N6-Methyladenosine - 10mM in DMSO , CAS No.1867-73-8

CAS: 1867-73-8 Cat. No.: N422283 Molecular Weight: 281.27

GRADE & PURITY 10mM in DMSO

Synonyms

Reserpene | 6-methylamino-9-beta-D-ribofuranosyl-Purine | NCGC00162241-09 | PDSP2_001014 | BP-58658 | CHEBI:21891 | s3190 | Purine, 6-methylamino-9-beta-D-ribofuranosyl- | SCHEMBL40634 | Q6951996 | 6-Methylaminopurinosine | cid_5775 | NCGC00162241-02 | BB

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

Specifications

Synonyms

Reserpene | 6-methylamino-9-beta-D-ribofuranosyl-Purine | NCGC00162241-09 | PDSP2_001014 | BP-58658 | CHEBI:21891 | s3190 | Purine, 6-methylamino-9-beta-D-ribofuranosyl- | SCHEMBL40634 | Q6951996 | 6-Methylaminopurinosine | cid_5775 | NCGC00162241-02 | BB

Specifications & Purity

10mM in DMSO

Biochemical and Physiological Mechanisms

Modified base. Adenosine analog methylated at the nitrogen-6 position. Abundant modification in mRNA, found within some viruses, and most eukaryotes including mammals, insects, plants and yeast. Also found in tRNA, rRNA, and small nuclear RNA (snRNA).

Storage

Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: CNC1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O
• IUPAC Name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methylamino)purin-9-yl]oxolane-3,4-diol
• InChIKey: VQAYFKKCNSOZKM-IOSLPCCCSA-N
• INCHI: 1S/C11H15N5O4/c1-12-9-6-10(14-3-13-9)16(4-15-6)11-8(19)7(18)5(2-17)20-11/h3-5,7-8,11,17-19H,2H2,1H3,(H,12,13,14)/t5-,7-,8-,11-/m1/s1
• Isomeric SMILES: CNC1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
• Molecular Weight: 281.27
• Reaxy-Rn: 1225398
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1225398&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Purine nucleosides

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Purine nucleosides
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Purine nucleosides
• Alternative Parents: Glycosylamines 6-alkylaminopurines Pentoses Secondary alkylarylamines Aminopyrimidines and derivatives N-substituted imidazoles Imidolactams Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary alcohols Organopnictogen compounds Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Purine nucleoside - Glycosyl compound - N-glycosyl compound - 6-alkylaminopurine - 6-aminopurine - Pentose monosaccharide - Imidazopyrimidine - Purine - Aminopyrimidine - Secondary aliphatic/aromatic amine - Monosaccharide - N-substituted imidazole - Pyrimidine - Imidolactam - Tetrahydrofuran - Azole - Imidazole - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Azacycle - Secondary amine - Oxacycle - Amine - Organic nitrogen compound - Alcohol - Hydrocarbon derivative - Organopnictogen compound - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Primary alcohol - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as purine nucleosides. These are compounds comprising a purine base attached to a ribosyl or deoxyribosyl moiety.
• External Descriptors: methyladenosine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ADORA3 Tchem Adenosine receptor A3 (1 Activities)

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Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

ADORA1 Tclin Adenosine A1 receptor (17603 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADRA1A Tclin Alpha-1a adrenergic receptor (8359 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

AVPR1B Tclin Vasopressin V1b receptor (1301 Activities)

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ADORA2A Tclin Adenosine A2a receptor (16305 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADORA2B Tclin Adenosine A2b receptor (7672 Activities)

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ADORA3 Tchem Adenosine A3 receptor (15931 Activities)

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ARSA Tbio Cerebroside-sulfatase (655 Activities)

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HSP90AA1 Tchem Heat shock protein HSP 90-alpha (4115 Activities)

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HT-29 (80576 Activities)

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K562 (73714 Activities)

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MCF7 (126967 Activities)

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HEK293 (82097 Activities)

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EHMT2 Tchem Histone-lysine N-methyltransferase, H3 lysine-9 specific 3 (93046 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

HSP90B1 Tchem Endoplasmin (514 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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ERG Tbio Transcriptional regulator ERG (5589 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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RXFP1 Tchem Relaxin receptor 1 (6345 Activities)

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RXFP2 Tbio Relaxin receptor 2 (377 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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ATAD5 Tbio ATPase family AAA domain-containing protein 5 (122566 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ADAL Tbio Adenosine deaminase-like protein (61 Activities)

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PGK1 Tchem Phosphoglycerate kinase (287 Activities)

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ADORA1 Tclin Adenosine receptor (26 Activities)

