linoleic acid   Click here for help

GtoPdb Ligand ID: 1052

Synonyms: C18:2 | linoleate | linolic acid | telfairic acid
PDB Ligand
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 14
Topological polar surface area 37.3
Molecular weight 280.24
XLogP 7.87
No. Lipinski's rules broken 2
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InChI InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-7,9-10H,2-5,8,11-17H2,1H3,(H,19,20)/b7-6-,10-9-
1. Briscoe CP, Peat AJ, McKeown SC, Corbett DF, Goetz AS, Littleton TR, McCoy DC, Kenakin TP, Andrews JL, Ammala C et al.. (2006)
Pharmacological regulation of insulin secretion in MIN6 cells through the fatty acid receptor GPR40: identification of agonist and antagonist small molecules.
Br J Pharmacol, 148 (5): 619-28. [PMID:16702987]
2. 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]
3. Ferry G, Bruneau V, Beauverger P, Goussard M, Rodriguez M, Lamamy V, Dromaint S, Canet E, Galizzi JP, Boutin JA. (2001)
Binding of prostaglandins to human PPARgamma: tool assessment and new natural ligands.
Eur J Pharmacol, 417 (1-2): 77-89. [PMID:11301062]
4. 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]
5. 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]
6. Lesage F, Terrenoire C, Romey G, Lazdunski M. (2000)
Human TREK2, a 2P domain mechano-sensitive K+ channel with multiple regulations by polyunsaturated fatty acids, lysophospholipids, and Gs, Gi, and Gq protein-coupled receptors.
J Biol Chem, 275 (37): 28398-405. [PMID:10880510]
7. McKay MC, Worley JF. (2001)
Linoleic acid both enhances activation and blocks Kv1.5 and Kv2.1 channels by two separate mechanisms.
Am J Physiol, Cell Physiol, 281 (4): C1277-84. [PMID:11546665]
8. 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]
9. 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]
10. Yu C, Chen L, Luo H, Chen J, Cheng F, Gui C, Zhang R, Shen J, Chen K, Jiang H, Shen X. (2004)
Binding analyses between Human PPARgamma-LBD and ligands.
Eur J Biochem, 271 (2): 386-97. [PMID:14717706]
11. Yuan X, Ta TC, Lin M, Evans JR, Dong Y, Bolotin E, Sherman MA, Forman BM, Sladek FM. (2009)
Identification of an endogenous ligand bound to a native orphan nuclear receptor.
PLoS ONE, 4 (5): e5609. [PMID:19440305]