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7665-99-8,MFCD00070129
Catalog No.:AA005VZ5

7665-99-8 | Guanosine-3',5'-cyclic-monophosphoric acid

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5mg
≥ 99% (HPLC, UV)
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25mg
≥ 99% (HPLC, UV)
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$222.00   $156.00
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100mg
≥ 99% (HPLC, UV)
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250mg
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  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Downstream Synthesis Route
  • Literature
Technical Information
Catalog Number:
AA005VZ5
Chemical Name:
Guanosine-3',5'-cyclic-monophosphoric acid
CAS Number:
7665-99-8
Molecular Formula:
C10H12N5O7P
Molecular Weight:
345.2053
MDL Number:
MFCD00070129
SMILES:
O[C@@H]1[C@@H]2OP(=O)(O)OC[C@H]2O[C@H]1n1cnc2c1nc(N)[nH]c2=O
Properties
Properties
 
BP:
792.7 °C at 760 mmHg  
Form:
Solid  
MP:
>242°C (dec.)  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
616  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
23  
Hydrogen Bond Acceptor Count:
9  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
1  
XLogP3:
-3.4  

Downstream Synthesis Route
Literature

Title: In vitro characterization of zebrafish (Danio rerio) organic anion transporters Oat2a-e.

Journal: Toxicology in vitro : an international journal published in association with BIBRA 20180201

Title: Structural-Activity Relationship of Ginsenosides from Steamed Ginseng in the Treatment of Erectile Dysfunction.

Journal: The American journal of Chinese medicine 20180101

Title: Angiotensin-(1-7) Downregulates Diabetes-Induced cGMP Phosphodiesterase Activation in Rat Corpus Cavernosum.

Journal: BioMed research international 20170101

Title: α1-A680T variant in GUCY1A3 as a candidate conferring protection from pulmonary hypertension among Kyrgyz highlanders.

Journal: Circulation. Cardiovascular genetics 20141201

Title: Erythropoietin prevents endothelial dysfunction in GTP-cyclohydrolase I-deficient hph1 mice.

Journal: Journal of cardiovascular pharmacology 20141201

Title: Erythropoietin increases bioavailability of tetrahydrobiopterin and protects cerebral microvasculature against oxidative stress induced by eNOS uncoupling.

Journal: Journal of neurochemistry 20141101

Title: Dysfunctional nitric oxide signalling increases risk of myocardial infarction.

Journal: Nature 20131219

Title: Uncoupling of eNOS causes superoxide anion production and impairs NO signaling in the cerebral microvessels of hph-1 mice.

Journal: Journal of neurochemistry 20120901

Title: Differential regulation by cyclic nucleotides of the CNGA4 and CNGB1b subunits in olfactory cyclic nucleotide-gated channels.

Journal: Science signaling 20120710

Title: Cobinamides are novel coactivators of nitric oxide receptor that target soluble guanylyl cyclase catalytic domain.

Journal: The Journal of pharmacology and experimental therapeutics 20120301

Title: Phosphodiesterase-5 inhibitor and rat lung ischemia-reperfusion injury.

Journal: Asian cardiovascular & thoracic annals 20120201

Title: Simultaneous LC-MS/MS analysis of the biomarkers cAMP and cGMP in plasma, CSF and brain tissue.

Journal: Journal of neuroscience methods 20120130

Title: CSF concentrations of cAMP and cGMP are lower in patients with Creutzfeldt-Jakob disease but not Parkinson's disease and amyotrophic lateral sclerosis.

Journal: PloS one 20120101

Title: Differential effects of eNOS uncoupling on conduit and small arteries in GTP-cyclohydrolase I-deficient hph-1 mice.

Journal: American journal of physiology. Heart and circulatory physiology 20111201

Title: Anti-proliferative effect of curcumin on melanoma cells is mediated by PDE1A inhibition that regulates the epigenetic integrator UHRF1.

Journal: Molecular nutrition & food research 20111101

Title: eNOS activation mediated by AMPK after stimulation of endothelial cells with histamine or thrombin is dependent on LKB1.

Journal: Biochimica et biophysica acta 20110201

Title: Testosterone-induced modulation of nitric oxide-cGMP signaling pathway and androgenesis in the rat Leydig cells.

Journal: Biology of reproduction 20100901

Title: Pyridoxine improves platelet nitric oxide synthase dysfunction induced by advanced glycation end products in vitro.

Journal: International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20100601

Title: Linaclotide is a potent and selective guanylate cyclase C agonist that elicits pharmacological effects locally in the gastrointestinal tract.

