(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-7-hydroxy-2-sulfanyl-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-one; triethylamine

• ChemBase ID: 106002
• Molecular Formular: C16H27N6O5PS
• Molecular Mass: 446.461541
• Monoisotopic Mass: 446.15012562
• SMILES: CCN(CC)CC.Nc1ncnc2c1ncn2[C@@H]1O[C@@H]2COP(=O)(S)O[C@H]2[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)(S)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-NVGWRVNNSA-N

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 93602-66-5(anhydrous); 71774-13-5
• MDL Number: MFCD01459901
• PubChem SID: 24890576; 162092880
• PubChem CID: 16218857

CALCULATED PROPERTIES

• Acid pKa: 0.96920174
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -2.230113
• LogD (pH = 7.4): -2.1170526
• Log P: -3.6860723
• Molar Refractivity: 74.2807 cm^3
• Polarizability: 30.47913 Å^3
• Polar Surface Area: 134.61 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble
• Apperance: white solid
• Optical Rotation: [α]22/D -25.43°, c = 0.99 in H2O(lit.)

Safety Information

• Storage Condition: -20°C
• 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 - 02195829

Sp-Isomer
Purity: >98%
A potent and specific activator of cAMP-dependent protein kinase. It is cell permeable and resistant to cyclic nucleotide phosphodiesterases.

Sigma Aldrich - A166

Biochem/physiol Actions
Sp-Diastereomer of adenosine 3′,5′-cyclic monophosphorothioate is a potent, membrane-permeable activator of cAMP dependent protein kinase I and II that mimics the effects of cAMP as a second messenger in numerous systems while being resistant to cyclic nucleotide phosphodiesterases; exhibits greater specificity and affinity than forskolin and cAMP analogs such as dibutyryl-cAMP.