Guanosine, 8-nitro-, cyclic 3',5'-(hydrogen phosphate)

8-Nitro-cGMP is an electrophilic second messenger of redox signaling that can form a protein-S-cGMP adduct in s-guanylation process. 8-Nitro-cGMP is an autophagy inducer. 8-Nitro-cGMP promotes RANKL-induced osteoclast differentiation from macrophages. 8-Nitro-cGMP has vasodilator effect, and ameliorates the vascular endothelial dysfunction in diabetic mice[1][2][3][4].

ChEBI: 8-nitroguanosine 3',5'-cyclic monophosphate is a 3',5'-cyclic purine nucleotide that is guanosine 3',5'-cyclic monophosphate in which the hydrogen at position 8 on the purine fragment has been replaced by a nitro group. It has a role as a Brassica napus metabolite, a signalling molecule, a biomarker and a human metabolite. It is a 3',5'-cyclic purine nucleotide and a C-nitro compound. It is functionally related to a 3',5'-cyclic GMP. It is a conjugate acid of an 8-nitroguanosine 3',5'-cyclic monophosphate(1-).

[1] Ihara H, et al. Exposure to Electrophiles Impairs Reactive Persulfide-Dependent Redox Signaling in Neuronal Cells. Chem Res Toxicol. 2017 Sep 18;30(9):1673-1684. DOI:10.1021/acs.chemrestox.7b00120
[2] Tokutomi Y, et al. Vascular responses to 8-nitro-cyclic GMP in non-diabetic and diabetic mice. Br J Pharmacol. 2011 Apr;162(8):1884-93. DOI:10.1111/j.1476-5381.2011.01201.x
[3] Kaneko K, et al. 8-Nitro-cGMP is a promoter of osteoclast differentiation induced by RANKL. Nitric Oxide. 2018 Jan 30;72:46-51. DOI:10.1016/j.niox.2017.11.006
[4] Rawet-Slobodkin M, Elazar Z. 8-nitro-cGMP--a new player in antibacterial autophagy. Mol Cell. 2013 Dec 26;52(6):767-8. DOI:10.1016/j.molcel.2013.12.006