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Bovine Metabolome Database



Showing metabocard for Cellobiose (BMDB00055)

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Version 1.0
Creation Date 2005-11-16 15:48:42
Update Date 2009-05-05 20:57:39
Accession Number BMDB00055
Common Name Cellobiose
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).
Synonyms
  1. 4-(b-D-Glucosido)-D-glucose
  2. 4-(beta-D-Glucosido)-D-glucose
  3. 4-Beta-D-Glucopyranosyl-D-glucopyranose
  4. 4-O-b-D-Glucopyranosyl-D-glucose
  5. 4-O-beta-D-Glucopyranosyl-D-glucose
  6. Cellobiose
  7. Cellose
  8. D-(+)-Cellobiose
  9. D-Cellobiose
  10. D-Glucosyl-b-(1->4)-D-glucose
  11. D-Glucosyl-beta-(1-4)-D-glucose
  12. 4-(b-delta-Glucosido)-delta-glucose
  13. 4-(beta-delta-Glucosido)-delta-glucose
  14. 4-Beta-delta-Glucopyranosyl-delta-glucopyranose
  15. 4-O-beta-delta-Glucopyranosyl-delta-glucose
  16. delta-(+)-Cellobiose
  17. delta-Cellobiose
  18. delta-Glucosyl-beta-(1->4)-delta-glucose
  19. delta-Glucosyl-beta-(1-4)-delta-glucose
  20. D-Glucosyl-beta-(1->4)-D-glucose
Chemical IUPAC Name 6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-oxane-2,3,4-triol
Chemical Formula C12H22O11
Chemical Structure Structure
Chemical Taxonomy
Kingdom
  • Organic
Super Class
  • Carbohydrates and Carbohydrate conjugates
Class
  • Carbohydrates
Sub Class
  • Disaccharides
Family
  • Microbial_Metabolite
Species
  • hemiacetal; acetal; primary alcohol; secondary alcohol; 1,2-diol; heterocyclic compound
Biofunction
Application
Source
  • Exogenous
Average Molecular Weight 342.297
Monoisotopic Molecular Weight 342.116211
Isomeric SMILES OC[C@H]1O[C@@H](O[C@@H]2[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@@H](O)[C@@H]1O
Canonical SMILES OCC1OC(OC2C(CO)OC(O)C(O)C2O)C(O)C(O)C1O
KEGG Compound ID C00185 Link Image
BioCyc ID CPD-1161 Link Image
BiGG ID Not Available
Wikipedia Link Cellobiose Link Image
METLIN ID 3480 Link Image
PubChem Compound 439178 Link Image
PubChem Substance 3485 Link Image
ChEBI ID 17057 Link Image
CAS Registry Number 528-50-7
InChI Identifier InChI=1/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
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
Melting Point (Experimental) 229-230 oC
Experimental Water Solubility 111.0 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)] Source: PhysProp
Predicted Water Solubility 586.0 mg/mL [Predicted by ALOGPS] Calculated using ALOGPS
Physiological Charge 0
State Solid
Experimental LogP/Hydrophobicity Not Available Source: PhysProp
Predicted LogP/Hydrophobicity -3.01 [Predicted by ALOGPS]; -4.3 [Predicted by PubChem via XLOGP] Calculated using ALOGPS
Material Safety Data Sheet (MSDS)
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2D Structure
3D Structure
Experimental PDB ID 1G0C Link Image
Experimental PDB File Show
Experimental PDB Structure
Experimental 1H NMR Spectrum Download Spectrum
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Experimental 13C NMR Spectrum Not Available
Experimental 13C HSQC Spectrum Download Spectrum
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Predicted 1H NMR Spectrum Show Image
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Predicted 13C NMR Spectrum Show Image
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Mass Spectrum
Low Energy
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Medium Energy
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High Energy
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Simplified TOCSY Spectrum Show Image
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BMRB Spectrum Show Image
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Cellular Location
  • Cytoplasm
Biofluid Location Not Available
Tissue Location
Tissue References
Intestine
Spleen
Concentrations (Normal) Not Available
Concentrations (Abnormal) Not Available
Pathway Names
  • Starch and Sucrose Metabolism
HMDB Pathways
Name Starch and Sucrose Metabolism
Image Show Link Image
KEGG Pathways
Name Starch and Sucrose Metabolism
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SimCell Pathways
Name Starch and Sucrose Metabolism
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Graph
SBML
General References
  1. Wikipedia Link Image