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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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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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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...
View on PubChemRaw 3D data
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

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