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YTHDF2 Tbio YTH domain-containing family protein 2 (23 Activities)

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Associated Targets(non-human)

Hdac6 Histone deacetylase 6 (222 Activities)

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Plasmodium falciparum (966862 Activities)

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J774.A1 (2436 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

pfk 6-phospho-1-fructokinase (7870 Activities)

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Txnrd1 Thioredoxin reductase 1, cytoplasmic (45279 Activities)

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Bacillus anthracis (2936 Activities)

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Adora2b Adenosine A2 receptor (1828 Activities)

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Tick-borne encephalitis virus (132 Activities)

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SARS-CoV-2 (38078 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Molecular Weight: 281.270 g/mol
• XLogP3: -0.400
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 3
• Exact Mass: 281.112 Da
• Monoisotopic Mass: 281.112 Da
• Topological Polar Surface Area: 126.000 Ų
• Heavy Atom Count: 20
• Formal Charge: 0
• Complexity: 349.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Chen Yao, Daizhu Lv, Xueqing Zhou, Pengcheng Fu, Wen Sun, Jinlian Chen, Huan Lin.  (2023)  Exploring urinary modified nucleosides as biomarkers for diabetic retinopathy: Development and validation of a ultra performance liquid chromatography-tandem mass spectrometry method.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:38150972] [10.1016/j.jchromb.2023.123968]

2. Meng Chu, Yichao Qin, Xiuying Lin, Li Ma, Dehai Deng, Daizhu Lv, Pengcheng Fu, Huan Lin.  (2023)  A Preliminary Survey of Transfer RNA Modifications and Modifying Enzymes of the Tropical Plant Cocos nucifera L..  Genes,  14  (6): (1287).  [PMID:37372467] [10.3390/genes14061287]

3. Xiuying Lin, Qianhui Zhang, Yichao Qin, Qisheng Zhong, Daizhu Lv, Xiaopeng Wu, Pengcheng Fu, Huan Lin.  (2022)  Potential Misidentification of Natural Isomers and Mass-Analogs of Modified Nucleosides by Liquid Chromatography–Triple Quadrupole Mass Spectrometry.  Genes,  13  (5): (878).  [PMID:35627263] [10.3390/genes13050878]

4. Mengzhe Guo, Liyan Zhang, Yan Du, Wencheng Du, Dantong Liu, Cheng Guo, Yuanjiang Pan, Daoquan Tang.  (2018)  Enrichment and Quantitative Determination of 5-(Hydroxymethyl)-2′-deoxycytidine, 5-(Formyl)-2′-deoxycytidine, and 5-(Carboxyl)-2′-deoxycytidine in Human Urine of Breast Cancer Patients by Magnetic Hyper-Cross-Linked Microporous Polymers Based on Polyionic Liquid.  ANALYTICAL CHEMISTRY,      [PMID:29316399] [10.1021/acs.analchem.7b04755]

5. Lyuye Zhang, Weibing Zhang, Hailin Wang.  (2024)  Accurate Quantification of Ten Methylated Purine Nucleosides by Highly Sensitive and Stable Isotope-Diluted UHPLC–MS/MS.  ANALYTICAL CHEMISTRY,      [PMID:38970538] [10.1021/acs.analchem.4c01446]

6. Deng Dehai, Qin Yichao, Lin Xiuying, Chu Meng, Lv Daizhu, Lin Huan.  (2025)  Unveiling transfer RNA modifications of oil palm and their dynamic changes during fruit ripening.  BMC PLANT BIOLOGY,  25  (1): (1-17).  [PMID:40155815] [10.1186/s12870-025-06426-9]

7. Sirui Zhu, Yuanyuan Li, You Wu, Yanan Shen, Ying Wang, Yujie Yan, Weijun Chen, Qiong Fu, Yirong Wang, Xiang Yu, Feng Yu.  (2023)  The FERONIA-YUELAO module participates in translational control by modulating the abundance of tRNA fragments in Arabidopsis.  DEVELOPMENTAL CELL,      [PMID:37977150] [10.1016/j.devcel.2023.10.014]

8. Fubin Zhu, Hongzhi Li, Xiang Li, Chunxiu Du, Ting Wang, Xuling Zhou, Xiaobei Xie, Yunxia Shao, Yingzhi Huang, Yanling Hu, Xinxin Guo, Bin Zhu, Shanshan Yu, Xiaoyan Zhang, Binghai Zhao.  (2025)  Mettl3-Mediated m6A Modification Represents a Novel Therapeutic Target for FSGS.  Advanced Science,      [PMID:41417662] [10.1002/advs.202501242]