11-amino-3-{2-[bis(2H3)methylamino]ethyl}-3-azatricyclo[7.3.1.05,13]trideca-1(13),5,7,9,11-pentaene-2,4-dione

• ChemBase ID: 160567
• Molecular Formular: C16H17N3O2
• Molecular Mass: 283.32508
• Monoisotopic Mass: 283.1320768
• SMILES: c1c2c3c(cc1N)c(=O)n(c(=O)c3ccc2)CCN(C)C
• Canonical SMILES: CN(CCn1c(=O)c2cc(N)cc3c2c(c1=O)ccc3)C
• InChI: InChI=1S/C16H17N3O2/c1-18(2)6-7-19-15(20)12-5-3-4-10-8-11(17)9-13(14(10)12)16(19)21/h3-5,8-9H,6-7,17H2,1-2H3
• InChIKey: UPALIKSFLSVKIS-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 11-amino-3-{2-[bis(^2H₃)methylamino]ethyl}-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(13),5,7,9,11-pentaene-2,4-dione
• IUPAC Traditional name: 11-amino-3-{2-[bis(^2H₃)methylamino]ethyl}-3-azatricyclo[7.3.1.0^5,^1^3]trideca-1(13),5,7,9,11-pentaene-2,4-dione
• Synonyms: 5-Amino-2-[2-(dimethylamino-d6)ethyl]-1H-benz[de]isoquinoline-1,3(2H)-dione; FA 142-d6; M-FA 142-d6; MADE-FA 142-d6; NCI 308847-d6; NSC 308847-d6; Nafidimide-d6; Amonafide-d6

Database IDs

• PubChem SID: 162254702
• PubChem CID: 46780376

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -1.7992526
• LogD (pH = 7.4): -0.05132785
• Log P: 1.0962944
• Molar Refractivity: 83.3812 cm^3
• Polarizability: 31.664867 Å^3
• Polar Surface Area: 66.64 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A634207

Labelled Amonafide. It is a DNA intercalator and topoisomerase II inhibitor in clinical development for the treatment of neoplastic diseases. Antitumor agent.

REFERENCES

• Hsiang, Y., et al.: Mol. Pharmacol., 36, 371 (1989)
• Costanza, M., et al.: Clin. Cancer Res., 1, 699 (1989)
• Innocenti, F., et al.: Drug Metab. Dispos., 29, 596 (1989)
• Brana, M., et al.: J. Med. Chem., 47, 1391 (1989)