oleic acid

Ligand id: 1054

Name: oleic acid

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 15
Topological polar surface area 37.3
Molecular weight 282.26
XLogP 8.19
No. Lipinski's rules broken 2

Molecular properties generated using the CDK

1. 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.
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2. Gimeno RE, Ortegon AM, Patel S, Punreddy S, Ge P, Sun Y, Lodish HF, Stahl A. (2003)
Characterization of a heart-specific fatty acid transport protein.
J. Biol. Chem., 278 (18): 16039-44. [PMID:12556534]
3. 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]
4. 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]
5. 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]
6. 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]
7. Sarri E, Pardo R, Fensome-Green A, Cockcroft S. (2003)
Endogenous phospholipase D2 localizes to the plasma membrane of RBL-2H3 mast cells and can be distinguished from ADP ribosylation factor-stimulated phospholipase D1 activity by its specific sensitivity to oleic acid.
Biochem. J., 369 (Pt 2): 319-29. [PMID:12374567]
8. Schaffer JE, Lodish HF. (1994)
Expression cloning and characterization of a novel adipocyte long chain fatty acid transport protein.
Cell, 79 (3): 427-36. [PMID:7954810]
9. Stahl A, Hirsch DJ, Gimeno RE, Punreddy S, Ge P, Watson N, Patel S, Kotler M, Raimondi A, Tartaglia LA et al.. (1999)
Identification of the major intestinal fatty acid transport protein.
Mol. Cell, 4 (3): 299-308. [PMID:10518211]
10. Watson SJ, Brown AJ, Holliday ND. (2012)
Differential signaling by splice variants of the human free fatty acid receptor GPR120.
Mol. Pharmacol., 81 (5): 631-42. [PMID:22282525]