3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)-N-[(3S,5S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide

• ChemBase ID: 174598
• Molecular Formular: C18H22I3N3O8
• Molecular Mass: 789.09599
• Monoisotopic Mass: 788.85410868
• SMILES: O1C([C@@H](C([C@@H](C1CO)O)O)NC(=O)c1c(c(c(c(c1I)NC(=O)C)I)N(C(=O)C)C)I)O
• Canonical SMILES: OCC1OC(O)[C@@H](C([C@@H]1O)O)NC(=O)c1c(I)c(NC(=O)C)c(c(c1I)N(C(=O)C)C)I
• InChI: InChI=1S/C18H22I3N3O8/c1-5(26)22-12-9(19)8(10(20)14(11(12)21)24(3)6(2)27)17(30)23-13-16(29)15(28)7(4-25)32-18(13)31/h7,13,15-16,18,25,28-29,31H,4H2,1-3H3,(H,22,26)(H,23,30)/t7?,13-,15+,16?,18?/m0/s1
• InChIKey: BAQCROVBDNBEEB-UBLAARQISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)-N-[(3S,5S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide
• IUPAC Traditional name: 3-acetamido-2,4,6-triiodo-5-(N-methylacetamido)-N-[(3S,5S)-2,4,5-trihydroxy-6-(hydroxymethyl)oxan-3-yl]benzamide
• Synonyms: 2-[[3-(Acetylamino)-5-(acetylmethylamino)-2,4,6-triiodobenzoyl]amino]-2-deoxy-D-glucose; Amipaque; Metrizamide; Telebrix 300; Metrizamide

Database IDs

• CAS Number: 31112-62-6
• PubChem SID: 164230508
• PubChem CID: 45039930

CALCULATED PROPERTIES

• Acid pKa: 11.444519
• H Acceptors: 8
• H Donor: 6
• LogD (pH = 5.5): -0.24008025
• LogD (pH = 7.4): -0.24011765
• Log P: -0.24007973
• Molar Refractivity: 140.6246 cm^3
• Polarizability: 54.876026 Å^3
• Polar Surface Area: 168.66 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Isopropyl Alcohol
• Apperance: White Crystalline Solid
• Melting Point: 230°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M338850

Metrizamide is a X-ray contrast agent related to Metrizoic Acid (M338935). Metrizamide is used as an diagnostic aid (radiopaque medium).

REFERENCES

• Salvesen, S., et al.: Radiology, 123, 241 (1977)
• Dibona, G.F., et al.: Ann. Radiol., 22, 195 (1977)