DNAmod: N6-carbamoylmethyladenine

Description

A nucleobase analogue that is adenine in which one of the exocyclic amino hydrogens is replaced by a carbamoylmethyl group.

Chemical properties

Chemical formula	Net charge	Average mass
C7H8N6O	0	192.178

<i>N</i><sup>6</sup>-carbamoylmethyladenine

Recommended notation

Name	N⁶-carbamoylmethyladenine
Abbreviation	ncm6A

Nomenclature

IUPAC	SMILES	InChI	InChIKey	Synonyms
N(2)-1H-purin-6-ylglycinamide	C=12C(=NC=NC1NCC(=O)N)NC=N2	InChI=1S/C7H8N6O/c8-4(14)1-9-6-5-7(11-2-10-5)13-3-12-6/h2-3H,1H2,(H2,8,14)(H2,9,10,11,12,13)	WIFHSKZDPZUSLN-UHFFFAOYSA-N	2-(9h-purin-6-ylamino)acetamide

Nature

Origin	Function	Functional detail	Organisms	References
natural	hypermodified nucleobase	specific transcriptional roles	Enterobacteria phage Mu	Swinton, D, et al. 1983. Purification and characterization of the unusual deoxynucleoside, alpha-N-(9-beta-D-2'-deoxyribofuranosylpurin-6-yl)glycinamide, specified by the phage Mu modification function. Proceedings of the National Academy of Sciences of the United States of America. 80(24).

Database references:

CHEBI:102525

Citations

Karr, JR, et al. 2012. A whole-cell computational model predicts phenotype from genotype. Cell. 150(2).
Swinton, D, et al. 1983. Purification and characterization of the unusual deoxynucleoside, alpha-N-(9-beta-D-2'-deoxyribofuranosylpurin-6-yl)glycinamide, specified by the phage Mu modification function. Proceedings of the National Academy of Sciences of the United States of America. 80(24).