Journal: Life sciences 20100508

Title: Nitric oxide sensitive guanylyl cyclase activity decreases during cerebral postnatal development because of a reduction in heterodimerization.

Journal: Journal of neurochemistry 20100101

Title: Nitric oxide and carbon monoxide act as inhibitory neurotransmitters in the longitudinal muscle of C57BL/6J mouse distal colon.

Journal: Journal of pharmacological sciences 20100101

Title: Role of guanylate cyclase modulators in decompensated heart failure.

Journal: Heart failure reviews 20091201

Title: Decreased platelet nitric oxide contributes to increased circulating monocyte-platelet aggregates in hypertension.

Journal: European heart journal 20091201

Title: Exploiting cGMP-based therapies for the prevention of left ventricular hypertrophy: NO* and beyond.

Journal: Pharmacology & therapeutics 20091201

Title: Anxiolytic effects of phosphodiesterase-2 inhibitors associated with increased cGMP signaling.

Journal: The Journal of pharmacology and experimental therapeutics 20091101

Title: Expression, purification, and characterization of the intra-cellular domain of the ANP receptor.

Journal: Biochimie 20090701

Title: Pyridoxine increases nitric oxide biosynthesis in human platelets.

Journal: International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20090301

Title: cGMP-dependent protein kinase type I is implicated in the regulation of the timing and quality of sleep and wakefulness.

Journal: PloS one 20090101

Title: Up-regulation of 3'5'-cyclic guanosine monophosphate-specific phosphodiesterase in the porcine cumulus-oocyte complex affects steroidogenesis during in vitro maturation.

Journal: Endocrinology 20081101

Title: 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.

Journal: Journal of neuroscience research 20080701

Title: Ammonia inhibits the C-type natriuretic peptide-dependent cyclic GMP synthesis and calcium accumulation in a rat brain endothelial cell line.

Journal: Neurochemistry international 20080501

Title: The effect of sildenafil on ocular blood flow.

Journal: The British journal of ophthalmology 20080401

Title: Role of cGMP-dependent protein kinase in development of tolerance to nitroglycerine in porcine coronary arteries.

Journal: British journal of pharmacology 20080201

Title: NO/cGMP-dependent modulation of synaptic transmission.

Journal: Handbook of experimental pharmacology 20080101

Title: Low nitric oxide: a key factor underlying copper-deficiency teratogenicity.

Journal: Free radical biology & medicine 20071215

Title: Hyperammonemia inhibits the natriuretic peptide receptor 2 (NPR-2)-mediated cyclic GMP synthesis in the astrocytic compartment of rat cerebral cortex slices.

Journal: Neurotoxicology 20071101

Title: Regulation of cGMP-dependent protein kinase-mediated vasodilation by hypoxia-induced reactive species in ovine fetal pulmonary veins.

Journal: American journal of physiology. Lung cellular and molecular physiology 20071001

Title: Decrease in endogenous CGRP release in nitroglycerin tolerance: role of ALDH-2.

Journal: European journal of pharmacology 20070924

Title: 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.

Journal: European journal of pharmacology 20070712

Title: Chronic nitrates blunt the effects of not only nitric oxide but also natriuretic peptides in cardiac myocytes.

Journal: Pharmacological research 20070701

Title: Effect of manganese on luteinizing hormone-releasing hormone secretion in adult male rats.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20070501

Title: Regulation of the expression of soluble guanylyl cyclase by reactive oxygen species.

Journal: British journal of pharmacology 20070401

Title: Manganese stimulates luteinizing hormone releasing hormone secretion in prepubertal female rats: hypothalamic site and mechanism of action.

Journal: The Journal of physiology 20070201

Title: Gene transfer of neuronal nitric oxide synthase into intracardiac Ganglia reverses vagal impairment in hypertensive rats.

Journal: Hypertension (Dallas, Tex. : 1979) 20070201

Title: Adrenomedullin: molecular mechanisms and its role in cardiac disease.

Journal: Amino acids 20070101

Title: The involvement of the nitric oxide in the effects and expression of opioid receptors during peripheral inflammation.

Journal: Current medicinal chemistry 20070101

Title: Atrial natriuretic peptide and long acting natriuretic peptide inhibit MEK 1/2 activation in human prostate cancer cells.

Journal: Anticancer research 20070101

Title: Angiotensin II type 2 receptor expression after vascular injury: differing effects of angiotensin-converting enzyme inhibition and angiotensin receptor blockade.

