Structure Database (LMSD)
Common Name
(+/-)-8-HEPE
Systematic Name
(+/-)-8-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic acid
Synonyms
3D model of (+/-)-8-HEPE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
(±)8-HEPE is produced by non-enzymatic oxidation of EPA. It contains equal amounts of 8(S)-HEPE and 8(R)-HEPE. The ability of (±)8-HEPE to induce hatching of E. modestus and B. balanoides eggs is probably due to the presence of the 8(R) isomer within the racemic mixture.1,2
This information has been provided by Cayman Chemical
References
1. Hill, E.M., and Holland, D.L. Identification and egg hatching activity of monohydroxy fatty acid eicosanoids in the barnacle Balanus balanoides. Proc. R. Soc. Lond. B Biol. Sci. 247, 41-46 (1991).
2. Shing, T.K.M., Gibson, K.H., Wiley, J.R., et al. First total synthesis of a barnacle hatching factor 8(R)-hydroxy-eicosa-5(Z),9(E),11(Z)-pentaenoic acid. Tetrahedron Lett. 35, 1067-1070 (1994).
String Representations
InChiKey (Click to copy)
WLOUCHKFBGGNEB-GXIKJMEPSA-N
InChi (Click to copy)
InChI=1S/C20H30O3/c1-2-3-4-5-6-7-8-9-10-13-16-19(21)17-14-11-12-15-18-20(22)23/h3-4,6-7,9-11,13-14,16,19,21H,2,5,8,12,15,17-18H2,1H3,(H,22,23)/b4-3-,7-6-,10-9-,14-11-,16-13+
SMILES (Click to copy)
C(CCC/C=C\CC(O)/C=C/C=C\C/C=C\C/C=C\CC)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
23
Rings
0
Aromatic Rings
0
Rotatable Bonds
13
Van der Waals Molecular Volume
365.09
Topological Polar Surface Area
57.53
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
3
logP
5.25
Molar Refractivity
97.85
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Updated at
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