(9E)-10-nitrooctadec-9-enoic acid

• ChemBase ID: 175262
• 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\CCCCCCCC(=O)O)/[N+](=O)[O-]
• InChI: InChI=1S/C18H33NO4/c1-2-3-4-5-8-11-14-17(19(22)23)15-12-9-6-7-10-13-16-18(20)21/h15H,2-14,16H2,1H3,(H,20,21)/b17-15+
• InChIKey: WRADPCFZZWXOTI-BMRADRMJSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (9E)-10-nitrooctadec-9-enoic acid
• IUPAC Traditional name: (9E)-10-nitrooctadec-9-enoic acid
• Synonyms: (9E)-10-Nitro-9-octadecenoic Acid; 10-Nitro Oleic Acid

Database IDs

• CAS Number: 875685-46-4
• PubChem SID: 164231172
• PubChem CID: 24836820

CALCULATED PROPERTIES

• Acid pKa: 4.9881673
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.336923
• LogD (pH = 7.4): 3.5832667
• 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 - N496880

Nitroalkene derivative of oleic acid (OA-NO2) inhibits lipopolysaccharide-induced secretion of proinflammatory cytokines in macrophages independent of nitric oxide formation, peroxisome proliferator-activated receptor-γ (PPARγ) activation, or induction of

REFERENCES

• Feng, X., et al.: J. Clin. Invest., 107, 1137 (2001)
• Coles, B., et al.: J. Biol. Chem., 277, 5832 (2001)
• Batthyany, C., et al.: J. Biol. Chem., 281, 20450 (2001)