(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinine-2-thione; triethylamine

• ChemBase ID: 106001
• Molecular Formular: C16H27N6O5PS
• Molecular Mass: 446.461541
• Monoisotopic Mass: 446.15012562
• SMILES: CCN(CC)CC.c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=S)(O2)O)O)N
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=S)(O)OC[C@H]2O[C@H]1n1cnc2c1ncnc2N.CCN(CC)CC
• InChI: 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
• InChIKey: OXIPZMKSNMRTIV-RNSTXJOVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinine-2-thione; triethylamine; (2R,4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-2,7-dihydroxy-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinine-2-thione; triethylamine
• IUPAC Traditional name: (4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinine-2-thione; triethylamine; (2R,4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-2,7-dihydroxy-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinine-2-thione; triethylamine
• Synonyms: Rp-Cyclic 3′,5′-hydrogen phosphorothioate adenosine triethylammonium salt; Rp-cAMPS triethylammonium salt hydrate; Rp-Adenosine 3′,5′-cyclic monophosphorothioate triethylammonium salt hydrate; Rp-cAMPS; ADENOSINE-3',5'-cyclic-MONOPHOSPHOROTHIOATE TRIETHYLAMMONIUM SALT RP ISOMER

Database IDs

• CAS Number: 151837-09-1(anhydrous); 73208-40-9
• MDL Number: MFCD03703495
• PubChem SID: 162089000; 24890575
• PubChem CID: 16218857

CALCULATED PROPERTIES

• Acid pKa: 1.8909222
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.8760402
• LogD (pH = 7.4): -2.8056078
• Log P: -3.0947933
• Molar Refractivity: 78.2804 cm^3
• Polarizability: 31.14115 Å^3
• Polar Surface Area: 137.77 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL
• Apperance: white solid
• Absorption Wavelength: λmax 258 nm

Safety Information

• Storage Condition: -20°C; desiccated
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98%; ≥98% (HPLC)

DETAILS

MP Biomedicals - 02195828

Rp-Isomer
Purity: >98%
A potent competitive inhibitor of cAMP-dependent protein kinase activation. It is cell permeable and resistant to cyclic nucleotide phosphodiesterases.

Sigma Aldrich - A165

Biochem/physiol Actions
Rp-Diastereomer of adenosine-3′,5′-cyclic monophosphothioate. Specific membrane-permeable inhibitor of activation by cAMP of cAMP-dependent protein kinase I and II; resistant toward cyclic nucleotide phosphodiesterases; blocks cAMP-mediated effects in numerous systems.
Caution
Extremely hygroscopic. Store desiccated.