dibarium(2+) ion (2S)-2-({5-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioate

• ChemBase ID: 177842
• Molecular Formular: C13H15Ba2N4O12P
• Molecular Mass: 724.905561
• Monoisotopic Mass: 725.85290257
• SMILES: [Ba+2].[Ba+2].Nc1c(C(=O)N[C@@H](CC(=O)[O-])C(=O)[O-])ncn1[C@H]1C([C@H]([C@H](O1)COP(=O)([O-])[O-])O)O
• Canonical SMILES: [O-]C(=O)C[C@@H](C(=O)[O-])NC(=O)c1ncn(c1N)[C@@H]1O[C@@H]([C@@H](C1O)O)COP(=O)([O-])[O-].[Ba+2].[Ba+2]
• InChI: InChI=1S/C13H19N4O12P.2Ba/c14-10-7(11(22)16-4(13(23)24)1-6(18)19)15-3-17(10)12-9(21)8(20)5(29-12)2-28-30(25,26)27;;/h3-5,8-9,12,20-21H,1-2,14H2,(H,16,22)(H,18,19)(H,23,24)(H2,25,26,27);;/q;2*+2/p-4/t4-,5+,8-,9?,12+;;/m0../s1
• InChIKey: PPKOPCLLXBFYGS-NPWMYEBASA-J

NAMES AND DATABASE IDS

Names

• IUPAC name: dibarium(2+) ion (2S)-2-({5-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]-1H-imidazol-4-yl}formamido)butanedioate
• IUPAC Traditional name: dibarium(2+) ion (2S)-2-({5-amino-1-[(2R,4R,5R)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]imidazol-4-yl}formamido)butanedioate
• Synonyms: N-[[5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazol-4-yl]carbonyl]-L-aspartic Acid Barium Salt; N-[(5-Amino-1-β-D-ribofuranosylimidazol-4-yl)carbonyl]-L-aspartic Acid 5'-(Dihydrogen Phosphate) Barium Salt; Saicar Dibarium Salt; N-Succinyl-5-aminoimidazole-4-carboxamide Ribose 5'-Phosphate Dibarium Salt

Database IDs

• CAS Number: 6057-44-9
• PubChem SID: 164233752
• PubChem CID: 71752225

CALCULATED PROPERTIES

• Acid pKa: 1.2173138
• H Acceptors: 13
• H Donor: 4
• LogD (pH = 5.5): -8.111787
• LogD (pH = 7.4): -12.394793
• Log P: -4.8253617
• Molar Refractivity: 110.0835 cm^3
• Polarizability: 35.29167 Å^3
• Polar Surface Area: 275.31 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - S688795

A metabolite of Purine. Purine metabolism by adenylosuccinasedeficient. Since adenosine is a potent inhibitor of neuronal function, depressing the release of several excitatory transmitters and causing direct hyperpolarization of neurons, it was possible

REFERENCES

• Gollub, E.G., et al.: J. Bacteriol., 78, 320 (1959)
• Srivastava, P.C., et al.: J. Med. Chem., 17, 1207 (1959)