(5Z,8Z,11Z,14Z,17Z)-(19,19,20,20,20-2H5)icosa-5,8,11,14,17-pentaenoic acid

• ChemBase ID: 167954
• Molecular Formular: C20H30O2
• Molecular Mass: 302.451
• Monoisotopic Mass: 302.2245802
• SMILES: C(CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CC)C(=O)O
• Canonical SMILES: CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)O
• InChI: InChI=1S/C20H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h3-4,6-7,9-10,12-13,15-16H,2,5,8,11,14,17-19H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-15-
• InChIKey: JAZBEHYOTPTENJ-JLNKQSITSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z,8Z,11Z,14Z,17Z)-(19,19,20,20,20-^2H₅)icosa-5,8,11,14,17-pentaenoic acid
• IUPAC Traditional name: (5Z,8Z,11Z,14Z,17Z)-(19,19,20,20,20-^2H₅)icosa-5,8,11,14,17-pentaenoic acid
• Synonyms: Incromega E 7010SR-d5; Ropufa 70-d5; Timnodonic Acid-d5; Eicosapentaenoic Acid-d5; (5Z,8Z,11Z,14Z,17Z)-5,8,11,14,17-Eicosapentaenoic Acid-d5; (all-Z)-5,8,11,14,17-Eicosapentaenoic Acid-d5; EPA-d5; EPA 45G-d5; Icosapent-d5; Icosapentaenoic Acid-d5

Database IDs

• PubChem SID: 162262087
• PubChem CID: 24778482

CALCULATED PROPERTIES

• Acid pKa: 4.819772
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 5.4632735
• LogD (pH = 7.4): 3.6901412
• Log P: 6.2252493
• Molar Refractivity: 101.0706 cm^3
• Polarizability: 36.914207 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Colorless Oil

DETAILS

Toronto Research Chemicals - E477802

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)