cAMPS-Rp, triethylammonium salt - ≥98%(HPLC) , CAS No.151837-09-1

CAS: 151837-09-1 Cat. No.: C286882 Molecular Weight: 446.46

GRADE & PURITY ≥98%(HPLC)

Synonyms

(R)-Adenosine, cyclic 3',5'-(hydrogenphosphorothioate) triethylammonium

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

(R)-Adenosine, cyclic 3', 5'-(hydrogenphosphorothioate) triethylammonium

Specifications & Purity

≥98%(HPLC)

Biochemical and Physiological Mechanisms

Cell-permeable cAMP analog; acts as a competitive antagonist of cAMP-induced activation of PKA (IC50= 11 - 16μM) by interacting with cAMP binding sites on the regulatory subunits. Resistant to hydrolysis by phosphodiesterases.

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

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

Purity

≥98%(HPLC)

Names and Identifiers

• Canonical Smiles: CCN(CC)CC.C1C2C(C(C(O2)N3C=NC4=C(N=CN=C43)N)O)OP(=S)(O1)O
• IUPAC Name: (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2-hydroxy-2-sulfanylidene-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-ol;N,N-diethylethanamine
• InChIKey: OXIPZMKSNMRTIV-NVGWRVNNSA-N
• INCHI: 1S/C10H12N5O5PS.C6H15N/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(19-10)1-18-21(17,22)20-7;1-4-7(5-2)6-3/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13);4-6H2,1-3H3/t4-,6-,7-,10-,21?;/m1./s1
• Isomeric SMILES: CCN(CC)CC.C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=S)(O1)O
• Molecular Weight: 446.46
• Reaxy-Rn: 6466280
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=6466280&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Nucleosides, nucleotides, and analogues
    • Class Nucleoside and nucleotide analogues
      • Subclass 3',5'-cyclic purine nucleoside phosphorothioates

• Kingdom: Organic compounds
• Superclass: Nucleosides, nucleotides, and analogues
• Class: Nucleoside and nucleotide analogues
• Subclass: 3',5'-cyclic purine nucleoside phosphorothioates
• Intermediate Tree Nodes: Not available
• Direct Parent: 3',5'-cyclic purine nucleoside phosphorothioates
• Alternative Parents: Glycosylamines 6-aminopurines Aminopyrimidines and derivatives Thiophosphoric acid esters N-substituted imidazoles Monosaccharides Imidolactams Quaternary ammonium salts Oxolanes Heteroaromatic compounds Trialkylamines Secondary alcohols Oxacyclic compounds Azacyclic compounds Hydrocarbon derivatives Organic oxides Organic zwitterions Primary amines
• Molecular Framework: Not available
• Substituents: 3',5'-cyclic purine nucleoside phosphorothioate - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Imidazopyrimidine - Purine - Aminopyrimidine - Monosaccharide - N-substituted imidazole - Thiophosphoric acid ester - Imidolactam - Organic thiophosphoric acid or derivatives - Pyrimidine - Azole - Imidazole - Heteroaromatic compound - Oxolane - Quaternary ammonium salt - Tertiary aliphatic amine - Secondary alcohol - Organoheterocyclic compound - Azacycle - Oxacycle - Organic oxygen compound - Organooxygen compound - Organonitrogen compound - Amine - Alcohol - Hydrocarbon derivative - Organic oxide - Organic nitrogen compound - Primary amine - Organic zwitterion - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as 3',5'-cyclic purine nucleoside phosphorothioates. These are 3',5'-cyclic purine nucleoside phosphate analogues, where a phosphate oxygen has been exchanged for sulphur generating a chiral phosphorothioate. In 3',5'-cyclic nucleoside phosphorothioate, the oxygen atoms at the 3'- and 5'-positions of the ribose are part of the phosphorothioate group.
• External Descriptors: Not available

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Solvent:water, Max Conc. mg/mL: 44.65, Max Conc. mM: 100
• Molecular Weight: 446.500 g/mol
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 11
• Rotatable Bond Count: 4
• Exact Mass: 446.15 Da
• Monoisotopic Mass: 446.15 Da
• Topological Polar Surface Area: 173.000 Ų
• Heavy Atom Count: 29
• Formal Charge: 0
• Complexity: 528.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 4
• 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: 2

XLogP3