c-di-AMP - Moligand™, ≥98% , CAS No.54447-84-6

CAS: 54447-84-6 Cat. No.: A303948 Formula: C₂₀H₂₄N₁₀O₁₂P₂ Molecular Weight: 658.41

GRADE & PURITY Moligand™, ≥98%

Synonyms

AKOS030526840 | SCHEMBL18700333 | cyclic di-3',5'-adenylic acid | BDBM50509429 | Cyclic-di-AMP | ]tetraoxadiphosphacyclododecine-3,5,10,12-tetrol 5,12-dioxide | bis-(3'-5')-cyclic dimeric adenosine monophosphate | AKOS016842810 | Cyclic diadenylate | (2R,

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

AKOS030526840 | SCHEMBL18700333 | cyclic di-3',5'-adenylic acid | BDBM50509429 | Cyclic-di-AMP | ]tetraoxadiphosphacyclododecine-3,5,10,12-tetrol 5,12-dioxide | bis-(3'-5')-cyclic dimeric adenosine monophosphate | AKOS016842810 | Cyclic diadenylate | (2R,

Specifications & Purity

Moligand™, ≥98%

Storage

Protected from light,Store at -20°C,Argon charged

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Purity

≥98%

Names and Identifiers

Canonical Smiles

C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=O)(OCC5C(C(C(O5)N6C=NC7=C(N=CN=C76)N)O)OP(=O)(O1)O)O

IUPAC Name

(1S,6R,8R,9R,10S,15R,17R,18R)-8,17-bis(6-aminopurin-9-yl)-3,12-dihydroxy-3,12-dioxo-2,4,7,11,13,16-hexaoxa-3λ5,12λ5-diphosphatricyclo[13.3.0.06,10]octadecane-9,18-diol

InChIKey

PDXMFTWFFKBFIN-XPWFQUROSA-N

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

Isomeric 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

Alternate CAS

2734909-87-4

Molecular Weight

658.41

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class (3'->5')-dinucleotides and analogues
      • Subclass (3'->5')-cyclic dinucleotides and analogues

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: (3'->5')-dinucleotides and analogues
• Subclass: (3'->5')-cyclic dinucleotides and analogues
• Intermediate Tree Nodes: Not available
• Direct Parent: (3'->5')-cyclic dinucleotides and analogues
• Alternative Parents: Purine ribonucleoside 3',5'-bisphosphates Pentose phosphates Glycosylamines 6-aminopurines Monosaccharide phosphates Aminopyrimidines and derivatives Imidolactams N-substituted imidazoles Organic phosphoric acids and derivatives Tetrahydrofurans Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Polyols Azacyclic compounds Hydrocarbon derivatives Primary amines Organopnictogen compounds Organic oxides
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: (3'->5')-cyclic dinucleotide or analogue - Purine ribonucleoside 3',5'-bisphosphate - Purine ribonucleoside bisphosphate - Pentose phosphate - Pentose-5-phosphate - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Monosaccharide phosphate - Imidazopyrimidine - Purine - Aminopyrimidine - Monosaccharide - N-substituted imidazole - Organic phosphoric acid derivative - Imidolactam - Pyrimidine - Tetrahydrofuran - Azole - Imidazole - Heteroaromatic compound - Secondary alcohol - Organoheterocyclic compound - Oxacycle - Azacycle - Polyol - Organooxygen compound - Organonitrogen compound - Amine - Alcohol - Organic nitrogen compound - Organic oxygen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Primary amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as (3'->5')-cyclic dinucleotides and analogues. These are cyclic compounds consisting of two ribose moieties connected by two 5',3'-phosphodiester bonds to form a cycle. Each ribose unit is N-linked to a nucleic base or an analogue thereof. Some natural (3'->5')-cyclic dinucleotides include c-di-AMP. Synthetic derivatives are generally more elaborated molecules in which one or the two nucleobase moieties, and/or sugar residues, and/or phosphodiester linkers have been modified.
• External Descriptors: adenyl ribonucleotide - cyclic purine dinucleotide

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

TMEM173 Tchem Stimulator of interferon genes protein (3 Activities)

Discover Target: TMEM173

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: light sensitive
• Molecular Weight: 658.400 g/mol
• XLogP3: -5.100
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 20
• Rotatable Bond Count: 2
• Exact Mass: 658.105 Da
• Monoisotopic Mass: 658.105 Da
• Topological Polar Surface Area: 310.000 Ų
• Heavy Atom Count: 44
• Formal Charge: 0
• Complexity: 1080.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 8
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1