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
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
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/10486703 | https://www.ncbi.nlm.nih.gov/pubmed/17073662 | https://www.ncbi.nlm.nih.gov/pubmed/15196297 | https://www.ncbi.nlm.nih.gov/pubmed/4155070 | https://www.ncbi.nlm.nih.gov/pubmed/4365701https://www.ncbi.nlm.nih.gov/pubmed/10486703Curator's Comment:: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19089322 |
https://www.ncbi.nlm.nih.gov/pubmed/22297800
Sources: https://www.ncbi.nlm.nih.gov/pubmed/10486703 | https://www.ncbi.nlm.nih.gov/pubmed/17073662 | https://www.ncbi.nlm.nih.gov/pubmed/15196297 | https://www.ncbi.nlm.nih.gov/pubmed/4155070 | https://www.ncbi.nlm.nih.gov/pubmed/4365701https://www.ncbi.nlm.nih.gov/pubmed/10486703
Curator's Comment:: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/19089322 |
https://www.ncbi.nlm.nih.gov/pubmed/22297800
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.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q9Y3Q4 Gene ID: 10021.0 Gene Symbol: HCN4 Target Organism: Homo sapiens (Human) |
1.8 µM [Kd] | ||
Target ID: CHEMBL1827 |
|||
Target ID: CHEMBL4273 |
|||
Target ID: CHEMBL2896 |
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Target ID: CNG channel cyclic nucleotide gated ion |
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Target ID: CHEMBL2363066 |
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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
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
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
Edited
Fri Jun 25 22:39:51 UTC 2021
by
admin
on
Fri Jun 25 22:39:51 UTC 2021
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| Record UNII |
H2D2X058MU
|
| Record Status |
Validated (UNII)
|
| Record Version |
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NCI_THESAURUS |
C1903
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231-641-6
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7665-99-8
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7665-99-8
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H2D2X058MU
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135398570
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M3972
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PRIMARY | Merck Index | ||
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D006152
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DB02315
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C534
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Cyclic GMP
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
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ACTIVE MOIETY |
