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Showing metabocard for Cellobiose (HMDB0000055)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
enzymes (3) Show 3 proteins
Record Information
Version4.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:21:50 UTC
HMDB IDHMDB0000055
Secondary Accession Numbers
  • HMDB00055
Metabolite Identification
Common NameCellobiose
DescriptionCellobiose, 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.
Structure
Data?1582752109
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-beta-D-Glucopyranosyl-4-beta-D-glucopyranoseChEBI
4-O-beta-D-Glucopyranosyl-beta-D-glucopyranoseChEBI
beta-D-GLC-(1->4)-beta-D-GLCChEBI
beta-D-GLCP-(1->4)-beta-D-GLCPChEBI
beta-D-Glucosyl-(1->4)-beta-D-glucoseChEBI
GLCB1-4GLCBChEBI
Glcbeta1-4glcbetaChEBI
1-b-D-Glucopyranosyl-4-b-D-glucopyranoseGenerator
1-Β-D-glucopyranosyl-4-β-D-glucopyranoseGenerator
4-O-b-D-Glucopyranosyl-b-D-glucopyranoseGenerator
4-O-Β-D-glucopyranosyl-β-D-glucopyranoseGenerator
b-D-GLC-(1->4)-b-D-GLCGenerator
Β-D-GLC-(1->4)-β-D-GLCGenerator
b-D-GLCP-(1->4)-b-D-GLCPGenerator
Β-D-GLCP-(1->4)-β-D-GLCPGenerator
b-D-Glucosyl-(1->4)-b-D-glucoseGenerator
Β-D-glucosyl-(1->4)-β-D-glucoseGenerator
4-(b-D-Glucosido)-D-glucoseHMDB
4-(b-delta-Glucosido)-delta-glucoseHMDB
4-(beta-D-Glucosido)-D-glucoseHMDB
4-(beta-delta-Glucosido)-delta-glucoseHMDB
4-beta-D-Glucopyranosyl-D-glucopyranoseHMDB
4-beta-delta-Glucopyranosyl-delta-glucopyranoseHMDB
4-O-b-D-Glucopyranosyl-D-glucoseHMDB
4-O-beta-D-Glucopyranosyl-D-glucoseHMDB
4-O-beta-delta-Glucopyranosyl-delta-glucoseHMDB
CelloseHMDB
D-(+)-CellobioseHMDB
D-CellobioseHMDB
D-Glucosyl-b-(1->4)-D-glucoseHMDB
D-Glucosyl-beta-(1-4)-D-glucoseHMDB
D-Glucosyl-beta-(1->4)-D-glucoseHMDB
delta-(+)-CellobioseHMDB
delta-CellobioseHMDB
delta-Glucosyl-beta-(1-4)-delta-glucoseHMDB
delta-Glucosyl-beta-(1->4)-delta-glucoseHMDB
4 O beta D Glucopyranosyl D glucopyranoseHMDB
4-O-beta-D-Glucopyranosyl-D-glucopyranoseHMDB
b-CellobioseHMDB
Β-cellobioseHMDB
CELLOBIOSEChEBI
Chemical FormulaC12H22O11
Average Molecular Weight342.2965
Monoisotopic Molecular Weight342.116211546
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 Nameβ-cellobiose
CAS Registry Number528-50-7
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
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
InChI KeyGUBGYTABKSRVRQ-QRZGKKJRSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentO-glycosyl compounds
Alternative Parents
Substituents
  • O-glycosyl compound
  • Disaccharide
  • Oxane
  • Secondary alcohol
  • Hemiacetal
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Alcohol
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point229 - 230 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility111 mg/mL at 15 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility586 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity68.34 m³·mol⁻¹ChemAxon
Polarizability31.08 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-0wmi-1794000000-0677096b4c9ccf48f063Spectrum
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)splash10-0uxr-1793000000-4b9e3693e06370d25b79Spectrum
GC-MSGC-MS Spectrum - GC-MS (8 TMS)splash10-0udi-0592000000-fd6c9b6fc37768f90f50Spectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxs-0951000000-5a3ac52d468ddc5c332aSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0uxr-0951000000-c862eeafae784cc54fa3Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03e9-4897000000-332d470623cd7f1e1cedSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positivesplash10-014i-3222149000-51b76bf2eab425e81425Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-03di-0901000000-4f5e21e94576c46b5a30Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-000i-9300000000-e62e4ba03fc46e7f06bcSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-000i-9000000000-ca047c1ce7b82c7aa87cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01tc-0419000000-7756e1f28bcc76e75af1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03fr-1915000000-f7a01cbe1a1eba1f39b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01we-4920000000-0dcd848ee51f4218f67aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-2379000000-abb41b2f1a43083992caSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0200-3923000000-87a71f93194716a7f75dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-6900000000-a0954b0f7ffc379d1deeSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Urine
Tissue Locations
  • Intestine
  • Spleen
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)BothNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected but not Quantified Adult (>18 years old)Both
Bladder cancer		 details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB007497
KNApSAcK IDC00001134
Chemspider ID10261
KEGG Compound IDC06422
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCellobiose
METLIN ID3480
PubChem Compound10712
PDB IDNot Available
ChEBI ID36217
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceMachida, 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)
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. Calero M, Ghiso J: Radiolabeling of amyloid-beta peptides. Methods Mol Biol. 2005;299:325-48. [PubMed:15980615 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]

Enzymes

Enzyme Details
1. Glucosidase 2 subunit beta
General function:
Involved in calcium ion binding
Specific function:
Regulatory subunit of glucosidase II
Gene Name:
PRKCSH
Uniprot ID:
P14314
Molecular weight:
59424.9
References
  1. 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 ]
Enzyme Details
2. Glucosylceramidase
General function:
Involved in catalytic activity
Specific function:
Not Available
Gene Name:
GBA
Uniprot ID:
P04062
Molecular weight:
59715.745
Enzyme Details
3. Cytosolic beta-glucosidase
General function:
Involved in hydrolase activity, hydrolyzing O-glycosyl compounds
Specific function:
Glycosidase probably involved in the intestinal absorption and metabolism of dietary flavonoid glycosides. Able to hydrolyze a broad variety of glycosides including phytoestrogens, flavonols, flavones, flavanones and cyanogens. Possesses beta-glycosylceramidase activity and may be involved in a nonlysosomal catabolic pathway of glycosylceramide.
Gene Name:
GBA3
Uniprot ID:
Q9H227
Molecular weight:
Not Available
Reactions
Cellobiose + Water → D-Glucosedetails
References
  1. 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 ]