sodium (4aR,6R,7R,7aS)-6-(6-benzamido-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: 153674
• Molecular Formular: C17H15N5NaO7P
• Molecular Mass: 455.293831
• Monoisotopic Mass: 455.06067876
• SMILES: c1ccc(cc1)C(=O)Nc1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])O.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1cnc2c1ncnc2NC(=O)c1ccccc1.[Na+]
• InChI: InChI=1S/C17H16N5O7P.Na/c23-12-13-10(6-27-30(25,26)29-13)28-17(12)22-8-20-11-14(18-7-19-15(11)22)21-16(24)9-4-2-1-3-5-9;/h1-5,7-8,10,12-13,17,23H,6H2,(H,25,26)(H,18,19,21,24);/q;+1/p-1/t10-,12-,13-,17-;/m1./s1
• InChIKey: SPYGSKQRPXISIB-FKVBDRBCSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aS)-6-(6-benzamido-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-benzamidopurin-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: N6-Benzoyladenosine-3′,5′-cyclic monophosphate sodium salt; 6-Bnz-cAMP sodium salt

Database IDs

• CAS Number: 30275-80-0(freeacid)
• MDL Number: MFCD01074967
• PubChem SID: 24724421; 162247813
• PubChem CID: 23672707

CALCULATED PROPERTIES

• Acid pKa: 1.7361069
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.7527255
• LogD (pH = 7.4): -1.8013359
• Log P: -0.34567618
• Molar Refractivity: 100.0009 cm^3
• Polarizability: 39.152336 Å^3
• Polar Surface Area: 160.75 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

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

Safety Information

• Storage Condition: desiccated
• 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: vial of 10 μmol
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C17H15N5O7PNa

DETAILS

Sigma Aldrich - B4560

Biochem/physiol Actions
6-Bnz-cAMP is a membrane permeable and selective cAMP-dependent protein kinase (PKA) activator. For preferential stimulation of cAK type I, a combination with the site B selective analog 8-HA-cAMP or 8-AHA-cAMP can be used.