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Cyclic GMP

CAT: 0931-TN9056-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0931-TN9056-01Size:10 mg
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CAS Number
7665-99-8
Target
Endogenous Metabolite, STING
Related Pathways
Metabolism, Immunology/Inflammation
Bioactivity
Cyclic GMP is an endogenous second messenger that initiates interferon production in response to cytoplasmic DNA. It activates the stimulator of interferon genes (STING), triggering a signaling cascade that results in the production of type I interferons and other immune mediators. The conjugate of cyclic GMP and AMP, known as Cyclic-GMP-AMP, can induce the phosphorylation and nuclear translocation of IRF3, thereby enhancing antiviral immune responses. Additionally, Cyclic GMP may activate PDE to degrade cAMP, inhibit the myocardial calcium current ICa, and regulate cardiac contractility. The derivative 8-Br-cGMP exhibits antiplatelet activity, and Cyclic GMP is used in research related to antiviral immunity and cardiovascular diseases.
Smiles
O=C1C2=C(N(C=N2)[C@H]3[C@H](O)[C@]4([C@](O3)(COP(=O)(O)O4)[H])[H])NC(N)=N1
Molecular Formula
C10H12N5O7P
Molecular Weight
345.205
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

Cgmp

3',5'-cyclic GMP is a 3',5'-cyclic purine nucleotide in which the purine nucleobase is specified as guanidine. It has a role as a mouse metabolite, a Saccharomyces cerevisiae metabolite, a plant metabolite, an Escherichia coli metabolite and a human metabolite. It is a 3',5'-cyclic purine nucleotide and a guanyl ribonucleotide. It is a conjugate acid of a 3',5'-cyclic GMP(1-).

CAS Number7665-99-8
PubChem CID135398570
IUPAC Name9-[(4aR,6R,7R,7aS)-2,7-dihydroxy-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-6-yl]-2-amino-1H-purin-6-one
Molecular FormulaC10H12N5O7P
Molecular Weight345.21
XLogP-3.4
Topological Polar Surface Area171
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count1
Heavy Atom Count23
Formal Charge0
Complexity616
SMILES
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C3N=C(NC4=O)N)O)OP(=O)(O1)O
InChI
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)/t3-,5-,6-,9-/m1/s1
InChIKey
ZOOGRGPOEVQQDX-UUOKFMHZSA-N
Chemical Structure
2D Structure
2D structure of Cgmp
CAS: 7665-99-8
CID: 135398570
Formula: C10H12N5O7P
MW: 345.21
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight345.21
XLogP3-3.4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count9
Rotatable Bond Count1
Exact Mass345.04743474
Monoisotopic Mass345.04743474
Topological Polar Surface Area171 Ų
Heavy Atom Count23
Formal Charge0
Complexity616
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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