(6E,8Z)-18-hydroxy-5-oxooctadeca-6,8-dienoic acid

• ChemBase ID: 171058
• Molecular Formular: C18H30O4
• Molecular Mass: 310.4284
• Monoisotopic Mass: 310.21440944
• SMILES: C(=C\CCCCCCCCCO)\C=C\C(=O)CCCC(=O)O
• Canonical SMILES: OCCCCCCCCC/C=C\C=C\C(=O)CCCC(=O)O
• InChI: InChI=1S/C18H30O4/c19-16-11-9-7-5-3-1-2-4-6-8-10-13-17(20)14-12-15-18(21)22/h6,8,10,13,19H,1-5,7,9,11-12,14-16H2,(H,21,22)/b8-6-,13-10+
• InChIKey: WUMXVBSMANMBJK-WLPHGBIISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6E,8Z)-18-hydroxy-5-oxooctadeca-6,8-dienoic acid
• IUPAC Traditional name: (6E,8Z)-18-hydroxy-5-oxooctadeca-6,8-dienoic acid
• Synonyms: 5-oxo-18-HODE; 5-Oxo-18-hydroxy-(6E,8Z)-octadecadienoic Acid; (6E,8Z)-18-Hydroxy-5-oxo-6,8-octadecadienoic Acid

Database IDs

• CAS Number: 1021188-26-0
• PubChem SID: 164226968
• PubChem CID: 71749242

CALCULATED PROPERTIES

• Acid pKa: 4.426203
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.0582678
• LogD (pH = 7.4): 1.2980599
• Log P: 4.1657257
• Molar Refractivity: 91.0656 cm^3
• Polarizability: 34.601627 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H949020

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)