{[(2R,3R,5R)-3-hydroxy-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-2-yl]methoxy}phosphonic acid

• ChemBase ID: 168289
• Molecular Formular: C12H14N5O6P
• Molecular Mass: 355.243221
• Monoisotopic Mass: 355.06816982
• SMILES: [C@H]1(C[C@@H](O[C@@H]1COP(=O)(O)O)n1c2ncn3c(c2nc1)ncc3)O
• Canonical SMILES: O[C@@H]1C[C@@H](O[C@@H]1COP(=O)(O)O)n1cnc2c1ncn1c2ncc1
• InChI: InChI=1S/C12H14N5O6P/c18-7-3-9(23-8(7)4-22-24(19,20)21)17-6-14-10-11-13-1-2-16(11)5-15-12(10)17/h1-2,5-9,18H,3-4H2,(H2,19,20,21)/t7-,8-,9-/m1/s1
• InChIKey: CACCSKNYAUKFAV-IWSPIJDZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,5R)-3-hydroxy-5-{3H-imidazo[2,1-f]purin-3-yl}oxolan-2-yl]methoxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,5R)-3-hydroxy-5-{imidazo[2,1-f]purin-3-yl}oxolan-2-yl]methoxyphosphonic acid
• Synonyms: 3-(2-Deoxy-5-O-phosphono-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purine; 1,N6-Etheno-2'-deoxy-AMP; Etheno-2'-deoxy-β-D-adenosine 5'-Monophosphate

Database IDs

• CAS Number: 60508-81-8
• PubChem SID: 162262421
• PubChem CID: 71316499

CALCULATED PROPERTIES

• Acid pKa: 1.2516966
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -3.9783697
• LogD (pH = 7.4): -5.0915956
• Log P: -3.7179263
• Molar Refractivity: 78.954 cm^3
• Polarizability: 31.056107 Å^3
• Polar Surface Area: 144.23 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - E890385

A phosphorylated adenosine derivative used as probes of the activator site of glycogen phosphorylase. It is used in method for detecting misincorporation during DNA synthesis.

REFERENCES

• Vandenbunder, B. et al.: Proc, Nat. Acd. Sci. U.S.A., 73, 2696 (1976)
• Revich, G.G. et al.: Carcinogen., 7, 1569 (1976)