Cyclic guanosine monophosphate
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IUPAC name
Guanosine 3′,5′-(hydrogen phosphate)
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Systematic IUPAC name
2-Amino-9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxotetrahydro-2H,4H-2λ5-furo[3,2-d][1,3,2]dioxaphosphol-6-yl]-3,9-dihydro-6H-purin-6-one | |
Other names
cGMP; 3′,5′-cyclic GMP; 3′:5′-cyclic GMP; Guanosine cyclic monophosphate; Cyclic 3′,5′-GMP; Guanosine 3′,5′-cyclic phosphate
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Identifiers | |
3D model (
JSmol ) |
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ChEBI | |
ChEMBL | |
ChemSpider | |
ECHA InfoCard
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100.028.765 |
IUPHAR/BPS |
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MeSH | Cyclic+GMP |
PubChem CID
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UNII | |
CompTox Dashboard (EPA)
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Properties | |
C10H12N5O7P | |
Molar mass | 345.208 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Cyclic guanosine monophosphate (cGMP) is a
Synthesis
Functions
cGMP is a common regulator of
cGMP is a secondary messenger in
cGMP is also seen to mediate the switching on of the attraction of
cGMP, like cAMP, gets synthesized when olfactory receptors receive odorous input. cGMP is produced slowly and has a more sustained life than cAMP, which has implicated it in long-term cellular responses to odor stimulation, such as
Degradation
Numerous cyclic nucleotide phosphodiesterases (PDE) can degrade cGMP by hydrolyzing cGMP into 5'-GMP. PDE 5, -6 and -9 are cGMP-specific while PDE1, -2, -3, -10 and -11 can hydrolyse both cAMP and cGMP.
Phosphodiesterase inhibitors prevent the degradation of cGMP, thereby enhancing and/or prolonging its effects. For example, Sildenafil (Viagra) and similar drugs enhance the vasodilatory effects of cGMP within the corpus cavernosum by inhibiting PDE 5 (or PDE V). This is used as a treatment for erectile dysfunction. However, the drug can inhibit PDE6 in retina (albeit with less affinity than PDE5). This has been shown to result in loss of visual sensitivity but is unlikely to impair common visual tasks, except under conditions of reduced visibility when objects are already near visual threshold.[9] This effect is largely avoided by other PDE5 inhibitors, such as tadalafil.[10]
Protein kinase activation
cGMP is involved in the regulation of some protein-dependent kinases. For example, PKG (
cGMP binds to sites on the regulatory units of PKG and activates the catalytic units, enabling them to phosphorylate their substrates. Unlike with the activation of some other protein kinases, notably PKA, the PKG is activated but the catalytic and regulatory units do not disassociate.
See also
- Cyclic adenosine monophosphate (cAMP)
- 8-Bromoguanosine 3',5'-cyclic monophosphate (8-Br-cGMP)