Skip to Content
MilliporeSigma
All Photos(3)

Documents

G7504

Sigma-Aldrich

Guanosine 3′,5′-cyclic monophosphate

≥98% (HPLC), powder, intracellular mediator

Synonym(s):

cGMP, cyclic GMP

Sign Into View Organizational & Contract Pricing
All Photos(3)

About This Item

Empirical Formula (Hill Notation):
C10H12N5O7P
CAS Number:
7665-99-8
Molecular Weight:
345.21
EC Number:
231-641-6
MDL number:
MFCD00070129
UNSPSC Code:
41106305
PubChem Substance ID:
24895309
NACRES:
NA.77

product name

Guanosine 3′,5′-cyclic monophosphate, ≥98% (HPLC), powder

Quality Level

200

assay

≥98% (HPLC)

form

powder

color

white

solubility

0.2 M NaHCO3: 50 mg/mL

storage temp.

−20°C

SMILES string

NC1=NC(=O)c2ncn(C3OC4COP(O)(=O)OC4C3O)c2N1

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)

InChI key

ZOOGRGPOEVQQDX-UHFFFAOYSA-N

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 ADME Tox and Cyclic Nucleotide research. Discover more featured ADME Tox and Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

Lasse H Hansen et al.
The Journal of biological chemistry, 294(34), 12567-12578 (2019-06-13)
Atrial natriuretic peptide (ANP) is a peptide hormone that in response to atrial stretch is secreted from atrial myocytes into the circulation, where it stimulates vasodilatation and natriuresis. ANP is an important biomarker of heart failure where low plasma concentrations
Jeanette Erdmann et al.
Nature, 504(7480), 432-436 (2013-11-12)
Myocardial infarction, a leading cause of death in the Western world, usually occurs when the fibrous cap overlying an atherosclerotic plaque in a coronary artery ruptures. The resulting exposure of blood to the atherosclerotic material then triggers thrombus formation, which
Juliane W Schott et al.
Molecular therapy. Methods & clinical development, 14, 134-147 (2019-07-25)
Ex vivo retroviral gene transfer into CD34+ hematopoietic stem and progenitor cells (HSPCs) has demonstrated remarkable clinical success in gene therapy for monogenic hematopoietic disorders. However, little attention has been paid to enhancement of culture and transduction conditions to achieve reliable
Ko-Hsin Chin et al.
Acta crystallographica. Section D, Biological crystallography, 69(Pt 3), 352-366 (2013-03-23)
The mammalian ER protein STING (stimulator of interferon genes; also known as MITA, ERIS, MPYS or TMEM173) is an adaptor protein that links the detection of cytosolic dsDNA to the activation of TANK-binding kinase 1 (TBK1) and its downstream transcription
Minsuk Kim et al.
Nature medicine, 19(5), 567-575 (2013-04-02)
Glucagon-like peptide-1 receptor (GLP-1R) agonists exert antihypertensive actions through incompletely understood mechanisms. Here we demonstrate that cardiac Glp1r expression is localized to cardiac atria and that GLP-1R activation promotes the secretion of atrial natriuretic peptide (ANP) and a reduction of
View All Related Papers

Articles

Discover Bioactive Molecules for Nucleotides

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

Discover Bioactive Small Molecules for ADME/Tox

Discover Bioactive Small Molecules for ADME/Tox

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service