Page last updated: 2024-12-06

methylglucoside, (alpha-d)-isomer

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

Description

Methylglucoside is a glycosidic derivative of glucose with a methyl group attached to the anomeric carbon. It exists in two forms: α-D-methylglucoside and β-D-methylglucoside. The α-D-isomer is commonly obtained by reacting glucose with methanol in the presence of an acid catalyst. This compound has been studied for its potential applications in various fields, including the pharmaceutical industry, food science, and materials science. It exhibits a variety of biological activities, such as anti-inflammatory, antioxidant, and antitumor properties. Its ability to inhibit the growth of certain types of cancer cells has made it a subject of ongoing research for its potential therapeutic value. Methylglucoside is also known to be a potent inhibitor of α-glucosidase, an enzyme involved in the breakdown of carbohydrates. This property makes it a potential candidate for the development of drugs for treating diabetes. Additionally, methylglucoside can be used as a building block for the synthesis of other more complex molecules. Its chemical stability and versatility have led to its exploration as a potential material for use in drug delivery systems, biocompatible polymers, and biodegradable materials.'

methyl alpha-D-glucopyranoside : An alpha-D-glucopyranoside having a methyl substituent at the anomeric position. [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 CID64947
CHEMBL ID131853
CHEBI ID320061
SCHEMBL ID50473
MeSH IDM0317107

Synonyms (82)

Synonym
c7h14o6
glucopyranoside, methyl, .alpha.-d-
nsc-214092
.alpha.-methylglucoside
.alpha.-methyl d-glucose ether
methyl .alpha.-d-glucopyranoside
97-30-3
methyl .alpha.-d-glucoside
nsc-102101
.alpha.-d-glucopyranoside, methyl
methyl-alpha-d-glucopyranoside
methyl alpha-d-glucopyranoside
GYP ,
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
bdbm20876
alpha-methyl-d-glucopyranoside (amg)
[14c]alpha-methyl-d-glucopyranoside
methyl alpha-d-glucopyranoside, >=99%
1WS4
glucopyranoside, methyl, alpha-d-
alpha-d-glucopyranoside, methyl
alpha-methyl d-glucose ether
alpha-methylglucoside
methyl alpha-d-glucoside
nsc 102101
methyl alpha-d-glucoside (van)
alpha-d-glucoside, methyl
alpha-methyl-d-glucoside
ai3-18790
einecs 202-571-3
methyl glucose
1-o-methyl-alpha-d-glucopyranoside
methyl alpha-d-glucopyranose
a-methyl-d-glucoside
alphamg
BE2A51F8-C121-4E44-89AB-05A013F8AA57
1-o-methyl-alpha-d-glucopyranose
alpha-d-methyl glucoside
me alpha-glc
CHEBI:320061 ,
1-o-methyl-alpha-d-glucoside
CHEMBL131853
M0228
1-methyl-alpha-d-glucopyranoside
dtxcid806605
cas-97-30-3
dtxsid7026605 ,
tox21_200430
NCGC00257984-01
alpha-d-methylglucoside
qcf122nf3r ,
unii-qcf122nf3r
(2r,3s,4s,5r,6s)-2-(hydroxymethyl)-6-methoxytetrahydro-2h-pyran-3,4,5-triol
EPITOPE ID:150073
me-alpha-glc
AKOS015896548
alpha-mdg
gtpl4640
alpha-methyl-d-glucose pyranoside
SCHEMBL50473
1-o-methyl-.alpha.-d-glucopyranoside
alpha-methyl glucoside
methyl .alpha.-d-(+)-glucoside
1-o-methyl-.alpha.-d-glucoside
.alpha.-methylglucoside [mi]
methyl a-d-glucopyranoside
methyl alpha-(d)-glucopyranoside
alpha-d-methyl glucopyranoside
malphadg
a-d-methyl glucopyranoside
.alpha.-methyl-(d)-glucoside
methyl hexopyranoside #
.alpha.-d-methylglucopyranoside
mfcd00064086
methyl alpha-d-glucopyranoside, for microbiology, >=99.0%
CS-W021034
AS-14322
Q27074402
P16421
ethyl1-methyl-3-phenyl-1h-pyrazole-5-carboxylate
methyl alpha -d-glucopyranoside
EN300-92952
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
alpha-D-glucoside
methyl D-glucoside
[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 (1)

