4-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: 160805
• Molecular Formular: C16H9NO7
• Molecular Mass: 327.24516
• Monoisotopic Mass: 327.03790163
• SMILES: c1c(ccc2c1c1c(c(c2)[N+](=O)[O-])c(cc2c1OCO2)C(=O)O)O
• Canonical SMILES: Oc1ccc2c(c1)c1c3OCOc3cc(c1c(c2)[N+](=O)[O-])C(=O)O
• InChI: InChI=1S/C16H9NO7/c18-8-2-1-7-3-11(17(21)22)13-10(16(19)20)5-12-15(24-6-23-12)14(13)9(7)4-8/h1-5,18H,6H2,(H,19,20)
• InChIKey: NBFGYDJKTHENDP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-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: 4-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: 10-Hydroxy-6-nitro-phenanthro[3,4-d]-1,3-dioxole-5-carboxylic Acid; Aristolochic Acid IIIa; Aristolochic Acid C

Database IDs

• CAS Number: 4849-90-5
• PubChem SID: 162254940
• PubChem CID: 165274

CALCULATED PROPERTIES

• Acid pKa: 3.3242414
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 0.7094603
• LogD (pH = 7.4): -0.56310934
• Log P: 2.8694346
• Molar Refractivity: 81.2871 cm^3
• Polarizability: 32.634686 Å^3
• Polar Surface Area: 121.81 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A771310

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)