Cyclic GMP (CED0001367)

Record Information
Version1.0
Creation Date2016-05-26 05:32:33 UTC
Update Date2026-08-17 23:40:51 UTC
Accession NumberCHEM035165
Identification
Common NameCyclic GMP
ClassSmall Molecule
Description
Cyclic GMP is an organic compound with the formula C10H12N5O7P and an average molecular weight of 345.21 g/mol. Cyclic GMP belongs to the cyclic purine nucleotides, a subclass of purine nucleotides within the organic compounds. It is classified under the superclass of nucleosides, nucleotides, and analogues. This compound has been recorded as being found in or released from electrical and electronic equipment antennas. In biological systems, it interacts with three recorded protein targets: the cAMP-dependent protein kinase type I-alpha regulatory subunit (PRKAR1A), the potassium/sodium hyperpolarization-activated cyclic nucleotide-gated channel 2 (HCN2), and it acts as an inhibitor of cGMP-dependent 3',5'-cyclic phosphodiesterase (PDE2A).
Contaminant TypeNot Available
Chemical Structure
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
CGMPChEBI
Guanosine 3',5'-cyclic monophosphateChEBI
Guanosine 3',5'-cyclic phosphateChEBI
Guanosine cyclic monophosphateChEBI
Guanosine 3',5'-cyclic monophosphoric acidGenerator
Guanosine 3',5'-cyclic phosphoric acidGenerator
Guanosine cyclic monophosphoric acidGenerator
3',5'-Cyclic GMPHMDB
3',5'-GuanosineHMDB
3',5'-Guanosine monophosphateHMDB
Cyclic 3',5'-guanosine monophosphateHMDB
Cyclic guanosine 3',5'-monophosphateHMDB
Cyclic-GMPHMDB
Guanosine 3',5'-cyclic-monophosphateHMDB
Guanosine 3',5'-monophosphateHMDB
Guanosine cyclic-monophosphateHMDB
Guanosine-cyclic-phosphoric-acidHMDB
Cyclic 3',5'-monophosphate, guanosineHMDB
GMP, CyclicHMDB
Guanosine cyclic-3',5'-monophosphateHMDB
monoPhosphate, guanosine cyclicHMDB
3',5'-monoPhosphate, guanosine cyclicHMDB
Cyclic-3',5'-monophosphate, guanosineHMDB
Guanosine cyclic 3',5'-monophosphateHMDB
Guanosine cyclic 3,5 monophosphateHMDB
Cyclic monophosphate, guanosineHMDB
Guanosine cyclic 3',5' monophosphateHMDB
Chemical FormulaC10H12N5O7P
Average Molecular Mass345.205 g/mol
Monoisotopic Mass345.047 g/mol
CAS Registry Number7665-99-8
IUPAC Name9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-2λ⁵-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one
Traditional Namecyclic-GMP
SMILESNC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1
InChI IdentifierInChI=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
InChI KeyZOOGRGPOEVQQDX-UUOKFMHZSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 3',5'-cyclic purine nucleotides. These are purine nucleotides in which the oxygen atoms linked to the C3 and C5 carbon atoms of the ribose moiety are both bonded the same phosphorus atom of the phosphate group.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPurine nucleotides
Sub ClassCyclic purine nucleotides
Direct Parent3',5'-cyclic purine nucleotides
Alternative Parents
Substituents
  • 3',5'-cyclic purine ribonucleotide
  • Pentose phosphate
  • Glycosyl compound
  • N-glycosyl compound
  • 6-oxopurine
  • Hypoxanthine
  • Monosaccharide phosphate
  • Purinone
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Pyrimidone
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Pyrimidine
  • Vinylogous amide
  • Azole
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Imidazole
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Alcohol
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxygen compound
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Primary amine
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.79 g/LALOGPS
logP-2ALOGPS
logP-2.1ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.05ChemAxon
pKa (Strongest Basic)1.41ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area170.52 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity71.72 m³·mol⁻¹ChemAxon
