An LPA mimetic and LPA receptor agonist
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Oleoyl Ethanolamide Phosphate

Item No. 22886

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[2-(phosphonooxy)ethyl]-9Z-octadecenamide
CAS Number
24435-25-4
Synonyms
  • NAEPA
  • N-oleoyl ethanolamide phosphoric acid
  • OEA-P
Molecular Formula
C20H40NO5P
Formula Weight
405.5
Purity
≥95%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMSO: soluble
SMILES
OP(OCCNC(CCCCCCC/C=C\CCCCCCCC)=O)(O)=O
InChi Code
InChI=1S/C20H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(22)21-18-19-26-27(23,24)25/h9-10H,2-8,11-19H2,1H3,(H,21,22)(H2,23,24,25)/b10-9-
InChi Key
BCSUWOZFWWBYSX-KTKRTIGZSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

    $75

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    5 mg

    $278

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    10 mg

    $516

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    Product Description

    Oleoyl ethanolamide phosphate (OEA-P) is a lysophosphatidic acid (LPA) mimetic, LPA receptor agonist, and phosphate ester of oleoyl ethanolamide (OEA; Item No. 90265).1,2 It selectively increases [35S]GTPγS binding to HEK293T cell membranes expressing LPA1 and LPA2 over LPA3 receptors.2 OEA-P induces calcium mobilization and inhibits forskolin-induced cAMP accumulation in MDA-MB-231 cells (EC50s = 1.2 and 101 nM, respectively).1

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Lynch, K.R., Hopper, D.W., Carlisle, S.J., et al. Structure/activity relationships in lysophosphatidic acid: The 2-hydroxyl moiety. Mol. Pharmacol. 52(1), 75-81 (1997).

    2. Im, D.S., Heise, C.E., Harding, M.A., et al. Molecular cloning and characterization of a lysophosphatidic acid receptor, Edg-7, expressed in prostate. Mol. Pharmacol. 57, 753-759 (2000).