Structure database (LMSD)

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LM IDLMFA03070059
Common Name5R-HpEPE
Systematic Name5R-hydroperoxy-6E,8Z,11Z,14Z,17Z-eicosapentaenoic acid
Synonyms-
Exact Mass
334.2144 (neutral)    Calculate m/z:
FormulaC20H30O4
CategoryFatty Acyls [FA]
Main ClassEicosanoids [FA03]
Sub ClassHydroxy/hydroperoxyeicosapentaenoic acids [FA0307]
AbbrevFA 20:5;O2
PubChem CID-
InChIKeyNKXYOIJDQPQELO-CBVHGRPESA-N  Show lipids differing only in stereochemistry/bond geometry
InChI
InChI=1S/C20H30O4/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-16-19(24-23)17-15-18-20(21)22/h3-4,6-7,9-10,12-14,16,19,23H,2,5,8,11,15,17-18H2,1H3,(H,21,22)/b4-3-,7-6-,10-9-,13-12-,16-14+/t19-/m0/s1
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SMILES
C(CCC[C@@H](OO)/C=C/C=C\C/C=C\C/C=C\C/C=C\CC)(=O)O
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StatusActive
ReferencesLOX-Induced Lipid Peroxidation Mechanism Responsible for the Detrimental Effect of Marine Diatoms on Zooplankton Grazers.
ChemBioChem 2007
DOI: 10.1002/cbic.200700269
PMID: 17886321
Calculated physicochemical properties (?):
 Heavy Atoms24Rings0Aromatic Rings0Rotatable Bonds14
 van der Waals
Molecular Volume
373.88Topological Polar
Surface Area
66.76Hydrogen
Bond Donors
2Hydrogen
Bond Acceptors
4
 logP5.92Molar
Refractivity
99.21