LBF20407LX01

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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	DFA8153
LipidMaps	LMFA03040001
CAS	89663-86-5
KEGG	{{{KEGG}}}
KNApSAcK	{{{KNApSAcK}}}
mol	LBF20407LX01

Lipoxin A4
Structural Information
Systematic Name	(5S,6R,15S) -Trihydroxy- (trans-7,trans-9,cis-11,trans-13) -eicosatetraenoic acid
Common Name	Lipoxin A4 (5S,6R,15S) -Trihydroxy- (7E,9E,11Z,13E) -eicosatetraenoic acid
Symbol	LXA4
Formula	C20H32O5
Exact Mass	352.224974134
Average Mass	352.46508
SMILES	C(CCC(C=CC=CC=CC=CC(O)C(O)CCCC(O)=O)O)CC
Physicochemical Information
Melting Point
Boiling Point
Density
Optical Rotation
Refractive Index
Solubility	diethyl ether, methanol. AdamsJet al.
Source	LXA4 is formed in vitro by a number of mechanisms from arachidonic acid, 15-HpETE, and leukotriene A4 (LTA4 ) Edenius_C et al. Serhan_CN et al.. Lipoxin A4 is produced by activated leukocytes Serhan_CN , Brady_HR et al..
Chemical Synthesis	Table0001 Adams_J et al.
Metabolism	Dual lipoxygenation pathways are considered for lipoxin A4 synthesis from arachidonic acid; either 15-lipoxygenase and 5-lipoxygenase in leukocytes or 5-lipoxygenase in leukocytes and 12-lipoxygenase in platelets Serhan_CN .
Biological Activity	LXA is equipotent to LTB in inducing superoxide generation in human neutrophils (0.1 mu M) Serhan_CN et al.. LXA4 is associated with several other biological functions including leukocyte activation, chemotaxis promotion, natural killer cell inhibition, and monocyte migration and adhesion Serhan_CN et al. Ramstedt_U et al. Maddox_JF et al.. Lipoxin A4 is either vasoconstrictive or vasodilatory, and has immunoregulatory activities blocking the cytotoxic action of NK cell, inhibiting adherence and chemotaxis of leukocytes induced by FMLP, PAF or leukotriene B4 Serhan_CN .
Genetic Information	cDNA for a receptor specific for lipoxin A4 was cloned out of orphan cDNAs Fiore_S et al..
Note
Spectral Information
Mass Spectra	TMS-derivs. ; 582(M+), 492, 482, 379, 289, 203, 173, 171. Serhan_CN et al.
UV Spectra	λ max: 302nm ε : 50,000, λ MeOHmax: 287,301 (ε 50,000) : 316nm AdamsJet al., Serhan_CN et al.
IR Spectra
NMR Spectra	1H-NMR(250MHz, 5% CD3OD/D2O ) : δ 0.8-0.9(brt, 3H), 1.2-1.8(m, 14H), 2.1-2.3(m, 2H), 3.4-3.6(m, 1H), 3.95-4.05(t, J=6.8Hz, 1H), 4.1-4.2(q, J=7.1Hz, 1H), 5.6-5.85(seven lines, 2H), 5.9-6.1(m, 2H), 6.2-6.45(m, 2H), 6.6-6.8(m, 2H). AdamsJet al.
Other Spectra
Chromatograms

Reported Metabolites, References

Biospecies ID Compound Name Reference Comment n.a. LBF20407LX01 See above. Adams_J et al. 1985 n.a. LBF20407LX01 See above. Brady_HR et al. 1996 n.a. LBF20407LX01 See above. Edenius_C et al. 1991 n.a. LBF20407LX01 See above. Fiore_S et al. 1994 n.a. LBF20407LX01 See above. Maddox_JF et al. 1996 n.a. LBF20407LX01 See above. Ramstedt_U et al. 1987 n.a. LBF20407LX01 See above. Serhan_CN 1994 n.a. LBF20407LX01 See above. Serhan_CN et al. 1984 n.a. LBF20407LX01 See above. Serhan_CN et al. 1984 n.a. LBF20407LX01 See above. Serhan_CN et al. 1986

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