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-
| Molecular Formula | C21H41O7P |
| Molecular Weight | 436.5198 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 1 |
| Optical Activity | ( + / - ) |
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 |
|---|---|---|
| Tumor-induced inflammation in mammary adipose tissue stimulates a vicious cycle of autotaxin expression and breast cancer progression. | 2015-09 |
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| Autotaxin is an inflammatory mediator and therapeutic target in thyroid cancer. | 2015-08 |
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| Regulation of autotaxin expression and secretion by lysophosphatidate and sphingosine 1-phosphate. | 2015-06 |
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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. | 2015-03 |
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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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| Inhibition of autotaxin delays breast tumor growth and lung metastasis in mice. | 2014-06 |
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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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| EGFR mediates LPA-induced proteolytic enzyme expression and ovarian cancer invasion: inhibition by resveratrol. | 2013-02 |
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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. | 2012-08 |
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| Protection of neuroblastoma Neuro2A cells from hypoxia-induced apoptosis by cyclic phosphatidic acid (cPA). | 2012 |
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| Lysophosphatidic acid receptor 1 modulates lipopolysaccharide-induced inflammation in alveolar epithelial cells and murine lungs. | 2011-10 |
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| Structure-based design of novel boronic acid-based inhibitors of autotaxin. | 2011-07-14 |
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| Biochemical and structural characterization of lysophosphatidic Acid binding by a humanized monoclonal antibody. | 2011-05-06 |
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| Benzyl and naphthalene methylphosphonic acid inhibitors of autotaxin with anti-invasive and anti-metastatic activity. | 2011-05-02 |
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| Minimal peroxide exposure of neuronal cells induces multifaceted adaptive responses. | 2010-12-17 |
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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. | 2010-12 |
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| Isoform-specific phosphoinositide 3-kinase inhibitors exert distinct effects in solid tumors. | 2010-02-01 |
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| Lithocholate--a promising non-calcaemic calcitriol surrogate for promoting human osteoblast maturation upon biomaterials. | 2009-11 |
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| Lysophosphatidic acid can support the formation of membranous structures and an increase in MBP mRNA levels in differentiating oligodendrocytes. | 2009-01 |
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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. | 2008-12 |
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| G protein-coupled receptor P2Y5 and its ligand LPA are involved in maintenance of human hair growth. | 2008-03 |
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| Hypoxia enhances LPA-induced HIF-1alpha and VEGF expression: their inhibition by resveratrol. | 2007-12-08 |
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| Resveratrol is a class IA phosphoinositide 3-kinase inhibitor. | 2007-09-15 |
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| Expression and function of lysophosphatidic acid LPA1 receptor in prostate cancer cells. | 2006-10 |
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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. | 2006-02-10 |
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| Neutrophil sphingosine 1-phosphate and lysophosphatidic acid receptors in pneumonia. | 2006-02 |
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| Increase of laminin 5 synthesis in human keratinocytes by acute wound fluid, inflammatory cytokines and growth factors, and lysophospholipids. | 2004-11 |
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| Differential effects of simvastatin on mesangial cells. | 2004-07 |
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| Lysophosphatidic acid induces hypertrophy of neonatal cardiac myocytes via activation of Gi and Rho. | 2004-04 |
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| Role of phospholipase D1 in the regulation of mTOR activity by lysophosphatidic acid. | 2004-02 |
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| Regulation of extracellular signal-regulated kinase by cannabinoids in hippocampus. | 2003-03-15 |
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| Fluoroaluminate stimulates phosphorylation of p130 Cas and Fak and increases attachment and spreading of preosteoblastic MC3T3-E1 cells. | 2002-01 |
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| Role of the small GTP-binding protein rho in epithelial cell migration in the rabbit cornea. | 2001-04 |
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| Enhancement of lysophosphatidic acid-induced ERK phosphorylation by phospholipase D1 via the formation of phosphatidic acid. | 2001-03 |
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| Type Ialpha phosphatidylinositol 4-phosphate 5-kinase is a putative target for increased intracellular phosphatidic acid. | 2000-07-07 |
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| Involvement of lipoxygenase in lysophosphatidic acid-stimulated hydrogen peroxide release in human HaCaT keratinocytes. | 2000-03-15 |
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| Regulation of LPA-promoted myofibroblast contraction: role of Rho, myosin light chain kinase, and myosin light chain phosphatase. | 2000-02-01 |
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| Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate. | 1999-11 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:06:13 GMT 2025
by
admin
on
Mon Mar 31 23:06:13 GMT 2025
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| Record UNII |
PG6M3969SG
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| Record Status |
Validated (UNII)
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| Record Version |
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PG6M3969SG
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LYSOPHOSPHATIDIC ACID
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PG6M3969SG
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