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G6129

Sigma-Aldrich

Guanosine 3′,5′-cyclic monophosphate sodium salt

≥99% (HPLC), powder

Synonym(s):

3′,5′-Cyclic GMP monosodium salt, 3′,5′-cGMP-Na, Guanosine 3′,5′-cyclophosphate monosodium salt, cGMP, cyclic GMP

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About This Item

Empirical Formula (Hill Notation):
C10H11N5NaO7P
CAS Number:
40732-48-7
Molecular Weight:
367.19
Beilstein/REAXYS Number:
6467425
EC Number:
255-056-0
MDL number:
MFCD00038424
UNSPSC Code:
41106305
PubChem Substance ID:
24895245
NACRES:
NA.77

assay

≥99% (HPLC)

form

powder

color

white

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

[Na+].NC1=Nc2c(ncn2[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3O)C(=O)N1

InChI

1S/C10H12N5O7P.Na/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);/q;+1/p-1/t3-,5-,6-,9-;/m1./s1

InChI key

KMPIYXNEROUNOG-GWTDSMLYSA-M

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Biochem/physiol Actions

An important second messenger, cGMP is a major intracellular mediator of extracellular signals such as nitric oxide and natriuretic peptides. Cyclic GMP interacts with three types of intracellular receptor proteins: cGMP-dependent protein kinases, cGMP-regulated channels, and cGMP-regulated cyclic nucleotide phosphodiesterases. A primary action of elevated cGMP levels in vivo is the stimulation of cGMP-dependent protein kinase (PKG).

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Phosphodiesterases and PKA & PKG pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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C Picco et al.
The Journal of physiology, 460, 741-758 (1993-01-01)
1. The permeability of the channel activated by guanosine 3',5'-cyclic monophosphate (cGMP) to many organic monovalent cations was determined by recording macroscopic currents in excised inside-out patches of plasma membrane from isolated retinal rod outer segments of the tiger salamander.
G Colamartino et al.
The Journal of physiology, 440, 189-206 (1991-01-01)
1. Blockage and permeation of divalent cations through channels activated by guanosine 3',5'-cyclic monophosphate (cyclic GMP) were studied in membrane patches excised from retinal rods of the tiger salamander Ambystoma tigrinum by rapidly changing the ionic medium bathing the intracellular
Katja S Kroker et al.
Neurobiology of aging, 35(9), 2072-2078 (2014-04-22)
The cyclic nucleotide cGMP is an important intracellular messenger for synaptic plasticity and memory function in rodents. Therefore, inhibition of cGMP degrading phosphodiesterases, like PDE9A, has gained interest as potential target for treatment of cognition deficits in indications like Alzheimer's
You-Lin Tain et al.
Biology of reproduction, 92(1), 7-7 (2014-11-15)
Nitric oxide (NO) deficiency induced by the NO synthase (NOS) inhibitor N(G)-nitro-L-arginine-methyl ester (L-NAME) resulted in hypertension. L-citrulline (CIT) can be converted to L-arginine to generate NO. We examined whether maternal CIT supplementation can prevent L-NAME-induced programmed hypertension. Pregnant Sprague-Dawley
Milton Packer et al.
Circulation, 131(1), 54-61 (2014-11-19)
Clinical trials in heart failure have focused on the improvement in symptoms or decreases in the risk of death and other cardiovascular events. Little is known about the effect of drugs on the risk of clinical deterioration in surviving patients.
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