(6E,8Z)-5-oxooctadeca-6,8-dienoic acid

• ChemBase ID: 176104
• Molecular Formular: C18H30O3
• Molecular Mass: 294.429
• Monoisotopic Mass: 294.21949482
• SMILES: C(=C\CCCCCCCCC)\C=C\C(=O)CCCC(=O)O
• Canonical SMILES: CCCCCCCCC/C=C\C=C\C(=O)CCCC(=O)O
• InChI: InChI=1S/C18H30O3/c1-2-3-4-5-6-7-8-9-10-11-12-14-17(19)15-13-16-18(20)21/h10-12,14H,2-9,13,15-16H2,1H3,(H,20,21)/b11-10-,14-12+
• InChIKey: YVWMHFYOIJMUMN-HSINTONASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6E,8Z)-5-oxooctadeca-6,8-dienoic acid
• IUPAC Traditional name: (6E,8Z)-5-oxooctadeca-6,8-dienoic acid
• Synonyms: 5-oxo-ODE; 5-Oxo-(6E,8Z)-octadecadienoic Acid; (6E,8Z)-5-Oxo-6,8-octadecadienoic Acid

Database IDs

• CAS Number: 1021188-25-9
• PubChem SID: 164232014
• PubChem CID: 71751402

CALCULATED PROPERTIES

• Acid pKa: 4.4262023
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 4.4949465
• LogD (pH = 7.4): 2.7347386
• Log P: 5.602404
• Molar Refractivity: 89.1369 cm^3
• Polarizability: 33.98177 Å^3
• Polar Surface Area: 54.37 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - O870155

A metabolite of Sebaleic acid (5,8-octadecadienoic acid), the major polyunsaturated fatty acid in human sebum and skin surface lipids.

REFERENCES

• Powell, W., et al.: J. Biol. Chem., 268, 9280 (1993)
• O'Flaherty, J., et al.: J. Immunol., 164, 3345 (1993)