An inhibitor of alkaline ceramidase
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D-erythro-MAPP

Item No. 10165

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1S,5S,6R)-5-hydroxy-5-[(1E,3E,5E)-7-[(2-hydroxy-5-oxo-1-cyclopenten-1-yl)amino]-7-oxo-1,3,5-heptatrien-1-yl]-2-oxo-7-oxabicyclo[4.1.0]hept-3-en-3-yl]-2E,4E,6R-trimethyl-2,4-decadienamide
CAS Number
143492-38-0
Synonyms
  • (1S,2R-D-erythro-2-N-myristoylamino)-1-phenyl-1-propanol
Molecular Formula
C23H39NO2
Formula Weight
361.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 20 mg/mlDMSO: 0.1 mg/mlEthanol: 20 mg/mlEthanol:PBS (pH 7.2) (1:2): 0.5 mg/ml
SMILES
O[C@H]([C@H](N(C(CCCCCCCCCCCCC)=O)[H])C)C1=CC=CC=C1
InChi Code
InChI=1S/C23H39NO2/c1-3-4-5-6-7-8-9-10-11-12-16-19-22(25)24-20(2)23(26)21-17-14-13-15-18-21/h13-15,17-18,20,23,26H,3-12,16,19H2,1-2H3,(H,24,25)/t20-,23-/m1/s1
InChi Key
YLAZEWZHIRBZDA-NFBKMPQASA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    500 µg

    $13

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    1 mg

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    5 mg

    $77

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    10 mg

    $132

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    Product Description

    D-erythro-MAPP is a derivative of ceramide and an inhibitor of alkaline ceramidase (Ki = 2-13 µM; IC50 = 1-5 µM).1 It is selective for alkaline ceramidase over acid ceramidase (IC50 = >500 µM) as well as the serine/threonine protein phosphatase CAPP at concentrations up to 10 µM. D-erythro-MAPP increases intracellular ceramide levels, induces cell cycle arrest at the G0/G1 phase, and inhibits growth of HL-60 promyelocytic leukemia cells in a time- and concentration-dependent manner.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Bielawska, A., Greenberg, M.S., Perry, D., et al. (1S,2R)-D-erythro-2-(N-myristoylamino)-1-phenyl-1-propanol as an inhibitor of ceramidase. The Journal of Biological Chemisty 271, 12646-12654 (1996).