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Structure Database (LMSD)

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Common Name

LTB5

Systematic Name

5S,12S-dihydroxy-6Z,8E,14Z,17Z-eicosapentanenoic acid

Synonyms

Leukotriene B5

LM ID

LMFA03020010

Formula

C₂₀H₃₀O₄

Exact Mass

Calculate m/z

334.21441

Sum Composition

FA 20:5;O2

Status

Curated

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Classification

Biological Context

Leukotriene B5 (LTB5) is a leukotriene with diverse biological activities.^1,2,3,4,5 It is a metabolite of eicosapentaenoic acid (EPA) formed through the 5-lipoxygenase (5-LO) pathway.⁶ LTB5 increases contraction of bullfrog lung strips ex vivo in a concentration-dependent manner.¹ In vivo, LTB5 (100 nM) reduces tumor volume in mice injected with Tm1 murine melanoma cells.² LTB5 also elicits chemokinesis and lysosomal enzyme release from polymorphonuclear leukocytes (PMNLs) 20- to 30-fold less, and induces platelet aggregation 8-fold less, potently than LTB4 .^3,4,5

This information has been provided by Cayman Chemical

References

1. Terano, T., Salmon, J.A., and Moncada, S. Biosynthesis and biological activity of leukotriene B5. Prostaglandins 27(2), 217-232 (1984).

2. Lee, T.H., Mencia-Huerta, J.M., Shih, C., et al. Characterization and biologic properties of 5,12-dihydroxy derivatives of eicosapentaenoic acid, including leukotriene B5 and the double lipoxygenase product. The Journal of Biological Chemisty 259(4), 2383-2389 (1984).

3. Ford-Hutchinson, A.W., Bray, M.A., Doig, M.V., et al. Leukotriene B, a potent chemokinetic and aggregating substance released from polymorphonuclear leukocytes. Nature 286(5770), 264-265 (1980).

4. Leitch, A.G., Lee, T.H., Ringel, E.W., et al. Immunologically induced generation of tetraene and pentaene leukotrienes in the peritoneal cavities of Menhaden-fed rats. J. Immunol. 132(5), 2559-2565 (1984).

5. Andazola, J.J., Underwood, J.A., Chiono, M., et al. Leukotriene B4 and leukotriene B5 have binding sites on lung membranes and cause contraction of bullfrog lung. J. Pharmacol. Exp. Ther. 263(3), 1111-1117 (1992).

6. Bachi, A.L., Kim, F.J., Nonogaki, S., et al. Leukotriene B4 creates a favorable microenvironment for murine melanoma growth. Mol. Cancer Res. 7(9), 1417-1424 (2009).

String Representations

InChiKey (Click to copy)

BISQPGCQOHLHQK-HDNPQISLSA-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/h3-4,6-11,14-15,18-19,21-22H,2,5,12-13,16-17H2,1H3,(H,23,24)/b4-3-,8-7+,9-6-,14-10+,15-11-/t18-,19-/m1/s1

SMILES (Click to copy)

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