Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C21H41O7P |
| Molecular Weight | 436.5198 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCC\C=C/CCCCCCCC(=O)OCC(O)COP(O)(O)=O
InChI
InChIKey=WRGQSWVCFNIUNZ-KTKRTIGZSA-N
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-
Lysophosphatidic acid (LPA) is a multifunctional intercellular phospholipid messenger. LPA stimulates the growth of a variety of cells including fibroblasts, vascular smooth muscle cells, endothelial cells, and keratinocytes. It is produced in relatively high levels from activated platelets and can be detected in bodily fluids including serum, saliva, follicular fluid, and malignant effusions. LPA acts as a proliferative and anti-apoptotic factor and is a ligand for LPA1 (EDG-2), LPA2 (EDG-4) and LPA3 (EDG-7) receptors. The plasma LPA level can be a useful marker for ovarian cancer, particularly in the early stages of the disease. It is known, that the therapeutic administration of LPA also blocked APAP-induced liver damage, leading to an increased survival rate by increasing the glutathione level but decreasing inflammatory cytokines in an LPA1,3,5-independent manner. Thus, LPA might be an important therapeutic agent for drug-induced liver injury. In addition, was shown, that LPA levels in plasma and ascites may be useful diagnostic biomarkers for peritoneal carcinomatosis of gastric cancer.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: Q92633 Gene ID: 1902.0 Gene Symbol: LPAR1 Target Organism: Homo sapiens (Human) |
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Target ID: Q9HBW0 Gene ID: 9170.0 Gene Symbol: LPAR2 Target Organism: Homo sapiens (Human) |
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Target ID: Q9UBY5 Gene ID: 23566.0 Gene Symbol: LPAR3 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
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| Diagnostic | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate. | 1999 Nov |
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| Type Ialpha phosphatidylinositol 4-phosphate 5-kinase is a putative target for increased intracellular phosphatidic acid. | 2000 Jul 7 |
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| Role of the small GTP-binding protein rho in epithelial cell migration in the rabbit cornea. | 2001 Apr |
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| Enhancement of lysophosphatidic acid-induced ERK phosphorylation by phospholipase D1 via the formation of phosphatidic acid. | 2001 Mar |
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| Regulation of extracellular signal-regulated kinase by cannabinoids in hippocampus. | 2003 Mar 15 |
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| Role of phospholipase D1 in the regulation of mTOR activity by lysophosphatidic acid. | 2004 Feb |
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| Differential effects of simvastatin on mesangial cells. | 2004 Jul |
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| Neutrophil sphingosine 1-phosphate and lysophosphatidic acid receptors in pneumonia. | 2006 Feb |
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| Different residues mediate recognition of 1-O-oleyllysophosphatidic acid and rosiglitazone in the ligand binding domain of peroxisome proliferator-activated receptor gamma. | 2006 Feb 10 |
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| Expression and function of lysophosphatidic acid LPA1 receptor in prostate cancer cells. | 2006 Oct |
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| Simultaneous stimulation of spinal NK1 and NMDA receptors produces LPC which undergoes ATX-mediated conversion to LPA, an initiator of neuropathic pain. | 2008 Dec |
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| A novel cell permeant peptide inhibitor of MAPKAP kinase II inhibits intimal hyperplasia in a human saphenous vein organ culture model. | 2010 Dec |
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| Minimal peroxide exposure of neuronal cells induces multifaceted adaptive responses. | 2010 Dec 17 |
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| Structure-based design of novel boronic acid-based inhibitors of autotaxin. | 2011 Jul 14 |
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| Benzyl and naphthalene methylphosphonic acid inhibitors of autotaxin with anti-invasive and anti-metastatic activity. | 2011 May 2 |
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| Lysophosphatidic acid receptor 1 modulates lipopolysaccharide-induced inflammation in alveolar epithelial cells and murine lungs. | 2011 Oct |
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| Apolipoprotein A-I mimetic peptides inhibit expression and activity of hypoxia-inducible factor-1α in human ovarian cancer cell lines and a mouse ovarian cancer model. | 2012 Aug |
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| EGFR mediates LPA-induced proteolytic enzyme expression and ovarian cancer invasion: inhibition by resveratrol. | 2013 Feb |
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| Inhibition of autotaxin delays breast tumor growth and lung metastasis in mice. | 2014 Jun |
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| Regulation of autotaxin expression and secretion by lysophosphatidate and sphingosine 1-phosphate. | 2015 Jun |
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| Lysophosphatidate signaling stabilizes Nrf2 and increases the expression of genes involved in drug resistance and oxidative stress responses: implications for cancer treatment. | 2015 Mar |
Patents
Sample Use Guides
in mice: lysophosphatidic acid (LPA) protects against endotoxin-Induced acute kidney injury (AKI). C57BL/6 mice were treated with LPA 18:1 (5 mg/kg, i.p.) 1 h before being injected with the endotoxin lipopolysaccharide (LPS), and AKI was evaluated after 24 h.
Route of Administration:
Intraperitoneal
Lysophosphatidic acid (LPA) is a potent modulator of cellular proliferation and invasion for endometrial carcinoma (EC) cells. All experiments were performed in vitro using an EC cell line, HEC-1A. Cell proliferation was determined using the Promega MTS proliferation assay following 48 h of exposures to different concentrations of LPA (0.1, 1.0 and 10.0 microM). LPA also has the capacity to stimulate the secretion/activity of uPA and MMP-7.
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5497152
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62837
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1793921
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22002-87-5
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DTXSID001015741
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LYSOPHOSPHATIDIC ACID
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PG6M3969SG
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16975
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244-710-0
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SUBSTANCE RECORD
