ethyl (5Z,8Z,11Z,14Z,17Z)-(19,19,20,20,20-2H5)icosa-5,8,11,14,17-pentaenoate

• ChemBase ID: 167956
• Molecular Formular: C22H34O2
• Molecular Mass: 330.50416
• Monoisotopic Mass: 330.25588033
• SMILES: C(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)C(=O)OCC
• Canonical SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)OCC
• InChI: InChI=1S/C22H34O2/c1-3-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24-4-2/h5-6,8-9,11-12,14-15,17-18H,3-4,7,10,13,16,19-21H2,1-2H3/b6-5-,9-8-,12-11-,15-14-,18-17-
• InChIKey: SSQPWTVBQMWLSZ-AAQCHOMXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (5Z,8Z,11Z,14Z,17Z)-(19,19,20,20,20-^2H₅)icosa-5,8,11,14,17-pentaenoate
• IUPAC Traditional name: ethyl (5Z,8Z,11Z,14Z,17Z)-(19,19,20,20,20-^2H₅)icosa-5,8,11,14,17-pentaenoate
• Synonyms: (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic Acid-d5 Ethyl Ester; (all-Z)-5,8,11,14,17-Eicosapentaenoic Acid-d5 Ethyl Ester; Epadel; Ethyl Eicosapentaenoate-d5; Timnodonic Acid-d5 Ethyl Ester; cis-Eicosapentaenoic Acid-d5 Ethyl Ester; Eicosapentaenoic Acid-d5 Ethyl Ester

Database IDs

• PubChem SID: 162262089
• PubChem CID: 46781442

CALCULATED PROPERTIES

• H Acceptors: 1
• H Donor: 0
• LogD (pH = 5.5): 6.727951
• LogD (pH = 7.4): 6.727951
• Log P: 6.727951
• Molar Refractivity: 110.5883 cm^3
• Polarizability: 40.872074 Å^3
• Polar Surface Area: 26.3 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E477807

Important polyunsaturated fatty acid of the marine food chain that serves as a precursor for the prostaglandin-3 and thromboxane-3 families. It differs from arachidonic acid (the eicosatetraenoic acid that is a precursor for the prostaglandin and thrombox

REFERENCES

• Bergstrom, S., et al.: J. Biol. Chem., 239, PC 4006 (1964)
• Srivastava, K.C., et al.: Biochem. Exp. Biol., 16, 317 (1964)
• Kremer, J.M., et al.: Ann. Intern. Med., 106, 497 (1964)
• DiGiacomo, R.A., et al.: Am. J. Med., 86, 158 (1964)