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: 160804
• Molecular Formular: C16H9NO6
• Molecular Mass: 311.24576
• Monoisotopic Mass: 311.04298701
• SMILES: c1cccc2c1c1c(c(c2)[N+](=O)[O-])c(cc2c1OCO2)C(=O)O
• Canonical SMILES: [O-][N+](=O)c1cc2ccccc2c2c1c(cc1c2OCO1)C(=O)O
• InChI: InChI=1S/C16H9NO6/c18-16(19)10-6-12-15(23-7-22-12)14-9-4-2-1-3-8(9)5-11(13(10)14)17(20)21/h1-6H,7H2,(H,18,19)
• InChIKey: MEEXETVZNQYRSP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 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: aristolochic acid II
• Synonyms: 6-Nitro-phenanthro[3,4-d]-1,3-dioxole-5-carboxylic Acid; Aristolochic Acid II; 3,4-(Methylenedioxy)-10-nitrophenanthrene-1-carboxylic Acid; Aristolochic Acid B

Database IDs

• CAS Number: 475-80-9
• PubChem SID: 162254939
• PubChem CID: 108168

CALCULATED PROPERTIES

• Acid pKa: 3.324431
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 1.0133542
• LogD (pH = 7.4): -0.24781078
• Log P: 3.1729999
• Molar Refractivity: 79.3062 cm^3
• Polarizability: 32.00752 Å^3
• Polar Surface Area: 101.58 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A771305

Aristolochic acids occur in Aristolochiaceae and in butterflies feeding on these plants. One of a group of fourteen known, substituted 1-phenanthrenecarboxylic acids.

REFERENCES

• Coutts, et al.: J. Pharm. Pharmacol., 11, 607 (1959)
• Kupchan, D., et al.: J. Med. Pharm. Chem., 5, 657 (1959)
• Mix, D.B., et al.: J. Nat. Prod., 45, 657 (1959)
• Mengs, U., et al.: Arch. Toxixol., 59, 328 (1959)