Page last updated: 2024-12-07

2'-o-methyladenosine

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

Description

2'-O-methyladenosine (2'-OMeA) is a modified nucleoside found in RNA. It is formed by methylation of the 2'-hydroxyl group of adenosine. 2'-OMeA is a common modification in eukaryotic mRNA and is thought to play a role in regulating mRNA stability, translation, and splicing. 2'-OMeA is also found in some tRNAs and rRNAs. It has been shown to protect RNA from degradation by nucleases and can also affect the binding of proteins to RNA. 2'-OMeA is a potent inhibitor of viral replication and has been shown to have therapeutic potential for treating viral infections. 2'-OMeA is also a target for developing new drugs for treating cancer and other diseases.'

cordysinin B : A member of the class of adenosines that is adenosine in which the hydroxy group at position 2' is replaced by a methoxy group. It has been isolated from the mycelia of Cordyceps sinensis. [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 CID102213
CHEMBL ID73237
CHEBI ID69426
SCHEMBL ID25936
MeSH IDM0082529

Synonyms (34)

Synonym
CHEMBL73237 ,
chebi:69426 ,
adenosine, 2'-o-methyl-
(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol
(2r,3r,4r,5r)-5-(6-amino-purin-9-yl)-2-hydroxymethyl-4-methoxy-tetrahydro-furan-3-ol
PDSP2_001038
PDSP1_001054
2'-o-methyladenosine ,
(2r,3r,4r,5r)-5-(6-amino-9h-purin-9-yl)-2-(hydroxymethyl)-4-methoxy-tetrahydrofuran-3-ol
bdbm50144945
(2r,3r,4r,5r)-2-hydroxymethyl-4-methoxy-5-(6-methylamino-purin-9-yl)-tetrahydro-furan-3-ol
2140-79-6
(2r,3r,4r,5r)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
02yx82ihz5 ,
unii-02yx82ihz5
AKOS016003815
(2r,3r,4r,5r)-5-(6-amino-9h-purin-9-yl)-2-(hydroxymethyl)-4-methoxytetrahydrofuran-3-ol
cordysinin b
2'-o-me-a
2'-o-methyl-adenosine
HG1274
SCHEMBL25936
c11h15n5o4
mfcd00056002
DTXSID50175671
5-(6-amino-9h-purin-9-yl)-2-(hydroxymethyl)-4-methoxyoxolan-3-ol
AC-8216
BCP17411
CS-W012268
DS-14586
Q63392855
HY-W011552
PD018166
BP-58835

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" The oral bioavailability of the initial lead was below 5%; therefore, additional analogues were synthesized and screened for liver NTP levels after oral administration to rats."( Liver-targeted prodrugs of 2'-C-methyladenosine for therapy of hepatitis C virus infection.
Boyer, SH; Erion, MD; Fujitaki, JM; Hecker, SJ; Huang, W; Koeplinger, KA; Linemeyer, DL; MacCoss, M; Olsen, DB; Reddy, KR; Reddy, MV; Sun, Z; van Poelje, PD; Varkhedkar, V, 2007
)
0.34

Dosage Studied

ExcerptRelevanceReference
" Lead compounds identified in a primary rat hepatocyte screen were shown to result in liver levels of NTP predictive of efficacy after intravenous dosing to rats."( Liver-targeted prodrugs of 2'-C-methyladenosine for therapy of hepatitis C virus infection.
Boyer, SH; Erion, MD; Fujitaki, JM; Hecker, SJ; Huang, W; Koeplinger, KA; Linemeyer, DL; MacCoss, M; Olsen, DB; Reddy, KR; Reddy, MV; Sun, Z; van Poelje, PD; Varkhedkar, V, 2007
)
0.34
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
[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 (2)

ClassDescription
adenosinesAny purine ribonucleoside that is a derivative of adenosine.
etherAn organooxygen compound with formula ROR, where R is not hydrogen.
[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 (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A3Homo sapiens (human)IC50 (µMol)0.01500.00001.89408.5470AID300162
Adenosine receptor A1Homo sapiens (human)IC50 (µMol)3.00000.00020.68187.7010AID300164
RNA-directed RNA polymerase IC50 (µMol)47.00000.01902.52798.8000AID86858
[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)
Adenosine receptor A3Homo sapiens (human)EC50 (µMol)100.00000.00010.42587.9800AID300160
Adenosine receptor A1Homo sapiens (human)EC50 (µMol)3.00000.00010.99169.8000AID300163
Histamine H1 receptorCavia porcellus (domestic guinea pig)EC50 (µMol)50.00000.00260.53341.2020AID86857
RNA-directed RNA polymerase EC50 (µMol)50.00000.00180.23482.8000AID86857
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (58)

