A glycerophospholipid and LPA1 agonist
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1-Arachidoyl-2-hydroxy-sn-glycero-3-PA (sodium salt)

Item No. 39227

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
eicosanoic acid, (2R)-2-hydroxy-3-(phosphonooxy)propyl ester, monosodium salt
Synonyms
  • LPA 20:0
  • PA(20:0/0:0)
  • 1-Arachidoyl LPA
  • 1-Arachidoyl Lysophosphatidic Acid
  • 1-Eicosanoyl-2-hydroxy-sn-glycero-3-phosphate
  • 20:0 LPA
Molecular Formula
C23H46O7P • Na
Formula Weight
488.6
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Methanol: Soluble
SMILES
O=C(OC[C@@H](O)COP(O)([O-])=O)CCCCCCCCCCCCCCCCCCC.[Na+]
InChi Code
InChI=1S/C23H47O7P.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-23(25)29-20-22(24)21-30-31(26,27)28;/h22,24H,2-21H2,1H3,(H2,26,27,28);/q;+1/p-1/t22-;/m1./s1
InChi Key
AEAFHZIRTFLOQF-VZYDHVRKSA-M
Side Chain Carbon Sum
20:0
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    1 mg

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    Product Description

    1-Arachidoyl-2-hydroxy-sn-glycero-3-PA (1-arachidoyl LPA) is an agonist of lysophosphatidic acid receptor 1 (LPA1) and a glycerophospholipid containing arachidic acid (Item Nos. 9000339 | 21906) at the sn-1 position.1 It induces calcium mobilization in primary human lung fibroblasts (EC50 = 3.6 µM), which endogenously express LPA1 but not LPA2-LPA6. 1-Arachidoyl LPA (2.5 µM) also binds to the ligand-binding domain of peroxisome proliferator-activated receptor γ (PPARγ) in a cell-free assay.2 It has been found in human urine.3

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Sattikar, A., Dowling, M.R., and Rosethorne, E.M. Endogenous lysophosphatidic acid (LPA1) receptor agonists demonstrate ligand bias between calcium and ERK signalling pathways in human lung fibroblasts. Br. J. Pharmacol. 174(3), (2017).

    2. Tsukahara, T., Tsukahara, R., Yasuda, S., et al. Different residues mediate recognition of 1-O-oleyl-lysophosphatidic acid and rosiglitazone in the ligand binding domain of peroxisome proliferator-activated receptor γ. The Journal of Biological Chemisty 281(6), 3398-3407 (2006).

    3. Lim, S., Byeon, S.K., Lee, J.Y., et al. Computational approach to structural identification of phospholipids using raw mass spectra from nanoflow liquid chromatography-electrospray ionization-tandem mass spectrometry. J. Mass. Spectrom. 47(8), 1004-1014 (2012).