LBF20406HP03

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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	DFA8081
LipidMaps	-
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20406HP03

9-Hydroperoxy-5,7,11,14-Eicosatetraenoic Acid
Structural Information
Systematic Name	9-Hydroperoxy-5,7,11,14-Eicosatetraenoic Acid/9-Hydroperoxy-5,7,11,14-Eicosatetraenoate
Common Name	9-Hydroperoxy-5,7,11,14-Eicosatetraenoic Acid 9-Hydroperoxy-5,7,11,14-Eicosatetraenoate
Symbol
Formula	C20H32O4
Exact Mass	336.23005951199997
Average Mass	336.46567999999996
SMILES	C(CC=CCC=CCC(OO)C=CC=CCCCC(O)=O)CCC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility
Source	Autooxidation of arachidonic acid Terao_J et al. Yamagata_S et al. Porter_NA et al.. Oxidation of arachidonic acid by singlet-oxygen Terao_J et al. Porter_NA et al.. Reaction products between arachidonic acid and lipoxygenase from living cells(9-HPETE).
Chemical Synthesis
Metabolism
Biological Activity	9-HPETE generated by 9-lipoxygenase is enzymatically converted to bioactive compounds such as leukotriene and HETE.
Genetic Information
Note	Isomerization of hydroperoxides : Both 5- and 15-hydroperoxide were generated predominantly by autooxidation or singlet-oxygen mediated oxidation Terao_J et al. Yamagata_S et al. Peers_KE et al.. However, the proportion of each isomer generated become almost equal by supplementation of hydrogen donor such as tocopherol Porter_NA et al. Terao_J et al. Peers_KE et al..
Spectral Information
Mass Spectra	GC-EI-MS(Me-ester; after reduction and TMS) TeraoJet al. TeraoJet al. RabinovitchHet al.: m/e=406[M]; 316[M-HOTMS]; 255[SMTO=CHCH=CHCH=CH(CH2)3COOCH3]; GC-EI-MS(Me-ester; after reduction and TBDMS)(114): m/e=448[M], 391[M-(CH3)3C]; GC-EI-MS(Me-ester; after reduction hydrogenation and TMS)
UV Spectra	UV Porter_NA et al. conjugated diene: λ max=235nm, UV(Me-ester) TeraoJet al. conjugated diene: λ max=232.5nm, UV(Me-ester; after reduction) Porter_NA et al. conjugated cis, trans diene: λ max=236nm, conjugated trans, trans diene: λ max=232.
IR Spectra	IR(me-ester; after reduction) Porter_NA et al. conjugated cis, trans diene: 985, 950cm-1, conjugated trans, trans diene: 989cm-1
NMR Spectra
Other Spectra	Rogenation and TBDMS) TeraoJet al.
Chromatograms

Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF20406HP03 See above. Peers_KE et al. 1983 n.a. LBF20406HP03 See above. Porter_NA et al. 1981 n.a. LBF20406HP03 See above. Porter_NA et al. 1979 n.a. LBF20406HP03 See above. Porter_NA et al. 1979 n.a. LBF20406HP03 See above. Rabinovitch_H et al. 1981 n.a. LBF20406HP03 See above. Terao_J et al. 1981 n.a. LBF20406HP03 See above. Terao_J et al. 1981 n.a. LBF20406HP03 See above. Yamagata_S et al. 1983