Processvia Protein(s)Taxonomy
inflammatory responseAdenosine receptor A3Homo sapiens (human)
signal transductionAdenosine receptor A3Homo sapiens (human)
activation of adenylate cyclase activityAdenosine receptor A3Homo sapiens (human)
regulation of heart contractionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A3Homo sapiens (human)
response to woundingAdenosine receptor A3Homo sapiens (human)
regulation of norepinephrine secretionAdenosine receptor A3Homo sapiens (human)
negative regulation of cell migrationAdenosine receptor A3Homo sapiens (human)
negative regulation of NF-kappaB transcription factor activityAdenosine receptor A3Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionAdenosine receptor A3Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A3Homo sapiens (human)
temperature homeostasisAdenosine receptor A1Homo sapiens (human)
response to hypoxiaAdenosine receptor A1Homo sapiens (human)
G protein-coupled adenosine receptor signaling pathwayAdenosine receptor A1Homo sapiens (human)
regulation of respiratory gaseous exchange by nervous system processAdenosine receptor A1Homo sapiens (human)
negative regulation of acute inflammatory responseAdenosine receptor A1Homo sapiens (human)
negative regulation of leukocyte migrationAdenosine receptor A1Homo sapiens (human)
positive regulation of peptide secretionAdenosine receptor A1Homo sapiens (human)
positive regulation of systemic arterial blood pressureAdenosine receptor A1Homo sapiens (human)
negative regulation of systemic arterial blood pressureAdenosine receptor A1Homo sapiens (human)
regulation of glomerular filtrationAdenosine receptor A1Homo sapiens (human)
protein targeting to membraneAdenosine receptor A1Homo sapiens (human)
phagocytosisAdenosine receptor A1Homo sapiens (human)
inflammatory responseAdenosine receptor A1Homo sapiens (human)
signal transductionAdenosine receptor A1Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwayAdenosine receptor A1Homo sapiens (human)
cell-cell signalingAdenosine receptor A1Homo sapiens (human)
nervous system developmentAdenosine receptor A1Homo sapiens (human)
negative regulation of cell population proliferationAdenosine receptor A1Homo sapiens (human)
response to inorganic substanceAdenosine receptor A1Homo sapiens (human)
negative regulation of glutamate secretionAdenosine receptor A1Homo sapiens (human)
response to purine-containing compoundAdenosine receptor A1Homo sapiens (human)
lipid catabolic processAdenosine receptor A1Homo sapiens (human)
negative regulation of synaptic transmission, GABAergicAdenosine receptor A1Homo sapiens (human)
positive regulation of nucleoside transportAdenosine receptor A1Homo sapiens (human)
negative regulation of neurotrophin productionAdenosine receptor A1Homo sapiens (human)
positive regulation of protein dephosphorylationAdenosine receptor A1Homo sapiens (human)
vasodilationAdenosine receptor A1Homo sapiens (human)
negative regulation of circadian sleep/wake cycle, non-REM sleepAdenosine receptor A1Homo sapiens (human)
negative regulation of apoptotic processAdenosine receptor A1Homo sapiens (human)
positive regulation of potassium ion transportAdenosine receptor A1Homo sapiens (human)
positive regulation of MAPK cascadeAdenosine receptor A1Homo sapiens (human)
negative regulation of hormone secretionAdenosine receptor A1Homo sapiens (human)
cognitionAdenosine receptor A1Homo sapiens (human)
leukocyte migrationAdenosine receptor A1Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of painAdenosine receptor A1Homo sapiens (human)
negative regulation of lipid catabolic processAdenosine receptor A1Homo sapiens (human)
positive regulation of lipid catabolic processAdenosine receptor A1Homo sapiens (human)
regulation of sensory perception of painAdenosine receptor A1Homo sapiens (human)
negative regulation of synaptic transmission, glutamatergicAdenosine receptor A1Homo sapiens (human)
fatty acid homeostasisAdenosine receptor A1Homo sapiens (human)
excitatory postsynaptic potentialAdenosine receptor A1Homo sapiens (human)
long-term synaptic depressionAdenosine receptor A1Homo sapiens (human)
mucus secretionAdenosine receptor A1Homo sapiens (human)
negative regulation of mucus secretionAdenosine receptor A1Homo sapiens (human)
triglyceride homeostasisAdenosine receptor A1Homo sapiens (human)
regulation of cardiac muscle cell contractionAdenosine receptor A1Homo sapiens (human)
apoptotic signaling pathwayAdenosine receptor A1Homo sapiens (human)
regulation of presynaptic cytosolic calcium ion concentrationAdenosine receptor A1Homo sapiens (human)
negative regulation of long-term synaptic potentiationAdenosine receptor A1Homo sapiens (human)
negative regulation of long-term synaptic depressionAdenosine receptor A1Homo sapiens (human)
G protein-coupled receptor signaling pathwayAdenosine receptor A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
G protein-coupled adenosine receptor activityAdenosine receptor A3Homo sapiens (human)
G protein-coupled receptor bindingAdenosine receptor A1Homo sapiens (human)
purine nucleoside bindingAdenosine receptor A1Homo sapiens (human)
protein bindingAdenosine receptor A1Homo sapiens (human)
heat shock protein bindingAdenosine receptor A1Homo sapiens (human)
G-protein beta/gamma-subunit complex bindingAdenosine receptor A1Homo sapiens (human)
heterotrimeric G-protein bindingAdenosine receptor A1Homo sapiens (human)
protein heterodimerization activityAdenosine receptor A1Homo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (15)

