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2'2'-cGAMP (sodium salt)

CAT: 0931-T35654-01Size: 500 µgDry Ice: NoHazardous: No
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CAT#:0931-T35654-01Size:500 µg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
1465774-27-9
Target
Others, Endogenous Metabolite, STING, IFNAR
Related Pathways
Others, Immunology/Inflammation, Metabolism
Bioactivity
2'2'-cGAMP is a synthetic dinucleotide (CDN) that contains non-canonical 2'5'-phosphodiester bonds. It binds to the adapter protein stimulator of interferon genes , which is a component of the innate immune response that activates the type I interferon pathway when bound to cyclic dinucleotides. 2'2-cGAMP shows weaker binding to STING than 2'3'-cGAMP but binds more strongly than 3'3'-cGAMP , cyclic di-GMP , or 3'2'-cGAMP, which bind in the micromolar range (Kds = 1.04, 1.21, or 1.61 μM, respectively) . Despite weaker binding, 2'2'-cGAMP induces IFN-β production in the same concentration range as 2'3'-cGAMP (EC50s = 15.8 and 19.4 nM, respectively, in L929 cells) .
Smiles
[H][C@]12COP(O)(=O)O[C@@]3([H])[C@@H](O[C@]([H])(COP(O)(=O)O[C@@]([H])([C@@H](O1)n1cnc4c(N)ncnc14)C2O)[C@H]3O)n1cnc2c1[nH]c(N)nc2=O
Molecular Formula
C20H24N10O13P2
Molecular Weight
674.417
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

2'2'-cGAMP (sodium salt)
CAS Number1465774-27-9
PubChem CID163335213
IUPAC Namedisodium;2-amino-9-[(1R,6R,8R,9R,14R,16R)-16-(6-aminopurin-9-yl)-17,18-dihydroxy-3,11-dioxido-3,11-dioxo-2,4,7,10,12,15-hexaoxa-3lambda5,11lambda5-diphosphatricyclo[12.2.1.16,9]octadecan-8-yl]-1H-purin-6-one
Molecular FormulaC20H22N10Na2O13P2
Molecular Weight718.4
Topological Polar Surface Area331
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count19
Rotatable Bond Count2
Heavy Atom Count47
Formal Charge0
Complexity1290
SMILES
C1[C@@H]2C([C@H]([C@@H](O2)N3C=NC4=C3N=C(NC4=O)N)OP(=O)(OC[C@@H]5C([C@H]([C@@H](O5)N6C=NC7=C(N=CN=C76)N)OP(=O)(O1)[O-])O)[O-])O.[Na+].[Na+]
InChI
InChI=1S/C20H24N10O13P2.2Na/c21-14-8-15(24-3-23-14)29(4-25-8)18-12-10(31)6(40-18)1-38-45(36,37)43-13-11(32)7(2-39-44(34,35)42-12)41-19(13)30-5-26-9-16(30)27-20(22)28-17(9)33;;/h3-7,10-13,18-19,31-32H,1-2H2,(H,34,35)(H,36,37)(H2,21,23,24)(H3,22,27,28,33);;/q;2*+1/p-2/t6-,7-,10?,11?,12-,13-,18-,19-;;/m1../s1
InChIKey
SCPBVQDKYSCDAE-RENITANYSA-L
Chemical Structure
2D Structure
2D structure of 2'2'-cGAMP (sodium salt)
CAS: 1465774-27-9
CID: 163335213
Formula: C20H22N10Na2O13P2
MW: 718.4
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight718.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count19
Rotatable Bond Count2
Exact Mass718.06384335
Monoisotopic Mass718.06384335
Topological Polar Surface Area331 Ų
Heavy Atom Count47
Formal Charge0
Complexity1290
Isotope Atom Count0
Defined Atom Stereocenter Count6
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count3
Compound Is CanonicalizedYes

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