Structure Database (LMSD)
Common Name
LTB4 ethanol amide
Systematic Name
N-(2-hydroxyethyl)-5S,12R-dihydroxy-6Z,8E,10E,14Z-eicosatetraen-1-amide
Synonyms
- Leukotriene B4 ethanol amide
LM ID
LMFA03020012
Formula
Exact Mass
Calculate m/z
379.272259
Sum Composition
Status
Curated
3D model of LTB4 ethanol amide
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Biological Context
The effects of Leukotriene B4 (LTB4) are mediated by two known receptors, BLT1 and BLT2.1,2 LTB4 is a high affinity ligand for BLT1, and many of its pro-inflammatory effects are believed to be transduced through this receptor. The BLT2 is more enigmatic, in that LTB4 is not a high-affinity ligand, nor is it clear that BLT2 activation promotes inflammation. LTB4 ethanolamide (LTB4-EA) is a theoretical 5-LO metabolite of arachidonoyl ethanolamide (AEA). In CHO cells transfected with human BLTR1, LTB4-EA was a potent antagonist with about three times greater affinity for the receptor than LTB4 (Ki = 1.22 nM versus 3.88 nM). LTB4-EA antagonizes the LTB4-induced contractions of guinea pig lung parenchyma with an EC50 of 10 nM.3 LTB4-EA thus represents a potential endogenous anti-inflammatory compound functioning as a natural antagonist of BLTR1.
This information has been provided by Cayman Chemical
References
3. McHugh, D., McMaster, S., and Ross, R. Pharmacological characterization of LTB4 ethanolamide: Interaction with leukotriene (BLT) and vanilloid (TRPV1) receptors. 121-121.
String Representations
InChiKey (Click to copy)
DQLVVNIINUTUIU-XLFGVTECSA-N
InChi (Click to copy)
InChI=1S/C22H37NO4/c1-2-3-4-5-6-9-13-20(25)14-10-7-8-11-15-21(26)16-12-17-22(27)23-18-19-24/h6-11,14-15,20-21,24-26H,2-5,12-13,16-19H2,1H3,(H,23,27)/b8-7+,9-6-,14-10+,15-11-/t20-,21-/m1/s1
SMILES (Click to copy)
C([C@@H](O)/C=C/C=C/C=C\[C@@H](O)CCCC(NCCO)=O)/C=C\CCCCC
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
0
Aromatic Rings
0
Rotatable Bonds
16
Van der Waals Molecular Volume
422.12
Topological Polar Surface Area
89.79
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
5
logP
4.32
Molar Refractivity
113.28
Admin
Created at
-
Updated at
30th Sep 2021