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Structure Database (LMSD)

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Common Name

12-epi-LTB4

Systematic Name

5S,12S-dihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid

Synonyms

12-epi-Leukotriene B4

LM ID

LMFA03020015

Formula

C₂₀H₃₂O₄

Exact Mass

Calculate m/z

336.23006

Sum Composition

FA 20:4;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

Classification

Biological Context

12-epi LTB4 is an isomer which would not be expected to occur in either non-enzymatic hydrolysis products, or in the enzymatic products of LTA4 hydrolase.¹ Compared to LTB4, 12-epi LTB4 has significantly reduced activity for the LTB4 receptor on human neutrophils (IC50 of 7.5 mM),2 and on guinea pig lung membranes with a (Ki of 4.7 mM).³ 12-epi LTB4 is an weak agonist at both the recombinant human BLT1 and BLT2 receptors, requiring approximately 10 mM for full activation of the receptor.⁴

This information has been provided by Cayman Chemical

References

1. Sala, A., Bolla, M., Zarini, S., et al. Release of leukotriene A4 versus leukotriene B4 from human polymorphonuclear leukocytes. The Journal of Biological Chemisty 271, 17944-17948 (1996).

2. Yokomizo, T., Kato, K., Hagiya, H., et al. Hydroxyeicosanoids bind to and activate the low affinity leukotriene B4 receptor, BLT2. The Journal of Biological Chemisty 276(15), 12454-12459 (2001).

3. Cristol, J.P., Provençal, B., Borgeat, P., et al. Characterization of leukotriene B4 binding sites on guinea pig lung macrophages. J. Pharmacol. Exp. Ther. 247(3), 1199-1203 (1988).

4. Jackson, R.H., Morrissey, M.M., Sills, M.A., et al. Comparison of antagonist and agonist binding to the leukotriene B4 receptor on intact human polymorphonuclear neutrophils (PMN). J. Pharmacol. Exp. Ther. 262(1), 80-89 (1992).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Homo sapiens (#9606)

Mammalia (#40674)

Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010

Pubmed ID: 20671299

DOI: 10.1194/jlr.M009449

String Representations

InChiKey (Click to copy)

VNYSSYRCGWBHLG-CBBLYLIKSA-N

InChi (Click to copy)

InChI=1S/C20H32O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,18-19,21-22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t18-,19+/m0/s1

SMILES (Click to copy)

C([C@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(O)=O)/C=C\CCCCC