Processvia Protein(s)Taxonomy
plasma membraneAdenosine receptor A3Homo sapiens (human)
presynaptic membraneAdenosine receptor A3Homo sapiens (human)
Schaffer collateral - CA1 synapseAdenosine receptor A3Homo sapiens (human)
dendriteAdenosine receptor A3Homo sapiens (human)
plasma membraneAdenosine receptor A3Homo sapiens (human)
synapseAdenosine receptor A3Homo sapiens (human)
plasma membraneAdenosine receptor A1Homo sapiens (human)
plasma membraneAdenosine receptor A1Homo sapiens (human)
basolateral plasma membraneAdenosine receptor A1Homo sapiens (human)
axolemmaAdenosine receptor A1Homo sapiens (human)
asymmetric synapseAdenosine receptor A1Homo sapiens (human)
presynaptic membraneAdenosine receptor A1Homo sapiens (human)
neuronal cell bodyAdenosine receptor A1Homo sapiens (human)
terminal boutonAdenosine receptor A1Homo sapiens (human)
dendritic spineAdenosine receptor A1Homo sapiens (human)
calyx of HeldAdenosine receptor A1Homo sapiens (human)
postsynaptic membraneAdenosine receptor A1Homo sapiens (human)
presynaptic active zoneAdenosine receptor A1Homo sapiens (human)
synapseAdenosine receptor A1Homo sapiens (human)
dendriteAdenosine receptor A1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID300164Antagonist activity at human adenosine A1 receptor2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Design, synthesis, and biological evaluation of LNA nucleosides as adenosine A3 receptor ligands.
AID300163Agonist activity at human adenosine A1 receptor2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Design, synthesis, and biological evaluation of LNA nucleosides as adenosine A3 receptor ligands.
AID300162Antagonist activity at human adenosine A3 receptor after 15 to 30 mins2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Design, synthesis, and biological evaluation of LNA nucleosides as adenosine A3 receptor ligands.
AID33765Binding affinity determined on Adenosine A2A receptor in rat striatal membranes by measuring displacement of specific [3H]-CGS- 21680 as radioligand.1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.
AID31247Binding affinity determined on Adenosine A1 receptor in rat brain membranes by measuring displacement of specific [3H]PIA as radioligand.1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.
AID86857Inhibition HCV RNA replication2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase.
AID86858Inhibition HCV NS5B-mediated RNA synthesis2004Journal of medicinal chemistry, Apr-22, Volume: 47, Issue:9
Structure-activity relationship of purine ribonucleosides for inhibition of hepatitis C virus RNA-dependent RNA polymerase.
AID33205Binding affinity determined by displacement of specific binding of [125I]N-(4-amino-3-iodophenethyl)-adenosine in membranes of CHO cells stably transfected with the rat Adenosine A3 receptor1995Journal of medicinal chemistry, Mar-31, Volume: 38, Issue:7
Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors.
AID300160Agonist activity at human adenosine A3 receptor after 15 to 30 mins2007Bioorganic & medicinal chemistry, Aug-15, Volume: 15, Issue:16
Design, synthesis, and biological evaluation of LNA nucleosides as adenosine A3 receptor ligands.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (27)

TimeframeStudies, This Drug (%)All Drugs %
pre-19908 (29.63)18.7374
1990's7 (25.93)18.2507
2000's3 (11.11)29.6817
2010's6 (22.22)24.3611
2020's3 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.75

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

MetricThis Compound (vs All)
Research Demand Index24.75 (24.57)
Research Supply Index3.37 (2.92)
Research Growth Index4.78 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.75)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (3.57%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other27 (96.43%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]