Polarizability29.19 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-001i-2972000000-80320c485cef8d6d91adNot AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-001i-2972000000-80320c485cef8d6d91adNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0f76-3901000000-c970aad6713a547b2d8fNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-00di-4590100000-edbc82f84eca5a64f5a5Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0uec-2904000000-85af5865e64af24e7691Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0904000000-e34bb3204af3b18ddf11Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0908000000-35925bce602ee60e24eeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0904000000-93fabfb961527e02671eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0907000000-60b56b2fcc437a04a7b8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0908000000-16c413e42a41fa5e7262Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-3904000000-051a745d5db4f607a935Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0901000000-a2a6721a5a98c3d3e945Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0907000000-ae3d3b4dfb6aefdd34c3Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0904000000-fd635f17953dbbff039bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0902000000-36d8b1a240f9f6471886Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0009000000-4c75be42ba8dbd671bbfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0009000000-06ee1dc93418cde4fe39Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-db6612a4a4b92db51507Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-8455683aa1bc0141dd38Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-196c267f58b468d3a8f5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0009000000-7637808812023bf3fb33Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0009000000-34c09019debbbd2ef2a6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0009000000-db049b28da12291887ceNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-c1eb6327e06d564ab1aeNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-0a7d2f76e78d97bbc87bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0905000000-7e46f05235a81a278fa5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0109000000-3c5a594b58764840a3a8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-07560ad69024384c4dc8Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-2904000000-33e4083e488f13a14e46Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0fai-4900000000-c706d8c5595653166237Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0059-5900000000-6f2f8cad7fb46039d201Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udl-3906000000-6812e607650cb8696c43Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-3904000000-b297e27cbbbef23c746fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0009000000-c0ac80716d19269d379eNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-c0b13bd9c949b62b81ebNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0905000000-0c831f6beb886919117cNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udr-0900000000-1d920d3ded57714084d4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-0537b4f22d31ca072327Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-45e1f828790a5ac4b24fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-9c9b22fa2d45c3e9e580Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udj-0904000000-5b7306347c1143cab7a5Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0900000000-e93ce7d84fd56891cb16Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0904000000-65ab088e129c01a9b140Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-fc45e23a1d622d9a6848Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udr-0900000000-d7d3bc38b1c32086753eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-1709000000-881760c573673e832db8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2900000000-f74b8ec55fbea3fdf8cdNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003u-9600000000-d7f00c8f8cec474c7304Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udj-0907000000-c0ef83628b39fde6b0abNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-361a2474138028086bb3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-0900000000-1be953bb7a5905cc7906Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udl-0900000000-af11c01332c5a5626a33Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0f6x-0900000000-e2e2e6e3ea12c01b5286Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2900000000-68beedc644e9c40e1887Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, H2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
2462.0Log mg/kg[1400:4400]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
506AntennasElectrical & Electronic EquipmentNot Available
597ChemosterilantsAgriculture & land managementNot Available
Pathways
0 pathways

No pathways found

No metabolic pathways have been associated with this synthetic chemical

Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureCyclic di-GMP phosphodiesterase RocRQ9HX69Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG12228)Predicted (SEA)0.0778492
