DNAmod: hypoxanthine

Description

A purine nucleobase that consists of purine bearing an oxo substituent at position 6.

Chemical properties

Chemical formula	Net charge	Average mass
C5H4N4O	0	136.11162

hypoxanthine

Recommended notation

Name	inosine
Abbreviation	xI

Nomenclature

IUPAC	SMILES	InChI	InChIKey	Synonyms
1,7-dihydro-6H-purin-6-one	O=c1[nH]cnc2nc[nH]c12	InChI=1S/C5H4N4O/c10-5-3-4(7-1-6-3)8-2-9-5/h1-2H,(H2,6,7,8,9,10)	FDGQSTZJBFJUBT-UHFFFAOYSA-N	purine-6-ol 9h-purin-6(1h)-one hyp purin-6(1h)-one 6-oxopurine 6(1h)-purinone

Nature

Origin	Function	Functional detail	Organisms	References
natural	damage and hypermodified nucleobase		Escherichia coli Homo sapiens Rattus norvegicus Thermoanaerobacter acetoethylicus	Ehrlich, M, et al. 1985. DNA methylation in thermophilic bacteria: N4-methylcytosine, 5-methylcytosine, and N6-methyladenine. Nucleic Acids Research. 13(4). Nguyen, T, et al. 1992. DNA damage and mutation in human cells exposed to nitric oxide in vitro. Proceedings of the National Academy of Sciences of the United States of America. 89(7). Saparbaev, M, et al. 1994. Excision of hypoxanthine from DNA containing dIMP residues by the Escherichia coli, yeast, rat, and human alkylpurine DNA glycosylases. Proceedings of the National Academy of Sciences of the United States of America. 91(13).

Database references:

CHEBI:17368

Citations

BUTLER, VP, et al. 1965. A STUDY OF THE CROSS-REACTIVITY OF ANTIPURIN-6-OYL SERUM WITH DEOXYRIBONUCLEIC ACID (DNA). The Journal of Experimental Medicine. 121.
Bordbar, A, et al. 2012. Model-driven multi-omic data analysis elucidates metabolic immunomodulators of macrophage activation. Molecular Systems Biology. 8.
Ehrlich, M, et al. 1985. DNA methylation in thermophilic bacteria: N4-methylcytosine, 5-methylcytosine, and N6-methyladenine. Nucleic Acids Research. 13(4).
Nguyen, T, et al. 1992. DNA damage and mutation in human cells exposed to nitric oxide in vitro. Proceedings of the National Academy of Sciences of the United States of America. 89(7).
Saparbaev, M, et al. 1994. Excision of hypoxanthine from DNA containing dIMP residues by the Escherichia coli, yeast, rat, and human alkylpurine DNA glycosylases. Proceedings of the National Academy of Sciences of the United States of America. 91(13).
Wamser, MN, et al. 2013. Effect of hypoxanthine, antioxidants and allopurinol on cholinesterase activities in rats. Journal of Neural Transmission (Vienna, Austria : 1996). 120(9).
Zieliński, J, et al. 2013. Hypoxanthine as a predictor of performance in highly trained athletes. International Journal of Sports Medicine. 34(12).