LBF20503HP01

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Fatty acid (脂肪酸)

Glycerolipid (グリセロ脂質)

Sphingolipid (スフィンゴ脂質)

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Upper classes: LB LBF

IDs and Links
LipidBank	DFA8096
LipidMaps	-
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20503HP01

5-Hydroperoxy-6,8,11,14,17-eicosapentaenoic acid
Structural Information
Systematic Name	5-Hydroperoxy-6,8,11,14,17-eicosapentaenoic acid
Common Name	5-Hydroperoxy-6,8,11,14,17-eicosapentaenoic acid
Symbol
Formula	C20H30O4
Exact Mass	334.21440944799997
Average Mass	334.4498
SMILES	C(CC=CCC=CCC=CC=CC(OO)CCCC(O)=O)=CCC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	Autooxidation of icosapentaenoate Yamauchi_R et al.. Oxidation of icosapentaenoate by singlet-oxygen Yamauchi_R et al.. Oxidation of icosapentaenoate in the presence of mioglobin. It is produced from icosapentaenoate by 5-lipoxygenate of arachidonic acid Lee_TH et al..
Chemical Synthesis
Metabolism
Biological Activity	5-Hydroperoxide derivative of icosapentaenoic acid, which is produced concomitantly with action of 15-lipoxygenase against arachidonate, is further metabolized to hydroxylate and leukotrienes, but their physiological activities remain to be clarified Lee_TH et al..
Genetic Information
Note	Isomerization of hydroperoxides generated from icosapentaenoete by autooxidation: the proportion of 5-, 18-isomer (outer hydroperoxides) is higher than that of other isomer (8-,9-,11-,12-,14-,15-isomer[inner hydroperoxides]).
Spectral Information
Mass Spectra	GC-EI-MS(Me-ester; after reduction and TMS-derivatization) YamauchiRet al. OchiKet al. FurukawaMet al. HammarstromS: m/e=404[M]; 389[M-CH3]; 314[M-HOTMS]; 303[M-(CH2)3COOCH3]; 255[M-CH2CH=CH(CH2)3CH3]; 213[303-HOTMS]; 203[SMTO=CH(CH2)3COOCH3]
UV Spectra	UV(Me-ester) YamauchiRet al.: conjugated diene: λ max=235.5nm; UV(after reduction) HammarstromS: conjugated diene: λ =max=235nm
IR Spectra	IR(Me-ester) YamauchiRet al.: OOH group: 3400cm-1
NMR Spectra	1H-NMR YamauchiRet al.: OOH proton: 8.5ppm
Other Spectra
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF20503HP01 See above. Furukawa_M et al. 1984 n.a. LBF20503HP01 See above. Hammarstrom_S 1983 n.a. LBF20503HP01 See above. Lee_TH et al. 1985 n.a. LBF20503HP01 See above. Ochi_K et al. 1983 n.a. LBF20503HP01 See above. Yamauchi_R et al. 1983 n.a. LBF20503HP01 See above. Yamauchi_R et al. 1985