Lysophosphatidic acid

Names
Systematic IUPAC name (2R)-2-hydroxy-3-{[(9Z)-octadec-9-enoyl]oxy}propyl dihydrogen phosphate
Other names LPA 1-acyl-sn-glycerol 3-phosphate
Identifiers
CAS Number	22002-87-5 Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL117021 N
ChemSpider	4593722
ECHA InfoCard	100.040.631
EC Number	244-710-0
IUPHAR/BPS	2906
MeSH	lysophosphatidic+acid
PubChemCID	5497152
UNII	PG6M3969SG Y
CompTox Dashboard(EPA)	DTXSID001015741 DTXSID5041061, DTXSID001015741
InChI InChI=1S/C21H41O7P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(23)27-18-20(22)19-28-29(24,25)26/h9-10,20,22H,2-8,11-19H2,1H3,(H2,24,25,26)/b10-9- Key: WRGQSWVCFNIUNZ-KTKRTIGZSA-N
SMILES CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(=O)(O)O)O
Properties
Chemical formula	C21H41O7P
Molar mass	436.52 g/mol
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Alysophosphatidic acid (LPA) is aphospholipid derivative that can act as asignaling molecule.^[1][2][3][4]

LPA acts as a potentmitogen due to its activation of three high-affinityG-protein-coupled receptors calledLPAR1,LPAR2, andLPAR3 (also known as EDG2, EDG4, and EDG7). Additional, newly identified LPA receptors includeLPAR4 (P2RY9, GPR23),LPAR5 (GPR92) andLPAR6 (P2RY5, GPR87).

Because of its ability to stimulatecell proliferation, aberrant LPA-signaling has been linked to cancer in numerous ways. Dysregulation ofautotaxin or the LPA receptors can lead to hyperproliferation, which may contribute to oncogenesis andmetastasis.^[5]

LPA may cause pruritus (itching) in individuals with cholestatic (impaired bile flow) diseases.

Downstream of LPA receptor activation, the small GTPaseRho can be activated, subsequently activating Rho kinase. This can lead to the formation ofstress fibers and cell migration by inhibitingmyosin light-chain phosphatase.

There are several potential routes to its biosynthesis, but the most well-characterized is the action of a lysophospholipase D calledautotaxin, which removes thecholine group fromlysophosphatidylcholine.

Lysophosphatidic acids are also intermediates in the synthesis ofphosphatidic acids.

• Kremer, Andreas E.; Martens, Job J.W.W.; Kulik, Wim; Ruëff, Franziska; Kuiper, Edith M.M.; Van Buuren, Henk R.; Van Erpecum, Karel J.; Kondrackiene, Jurate; et al. (2010). "Lysophosphatidic Acid is a Potential Mediator of Cholestatic Pruritus".Gastroenterology.139 (3):1008–18, 1018.e1.doi:10.1053/j.gastro.2010.05.009.PMID 20546739.
• Moolenaar, Wouter H. (1995)."Lysophosphatidic Acid, a Multifunctional Phospholipid Messenger".The Journal of Biological Chemistry.270 (22):12949–52.doi:10.1074/jbc.270.22.12949.PMID 7768880.
• Mills, Gordon B.; Moolenaar, Wouter H. (2003). "The emerging role of lysophosphatidic acid in cancer".Nature Reviews Cancer.3 (8):582–91.doi:10.1038/nrc1143.PMID 12894246.S2CID 29079135.
• Panupinthu, N; Lee, H Y; Mills, G B (2010)."Lysophosphatidic acid production and action: Critical new players in breast cancer initiation and progression".British Journal of Cancer.102 (6):941–6.doi:10.1038/sj.bjc.6605588.PMC 2844037.PMID 20234370.
• Park, S Y; Jeong, K J; Panupinthu, N; Yu, S; Lee, J; Han, J W; Kim, J M; Lee, J-S; et al. (2010)."Lysophosphatidic acid augments human hepatocellular carcinoma cell invasion through LPA1 receptor and MMP-9 expression".Oncogene.30 (11):1351–9.doi:10.1038/onc.2010.517.PMID 21102517.
• Yakubu, M A; Liliom, K; Tigyi, G J; Leffler, C W (1997). "Role of lysophosphatidic acid in endothelin-1-and hematoma-induced alteration of cerebral microcirculation".American Journal of Physiology. Regulatory, Integrative and Comparative Physiology.273 (2):R703 –R709.doi:10.1152/ajpregu.1997.273.2.R703.
• Tigyi, G J; Hong, L; Yakubu, M; Parfenova, H; Shibata, M; Leffler, C W (1995). "Lysophosphatidic acid alters cerebrovascular reactivity in piglets".American Journal of Physiology. Heart and Circulatory Physiology.268 (5):H2048 –H2055.doi:10.1152/ajpheart.1995.268.5.H2048.PMID 7771554.

• Phospholipids

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