5-amino-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

• ChemBase ID: 159866
• Molecular Formular: C14H18I3N3O6
• Molecular Mass: 705.02263
• Monoisotopic Mass: 704.83297931
• SMILES: c1(c(c(c(c(c1I)N)I)C(=O)NCC(O)CO)I)C(=O)NCC(O)CO
• Canonical SMILES: OCC(CNC(=O)c1c(I)c(C(=O)NCC(CO)O)c(c(c1I)N)I)O
• InChI: InChI=1S/C14H18I3N3O6/c15-9-7(13(25)19-1-5(23)3-21)10(16)12(18)11(17)8(9)14(26)20-2-6(24)4-22/h5-6,21-24H,1-4,18H2,(H,19,25)(H,20,26)
• InChIKey: KAEGSAWWVYMWIQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-amino-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
• IUPAC Traditional name: 5-amino-1-N,3-N-bis(2,3-dihydroxypropyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
• Synonyms: 5-Amino-N1,N3-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide; 3,5-Bis(2,3-dihydroxypropylaminocarbonyl)-2,4,6-triiodoaniline; 5-Amino-2,4,6-triiodo-N,N'-bis(2,3-dihydroxypropyl)isophthalamide; 5-Amino-N,N’-bis(2,3-dihydroxypropyl)-2,4,6-triiodoisophthalamide; 5-Amino-N,N'-bis(2,3-dihydroxypropyl)-2,4,6-triiodo-1,3-benzenedicarboxamide

Database IDs

• CAS Number: 76801-93-9
• PubChem SID: 162254001
• PubChem CID: 10395011

CALCULATED PROPERTIES

• Acid pKa: 12.073892
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): -0.56108975
• LogD (pH = 7.4): -0.5610961
• Log P: -0.5610879
• Molar Refractivity: 123.3057 cm^3
• Polarizability: 47.275047 Å^3
• Polar Surface Area: 165.14 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - A601920

Used as an intermediate in the industrial preparation of non-ionic X-ray contrast agents such as Iohexol (I729500), Ioversol (I737000), Ioxilan (I737500), Iopamidol (I735600).

REFERENCES

• Rongved, P., et al.: Carbohydrate Res., 297, 325 (1997)