Structure Database (LMSD)
Common Name
8S-HEPE
Systematic Name
8S-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic acid
Synonyms
3D model of 8S-HEPE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
8(S)-HEPE is a monohydroxy fatty acid produced by lipoxygenase oxidation of EPA. It acts to promote hatching of barnacle eggs at 10 nM, although it is not clearly identified as the natural egg hatching factor.1
This information has been provided by Cayman Chemical
References
1. Hill, E.M., Holland, D.L., Gibson, K.H., et al. Identification and hatching factor activity of monohydroxyeicosapentaenoic acid in homogenates of the barnacle Elminius modestus. Proc. R. Soc. Lond. B Biol. Sci. 234, 455-461 (1988).
String Representations
InChiKey (Click to copy)
WLOUCHKFBGGNEB-CHGUASJCSA-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+/t19-/m1/s1
SMILES (Click to copy)
C(/C=C/[C@@H](O)C/C=C\CCCC(=O)O)=C/C/C=C\C/C=C\CC
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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