Structure Database (LMSD)

Common Name
Lipoxin B4
Systematic Name
5S,14R,15S-trihydroxy-6E,8Z,10E,12E-eicosatetraenoic acid
Synonyms
  • LXB4
LM ID
LMFA03040002
Formula
Exact Mass
Calculate m/z
352.224976
Sum Composition
Status
Curated

Classification

Biological Context

Lipoxin B4 (LXB4) is a positional isomer of LXA4 produced by the metabolism of 15-HETE or 15(S)-HpETE by human leukocytes.1,2 At a concentration of 100 nM, LXB4 inhibits polymorphonuclear leukocyte (PMN) migration stimulated by leukotriene B4 (LTB4) and inhibits LTB4-induced adhesion of PMNs with an IC50 value of 0.3 nM.3

This information has been provided by Cayman Chemical

References

1. Serhan, C.N., Hamberg, M., and Samuelsson, B. Lipoxins: Novel series of biologically active compounds formed from arachidonic acid in human leukocytes. Proc. Natl. Acad. Sci. USA 81(17), 5335-5339 (1984).
3. Papayianni, A., Serhan, C.N., and Brady, H.R. Lipoxin A4 and B4 inhibit leukotriene-stimulated interactions of human neutrophils and endothelial cells. J. Immunol. 156(6), 2264-2272 (1996).

References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Homo sapiens (#9606)
Mammalia (#40674)
On the stereochemistry and biosynthesis of lipoxin B.,
Proc Natl Acad Sci U S A, 1986
Pubmed ID: 3083410

String Representations

InChiKey (Click to copy)
UXVRTOKOJOMENI-WLPVFMORSA-N
InChi (Click to copy)
InChI=1S/C20H32O5/c1-2-3-8-14-18(22)19(23)15-10-7-5-4-6-9-12-17(21)13-11-16-20(24)25/h4-7,9-10,12,15,17-19,21-23H,2-3,8,11,13-14,16H2,1H3,(H,24,25)/b6-4-,7-5+,12-9+,15-10+/t17-,18+,19-/m1/s1
SMILES (Click to copy)
C(/C=C/[C@@H](O)CCCC(O)=O)=C/C=C/C=C/[C@@H](O)[C@@H](O)CCCCC

Other Databases

Wikipedia
KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
XPR4101
PubChem CID
SwissLipids ID
Cayman ID
GuidePharm ID

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 385.31
Topological Polar Surface Area 97.99
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 5
logP 3.99
Molar Refractivity 101.75

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Created at
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Updated at
10th Feb 2025