5-carbamoyl-3-[(2R,3R,4R,5S)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]-2,3-dihydro-1H-imidazol-1-ium-4-olate

• ChemBase ID: 1712
• Molecular Formular: C9H13N3O9P--
• Molecular Mass: 338.187981
• Monoisotopic Mass: 338.03894064
• SMILES: NC(=O)C1=C([O-])N(C[NH+]1)[C@@H]1O[C@@H](COP(=O)([O-])[O-])[C@H](O)[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H](O)[C@@H](O[C@H]1N1C[NH+]C(=C1[O-])C(=O)N)COP(=O)([O-])[O-]
• InChI: InChI=1S/C9H16N3O9P/c10-7(15)4-8(16)12(2-11-4)9-6(14)5(13)3(21-9)1-20-22(17,18)19/h3,5-6,9,11,13-14,16H,1-2H2,(H2,10,15)(H2,17,18,19)/p-2/t3-,5-,6+,9+/m0/s1
• InChIKey: NTDZCJUPKJXMLU-BZKDHIKHSA-L

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-carbamoyl-3-[(2R,3R,4R,5S)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]-2,3-dihydro-1H-imidazol-1-ium-4-olate
• IUPAC Traditional name: 5-carbamoyl-3-[(2R,3R,4R,5S)-3,4-dihydroxy-5-[(phosphonatooxy)methyl]oxolan-2-yl]-1,2-dihydroimidazol-1-ium-4-olate
• Synonyms: 4-Carbamoyl-1-Beta-D-Ribofuranosyl-Imidazolium-5-Olate-5'-Phosphate

Database IDs

• PubChem SID: 46505797; 160965168
• PubChem CID: 46936267

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.2578626
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -5.5412707
• LogD (pH = 7.4): -6.6297812
• Log P: -3.353883
• Molar Refractivity: 97.6309 cm^3
• Polarizability: 26.997845 Å^3
• Polar Surface Area: 208.11 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.4
• LOG S: -1.02
• Solubility (Water): 4.07e+01 g/l

DETAILS

DrugBank - DB01945

Drug information: experimental