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C-di-AMP disodium

CAT: 0931-T73873-01Size: 500 µgDry Ice: NoHazardous: No
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CAT#:0931-T73873-01Size:500 µg
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CAS Number
2734909-87-4
Target
Others, Endogenous Metabolite, STING, Antibacterial
Related Pathways
Microbiology/Virology, Metabolism, Others, Immunology/Inflammation
Bioactivity
Cyclic diadenylate (c-di-AMP) sodium functions as a STING agonist by binding to the STING transmembrane protein, thus activating the TBK3-IRF3 signaling pathway. This activation prompts the production of type I IFN and TNF. Additionally, c-di-AMP sodium serves as a bacterial second messenger in Gram-positive bacteria, where it plays crucial roles in regulating cell growth, survival, and virulence, as well as the host immune response. It also acts as a potent mucosal adjuvant by stimulating both humoral and cellular responses [1] [2] [3] [4].
Smiles
[Na+].[Na+].[H][C@@]12COP([O-])(=O)O[C@@]3([H])[C@@H](O)[C@@H](O[C@]3([H])COP([O-])(=O)O[C@@]1([H])[C@@H](O)[C@@H](O2)n1cnc2c(N)ncnc12)n1cnc2c(N)ncnc12
Molecular Formula
C20H22N10Na2O12P2
Molecular Weight
702.38
Shipping Conditions
Ice Packs
Storage Temperature
-20°C

Chemical Information

c-di-AMP disodium
CAS Number2734909-87-4
PubChem CID122714672
IUPAC Namedisodium;(1S,6R,8R,9R,10S,15R,17R,18R)-8,17-bis(6-aminopurin-9-yl)-3,12-dioxido-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3lambda5,12lambda5-diphosphatricyclo[13.3.0.06,10]octadecane-9,18-diol
Molecular FormulaC20H22N10Na2O12P2
Molecular Weight702.4
Topological Polar Surface Area315
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count20
Rotatable Bond Count2
Heavy Atom Count46
Formal Charge0
Complexity1070
SMILES
C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(OC[C@@H]5[C@H]([C@H]([C@@H](O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)[O-])[O-].[Na+].[Na+]
InChI
InChI=1S/C20H24N10O12P2.2Na/c21-15-9-17(25-3-23-15)29(5-27-9)19-11(31)13-7(39-19)1-37-43(33,34)42-14-8(2-38-44(35,36)41-13)40-20(12(14)32)30-6-28-10-16(22)24-4-26-18(10)30;;/h3-8,11-14,19-20,31-32H,1-2H2,(H,33,34)(H,35,36)(H2,21,23,25)(H2,22,24,26);;/q;2*+1/p-2/t7-,8-,11-,12-,13-,14-,19-,20-;;/m1../s1
InChIKey
IXWPEIRAKLMJQW-VEQUCWRQSA-L
Chemical Structure
2D Structure
2D structure of c-di-AMP disodium
CAS: 2734909-87-4
CID: 122714672
Formula: C20H22N10Na2O12P2
MW: 702.4
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight702.4
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count20
Rotatable Bond Count2
Exact Mass702.06892873
Monoisotopic Mass702.06892873
Topological Polar Surface Area315 Ų
Heavy Atom Count46
Formal Charge0
Complexity1070
Isotope Atom Count0
Defined Atom Stereocenter Count8
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count3
Compound Is CanonicalizedYes