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{{short description|Chemical compound}}
{{chembox {{chembox
| Verifiedfields = changed
| verifiedrevid = 417958372 | verifiedrevid = 455085796
| ImageFile = Lysophosphatidic_acid.svg | ImageFile = Lysophosphatidic_acid.svg
| ImageSize = 250px | ImageSize = 250px
| IUPACName = (2-hydroxy-3-phosphonooxypropyl) (Z)-octadec-9-enoate | SystematicName = (2''R'')-2-hydroxy-3-<nowiki/>{oxy}propyl dihydrogen phosphate
| OtherNames = LPA | OtherNames = LPA<br/>1-acyl-''sn''-glycerol 3-phosphate
| Section1 = {{Chembox Identifiers | Section1 = {{Chembox Identifiers
| IUPHAR_ligand = 2906
⚫ | CASNo = 22002-87-5
| CASNo_Ref = {{cascite|correct|??}}
⚫ | PubChem = 5497152
⚫ | CASNo = 22002-87-5
⚫ | SMILES = CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(=O)(O)O)O
| UNII_Ref = {{fdacite|correct|FDA}}
⚫ | MeSHName = lysophosphatidic+acid
| UNII = PG6M3969SG
| EINECS = 244-710-0
⚫ | PubChem = 5497152
| ChemSpiderID = 4593722
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 117021
⚫ | SMILES = CCCCCCCC\C=C/CCCCCCCC(=O)OCC(COP(=O)(O)O)O
| StdInChI = 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-
| StdInChIKey = WRGQSWVCFNIUNZ-KTKRTIGZSA-N
⚫ | MeSHName = lysophosphatidic+acid
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| Formula = C<sub>21</sub>H<sub>41</sub>O<sub>7</sub>P | Formula = C<sub>21</sub>H<sub>41</sub>O<sub>7</sub>P
| MolarMass = 436.52 g/mol | MolarMass = 436.52 g/mol
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = | MeltingPt =
| BoilingPt = | BoilingPt =
}} }}
| Section3 = {{Chembox Hazards | Section3 = {{Chembox Hazards
| Solubility = | MainHazards =
| MainHazards = | FlashPt =
| FlashPt = | AutoignitionPt =
| Autoignition =
}} }}
}} }}
A '''lysophosphatidic acid''' ('''LPA''') is a ] derivative that can act as a ] molecule.<ref>{{cite journal |last1=van Corven |first1=Emile J.|last2=Groenink |first2=Alida |last3=Jalink|first3=Kees|last4=Eichholtz|first4=Thomas|last5=Moolenaar|first5=Wouter H.|date=1989-10-06 |title=Lysophosphatidate-induced cell proliferation: Identification and dissection of signaling pathways mediated by G proteins |journal=Cell |volume=59 |issue=1 |pages=45–54 |doi=10.1016/0092-8674(89)90868-4 |pmid=2551506|s2cid=25154850}}</ref><ref>{{Cite journal |last1=Tsukahara |first1=Tamotsu |last2=Tsukahara |first2=Ryoko |last3=Haniu |first3=Hisao |last4=Matsuda |first4=Yoshikazu |last5=Murakami-Murofushi |first5=Kimiko |date=2015-09-05 |title=Cyclic phosphatidic acid inhibits the secretion of vascular endothelial growth factor from diabetic human coronary artery endothelial cells through peroxisome proliferator-activated receptor gamma |url=https://www.sciencedirect.com/science/article/pii/S0303720715002889 |journal=Molecular and Cellular Endocrinology |language=en |volume=412 |pages=320–329 |doi=10.1016/j.mce.2015.05.021 |pmid=26007326 |issn=0303-7207|hdl=10069/35888 |s2cid=10454566 |hdl-access=free }}</ref><ref>{{Cite journal |last=Moolenaar |first=Wouter H. |date=1995-06-02 |title=Lysophosphatidic Acid, a Multifunctional Phospholipid Messenger ∗ |url=https://www.jbc.org/article/S0021-9258(18)92226-X/abstract |journal=Journal of Biological Chemistry |language=English |volume=270 |issue=22 |pages=12949–12952 |doi=10.1074/jbc.270.22.12949 |issn=0021-9258 |pmid=7768880|doi-access=free }}</ref><ref>{{Cite journal |last1=Tigyi |first1=Gabor |last2=Parrill |first2=Abby L. |date=2003-11-01 |title=Molecular mechanisms of lysophosphatidic acid action |url=https://www.sciencedirect.com/science/article/pii/S0163782703000353 |journal=Progress in Lipid Research |language=en |volume=42 |issue=6 |pages=498–526 |doi=10.1016/S0163-7827(03)00035-3 |pmid=14559069 |issn=0163-7827}}</ref>
'''Lysophosphatidic acid''' (LPA) is a ] derivative that can act as a ] molecule.<ref name="GarrettGrisham2008">{{cite book|author1=Reginald Garrett|author2=Charles M. Grisham|title=Biochemistry|url=http://books.google.com/books?id=iGPsen3fSOIC&pg=PA235|accessdate=20 December 2010|date=28 December 2008|publisher=Cengage Learning|isbn=9780495109358|pages=235–}}</ref>


