4-hydroxy-6-methoxy-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: 160806
• Molecular Formular: C17H11NO8
• Molecular Mass: 357.27114
• Monoisotopic Mass: 357.04846632
• SMILES: c1c(cc(c2c1c1c(c(c2)[N+](=O)[O-])c(cc2c1OCO2)C(=O)O)OC)O
• Canonical SMILES: COc1cc(O)cc2c1cc([N+](=O)[O-])c1c2c2OCOc2cc1C(=O)O
• InChI: InChI=1S/C17H11NO8/c1-24-12-3-7(19)2-9-8(12)4-11(18(22)23)14-10(17(20)21)5-13-16(15(9)14)26-6-25-13/h2-5,19H,6H2,1H3,(H,20,21)
• InChIKey: PADIFGYTAXNCRK-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-hydroxy-6-methoxy-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-6-methoxy-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-8-methoxy-6-nitrophenanthro[3,4-d]-1,3-dioxole-5-carboxylic Acid; Aristolochic Acid IVa; Aristolochic Acid D

Database IDs

• CAS Number: 17413-38-6
• PubChem SID: 162254941
• PubChem CID: 161218

CALCULATED PROPERTIES

• Acid pKa: 3.3239045
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.55112696
• LogD (pH = 7.4): -0.74665964
• Log P: 2.7117634
• Molar Refractivity: 87.7503 cm^3
• Polarizability: 35.179184 Å^3
• Polar Surface Area: 131.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A771315

A derivative 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)