Rp-Adenosine 3′,5′-cyclic Monophosphorothioate, Sodium Salt - Moligand™ , Inhibitor of protein kinase A, CAS No.73208-40-9, Inhibitor of protein kinase A

CAS: 73208-40-9 Cat. No.: R334410 Molecular Weight: 367.3

GRADE & PURITY Moligand™

Synonyms

RP-CAMPS

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

Rp-Adenosine 3′,5′-cyclic Monophosphorothioate, Sodium Salt (Rp-cAMP), a membrane permeable compound, is shown to be an an inhibitor of PKA (cAMP-dependent). This compound displays a capacity to inhibit dbcAMP- and Sp-cAMPS (sc -201571)-induced stimulation of bone resorption in mice. Furthermore, due to its effects on cAMP, Rp-cAMP can also inhibit cAMP mediated cell growth of certain cells. Other effects of PKA activation inhibition noted include a decrease in Glukagon-induced glycogenolysis in hepatocytes isolated from fed rats.

Specifications

Synonyms

RP-CAMPS

Specifications & Purity

Moligand™

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.

Grade

Moligand™

Action Type

INHIBITOR

Mechanism of action

Inhibitor of protein kinase A

Product Properties

• Ki Data: PKA: Ki= 11 μM

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: 367.3
• Reaxy-Rn: 35350399
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=35350399&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

Associated Targets(Human)

PRKAR1A Tbio cAMP-dependent protein kinase type I-alpha regulatory subunit (0 Activities)

Discover Target: PRKAR1A

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

PRKAR2A Tchem cAMP-dependent protein kinase type II-alpha regulatory subunit (0 Activities)

Discover Target: PRKAR2A

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

PRKACB Tchem cAMP-dependent protein kinase catalytic subunit beta (0 Activities)

Discover Target: PRKACB

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

PRKACG Tchem cAMP-dependent protein kinase catalytic subunit gamma (0 Activities)

Discover Target: PRKACG

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

PRKAR1B Tbio cAMP-dependent protein kinase type I-beta regulatory subunit (0 Activities)

Discover Target: PRKAR1B

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

PRKAR2B Tchem cAMP-dependent protein kinase type II-beta regulatory subunit (0 Activities)

Discover Target: PRKAR2B

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

PRKACA Tchem cAMP-dependent protein kinase catalytic subunit alpha (0 Activities)

Discover Target: PRKACA

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

Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water, DMSO, methanol, and aqueous buffers.
• 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