==Function== ==Function==
{{See also|Lysophospholipid receptor}}
LPA acts as a potent ] due to its activation of three high-affinity ] called ], ], and ] (also known as EDG2, EDG4, and EDG7). Additional, newly identified LPA receptors include LPA4 (p2y9/GPR23), LPA5 (GPR92) and LPA6 (GPR87). LPA acts as a potent ] due to its activation of three high-affinity ] called ], ], and ] (also known as EDG2, EDG4, and EDG7). Additional, newly identified LPA receptors include ] (P2RY9, GPR23), ] (GPR92) and ] (P2RY5, GPR87).


==Clinical significance== ==Clinical significance==
Because of its ability to stimulate ], aberrant LPA-signaling has been linked to cancer in numerous ways. Dysregulation of ] or the LPA receptors can lead to hyperproliferation, which may contribute to oncogenesis and ]. Because of its ability to stimulate ], aberrant LPA-signaling has been linked to cancer in numerous ways. Dysregulation of ] or the LPA receptors can lead to hyperproliferation, which may contribute to oncogenesis and ].<ref>{{cite journal|last1=Benesch|first1=MG|last2=Ko|first2=YM|last3=McMullen|first3=TP|last4=Brindley|first4=DN|title=Autotaxin in the crosshairs: taking aim at cancer and other inflammatory conditions|journal=FEBS Letters|date=2014|volume=588|issue=16|pages=2712–27|doi=10.1016/j.febslet.2014.02.009|pmid=24560789|s2cid=35544825|doi-access=free|bibcode=2014FEBSL.588.2712B }}</ref>


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


==GTPase activation== ==GTPase activation==
Downstream of LPA receptor activation, the small GTPase ] can be activated, subsequently activating Rho kinase. This can lead to the formation of stress fibers and cell migration through the inhibition of ]. Downstream of LPA receptor activation, the small GTPase ] can be activated, subsequently activating Rho kinase. This can lead to the formation of ]s and cell migration through the inhibition of ].


==Metabolism== ==Metabolism==
There are a number of potential routes to its biosynthesis, but the most well-characterized is by the action of a lyso] called ], which removes the ] group from ]. There are a number of potential routes to its biosynthesis, but the most well-characterized is by the action of a lyso] called ], which removes the ] group from ].


Lysophosphatidic acid is also an intermediate in the synthesis of ]. Lysophosphatidic acids are also intermediates in the synthesis of ]s.


] ]


==See also== ==See also==
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* ] * ]
* ] * ]
* ] * ]
* ]
* ]
{{colend}}


==References== ==References==
{{reflist}}
<references/>
* Kremer AE, Martens JJ, Kulik W, Ruëff F, Kuiper EM, van Buuren HR, van Erpecum KJ, Kondrackiene J, Prieto J, Rust C, Geenes VL, Williamson C, Moolenaar WH, Beuers U, Elferink RP. Lysophosphatidic acid is a potential mediator of cholestatic pruritus. Gastroenterology. 2010 May 20.
* Moolenaar, W.H., ''Lysophosphatidic Acid, a Multifunctional Phospholipid Messenger.'' J. Biol. Chem. 1995. (270)22:12949. .
* Mills, G.B., Moolenaar, W.H., ''The Emerging role of lysophosphatidic acid in cancer.'' Nat. Rev. Cancer. 2003. (8):582.


