sodium (3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-1,3,5,2λ5-furo[3,4-d][1,3,2λ5]dioxaphosphol-2-olate

• ChemBase ID: 159565
• Molecular Formular: C10H11N5NaO6P
• Molecular Mass: 351.187771
• Monoisotopic Mass: 351.03446401
• SMILES: [C@H]12[C@H]([C@@H](O[C@@H]1CO)n1c3c(nc1)c(ncn3)N)OP(=O)(O2)[O-].[Na+]
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]2[C@@H]1OP(=O)(O2)[O-])n1cnc2c1ncnc2N.[Na+]
• InChI: InChI=1S/C10H12N5O6P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(17,18)21-7;/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1
• InChIKey: VSDSIACSNXHGOV-MCDZGGTQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-6-(hydroxymethyl)-2-oxo-tetrahydro-2H-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-2-olate
• IUPAC Traditional name: sodium 2',3'-cyclic amp
• Synonyms: Adenosine Cyclic 2',3'-(Hydrogen Phosphate) Monosodium Salt; 2',3'-Cyclic AMP Sodium Salt; Adenosine 2',3'-Cyclic Monophosphate Sodium Salt; Adenosine 2',3'-Cyclic Phosphate Sodium Salt; Cyclic Adenosine 2',3'-Monophosphate Sodium Salt; NSC 154034; Adenosine-2',3'-cyclic Monophosphate Sodium Salt

Database IDs

• CAS Number: 37063-35-7
• PubChem SID: 162253700
• PubChem CID: 23666344

CALCULATED PROPERTIES

• Acid pKa: 1.7586842
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -3.771956
• LogD (pH = 7.4): -3.695558
• Log P: -4.0625772
• Molar Refractivity: 69.1678 cm^3
• Polarizability: 27.794725 Å^3
• Polar Surface Area: 157.67 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: White Solid
• Melting Point: 230-232°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - A280450

Adenosine-2’,3’-cyclic Monophosphate is an Adenosine (A280400) derivative useful as anticancer agent.

REFERENCES

• Touil, F., et al.: J. Pharm. Biomed. Anal., 40, 822 (2006)