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G7504

Sigma-Aldrich

Guanosine 3′,5′-cyclic monophosphate

≥98% (HPLC), powder, intracellular mediator

Synonym(s):

cGMP, cyclic GMP

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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

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

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Personal Protective Equipment

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’.

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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
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
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
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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