DNAmod: 7-methyladenine

Description

Adenine substituted with a methyl group at position N-7.

Chemical properties

Chemical formula	Net charge	Average mass
C6H7N5	0	149.15330

7-methyladenine

Recommended notation

Name	7-methyladenine
Abbreviation	7mA

Nomenclature

IUPAC	SMILES	InChI	InChIKey
7-methyl-7H-purin-6-amine	Cn1cnc2ncnc(N)c12	InChI=1S/C6H7N5/c1-11-3-10-6-4(11)5(7)8-2-9-6/h2-3H,1H3,(H2,7,8,9)	HCGHYQLFMPXSDU-UHFFFAOYSA-N

Nature

Origin	Function	Functional detail	Organisms	References
natural	damage	mutagenic	Escherichia coli Mesocricetus auratus Mus musculus Rattus norvegicus	Margison, GP, et al. 1976. Methylated purines in the deoxyribonucleic acid of various Syrian-golden-hamster tissues after administration of a hepatocarcinogenic dose of dimethylnitrosamine. The Biochemical Journal. 157(3). Lawley, PD, et al. 1976. Removal of minor methylation products 7-methyladenine and 3-methylguanine from DNA of Escherichia coli treated with dimethyl sulphate. Chemico-biological Interactions. 12(2). Frei, JV, et al. 1978. Alkylation of deoxyribonucleic acid in vivo in various organs of C57BL mice by the carcinogens N-methyl-N-nitrosourea, N-ethyl-N-nitrosourea and ethyl methanesulphonate in relation to induction of thymic lymphoma Some applications of high-pressure liquid chromatography. The Biochemical Journal. 174(3). Mandel, HG, et al. 1989. Chromatographic detection of 7-methyladenine in urine of rats administered N-methylnitrosourea: a potential marker for monitoring exposure to methylating carcinogens. Carcinogenesis. 10(4). Mielecki, D, et al. 2014. Ada response - a strategy for repair of alkylated DNA in bacteria. FEMS Microbiology Letters. 355(1).

Database references:

CHEBI:28921

Citations

Frei, JV, et al. 1978. Alkylation of deoxyribonucleic acid in vivo in various organs of C57BL mice by the carcinogens N-methyl-N-nitrosourea, N-ethyl-N-nitrosourea and ethyl methanesulphonate in relation to induction of thymic lymphoma. Some applications of high-pressure liquid chromatography. The Biochemical Journal. 174(3).
Lawley, PD, et al. 1976. Removal of minor methylation products 7-methyladenine and 3-methylguanine from DNA of Escherichia coli treated with dimethyl sulphate. Chemico-biological Interactions. 12(2).
Mandel, HG, et al. 1989. Chromatographic detection of 7-methyladenine in urine of rats administered N-methylnitrosourea: a potential marker for monitoring exposure to methylating carcinogens. Carcinogenesis. 10(4).
Margison, GP, et al. 1976. Methylated purines in the deoxyribonucleic acid of various Syrian-golden-hamster tissues after administration of a hepatocarcinogenic dose of dimethylnitrosamine. The Biochemical Journal. 157(3).
Mielecki, D, et al. 2014. Ada response - a strategy for repair of alkylated DNA in bacteria. FEMS Microbiology Letters. 355(1).
Roux, A, et al. 2012. Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer. Analytical Chemistry. 84(15).