SML2894

HPA-12

Name: HPA-12
Brand: SIGMA
Price: 263 USD
Availability: InStock

≥98% (HPLC), Cer transporter (CERT) antagonist, powder

Synonym(s):

(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

Empirical Formula (Hill Notation):

C₂₂H₃₇NO₃

CAS Number:

383418-30-2

Molecular Weight:

363.53

MDL number:

MFCD29472535

UNSPSC Code:

51111800

NACRES:

NA.77

Key Documents

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Product Name

HPA-12, ≥98% (HPLC)

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

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

Related Categories

Bioactive Small Molecules

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This Item	SML2358	SML2870	SML2365
Sigma-Aldrich SML2894 HPA-12	Sigma-Aldrich SML2358 D-NMAPPD	Sigma-Aldrich SML2870 BI 99179	Sigma-Aldrich SML2365 Phenprocoumon
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥97% (HPLC)
form powder	form powder	form powder	form powder
Quality Level 100	Quality Level -	Quality Level 100	Quality Level -
storage temp. 2-8°C	storage temp. 2-8°C	storage temp. −20°C	storage temp. 2-8°C
solubility DMSO: 2 mg/mL, clear	solubility DMSO: 2 mg/mL, clear	solubility DMSO: 2 mg/mL, clear	solubility DMSO: 2 mg/mL, clear
color white to beige	color white to beige	color white to beige	color white to beige

Biochem/physiol Actions

(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.

Ceramide transporter (CERT) antagonist that inhibits Cer-to-sphingomyelin (SM) conversion by blocking CERT-mediated ceramide ER-to-Golgi transport.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Activation of the NLRP3 inflammasome in microglia: the role of ceramide.

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

Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis.

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

A novel inhibitor of ceramide trafficking from the endoplasmic reticulum to the site of sphingomyelin synthesis.

S Yasuda et al.

The Journal of biological chemistry, 276(47), 43994-44002 (2001-09-08)

Ceramide produced at the endoplasmic reticulum (ER) is transported to the lumen of the Golgi apparatus for conversion to sphingomyelin (SM). N-(3-Hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide (HPA-12) is a novel analog of ceramide. Metabolic labeling experiments showed that HPA-12 inhibits conversion of ceramide to

Expedient and practical synthesis of CERT-dependent ceramide trafficking inhibitor HPA-12 and its analogues.

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

The cellular ceramide transport protein CERT promotes Chlamydia psittaci infection and controls bacterial sphingolipid uptake.

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

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HPA-12