==Further reading==
{{Lipid_signaling}}
*{{cite journal |doi=10.1053/j.gastro.2010.05.009 |title=Lysophosphatidic Acid is a Potential Mediator of Cholestatic Pruritus |year=2010 |last1=Kremer |first1=Andreas E. |last2=Martens |first2=Job J.W.W. |last3=Kulik |first3=Wim |last4=Ruëff |first4=Franziska |last5=Kuiper |first5=Edith M.M. |last6=Van Buuren |first6=Henk R. |last7=Van Erpecum |first7=Karel J. |last8=Kondrackiene |first8=Jurate |last9=Prieto |first9=Jesus |last10=Rust |first10=Christian |last11=Geenes |first11=Victoria L. |last12=Williamson |first12=Catherine |last13=Moolenaar |first13=Wouter H. |last14=Beuers |first14=Ulrich |last15=Oude Elferink |first15=Ronald P.J. |journal=Gastroenterology |volume=139 |issue=3 |pages=1008–18, 1018.e1 |pmid=20546739|display-authors=8 }}
*{{cite journal |first1=Wouter H. |last1=Moolenaar |title=Lysophosphatidic Acid, a Multifunctional Phospholipid Messenger |journal=The Journal of Biological Chemistry |pmid=7768880 |doi=10.1074/jbc.270.22.12949 |url=http://www.jbc.org/cgi/pmidlookup?view=long&pmid=7768880 |year=1995 |volume=270 |issue=22 |pages=12949–52|doi-access=free }}
*{{cite journal |doi=10.1038/nrc1143 |title=The emerging role of lysophosphatidic acid in cancer |year=2003 |last1=Mills |first1=Gordon B. |last2=Moolenaar |first2=Wouter H. |journal=Nature Reviews Cancer |volume=3 |issue=8 |pages=582–91 |pmid=12894246|s2cid=29079135 }}
*{{cite journal |doi=10.1038/sj.bjc.6605588 |title=Lysophosphatidic acid production and action: Critical new players in breast cancer initiation and progression |year=2010 |last1=Panupinthu |first1=N |last2=Lee |first2=H Y |last3=Mills |first3=G B |journal=British Journal of Cancer |volume=102 |issue=6 |pages=941–6 |pmid=20234370 |pmc=2844037}}
*{{cite journal |doi=10.1038/onc.2010.517 |title=Lysophosphatidic acid augments human hepatocellular carcinoma cell invasion through LPA1 receptor and MMP-9 expression |year=2010 |last1=Park |first1=S Y |last2=Jeong |first2=K J |last3=Panupinthu |first3=N |last4=Yu |first4=S |last5=Lee |first5=J |last6=Han |first6=J W |last7=Kim |first7=J M |last8=Lee |first8=J-S |last9=Kang |first9=J |last10=Park |first10=C G |last11=Mills |first11=G B |last12=Lee |first12=H Y |journal=Oncogene |volume=30 |issue=11 |pages=1351–9 |pmid=21102517|display-authors=8 |doi-access=free }}
*{{cite journal |doi=10.1152/ajpregu.1997.273.2.R703 |last1=Yakubu |first1=M A |last2=Liliom | first2=K |last3=Tigyi |first3=G J |last4=Leffler |first4=C W |title=Role of lysophosphatidic acid in endothelin-1-and hematoma-induced alteration of cerebral microcirculation |journal=American Journal of Physiology. Regulatory, Integrative and Comparative Physiology |year=1997 |volume=273 |issue=2 |pages=R703–R709 }}
*{{cite journal |doi=10.1152/ajpheart.1995.268.5.H2048 |last1=Tigyi |first1=G J |last2=Hong |first2=L |last3=Yakubu |first3=M |last4=Parfenova |first4=H |last5=Shibata |first5=M |last6=Leffler |first6=C W |title=Lysophosphatidic acid alters cerebrovascular reactivity in piglets |journal=American Journal of Physiology. Heart and Circulatory Physiology |year=1995 |volume=268 |issue=5 |pages=H2048–H2055 |pmid=7771554 }}

{{Lipid signaling}}
{{Phospholipids}} {{Phospholipids}}
{{Lysophospholipid signaling}}
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