Journal: Hypertension (Dallas, Tex. : 1979) 20061101

Title: 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.

Journal: Molecular pharmacology 20060901

Title: Synthesis, ocular effects, and nitric oxide donation of imidazole amidoximes.

Journal: European journal of medicinal chemistry 20060901

Title: Ramipril treatment protects against nitrate-induced oxidative stress in eNOS-/- mice: An implication of the NADPH oxidase pathway.

Journal: Journal of cardiovascular pharmacology 20060701

Title: Role of probucol on endothelial dysfunction of epicardial coronary arteries associated with left ventricular hypertrophy.

Journal: Journal of cardiovascular pharmacology 20060501

Title: Cyclic nucleotides modulate genioglossus and hypoglossal responses to excitatory inputs in rats.

Journal: American journal of respiratory and critical care medicine 20060301

Title: Possible involvement of the spinal nitric oxide/cGMP pathway in vincristine-induced painful neuropathy in mice.

Journal: Pain 20050901

Title: Modulatory effects of plant phenols on human multidrug-resistance proteins 1, 4 and 5 (ABCC1, 4 and 5).

Journal: The FEBS journal 20050901

Title: Adrenomedullin induces heme oxygenase-1 gene expression and cGMP formation in rat vascular smooth muscle cells.

Journal: Peptides 20050701

Title: Soluble guanylyl cyclase: more secrets revealed.

Journal: Cellular signalling 20050401

Title: Heme oxygenase-2 protects against glutathione depletion-induced neuronal apoptosis mediated by bilirubin and cyclic GMP.

Journal: Current neurovascular research 20050401

Title: Inhibitory effects on human eosinophil chemotaxis in vitro by BAY 41-2272, an activator of nitric oxide-independent site of soluble guanylate cyclase.

Journal: Biochemical pharmacology 20050315

Title: Function of cGMP-dependent protein kinases in the nervous system.

Journal: Reviews in the neurosciences 20050101

Title: Distribution of cGMP-dependent protein kinase type I and its isoforms in the mouse brain and retina.

Journal: Neuroscience 20050101

Title: Effects of chronic endothelin ET(A) receptor blockade on blood pressure and vascular formation of cyclic guanosine-3',5'-monophosphate in spontaneously hypertensive rats.

Journal: Arzneimittel-Forschung 20050101

Title: Nitric oxide-cyclic GMP pathway with some emphasis on cavernosal contractility.

Journal: International journal of impotence research 20041201

Title: Inhibition of endothelial nitric oxide generation by low-density lipoprotein is partially prevented by L-arginine and L-ascorbate.

Journal: Atherosclerosis 20041001

Title: Role of nitric oxide in NAG-ST induced store-operated calcium entry in rat intestinal epithelial cells.

Journal: Toxicology 20040901

Title: Localization of the NO-cGMP signaling pathway molecules, NOS III-phosphorylation sites, ERK1/2, and Akt/PKB in osteoclasts.

Journal: Journal of periodontology 20040801

Title: Cooperation between aspirin-triggered lipoxin and nitric oxide (NO) mediates antiadhesive properties of 2-(Acetyloxy)benzoic acid 3-(nitrooxymethyl)phenyl ester (NCX-4016) (NO-aspirin) on neutrophil-endothelial cell adherence.

Journal: The Journal of pharmacology and experimental therapeutics 20040601

Title: Antibodies to guanosine triphosphate misidentified as anti-double-stranded DNA antibodies in a patient with antinuclear antibody-negative lupus, due to buckling of insolubilized assay DNA.

Journal: Arthritis and rheumatism 20040501

Title: Gene transfer of endothelial NO synthase, but not eNOS plus inducible NOS, regressed atherosclerosis in rabbits.

Journal: Cardiovascular research 20040201

Title: Role of cyclic GMP on inhibition by nitric oxide donors of human eosinophil chemotaxis in vitro.

Journal: British journal of pharmacology 20040201

Title: Intraplatelet cyclic guanosine-3',5'-monophosphate levels during pregnancy and preeclampsia.

Journal: Hypertension in pregnancy 20040101

Title: Natriuretic peptides--a class of heterologous molecules in plants.

Journal: The international journal of biochemistry & cell biology 20030901

Title: Nitric oxide-induced inhibition of aortic smooth muscle cell motility: role of PTP-PEST and adaptor proteins p130cas and Crk.

Journal: American journal of physiology. Heart and circulatory physiology 20030801

Title: Transduction of the liver with activated Akt normalizes portal pressure in cirrhotic rats.

