α-linolenic acid

Ligand id: 1049

Name: α-linolenic acid

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 13
Topological polar surface area 37.3
Molecular weight 278.22
XLogP 7.54
No. Lipinski's rules broken 2

Molecular properties generated using the CDK

References
1. Briscoe CP, Tadayyon M, Andrews JL, Benson WG, Chambers JK, Eilert MM, Ellis C, Elshourbagy NA, Goetz AS, Minnick DT et al.. (2003)
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.
J. Biol. Chem., 278 (13): 11303-11. [PMID:12496284]
2. Itoh Y, Kawamata Y, Harada M, Kobayashi M, Fujii R, Fukusumi S, Ogi K, Hosoya M, Tanaka Y, Uejima H et al.. (2003)
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
Nature, 422 (6928): 173-6. [PMID:12629551]
3. Kotarsky K, Nilsson NE, Flodgren E, Owman C, Olde B. (2003)
A human cell surface receptor activated by free fatty acids and thiazolidinedione drugs.
Biochem. Biophys. Res. Commun., 301 (2): 406-10. [PMID:12565875]
4. Richieri GV, Ogata RT, Kleinfeld AM. (1994)
Equilibrium constants for the binding of fatty acids with fatty acid-binding proteins from adipocyte, intestine, heart, and liver measured with the fluorescent probe ADIFAB.
J. Biol. Chem., 269 (39): 23918-30. [PMID:7929039]
5. Richieri GV, Ogata RT, Zimmerman AW, Veerkamp JH, Kleinfeld AM. (2000)
Fatty acid binding proteins from different tissues show distinct patterns of fatty acid interactions.
Biochemistry, 39 (24): 7197-204. [PMID:10852718]
6. Shimpukade B, Hudson BD, Hovgaard CK, Milligan G, Ulven T. (2012)
Discovery of a potent and selective GPR120 agonist.
J. Med. Chem., 55 (9): 4511-5. [PMID:22519963]
7. Tanaka T, Yano T, Adachi T, Koshimizu TA, Hirasawa A, Tsujimoto G. (2008)
Cloning and characterization of the rat free fatty acid receptor GPR120: in vivo effect of the natural ligand on GLP-1 secretion and proliferation of pancreatic beta cells.
Naunyn Schmiedebergs Arch. Pharmacol., 377 (4-6): 515-22. [PMID:18320172]