Stimulator of interferon genes protein structureClick to view 3D structureStimulator of interferon genes proteinQ86WV6HumansPredicted (SEA)0.233548
Click to view 3D structureCyclic nucleotide-gated channel alpha-2Q00195Rattus norvegicusPredicted (SEA)0.856341
Click to view 3D structureStimulator of interferon genes proteinQ3TBT3Mus musculusPredicted (SEA)0.0778492
Click to view 3D structureRyanodine receptorQ8TA74Hemicentrotus pulcherrimusPredicted (SEA)0.0778492
Click to view 3D structureHypoxanthine-guanine phosphoribosyltransferaseP9WHQ9Mycobacterium tuberculosis (strain ATCC 25618 / H37Rv)Predicted (SEA)0.622794
Click to view 3D structureSerine/threonine protein kinase UL97P16788HHV-5Predicted (SEA)0.467095
Hypoxanthine-guanine-xanthine phosphoribosyltransferase structureClick to view 3D structureHypoxanthine-guanine-xanthine phosphoribosyltransferaseP20035Plasmodium falciparum (isolate FCR-3 / Gambia)Predicted (SEA)0.700643
Adenosine receptor A3 structureClick to view 3D structureAdenosine receptor A3P0DMS8HumansPredicted (SEA)110.624
Click to view 3D structureAdenosine receptor A1P25099Rattus norvegicusPredicted (SEA)98.635
Click to view 3D structureAdenosine receptor A2aP30543Rattus norvegicusPredicted (SEA)89.6823
Heat shock protein HSP 90-alpha structureClick to view 3D structureHeat shock protein HSP 90-alphaP07900HumansPredicted (SEA)46.3203
Endoplasmin structureClick to view 3D structureEndoplasminP14625HumansPredicted (SEA)34.5651
Click to view 3D structureAdenosine receptor A3P28647Rattus norvegicusPredicted (SEA)55.8957
Adenosine receptor A1 structureClick to view 3D structureAdenosine receptor A1P30542HumansPredicted (SEA)109.456
Adenosine receptor A2a structureClick to view 3D structureAdenosine receptor A2aP29274HumansPredicted (SEA)121.834
Xanthine-guanine phosphoribosyltransferase structureClick to view 3D structureXanthine-guanine phosphoribosyltransferaseP0A9M5Escherichia coli (strain K12)Predicted (SEA)0.934191
Click to view 3D structure2-oxoglutarate receptor 1Q6Y1R5Rattus norvegicusPredicted (SEA)26.1573
Adenosylhomocysteinase structureClick to view 3D structureAdenosylhomocysteinaseP23526HumansPredicted (SEA)23.9776
P2X purinoceptor 3 structureClick to view 3D structureP2X purinoceptor 3P56373HumansPredicted (SEA)45.6196
P2Y purinoceptor 1 structureClick to view 3D structureP2Y purinoceptor 1P47900HumansPredicted (SEA)44.2962
Click to view 3D structureP2Y purinoceptor 1P49652Meleagris gallopavoPredicted (SEA)31.8403
Click to view 3D structureP2Y purinoceptor 1P49651Rattus norvegicusPredicted (SEA)26.858
Click to view 3D structureAdenosine receptor A1P47745Cavia porcellusPredicted (SEA)40.5594
Adenosine receptor A2b structureClick to view 3D structureAdenosine receptor A2bP29275HumansPredicted (SEA)118.954
Concentrations
Not Available
External Links
DrugBank IDDB02315
HMDB IDHMDB0001314
FooDB IDFDB030764
Phenol Explorer IDNot Available
KNApSAcK IDC00019673
BiGG ID1485267
BioCyc IDNot Available
METLIN ID6152
PDB IDNot Available
Wikipedia LinkCyclic guanosine monophosphate
Chemspider ID22734
ChEBI ID16356
PubChem Compound ID24316
Kegg Compound IDC00942
YMDB IDYMDB00454
ECMDB IDECMDB04034
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Sekhar, Konjeti R.; Grondin, Pascal; Francis, Sharron H.; Corbin, Jackie D. Design and synthesis of xanthines and cyclic GMP analogs as potent inhibitors of PDE5. Phosphodiesterase Inhibitors (1996), 135-146.
2. Young DV, Cochran ED, Dhawan V, Earl RA, Ellis JL, Garvey DS, Janero DR, Khanapure SP, Letts LG, Melim TL, Murty MG, Shumway MJ, Wey SJ, Zemtseva IS, Selig WM: A comparison of the cyclooxygenase inhibitor-NO donors (CINOD), NMI-1182 and AZD3582, using in vitro biochemical and pharmacological methods. Biochem Pharmacol. 2005 Nov 1;70(9):1343-51.
3. Mashayekhi F, Aghahoseini F, Rezaie A, Zamani MJ, Khorasani R, Abdollahi M: Alteration of cyclic nucleotides levels and oxidative stress in saliva of human subjects with periodontitis. J Contemp Dent Pract. 2005 Nov 15;6(4):46-53.
4. Dobrzynski E, Montanari D, Agata J, Zhu J, Chao J, Chao L: Adrenomedullin improves cardiac function and prevents renal damage in streptozotocin-induced diabetic rats. Am J Physiol Endocrinol Metab. 2002 Dec;283(6):E1291-8.
5. Willoughby SR, Stewart S, Chirkov YY, Kennedy JA, Holmes AS, Horowitz JD: Beneficial clinical effects of perhexiline in patients with stable angina pectoris and acute coronary syndromes are associated with potentiation of platelet responsiveness to nitric oxide. Eur Heart J. 2002 Dec;23(24):1946-54.
