Page last updated: 2024-11-07

methyl mannoside, (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

Methyl α-D-mannopyranoside is a naturally occurring sugar that has been the subject of research due to its potential as a therapeutic agent. Its synthesis involves the glycosylation of methanol with D-mannose, often using a catalyst like sulfuric acid. Studies have explored its potential in various applications, including its ability to inhibit the growth of bacteria, its use as a starting material for the synthesis of complex carbohydrates, and its application in the development of drug delivery systems. Furthermore, its structure as a simple sugar makes it a valuable tool in studying carbohydrate recognition and the interactions of sugars with proteins.'
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methylmannoside: RN given refers to (D)-isomer; see also record for 3-O-methylmannose [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

methyl alpha-D-mannoside : A methyl mannoside having alpha-configuration at the anomeric centre. [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 CID101798
CHEMBL ID195368
CHEBI ID43943
SCHEMBL ID136446
MeSH IDM0320916

Synonyms (67)

Synonym
methyl a-d-mannopyranoside
methyl alpha-d-mannopyranoside
o1-methyl-mannose
.alpha.-d-mannopyranoside, methyl
617-04-9
methyl .alpha.-d-mannoside
methyl .alpha.-d-mannopyranoside
SR-01000643077-1
methyl alpha-d-mannopyranoside, >=99% (gc)
25281-48-5
alpha-methyl-d-mannoside
CHEBI:43943 ,
methyl-alpha-d-mannoside
1-o-methyl-alpha-d-mannopyranoside
methyl alpha-d-mannoside
alpha-methyl mannopyranoside
DB01979
1WS5
2BV4
methyl-alpha-d-mannopyranoside
2JDY
2JDN
a-methyl-d-mannoside
alpha-methyl-d-(-)-mannoside
alpha-d-methyl mannoside
35B8275C-EB56-4981-81A0-8E358215B1A9
bdbm50166886
CHEMBL195368 ,
M0368
methyl |a-d-mannopyranoside
(2r,3s,4s,5s,6s)-2-(hydroxymethyl)-6-methoxyoxane-3,4,5-triol
methyl alpha-d-mannoside (van)
nsc 224429
einecs 210-502-3
alpha-d-mannopyranoside, methyl
mannopyranoside, methyl, alpha-d-
nsc 1225
methylmannoside
AKOS016010476
(2r,3s,4s,5s,6s)-2-(hydroxymethyl)-6-methoxy-tetrahydropyran-3,4,5-triol
CCG-53954
EPITOPE ID:145662
S5047
SCHEMBL136446
.alpha.-d-methyl mannoside
mannopyranoside, methyl, .alpha.-d-
1-o-methyl-.alpha.-d-mannopyranoside
.alpha.-methyl-d-mannopyranoside
.alpha.-methyl-d-mannoside
methyl-.alpha.-d-mannopyranoside
methyl-alphad-mannopyranoside
(2r,3s,4s,5s,6s)-2-(hydroxymethyl)-6-methoxytetrahydro-2h-pyran-3,4,5-triol
alpha-methyl-d-mannopyranoside
mfcd00063262
methyl alpha-d-mannopyranoside, for microbiology, >=99.0%
AS-58701
CS-0098154
a-methyl d-mannoside
F16319
o1-methyl-mannose; methyl alpha-d-mannoside; methyl d-mannoside; methyl mannoside
DTXSID10897266
Q27093072
AMY31295
-;methyl alpha-d-mannopyranoside
A868645
methyl -d-mannopyranoside
HY-W039897

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Furthermore, to address the druglikeness of this new class of FimH antagonists, selected pharmacokinetic parameters, which are critical for oral bioavailability (lipophilicity, solubility, and membrane permeation), were determined."( Design, synthesis and biological evaluation of mannosyl triazoles as FimH antagonists.
Abgottspon, D; Cutting, B; Ernst, B; Hartmann, M; Kleeb, S; Rabbani, S; Schwardt, O; Smieško, M; Wittwer, M; Zalewski, A, 2011
)
0.37

Dosage Studied

ExcerptRelevanceReference
" The dose-response maximum was obtained after a 4-day culture using 25% of a supernatant from a mixed lymphocyte culture as a source of AHF."( Concanavalin A-induced B-cell proliferation mediated by allogeneically derived helper factors.
Borrebaeck, CA; Danielsson, L; Möller, SA, 1986
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (2)

ClassDescription
methyl mannoside
alpha-D-mannosideAny mannoside in which the anomeric centre has alpha-configuration.
[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]

