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Record Information
Version1.0
Creation Date2016-07-13 19:40:41 UTC
Update Date2016-07-20 20:54:28 UTC
LmdbLMDB00023
Secondary Accession NumbersNone
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 also a microbe metabolite. 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 biscuits, nectarines, jutes, pepper (c. baccatum), and rosemaries. This could make cellobiose a potential biomarker for the consumption of these foods. This carbohydrate is exogenous and is a microbial breakdown product from plant material (cellulose). It may be found in some food products (vegetables, fruits, corn syrups, etc.). It is a microbial breakdown product from plant material (cellulose). 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. 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 ).
Structure
Thumb
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
StatusDetected but not Quantified
OriginNot Available
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
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
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_3_16) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_10) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_11) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_12) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_20) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Cellobiose,3TBDMS,#3" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, PositiveNot AvailableSpectrum
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
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-c4ddbfcb86ed7714925bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0fki-9600000000-684f3e6bfcb4b3f65879Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-2900000000-6f8ce9de315ceb48511cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-3900000000-a7560da5d35c827f8b96Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0fki-9600000000-555afe933920df7d007fSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Negativesplash10-0uki-9600000000-deabb4159817d4b7a024Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-3900000000-b9ab5098e40517a0129cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-516fe731f3fd059e37abSpectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-9000000000-7fe640a698bed4f9e4c6Spectrum
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0109000000-9d0f9a68a67bafd734abSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01rw-3898000000-7f495a1bcfdbed6466c4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-01ti-9210000000-b8a83657f0266d372beeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000x-1069000000-9cd867711bca0eecf935Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9365000000-65403961bfb5e35eaa0dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-000l-9200000000-0de9785c1c5df1430dd2Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
2D NMR[1H,1H] 2D NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular LocationsNot Available
Biofluid Locations and Tissue Locations
  • Ruminal Fluid
Concentrations
BiofluidStatusValueConditionSpeciesReferenceDetails
Ruminal FluidDetected but not QuantifiedNot ApplicableNot AvailableBovine details
DrugBank IDNot Available
HMDB IDHMDB0000055
FooDB IDFDB007497
Phenol Explorer IDNot Available
KNApSAcK IDC00001134
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID3480
PDB IDNot Available
Wikipedia LinkCellobiose
Chemspider ID10261
ChEBI ID36217
PubChem Compound ID10712
Kegg Compound IDC06422
YMDB IDYMDB00869
ECMDB IDECMDB00055
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General 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. [18752931 ]