Livestock Metabolome Database: Showing metabocard for Cellobiose (LMDB00023)

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-07-13 19:40:41 UTC

Update Date

2016-07-20 20:54:28 UTC

Lmdb

LMDB00023

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Cellobiose

Description

Cellobiose, 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

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
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	HMDB
4-O-beta-D-Glucopyranosyl-D-glucopyranose	HMDB
b-Cellobiose	HMDB
Β-cellobiose	HMDB
CELLOBIOSE	ChEBI

Chemical Formula

C₁₂H₂₂O₁₁

Average Molecular Weight

342.2965

Monoisotopic Molecular Weight

342.116211546

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 Name

β-cellobiose

CAS Registry Number

528-50-7

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 Key

GUBGYTABKSRVRQ-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

O-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 Framework

Aliphatic heteromonocyclic compounds

External Descriptors

cellobiose (CHEBI:36217 )

Ontology

Status

Detected but not Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	-3	ALOGPS
logP	-4.7	ChemAxon
logS	0.23	ALOGPS
pKa (Strongest Acidic)	11.25	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	189.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	68.34 m³·mol⁻¹	ChemAxon
Polarizability	31.08 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)	splash10-0wmi-1794000000-0677096b4c9ccf48f063	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 8 TMS)	splash10-0uxr-1793000000-4b9e3693e06370d25b79	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (8 TMS)	splash10-0udi-0592000000-fd6c9b6fc37768f90f50	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxs-0951000000-5a3ac52d468ddc5c332a	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0uxr-0951000000-c862eeafae784cc54fa3	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-03e9-4897000000-332d470623cd7f1e1ced	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (4 TMS) - 70eV, Positive	splash10-014i-3222149000-51b76bf2eab425e81425	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_3_16) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_10) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_11) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_12) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_20) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_32) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_4_33) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS ("Cellobiose,3TBDMS,#3" TMS) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_5) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_6) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_7) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-03di-0901000000-4f5e21e94576c46b5a30	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9300000000-e62e4ba03fc46e7f06bc	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-000i-9000000000-ca047c1ce7b82c7aa87c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-c4ddbfcb86ed7714925b	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0fki-9600000000-684f3e6bfcb4b3f65879	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-2900000000-6f8ce9de315ceb48511c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-3900000000-a7560da5d35c827f8b96	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0fki-9600000000-555afe933920df7d007f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Negative	splash10-0uki-9600000000-deabb4159817d4b7a024	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Negative	splash10-0ik9-3900000000-b9ab5098e40517a0129c	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-516fe731f3fd059e37ab	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Negative	splash10-0ab9-9000000000-7fe640a698bed4f9e4c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-01tc-0419000000-7756e1f28bcc76e75af1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-03fr-1915000000-f7a01cbe1a1eba1f39b1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01we-4920000000-0dcd848ee51f4218f67a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-2379000000-abb41b2f1a43083992ca	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0200-3923000000-87a71f93194716a7f75d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004l-6900000000-a0954b0f7ffc379d1dee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0109000000-9d0f9a68a67bafd734ab	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01rw-3898000000-7f495a1bcfdbed6466c4	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-01ti-9210000000-b8a83657f0266d372bee	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000x-1069000000-9cd867711bca0eecf935	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9365000000-65403961bfb5e35eaa0d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-000l-9200000000-0de9785c1c5df1430dd2	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Ruminal Fluid

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Ruminal Fluid	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details

External Links

DrugBank ID

Not Available

HMDB ID

HMDB0000055

FooDB ID

FDB007497

Phenol Explorer ID

Not Available

KNApSAcK ID

C00001134

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

3480

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

ECMDB ID

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

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. [18752931 ]

Showing metabocard for Cellobiose (LMDB00023)

Structure for LMDB00023 (Cellobiose)