Lysophosphatidylinositol

Lysophosphatidylinositol
Names
	IUPAC name [(2R)-2-hydroxy-3-[hydroxy-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]-oxyphosphoryl]oxypropyl] hexadecanoate
Identifiers
CAS Number	796963-91-2;
3D model (JSmol)	Interactive image;
PubChem CID	71296207;
	SMILES CCCCCCCCCCCCCCCC(=O)OC[C@H](COP(=O)(O)OC1[C@@H]([C@H](C([C@H]([C@H]1O)O)O)O)O)O;
Properties
Chemical formula	C25H49O12P
Molar mass	572.629 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Lysophosphatidylinositol (LPI, lysoPI), or L-α-lysophosphatidylinositol, is an endogenous lysophospholipid and endocannabinoid neurotransmitter.^[1] LPI, along with its 2-arachidonoyl- derivative, 2-arachidonoyl lysophosphatidylinositol (2-ALPI), have been proposed as the endogenous ligands of GPR55.^[2]^[3]^[4]^[5]

References

^ Li X, Wang L, Fang P, et al. (May 2018). "Lysophospholipids induce innate immune transdifferentiation of endothelial cells, resulting in prolonged endothelial activation". The Journal of Biological Chemistry. 293 (28): 11033–11045. doi:10.1074/jbc.RA118.002752. PMC 6052225. PMID 29769317.
^ Oka S, Nakajima K, Yamashita A, Kishimoto S, Sugiura T (November 2007). "Identification of GPR55 as a lysophosphatidylinositol receptor". Biochemical and Biophysical Research Communications. 362 (4): 928–34. doi:10.1016/j.bbrc.2007.08.078. PMID 17765871.
^ Henstridge CM, Balenga NA, Ford LA, Ross RA, Waldhoer M, Irving AJ (January 2009). "The GPR55 ligand L-alpha-lysophosphatidylinositol promotes RhoA-dependent Ca2+ signaling and NFAT activation". The FASEB Journal. 23 (1): 183–93. doi:10.1096/fj.08-108670. PMID 18757503. S2CID 27142069.
^ Piñeiro, Roberto; Falasca, Marco (2012). "Lysophosphatidylinositol signalling: New wine from an old bottle". Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids. 1821 (4): 694–705. doi:10.1016/j.bbalip.2012.01.009. PMID 22285325.
^ Oka S, Toshida T, Maruyama K, Nakajima K, Yamashita A, Sugiura T (January 2009). "2-Arachidonoyl-sn-glycero-3-phosphoinositol: a possible natural ligand for GPR55". Journal of Biochemistry. 145 (1): 13–20. doi:10.1093/jb/mvn136. PMID 18845565.