Structure Database (LMSD)

Common Name
6-trans-LTB4
Systematic Name
5S,12R-dihydroxy-6E,8E,10E,14Z-eicosatetraenoic acid
Synonyms
  • 6-trans-Leukotriene B4
LM ID
LMFA03020013
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

Category
Main Class
Sub Class
Fatty Acyls [FA]
Eicosanoids [FA03]
Leukotrienes [FA0302]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Hydroxy fatty acids [FA0105]

Biological Context

6-trans LTB4 is produced by the non-enzymatic hydrolysis of LTA4.1 Oxidative decomposition of cysteinyl-leukotrienes such as LTC4 in the presence of myeloperoxidase and hypochlorous acid can also produce 6-trans LTB4, but the physiologic importance of this mechanism is not clear.2 6-trans LTB4 is relatively inactive compared to LTB4, but chemoattractant properties in neutrophils have been reported.3

This information has been provided by Cayman Chemical

References

1. Fretland, D.J., Widomski, D.L., Anglin, C.P., et al. 6-trans-Leukotriene B4 is a neutrophil chemotoxin in the guinea pig dermis. J. Leukoc. Biol. 49, 283-288 (1991).
2. Borgeat, P., and Samuelsson, B. Metabolism of arachidonic acid in polymorphonuclear leukocytes. The Journal of Biological Chemisty 254(16), 7865-7869 (1979).
3. Lee, C.W., Lewis, R.A., Tauber, A.I., et al. The myeloperoxidase-dependent metabolism of leukotrienes C4, D4, and E4 to 6-trans-leukotriene B4 diastereoisomers and the subclass-specific S-diastereoisomeric sulfoxides. The Journal of Biological Chemisty 258, 15004-15010 (1983).

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

String Representations

InChiKey (Click to copy)
VNYSSYRCGWBHLG-UKNWISKWSA-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-/m1/s1
SMILES (Click to copy)
C([C@@H](O)/C=C/C=C/C=C/[C@@H](O)CCCC(=O)O)/C=C\CCCCC

Other Databases

HMDB ID
HMDB0001085
CHEBI ID
63981
LIPIDBANK ID
XPR3115
PubChem CID
5283128
Cayman ID
35250

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 376.52
Topological Polar Surface Area 77.76
Hydrogen Bond Donors 3
Hydrogen Bond Acceptors 4
logP 4.73
Molar Refractivity 99.84

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Updated at
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