Protein Targets (7)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Type 1 fimbrin D-mannose specific adhesinEscherichia coli K-12IC50 (µMol)1.90001.90001.90001.9000AID630658
Fucose-binding lectin PA-IILPseudomonas aeruginosa PAO1IC50 (µMol)100.36000.91002.13002.7400AID1526585; AID1526586; AID1540365; AID1857387; AID1857388
[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 integerKd926.0000926.0000963.00001,000.0000AID977611
Chain A, Agglutinin alpha chainArtocarpus integerKd926.0000926.0000963.00001,000.0000AID977611
Type 1 fimbrin D-mannose specific adhesinEscherichia coli K-12Kd2.20002.20002.25002.3000AID1885011
PA-I galactophilic lectinPseudomonas aeruginosa PAO1Kd0.07100.07100.07100.0710AID1885001
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (20)

Processvia Protein(s)Taxonomy
cell adhesionType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
cell adhesionType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
mechanosensory behaviorType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
cell-substrate adhesionType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
cell adhesion involved in single-species biofilm formationType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
pilus organizationType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
adaptive immune responseC-type lectin domain family 4 member MHomo sapiens (human)
leukocyte cell-cell adhesionC-type lectin domain family 4 member MHomo sapiens (human)
cell-cell recognitionC-type lectin domain family 4 member MHomo sapiens (human)
virion attachment to host cellC-type lectin domain family 4 member MHomo sapiens (human)
receptor-mediated endocytosis of virus by host cellC-type lectin domain family 4 member MHomo sapiens (human)
viral genome replicationC-type lectin domain family 4 member MHomo sapiens (human)
antigen processing and presentationC-type lectin domain family 4 member MHomo sapiens (human)
intracellular signal transductionC-type lectin domain family 4 member MHomo sapiens (human)
innate immune responseC-type lectin domain family 4 member MHomo sapiens (human)
symbiont entry into host cellC-type lectin domain family 4 member MHomo sapiens (human)
receptor-mediated virion attachment to host cellC-type lectin domain family 4 member MHomo sapiens (human)
peptide antigen transportC-type lectin domain family 4 member MHomo sapiens (human)
intracellular transport of virusC-type lectin domain family 4 member MHomo sapiens (human)
immune responseC-type lectin domain family 4 member MHomo sapiens (human)
biological process involved in interspecies interaction between organismsC-type lectin domain family 4 member MHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (10)

Processvia Protein(s)Taxonomy
protein bindingType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
mannose bindingType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
virus receptor activityC-type lectin domain family 4 member MHomo sapiens (human)
protein bindingC-type lectin domain family 4 member MHomo sapiens (human)
carbohydrate bindingC-type lectin domain family 4 member MHomo sapiens (human)
ICAM-3 receptor activityC-type lectin domain family 4 member MHomo sapiens (human)
signaling receptor activityC-type lectin domain family 4 member MHomo sapiens (human)
peptide antigen bindingC-type lectin domain family 4 member MHomo sapiens (human)
virion bindingC-type lectin domain family 4 member MHomo sapiens (human)
metal ion bindingC-type lectin domain family 4 member MHomo sapiens (human)
calcium-dependent protein bindingC-type lectin domain family 4 member MHomo sapiens (human)
mannose bindingC-type lectin domain family 4 member MHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (9)

Processvia Protein(s)Taxonomy
pilusType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
host cell membraneType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
pilus tipType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
pilusType 1 fimbrin D-mannose specific adhesinEscherichia coli K-12
extracellular regionC-type lectin domain family 4 member MHomo sapiens (human)
cytoplasmC-type lectin domain family 4 member MHomo sapiens (human)
plasma membraneC-type lectin domain family 4 member MHomo sapiens (human)
membraneC-type lectin domain family 4 member MHomo sapiens (human)
host cellC-type lectin domain family 4 member MHomo sapiens (human)
external side of plasma membraneC-type lectin domain family 4 member MHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (31)

