U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H11N5O7P.Na
Molecular Weight 367.1872
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SODIUM GUANOSINE CYCLIC MONOPHOSPHATE

SMILES

[Na+].NC1=NC(=O)C2=C(N1)N(C=N2)[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3O

InChI

InChIKey=KMPIYXNEROUNOG-GWTDSMLYSA-M
InChI=1S/C10H12N5O7P.Na/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);/q;+1/p-1/t3-,5-,6-,9-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C10H11N5O7P
Molecular Weight 344.1974
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Guanosine 3′,5′-cyclic monophosphate (cGMP) is a cyclic nucleotide derived from guanosine triphosphate (GTP). Cyclic GMP is a cellular regulatory agent that acts as a second messenger. Its levels increase in response to a variety of signals (acetylcholine, insulin, oxytocin). cGMP is involved in the regulation of kinases G. cGMP binds to sites on the regulatory units of protein kinase G (PKG) and activates the catalytic units, enabling them to phosphorylate their substrates. cGMP is a common regulator of ion channel conductance, glycogenolysis, and cellular apoptosis. It also relaxes smooth muscle tissues. In blood vessels, relaxation of vascular smooth muscles lead to vasodilation and increased blood flow. cGMP is a secondary messenger in phototransduction in the eye. In the photoreceptors of the mammalian eye, the presence of light activates cGMP phosphodiesterase 5 (PDE5), which degrades cGMP. The sodium ion channels in photoreceptors are cGMP-gated, so degradation of cGMP causes sodium channels to close, which leads to the hyperpolarization of the photoreceptor's plasma membrane and ultimately to visual information being sent to the brain. Mutations in the cGMP phosphodiesterase cause defects in cGMP metabolism leading to retinal disease. Inhibition of cGMP degrading PDE5 by its selective inhibitor sildenafil induced migraine without aura in 10 of 12 migraine patients and in healthy subjects.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9Y3Q4
Gene ID: 10021.0
Gene Symbol: HCN4
Target Organism: Homo sapiens (Human)
1.8 µM [Kd]
Target ID: CNG channel cyclic nucleotide gated ion
Target ID: Q13976
Gene ID: 5592.0
Gene Symbol: PRKG1
Target Organism: Homo sapiens (Human)
Target ID: Q13237
Gene ID: 5593.0
Gene Symbol: PRKG2
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Guanosine 3':5'-cyclic monophosphate and the action of insulin and acetylcholine.
1973 Aug
Glucose inhibition of epinephrine stimulation of hepatic gluconeogenesis by blockade of the alpha-receptor function.
1974 Nov
Observations on the cyclic nucleotide concentrations in human cerebrospinal fluid.
1976 Jun
Motor disturbances produced by intrastriatal injection of cyclic AMP and cyclic GMP.
1976 Nov
Mechanisms of sodium retention in heart failure: relation to the renin-angiotensin-aldosterone system.
1991 Jun
Cyclic nucleotide-dependent protein kinases: intracellular receptors for cAMP and cGMP action.
1999 Aug
Plasma levels of cAMP, cGMP and CGRP in sildenafil-induced headache.
2004 Jul
Effects of chronic endothelin ET(A) receptor blockade on blood pressure and vascular formation of cyclic guanosine-3',5'-monophosphate in spontaneously hypertensive rats.
2005
Distribution of cGMP-dependent protein kinase type I and its isoforms in the mouse brain and retina.
2005
Heme oxygenase-2 protects against glutathione depletion-induced neuronal apoptosis mediated by bilirubin and cyclic GMP.
2005 Apr
Adrenomedullin induces heme oxygenase-1 gene expression and cGMP formation in rat vascular smooth muscle cells.
2005 Jul
A comparison of the cyclooxygenase inhibitor-NO donors (CINOD), NMI-1182 and AZD3582, using in vitro biochemical and pharmacological methods.
2005 Nov 1
Alteration of cyclic nucleotides levels and oxidative stress in saliva of human subjects with periodontitis.
2005 Nov 15
Modulatory effects of plant phenols on human multidrug-resistance proteins 1, 4 and 5 (ABCC1, 4 and 5).
2005 Sep
Possible involvement of the spinal nitric oxide/cGMP pathway in vincristine-induced painful neuropathy in mice.
2005 Sep
The pharmacology of cyclic nucleotide-gated channels: emerging from the darkness.
2006
Ramipril treatment protects against nitrate-induced oxidative stress in eNOS-/- mice: An implication of the NADPH oxidase pathway.
2006 Jul
Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects.
2006 Mar
Effect of aspirin, clopidogrel and dipyridamole on soluble markers of vascular function in normal volunteers and patients with prior ischaemic stroke.
2006 Mar
Cyclic nucleotides modulate genioglossus and hypoglossal responses to excitatory inputs in rats.
2006 Mar 1
Role of probucol on endothelial dysfunction of epicardial coronary arteries associated with left ventricular hypertrophy.
2006 May