6. Barani J, Gottsater A, Mattiasson I, Lindblad B: Platelet and leukocyte activation during aortoiliac angiography and angioplasty. Eur J Vasc Endovasc Surg. 2002 Mar;23(3):220-5.
7. Schiessl B, Strasburger CJ, Bidlingmaier M, Spannagl M, Ugele B, Kainer F: Decreasing resistance in the maternal uterine and peripheral arterial system is apparently unrelated to plasma and urinary levels of nitrite/nitrate and cyclic-guanosinmonophosohate during the course of normal pregnancies. J Perinat Med. 2003;31(4):281-6.
8. Bai X, Wang H, Li Z, Liu K: Correlation between blood cAMP, cGMP levels and traumatic severity in the patients with acute trauma and its clinical significance. J Huazhong Univ Sci Technolog Med Sci. 2004;24(1):68-70.
9. Beltowski J, Jamroz A, Borkowska E: [Heme oxygenase and carbon monoxide in the physiology and pathology of the cardiovascular system]. Postepy Hig Med Dosw (Online). 2004 Mar 3;58:83-99.
10. Rudman D, O'Brien MS, McKinney AS, Hoffman JC Jr, Patterson JH: Observations on the cyclic nucleotide concentrations in human cerebrospinal fluid. J Clin Endocrinol Metab. 1976 Jun;42(6):1088-97.
11. Peracchi M, Lombardi L, Maiolo AT, Bamonti-Catena F, Toschi V, Chiorboli O, Mozzana R, Polli EE: Plasma and urine cyclic nucleotide levels in patients with acute and chronic leukemia. Blood. 1983 Mar;61(3):429-34.
12. Ilecka J: Decreased cerebrospinal fluid cGMP levels in patients with amyotrophic lateral sclerosis. J Neural Transm (Vienna). 2004 Feb;111(2):167-72. Epub 2003 Dec 12.
13. Kotikoski H, Moilanen E, Vapaatalo H, Aine E: Biochemical markers of the L-arginine-nitric oxide pathway in the aqueous humour in glaucoma patients. Acta Ophthalmol Scand. 2002 Apr;80(2):191-5.
14. Hunter KA, Singh GJ, Simpkins CO: Cyclic gmp is a measure of physiologic stress. J Natl Med Assoc. 2001 Jul-Aug;93(7-8):256-62.
15. Zhang H, Zheng RL, Xu CY: [Relationships between lipid peroxidation or cyclic nucleotides and motility in human asthenozoosperm and normosperm]. Shi Yan Sheng Wu Xue Bao. 1998 Dec;31(4):341-6.
16. Martina V, Benso A, Gigliardi VR, Masha A, Origlia C, Granata R, Ghigo E: Short-term dehydroepiandrosterone treatment increases platelet cGMP production in elderly male subjects. Clin Endocrinol (Oxf). 2006 Mar;64(3):260-4.
17. Engelhardt T, Galley HF, MacLennan FM, Webster NR: Saliva cyclic GMP increases during anaesthesia. Br J Anaesth. 2002 Oct;89(4):635-7.
18. Galassi F, Renieri G, Sodi A, Ucci F, Vannozzi L, Masini E: Nitric oxide proxies and ocular perfusion pressure in primary open angle glaucoma. Br J Ophthalmol. 2004 Jun;88(6):757-60.
19. Zhao L, Gray L, Leonardi-Bee J, Weaver CS, Heptinstall S, Bath PM: Effect of aspirin, clopidogrel and dipyridamole on soluble markers of vascular function in normal volunteers and patients with prior ischaemic stroke. Platelets. 2006 Mar;17(2):100-4.
20. Martina V, Origlia C, Bruno GA, Messina M, Ferri M, Pescarmona GP: Serum DHEAS levels correlate with platelet cGMP in normal women. J Endocrinol Invest. 2001 Nov;24(10):RC28-30.
21. St Pierre MV, Schlenker T, Dufour JF, Jefferson DM, Fitz JG, Arias IM: Stimulation of cyclic guanosine monophosphate production by natriuretic peptide in human biliary cells. Gastroenterology. 1998 Apr;114(4):782-90.
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=24591051
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=24705918