Compounds > 2-methyladenine
Page last updated: 2024-12-05

2-methyladenine

Description

2-methyladenine is a naturally occurring purine derivative found in various biological systems. It is often found as a component of tRNA, where it plays a role in the recognition of specific codons during protein synthesis. Research on 2-methyladenine focuses on its biological significance, its role in gene expression, and its potential therapeutic applications. Notable applications include its use as a biomarker for certain cancers and its potential to modulate immune responses. Its synthesis can be achieved via various methods, including chemical modification of adenine or through enzymatic reactions. 2-methyladenine has also been shown to exhibit antiviral activity against certain viruses, further highlighting its biological and therapeutic potential.'

methyladenine : Any member of the class of 6-aminopurines that is adenine bearing a single methyl substituent. [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 CID15048
CHEMBL ID330897
SCHEMBL ID19779
MeSH IDM0138134

Synonyms (41)

Synonym
nsc 26364
2-methyl-1h-purin-6-amine ,
2-methyl-9h-purin-6-ylamine
bdbm50030961
(2-methyl-9h-purin-6-yl)-amine
nsc-26364
nsc26364
sq 23354
1h-purin-6-amine, 2-methyl-
adenine, 2-methyl-
sq 23,354
2-methyl-6-aminopurine
2-methyl-9h-purin-6-amine
1445-08-5
2-methyladenine
2-methyl-7h-purin-6-amine
CHEMBL330897 ,
A808223
2-methyl-7h-purin-6-amine;2-methyl-1h-purin-6-amine
AKOS006338122
AKOS015905348
SCHEMBL19779
2-methyladenin
SMADWRYCYBUIKH-UHFFFAOYSA-N
methyladenine
1h-purin-6-amine, 2-methyl- (9ci)
AKOS024463815
DTXSID80162731
mfcd01674065
methyl-3h-adenine
DS-8040
1h-purin-6-amine,2-methyl-
Q15632702
1h-purin-6-amine pound not 2-methyl- (9ci)
BCP29033
9h-purin-6-amine, 2-methyl-
D84317
BAA44508
CS-0186661
J5S7AW6A3C
sq-23354
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Pathways (1)

PathwayProteinsCompounds
2-methyladeninyl adenosylcobamide biosynthesis from adenosylcobinamide-GDP38

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)IC50 (µMol)8,000.00006.00007.33338.0000AID75706; AID75716; AID75728
Cyclin-dependent kinase 1Homo sapiens (human)IC50 (µMol)320.00000.00041.345210.0000AID51554
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (71)

