linoleic acid

Ligand id: 1052

Name: linoleic acid

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

References
1. Briscoe CP, Peat AJ, McKeown SC, Corbett DF, Goetz AS, Littleton TR, McCoy DC, Kenakin TP, Andrews JL, Ammala C, Fornwald JA, Ignar DM, Jenkinson S. (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: 619-628. [PMID:16702987]
2. Briscoe CP, Tadayyon M, Andrews JL, Benson WG, Chambers JK, Eilert MM, Ellis C, Elshourbagy NA, Goetz AS, Minnick DT, Murdock PR, Sauls HR, Shabon U, Spinage LD, Strum JC, Szekeres PG, Tan KB, Way JM, Ignar DM, Wilson S, Muir AI. (2003)
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.
J Biol Chem, 278: 11303-11311. [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, Tanaka H, Maruyama M, Satoh R, Okubo S, Kizawa H, Komatsu H, Matsumura F, Noguchi Y, Shinohara T, Hinuma S, Fujisawa Y, Fujino M. (2003)
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
Nature, 422: 173-176. [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: 406-410. [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]