Assay IDTitleYearJournalArticle
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID596531Displacement of yeast mannan from Concanavalin A by Enzyme-linked lectin assay2011Bioorganic & medicinal chemistry, May-01, Volume: 19, Issue:9
Synthesis of glycopeptide dendrimers, dimerization and affinity for Concanavalin A.
AID1171664Induction of bacterial aggregation in Pseudomonas aeruginosa PAO1 expressing deltalecB mutant assessed as number of aggregates per 100 uL of PBS cell solution at 100 uM by optical microscopy2014Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24
Antiadhesive properties of glycoclusters against Pseudomonas aeruginosa lung infection.
AID1857387Competitive binding affinity to recombinant Pseudomonas aeruginosa PA14 LecB expressed in Escherichia coli BL21(DE3) incubated for 4 to 8 hrs by fluorescent polarization assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Lectin-Targeted Prodrugs Activated by
AID630659Ratio of compound IC50 to n-heptyl alpha-D-mannopyranoside IC50 for Escherichia coli recombinant C-terminal 6His-tagged FimH-CRD with a C-terminal thrombin cleavage site expressed in Escherichia coli HM125 assessed as inhibition of streptavidin-horseradis2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis and biological evaluation of mannosyl triazoles as FimH antagonists.
AID374351Antiviral activity against BKV Gardner ATCC VR837 infected in human WI38 cells assessed as reduction in viral DNA level preincubated for 2 hrs before viral infection measured after 7 days by real time PCR assay2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
BK Virus replication in vitro: limited effect of drugs interfering with viral uptake and intracellular transport.
AID630658Antagonist activity at Escherichia coli recombinant C-terminal 6His-tagged FimH-CRD with a C-terminal thrombin cleavage site expressed in Escherichia coli HM125 assessed as inhibition of streptavidin-horseradish peroxidase conjugated TM-PAA polymer bindin2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis and biological evaluation of mannosyl triazoles as FimH antagonists.
AID1681525Inhibition of Pseudomonas aeruginosa PAO1 LecB expressed in Escherichia coli BL21(DE3) cells incubated for 4 to 8 hrs by (N-(fluorescein-5-yl)-N'-(alpha-L-fucopyranosyl ethylene)thiocarbamide) reporter based fluorescence polarization assay2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Directing Drugs to Bugs: Antibiotic-Carbohydrate Conjugates Targeting Biofilm-Associated Lectins of
AID1459743Inhibition of DLODP in human HepG2 microsomal membrane assessed as reduction in [3H]OSP production at 50 mM using Glc3-0[3H]Man9-5GlcNAc2-PP-dolichol as substrate at pH 5.5 measured after 20 to 60 mins by scintillation counting2017European journal of medicinal chemistry, Jan-05, Volume: 125Synthesis and biological evaluation of chemical tools for the study of Dolichol Linked Oligosaccharide Diphosphatase (DLODP).
AID1526585Inhibition of Pseudomonas aeruginosa PAO1 LecB after 6 hrs by fluorescence polarization assay2019Journal of medicinal chemistry, 10-24, Volume: 62, Issue:20
Anti-biofilm Agents against
AID1858020Binding affinity to Pseudomonas aeruginosa PA-IIL assessed as dissociation constant by isothermal titration calorimetry2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Discovery of
AID630663Permeability of the compound at pH 5 to 7.4 after 16 hrs by PAMPA assay2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis and biological evaluation of mannosyl triazoles as FimH antagonists.
AID1885011Binding affinity to Escherichia coli FimH assessed as dissociation constant by SPR analysis2022Journal of medicinal chemistry, 07-14, Volume: 65, Issue:13
Small Carbohydrate Derivatives as Potent Antibiofilm Agents.
AID596532Ratio of methyl alpha-D-mannoside IC50 to compound IC50 for binding affinity to Concanavalin A per carbohydrate moiety2011Bioorganic & medicinal chemistry, May-01, Volume: 19, Issue:9
Synthesis of glycopeptide dendrimers, dimerization and affinity for Concanavalin A.
AID374353Cytotoxicity against human WI38 cells assessed as reduction in cellular DNA level preincubated for 2 hrs before viral infection measured after 7 days by real time PCR assay2007Antimicrobial agents and chemotherapy, Dec, Volume: 51, Issue:12
BK Virus replication in vitro: limited effect of drugs interfering with viral uptake and intracellular transport.
AID241553Inhibitory concentration against mannan binding relative to concanavalin A; Using QCM(quartz crystal microbalance) assay2005Bioorganic & medicinal chemistry letters, Jun-02, Volume: 15, Issue:11
Redox-responsive and calcium-dependent switching of glycosyldisulfide interactions with Concanavalin A.
AID596530Ratio of methyl alpha-D-mannoside IC50 to compound IC50 for binding affinity to Concanavalin A2011Bioorganic & medicinal chemistry, May-01, Volume: 19, Issue:9