Processvia Protein(s)Taxonomy
microtubule cytoskeleton organizationGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
positive regulation of cytokine productionGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
glucose metabolic processGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
glycolytic processGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
negative regulation of endopeptidase activityGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
regulation of macroautophagyGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
negative regulation of translationGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
killing of cells of another organismGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
positive regulation of type I interferon productionGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
peptidyl-cysteine S-trans-nitrosylationGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
positive regulation of canonical NF-kappaB signal transductionGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
protein stabilizationGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
defense response to fungusGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
neuron apoptotic processGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
killing by host of symbiont cellsGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
antimicrobial humoral immune response mediated by antimicrobial peptideGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
cellular response to type II interferonGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
G1/S transition of mitotic cell cycleCyclin-dependent kinase 1Homo sapiens (human)
G2/M transition of mitotic cell cycleCyclin-dependent kinase 1Homo sapiens (human)
microtubule cytoskeleton organizationCyclin-dependent kinase 1Homo sapiens (human)
DNA replicationCyclin-dependent kinase 1Homo sapiens (human)
DNA repairCyclin-dependent kinase 1Homo sapiens (human)
chromatin remodelingCyclin-dependent kinase 1Homo sapiens (human)
regulation of transcription by RNA polymerase IICyclin-dependent kinase 1Homo sapiens (human)
protein phosphorylationCyclin-dependent kinase 1Homo sapiens (human)
apoptotic processCyclin-dependent kinase 1Homo sapiens (human)
DNA damage responseCyclin-dependent kinase 1Homo sapiens (human)
mitotic nuclear membrane disassemblyCyclin-dependent kinase 1Homo sapiens (human)
centrosome cycleCyclin-dependent kinase 1Homo sapiens (human)
pronuclear fusionCyclin-dependent kinase 1Homo sapiens (human)
response to xenobiotic stimulusCyclin-dependent kinase 1Homo sapiens (human)
response to toxic substanceCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of gene expressionCyclin-dependent kinase 1Homo sapiens (human)
negative regulation of gene expressionCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of G2/M transition of mitotic cell cycleCyclin-dependent kinase 1Homo sapiens (human)
regulation of Schwann cell differentiationCyclin-dependent kinase 1Homo sapiens (human)
response to amineCyclin-dependent kinase 1Homo sapiens (human)
response to activityCyclin-dependent kinase 1Homo sapiens (human)
cell migrationCyclin-dependent kinase 1Homo sapiens (human)
peptidyl-serine phosphorylationCyclin-dependent kinase 1Homo sapiens (human)
peptidyl-threonine phosphorylationCyclin-dependent kinase 1Homo sapiens (human)
chromosome condensationCyclin-dependent kinase 1Homo sapiens (human)
epithelial cell differentiationCyclin-dependent kinase 1Homo sapiens (human)
animal organ regenerationCyclin-dependent kinase 1Homo sapiens (human)
protein localization to kinetochoreCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of protein import into nucleusCyclin-dependent kinase 1Homo sapiens (human)
regulation of circadian rhythmCyclin-dependent kinase 1Homo sapiens (human)
negative regulation of apoptotic processCyclin-dependent kinase 1Homo sapiens (human)
response to ethanolCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of DNA replicationCyclin-dependent kinase 1Homo sapiens (human)
regulation of embryonic developmentCyclin-dependent kinase 1Homo sapiens (human)
response to cadmium ionCyclin-dependent kinase 1Homo sapiens (human)
response to copper ionCyclin-dependent kinase 1Homo sapiens (human)
symbiont entry into host cellCyclin-dependent kinase 1Homo sapiens (human)
fibroblast proliferationCyclin-dependent kinase 1Homo sapiens (human)
rhythmic processCyclin-dependent kinase 1Homo sapiens (human)
response to axon injuryCyclin-dependent kinase 1Homo sapiens (human)
cell divisionCyclin-dependent kinase 1Homo sapiens (human)
ventricular cardiac muscle cell developmentCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of cardiac muscle cell proliferationCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of mitotic sister chromatid segregationCyclin-dependent kinase 1Homo sapiens (human)
protein-containing complex assemblyCyclin-dependent kinase 1Homo sapiens (human)
cellular response to hydrogen peroxideCyclin-dependent kinase 1Homo sapiens (human)
ERK1 and ERK2 cascadeCyclin-dependent kinase 1Homo sapiens (human)
cellular response to organic cyclic compoundCyclin-dependent kinase 1Homo sapiens (human)
Golgi disassemblyCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of protein localization to nucleusCyclin-dependent kinase 1Homo sapiens (human)
regulation of attachment of mitotic spindle microtubules to kinetochoreCyclin-dependent kinase 1Homo sapiens (human)
microtubule cytoskeleton organization involved in mitosisCyclin-dependent kinase 1Homo sapiens (human)
positive regulation of mitochondrial ATP synthesis coupled electron transportCyclin-dependent kinase 1Homo sapiens (human)
mitotic G2 DNA damage checkpoint signalingCyclin-dependent kinase 1Homo sapiens (human)
protein deubiquitinationCyclin-dependent kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (22)

Processvia Protein(s)Taxonomy
glyceraldehyde-3-phosphate dehydrogenase (NAD+) (phosphorylating) activityGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
protein bindingGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
microtubule bindingGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
aspartic-type endopeptidase inhibitor activityGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
peptidyl-cysteine S-nitrosylase activityGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
identical protein bindingGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
NADP bindingGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
NAD bindingGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
disordered domain specific bindingGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
virus receptor activityCyclin-dependent kinase 1Homo sapiens (human)
chromatin bindingCyclin-dependent kinase 1Homo sapiens (human)
protein kinase activityCyclin-dependent kinase 1Homo sapiens (human)
protein serine/threonine kinase activityCyclin-dependent kinase 1Homo sapiens (human)
cyclin-dependent protein serine/threonine kinase activityCyclin-dependent kinase 1Homo sapiens (human)
protein bindingCyclin-dependent kinase 1Homo sapiens (human)
ATP bindingCyclin-dependent kinase 1Homo sapiens (human)
RNA polymerase II CTD heptapeptide repeat kinase activityCyclin-dependent kinase 1Homo sapiens (human)
kinase activityCyclin-dependent kinase 1Homo sapiens (human)
cyclin bindingCyclin-dependent kinase 1Homo sapiens (human)
Hsp70 protein bindingCyclin-dependent kinase 1Homo sapiens (human)
histone kinase activityCyclin-dependent kinase 1Homo sapiens (human)
cyclin-dependent protein kinase activityCyclin-dependent kinase 1Homo sapiens (human)
protein serine kinase activityCyclin-dependent kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (27)