Journal: Gastroenterology 20030801

Title: Functionally important calmodulin-binding sites in both NH2- and COOH-terminal regions of the cone photoreceptor cyclic nucleotide-gated channel CNGB3 subunit.

Journal: The Journal of biological chemistry 20030704

Title: NO inhibits Na+-K+-2Cl- cotransport via a cytochrome P-450-dependent pathway in renal epithelial cells (MMDD1).

Journal: American journal of physiology. Renal physiology 20030601

Title: Phosphodiesterase inhibitors are neuroprotective to cultured spinal motor neurons.

Journal: Journal of neuroscience research 20030215

Title: Impairment of vascular and platelet levels of nitric oxide and cyclic guanosine-3',5'-monophosphate in cyclosporin A-induced hypertensive rats.

Journal: Fundamental & clinical pharmacology 20030201

Title: Regulation of endothelin-converting enzyme 1 in nephrotic syndrome in rats.

Journal: Nephron. Experimental nephrology 20030101

Title: Nitric oxide preferentially induces type 1 T cell differentiation by selectively up-regulating IL-12 receptor beta 2 expression via cGMP.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20021210

Title: Rod cyclic nucleotide-gated channels have a stoichiometry of three CNGA1 subunits and one CNGB1 subunit.

Journal: Neuron 20021205

Title: Naphazoline-induced neuroendocrine changes: increases in ANP and cGMP levels, but suppression of NE, 3H-NE, and cAMP levels in rabbit eyes.

Journal: Pharmacology 20020701

Title: The atrial natriuretic peptide as a regulator of Kupffer cell functions.

Journal: Shock (Augusta, Ga.) 20020501

Title: The MRP4/ABCC4 gene encodes a novel apical organic anion transporter in human kidney proximal tubules: putative efflux pump for urinary cAMP and cGMP.

Journal: Journal of the American Society of Nephrology : JASN 20020301

Title: Possible involvement of nitric oxide in signaling pigment dispersion in teleostean melanophores.

Journal: Zoological science 20011201

Title: L-citrulline mediated relaxation in the control and lipopolysaccharide-treated rat aortic rings.

Journal: European journal of pharmacology 20011109

Title: Upregulation of phosphodiesterase 1A1 expression is associated with the development of nitrate tolerance.

Journal: Circulation 20011106

Title: Increased contribution of L-arginine-nitric oxide pathway in aorta of mice lacking the gene for vimentin.

Journal: Journal of cardiovascular pharmacology 20011001

Title: Plasma levels of cyclic guanosine-3',5'-monophosphate in the cavernous and systemic blood of healthy males during different functional conditions of the penis.

Journal: Urological research 20011001

Title: Halothane but not isoflurane attenuates interleukin 1beta-induced nitric oxide synthase in vascular smooth muscle.

Journal: Anesthesiology 20010801

Title: Potentiation of sildenafil-induced hypotension is minimal with nitrates generating a radical intermediate.

Journal: Journal of cardiovascular pharmacology 20010701

Title: Electrophysiological characteristics of rat gustatory cyclic nucleotide--gated channel expressed in Xenopus oocytes.

Journal: Journal of neurophysiology 20010601

Title: Mechanism of endothelial dysfunction in apolipoprotein E-deficient mice.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20010601

Title: Adeno-associated virus-mediated transfer of endothelial nitric oxide synthase gene inhibits protein synthesis of rat ventricular cardiomyocytes.

Journal: Cardiovascular drugs and therapy 20010101

Title: Nitric oxide metabolites, prostaglandins and trigeminal vasoactive peptides in internal jugular vein blood during spontaneous migraine attacks.

Journal: Cephalalgia : an international journal of headache 20001201

Title: Cyclic GMP mediates apoptosis induced by sulindac derivatives via activation of c-Jun NH2-terminal kinase 1.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20001001

Title: Nitric oxide regulates renal cortical cyclooxygenase-2 expression.

Journal: American journal of physiology. Renal physiology 20000701

Title: Cloning and characterization of the human and mouse PDE7B, a novel cAMP-specific cyclic nucleotide phosphodiesterase.

Journal: Biochemical and biophysical research communications 20000527

Title: Molecular cloning and characterization of a distinct human phosphodiesterase gene family: PDE11A.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20000328

Title: L-arginine partially reverses established adrenocorticotrophin-induced hypertension and nitric oxide deficiency in the rat.

