(9E)-9-nitrooctadec-9-enoic acid

• ChemBase ID: 175261
• Molecular Formular: C18H33NO4
• Molecular Mass: 327.45892
• Monoisotopic Mass: 327.24095854
• SMILES: C(CCCCCC/C(=C\CCCCCCCC)/[N+](=O)[O-])C(=O)O
• Canonical SMILES: CCCCCCCC/C=C(/[N+](=O)[O-])\CCCCCCCC(=O)O
• InChI: InChI=1S/C18H33NO4/c1-2-3-4-5-6-8-11-14-17(19(22)23)15-12-9-7-10-13-16-18(20)21/h14H,2-13,15-16H2,1H3,(H,20,21)/b17-14+
• InChIKey: CQOAKBVRRVHWKV-SAPNQHFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9E)-9-nitrooctadec-9-enoic acid
• IUPAC Traditional name: (9E)-9-nitrooctadec-9-enoic acid
• Synonyms: (9E)-9-Nitro-9-octadecenoic Acid; 9-Nitro Oleic Acid

Database IDs

• CAS Number: 875685-44-2
• PubChem SID: 164231171
• PubChem CID: 11645581

CALCULATED PROPERTIES

• Acid pKa: 4.5854344
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.001452
• LogD (pH = 7.4): 3.2261922
• Log P: 5.9648566
• Molar Refractivity: 93.7748 cm^3
• Polarizability: 36.058655 Å^3
• Polar Surface Area: 83.12 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - N496875

9-Nitrooleic Acid is a bioactive, nitric-oxide derived fatty acid. 9-Nitrooleic Acid thats acts as an irreversible inhibitor of xanthine oxidoreductase. 9-Nitrooleic Acid is a novel antagonist of Ang II-induced hypertension. 9-Nitrooleic Acid is an endoge

REFERENCES

• Kelley, E.E. et al.: J. Biol. Chem., 283, 36176 (2008)
• Zhang, J. et al.: Circul. Res., 107, 540 (2008)
• Wang, H. et al.: PPAR Res., No pp. given (2008)
• Batthyany, C., et al.: J. Biol. Chem., 281, 20450 (2008)