LBF20306HX03

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Fatty acid (脂肪酸)

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Upper classes: LB LBF

IDs and Links
LipidBank	XPR5001
LipidMaps	LMFA03090005
CAS
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20306HX03

Hepoxilin A3
Structural Information
Systematic Name	8-Hydroxy- (11S,12S)-epoxy- (cis-5,trans-9,cis-14) -eicosatrienoic acid
Common Name	Hepoxilin A3 8-Hydroxy- (11S,12S)-epoxy- (5Z,9E,14Z) -eicosatrienoic acid 8-Hydroxy-11,12 (S,S) -epoxyeicosa-5,14 (Z,Z) ,9 (E) -trienoic acid
Symbol	HxA3
Formula	C20H32O4
Exact Mass	336.23005951199997
Average Mass	336.46567999999996
SMILES	C(=C[C@@H](O)CC=CCCCC(O)=O)[C@@H](O1)[C@@H]1CC=CCCCCC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility	DIETHYL ETHER Pace-Asciak_CR et al.
Source	Hepoxilin A3 together with hepoxilin B3 is produced from arachidonic acid or more directly from 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid in various animal tissues including brain, pineal gland, pancreas and skin Pace-Asciak_CR .
Chemical Synthesis	Corey_EJ et al.
Metabolism	The presence of hepoxilin synthase was suggested by a finding that intact cells (skin) and tissue slices (brain hippocampus and pineal gland) transformed 12(S)-hydroperoxy-5,8,10,14-eicosatetraenoic acid to hepoxilins A3 and B3, but tissue boiling inhibited the hepoxilin production Pace-Asciak_CR et al..
Biological Activity	As the biological activities of hepoxilin A3, insulin secretion from pancreas is stimulated, the enhanced vascular permeability by bradykinin is potentiated, hyperpolarization in hippocampal CA1 neurons is caused, and platelet aggregation is inhibited. At the molecular level hepoxilin A3 releases intracellular calcium, and opens potassium channel. Hepoxilin-specific binding proteins are present in human neutrophils Pace-Asciak_CR .
Genetic Information
Note
Spectral Information
Mass Spectra	METHYL ESTER TRIS-TMS ETHER ; m/e 422(M+), 407, 391, 332, 311, 282, 269(base peak) Walker_IC et al.
UV Spectra
IR Spectra
NMR Spectra
Other Spectra
Chromatograms

Reported Metabolites, References
Biospecies ID Compound Name Reference Comment n.a. LBF20306HX03 See above. Corey_EJ et al. 1984 n.a. LBF20306HX03 See above. Pace-Asciak_CR 1994 n.a. LBF20306HX03 See above. Pace-Asciak_CR et al. 1983 n.a. LBF20306HX03 See above. Pace-Asciak_CR et al. 1995 n.a. LBF20306HX03 See above. Walker_IC et al. 1979