6-hydroxy-5-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: 160807
• Molecular Formular: C17H11NO8
• Molecular Mass: 357.27114
• Monoisotopic Mass: 357.04846632
• SMILES: c1cc(c(c2c1c1c(c(c2)[N+](=O)[O-])c(cc2c1OCO2)C(=O)O)O)OC
• Canonical SMILES: COc1ccc2c(c1O)cc(c1c2c2OCOc2cc1C(=O)O)[N+](=O)[O-]
• InChI: InChI=1S/C17H11NO8/c1-24-11-3-2-7-8(15(11)19)4-10(18(22)23)13-9(17(20)21)5-12-16(14(7)13)26-6-25-12/h2-5,19H,6H2,1H3,(H,20,21)
• InChIKey: ZRCMNWRTDNPVFL-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-hydroxy-5-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: 6-hydroxy-5-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: 8-Hydroxy-9-methoxy-6-nitrophenanthro[4,3-d]-1,3-dioxole-5-carboxylic Acid; Aristolochic Acid E

Database IDs

• CAS Number: 107259-48-3
• PubChem SID: 162254942
• PubChem CID: 147113

CALCULATED PROPERTIES

• Acid pKa: 3.3241491
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): 0.55127007
• LogD (pH = 7.4): -0.7531192
• Log P: 2.7117634
• Molar Refractivity: 87.7503 cm^3
• Polarizability: 35.179745 Å^3
• Polar Surface Area: 131.04 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A771320

Α new natural product was isolated from Aristolochia contorta bunge. The other components were identified as allantoin, aristolochic acid A, magnoflorine, β-sitosterol, and daucosterol.