Structure Database (LMSD)
Common Name
5Z,8Z,11Z,14Z-Eicosatetraenedioic acid
Systematic Name
5Z,8Z,11Z,14Z-Eicosatetraenedioic acid
Synonyms
LM ID
LMFA01170034
Formula
Exact Mass
Calculate m/z
334.21441
Sum Composition
Status
Curated
3D model of 5Z,8Z,11Z,14Z-Eicosatetraenedioic acid
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
20-carboxy Arachidonic acid (20-COOH-AA) is the major metabolite of 20-HETE that is produced in renal tubular epithelial, endothelial, and microvascular smooth muscle cell cultures. This ω-oxidation conversion can take place using purified alcohol dehydrogenases three and four or by microsomes containing recombinant human CYP4F3B.1 Like 20-HETE, 20-COOH-AA inhibits ion transport in the kidneys. It also produces vasorelaxation of porcine coronary microvessels constricted with endothelin. 20-COOH-AA binds to isolated ligand binding domains of peroxisome proliferator-activated receptor α (PPARα) (Kd = 0.87 ± 0.12 µM) and PPARγ (Kd = 1.7 ± 0.5 µM), and is a dual activator of PPARα and PPARγ in a transiently transfected COS-7 cell reporter system.1
This information has been provided by Cayman Chemical
References
String Representations
InChiKey (Click to copy)
BGOJKUCHTMYINI-DTLRTWKJSA-N
InChi (Click to copy)
InChI=1S/C20H30O4/c21-19(22)17-15-13-11-9-7-5-3-1-2-4-6-8-10-12-14-16-18-20(23)24/h1,3-4,6-7,9-10,12H,2,5,8,11,13-18H2,(H,21,22)(H,23,24)/b3-1-,6-4-,9-7-,12-10-
SMILES (Click to copy)
C(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC(=O)O)(=O)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
24
Rings
0
Aromatic Rings
0
Rotatable Bonds
15
Van der Waals Molecular Volume
373.88
Topological Polar Surface Area
74.60
Hydrogen Bond Donors
2
Hydrogen Bond Acceptors
4
logP
5.28
Molar Refractivity
98.00
Admin
Created at
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Updated at
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