LIPID MAPS

Structure Database (LMSD)

View 3D

Download as... MDLMOL SDF CSV TSV PNG

Common Name

12-oxo-LTB4

Systematic Name

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

Synonyms

12-oxo-Leukotriene B4

LM ID

LMFA03020024

Formula

C₂₀H₃₀O₄

Exact Mass

Calculate m/z

334.21441

Sum Composition

FA 20:5;O2

Status

Curated

Show lipids differing only in stereochemistry/bond geometry

View ion mobility data

Classification

Biological Context

12-oxo LTB4 is an initial metabolite of LTB4 formed via the LTB4 12-hydroxydehydrogenase pathway.^1,2,3 It is rapidly converted to 10,11-dihydro-12-oxo-LTB4, followed by reduction of the 12-oxo group to give 10,11-dihydro-LTB4.2 12-oxo-LTB4 (EC50 = 33 nM) is about 70-fold less potent than LTB4 (EC50 = 0.46 nM) at stimulating Ca2+ mobilization in human neutrophils.⁴ It is also significantly less potent than LTB4 at stimulating neutrophil migration with EC50 values of 170 and 2.7 nM for 12-oxo-LTB4 and LTB4, respectively.⁴

This information has been provided by Cayman Chemical

References

1. Wheelan, P., Zirrolli, J.A., Morelli, J.G., et al. Metabolism of leukotriene B4 by cultural human keratinocytes. Formation of glutathione conjugates and dihydro metabolites. The Journal of Biological Chemisty 268, 25439-25448 (1993).

2. Yokomizo, T., Izumi, T., Takahashi, T., et al. Enzymatic inactivation of leukotriene B4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12-hydroxydehydrogenase. The Journal of Biological Chemisty 268, 18128-18135 (1993).

3. Powell, W.S., Rokach, J., Khanapure, S.P., et al. Effects of metabolites of leukotriene B4 on human neutrophil migration and cytosolic calcium levels. J. Pharmacol. Exp. Ther. 276(2), 728-736 (1996).

4. Wainwright, S.L., and Powell, W.S. Mechanism for the formation of dihydro metabolites of 12-hydroxyeicosanoids conversion of leukotriene B4 and 12-hydroxy-5,8,10,14-eicosatetraenoic acid to 12-oxo intermediates. The Journal of Biological Chemisty 266(31), 20899-20906 (1991).

References

Taxonomy Information

Curated from

NCBI taxonomy class

Reference

Sus scrofa (#9823)

Mammalia (#40674)

Enzymatic inactivation of leukotriene B4 by a novel enzyme found in the porcine kidney. Purification and properties of leukotriene B4 12-hydroxydehydrogenase.,
J Biol Chem, 1993

Pubmed ID: 8394361

String Representations

InChiKey (Click to copy)

SJVWVCVZWMJXOK-NOJHDUNKSA-N

InChi (Click to copy)

InChI=1S/C20H30O4/c1-2-3-4-5-6-9-13-18(21)14-10-7-8-11-15-19(22)16-12-17-20(23)24/h6-11,14-15,19,22H,2-5,12-13,16-17H2,1H3,(H,23,24)/b8-7+,9-6-,14-10+,15-11-/t19-/m1/s1

SMILES (Click to copy)

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