triethylazanium (3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-6-[hydroxy(13C)methyl]-2-oxo-tetrahydro(3a,4,6,6a-13C4)-2H-1,3,5,2λ5-furo[3,4-d][1,3,2λ5]dioxaphosphol-2-olate

• ChemBase ID: 159567
• Molecular Formular: C16H27N6O6P
• Molecular Mass: 435.35921519
• Monoisotopic Mass: 435.18974343
• SMILES: [13C@@H]12OP(=O)(O[13C@H]2[13C@H](n2cnc3c2ncnc3N)O[13C@@H]1[13CH2]O)[O-].[NH+](CC)(CC)CC
• Canonical SMILES: O[13CH2][13C@H]1O[13C@H]([13C@H]2[13C@@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/i1+1,4+1,6+1,7+1,10+1
• InChIKey: QVJJZPQQHXBBJK-GMKAKXBPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: triethylazanium (3aR,4R,6R,6aR)-4-(6-amino-9H-purin-9-yl)-6-[hydroxy(^1^3C)methyl]-2-oxo-tetrahydro(3a,4,6,6a-^1^3C₄)-2H-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-2-olate
• IUPAC Traditional name: TEAH (3aR,4R,6R,6aR)-4-(6-aminopurin-9-yl)-6-[hydroxy(^1^3C)methyl]-2-oxo-tetrahydro(3a,4,6,6a-^1^3C₄)-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-2-olate
• Synonyms: Adenosine Cyclic 2’,3’-(Hydrogen Phosphate)-13C5Triethylammonium Salt; 2’,3’-cAMP-13C5; Cyclic 2’,3’-AMP-13C5; 2’,3’-Cyclic Adenosine Monophosphate-13C5; Adenosine Cyclic 2’,3’-Monophosphate-13C5 Triethylammonium Salt; Adenosine 2',3'-Cyclic Phosphate-13C5 Triethylammonium Salt

Database IDs

• PubChem SID: 162253702
• PubChem CID: 71313039

CALCULATED PROPERTIES

• Acid pKa: 1.758685
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -3.771957
• LogD (pH = 7.4): -3.695558
• Log P: -4.06257
• 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: >180°C (dec.)

Safety Information

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

DETAILS

Toronto Research Chemicals - A280502

A labelled 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)