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Merck
CN

SML2358

D-NMAPPD

≥98% (HPLC)

Synonym(s):

(1R, 2R)-N-myristoylamino-4′-nitro-phenylpropandiol-1, 3, (1R,2R)-B13, B13, N-[(1R,2R)-2-Hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]tetradecanamide, [R-(R*,R*)]-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-tetradecanamide

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About This Item

Empirical Formula (Hill Notation):
C23H38N2O5
CAS Number:
35922-06-6
Molecular Weight:
422.56
UNSPSC Code:
12352200
MDL number:
MFCD08062172
NACRES:
NA.21

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SMILES string

[N+](=O)([O-])c1ccc(cc1)[C@@H](O)[C@H](NC(=O)CCCCCCCCCCCCC)CO

InChI

1S/C23H38N2O5/c1-2-3-4-5-6-7-8-9-10-11-12-13-22(27)24-21(18-26)23(28)19-14-16-20(17-15-19)25(29)30/h14-17,21,23,26,28H,2-13,18H2,1H3,(H,24,27)/t21-,23-/m1/s1

InChI key

XUSDVLHKNBOGJY-FYYLOGMGSA-N

assay

≥98% (HPLC)

form

powder

optical activity

[α]/D -28 to -34, c = 0.1 in chloroform-d

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Related Categories

Biochem/physiol Actions

D-NMAPPD (B13), a myristoyl-CoA analog, is a cell penetrant inhibitor of N-myristoyltransferases that suppressed FRS2α (fibroblast growth factor receptor substrate 2) myristoylation. D-NMAPPD inhibits wild-type FGFRs and drug-resistant mutants (FGFRsDRM) oncogenic signaling in cancer cells. D-NMAPPD potently inhibits growth of xenograft tumors in mice. D-NMAPPD is a potent inhibitor of ceramidase that elevates endogenous ceramide levels and suppress growth of cancer cells.
cell penetrant inhibitor of N-myristoyltransferases that suppressed FRS2α myristoylation; potent inhibitor of ceramidase that elevates endogenous ceramide levels.

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000182507
0000182507
0000053899
0000053900
0000043544

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Induction of Inflammation Disrupts the Negative Interplay between STING and S1P Axis That Is Observed during Physiological Conditions in the Lung.
Terlizzi, et al.
International Journal of Molecular Sciences, 24 (2023)
Mototeru Yamane et al.
Biochemistry and biophysics reports, 11, 174-181 (2017-09-29)
In this study, we showed that the dual addition of glucosyl ceramide synthase and ceramidase inhibitors to A549 cell culture led to the possibility of ceramide channel formation via endogenous palmitoyl-ceramide accumulation with an increase in cholesterol contents in the
Qianjin Li et al.
The Journal of biological chemistry, 293(17), 6434-6448 (2018-03-16)
Fibroblast growth factor (FGF)/FGF receptor (FGFR) signaling facilitates tumor initiation and progression. Although currently approved inhibitors of FGFR kinase have shown therapeutic benefit in clinical trials, overexpression or mutations of FGFRs eventually confer drug resistance and thereby abrogate the desired
Michela Terlizzi et al.
Cells, 11(16) (2022-08-27)
Sphingosine-1-phosphate (S1P) is involved in inflammatory signaling/s associated with the development of respiratory disorders, including cancer. However, the underlying mechanism/s are still elusive. The aim of this study was to investigate the role of S1P on circulating blood cells obtained

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