Journal: Blood pressure 20000101

Title: Sildenafil ameliorates effects of inhaled nitric oxide withdrawal.

Journal: Anesthesiology 19990701

Title: Cloning and characterization of a novel human phosphodiesterase that hydrolyzes both cAMP and cGMP (PDE10A).

Journal: The Journal of biological chemistry 19990625

Title: Inhibition of Alzheimer's beta-amyloid induced vasoactivity and proinflammatory response in microglia by a cGMP-dependent mechanism.

Journal: Experimental neurology 19990501

Title: Platelet nitric oxide metabolites in migraine.

Journal: Cephalalgia : an international journal of headache 19990501

Title: Atrial natriuretic peptide and oxytocin induce natriuresis by release of cGMP.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19990105

Title: C-Linker of cyclic nucleotide-gated channels controls coupling of ligand binding to channel gating.

Journal: The Journal of general physiology 19990101

Title: Molecular cloning and characterization of human PDE8B, a novel thyroid-specific isozyme of 3',5'-cyclic nucleotide phosphodiesterase.

Journal: Biochemical and biophysical research communications 19980929

Title: Isolation and characterization of PDE9A, a novel human cGMP-specific phosphodiesterase.

Journal: The Journal of biological chemistry 19980619

Title: A family of hyperpolarization-activated mammalian cation channels.

Journal: Nature 19980611

Title: Isolation and characterization of PDE8A, a novel human cAMP-specific phosphodiesterase.

Journal: Biochemical and biophysical research communications 19980529

Title: Functional co-assembly among subunits of cyclic-nucleotide-activated, nonselective cation channels, and across species from nematode to human.

Journal: Biophysical journal 19980301

Title: Potentiation of natriuretic peptide action by the beta-adrenergic blocker carvedilol in hypertensive rats: a new antihypertensive mechanism.

Journal: Endocrinology 19980101

Title: Nitric oxide inhibits apoptosis by preventing increases in caspase-3-like activity via two distinct mechanisms.

Journal: The Journal of biological chemistry 19971205

Title: Cloning, chromosomal localization and functional expression of the gene encoding the alpha-subunit of the cGMP-gated channel in human cone photoreceptors.

Journal: The European journal of neuroscience 19971201

Title: Human brain natriuretic peptide reduces blood pressure in normotensive and acute norepinephrine-induced hypertensive rabbits.

Journal: American journal of hypertension 19970601

Title: Molecular cloning, functional expression and chromosomal localization of a human homolog of the cyclic nucleotide-gated ion channel of retinal cone photoreceptors.

Journal: FEBS letters 19960916

Title: Mutations in the gene encoding the alpha subunit of the rod cGMP-gated channel in autosomal recessive retinitis pigmentosa.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19951024

Title: A histidine residue associated with the gate of the cyclic nucleotide-activated channels in rod photoreceptors.

Journal: Neuron 19950101

Title: Subunit 2 (or beta) of retinal rod cGMP-gated cation channel is a component of the 240-kDa channel-associated protein and mediates Ca(2+)-calmodulin modulation.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19941122

Title: Heteromeric olfactory cyclic nucleotide-gated channels: a subunit that confers increased sensitivity to cAMP.

Journal: Proceedings of the National Academy of Sciences of the United States of America 19940913

Title: A second subunit of the olfactory cyclic nucleotide-gated channel confers high sensitivity to cAMP.

Journal: Neuron 19940901

Title: Isolation and characterization of a previously undetected human cAMP phosphodiesterase by complementation of cAMP phosphodiesterase-deficient Saccharomyces cerevisiae.

Journal: The Journal of biological chemistry 19930615

Title: Human rod photoreceptor cGMP-gated channel: amino acid sequence, gene structure, and functional expression.

Journal: The Journal of neuroscience : the official journal of the Society for Neuroscience 19920801

Title: Mechanisms of sodium retention in heart failure: relation to the renin-angiotensin-aldosterone system.

Journal: The American journal of physiology 19910601

Title: New fluorescent analogs of cAMP and cGMP available as substrates for cyclic nucleotide phosphodiesterase.

Journal: The Journal of biological chemistry 19821125

Title: Motor disturbances produced by intrastriatal injection of cyclic AMP and cyclic GMP.

Journal: Archives internationales de pharmacodynamie et de therapie 19761101

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Tags:7665-99-8 Molecular Formula|7665-99-8 MDL|7665-99-8 SMILES|7665-99-8 Guanosine-3',5'-cyclic-monophosphoric acid