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Merck
CN

SML2894

Sigma-Aldrich

HPA-12

≥98% (HPLC)

别名:

(1R,3S)-HPA-12, (1R,3S)-N-(3-Hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide, 16ASC1859, N-[(1R,3S)-3-Hydroxy-1-(hydroxymethyl)-3-phenylpropyl]dodecanamide, N-[(2R,4S)-1,4-Dihydroxy-4-phenylbutan-2-yl]dodecanamide

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About This Item

经验公式(希尔记法):
C22H37NO3
分子量:
363.53
MDL编号:
UNSPSC代码:
51111800
NACRES:
NA.77

质量水平

方案

≥98% (HPLC)

表单

powder

颜色

white to beige

溶解性

DMSO: 2 mg/mL, clear

储存温度

2-8°C

SMILES字符串

N([C@@H](CO)C[C@H](O)c1ccccc1)C(=O)CCCCCCCCCCC

InChI

1S/C22H37NO3/c1-2-3-4-5-6-7-8-9-13-16-22(26)23-20(18-24)17-21(25)19-14-11-10-12-15-19/h10-12,14-15,20-21,24-25H,2-9,13,16-18H2,1H3,(H,23,26)/t20-,21+/m1/s1

InChI key

YCAKBKAOFSILDC-RTWAWAEBSA-N

生化/生理作用

(1R,3S)-HPA-12 is a ceramide (Cer) analog that acts as a Cer transporter (CERT) antagonist and selectively inhibits cellular Cer conversion to sphingomyelin (SM), but not to glucosylceramide, by blocking CERT-mediated Cer ER-to-Golgi transport. Common culture dosing range: 1-10 μM.

储存分类代码

11 - Combustible Solids

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number

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Masaharu Ueno et al.
Organic letters, 15(11), 2869-2871 (2013-05-25)
In response to Berkeš's report revising the stereochemistry of HPA-12, an important ceramide-trafficking inhibitor that was discovered and synthesized and its stereochemistry determined in 2001, the synthesis and the stereochemistry were reinvestigated. A large-scale synthetic method for HPA-12 based on
Hannah Scheiblich et al.
Journal of neurochemistry, 143(5), 534-550 (2017-09-25)
Inflammation within the CNS is a major component of many neurodegenerative diseases. A characteristic feature is the generation of microglia-derived factors that play an essential role in the immune response. IL-1β is a pro-inflammatory cytokine released by activated microglia, able
Sophia Koch-Edelmann et al.
Cellular microbiology, 19(10) (2017-05-26)
Chlamydiaceae are bacterial pathogens that cause diverse diseases in humans and animals. Despite their broad host and tissue tropism, all Chlamydia species share an obligate intracellular cycle of development and have evolved sophisticated mechanisms to interact with their eukaryotic host
Cécile L Bandet et al.
Diabetes, 67(7), 1258-1271 (2018-05-16)
One main mechanism of insulin resistance (IR), a key feature of type 2 diabetes, is the accumulation of saturated fatty acids (FAs) in the muscles of obese patients with type 2 diabetes. Understanding the mechanism that underlies lipid-induced IR is
Andrej Ďuriš et al.
Organic letters, 13(7), 1642-1645 (2011-03-01)
The practical stereodivergent route to both syn- and anti-diastereomers of 1-substituted 3-aminobutane-1,4-diols based on the crystallization-induced asymmetric transformation (CIAT) approach was completed. This led to the revision of the reported stereochemistry of the first inhibitor of CERT-dependent ceramide trafficking HPA-12

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