DNAmod: N6-hydroxyadenine

Description

A member of the class of 6-aminopurinnes that is adenine in which one of the exocyclic amino hydrogens is replaced by a hydroxy group.

Chemical properties

Chemical formula	Net charge	Average mass
C5H5N5O	0	151.126

Recommended notation

Name	6-hydroxyaminopurine
Abbreviation	HAP

Nomenclature

IUPAC	SMILES	InChI	InChIKey	Synonyms
N-hydroxy-1H-purin-6-amine	ONc1ncnc2[nH]cnc12	InChI=1S/C5H5N5O/c11-10-5-3-4(7-1-6-3)8-2-9-5/h1-2,11H,(H2,6,7,8,9,10)	CBCQWVQNMGNYEO-UHFFFAOYSA-N	6-n-hydroxylaminopurine 6-hydroxyaminopurine n-hydroxyadenine 6-hydroxylaminopurine n-(7h-purin-6-yl)hydroxylamine n(6)-hydroxyadenine hap

Nature

Origin	Function	Functional detail	Organisms	References
synthetic		mutagenic		Abdul-Masih, MT, et al. 1986. Biochemical studies on the mutagen, 6-N-hydroxylaminopurine Synthesis of the deoxynucleoside triphosphate and its incorporation into DNA in vitro. The Journal of Biological Chemistry. 261(5).

Database references:

CHEBI:78235

Citations

Abdul-Masih, MT, et al. 1986. Biochemical studies on the mutagen, 6-N-hydroxylaminopurine. Synthesis of the deoxynucleoside triphosphate and its incorporation into DNA in vitro. The Journal of Biological Chemistry. 261(5).
Chaube, S, et al. 1969. Teratogenic effects of 6-hydroxylaminopurine in the rat--protection by inosine. Biochemical Pharmacology. 18(5).
Ivanov, EL, et al. 1990. [The effect of mutation him1 characterized by enhanced induced mutagenesis on the genetic effects of 6-N-hydroxylaminopurine in Saccharomyces cerevisiae]. Genetika. 26(1).
Kozmin, SG, et al. 2000. Hypersensitivity of Escherichia coli Delta(uvrB-bio) mutants to 6-hydroxylaminopurine and other base analogs is due to a defect in molybdenum cofactor biosynthesis. Journal of Bacteriology. 182(12).
Lada, AG, et al. 2013. Genome-wide mutation avalanches induced in diploid yeast cells by a base analog or an APOBEC deaminase. PLoS Genetics. 9(9).
Mercier-Parot, L, et al. 1973. [Skeletal malformations in rats produced by 6-hydroxylaminopurine. Attempts at prevention]. Comptes Rendus Des Seances De La Societe De Biologie Et De Ses Filiales. 167(1).
Stepchenkova, EI, et al. 2009. [Genetic control of metabolism of mutagenic purine base analogs 6-hydroxylaminopurine and 2-amino-6-hydroxylaminopurine in yeast Saccharomyces cerevisiae]. Genetika. 45(4).
Waisertreiger, IS, et al. 2010. Elevated Levels of DNA Strand Breaks Induced by a Base Analog in the Human Cell Line with the P32T ITPA Variant. Journal of Nucleic Acids. 2010.