Processvia Protein(s)Taxonomy
nucleusGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
cytoplasmGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
lipid dropletGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
cytosolGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
plasma membraneGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
microtubule cytoskeletonGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
membraneGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
nuclear membraneGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
vesicleGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
intracellular membrane-bounded organelleGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
perinuclear region of cytoplasmGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
extracellular exosomeGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
GAIT complexGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
ribonucleoprotein complexGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
cytosolGlyceraldehyde-3-phosphate dehydrogenaseHomo sapiens (human)
mitochondrial matrixCyclin-dependent kinase 1Homo sapiens (human)
chromosome, telomeric regionCyclin-dependent kinase 1Homo sapiens (human)
nucleusCyclin-dependent kinase 1Homo sapiens (human)
nucleoplasmCyclin-dependent kinase 1Homo sapiens (human)
mitochondrionCyclin-dependent kinase 1Homo sapiens (human)
endoplasmic reticulum membraneCyclin-dependent kinase 1Homo sapiens (human)
centrosomeCyclin-dependent kinase 1Homo sapiens (human)
cytosolCyclin-dependent kinase 1Homo sapiens (human)
spindle microtubuleCyclin-dependent kinase 1Homo sapiens (human)
membraneCyclin-dependent kinase 1Homo sapiens (human)
midbodyCyclin-dependent kinase 1Homo sapiens (human)
extracellular exosomeCyclin-dependent kinase 1Homo sapiens (human)
mitotic spindleCyclin-dependent kinase 1Homo sapiens (human)
cyclin A1-CDK1 complexCyclin-dependent kinase 1Homo sapiens (human)
cyclin A2-CDK1 complexCyclin-dependent kinase 1Homo sapiens (human)
cyclin B1-CDK1 complexCyclin-dependent kinase 1Homo sapiens (human)
cyclin-dependent protein kinase holoenzyme complexCyclin-dependent kinase 1Homo sapiens (human)
cytoplasmCyclin-dependent kinase 1Homo sapiens (human)
nucleusCyclin-dependent kinase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (4)

Assay IDTitleYearJournalArticle
AID51554Inhibitory activity against purified cdc2 p34/Cyclin B obtained from M phase oocytes of the starfish Marthasterias glacialis.1997Journal of medicinal chemistry, Feb-14, Volume: 40, Issue:4
Cytokinin-derived cyclin-dependent kinase inhibitors: synthesis and cdc2 inhibitory activity of olomoucine and related compounds.
AID75706TInhibition of glyceraldehyde-3-phosphate dehydrogenase in Leishmania mexicana1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
Synthesis and structure-activity relationships of analogs of 2'-deoxy-2'-(3-methoxybenzamido)adenosine, a selective inhibitor of trypanosomal glycosomal glyceraldehyde-3-phosphate dehydrogenase.
AID75728Inhibition of Glyceraldehyde-3-phosphate dehydrogenase in human erythrocytes.1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
Synthesis and structure-activity relationships of analogs of 2'-deoxy-2'-(3-methoxybenzamido)adenosine, a selective inhibitor of trypanosomal glycosomal glyceraldehyde-3-phosphate dehydrogenase.
AID75716Inhibition of glyceraldehyde-3-phosphate dehydrogenase in Trypanosoma brucei1995Journal of medicinal chemistry, Sep-15, Volume: 38, Issue:19
Synthesis and structure-activity relationships of analogs of 2'-deoxy-2'-(3-methoxybenzamido)adenosine, a selective inhibitor of trypanosomal glycosomal glyceraldehyde-3-phosphate dehydrogenase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (50.00)18.7374
1990's2 (33.33)18.2507
2000's0 (0.00)29.6817
2010's1 (16.67)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: 21.53

