(5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid

• ChemBase ID: 125174
• Molecular Formular: C20H32O3
• Molecular Mass: 320.46628
• Monoisotopic Mass: 320.23514488
• SMILES: CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)O
• Canonical SMILES: CCCCC/C=C\C[C@@H](/C=C/C=C\C/C=C\CCCC(=O)O)O
• InChI: InChI=1S/C20H32O3/c1-2-3-4-5-10-13-16-19(21)17-14-11-8-6-7-9-12-15-18-20(22)23/h7-11,13-14,17,19,21H,2-6,12,15-16,18H2,1H3,(H,22,23)/b9-7-,11-8-,13-10-,17-14+/t19-/m0/s1
• InChIKey: ZNHVWPKMFKADKW-LQWMCKPYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5Z,8Z,10E,12S,14Z)-12-hydroxyicosa-5,8,10,14-tetraenoic acid
• IUPAC Traditional name: 12S-hete
• Synonyms: 12-HETE; 12(S)-HETE; 12-Hydroxyeicosatetraenoic acid; [S-(E,Z,Z,Z)]-12-Hydroxy-5,8,10,14-eicosatetraenoic Acid; 12-Hydroxy-5,8,10,14-eicosatetraenoic Acid; 12-Hydroxyeicosatetraenoic Acid; 12-L-Hydroxy-5,8,10,14-eicosatetraenoic Acid; 12(S)-Hydroxy (5Z,8Z,10E,14Z)-Eicosatetraenoic Acid

Database IDs

• CAS Number: 54397-83-0
• PubChem SID: 162219524
• PubChem CID: 5283155
• CHEBI ID: 34146
• Chemspider ID: 4446279
• Wikipedia Title: 12-Hydroxyeicosatetraenoic_acid

CALCULATED PROPERTIES

• Acid pKa: 4.889631
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 4.6512523
• LogD (pH = 7.4): 2.8843422
• Log P: 5.35636
• Molar Refractivity: 101.4695 cm^3
• Polarizability: 37.740055 Å^3
• Polar Surface Area: 57.53 Å^2
• Rotatable Bonds: 14
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - H825285

A fatty acid metabolite of arachidonic acid (A765000). Potential biomarker for asthma monitoring and diagnosis. Stimulates protein kinase C-mediated release of cathepsin B from malignant cells. Used in the study of mechanisms controlling cell cycle arrest

REFERENCES

• Nording, M.L. et al.: IEEE Sensors J., 10, 123 (2010)
• Pidgeon, G.P. et al.: Canc. Res., 62, 2721 (2010)
• Honn, K.V. et al.: Exp. Cell Res., 214, 120 (2010)
• Feldstein, A.E. et al.: J. Lipid Res., 51, 3046 (2010)