Page last updated: 2024-12-05

cellobiose

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Cellobiose is a disaccharide composed of two glucose molecules linked by a β(1→4) glycosidic bond. It is a major component of cellulose, a structural polysaccharide found in plants. Cellobiose is not found free in nature but can be produced by the enzymatic hydrolysis of cellulose. It is a white crystalline solid that is soluble in water. Cellobiose is not as sweet as glucose. Cellobiose is used in various applications, including as a food additive, a sweetener, and a building block for other biopolymers. It is also studied for its potential use in biofuel production. It is studied because it is a major product of cellulose breakdown and a potential substrate for biofuel production. It is also an important intermediate in the biosynthesis of cellulose.'

beta-cellobiose : A cellobiose with beta configuration at the reducing-end glucose residue. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID10712
CHEMBL ID1231670
CHEBI ID36217
SCHEMBL ID21348
MeSH IDM0003775

Synonyms (68)

Synonym
CHEBI:36217 ,
beta-d-glc-(1->4)-beta-d-glc
glcb1-4glcb
beta-d-glcp-(1->4)-beta-d-glcp
glcbeta1-4glcbeta
d-glucopyranose, 4-o-beta-d-glucopyranosyl-
einecs 208-436-5
unii-bm3mox055h
CHEMBL1231670
13360-52-6
d-(+)-cellobiose
4-beta-d-glucopyranosyl-d-glucopyranose
d-cellobiose
4-(beta-d-glucosido)-d-glucose
d-glucosyl-beta-(1-4)-d-glucose
cellose
d-glucose, 4-o-.beta.-d-glucopyranosyl-
beta-d-glc-(1-4)-d-glc
4-o-beta-d-glucopyranosyl-d-glucose
d-glucose, 4-o-beta-d-glucopyranosyl- (6ci,9ci)
6-(hydroxymethyl)-5-[3,4,5-trihydroxy-6-(hydroxymethyl) tetrahydropyran-2-yl]oxy-tetrahydropyran-2,3,4-triol
cellobiose (8ci)
beta-d-glucopyranose, 4-o-beta-d-glucopyranosyl-
ai3-18877
beta-cellobiose
CELLOBIOSE ,
4-o-beta-d-glucopyranosyl-beta-d-glucopyranose
C06422
1-beta-d-glucopyranosyl-4-beta-d-glucopyranose
beta-d-cellobiose
528-50-7
beta-d-glucosyl-(1->4)-beta-d-glucose
1Z3T
1QI0
NCGC00095661-01
75E7DA6F-2B17-4FB0-A5D1-65DB9CE697EF
2RFY
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-[(2r,3s,4r,5r,6r)-4,5,6-trihydroxy-2-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
d-glucose, 4-o-beta-d-glucopyranosyl-
dsstox_rid_81272
cas-528-50-7
dsstox_gsid_45984
tox21_111512
dsstox_cid_25984
d(+)-cellobiose
AM83979
SCHEMBL21348
AKOS024462559
mfcd00136034
(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
beta-d-glucopyranosyl-(1->4)-beta-d-glucopyranose
delta-glucosyl-beta-(1->4)-delta-glucose
4-(b-d-glucosido)-d-glucose
d-glucosyl-b-(1->4)-d-glucose
4-(beta-delta-glucosido)-delta-glucose
delta-cellobiose
delta-(+)-cellobiose
4-(b-delta-glucosido)-delta-glucose
4-beta-delta-glucopyranosyl-delta-glucopyranose
4-o-beta-delta-glucopyranosyl-delta-glucose
d-glucosyl-beta-(1->4)-d-glucose
delta-glucosyl-beta-(1-4)-delta-glucose
4-o-b-d-glucopyranosyl-d-glucose
DTXSID00873933
GEO-04676
Q27104340
AS-11681
nsc 2559

Research Excerpts

Overview

Cellobiose is a disaccharide with potential prebiotic effects, as demonstrated in different animal species, but not yet in horses. Cellobiose utilization is a variable trait that is often used to differentiate members of the family Vibrionaceae.

