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Structure Database (LMSD)

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Common Name

20-hydroxy LTB4

Systematic Name

5S,12R,20-trihydroxy-6Z,8E,10E,14Z-eicosatetraenoic acid

Synonyms

20-hydroxy Leukotriene B4

LM ID

LMFA03020018

Formula

C₂₀H₃₂O₅

Exact Mass

Calculate m/z

352.224975

Sum Composition

FA 20:4;O3

Status

Curated

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Classification

Biological Context

20-hydroxy LTB4 is a metabolite of LTB4 in human neutrophils. In human leukocytes, LTB4 is inactivated by the enzyme LTB4 20-hydroxylase. 20-hydroxy LTB4 is not only much less active (~5%) compared to LTB4 in causing degranulation of PMNL,1 but actually inhibits LTB4-induced degranulation of human neutrophils (Ki = 13.3 nM).² However, 20-hydroxy LTB4 is as active as LTB4 in contracting parenchymal strips from guinea pig lung.³ 20-hydroxy LTB4 retains considerable ligand binding affinity at the BLT2 receptor,4,5 but does not appear to function as an agonist.⁶

This information has been provided by Cayman Chemical

References

1. Hansson, G., Lindgren, J.Å., Dahlén, S.E., et al. Identification and biological activity of novel w -oxidized metabolites of leukotriene B4 from human leukocytes. FEBS Lett. 130(1), 107-112 (1981).

2. Feinmark, S.J., Lindgren, J.Å., Claesson, H.E., et al. Stimulation of human leukocyte degranulation by leukotriene B4 and its ω-oxidized metabolites. FEBS Lett. 136, 141-144 (1981).

3. Falcone, R.C., and Aharony, D. Modulation of ligand binding to leukotriene B4 receptors on guinea pig lung membranes by sulfhydryl modifying reagents. J. Pharmacol. Exp. Ther. 255, 565-571 (1990).

4. Kamohara, M., Takasaki, J., Matsumoto, M., et al. Molecular cloning and characterization of another leukotriene B4 receptor. The Journal of Biological Chemisty 275(35), 27000-27004 (2000).

5. Wang, S., Gustafson, E., Pang, L., et al. A novel hepatointestinal leukotriene B4 receptor. The Journal of Biological Chemisty 275(52), 40686-40694 (2000).

6. 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).

String Representations

InChiKey (Click to copy)

PTJFJXLGRSTECQ-PSPARDEHSA-N

InChi (Click to copy)

InChI=1S/C20H32O5/c21-17-10-6-2-1-3-7-12-18(22)13-8-4-5-9-14-19(23)15-11-16-20(24)25/h3-5,7-9,13-14,18-19,21-23H,1-2,6,10-12,15-17H2,(H,24,25)/b5-4+,7-3-,13-8+,14-9-/t18-,19-/m1/s1

SMILES (Click to copy)

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