Record Information
Version 1.0
Update Date 1/22/2018 12:54:53 PM
Metabolite IDPAMDB000018
Identification
Name: Cellobiose
Description:Cellobiose is a disaccharide consisting of two glucose units in a beta (1-4) glycosidic linkage. It is an intermediate of starch and sucrose metabolism. It is formed through the action of endo-1,4-D-glucanase and converted to beta-D-glucose by beta-D-glucoside glucohydrolase (EC:3.2.1.21). (KEGG)
Structure
Thumb
Synonyms:
  • 4-β-D-glucopyranosyl-D-glucopyranose
  • 4-(b-D-Glucosido)-D-glucose
  • 4-(b-delta-Glucosido)-delta-glucose
  • 4-(b-δ-glucosido)-δ-Glucose
  • 4-(beta-D-Glucosido)-D-glucose
  • 4-(beta-delta-Glucosido)-delta-glucose
  • 4-(β-D-glucosido)-D-Glucose
  • 4-(β-δ-glucosido)-δ-Glucose
  • 4-b-D-Glucopyranosyl-D-glucopyranose
  • 4-b-delta-Glucopyranosyl-delta-glucopyranose
  • 4-b-δ-Glucopyranosyl-δ-glucopyranose
  • 4-beta-D-Glucopyranosyl-D-glucopyranose
  • 4-beta-delta-Glucopyranosyl-delta-glucopyranose
  • 4-O-b-D-Glucopyranosyl-D-glucose
  • 4-O-b-delta-Glucopyranosyl-delta-glucose
  • 4-O-b-δ-Glucopyranosyl-δ-glucose
  • 4-O-beta-D-Glucopyranosyl-D-glucose
  • 4-O-beta-delta-Glucopyranosyl-delta-glucose
  • 4-O-β-D-Glucopyranosyl-D-glucose
  • 4-O-β-δ-Glucopyranosyl-δ-glucose
  • 4-β-D-Glucopyranosyl-D-glucopyranose
  • 4-β-δ-Glucopyranosyl-δ-glucopyranose
  • Cellobiose
  • Cellose
  • D-(+)-Cellobiose
  • D-Cellobiose
  • D-Glucosyl-b-(1-4)-D-glucose
  • D-Glucosyl-b-(1->4)-D-glucose
  • D-Glucosyl-beta-(1-4)-D-glucose
  • D-Glucosyl-beta-(1->4)-D-glucose
  • D-Glucosyl-β-(1-4)-D-glucose
  • D-Glucosyl-β-(1->4)-D-glucose
  • Delta-(+)-Cellobiose
  • Delta-Cellobiose
  • delta-Glucosyl-b-(1-4)-delta-glucose
  • delta-Glucosyl-b-(1->4)-delta-glucose
  • Delta-Glucosyl-beta-(1-4)-delta-glucose
  • Delta-Glucosyl-beta-(1->4)-delta-glucose
  • δ-(+)-Cellobiose
  • δ-Cellobiose
  • δ-Glucosyl-b-(1-4)-δ-glucose
  • δ-Glucosyl-b-(1->4)-δ-glucose
  • δ-Glucosyl-β-(1-4)-δ-glucose
  • δ-Glucosyl-β-(1->4)-δ-glucose
Chemical Formula: C12H22O11
Average Molecular Weight: 342.2965
Monoisotopic Molecular Weight: 342.116211546
InChI Key: GUBGYTABKSRVRQ-QRZGKKJRSA-N
InChI: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
CAS number: 528-50-7
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
Traditional IUPAC Name: β-cellobiose
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
Chemical Taxonomy
Taxonomy DescriptionThis 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.
Kingdom Organic compounds
Super ClassOrganooxygen compounds
Class Carbohydrates and carbohydrate conjugates
Sub ClassGlycosyl compounds
Direct Parent O-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Polyol
  • Hemiacetal
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular Framework Aliphatic heteromonocyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:0
Melting point: 229-230 °C
Experimental Properties:
PropertyValueSource
Water Solubility:111.0 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]PhysProp
Predicted Properties
PropertyValueSource
Water Solubility586.0 mg/mLALOGPS
logP-3ALOGPS
logP-4.7ChemAxon
logS0.23ALOGPS
pKa (Strongest Acidic)11.25ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count8ChemAxon
Polar Surface Area189.53 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m3·mol-1ChemAxon
Polarizability31.86 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-0wmi-1794000000-0677096b4c9ccf48f063View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-0uxr-1793000000-4b9e3693e06370d25b79View in MoNA
GC-MSGC-MS Spectrum - GC-MS (8 TMS)splash10-0udi-0592000000-fd6c9b6fc37768f90f50View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0901000000-4f5e21e94576c46b5a30View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9300000000-e62e4ba03fc46e7f06bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-ca047c1ce7b82c7aa87cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,1H] 2D NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
References
References:
  • 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
  • Calero M, Ghiso J: Radiolabeling of amyloid-beta peptides. Methods Mol Biol. 2005;299:325-48. Pubmed: 15980615
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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
  • 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. Epub 2008 Aug 26. Pubmed: 18752931
  • 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
  • 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
  • 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
  • van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195
  • 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
  • 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
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
Material Safety Data Sheet (MSDS) Download (PDF)
External Links:
ResourceLink
CHEBI ID17057
HMDB IDHMDB00055
Pubchem Compound ID439178
Kegg IDC00185
ChemSpider ID10261
WikipediaCellobiose
BioCyc IDCELLOBIOSE
EcoCyc IDCELLOBIOSE
Ligand ExpoCBI

Enzymes

General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Hydrolysis of terminal, non-reducing beta-D- glucosyl residues with release of beta-D-glucose
Gene Name:
bglX
Locus Tag:
PA1726
Molecular weight:
83 kDa
Reactions
Hydrolysis of terminal, non-reducing beta-D-glucosyl residues with release of beta-D-glucose.

Transporters