sodium (2R,4aR,6R,7R,7aS)-6-[6-amino-8-(piperidin-1-yl)-9H-purin-9-yl]-7-hydroxy-2-sulfanylidene-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

• ChemBase ID: 155672
• Molecular Formular: C15H20N6NaO5PS
• Molecular Mass: 450.385031
• Monoisotopic Mass: 450.08511968
• SMILES: c1nc(c2c(n1)n(c(n2)N1CCCCC1)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=S)(O2)[O-])O)N.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=S)([O-])OC[C@H]2O[C@H]1n1c(nc2c1ncnc2N)N1CCCCC1.[Na+]
• InChI: InChI=1S/C15H21N6O5PS.Na/c16-12-9-13(18-7-17-12)21(15(19-9)20-4-2-1-3-5-20)14-10(22)11-8(25-14)6-24-27(23,28)26-11;/h7-8,10-11,14,22H,1-6H2,(H,23,28)(H2,16,17,18);/q;+1/p-1/t8-,10-,11-,14-,27-;/m1./s1
• InChIKey: ILHHHOJPVCBSBI-RYTXRTGRSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,4aR,6R,7R,7aS)-6-[6-amino-8-(piperidin-1-yl)-9H-purin-9-yl]-7-hydroxy-2-sulfanylidene-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• IUPAC Traditional name: sodium (2R,4aR,6R,7R,7aS)-6-[6-amino-8-(piperidin-1-yl)purin-9-yl]-7-hydroxy-2-sulfanylidene-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• Synonyms: 8-Piperidinoadenosine-3′,5′-cyclic monophosphorothioate, Rp-isomer sodium salt; Rp-8-PIP-cAMPS

Database IDs

• MDL Number: MFCD04037244
• PubChem SID: 162249810
• PubChem CID: 44755139

CALCULATED PROPERTIES

• Acid pKa: 1.883113
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.1899925
• LogD (pH = 7.4): -1.16226
• Log P: -1.3308475
• Molar Refractivity: 103.2026 cm^3
• Polarizability: 40.53638 Å^3
• Polar Surface Area: 143.84 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• 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% (HPLC)
• Mol. Weight: apparent mol wt 457.40
• Empirical Formula (Hill Notation): C15H20N6O5PSNa

DETAILS

Sigma Aldrich - P5865

Biochem/physiol Actions
Site-selective, lipophilic analogue of the phosphodiesterase-stable protein kinase A inhibitor Rp-cAMPS (Prod. No. A-165).