Structure Database (LMSD)
Common Name
15S-HpEPE
Systematic Name
15S-hydroperoxy-5Z,8Z,11Z,13E,17Z-eicosapentaenoic acid
Synonyms
LM ID
LMFA03070013
Formula
Exact Mass
Calculate m/z
334.21441
Sum Composition
Status
Curated
3D model of 15S-HpEPE
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
15(S)-HpEPE is an active metabolite of the ω-3 fatty acid eicosapentaenoic acid (EPA).1 It is formed from EPA by 15-lipoxygenase (15-LO). 15(S)-HpEPE (0.01, 0.3, and 1 µM) inhibits IL-1β-induced increases in the levels of COX-2 in human pulmonary microvascular endothelial cells (HPMECs).2
This information has been provided by Cayman Chemical
References
1. Ait-Said, F., Elalamy, I., Werts, C., et al. Inhibition by eicosapentaenoic acid of IL-1β-induced PGHS-2 expression in human microvascular endothelial cells: Involvement of lipoxygenase-derived metabolites and p38 MAPK pathway. Biochim. Biophys. Acta 1631(1), 77-84 (2003).
2. Jin, J., Boeglin, W.E., and Brash, A.R. Analysis of 12/15-lipoxygenase metabolism of EPA and DHA with special attention to authentication of docosatrienes. J. Lipid Res. 62, 100088 (2021).
String Representations
InChiKey (Click to copy)
FPMFSFWYWZLDKP-XWJJKCKWSA-N
InChi (Click to copy)
InChI=1S/C20H30O4/c1-2-3-13-16-19(24-23)17-14-11-9-7-5-4-6-8-10-12-15-18-20(21)22/h3-5,8-11,13-14,17,19,23H,2,6-7,12,15-16,18H2,1H3,(H,21,22)/b5-4-,10-8-,11-9-,13-3-,17-14+
SMILES (Click to copy)
C(/C/C=C\C=C\C(OO)C/C=C\CC)=C/C/C=C\CCCC(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
24
Rings
0
Aromatic Rings
0
Rotatable Bonds
14
Van der Waals Molecular Volume
373.88
Topological Polar Surface Area
66.76
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
5.92
Molar Refractivity
99.21
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Created at
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Updated at
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