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

• ChemBase ID: 154234
• Molecular Formular: C15H20N6NaO6P
• Molecular Mass: 434.319431
• Monoisotopic Mass: 434.1079633
• SMILES: c1nc(c2c(n1)n(c(n2)N1CCCCC1)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])O)N.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1c(nc2c1ncnc2N)N1CCCCC1.[Na+]
• InChI: InChI=1S/C15H21N6O6P.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(26-14)6-25-28(23,24)27-11;/h7-8,10-11,14,22H,1-6H2,(H,23,24)(H2,16,17,18);/q;+1/p-1/t8-,10-,11-,14-;/m1./s1
• InChIKey: FNCWZMQKRRKCEF-ZBMQJGODSA-M

NAMES AND DATABASE IDS

Names

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

Database IDs

• CAS Number: 31357-06-9
• MDL Number: MFCD06798348
• PubChem SID: 24724572; 162248373
• PubChem CID: 23675378

CALCULATED PROPERTIES

• Acid pKa: 1.8325837
• H Acceptors: 9
• H Donor: 2
• LogD (pH = 5.5): -2.0824
• LogD (pH = 7.4): -2.052164
• Log P: -2.2547917
• Molar Refractivity: 95.2117 cm^3
• Polarizability: 37.30997 Å^3
• Polar Surface Area: 160.91 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: freely soluble
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -70°C

Product Information

• Purity: ≥98% (HPLC)
• Packaging: pkg of 10 μmol
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C15H20N6O6PNa

DETAILS

Sigma Aldrich - P0872

Biochem/physiol Actions
Selective cAMP-dependent protein kinase (PKA) activator. Site selective cyclic AMP analog with high selectivity for site A of protein kinase A type I and for site B of type II. Acts synergistically together with analogs having opposite site-selectivity.