triethylazanium (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: 159566
• Molecular Formular: C16H27N6O6P
• Molecular Mass: 430.395941
• Monoisotopic Mass: 430.17296924
• SMILES: [C@@H]12[C@@H]([C@H](O[C@H]1n1c3c(nc1)c(ncn3)N)CO)OP(=O)(O2)[O-].[NH+](CC)(CC)CC
• Canonical SMILES: OC[C@H]1O[C@H]([C@H]2[C@@H]1OP(=O)(O2)[O-])n1cnc2c1ncnc2N.CC[NH+](CC)CC
• InChI: InChI=1S/C10H12N5O6P.C6H15N/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;1-4-7(5-2)6-3/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);4-6H2,1-3H3/t4-,6-,7-,10-;/m1./s1
• InChIKey: QVJJZPQQHXBBJK-MCDZGGTQSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triethylazanium (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: 2',3'-cyclic amp; TEAH
• Synonyms: Adenosine Cyclic 2’,3’-(Hydrogen Phosphate) Triethylammonium Salt; 2’,3’-cAMP Triethylammonium Salt; Cyclic 2’,3’-AMP Triethylammonium Salt; 2’,3’-Cyclic Adenosine Monophosphate Triethylammonium Salt; Adenosine Cyclic 2’,3’-Monophosphate Triethylammonium Salt; Adenosine 2',3'-Cyclic Phosphate Triethylammonium Salt

Database IDs

• PubChem SID: 162253701
• PubChem CID: 71313038

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: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid
• Melting Point: >203°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A280500

A 2',3'-cyclic nucleotide phosphodiester.

REFERENCES

• Voegtli, W., et al.: Biochemistry, 39, 15365 (2000)
• Bernstein, N., et al.: Mol. Cell, 17, 657 (2000)
• Blondal, T., et al.: J. Biol. Chem., 280, 5188 (2000)
• Shenoy, A., et al.: J. Mol. Biol., 365, 211 (2000)