Palmitoyl 3-carbacyclic Phosphatidic Acid

Cyclic phosphatidic acids (cPAs) are naturally occurring analogs of lysophosphatidic acid (LPA) in which the sn-2 hydroxy group forms a 5-membered ring with the sn-3 phosphate. Carba-derivatives of cPA (ccPA) are modified at the sn-2 (2-ccPA) or sn-3 (3-ccPA) linkage, preventing the opening of cPA to produce LPA. Palmitoyl 3-ccPA is a cyclic LPA analog that contains the 16:0 fatty acid, palmitate, at the sn-1 position of the glycerol backbone. At 25 µM, it inhibits the transcellular migration of MM1 cells across mesothelial cell monolayers in response to fetal bovine serum (81.9%) or LPA (98.9%) without affecting proliferation. 3-ccPA 16:0, at 0.1-25 µM, significantly inhibits autotaxin, an enzyme that is important in cancer cell survival, growth, migration, invasion and metastasis.Formal Name: (2-hydroxy-2-oxido-1,2-oxaphospholan-5-yl)methyl ester-hexadecanoic acid. CAS Number: 476310-22-2. Synonyms: 3-ccPA 16:0. Molecular Formula: C20H39O5P. Formula Weight: 390.5. Purity: >95%. Formulation: (Request formulation change), A crystalline solid. Solubility: PBS (pH 7.2): 0.5 mg/ml. SMILES: CCCCCCCCCCCCCCCC(=O)OCC1CCP(=O)(O)O1. InChi Code: InChI=1S/C20H39O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-20(21)24-18-19-16-17-26(22,23)25-19/h19H,2-18H2,1H3,(H,22,23). InChi Key: LJNWYINJKCNEPA-UHFFFAOYSA-N. Side Chain Carbon Sum: 16:0.