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454863

D-erythro-MAPP

Name: D-<i>erythro</i>-MAPP
Brand: MM

A synthetic analog of ceramide.

Synonym(s):

D-erythro-MAPP, (1S,2R)-D- erythro-2-(N-Myristoylamino)-1-phenyl-1-propanol, AC Inhibitor II, Acid Ceramidase Inhibitor II, D-e-MAPP, (1S,2R)-D-erythro-2-(N-Myristoylamino)-1-phenyl-1-propanol, AC Inhibitor II, Acid Ceramidase Inhibitor II, D-e-MAPP

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About This Item

Empirical Formula (Hill Notation):

C₂₃H₃₉NO₂

CAS Number:

143492-38-0

Molecular Weight:

361.56

UNSPSC Code:

12352211

Assay:

≥98% (NMR)

Form:

solid

Quality level:

100

Storage condition:

OK to freeze

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Quality Level

100

assay

≥98% (NMR)

form

solid

manufacturer/tradename

Calbiochem^®

storage condition

OK to freeze

solubility

ethanol: 5 mg/mL

shipped in

ambient

storage temp.

−20°C

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

General description

A synthetic analog of ceramide. Shown to selectively inhibit alkaline ceraminidase both in vitro and in HL-60 cells (IC₅₀ = 1-5 µM for alkaline ceramides versus IC₅₀ >500 µM for acid ceraminidase). This inhibition results in and over 3-fold increase in endogenous ceramide in treated cells due to a lack of breakdown of ceramide to sphingosine.

Biochem/physiol Actions

Cell permeable: yes

Primary Target
Alkaline ceramidase

Product does not compete with ATP.

Reversible: no

Target IC₅₀: 1-5 µM for alkaline ceramidase versus >500 µM for acid ceramidase

Preparation Note

Following reconstitution, aliquot and freeze (-20°C). Stock solutions are stable for up to 1 month at -20°C.

Other Notes

Bielawska, A., et al. 1996. J. Biol. Chem. 271, 12646.
Hannun, Y.A. 1996. Science274, 1855.

Legal Information

CALBIOCHEM is a registered trademark of Merck KGaA, Darmstadt, Germany

Disclaimer

Toxicity: Standard Handling (A)

Storage Class

11 - Combustible Solids

wgk

WGK 1

flash_point_f

Not applicable

flash_point_c