Name: Oleoyl 3-carbacyclic Phosphatidic Acid
Rating: 5 (10 reviews)

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HIT ID:HIT218638224
Cas No:
常用名:Oleoyl 3-carbacyclic Phosphatidic Acid
常用名:Oleoyl 3-carbacyclic Phosphatidic Acid
别名:3-ccPA 18:1
IUPAC:(2-hydroxy-2-oxo-1,2lambda5-oxaphospholan-5-yl)methyl octadec-9-enoate
IUPAC:(2-hydroxy-2-oxo-1,2lambda5-oxaphospholan-5-yl)methyl octadec-9-enoate
InChI key:IJSTZKWSILWQEC-UHFFFAOYSA-N

分子式:C22H41O5P
分子量:416.539
氢键供体数 (HBD):
氢键受体数 (HBA):
LogP:
SMILES:CCCCCCCCC=CCCCCCCCC(=O)OCC1CCP(O)(=O)O1
SMILES:CCCCCCCCC=CCCCCCCCC(=O)OCC1CCP(O)(=O)O1

Cyclic Phosphatidic Acids (cPAs) are naturally occurring lysophosphatidic acid (LPA) analogs, characterized by a 5-membered ring formed between the sn-2 hydroxy group and the sn-3 phosphate. Carba-derivatives of cPA (ccPA) modify the sn-2 (2-ccPA) or sn-3 (3-ccPA) linkage, hindering the conversion of cPA into LPA. Oleoyl 3-Carbacyclic Phosphatidic Acid (3-ccPA 18:1) incorporates the 18:1 fatty acid oleate at the sn-1 position on the glycerol backbone, acting as a cyclic LPA analog. This compound, at a concentration of 25 μM, blocks MM1 cells' transcellular migration through mesothelial cell monolayers induced by fetal bovine serum (by 90.1%) or LPA (by 99.9%), without impeding cell proliferation. Additionally, 3-ccPA 18:1, in the 0.1-1.0 μM range, notably suppresses autotaxin, which plays a vital role in various cancer cell behaviors including survival, growth, migration, invasion, and metastasis.

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