| Record Information |
|---|
| Version |
3.5 |
| Creation Date |
2005-11-16 08:48:42 -0700 |
| Update Date |
2013-02-08 17:10:18 -0700 |
| HMDB ID |
HMDB01314 |
| Secondary Accession Numbers |
None |
| Metabolite Identification |
|---|
| Common Name |
Cyclic GMP |
| Description |
Guanosine cyclic 3',5'-(hydrogen phosphate). A guanine nucleotide containing one phosphate group which is esterified to the sugar moiety in both the 3'- and 5'-positions. It is a cellular regulatory agent and has been described as a second messenger. Its levels increase in response to a variety of hormones, including acetylcholine, insulin, and oxytocin and it has been found to activate specific protein kinases. (From Merck Index, 11th ed). |
| Structure |
Download:
MOL |
SDF |
SMILES |
InChI
Display:
2D Structure |
3D Structure
|
| Synonyms |
- 3',5'-Cyclic GMP
- 3',5'-Guanosine
- 3',5'-Guanosine monophosphate
- cGMP
- Cyclic 3',5'-guanosine monophosphate
- Cyclic GMP
- Cyclic guanosine 3',5'-monophosphate
- Cyclic-GMP
- Guanosine 3',5'-cyclic phosphate
- Guanosine 3',5'-cyclic-monophosphate
- Guanosine 3',5'-monophosphate
- Guanosine cyclic-monophosphate
- Guanosine-cyclic-phosphoric-acid
|
| Chemical Formula |
C10H12N5O7P |
| Average Molecular Weight |
345.2053 |
| Monoisotopic Molecular Weight |
345.047434275 |
| IUPAC Name |
9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-6-yl]-2-amino-6,9-dihydro-1H-purin-6-one |
| Traditional IUPAC Name |
3',5'-cyclic gmp |
| CAS Registry Number |
7665-99-8 |
| SMILES |
NC1=NC2=C(N=CN2[C@@H]2O[C@@H]3COP(O)(=O)O[C@H]3[C@H]2O)C(=O)N1 |
| InChI Identifier |
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 |
| InChI Key |
ZOOGRGPOEVQQDX-UUOKFMHZSA-N |
| Chemical Taxonomy |
|---|
| Kingdom |
Organic Compounds |
| Super Class |
Nucleosides, Nucleotides, and Analogues |
| Class |
Purine Nucleotides |
| Sub Class |
Purine Ribonucleotides |
| Other Descriptors |
- 3',5'-Cyclic nuclcleotides(KEGG)
- 3',5'-cyclic Purine Nucleotides
- 3',5'-cyclic purine nucleotide(ChEBI)
- Aromatic Heteropolycyclic Compounds
|
| Substituents |
- 1 Phosphoribosyl Imidazole
- Aminopyrimidine
- Hypoxanthine
- Imidazole
- Imidazopyrimidine
- Organic Hypophosphite
- Organic Phosphite
- Oxolane
- Phosphoric Acid Ester
- Purine
- Purinone
- Pyrimidine
- Pyrimidone
- Secondary Alcohol
|
| Direct Parent |
Purine Ribonucleoside Monophosphates |
| Ontology |
|---|
| Status |
Detected and Quantified |
| Origin |
|
| Biofunction |
- Component of Purine metabolism
- Second messenger
|
| Application |
Not Available |
| Cellular locations |
- Extracellular
- Nucleus
- Golgi apparatus
|
| Physical Properties |
|---|
| State |
Solid |
| Experimental Properties |
| Property |
Value |
Reference |
| Melting Point |
Not Available |
Not Available |
| Boiling Point |
Not Available |
Not Available |
| Water Solubility |
Not Available |
Not Available |
| LogP |
Not Available |
Not Available |
|
| Predicted Properties |
|
| Spectra |
|---|
|
|
| Biological Properties |
|---|
| Cellular Locations |
- Extracellular
- Nucleus
- Golgi apparatus
|
| Biofluid Locations |
- Blood
- Cerebrospinal Fluid (CSF)
|
| Tissue Location |
- Kidney
- Platelet
- Smooth Muscle
- Aorta
- Blood Vessels
|
| Pathways |
Not Available
|
| Normal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.0055 +/- 0.0003 uM |
Adult (>18 years old) |
Male |
Normal |
Not Available |
| Cerebrospinal Fluid (CSF) |
Detected and Quantified |
|
0.0024 +/- 0.0005 uM |
Adult (>18 years old) |
Both |
Normal |
Not Available |
|
| Abnormal Concentrations |
|---|
|
| Blood |
Detected and Quantified |
|
0.0035 +/- 0.0003 uM |
Adult (>18 years old) |
Both |
Sildenafil-induced headache |
Not Available |
|
| Associated Disorders and Diseases |
|---|
| Disease References |
| Headache |
|---|
- Kruuse C, Frandsen E, Schifter S, Thomsen LL, Birk S, Olesen J: Plasma levels of cAMP, cGMP and CGRP in sildenafil-induced headache. Cephalalgia. 2004 Jul;24(7):547-53.
Pubmed: 15196297
|
|
| Associated OMIM IDs |
None |
| External Links |
|---|
| DrugBank ID |
Not Available |
| Phenol Explorer Compound ID |
Not Available |
| Phenol Explorer Metabolite ID |
Not Available |
| FoodDB ID |
FDB022549 |
| KNApSAcK ID |
Not Available |
| Chemspider ID |
22734 |
| KEGG Compound ID |
C00942 |
| BioCyc ID |
CGMP |
| BiGG ID |
1485267 |
| Wikipedia Link |
Cyclic GMP |
| NuGOwiki Link |
HMDB01314 |
| Metagene Link |
HMDB01314 |
| METLIN ID |
6152 |
| PubChem Compound |
24316 |
| PDB ID |
35G |
| ChEBI ID |
16356 |
| References |
|---|
| Synthesis Reference |
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. |
| Material Safety Data Sheet (MSDS) |
Download (PDF)
|
| General References |
- 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.
Pubmed: 16168964
- 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.
Pubmed: 16299606
- 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.
Pubmed: 12424108
- 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.
Pubmed: 12473257
- 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.
Pubmed: 11914008
- 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.
Pubmed: 12951882
- 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.
Pubmed: 15165120
- 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.
Pubmed: 15069378
- 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.
Pubmed: 180045
- 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.
Pubmed: 6297636
- Ilecka J: Decreased cerebrospinal fluid cGMP levels in patients with amyotrophic lateral sclerosis. J Neural Transm. 2004 Feb;111(2):167-72. Epub 2003 Dec 12.
Pubmed: 14767719
- 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.
Pubmed: 11952488
- 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.
Pubmed: 11491275
- 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.
Pubmed: 12016956
- 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.
Pubmed: 16487434
- Engelhardt T, Galley HF, MacLennan FM, Webster NR: Saliva cyclic GMP increases during anaesthesia. Br J Anaesth. 2002 Oct;89(4):635-7.
Pubmed: 12393367
- 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.
Pubmed: 15148207
- 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.
Pubmed: 16421011
- 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.
Pubmed: 11765058
- 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.
Pubmed: 9516399
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