Cellobiose (YMDB00869)

Identification

YMDB ID

YMDB00869

Name

Cellobiose

Species

Saccharomyces cerevisiae

Strain

Baker's yeast

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 an extremely weak basic (essentially neutral) compound (based on its pKa). Cellobiose exists in all living species, ranging from bacteria to humans.

Structure

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

Synonyms

4-(b-D-Glucosido)-D-glucose
4-(b-delta-Glucosido)-delta-glucose
4-(beta-D-Glucosido)-D-glucose
4-(beta-delta-Glucosido)-delta-glucose
4-Beta-D-Glucopyranosyl-D-glucopyranose
4-Beta-delta-Glucopyranosyl-delta-glucopyranose
4-O-b-D-Glucopyranosyl-D-glucose
4-O-beta-D-Glucopyranosyl-D-glucose
4-O-beta-delta-Glucopyranosyl-delta-glucose
Cellobiose
Cellose
D-(+)-Cellobiose
D-Cellobiose
D-Glucosyl-b-(1->4)-D-glucose
D-Glucosyl-beta-(1->4)-D-glucose
D-Glucosyl-beta-(1-4)-D-glucose
delta-(+)-Cellobiose
delta-Cellobiose
delta-Glucosyl-beta-(1->4)-delta-glucose
delta-Glucosyl-beta-(1-4)-delta-glucose
1-beta-D-Glucopyranosyl-4-beta-D-glucopyranose
4-O-beta-D-Glucopyranosyl-beta-D-glucopyranose
beta-D-GLC-(1->4)-beta-D-GLC
beta-D-GLCP-(1->4)-beta-D-GLCP
beta-D-Glucosyl-(1->4)-beta-D-glucose
GLCB1-4GLCB
Glcbeta1-4glcbeta
1-b-D-Glucopyranosyl-4-b-D-glucopyranose
1-Β-D-glucopyranosyl-4-β-D-glucopyranose
4-O-b-D-Glucopyranosyl-b-D-glucopyranose
4-O-Β-D-glucopyranosyl-β-D-glucopyranose
b-D-GLC-(1->4)-b-D-GLC
Β-D-GLC-(1->4)-β-D-GLC
b-D-GLCP-(1->4)-b-D-GLCP
Β-D-GLCP-(1->4)-β-D-GLCP
b-D-Glucosyl-(1->4)-b-D-glucose
Β-D-glucosyl-(1->4)-β-D-glucose
4 O beta D Glucopyranosyl D glucopyranose
4-O-beta-D-Glucopyranosyl-D-glucopyranose
b-Cellobiose
Β-cellobiose

CAS number

528-50-7

Weight

Average: 342.2965
Monoisotopic: 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

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

Chemical Formula

C₁₂H₂₂O₁₁

SMILES

[H]OC([H])([H])[C@@]1([H])O[C@@]([H])(O[C@@]2([H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]([H])(O[H])O[C@]2([H])C([H])([H])O[H])[C@]([H])(O[H])[C@@]([H])(O[H])[C@]1([H])O[H]

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 )

Physical Properties

State

Solid

Charge

Melting point

229-230 °C

Experimental Properties

Property	Value	Reference
Water Solubility	111 mg/mL at 15 oC [YALKOWSKY,SH & DANNENFELSER,RM (1992)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	586 g/L	ALOGPS
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	0	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Not Available

SMPDB Pathways

Starch and sucrose metabolism

PW002481

KEGG Pathways

Starch and sucrose metabolism

ec00500

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

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

References

References:

Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828

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

External Links:

Resource	Link
CHEBI ID	17057
HMDB ID	HMDB00055
Pubchem Compound ID	439178
Kegg ID	C00185
ChemSpider ID	23327704
FOODB ID	FDB007497
Wikipedia	Cellobiose
BioCyc ID	CPD-1161

Structure for #<Compound:0xb67e5264>