14-methoxy-3,5-dioxa-10-azapentacyclo[9.7.1.02,6.08,19.013,18]nonadeca-1,6,8(19),11,13,15,17-heptaen-9-one

• ChemBase ID: 160802
• Molecular Formular: C17H11NO4
• Molecular Mass: 293.27354
• Monoisotopic Mass: 293.06880784
• SMILES: c12c3c(c4c(cc3[nH]c1=O)c(OC)ccc4)c1c(c2)OCO1
• Canonical SMILES: COc1cccc2c1cc1[nH]c(=O)c3c1c2c1OCOc1c3
• InChI: InChI=1S/C17H11NO4/c1-20-12-4-2-3-8-9(12)5-11-14-10(17(19)18-11)6-13-16(15(8)14)22-7-21-13/h2-6H,7H2,1H3,(H,18,19)
• InChIKey: MXOKGWUJNGEKBH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 14-methoxy-3,5-dioxa-10-azapentacyclo[9.7.1.0^2,^6.0^8,^1^9.0^1^3,^1^8]nonadeca-1,6,8(19),11,13,15,17-heptaen-9-one
• IUPAC Traditional name: 14-methoxy-3,5-dioxa-10-azapentacyclo[9.7.1.0^2,^6.0^8,^1^9.0^1^3,^1^8]nonadeca-1,6,8(19),11,13,15,17-heptaen-9-one
• Synonyms: 8-Methoxybenzo[f]-1,3-benzodioxolo[6,5,4-cd]indol-5(6H)-one; Aristolactam; Aristolactam I; Aristololactam; Aristololactam I; NSC 87406; Aristolactam I

Database IDs

• CAS Number: 13395-02-3
• PubChem SID: 162254937
• PubChem CID: 96710

CALCULATED PROPERTIES

• Acid pKa: 9.981727
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 2.536387
• LogD (pH = 7.4): 2.535321
• Log P: 2.5364006
• Molar Refractivity: 80.664 cm^3
• Polarizability: 32.620335 Å^3
• Polar Surface Area: 56.79 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A771200

Aristolactam I is a metabolite of Aristolochic acids which are natural nitro-compounds found globally in the plant genus Aristolochia, having carcinogenic effects.

REFERENCES

• Vanherweghem, J., et al.: Lancet, 341, 387 (1993)
• Schmeiser, H., et al.: Cancer Res., 56, 2025 (1993)
• Arlt, V., et al.: Mutagenesis, 17, 265 (1993)
• Rosenquist, T., et al.: Drug Metab. Dispos., 38, 761 (1993)