Synthesis of glycopeptide dendrimers, dimerization and affinity for Concanavalin A.
AID1857388Competitive binding affinity to recombinant Pseudomonas aeruginosa PAO1 LecB expressed in Escherichia coli BL21(DE3) incubated for 4 to 8 hrs by fluorescent polarization assay2022Journal of medicinal chemistry, 10-27, Volume: 65, Issue:20
Lectin-Targeted Prodrugs Activated by
AID411108Inhibition of Canavalia ensiformis concanavalin A binding to yeast mannan by ELLA2008Bioorganic & medicinal chemistry letters, Dec-15, Volume: 18, Issue:24
Rational design of novel glycomimetics: inhibitors of concanavalin A.
AID1811212Inhibition of DC-SIGN (unknown origin) expressed in human Jurkat cells assessed as inhibition of EBOV-pseudotyped virus infection measured after 48 hrs by luciferase assay2021Journal of medicinal chemistry, 10-14, Volume: 64, Issue:19
Low-Valent Calix[4]arene Glycoconjugates Based on Hydroxamic Acid Bearing Linkers as Potent Inhibitors in a Model of Ebola Virus Cis-Infection and HCMV-gB-Recombinant Glycoprotein Interaction with MDDC Cells by Blocking DC-SIGN.
AID630665Permeability of the compound assessed as membrane retention at pH 5 to 7.4 after 16 hrs by PAMPA assay2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis and biological evaluation of mannosyl triazoles as FimH antagonists.
AID1171663Induction of bacterial aggregation in Pseudomonas aeruginosa PAO1 expressing deltalecA mutant assessed as number of aggregates per 100 uL of PBS cell solution at 100 uM by optical microscopy2014Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24
Antiadhesive properties of glycoclusters against Pseudomonas aeruginosa lung infection.
AID630664Thermodynamic solubility of the compound at pH 6.5 after 24 hrs by shake flask method using LC-MS analysis2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis and biological evaluation of mannosyl triazoles as FimH antagonists.
AID1885001Binding affinity to recombinant Pseudomonas aeruginosa LecA expressed in Escherichia coli BL21 (DE3) expression system assessed as dissociation constant by isothermal titration calorimetry2022Journal of medicinal chemistry, 07-14, Volume: 65, Issue:13
Small Carbohydrate Derivatives as Potent Antibiofilm Agents.
AID1540365Inhibition of Pseudomonas aeruginosa LecB by fluorescence polarization assay2019Journal of medicinal chemistry, 09-12, Volume: 62, Issue:17
Glycocluster Tetrahydroxamic Acids Exhibiting Unprecedented Inhibition of
AID1526586Competitive inhibition of N-(fluorescein-5-yl)-N'-(alpha-L-fucopyranosyl ethylen)-thiocarbamide binding to Pseudomonas aeruginosa PA14 LecB after 8 to 22 hrs by fluorescence polarization assay2019Journal of medicinal chemistry, 10-24, Volume: 62, Issue:20
Anti-biofilm Agents against
AID1171662Induction of bacterial aggregation in Pseudomonas aeruginosa PAO1 assessed as number of aggregates per 100 uL of PBS cell solution at 100 uM by optical microscopy2014Journal of medicinal chemistry, Dec-26, Volume: 57, Issue:24
Antiadhesive properties of glycoclusters against Pseudomonas aeruginosa lung infection.
AID1885012Relative inhibitory potency, ratio of methyl alpha-D-mannose Kd to compound Kd for binding affinity to C-terminal His-tagged truncated Escherichia coli FimH by SPR analysis2022Journal of medicinal chemistry, 07-14, Volume: 65, Issue:13
Small Carbohydrate Derivatives as Potent Antibiofilm Agents.
AID1681524Inhibition of Pseudomonas aeruginosa PA14 LecB expressed in Escherichia coli BL21(DE3) cells incubated for 4 to 8 hrs by (N-(fluorescein-5-yl)-N'-(alpha-L-fucopyranosyl ethylene)thiocarbamide) reporter based fluorescence polarization assay2020Journal of medicinal chemistry, 10-22, Volume: 63, Issue:20
Directing Drugs to Bugs: Antibiotic-Carbohydrate Conjugates Targeting Biofilm-Associated Lectins of
AID630662Octanol-phosphate buffer distribution coefficient, log D of the compound at pH 7.4 after 2 hrs by shake flask method using LC-MS analysis2011Bioorganic & medicinal chemistry, Nov-01, Volume: 19, Issue:21
Design, synthesis and biological evaluation of mannosyl triazoles as FimH antagonists.
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 (226)

TimeframeStudies, This Drug (%)All Drugs %
pre-199083 (36.73)18.7374
1990's64 (28.32)18.2507
2000's44 (19.47)29.6817
2010's28 (12.39)24.3611
2020's7 (3.10)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 8.94

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 Index8.94 (24.57)
Research Supply Index5.45 (2.92)
Research Growth Index4.39 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (8.94)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (0.43%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other230 (99.57%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]