All Photos(3)

G7504

Sigma-Aldrich

Guanosine 3′,5′-cyclic monophosphate

≥98% (HPLC), powder

Synonym(s):
cGMP, cyclic GMP
Empirical Formula (Hill Notation):
C10H12N5O7P
CAS Number:
Molecular Weight:
345.21
EC Number:
MDL number:
PubChem Substance ID:

Quality Level

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

Packaging

5 mg in glass bottle
25, 100 mg in poly bottle

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.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G7504.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

pictograms

Exclamation mark

signalword

Warning

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK Germany

WGK 3

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

Certificate of Analysis

Certificate of Origin

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...
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...
Raquel Maeso-Díaz et al.
Aging and disease, 10(4), 684-698 (2019-08-24)
Advanced chronic liver disease (aCLD) represents a major public health concern. aCLD is more prevalent and severe in the elderly, carrying a higher risk of decompensation. We aimed at understanding how aging may impact on the pathophysiology of aCLD in...
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...
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...

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Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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