N-(3-{2-[bis(2H3)methylamino]ethyl}-2,4-dioxo-3-azatricyclo[7.3.1.05,13]trideca-1(12),5(13),6,8,10-pentaen-7-yl)acetamide

• ChemBase ID: 159132
• Molecular Formular: C18H19N3O3
• Molecular Mass: 325.36176
• Monoisotopic Mass: 325.14264148
• SMILES: c1c2c3c(cc1NC(=O)C)c(=O)n(c(=O)c3ccc2)CCN(C)C
• Canonical SMILES: CN(CCn1c(=O)c2cc(NC(=O)C)cc3c2c(c1=O)ccc3)C
• InChI: InChI=1S/C18H19N3O3/c1-11(22)19-13-9-12-5-4-6-14-16(12)15(10-13)18(24)21(17(14)23)8-7-20(2)3/h4-6,9-10H,7-8H2,1-3H3,(H,19,22)
• InChIKey: VQQUFGOEIGXAOM-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-(3-{2-[bis(^2H₃)methylamino]ethyl}-2,4-dioxo-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(12),5(13),6,8,10-pentaen-7-yl)acetamide
• IUPAC Traditional name: N-(3-{2-[bis(^2H₃)methylamino]ethyl}-2,4-dioxo-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(12),5(13),6,8,10-pentaen-7-yl)acetamide
• Synonyms: N-[2-[2-(Dimethylamino-d6)ethyl]-2,3-dihydro-1,3-dioxo-1H-benz[de]isoquinolin-5-yl]acetamide; MADE-FA 4512-d6; N-Acetylamonafide-d6; N-Acetyl Amonafide-d6

Database IDs

• PubChem SID: 162253267
• PubChem CID: 46779945

CALCULATED PROPERTIES

• Acid pKa: 13.847325
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.731706
• LogD (pH = 7.4): 0.015319837
• Log P: 1.1629307
• Molar Refractivity: 93.5438 cm^3
• Polarizability: 35.404797 Å^3
• Polar Surface Area: 69.72 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A168302

A labelled metabolite of Amonafide.

REFERENCES

• Felder, T.B., et al.: Drug Metab. Dispos., 15, 773 (1987)
• Frei, E., et al.: Cancer Res., 48, 6417 (1987)
• Liu, Y., et al.: Bioorg. Med. Chem., 14, 2935 (1987)