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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12N5O7P
Molecular Weight 345.2058
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CYCLIC GMP

SMILES

C1[C@]2([H])[C@]([H])([C@]([H])([C@]([H])(n3cnc4c3[nH]c(=N)nc4O)O2)O)OP(=O)(O)O1

InChI

InChIKey=ZOOGRGPOEVQQDX-UUOKFMHZSA-N
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

HIDE SMILES / InChI

Molecular Formula C10H12N5O7P
Molecular Weight 345.2058
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

In 1960, cyclic guanosine 3′, 5′-monophosphate (cGMP) was synthesized for the first time (Smith et al. 1961) and synthetic compound was shown to be degraded by enzymatic hydrolysis similar to cAMP. cGMP serves as a second messenger molecule, which regulates pleiotropic cellular functions in health and disease. cGMP is generated by particulate or soluble guanylyl cyclases upon stimulation with natriuretic peptides or nitric oxide, respectively. Furthermore, the cGMP concentration is modulated by cGMP-degrading phosphodiesterases. Several targets of cGMP are utilized to effect its various cellular functions. These effector molecules comprise cGMP-dependent protein kinases, ion channels, and phosphodiesterases. The targets of cGMP can regulate downstream pathways and cellular functions (smooth muscle relaxation, platelet inhibition, cell growth and differentiation, bone growth). During the last decade, it emerged that cGMP is a novel drug target for the treatment of pulmonary and cardiovascular disorders. These new drugs act NO-independently with/without heme on soluble guanylyl cyclases or induce subtypes of particular guanylyl cyclases and thereby lead to new therapeutic concepts and horizons.

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
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
Intraplatelet cyclic guanosine-3',5'-monophosphate levels during pregnancy and preeclampsia.
2004
Localization of the NO-cGMP signaling pathway molecules, NOS III-phosphorylation sites, ERK1/2, and Akt/PKB in osteoclasts.
2004 Aug
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
Function of cGMP-dependent protein kinases in the nervous system.
2005
Heme oxygenase-2 protects against glutathione depletion-induced neuronal apoptosis mediated by bilirubin and cyclic GMP.
2005 Apr
Soluble guanylyl cyclase: more secrets revealed.
2005 Apr
Adrenomedullin induces heme oxygenase-1 gene expression and cGMP formation in rat vascular smooth muscle cells.
2005 Jul
Inhibitory effects on human eosinophil chemotaxis in vitro by BAY 41-2272, an activator of nitric oxide-independent site of soluble guanylate cyclase.
2005 Mar 15
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
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
At 100 uM guanosine 3′,5′-cyclic monophosphate effects the rate of carbon flax in isolated rat hepatocytes. It stimulates gluconeogenesis from either galactose or fructose by influencing the rate of reactions involving fructose 6-phosphate in a manner similar to that for glucagon and 3', 5'-cyclic AMP.
Substance Class Chemical
Created
by admin
on Fri Jun 25 22:39:51 UTC 2021
Edited
by admin
on Fri Jun 25 22:39:51 UTC 2021
Record UNII
H2D2X058MU
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CYCLIC GMP
MI  
Common Name English
CYCLIC GUANOSINE 3',5'-MONOPHOSPHATE
Systematic Name English
CYCLIC GMP [MI]
Common Name English
GUANOSINE CYCLIC 3',5'-PHOSPHATE
Systematic Name English
CYCLIC GUANOSINE MONOPHOSPHATE
Systematic Name English
C-GMP
Common Name English
GUANOSINE 3',5'-PHOSPHATE (CYCLIC)
Systematic Name English
GUANOSINE CYCLIC 3',5'-(HYDROGEN PHOSPHATE)
Common Name English
CYCLIC 3',5'-GMP
Systematic Name English
GUANOSINE 3',5'-PHOSPHATE
Systematic Name English
CYCLIC 3',5'-GUANYLIC ACID
Systematic Name English
GUANOSINE 3',5'-MONOPHOSPHATE
Systematic Name English
3',5'-GMP
Systematic Name English
3',5'-CYCLIC GMP
Systematic Name English
CGMP
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1903
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
231-641-6
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY
CAS
7665-99-8
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY
EPA CompTox
7665-99-8
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY
FDA UNII
H2D2X058MU
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY
PUBCHEM
135398570
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY
MERCK INDEX
M3972
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY Merck Index
MESH
D006152
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY
DRUG BANK
DB02315
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY
NCI_THESAURUS
C534
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY
WIKIPEDIA
Cyclic GMP
Created by admin on Fri Jun 25 22:39:51 UTC 2021 , Edited by admin on Fri Jun 25 22:39:51 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> SUBSTRATE
Km
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY