tetraammonium ({[(2R,3S,4R,5R)-5-(6-amino-8-azido-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(phosphonatooxy)phosphinate

• ChemBase ID: 160977
• Molecular Formular: C10H27N12O13P3
• Molecular Mass: 616.315263
• Monoisotopic Mass: 616.10333887
• SMILES: [C@H]1([C@H]([C@H]([C@@H](O1)n1c2ncnc(c2nc1N=[N+]=[N-])N)O)O)COP(=O)(OP(=O)(OP(=O)([O-])[O-])[O-])[O-].[NH4+].[NH4+].[NH4+].[NH4+]
• Canonical SMILES: [N-]=[N+]=Nc1nc2c(n1[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COP(=O)(OP(=O)(OP(=O)([O-])[O-])[O-])[O-])ncnc2N.[NH4+].[NH4+].[NH4+].[NH4+]
• InChI: InChI=1S/C10H15N8O13P3.4H3N/c11-7-4-8(14-2-13-7)18(10(15-4)16-17-12)9-6(20)5(19)3(29-9)1-28-33(24,25)31-34(26,27)30-32(21,22)23;;;;/h2-3,5-6,9,19-20H,1H2,(H,24,25)(H,26,27)(H2,11,13,14)(H2,21,22,23);4*1H3/t3-,5-,6-,9-;;;;/m1..../s1
• InChIKey: GSBFOPOEFZZQSW-ZVQJTLEUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tetraammonium ({[(2R,3S,4R,5R)-5-(6-amino-8-azido-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)(phosphonatooxy)phosphinate
• IUPAC Traditional name: tetraammonium {[(2R,3S,4R,5R)-5-(6-amino-8-azidopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy(phosphonatooxy)phosphinate
• Synonyms: 8-Azidoadenosine 5'-Triphosphate, Ammonium Salt DISCONTINUED

Database IDs

• PubChem SID: 162255112
• PubChem CID: 71313565

CALCULATED PROPERTIES

• Acid pKa: 0.89519566
• H Acceptors: 16
• H Donor: 3
• LogD (pH = 5.5): -8.787243
• LogD (pH = 7.4): -9.478406
• Log P: -4.0980186
• Molar Refractivity: 101.0884 cm^3
• Polarizability: 40.60642 Å^3
• Polar Surface Area: 319.88 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White Solid

REFERENCES

• Czarnecki, J. et al.: Methods in Enzymol., 56, 642 (1979)
• Scheiner-Bobis, G., et al.: Eur. J. Biochem., 152(1979)
• 739 (1985)