Structure Database (LMSD)

Common Name
8S-HEPE
Systematic Name
8S-hydroxy-5Z,9E,11Z,14Z,17Z-eicosapentaenoic acid
Synonyms
LM ID
LMFA03070003
Formula
Exact Mass
Calculate m/z
318.219495
Sum Composition
Status
Curated


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

LIPIDBANK ID
DFA8120
PubChem CID
Cayman ID

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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