Oleoyl 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 lysophosphatidic acid (LPA). Oleoyl 3-Carbacyclic Phosphatidic Acid (3-ccPA 18:1) is a cyclic LPA analog that contains the 18:1 fatty acid, oleate, 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 (90.1%) or LPA (99.9%) without affecting proliferation. 3-ccPA 18:1, at 0.1-1.0 µM, significantly inhibits autotaxin, an enzyme that is important in cancer cell survival, growth, migration, invasion, and metastasis.Formal Name: (9Z)-9-octadecenoic acid, (2-hydroxy-2-oxido-1,2-oxaphospholan-5-yl)methyl ester. CAS Number: 779333-58-3. Synonyms: 3-ccPA 18:1. Molecular Formula: C22H41O5P. Formula Weight: 416.5. Purity: >95%. Formulation: (Request formulation change), A solution in chloroform. Solubility: PBS (pH 7.2): 5 mg/ml. SMILES: CCCCCCCC/C=C\CCCCCCCC(=O)OCC1CCP(=O)(O)O1. InChi Code: InChI=1S/C22H41O5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-22(23)26-20-21-18-19-28(24,25)27-21/h9-10,21H,2-8,11-20H2,1H3,(H,24,25)/b10-9-. InChi Key: IJSTZKWSILWQEC-KTKRTIGZSA-N. Side Chain Carbon Sum: 18:1.