PathwayProteinsCompounds
glycogen degradation I850

Protein Targets (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
retinoic acid nuclear receptor alpha variant 1Homo sapiens (human)Potency53.81850.003041.611522,387.1992AID1159552
[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)
Glycogen phosphorylase, brain formHomo sapiens (human)Ki12,589.29980.00404.06807.0000AID73824
[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, Agglutinin alpha chainArtocarpus integerKd1,000.0000926.0000963.00001,000.0000AID977611
Chain A, Agglutinin alpha chainArtocarpus integerKd1,000.0000926.0000963.00001,000.0000AID977611
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
glycogen catabolic processGlycogen phosphorylase, brain formHomo sapiens (human)
lipopolysaccharide core region biosynthetic processLipopolysaccharide heptosyltransferase 1Escherichia coli K-12
lipopolysaccharide biosynthetic processLipopolysaccharide heptosyltransferase 1Escherichia coli K-12
lipopolysaccharide core region biosynthetic processLipopolysaccharide heptosyltransferase 1Escherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
protein bindingGlycogen phosphorylase, brain formHomo sapiens (human)
glycogen phosphorylase activityGlycogen phosphorylase, brain formHomo sapiens (human)
linear malto-oligosaccharide phosphorylase activityGlycogen phosphorylase, brain formHomo sapiens (human)
SHG alpha-glucan phosphorylase activityGlycogen phosphorylase, brain formHomo sapiens (human)
pyridoxal phosphate bindingGlycogen phosphorylase, brain formHomo sapiens (human)
protein bindingLipopolysaccharide heptosyltransferase 1Escherichia coli K-12
lipopolysaccharide heptosyltransferase activityLipopolysaccharide heptosyltransferase 1Escherichia coli K-12
glycosyltransferase activityLipopolysaccharide heptosyltransferase 1Escherichia coli K-12
ADP-heptose-lipopolysaccharide heptosyltransferase activityLipopolysaccharide heptosyltransferase 1Escherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
extracellular regionGlycogen phosphorylase, brain formHomo sapiens (human)
cytoplasmGlycogen phosphorylase, brain formHomo sapiens (human)
membraneGlycogen phosphorylase, brain formHomo sapiens (human)
azurophil granule lumenGlycogen phosphorylase, brain formHomo sapiens (human)
extracellular exosomeGlycogen phosphorylase, brain formHomo sapiens (human)
cytoplasmGlycogen phosphorylase, brain formHomo sapiens (human)
plasma membraneLipopolysaccharide heptosyltransferase 1Escherichia coli K-12
cytosolLipopolysaccharide heptosyltransferase 1Escherichia coli K-12
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID1125076Cytotoxicity against human HeLa cells assessed as inhibition of number of colonies formed in soft agar after 14 days by microscopic analysis2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID1373944Inhibition of Escherichia coli Heptosyltransferase I assessed as reduction in ADP release using ODLA and ADP-heptose substrates in presence of phospho(enol)pyruvate and NADH by pyruvate kinase and LDH based ADP/NADH coupling assay2018Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4
Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A.
AID1373942Substrate activity at Escherichia coli Heptosyltransferase I assessed as ADP release at 100 uM using phospho(enol)pyruvate and NADH by pyruvate kinase and LDH based ADP/NADH coupling assay2018Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4
Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A.
AID381597Inhibition of Cryptosporidium parvum recombinant Galactose/N-acetylgalactosamine-specific lectin binding to Caco2A cells relative to galactose2007The Journal of biological chemistry, Nov-30, Volume: 282, Issue:48
Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro.
AID1125074Cytotoxicity against human HeLa cells assessed as cell viability after 48 hrs by MTS assay2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID1373943Inhibition of Escherichia coli Heptosyltransferase I assessed as reduction in ADP release at 1 mM using ODLA and ADP-heptose substrates in presence of phospho(enol)pyruvate and NADH by pyruvate kinase and LDH based ADP/NADH coupling assay2018Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4
Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A.
AID1125077Ratio of IC50 to INCC50 for human HeLa cells2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID1125073Cytotoxicity against human HeLa cells assessed as cell viability after 24 hrs by MTS assay2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID1125111Cytotoxicity against tumor promotion-sensitive mouse JB6 Cl41 cells expressing luciferase reporter gene assessed as cell viability after 12 hrs by MTS assay2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID73824Inhibitory activity against Pig Skeletal Glycogen Phosphorylase b2002Journal of medicinal chemistry, Sep-12, Volume: 45, Issue:19
DrugScore meets CoMFA: adaptation of fields for molecular comparison (AFMoC) or how to tailor knowledge-based pair-potentials to a particular protein.
AID381596Inhibition of Cryptosporidium parvum recombinant Galactose/N-acetylgalactosamine-specific lectin binding to Caco2A cells2007The Journal of biological chemistry, Nov-30, Volume: 282, Issue:48
Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro.
AID1125110Inhibition of p53-dependent transcriptional activity in tumor promotion-sensitive mouse JB6 Cl41 cells after 12 hrs by luciferase-based method2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID1125075Cytotoxicity against tumor promotion-sensitive mouse JB6 Cl41 cells assessed as cell viability after 48 hrs by MTS assay2014European journal of medicinal chemistry, Apr-22, Volume: 77Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity.
AID977611Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB2005Journal of molecular biology, Mar-18, Volume: 347, Issue:1
Structural basis for the energetics of jacalin-sugar interactions: promiscuity versus specificity.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (60.00)29.6817
2010's2 (40.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.63

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 weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.63 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.63)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]