1-N-(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-3-N-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide

• ChemBase ID: 171726
• Molecular Formular: C18H24I3N3O8
• Molecular Mass: 791.11187
• Monoisotopic Mass: 790.86975874
• SMILES: c1(c(c(c(c(c1C(=O)NCC(CO)O)I)C(=O)NCCO)I)N(CC(CO)O)C(=O)C)I
• Canonical SMILES: OCCNC(=O)c1c(I)c(C(=O)NCC(CO)O)c(c(c1I)N(C(=O)C)CC(CO)O)I
• InChI: InChI=1S/C18H24I3N3O8/c1-8(28)24(5-10(30)7-27)16-14(20)11(17(31)22-2-3-25)13(19)12(15(16)21)18(32)23-4-9(29)6-26/h9-10,25-27,29-30H,2-7H2,1H3,(H,22,31)(H,23,32)
• InChIKey: UUMLTINZBQPNGF-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-N-(2,3-dihydroxypropyl)-5-[N-(2,3-dihydroxypropyl)acetamido]-3-N-(2-hydroxyethyl)-2,4,6-triiodobenzene-1,3-dicarboxamide
• IUPAC Traditional name: ioxilan
• Synonyms: 5-[Acetyl(2,3-dihydroxypropyl)amino]-N1-(2,3-dihydroxypropyl)-N3-(2-hydroxyethyl)-2,4,6-triiodo-1,3-benzenedicarboxamide; Ioxitol; Oxilan 300; Ioxilan

Database IDs

• CAS Number: 107793-72-6
• PubChem SID: 164227636
• PubChem CID: 3743

CALCULATED PROPERTIES

• Acid pKa: 11.736321
• H Acceptors: 8
• H Donor: 7
• LogD (pH = 5.5): -1.3204877
• LogD (pH = 7.4): -1.3205053
• Log P: -1.3204875
• Molar Refractivity: 142.8765 cm^3
• Polarizability: 55.304 Å^3
• Polar Surface Area: 179.66 Å^2
• Rotatable Bonds: 11
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - I737500

Nonionic iodinated contrast medium. Diagnostic aid (radiopaque medium).

REFERENCES

• Foster, S.J, et al.: Invest. Radiol., 23, Suppl.1, S106 (1988)
• Yap, C., et al.: Toxicol. Sci., 79, 170 (1988)
• Muller, P., et al.: J. Med. Chem., 49, 6768 (1988)
• Horvat, A., et al.: Physiol. Res., 55, 325 (1988)