMR Spectrum | Not Available | Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | |
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Pathways | |
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Normal Concentrations |
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Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Normal | | details |
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Abnormal Concentrations |
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Urine | Detected but not Quantified | Not Quantified | Adult (>18 years old) | Both | Bladder cancer | | details |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | Not Available |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | FDB007497 |
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KNApSAcK ID | C00001134 |
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Chemspider ID | 10261 |
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KEGG Compound ID | C06422 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Cellobiose |
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METLIN ID | 3480 |
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PubChem Compound | 10712 |
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PDB ID | Not Available |
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ChEBI ID | 36217 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | |
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References |
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Synthesis Reference | Machida, Makoto; Hosokawa, Koji. Enzymic preparation of cellooligosaccharide with cellulase. Jpn. Kokai Tokkyo Koho (2006), 20pp. CODEN: JKXXAF JP 2006204294 A 20060810 CAN 145:187210 AN 2006:786561 |
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Material Safety Data Sheet (MSDS) | Download (PDF) |
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General References | - Matsuura Y: Degradation of konjac glucomannan by enzymes in human feces and formation of short-chain fatty acids by intestinal anaerobic bacteria. J Nutr Sci Vitaminol (Tokyo). 1998 Jun;44(3):423-36. [PubMed:9742462 ]
- Nakamura S, Oku T, Ichinose M: Bioavailability of cellobiose by tolerance test and breath hydrogen excretion in humans. Nutrition. 2004 Nov-Dec;20(11-12):979-83. [PubMed:15561487 ]
- Cain WJ, Millar JS, Himebauch AS, Tietge UJ, Maugeais C, Usher D, Rader DJ: Lipoprotein [a] is cleared from the plasma primarily by the liver in a process mediated by apolipoprotein [a]. J Lipid Res. 2005 Dec;46(12):2681-91. Epub 2005 Sep 8. [PubMed:16150825 ]
- Cobden I, Hamilton I, Rothwell J, Axon AT: Cellobiose/mannitol test: physiological properties of probe molecules and influence of extraneous factors. Clin Chim Acta. 1985 May 15;148(1):53-62. [PubMed:3924445 ]
- Welcker K, Martin A, Kolle P, Siebeck M, Gross M: Increased intestinal permeability in patients with inflammatory bowel disease. Eur J Med Res. 2004 Oct 29;9(10):456-60. [PubMed:15546811 ]
- Calero M, Ghiso J: Radiolabeling of amyloid-beta peptides. Methods Mol Biol. 2005;299:325-48. [PubMed:15980615 ]
- Sakamoto M, Huang Y, Umeda M, Ishikawa I, Benno Y: Prevotella multiformis sp. nov., isolated from human subgingival plaque. Int J Syst Evol Microbiol. 2005 Mar;55(Pt 2):815-9. [PubMed:15774668 ]
- Hu WL, Chindemi PA, Regoeczi E: In vivo behaviour of rat transferrin bearing a hybrid glycan and its interaction with macrophages. Biochem Cell Biol. 1992 Aug;70(8):636-42. [PubMed:1476702 ]
- Potier M, Dallaire L, Melancon SB: Occurrence and properties of fetal intestinal glycosidases (disaccharidases) in human amniotic fluid. Biol Neonate. 1975;27(3-4):141-52. [PubMed:241430 ]
- Johansson AG, Sundqvist T, Skogh T: IgG immune complex binding to and activation of liver cells. An in vitro study with IgG immune complexes, Kupffer cells, sinusoidal endothelial cells and hepatocytes. Int Arch Allergy Immunol. 2000 Apr;121(4):329-36. [PubMed:10828724 ]
- Kaczmarczyk A, Blom AM, Alston-Smith J, Sjoquist M, Fries E: Plasma bikunin: half-life and tissue uptake. Mol Cell Biochem. 2005 Mar;271(1-2):61-7. [PubMed:15881656 ]
- Garcia-Martos P, Garcia-Agudo L, Ruiz-Aragon J, Saldarreaga A, Marin P: [Carbohydrate assimilation by clinical and environmental Rhodotorula glutinis strains]. Rev Iberoam Micol. 2004 Jun;21(2):90-2. [PubMed:15538836 ]
- Juby LD, Rothwell J, Axon AT: Cellobiose/mannitol sugar test--a sensitive tubeless test for coeliac disease: results on 1010 unselected patients. Gut. 1989 Apr;30(4):476-80. [PubMed:2497056 ]
- Morita T, Ozawa M, Ito H, Kimio S, Kiriyama S: Cellobiose is extensively digested in the small intestine by beta-galactosidase in rats. Nutrition. 2008 Nov-Dec;24(11-12):1199-204. doi: 10.1016/j.nut.2008.06.029. Epub 2008 Aug 26. [PubMed:18752931 ]
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