:Lysophosphatidylinositol

{{Chembox

| ImageFile = Lysophosphatidylinositol.svg

| ImageSize = 250px

| IUPACName = [(2R)-2-hydroxy-3-[hydroxy-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]-oxyphosphoryl]oxypropyl] hexadecanoate

| OtherNames =

|Section1={{Chembox Identifiers

| CASNo = 796963-91-2

| ChEBI =

| PubChem = 71296207

| ChemSpiderID = 59664394

| StdInChI=1S/C25H49O12P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)35-16-18(26)17-36-38(33,34)37-25-23(31)21(29)20(28)22(30)24(25)32/h18,20-26,28-32H,2-17H2,1H3,(H,33,34)/t18-,20?,21-,22+,23-,24-,25?/m1/s1

| StdInChIKey = UOXRPRZMAROFPH-IESLQMLBSA-N

| 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

}}

|Section2={{Chembox Properties

| C=25 | H=49 | O=12 | P=1

| MolarMass =

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|Section3={{Chembox Hazards

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Lysophosphatidylinositol (LPI, lysoPI), or L-α-lysophosphatidylinositol, is an endogenous lysophospholipid and endocannabinoid neurotransmitter.{{cite journal |vauthors=Li X, Wang L, Fang P, etal |title = Lysophospholipids induce innate immune transdifferentiation of endothelial cells, resulting in prolonged endothelial activation. | journal = The Journal of Biological Chemistry |date=May 2018 |volume = 293 |issue = 28 |pages = 11033–11045 | pmid = 29769317 |doi = 10.1074/jbc.RA118.002752|pmc = 6052225 |doi-access = free }} LPI, along with its 2-arachidonoyl- derivative, 2-arachidonoyl lysophosphatidylinositol (2-ALPI), have been proposed as the endogenous ligands of GPR55.{{cite journal |vauthors=Oka S, Nakajima K, Yamashita A, Kishimoto S, Sugiura T | title = Identification of GPR55 as a lysophosphatidylinositol receptor | journal = Biochemical and Biophysical Research Communications | volume = 362 | issue = 4 | pages = 928–34 |date=November 2007 | pmid = 17765871 | doi = 10.1016/j.bbrc.2007.08.078 }}{{cite journal |vauthors=Henstridge CM, Balenga NA, Ford LA, Ross RA, Waldhoer M, Irving AJ | title = The GPR55 ligand L-alpha-lysophosphatidylinositol promotes RhoA-dependent Ca2+ signaling and NFAT activation | journal = The FASEB Journal | volume = 23 | issue = 1 | pages = 183–93 |date=January 2009 | pmid = 18757503 | doi = 10.1096/fj.08-108670 | doi-access = free | s2cid = 27142069 }}{{cite journal|doi=10.1016/j.bbalip.2012.01.009 |title=Lysophosphatidylinositol signalling: New wine from an old bottle |year=2012 |last1=Piñeiro |first1=Roberto |last2=Falasca |first2=Marco |journal=Biochimica et Biophysica Acta (BBA) - Molecular and Cell Biology of Lipids |volume=1821 |issue=4 |pages=694–705 |pmid=22285325|url=https://zenodo.org/record/895487 }}{{cite journal |vauthors=Oka S, Toshida T, Maruyama K, Nakajima K, Yamashita A, Sugiura T | title = 2-Arachidonoyl-sn-glycero-3-phosphoinositol: a possible natural ligand for GPR55 | journal = Journal of Biochemistry | volume = 145 | issue = 1 | pages = 13–20 |date=January 2009 | pmid = 18845565 | doi = 10.1093/jb/mvn136 }} Recent studies have shown that the fatty acyl composition of LPI influences neuroinflammatory responses in primary neuronal cultures, highlighting its potential role in neuroinflammation.{{cite journal |vauthors= Brenneman DE, Petkanas D, Ippolito M, Ward SJ | title = Effect of Fatty Acyl Composition for Lysophosphatidylinositol on Neuroinflammatory Responses in Primary Neuronal Cultures | journal = Journal of Molecular Neuroscience | volume = 75 | issue = 1 | pages = 35 | date = 2025 | pmid = 39866868 | pmc = 11760249 | doi = 10.1007/s12031-025-02326-7 | url = https://doi.org/10.1007/s12031-025-02326-7 }}