Cyclic guanosine monophosphate

Cyclic guanosine monophosphate
Names
	IUPAC name Guanosine 3′,5′-(hydrogen phosphate)
	Systematic IUPAC name 2-Amino-9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxotetrahydro-2H,4H-2λ5-furo[3,2-d][1,3,2]dioxaphosphol-6-yl]-3,9-dihydro-6H-purin-6-one
	Other names cGMP; 3′,5′-cyclic GMP; 3′:5′-cyclic GMP; Guanosine cyclic monophosphate; Cyclic 3′,5′-GMP; Guanosine 3′,5′-cyclic phosphate
Identifiers
CAS Number	7665-99-8 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:16356 ;
ChEMBL	ChEMBL395336 ;
ChemSpider	22734 ;
ECHA InfoCard	100.028.765
IUPHAR/BPS	2347;
MeSH	Cyclic+GMP
PubChem CID	24316;
UNII	H2D2X058MU ;
CompTox Dashboard (EPA)	DTXSID8040646 ;
	InChI InChI=1S/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 Key: ZOOGRGPOEVQQDX-UUOKFMHZSA-N ; InChI=1/C10H12N5O7P/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17)/t3-,5-,6-,9-/m1/s1 Key: ZOOGRGPOEVQQDX-UUOKFMHZBB;
	SMILES O=C4/N=C(/N)Nc1c4ncn1[C@@H]2O[C@@H]3COP(=O)(O[C@H]3[C@H]2O)O;
Properties
Chemical formula	C10H12N5O7P
Molar mass	345.208 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Cyclic guanosine monophosphate (cGMP) is a cyclic nucleotide derived from guanosine triphosphate (GTP). cGMP acts as a second messenger much like cyclic AMP. Its most likely mechanism of action is activation of intracellular protein kinases in response to the binding of membrane-impermeable peptide hormones to the external cell surface.^[1] Through protein kinases activation, cGMP can relax smooth muscle.^[2] cGMP concentration in urine can be measured for kidney function and diabetes detection.^[3]

^ Francis SH, Corbin JD (August 1999). "Cyclic nucleotide-dependent protein kinases: intracellular receptors for cAMP and cGMP action". Critical Reviews in Clinical Laboratory Sciences. 36 (4): 275–328. doi:10.1080/10408369991239213. PMID 10486703.
^ Carvajal JA, Germain AM, Huidobro-Toro JP, Weiner CP (September 2000). "Molecular mechanism of cGMP-mediated smooth muscle relaxation". Journal of Cellular Physiology. 184 (3): 409–420. doi:10.1002/1097-4652(200009)184:3<409::aid-jcp16>3.0.co;2-k. PMID 10911373. S2CID 22530053.
^ Chaykovska L, Heunisch F, von Einem G, Hocher CF, Tsuprykov O, Pavkovic M, et al. (2018-04-12). Shimosawa T (ed.). "Urinary cGMP predicts major adverse renal events in patients with mild renal impairment and/or diabetes mellitus before exposure to contrast medium". PLOS ONE. 13 (4): e0195828. Bibcode:2018PLoSO..1395828C. doi:10.1371/journal.pone.0195828. PMC 5896998. PMID 29649334.

[1] Francis SH, Corbin JD (August 1999). "Cyclic nucleotide-dependent protein kinases: intracellular receptors for cAMP and cGMP action". Critical Reviews in Clinical Laboratory Sciences. 36 (4): 275–328. doi:10.1080/10408369991239213. PMID 10486703.

[2] Carvajal JA, Germain AM, Huidobro-Toro JP, Weiner CP (September 2000). "Molecular mechanism of cGMP-mediated smooth muscle relaxation". Journal of Cellular Physiology. 184 (3): 409–420. doi:10.1002/1097-4652(200009)184:3<409::aid-jcp16>3.0.co;2-k. PMID 10911373. S2CID 22530053.

[3] Chaykovska L, Heunisch F, von Einem G, Hocher CF, Tsuprykov O, Pavkovic M, et al. (2018-04-12). Shimosawa T (ed.). "Urinary cGMP predicts major adverse renal events in patients with mild renal impairment and/or diabetes mellitus before exposure to contrast medium". PLOS ONE. 13 (4): e0195828. Bibcode:2018PLoSO..1395828C. doi:10.1371/journal.pone.0195828. PMC 5896998. PMID 29649334.

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