(S)-Adenosine, cyclic 3′,5′-(hydrogenphosphorothioate) triethylammonium - ≥98% , CAS No.71774-13-5

CAS: 71774-13-5 Cat. No.: A339988 Molecular Weight: 345.27

GRADE & PURITY ≥98%

Synonyms

(RP)-Camps | Rp-Adenosine 3',5'-cyclic Monophosphorothioate, Sodium Salt | p-Adenosine 3',5'-cyclic phosphorothiate | SCHEMBL22370431 | HY-100530A | RP-cAMPS | RP-Camp-S | AKOS040749365 | GTPL10392 | (Rp)-adenosine-3',5'-cyclic monophosphorothioate | Aden

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

(S)-Adenosine, cyclic 3',5'-(hydrogenphosphorothioate) triethylammonium is an activator of cAMP-dependent protein kinase (PKA) (cAMP agonist). Considerably higher resistance against cyclic nucleotide-dependent phosphodiesterases as compared to N6,O2'-dibutyryladenosine 3',5'-cyclic monophosphate (dibutyryl-cAMP) or 8-bromoadenosine-3',5'-cyclic monophosphate (8-Br-cAMP). There are no metabolic side effects and it is membrane permeable in many biological systems. Also suggested as an activator of Epac (cAMP-regulated guanine nucleotide exchange factor).

Specifications

Synonyms

(RP)-Camps | Rp-Adenosine 3', 5'-cyclic Monophosphorothioate, Sodium Salt | p-Adenosine 3', 5'-cyclic phosphorothiate | SCHEMBL22370431 | HY-100530A | RP-cAMPS | RP-Camp-S | AKOS040749365 | GTPL10392 | (Rp)-adenosine-3', 5'-cyclic monophosphorothioate | Aden

Specifications & Purity

≥98%

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

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

Purity

≥98%

Names and Identifiers

• Canonical Smiles: 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
• InChIKey: SMPNJFHAPJOHPP-JOILOJCLSA-N
• INCHI: 1S/C10H12N5O5PS/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/h2-4,6-7,10,16H,1H2,(H,17,22)(H2,11,12,13)/t4-,6-,7-,10-,21?/m1/s1
• Isomeric SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)N3C=NC4=C(N=CN=C43)N)O)OP(=S)(O1)O
• RTECS: AU7358160
• Molecular Weight: 345.27
• Reaxy-Rn: 1039458
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=1039458&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 Thiophosphate diesters Aminopyrimidines and derivatives N-substituted imidazoles Monosaccharides Imidolactams Oxolanes Heteroaromatic compounds Secondary alcohols Oxacyclic compounds Azacyclic compounds Primary amines Hydrocarbon derivatives
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: 3',5'-cyclic purine nucleoside phosphorothioate - Glycosyl compound - N-glycosyl compound - 6-aminopurine - Imidazopyrimidine - Purine - Aminopyrimidine - Thiophosphate diester - Monosaccharide - N-substituted imidazole - Thiophosphoric acid ester - Pyrimidine - Organic thiophosphoric acid or derivatives - Imidolactam - Azole - Oxolane - Heteroaromatic compound - Imidazole - Secondary alcohol - Organoheterocyclic compound - Azacycle - Oxacycle - Primary amine - Organic nitrogen compound - Alcohol - Hydrocarbon derivative - Amine - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - 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

Chemical and Physical Properties

• Solubility: Soluble in water (100 mM).
• Specific Rotation[α]: α22/D -25.43°, c = 0.99 in water (lit.)
• Molecular Weight: 345.270 g/mol
• XLogP3: -0.800
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 1
• Exact Mass: 345.03 Da
• Monoisotopic Mass: 345.03 Da
• Topological Polar Surface Area: 170.000 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 502.000
• 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: 1