Lysophosphatidic acid

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Lysophosphatidic acid

IUPAC name	(2-hydroxy-3-phosphonooxypropyl) (Z)-octadec-9-enoate
Other names	LPA
Identifiers
CAS number	[22002-87-5]
PubChem	5497152
MeSH	lysophosphatidic+acid
SMILES	CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(=O)(O)O)O
Properties
Molecular formula	C₂₁H₄₁O₇P
Molar mass	436.52 g/mol
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) Infobox disclaimer and references

Lysophosphatidic acid (LPA) is a phospholipid derivative that acts as a potent signaling molecule. There are a number of potential routes to its biosynthesis, but the most well-characterized is by the action of a lysophospholipase D called autotaxin, which removes the choline group from lysophosphatidylcholine. LPA acts as a potent mitogen due to its activation of three high-affinity G-protein-coupled receptors called LPA1, LPA2, and LPA3 (also known as EDG2, EDG4, and EDG7). Additional, newly identified LPA receptors include LPA4 (p2y9/GPR23), LPA5 (GPR92) and LPA6 (GPR87).

Because of its ability to stimulate cell proliferation, aberrant LPA-signaling has been linked to cancer in numerous ways. Dysregulation of autotaxin or the LPA receptors can lead to hyperproliferation, which may contribute to oncogenesis and metastasis.

Downstream of LPA receptor activation, the small GTPase Rho can be activated, subsequently activating Rho kinase. This can lead to the formation of stress fibers and cell migration through the inhibition of myosin light-chain phosphatase.

Lysophosphatidic acid is also an intermediate in the synthesis of phosphatidic acid.

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Production of LPA by Autotaxin.

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[edit] References

Moolenar, W.H., Lysophosphatidic Acid, a Multifunctional Phospholipid Messenger. J. Biol. Chem. 1995. (270)22:12949. Article.
Mills, G.B., Moolenaar, W.H., The Emerging role of lysophosphatidic acid in cancer. Nat. Rev. Cancer. 2003. (8):582. Article