(5S,6E,8Z)-5-hydroxyoctadeca-6,8-dienoic acid

• ChemBase ID: 171116
• Molecular Formular: C18H32O3
• Molecular Mass: 296.44488
• Monoisotopic Mass: 296.23514488
• SMILES: C(=C\CCCCCCCCC)\C=C\[C@H](CCCC(=O)O)O
• Canonical SMILES: CCCCCCCCC/C=C\C=C\[C@H](CCCC(=O)O)O
• InChI: InChI=1S/C18H32O3/c1-2-3-4-5-6-7-8-9-10-11-12-14-17(19)15-13-16-18(20)21/h10-12,14,17,19H,2-9,13,15-16H2,1H3,(H,20,21)/b11-10-,14-12+/t17-/m1/s1
• InChIKey: YGKJJUMHBUARLK-LGMATZFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S,6E,8Z)-5-hydroxyoctadeca-6,8-dienoic acid
• IUPAC Traditional name: (5S,6E,8Z)-5-hydroxyoctadeca-6,8-dienoic acid
• Synonyms: 5-HODE; (5S)-5-Hydroxy-(6E,8Z)-6,8-octadecadienoic Acid; (5S,6E,8Z)-5-Hydroxy-6,8-octadecadienoic Acid

Database IDs

• CAS Number: 1021188-23-7
• PubChem SID: 164227026
• PubChem CID: 71749263

CALCULATED PROPERTIES

• Acid pKa: 4.5841017
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.2264752
• LogD (pH = 7.4): 2.4512858
• Log P: 5.191066
• Molar Refractivity: 90.0343 cm^3
• Polarizability: 34.529655 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H951080

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)