Record Information |
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Version | 4.0 |
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Status | Expected but not Quantified |
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Creation Date | 2005-11-16 15:48:42 UTC |
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Update Date | 2017-12-07 01:06:11 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 is a disaccharide consisting of two glucose units in a beta (1-4) glycosidic linkage. Obtained from the partial hydrolysis of cellulose, cellobiose is commonly used as an indicator carbohydrate for intestinal permeability in Crohn's disease and malabsorption syndrome. This carbohydrate is exogenous and is a microbial breakdown product from plant material (cellulose). It is not produced by the body nor is it readily metabolized by the body, but may be found in some food products (vegetables, fruits, corn syrups, etc.). Recent studies have shown that cellobiose can be processed or metabolized by endogenous beta glycosidases in the mammalian small intestine (PMID 18752931 ). |
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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 | MeSH | 4-O-beta-D-Glucopyranosyl-D-glucopyranose | MeSH |
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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 | This compound 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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Spectra | Spectrum Type | Description | Splash Key | |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 8 TMS) | splash10-0wmi-1794000000-0677096b4c9ccf48f063 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (1 MEOX; 8 TMS) | splash10-0uxr-1793000000-4b9e3693e06370d25b79 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-MS (8 TMS) | splash10-0udi-0592000000-fd6c9b6fc37768f90f50 | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0uxs-0951000000-5a3ac52d468ddc5c332a | View in MoNA |
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GC-MS | GC-MS Spectrum - GC-EI-TOF (Non-derivatized) | splash10-0uxr-0951000000-c862eeafae784cc54fa3 | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-03e9-4897000000-332d470623cd7f1e1ced | View in MoNA |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive | splash10-014i-3222149000-51b76bf2eab425e81425 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated) | splash10-03di-0901000000-4f5e21e94576c46b5a30 | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated) | splash10-000i-9300000000-e62e4ba03fc46e7f06bc | View in MoNA |
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LC-MS/MS | LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated) | splash10-000i-9000000000-ca047c1ce7b82c7aa87c | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-01tc-0419000000-7756e1f28bcc76e75af1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-03fr-1915000000-f7a01cbe1a1eba1f39b1 | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-01we-4920000000-0dcd848ee51f4218f67a | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0006-2379000000-abb41b2f1a43083992ca | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0200-3923000000-87a71f93194716a7f75d | View in MoNA |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-004l-6900000000-a0954b0f7ffc379d1dee | View in MoNA |
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1D NMR | 1H NMR Spectrum | Not Available | View in JSpectraViewer |
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2D NMR | [1H,1H] 2D 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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General References | - 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 ]
- 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 ]
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