Inhibitor of autotaxin
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Palmitoleoyl 3-carbacyclic Phosphatidic Acid

Item No. 10010298

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
9Z-hexadecenoic acid, (2-hydroxy-2-oxido-1,2-oxaphospholan-5-yl)methyl ester
CAS Number
910228-13-6
Synonyms
  • 3-carbacyclic PA
  • 3-ccPA 16:1
Molecular Formula
C20H37O5P
Formula Weight
388.5
Purity
≥95%
Formulation (Request formulation change)
A 10 mg/ml solution in chloroform
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 5 mg/ml
SMILES
CCCCCC/C=C\CCCCCCCC(=O)OCC1CCP(=O)(O)O1
InChi Code
InChI=1S/C20H37O5P/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/h7-8,19H,2-6,9-18H2,1H3,(H,22,23)/b8-7-
InChi Key
IAGUMCXYAAGWJD-FPLPWBNLSA-N
Side Chain Carbon Sum
16:1
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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Certificates of Analysis & Batch Specific Data

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    500 µg

    $54

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    1 mg

    $103

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    5 mg

    $432

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    10 mg

    $755

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    Product Description

    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.1,2 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).3 Palmitoleoyl 3-carbacyclic phosphatidic acid (3-ccPA 16:1) is a cyclic LPA analog that contains the 16:1 fatty acid, palmitoleate, at the sn-1 position of the glycerol backbone.3 At 25 μM, it inhibits the transcellular migration of MM1 cells across mesothelial cell monolayers in response to fetal bovine serum (86.9%) or LPA (99.9%) without affecting proliferation.3 3-ccPA 16:1 significantly inhibits autotaxin (IC50 = 620 nM), an enzyme that is important in cancer cell survival, growth, migration, invasion and metastasis.4 When delivered intraperitoneally, 3-ccPA 16:1 significantly reduces the number of lung metastases formed in mice injected with B16F10 melanoma cells in the tail vein.4

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

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