ExcerptReferenceRelevance
"Cellobiose is a naturally occurring only slightly sweet disaccharide that may be used as a novel food ingredient. "( Genotoxic potential of cellobiose.
Bär, A; Messinger, H; Winkler, A, 2020
)
2.31
"Cellobiose is a disaccharide with potential prebiotic effects, as demonstrated in different animal species, but not yet in horses. "( Impact of Dietary Cellobiose on the Fecal Microbiota of Horses.
Paßlack, N; Vahjen, W; Zentek, J, 2020
)
2.33
"Cellobiose is a major intermediate from cellulase hydrolysis of pretreated plant biomass. "( Improved cellobiose utilization in E. coli by including both hydrolysis and phosphorolysis mechanisms.
Chen, R; Rutter, C, 2014
)
2.26
"Cellobiose is a glucose dimer connected by a glycosidic bond and represents the simplest model molecule for cellulose."( One-step conversion of cellobiose to C6-alcohols using a ruthenium nanocluster catalyst.
Dyson, PJ; Kou, Y; Liu, H; Luo, C; Yan, N; Zhao, C, 2006
)
1.37
"Cellobiose utilization is a variable trait that is often used to differentiate members of the family Vibrionaceae. "( Identification of a cellobiose utilization gene cluster with cryptic beta-galactosidase activity in Vibrio fischeri.
Adin, DM; Stabb, EV; Visick, KL, 2008
)
2.11
"The cellobiose/mannitol test is a good indicator of severe mucosal damage; it does not discriminate subjects with minor degrees of mucosal abnormalities, but may give useful indications on the functional state of the jejunal mucosa."( Cellobiose/mannitol sugar permeability test in children in relation to jejunal morphometry.
Abete, A; Cucciardi, M; Greco, L; Mayer, M; Mugione, P; Troncone, R, 1995
)
2.21

Effects

ExcerptReferenceRelevance
"Cellobiose has a beta-1,4 linkage, so it is resistant to hydrolysis by human small intestinal disaccharidase and, hence, reaches the colon undigested."( Bioavailability of cellobiose by tolerance test and breath hydrogen excretion in humans.
Ichinose, M; Nakamura, S; Oku, T,
)
1.18
"Cellobiose has a beta-1,4 linkage, so it is resistant to hydrolysis by human small intestinal disaccharidase and, hence, reaches the colon undigested."( Bioavailability of cellobiose by tolerance test and breath hydrogen excretion in humans.
Ichinose, M; Nakamura, S; Oku, T,
)
1.18

Actions

Cellobiose appeared to inhibit the rCelS activity through a competitive mechanism. Cellobiose did not inhibit glucose uptake in either yeast.

ExcerptReferenceRelevance
"Cellobiose appeared to inhibit the rCelS activity through a competitive mechanism."( Product inhibition of the recombinant CelS, an exoglucanase component of the Clostridium thermocellum cellulosome.
Andreacchi, A; Kruus, K; Wang, WK; Wu, JH, 1995
)
1.01
"Cellobiose did not inhibit glucose uptake in either yeast."( Transport of glucose and cellobiose by Candida wickerhamii and Clavispora lusitaniae.
Freer, SN; Greene, RV, 1990
)
1.3

Bioavailability

The bioavailability of cellobiose (CEB) was investigated with respect to small intestinal digestibility and cecal fermentation in rats. As predicted, theBioavailability of paracellular probes declined with increasing molecular mass (rhamnose, 62+/-4%) and was significantly higher in bats than has been reported for rats.

