CAS 54447-84-6

Cyclic-di-AMP

Description:

Cyclic di-AMP (c-di-AMP) is a second messenger molecule that plays a crucial role in bacterial signaling and regulation. It is a cyclic dinucleotide composed of two adenosine monophosphate (AMP) units linked by phosphodiester bonds, forming a cyclic structure. This molecule is involved in various cellular processes, including the regulation of cell wall homeostasis, stress responses, and the modulation of virulence factors in bacteria. C-di-AMP is synthesized by specific enzymes known as diadenylate cyclases and is degraded by phosphodiesterases. Its presence in bacterial cells can influence the activity of various downstream effectors, including transcription factors and other signaling proteins. The molecule is also of interest in the field of immunology, as it can act as a pathogen-associated molecular pattern (PAMP) that triggers immune responses in host organisms. Due to its significant role in bacterial physiology and potential implications in human health, c-di-AMP has garnered attention for its potential as a target for antibiotic development and therapeutic interventions.

Formula: C₂₀H₂₄N₁₀O₁₂P₂

InChI: InChI=1S/C20H24N10O12P2/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)/t7-,8-,11-,12-,13-,14-,19-,20-/m1/s1

InChI key: InChIKey=PDXMFTWFFKBFIN-XPWFQUROSA-N

SMILES: O[C@H]1[C@H](N2C=3C(N=C2)=C(N)N=CN3)O[C@]4([C@]1(OP(=O)(O)OC[C@@]5([C@@](OP(=O)(O)OC4)([C@@H](O)[C@@H](O5)N6C=7C(N=C6)=C(N)N=CN7)[H])[H])[H])[H]

Synonyms:

• 3′-Adenylic acid, adenylyl-(3′→5′)-, cyclic nucleotide
• c-Di-AMP
• 2H,7H-Difuro[3,2-d:3′,2′-j][1,3,7,9,2,8]tetraoxadiphosphacyclododecin, 3′-adenylic acid deriv.
• Adenylic acid, cyclic ester
• Cyclic-di-AMP
• Cyclic di-3',5'-adenylate
• di-cAMP
• c-Di-AMP(Cyclic-Di-AMP) ammonium salt
• di-AMP
• c-di-AMP (Cyclic diadenylate
• Cyclic diadenylate

c-di-AMP

CAS: 54447-84-6

Complexity 1080
Compound Is Canonicalized Yes
Covalently-Bonded Unit Count 1
Defined Atom Stereocenter Count 8
Defined Bond Stereocenter Count 0
Exact Mass 658.105g/mol
Formal Charge 0
Heavy Atom Count 44
Hydrogen Bond Acceptor Count 20
Hydrogen Bond Donor Count 6
Isotope Atom Count 0
Molecular Weight 658.418g/mol
Monoisotopic Mass 658.105g/mol
Rotatable Bond Count 2
Topological Polar Surface Area 310A^2
Undefined Atom Stereocenter Count 0
Undefined Bond Stereocenter Count 0
XLogP3 -5.1

Formula: C₂₀H₂₄N₁₀O₁₂P₂

Purity: 99%

Molecular weight: 658.4119

Ref: IN-DA00D9YA

Cyclic di-AMP

Controlled Product

CAS: 54447-84-6

Formula: C₂₀H₂₄N₁₀O₁₂P₂

Color and Shape: Neat

Molecular weight: 658.412

Ref: TR-C987350

Cyclic di-adenosine monophosphate sodium salt

CAS: 54447-84-6

Cyclic di-adenosine monophosphate sodium salt (c-di-AMP) is a cyclic nucleotide that is structurally similar to its natural counterpart, Adenosine 5'-triphosphate. It binds to the Toll-like receptor 4 (TLR4) and blocks the activation of TLR4 by lipopolysaccharide, thereby inhibiting the downstream inflammatory response. c-di-AMP also inhibits the production of proinflammatory cytokines such as TNFα, IL1β, and IL6 in vitro. c-di-AMP has shown anti-inflammatory properties in vivo and can be used for the treatment of infectious diseases.

Formula: C₂₀H₂₄N₁₀O₁₂P₂·xNa

Purity: Min. 95%

Molecular weight: 658.41 g/mol

Ref: 3D-NC64061

c-di-AMP

CAS: 54447-84-6

c-di-AMP (Cyclic diadenylate) is a STING agonist. It binds to the transmembrane protein STING thereby activating the TBK3-IRF3 signaling pathway.

Formula: C₂₀H₂₄N₁₀O₁₂P₂

Purity: 98%

Color and Shape: Solid

Molecular weight: 658.41

Ref: TM-T10642