(6Z,9Z,12Z,15Z,18Z)-henicosa-6,9,12,15,18-pentaenoic acid

• ChemBase ID: 169848
• Molecular Formular: C21H32O2
• Molecular Mass: 316.47758
• Monoisotopic Mass: 316.24023026
• SMILES: C(/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O)C
• Canonical SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O
• InChI: InChI=1S/C21H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21(22)23/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-20H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,13-12-,16-15-
• InChIKey: OQOCQFSPEWCSDO-JLNKQSITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (6Z,9Z,12Z,15Z,18Z)-henicosa-6,9,12,15,18-pentaenoic acid
• IUPAC Traditional name: (6Z,9Z,12Z,15Z,18Z)-henicosa-6,9,12,15,18-pentaenoic acid
• Synonyms: (6Z,9Z,12Z,15Z,18Z)-6,9,12,15,18-Heneicosapentaenoic Acid; (all-Z)-6,9,12,15,18-Heneicosapentaenoic Acid

Database IDs

• CAS Number: 24257-10-1
• PubChem SID: 162263980
• PubChem CID: 11998573

CALCULATED PROPERTIES

• Acid pKa: 4.922493
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.9908624
• LogD (pH = 7.4): 4.227784
• Log P: 6.669818
• Molar Refractivity: 105.6716 cm^3
• Polarizability: 38.76064 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H245600

An 21-carbon, ω-3 fatty acid which is a dietary precursor to eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA). It is administered in a high dose for pain relief.

REFERENCES

• Ng, L, et al.: Anal. Biochem., 167, 47 (1987)
• Dunstan, G., et al.: Lipids, 28, 937 (1987)