sodium (4aR,6R,7R,7aS)-6-[6-amino-8-(methylamino)-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: 153188
• Molecular Formular: C11H14N6NaO6P
• Molecular Mass: 380.228991
• Monoisotopic Mass: 380.06101311
• SMILES: CNc1nc2c(ncnc2n1[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])O)N.[Na+]
• Canonical SMILES: CNc1nc2c(n1[C@@H]1O[C@H]3[C@H]([C@H]1O)OP(=O)(OC3)[O-])ncnc2N.[Na+]
• InChI: InChI=1S/C11H15N6O6P.Na/c1-13-11-16-5-8(12)14-3-15-9(5)17(11)10-6(18)7-4(22-10)2-21-24(19,20)23-7;/h3-4,6-7,10,18H,2H2,1H3,(H,13,16)(H,19,20)(H2,12,14,15);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1
• InChIKey: PYXGPPLPPUIPRE-MCDZGGTQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aS)-6-[6-amino-8-(methylamino)-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-(methylamino)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-Methylaminoadenosine-3′,5′-cyclic monophosphate sodium salt; 8-MA-cAMP

Database IDs

• CAS Number: 33823-18-6
• MDL Number: MFCD04113731
• PubChem SID: 162247327; 24724571
• PubChem CID: 23675377

CALCULATED PROPERTIES

• Acid pKa: 1.8356466
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -3.5683706
• LogD (pH = 7.4): -3.537801
• Log P: -3.7418633
• Molar Refractivity: 78.8349 cm^3
• Polarizability: 30.766396 Å^3
• Polar Surface Area: 169.7 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): C11H14N6O6PNa

DETAILS

Sigma Aldrich - P0747

Biochem/physiol Actions
Selective cAMP-dependent protein kinase (PKA) activator. Site selective cyclic AMP analogue with similar affinity to site B of both protein kinase A type I and II. Priming analogue which acts synergistically together with analogues showing site A preference. Together with e.g. 8-piperidino cAMP, selective stimulation of type I can be achieved.