From Wikipedia, the free encyclopedia
Lysophosphatidylinositol
Names
IUPAC name
[(2R)-2-hydroxy-3-[hydroxy-[(2R,3R,5S,6R)-2,3,4,5,6-pentahydroxycyclohexyl]-oxyphosphoryl]oxypropyl] hexadecanoate
Identifiers
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
C 25 H 49 O 12 P
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).
Chemical compound
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]
See also
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 .
Receptor (
ligands )
CB1 Tooltip Cannabinoid receptor type 1
Agonists(abridged,
full list ) Inverse agonists Antagonists
CB2 Tooltip Cannabinoid receptor type 2
Agonists
2-AG
2-AGE (noladin ether)
3,3'-Diindolylmethane
4-O-Methylhonokiol
α-Amyrin · β-Amyrin
A-796,260
A-834,735
A-836,339
AM-1172
AM-1221
AM-1235
AM-1241
AM-2232
Anandamide
AZ-11713908
Cannabinol
Caryophyllene
CB-13
CBS-0550
CP 55,940
GW-405,833 (L-768,242)
GW-842,166X
HU-308
JTE 7-31
JWH-007
JWH-015
JWH-018
JWH-73
JWH-133
L-759,633
L-759,656
Lenabasum (anabasum)
Magnolol
MDA-19
Nabitan
NADA
Olorinab (APD-371)
PF-03550096
S-444,823
SER-601
Serinolamide A
UR-144
Tedalinab
THC (dronabinol)
THCV
Tetrahydromagnolol
Virodhamine
Antagonists
NAGly (
GPR18 )
GPR55
GPR119
Transporter (
modulators )
eCBTs Tooltip Endocannabinoid transporter
Enzyme (
modulators )
Others
Others:
2-PG (directly potentiates activity of 2-AG at CB1 receptor)
ARN-272 (FAAH-like anandamide transporter inhibitor)