(5S,6E,8Z)-5,18-dihydroxyoctadeca-6,8-dienoic acid

• ChemBase ID: 167856
• Molecular Formular: C18H32O4
• Molecular Mass: 312.44428
• Monoisotopic Mass: 312.2300595
• SMILES: C(=C\CCCCCCCCCO)\C=C\[C@H](CCCC(=O)O)O
• Canonical SMILES: OCCCCCCCCC/C=C\C=C\[C@H](CCCC(=O)O)O
• InChI: InChI=1S/C18H32O4/c19-16-11-9-7-5-3-1-2-4-6-8-10-13-17(20)14-12-15-18(21)22/h6,8,10,13,17,19-20H,1-5,7,9,11-12,14-16H2,(H,21,22)/b8-6-,13-10+/t17-/m1/s1
• InChIKey: RPFAXJQGBOULPA-CQLUAUNVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5S,6E,8Z)-5,18-dihydroxyoctadeca-6,8-dienoic acid
• IUPAC Traditional name: (5S,6E,8Z)-5,18-dihydroxyoctadeca-6,8-dienoic acid
• Synonyms: 5,18-diHODE; 5S,18-Dihydroxy-(6E,8Z)-octadecadienoic Acid; (5S,6E,8Z)-5,18-Dihydroxy-6,8-octadecadienoic Acid

Database IDs

• CAS Number: 1021188-24-8
• PubChem SID: 162261989
• PubChem CID: 71316263

CALCULATED PROPERTIES

• Acid pKa: 4.5841017
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): 2.7897966
• LogD (pH = 7.4): 1.0146072
• Log P: 3.7543871
• Molar Refractivity: 91.963 cm^3
• Polarizability: 35.147522 Å^3
• Polar Surface Area: 77.76 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D454140

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)