Structure Database (LMSD)

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
Exact Mass
Calculate m/z
334.21441
Sum Composition
Status
Curated


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).
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

Other Databases

KEGG ID
HMDB ID
CHEBI ID
LIPIDBANK ID
XPR3111
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 24
Rings 0
Aromatic Rings 0
Rotatable Bonds 14
Van der Waals Molecular Volume 373.88
Topological Polar Surface Area 74.60
Hydrogen Bond Donors 2
Hydrogen Bond Acceptors 4
logP 4.65
Molar Refractivity 98.33

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Created at
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Updated at
21st Apr 2022