Angiotensin II type 2 receptor expression after vascular injury: differing effects of angiotensin-converting enzyme inhibition and angiotensin receptor blockade.
2006 Nov
Synthesis, ocular effects, and nitric oxide donation of imidazole amidoximes.
2006 Sep
Inhibition of proinflammatory tumor necrosis factor-{alpha}-induced inducible nitric-oxide synthase by xanthine-based 7-[2-[4-(2-chlorobenzene)piperazinyl]ethyl]-1,3-dimethylxanthine (KMUP-1) and 7-[2-[4-(4-nitrobenzene)piperazinyl]ethyl]-1, 3-dimethylxanthine (KMUP-3) in rat trachea: The involvement of soluble guanylate cyclase and protein kinase G.
2006 Sep
The involvement of the nitric oxide in the effects and expression of opioid receptors during peripheral inflammation.
2007
Regulation of the expression of soluble guanylyl cyclase by reactive oxygen species.
2007 Apr
Low nitric oxide: a key factor underlying copper-deficiency teratogenicity.
2007 Dec 15
Gene transfer of neuronal nitric oxide synthase into intracardiac Ganglia reverses vagal impairment in hypertensive rats.
2007 Feb
Manganese stimulates luteinizing hormone releasing hormone secretion in prepubertal female rats: hypothalamic site and mechanism of action.
2007 Feb 1
Adrenomedullin: molecular mechanisms and its role in cardiac disease.
2007 Jan
Chronic nitrates blunt the effects of not only nitric oxide but also natriuretic peptides in cardiac myocytes.
2007 Jul
Effects of BAY 41-2272, an activator of nitric oxide-independent site of soluble guanylate cyclase, on human NADPH oxidase system from THP-1 cells.
2007 Jul 12
Effect of manganese on luteinizing hormone-releasing hormone secretion in adult male rats.
2007 May
Hyperammonemia inhibits the natriuretic peptide receptor 2 (NPR-2)-mediated cyclic GMP synthesis in the astrocytic compartment of rat cerebral cortex slices.
2007 Nov
Atrial natriuretic peptide and long acting natriuretic peptide inhibit MEK 1/2 activation in human prostate cancer cells.
2007 Nov-Dec
Decrease in endogenous CGRP release in nitroglycerin tolerance: role of ALDH-2.
2007 Sep 24
NO/cGMP-dependent modulation of synaptic transmission.
2008
The effect of sildenafil on ocular blood flow.
2008 Apr
Role of cGMP-dependent protein kinase in development of tolerance to nitroglycerine in porcine coronary arteries.
2008 Feb
Manganese potentiates nuclear factor-kappaB-dependent expression of nitric oxide synthase 2 in astrocytes by activating soluble guanylate cyclase and extracellular responsive kinase signaling pathways.
2008 Jul
Ammonia inhibits the C-type natriuretic peptide-dependent cyclic GMP synthesis and calcium accumulation in a rat brain endothelial cell line.
2008 May
Up-regulation of 3'5'-cyclic guanosine monophosphate-specific phosphodiesterase in the porcine cumulus-oocyte complex affects steroidogenesis during in vitro maturation.
2008 Nov
cGMP-dependent protein kinase type I is implicated in the regulation of the timing and quality of sleep and wakefulness.
2009
Exploiting cGMP-based therapies for the prevention of left ventricular hypertrophy: NO* and beyond.
2009 Dec
Decreased platelet nitric oxide contributes to increased circulating monocyte-platelet aggregates in hypertension.
2009 Dec
Role of guanylate cyclase modulators in decompensated heart failure.
2009 Dec
Expression, purification, and characterization of the intra-cellular domain of the ANP receptor.
2009 Jul
Pyridoxine increases nitric oxide biosynthesis in human platelets.
2009 Mar
Nitric oxide and carbon monoxide act as inhibitory neurotransmitters in the longitudinal muscle of C57BL/6J mouse distal colon.
2010
Nitric oxide sensitive guanylyl cyclase activity decreases during cerebral postnatal development because of a reduction in heterodimerization.
2010 Jan
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:48:50 UTC 2023
Edited
by admin
on Sat Dec 16 01:48:50 UTC 2023
Record UNII
6WYT1TNR45
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SODIUM GUANOSINE CYCLIC MONOPHOSPHATE
INCI  
INCI  
Official Name English
GUANOSINE 3, 5'-MONOPHOSPHATE, SODIUM SALT
Common Name English
SODIUM GUANOSINE CYCLIC MONOPHOSPHATE [INCI]
Common Name English
GUANOSINE, CYCLIC 3',5'-(HYDROGEN PHOSPHATE), MONOSODIUM SALT
Common Name English
CYCLIC GMP, SODIUM SALT
Common Name English
GUANOSINE, CYCLIC 3',5'-(HYDROGEN PHOSPHATE), SODIUM SALT (1:1)
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID10961153
Created by admin on Sat Dec 16 01:48:50 UTC 2023 , Edited by admin on Sat Dec 16 01:48:50 UTC 2023
PRIMARY
FDA UNII
6WYT1TNR45
Created by admin on Sat Dec 16 01:48:50 UTC 2023 , Edited by admin on Sat Dec 16 01:48:50 UTC 2023
PRIMARY
CAS
40732-48-7
Created by admin on Sat Dec 16 01:48:50 UTC 2023 , Edited by admin on Sat Dec 16 01:48:50 UTC 2023
PRIMARY
PUBCHEM
101533057
Created by admin on Sat Dec 16 01:48:50 UTC 2023 , Edited by admin on Sat Dec 16 01:48:50 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE