Inhibitor of autotaxin
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Palmitoyl 3-carbacyclic Phosphatidic Acid

Item No. 10010293

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
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
A crystalline solid
Solubility(Learn about Variance in 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
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $84

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    1 mg

    $157

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    5 mg

    $653

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    10 mg

    $1,141

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    Product Description

    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.1 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.1 3-ccPA 16:0, at 0.1-25 μM, significantly inhibits autotaxin,2,3 an enzyme that is important in cancer cell survival, growth, migration, invasion and metastasis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Uchiyama, A., Mukai, M., Fujiwara, Y., et al. Inhibition of transcellular tumor cell migration and metastasis by novel carba-derivatives of cyclic phosphatidic acid. Biochim. Biophys. Acta 1771(1), 103-112 (2007).

    2. Baker, D.L., Fujiwara, Y., Pigg, K.R., et al. Carba analogs of cyclic phosphatidic acid are selective inhibitors of autotaxin and cancer cell invasion and metastasis. The Journal of Biological Chemisty 281(32), 22786-22793 (2006).

    3. Prestwich, G.D., Gajewiak, J., Zhang, H., et al. Phosphatase-resistant analogues of lysophosphatidic acid: Agonists promote healing, antagonists and autotaxin inhibitors treat cancer. Biochim. Biophys. Acta 1781, 588-594 (2008).