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C-di-AMP (disodium)

CAT: 0804-HY-12326A-01Size: 500 µgDry Ice: YesHazardous: No
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CAT#:0804-HY-12326A-01Size:500 µg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
C-di-AMP (Cyclic diadenylate) sodium is a STING agonist, which binds to the transmembrane protein STING thereby activating the TBK3-IRF3 signaling pathway, subsequently triggering the production of type I IFN and TNF. c-di-AMP sodium is also a bacterial second messenger, which regulates cell growth, survival, and virulence, primarily within Gram-positive bacteria, and also regulates host immune response. c-di-AMP sodium acts as a potent mucosal adjuvant stimulating both humoral and cellular responses[1][2][3][4].
CAS Number
2734909-87-4
Product Name Alternative
Cyclic diadenylate (disodium) ; Cyclic-di-AMP (disodium)
UNSPSC
12352005
Hazard Statement
H302, H315, H319
Target
Bacterial; Endogenous Metabolite; STING
Type
Reference compound
Related Pathways
Anti-infection; Immunology/Inflammation; Metabolic Enzyme/Protease
Applications
COVID-19-immunoregulation
Field of Research
Inflammation/Immunology
Assay Protocol
https://www.medchemexpress.com/c-di-amp-sodium.html
Purity
99.14
Solubility
DMSO : 270 mg/mL (ultrasonic) |H2O : ≥ 50 mg/mL
Smiles
O[C@H]([C@@](OP(OC[C@](O[C@@H](N1C2=NC=NC(N)=C2N=C1)[C@@H]3O)([H])[C@@]3([H])O4)(O[Na])=O)([H])[C@](COP4(O[Na])=O)([H])O5)[C@@H]5N6C7=NC=NC(N)=C7N=C6
Molecular Formula
C20H22N10Na2O12P2
Molecular Weight
702.38
Precautions
H302, H315, H319
References & Citations
[1]Fahmi T, et al. c-di-AMP: An Essential Molecule in the Signaling Pathways that Regulate the Viability and Virulenceof Gram-Positive Bacteria. Genes (Basel) . 2017 Aug 7;8 (8) .|[2]Ning H, et al. Recombinant BCG With Bacterial Signaling Molecule Cyclic di-AMP as Endogenous AdjuvantInduces Elevated Immune Responses After Mycobacterium tuberculosis Infection. Front Immunol. 2019 Jul 3;10:1519.|[3]Ebensen T, et al. The Combination Vaccine Adjuvant System Alum/c-di-AMP Results in Quantitative and QualitativeEnhanced Immune Responses Post Immunization. Front Cell Infect Microbiol. 2019 Feb 19;9:31.|[4]Sanchez MV, et al. Intranasal delivery of influenza rNP adjuvanted with c-di-AMP induces strong humoral and cellularimmune responses and provides protection against virus challenge. PLoS One. 2014 Aug 20;9 (8) :e104824.
Shipping Conditions
Dry Ice
Storage Conditions
-80°C, protect from light, stored under nitrogen
Scientific Category
Reference compound1
Clinical Information
No Development Reported
Citation 01
BioRxiv. 2025 Apr 1:2025.03.28.646030.|Cell Death Dis. 2022 Jul 28;13 (7) :653.|J Control Release. 2025 Nov 13:389:114410.|Nature. 2025 Nov;647 (8091) :997-1004.|Sci Adv. 2025 Apr 4;11 (14) :eadt8165.|University of Michigan. 2025.|Fish Shellfish Immunol. 2025 Aug 27:167:110691.|Gut Microbes. 2022 Jan-Dec;14 (1) :2119055.|Mol Ther. 2025 Jul 16:S1525-0016 (25) 00549-0.

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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