(8Z,11Z,14Z)-(8,9,11,12,14,15-2H6)icosa-8,11,14-trienoic acid

• ChemBase ID: 167959
• Molecular Formular: C20H34O2
• Molecular Mass: 306.48276
• Monoisotopic Mass: 306.25588033
• SMILES: C(=C\C/C=C\C/C=C\CCCCC)CCCCCCC(=O)O
• Canonical SMILES: CCCCC/C=C\C/C=C\C/C=CCCCCCCC(=O)O
• InChI: InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-
• InChIKey: HOBAELRKJCKHQD-QNEBEIHSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (8Z,11Z,14Z)-(8,9,11,12,14,15-^2H₆)icosa-8,11,14-trienoic acid
• IUPAC Traditional name: (8Z,11Z,14Z)-(8,9,11,12,14,15-^2H₆)icosa-8,11,14-trienoic acid
• Synonyms: (8Z,11Z,14Z)-8,11,14-Eicosatrienoic Acid-d6; (Z,Z,Z)-8,11,14-Eicosatrienoic Acid-d6; 8,11,14-Eicosatrienoic Acid-d6; 8,11,14-all-cis-Eicosatrienoic Acid-d6; Bishomo-γ-linolenic Acid-d6; DGLA-d6; Dihomo-γ-linolenic Acid-d6; Ro 12-1989-d6; all-cis-8,11,14-Eicosatrienoic Acid-d6; cis-8,cis-11,cis-14-Eicosatrienoic Acid-d6; γ-Homolinolenic Acid-d6; cis-8,11,14-Eicosatrienoic Acid-d6

Database IDs

• PubChem SID: 162262092
• PubChem CID: 71316311

CALCULATED PROPERTIES

• Acid pKa: 4.8858237
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 6.24093
• LogD (pH = 7.4): 4.4736137
• Log P: 6.9490924
• Molar Refractivity: 98.8374 cm^3
• Polarizability: 37.38399 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - E477932

Labelled cis-8,11,14-Eicosatrienoic acid (E477930). cis-8,11,14-Eicosatrienoic acid is a fatty acid which has selective tumoricidal action.

REFERENCES

• Das, U., et al.: Cancer Lett., 56, 235 (1991)
• Rudra, P., et al.: Anticancer Res., 21, 29 (1991)
• Menendez, J., et al.: Breast Cancer Res. Treat., 72, 203 (1991)