| 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 |
MOL RATIO
1 MOL RATIO (average) |
| 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.
CNS Activity
Approval Year
PubMed
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.