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 Index21.53 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.18 (4.65)
Search Engine Demand Index18.60 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (21.53)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
adenine
[no description available]		3.06506-aminopurines;
purine nucleobase		Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
olomoucine
olomoucine: inhibits protein P34CDC2. olomoucine : A 9H-purine that is substituted by a (2-hydroxyethyl)nitrilo, benzylnitrilo and a methyl group at positions 2,6 and 9, respectively. It is a cyclin-dependent kinase inhibitor.		1.99102,6-diaminopurines;
ethanolamines		EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
acetylcysteine
N-acetyl-L-cysteine : An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.		2.0510acetylcysteine;
L-cysteine derivative;
N-acetyl-L-amino acid		antidote to paracetamol poisoning;
antiinfective agent;
antioxidant;
antiviral drug;
ferroptosis inhibitor;
geroprotector;
human metabolite;
mucolytic;
radical scavenger;
vulnerary
2,6-diaminopurine
9H-purine-2,6-diamine : A member of the class of 2,6-diaminopurines that is 9H-purine in which the hydrogens at positions 2 and 6 are replaced by amino groups.		1.99102,6-diaminopurines;
primary amino compound		antineoplastic agent
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		1.9810adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
benzylaminopurine
benzylaminopurine: a plant growth regulator. N-benzyladenine : A member of the class of 6-aminopurines that is adenine in which one of the hydrogens of the amino group is replaced by a benzyl group.		1.99106-aminopurinescytokinin;
plant metabolite
9-methyladenine
9-methyladenine : Adenine substituted with a methyl group at position N-9.		1.9910methyladeninemetabolite
2-chloroadenine
6-amino-2-chloropurine: RN & structure given in first source		1.9910
methotrexate
[no description available]		1.9310dicarboxylic acid;
monocarboxylic acid amide;
pteridines		abortifacient;
antimetabolite;
antineoplastic agent;
antirheumatic drug;
dermatologic drug;
DNA synthesis inhibitor;
EC 1.5.1.3 (dihydrofolate reductase) inhibitor;
immunosuppressive agent
cyc 202
seliciclib : 2,6-Diaminopurine carrying benzylamino, (2R)-1-hydroxybutan-2-yl and isopropyl substituents at C-6, C-2-N and N-9 respectively. It is an experimental drug candidate in the family of pharmacological cyclin-dependent kinase (CDK) inhibitors.		1.99102,6-diaminopurinesantiviral drug;
EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
2-[[6-[(phenylmethyl)amino]-9-propan-2-yl-2-purinyl]amino]ethanol
[no description available]		1.9910thiopurine
ConditionIndicatedRelationship StrengthStudiesTrials
Glial Cell Tumors
[description not available]		02.0510
Glioma
Benign and malignant central nervous system neoplasms derived from glial cells (i.e., astrocytes, oligodendrocytes, and ependymocytes). Astrocytes may give rise to astrocytomas (ASTROCYTOMA) or glioblastoma multiforme (see GLIOBLASTOMA). Oligodendrocytes give rise to oligodendrogliomas (OLIGODENDROGLIOMA) and ependymocytes may undergo transformation to become EPENDYMOMA; CHOROID PLEXUS NEOPLASMS; or colloid cysts of the third ventricle. (From Escourolle et al., Manual of Basic Neuropathology, 2nd ed, p21)		02.0510
Neuroblastoma
A common neoplasm of early childhood arising from neural crest cells in the sympathetic nervous system, and characterized by diverse clinical behavior, ranging from spontaneous remission to rapid metastatic progression and death. This tumor is the most common intraabdominal malignancy of childhood, but it may also arise from thorax, neck, or rarely occur in the central nervous system. Histologic features include uniform round cells with hyperchromatic nuclei arranged in nests and separated by fibrovascular septa. Neuroblastomas may be associated with the opsoclonus-myoclonus syndrome. (From DeVita et al., Cancer: Principles and Practice of Oncology, 5th ed, pp2099-2101; Curr Opin Oncol 1998 Jan;10(1):43-51)		02.0510
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