Structure Database (LMSD)

Common Name
11R-HEPE
Systematic Name
11R-hydroxy-5Z,8Z,12E,14Z,17Z-eicosapentaenoic acid
Synonyms
LM ID
LMFA03070005
Formula
C20H30O3
Exact Mass
Calculate m/z
318.219495
Sum Composition
FA 20:5;O
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Hydroxy/hydroperoxyeicosapentaenoic acids [FA0307]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]

Biological Context

11(R)-HEPE is produced by the oxidation of EPA by 11(R)-LO. This enzymatic activity and the resulting 11(R)-hydroxy acid have been isolated from the sea urchin S. purpuratus.1

This information has been provided by Cayman Chemical

References

1. Hawkins, D.J., and Brash, A.R. Eggs of the sea urchin, Strongylocentrotus purpuratus, contain a prominent (11R) and (12R) lipoxygenase activity. The Journal of Biological Chemisty 262(16), 7629-7634 (1987).

String Representations

InChiKey (Click to copy)
IDEHSDHMEMMYIR-DJWFCICMSA-N
InChi (Click to copy)
InChI=1S/C20H30O3/c1-2-3-4-5-7-10-13-16-19(21)17-14-11-8-6-9-12-15-18-20(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-,9-6-,10-7-,14-11-,16-13+/t19-/m0/s1
SMILES (Click to copy)
C(/C[C@@H](O)/C=C/C=C\C/C=C\CC)=C/C/C=C\CCCC(=O)O

Other Databases

HMDB ID
HMDB0012534
CHEBI ID
91264
LIPIDBANK ID
DFA8122
PubChem CID
5283188
Cayman ID
32505

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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