An inhibitor of glucosylceramide synthase
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DL-threo-PPMP (hydrochloride)

Item No. 17236

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
rel-N-[(1R,2R)-2-hydroxy-1-(4-morpholinylmethyl)-2-phenylethyl]-hexadecanamide, monohydrochloride
CAS Number
139974-41-7
Synonyms
  • DL-threo-1-Phenyl-2-palmitoylamino-3-morpholino-1-propanol
Molecular Formula
C29H50N2O3 • HCl
Formula Weight
511.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 5 mg/mlDMSO: 20 mg/mlEthanol: 10 mg/ml
SMILES
O=C(CCCCCCCCCCCCCCC)N[C@H](CN1CCOCC1)[C@H](O)C2=CC=CC=C2.Cl
InChi Code
InChI=1S/C29H50N2O3.ClH/c1-2-3-4-5-6-7-8-9-10-11-12-13-17-20-28(32)30-27(25-31-21-23-34-24-22-31)29(33)26-18-15-14-16-19-26;/h14-16,18-19,27,29,33H,2-13,17,20-25H2,1H3,(H,30,32);1H/t27-,29-;/m1./s1
InChi Key
ORVAUBQYJOFWFY-ZHESDOBJSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Wet ice in continental US; may vary elsewhere
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    5 mg

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    50 mg

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    100 mg

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    Product Description

    DL-threo-PPMP is a ceramide analog and an inhibitor of glucosylceramide synthase.1 It inhibits glucosylceramide synthase by 70, 41, and 62% in MDCK cell homogenates, mouse liver microsomes, and mouse brain homogenates, respectively, when used at a concentration of 20 µM. DL-threo-PPMP also inhibits sphingomyelin synthase activity in erythrocytes infected with P. falciparum and inhibits late ring-stage P. falciparum growth (IC50 = 0.85 µM).2 It reduces Akt and ribosomal protein S6 phosphorylation in HEK293 cells and increases autophagy flux in primary mouse neurons.3 [Matreya, LLC. Catalog No. 1720]

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Abe, A., Inokuchi, J.-i., Jimbo, M., et al. Improved inhibitors of glucosylceramide synthase. J. Biochem. 111(2), 191-196 (1992).

    2. Lauer, S.A., Ghori, N., and Haldar, K. Sphingolipid synthesis as a target for chemotherapy against malaria parasites. Proc. Natl. Acad. Sci. USA 92(20), 9181-9185 (1995).

    3. Shen, W., Henry, A.G., Paumier, K.L., et al. Inhibition of glucosylceramide synthase stimulates autophagy flux in neurons. J. Neurochem. 129(5), 884-894 (2014).