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.
ID Source | ID |
---|---|
PubMed CID | 64947 |
CHEMBL ID | 131853 |
CHEBI ID | 320061 |
SCHEMBL ID | 50473 |
MeSH ID | M0317107 |
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 |
Class | Description |
---|---|
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] |
Pathway | Proteins | Compounds |
---|---|---|
glycogen degradation I | 8 | 50 |
Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 53.8185 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Glycogen phosphorylase, brain form | Homo sapiens (human) | Ki | 12,589.2998 | 0.0040 | 4.0680 | 7.0000 | AID73824 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
---|---|---|---|---|---|---|---|
Chain A, Agglutinin alpha chain | Artocarpus integer | Kd | 1,000.0000 | 926.0000 | 963.0000 | 1,000.0000 | AID977611 |
Chain A, Agglutinin alpha chain | Artocarpus integer | Kd | 1,000.0000 | 926.0000 | 963.0000 | 1,000.0000 | AID977611 |
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] |
Process | via Protein(s) | Taxonomy |
---|---|---|
glycogen catabolic process | Glycogen phosphorylase, brain form | Homo sapiens (human) |
lipopolysaccharide core region biosynthetic process | Lipopolysaccharide heptosyltransferase 1 | Escherichia coli K-12 |
lipopolysaccharide biosynthetic process | Lipopolysaccharide heptosyltransferase 1 | Escherichia coli K-12 |
lipopolysaccharide core region biosynthetic process | Lipopolysaccharide heptosyltransferase 1 | Escherichia coli K-12 |
[Information is prepared from geneontology information from the June-17-2024 release] |
Process | via Protein(s) | Taxonomy |
---|---|---|
protein binding | Glycogen phosphorylase, brain form | Homo sapiens (human) |
glycogen phosphorylase activity | Glycogen phosphorylase, brain form | Homo sapiens (human) |
linear malto-oligosaccharide phosphorylase activity | Glycogen phosphorylase, brain form | Homo sapiens (human) |
SHG alpha-glucan phosphorylase activity | Glycogen phosphorylase, brain form | Homo sapiens (human) |
pyridoxal phosphate binding | Glycogen phosphorylase, brain form | Homo sapiens (human) |
protein binding | Lipopolysaccharide heptosyltransferase 1 | Escherichia coli K-12 |
lipopolysaccharide heptosyltransferase activity | Lipopolysaccharide heptosyltransferase 1 | Escherichia coli K-12 |
glycosyltransferase activity | Lipopolysaccharide heptosyltransferase 1 | Escherichia coli K-12 |
ADP-heptose-lipopolysaccharide heptosyltransferase activity | Lipopolysaccharide heptosyltransferase 1 | Escherichia coli K-12 |
[Information is prepared from geneontology information from the June-17-2024 release] |
Process | via Protein(s) | Taxonomy |
---|---|---|
extracellular region | Glycogen phosphorylase, brain form | Homo sapiens (human) |
cytoplasm | Glycogen phosphorylase, brain form | Homo sapiens (human) |
membrane | Glycogen phosphorylase, brain form | Homo sapiens (human) |
azurophil granule lumen | Glycogen phosphorylase, brain form | Homo sapiens (human) |
extracellular exosome | Glycogen phosphorylase, brain form | Homo sapiens (human) |
cytoplasm | Glycogen phosphorylase, brain form | Homo sapiens (human) |
plasma membrane | Lipopolysaccharide heptosyltransferase 1 | Escherichia coli K-12 |
cytosol | Lipopolysaccharide heptosyltransferase 1 | Escherichia coli K-12 |
[Information is prepared from geneontology information from the June-17-2024 release] |
Assay ID | Title | Year | Journal | Article |
---|---|---|---|---|
AID1125076 | Cytotoxicity against human HeLa cells assessed as inhibition of number of colonies formed in soft agar after 14 days by microscopic analysis | 2014 | European journal of medicinal chemistry, Apr-22, Volume: 77 | Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity. |
AID1373944 | Inhibition 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 assay | 2018 | Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4 | Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A. |
AID1373942 | Substrate 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 assay | 2018 | Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4 | Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A. |
AID381597 | Inhibition of Cryptosporidium parvum recombinant Galactose/N-acetylgalactosamine-specific lectin binding to Caco2A cells relative to galactose | 2007 | The Journal of biological chemistry, Nov-30, Volume: 282, Issue:48 | Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro. |
AID1125074 | Cytotoxicity against human HeLa cells assessed as cell viability after 48 hrs by MTS assay | 2014 | European journal of medicinal chemistry, Apr-22, Volume: 77 | Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity. |
AID1373943 | Inhibition 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 assay | 2018 | Bioorganic & medicinal chemistry letters, 02-15, Volume: 28, Issue:4 | Synthesis, kinetics and inhibition of Escherichia coli Heptosyltransferase I by monosaccharide analogues of Lipid A. |
AID1125077 | Ratio of IC50 to INCC50 for human HeLa cells | 2014 | European journal of medicinal chemistry, Apr-22, Volume: 77 | Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity. |
AID1125073 | Cytotoxicity against human HeLa cells assessed as cell viability after 24 hrs by MTS assay | 2014 | European journal of medicinal chemistry, Apr-22, Volume: 77 | Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity. |
AID1125111 | Cytotoxicity against tumor promotion-sensitive mouse JB6 Cl41 cells expressing luciferase reporter gene assessed as cell viability after 12 hrs by MTS assay | 2014 | European journal of medicinal chemistry, Apr-22, Volume: 77 | Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity. |
AID73824 | Inhibitory activity against Pig Skeletal Glycogen Phosphorylase b | 2002 | Journal 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. |
AID381596 | Inhibition of Cryptosporidium parvum recombinant Galactose/N-acetylgalactosamine-specific lectin binding to Caco2A cells | 2007 | The Journal of biological chemistry, Nov-30, Volume: 282, Issue:48 | Cryptosporidium p30, a galactose/N-acetylgalactosamine-specific lectin, mediates infection in vitro. |
AID1125110 | Inhibition of p53-dependent transcriptional activity in tumor promotion-sensitive mouse JB6 Cl41 cells after 12 hrs by luciferase-based method | 2014 | European journal of medicinal chemistry, Apr-22, Volume: 77 | Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity. |
AID1125075 | Cytotoxicity against tumor promotion-sensitive mouse JB6 Cl41 cells assessed as cell viability after 48 hrs by MTS assay | 2014 | European journal of medicinal chemistry, Apr-22, Volume: 77 | Quinone-carbohydrate nonglucoside conjugates as a new type of cytotoxic agents: synthesis and determination of in vitro activity. |
AID977611 | Experimentally measured binding affinity data (Kd) for protein-ligand complexes derived from PDB | 2005 | Journal 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] |
Timeframe | Studies, This Drug (%) | All Drugs % |
---|---|---|
pre-1990 | 0 (0.00) | 18.7374 |
1990's | 0 (0.00) | 18.2507 |
2000's | 3 (60.00) | 29.6817 |
2010's | 2 (40.00) | 24.3611 |
2020's | 0 (0.00) | 2.80 |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |
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.
| This Compound (12.63) All Compounds (24.57) |
Publication Type | This drug (%) | All Drugs (%) |
---|---|---|
Trials | 0 (0.00%) | 5.53% |
Reviews | 0 (0.00%) | 6.00% |
Case Studies | 0 (0.00%) | 4.05% |
Observational | 0 (0.00%) | 0.25% |
Other | 5 (100.00%) | 84.16% |
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] |