6-hydroxy-9-nitro-14,16-dioxatetracyclo[8.7.0.02,7.013,17]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid

• ChemBase ID: 160803
• Molecular Formular: C16H9NO7
• Molecular Mass: 327.24516
• Monoisotopic Mass: 327.03790163
• SMILES: c1ccc(c2c1c1c(c(c2)[N+](=O)[O-])c(cc2c1OCO2)C(=O)O)O
• Canonical SMILES: [O-][N+](=O)c1cc2c(O)cccc2c2c1c(cc1c2OCO1)C(=O)O
• InChI: InChI=1S/C16H9NO7/c18-11-3-1-2-7-8(11)4-10(17(21)22)13-9(16(19)20)5-12-15(14(7)13)24-6-23-12/h1-5,18H,6H2,(H,19,20)
• InChIKey: LGZIKBZSCRORQN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid
• IUPAC Traditional name: 6-hydroxy-9-nitro-14,16-dioxatetracyclo[8.7.0.0^2,^7.0^1^3,^1^7]heptadeca-1(17),2,4,6,8,10,12-heptaene-11-carboxylic acid
• Synonyms: 8-Hydroxy-6-nitrophenanthro[4,3-d]-1,3-dioxole-5-carboxylic Acid; Aristolochic Acid Ia

Database IDs

• CAS Number: 38965-71-8
• PubChem SID: 162254938
• PubChem CID: 148297

CALCULATED PROPERTIES

• Acid pKa: 3.324094
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.70890325
• LogD (pH = 7.4): -0.5944349
• Log P: 2.8694346
• Molar Refractivity: 81.2871 cm^3
• Polarizability: 32.6383 Å^3
• Polar Surface Area: 121.81 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A771295

A metabolite of carcinogenic Aristolochic acids (AAs).

REFERENCES

• Mengs, U., et al.: Arch. Toxicol., 61, 504 (1988)
• Arlt, V., et al.: Mutagenesis, 17, 265 (1988)
• Stiborova, M., et al.: Carcinogenesis, 24, 1695 (1988)