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8-methyladenosine

CAS No.:
56973-12-7
Catalog Number:
AG00EHLI
Molecular Formula:
Molecular Weight:
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Product Description
Catalog Number:
AG00EHLI
Chemical Name:
8-methyladenosine
CAS Number:
56973-12-7
MDL Number:
MFCD15145304
IUPAC Name:
(2R,3R,4S,5R)-2-(6-amino-8-methylpurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
InChI:
InChI=1S/C11H15N5O4/c1-4-15-6-9(12)13-3-14-10(6)16(4)11-8(19)7(18)5(2-17)20-11/h3,5,7-8,11,17-19H,2H2,1H3,(H2,12,13,14)/t5-,7-,8-,11-/m1/s1
InChI Key:
RTGYRFMTJZYXPD-IOSLPCCCSA-N
Properties
Complexity:
362  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
281.112g/mol
Formal Charge:
0
Heavy Atom Count:
20  
Hydrogen Bond Acceptor Count:
8  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
281.272g/mol
Monoisotopic Mass:
281.112g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
140A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-0.6  
Literature
Title Journal
5'-O-dephosphorylated 2',5'-oligoadenylate (2-5A) with 8-methyladenosine at the 2'-terminus activates human RNase L. Bioorganic & medicinal chemistry letters 20100201
Identification of 8-methyladenosine as the modification catalyzed by the radical SAM methyltransferase Cfr that confers antibiotic resistance in bacteria. RNA (New York, N.Y.) 20090201
Introduction of 8-methyladenosine into 2', 5'-oligoadenylate (2-5A) 2'-terminus induces dramatic shift in binding site of RNase L. Nucleic acids symposium series (2004) 20090101
Anti-cowpox virus activities of certain adenosine analogs, arabinofuranosyl nucleosides, and 2'-fluoro-arabinofuranosyl nucleosides. Nucleosides, nucleotides & nucleic acids 20040101
Synthesis of the antisense oligonucleotides carrying the modified 2-5A molecules at their 5'-termini and their properties. Nucleic acids research. Supplement (2001) 20020101
Vaccinia virus inhibitors as a paradigm for the chemotherapy of poxvirus infections. Clinical microbiology reviews 20010401
Antiviral activity of C-alkylated purine nucleosides obtained by cross-coupling with tetraalkyltin reagents. Journal of medicinal chemistry 19931001
Properties