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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24045401
Curator's Comment: enhances of blood-brain barrier permeability
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: Q92633 Gene ID: 1902.0 Gene Symbol: LPAR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/9600933/ |
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Target ID: Q9HBW0 Gene ID: 9170.0 Gene Symbol: LPAR2 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11264467/ |
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Target ID: Q9UBY5 Gene ID: 23566.0 Gene Symbol: LPAR3 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11264467/ |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Preventing | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
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Diagnostic | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate. | 1999 Nov |
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Regulation of LPA-promoted myofibroblast contraction: role of Rho, myosin light chain kinase, and myosin light chain phosphatase. | 2000 Feb 1 |
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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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Involvement of lipoxygenase in lysophosphatidic acid-stimulated hydrogen peroxide release in human HaCaT keratinocytes. | 2000 Mar 15 |
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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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Fluoroaluminate stimulates phosphorylation of p130 Cas and Fak and increases attachment and spreading of preosteoblastic MC3T3-E1 cells. | 2002 Jan |
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Regulation of extracellular signal-regulated kinase by cannabinoids in hippocampus. | 2003 Mar 15 |
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Lysophosphatidic acid induces hypertrophy of neonatal cardiac myocytes via activation of Gi and Rho. | 2004 Apr |
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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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Increase of laminin 5 synthesis in human keratinocytes by acute wound fluid, inflammatory cytokines and growth factors, and lysophospholipids. | 2004 Nov |
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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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Hypoxia enhances LPA-induced HIF-1alpha and VEGF expression: their inhibition by resveratrol. | 2007 Dec 8 |
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Resveratrol is a class IA phosphoinositide 3-kinase inhibitor. | 2007 Sep 15 |
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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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G protein-coupled receptor P2Y5 and its ligand LPA are involved in maintenance of human hair growth. | 2008 Mar |
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Lysophosphatidic acid can support the formation of membranous structures and an increase in MBP mRNA levels in differentiating oligodendrocytes. | 2009 Jan |
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Lithocholate--a promising non-calcaemic calcitriol surrogate for promoting human osteoblast maturation upon biomaterials. | 2009 Nov |
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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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Isoform-specific phosphoinositide 3-kinase inhibitors exert distinct effects in solid tumors. | 2010 Feb 1 |
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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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Biochemical and structural characterization of lysophosphatidic Acid binding by a humanized monoclonal antibody. | 2011 May 6 |
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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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Protection of neuroblastoma Neuro2A cells from hypoxia-induced apoptosis by cyclic phosphatidic acid (cPA). | 2012 |
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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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A novel highly potent autotaxin/ENPP2 inhibitor produces prolonged decreases in plasma lysophosphatidic acid formation in vivo and regulates urethral tension. | 2014 |
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Inhibition of autotaxin delays breast tumor growth and lung metastasis in mice. | 2014 Jun |
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Lysophosphatidic acid alters the expression profiles of angiogenic factors, cytokines, and chemokines in mouse liver sinusoidal endothelial cells. | 2015 |
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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 |
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Tumor-induced inflammation in mammary adipose tissue stimulates a vicious cycle of autotaxin expression and breast cancer progression. | 2015 Sep |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28667502
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20056268
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