ExcerptReferenceRelevance
" The absorption rate (clearance) of CcpLEamide was comparable with that of CcpLE in the presence of these peptidase inhibitors."( Intestinal absorption and analgesic activity of aminopeptidase-resistant cellobiose-coupled leucine enkephalinamide.
Awazu, S; Mizuma, T; Ohta, K, 1998
)
0.53
" We measured the bioavailability and rates of absorption of two metabolically inert carbohydrates not transported by mediated pathways (L-rhamnose and cellobiose, molecular masses of 164 and 342, respectively) to measure paracellular uptake, and of a non-metabolized D-glucose analog (3-O-methyl-D-glucose) to measure total uptake by both mediated and paracellular pathways."( Paracellular nutrient absorption in a gum-feeding new world primate, the common marmoset Callithrix jacchus.
Karasov, WH; McWhorter, TJ, 2007
)
0.54
" As predicted, the bioavailability of paracellular probes declined with increasing molecular mass (rhamnose, 62+/-4%; cellobiose, 22+/-4%) and was significantly higher in bats than has been reported for rats and other mammals."( Absorption of sugars in the Egyptian fruit bat (Rousettus aegyptiacus): a paradox explained.
Karasov, WH; Korine, C; McWhorter, TJ; Pinshow, B; Tracy, CR; Wojciechowski, MS, 2007
)
0.55
"The bioavailability of cellobiose (CEB) was investigated with respect to small intestinal digestibility and cecal fermentation in rats."( Cellobiose is extensively digested in the small intestine by beta-galactosidase in rats.
Ito, H; Kimio, S; Kiriyama, S; Morita, T; Ozawa, M,
)
1.88
"Microbial biofilms in rivers contribute to the decomposition of the available organic matter which typically shows changes in composition and bioavailability due to their origin, seasonality, and watershed characteristics."( Labile and recalcitrant organic matter utilization by river biofilm under increasing water temperature.
Romaní, AM; Sabater, S; Ylla, I, 2012
)
0.38
"In this study, the effect of D-cellobiose on oral bioavailability of gentiopicroside (GPS) was investigate."( [Effect of D-cellobiose on oral bioavailability of gentiopicroside].
Dai, YH; Ju, JM; Wang, LL; Wang, M; Zhang, ZH; Zhu, YN, 2016
)
1.09
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51

Dosage Studied

ExcerptRelevanceReference
" One method to decrease the enzyme dosage and increase biocatalytic productivity is to re-use β-glucosidase (BG) via immobilization."( Enzymatic cellulose hydrolysis: enzyme reusability and visualization of β-glucosidase immobilized in calcium alginate.
Meyer, AS; Tsai, CT, 2014
)
0.4
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
epitopeThe biological role played by a material entity when bound by a receptor of the adaptive immune system. Specific site on an antigen to which an antibody binds.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
cellobioseA glycosylglucose consisting of two glucose units linked via a beta(1->4) bond.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (4)

PathwayProteinsCompounds
starch degradation II610
cellulose degradation II (fungi)95
superpathway of cellulose and hemicellulose degradation (cellulolosome)08
Biochemical pathways: part I0466

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
AR proteinHomo sapiens (human)Potency10.68220.000221.22318,912.5098AID743036
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Endoglucanase BSalipaludibacillus agaradhaerensKi4,500.00004,500.00004,500.00004,500.0000AID977610
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, cellulasePhanerodontia chrysosporiumKd115.000077.000096.0000115.0000AID977611
Chain A, cellulasePhanerodontia chrysosporiumKd115.000077.000096.0000115.0000AID977611
Chain A, Cellulose 1,4-beta-cellobiosidaseMelanocarpus albomycesKd6.00006.00006.00006.0000AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1811Experimentally measured binding affinity data derived from PDB2005The FEBS journal, Apr, Volume: 272, Issue:8
Structures of Phanerochaete chrysosporium Cel7D in complex with product and inhibitors.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2005The FEBS journal, Apr, Volume: 272, Issue:8
Structures of Phanerochaete chrysosporium Cel7D in complex with product and inhibitors.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2008Protein science : a publication of the Protein Society, Aug, Volume: 17, Issue:8
Crystal structures of Melanocarpus albomyces cellobiohydrolase Cel7B in complex with cello-oligomers show high flexibility in the substrate binding.
AID1811Experimentally measured binding affinity data derived from PDB2000Journal of molecular biology, Mar-31, Volume: 297, Issue:3
Insights into ligand-induced conformational change in Cel5A from Bacillus agaradhaerens revealed by a catalytically active crystal form.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2000Journal of molecular biology, Mar-31, Volume: 297, Issue:3
Insights into ligand-induced conformational change in Cel5A from Bacillus agaradhaerens revealed by a catalytically active crystal form.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,349)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990163 (12.08)18.7374
1990's223 (16.53)18.2507
2000's293 (21.72)29.6817
2010's549 (40.70)24.3611
2020's121 (8.97)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 67.79

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be very strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index67.79 (24.57)
Research Supply Index7.24 (2.92)
Research Growth Index4.82 (4.65)
Search Engine Demand Index118.59 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (67.79)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials2 (0.14%)5.53%
Reviews15 (1.08%)6.00%
Case Studies1 (0.07%)4.05%
Observational0 (0.00%)0.25%
Other1,375 (98.71%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]