HPA-12 | CAS#383418-30-2 | Inhibitor

MedKoo Cat#: 565784 | Name: HPA-12

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

HPA-12 is a novel potent inhibitor of cert, binding to the ceramide-binding pocket in the cert start domain

Chemical Structure

HPA-12

CAS#383418-30-2

Theoretical Analysis

MedKoo Cat#: 565784

Name: HPA-12

CAS#: 383418-30-2

Chemical Formula: C22H37NO3

Exact Mass: 363.2773

Molecular Weight: 363.54

Elemental Analysis: C, 72.69; H, 10.26; N, 3.85; O, 13.20

Price and Availability

Size	Price	Availability	Quantity
5mg	USD 550.00	2 Weeks

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Related CAS #

No Data

Synonym

HPA-12; HPA 12; HPA12; (1R, 3S)-HPA-12; (1R, 3S) HPA 12; (1R, 3S)HPA12

IUPAC/Chemical Name

N-[(2R,4S)-1,4-dihydroxy-4-phenylbutan-2-yl]dodecanamide

InChi Key

YCAKBKAOFSILDC-RTWAWAEBSA-N

InChi Code

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

SMILES Code

CCCCCCCCCCCC(N[C@H](C[C@H](O)C1=CC=CC=C1)CO)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 363.54 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Crivelli SM, Paulus A, Markus J, Bauwens M, Berkes D, De Vries HE, Mulder MT, Walter J, Mottaghy FM, Losen M, Martinez-Martinez P. Synthesis, Radiosynthesis, and Preliminary in vitro and in vivo Evaluation of the Fluorinated Ceramide Trafficking Inhibitor (HPA-12) for Brain Applications. J Alzheimers Dis. 2017;60(3):783-794. doi: 10.3233/JAD-161231. PubMed PMID: 28922150. 2: Santos C, Fleury L, Rodriguez F, Markus J, Berkeš D, Daïch A, Ausseil F, Baudoin-Dehoux C, Ballereau S, Génisson Y. The CERT antagonist HPA-12: first practical synthesis and individual binding evaluation of the four stereoisomers. Bioorg Med Chem. 2015 May 1;23(9):2004-9. doi: 10.1016/j.bmc.2015.03.019. Epub 2015 Mar 12. PubMed PMID: 25818765. 3: Reddy AA, Prasad KR. Synthesis of β-Amino Ketones by Addition of Aryl Methyl Ketones to Sulfinimines: Application to the Total Synthesis of HPA-12, Norsedamine, and Sedamine. J Org Chem. 2017 Dec 15;82(24):13488-13499. doi: 10.1021/acs.joc.7b02611. Epub 2017 Nov 30. PubMed PMID: 29160073. 4: Saied EM, Diederich S, Arenz C. Facile synthesis of the CERT inhibitor HPA-12 and some novel derivatives. Chem Asian J. 2014 Aug;9(8):2092-4. doi: 10.1002/asia.201402241. Epub 2014 Jun 2. PubMed PMID: 24888419. 5: Scheiblich H, Schlütter A, Golenbock DT, Latz E, Martinez-Martinez P, Heneka MT. Activation of the NLRP3 inflammasome in microglia: the role of ceramide. J Neurochem. 2017 Dec;143(5):534-550. doi: 10.1111/jnc.14225. Epub 2017 Oct 26. PubMed PMID: 28940479. 6: Ďuriš A, Daïch A, Santos C, Fleury L, Ausseil F, Rodriguez F, Ballereau S, Génisson Y, Berkeš D. Asymmetric Synthesis and Binding Study of New Long-Chain HPA-12 Analogues as Potent Ligands of the Ceramide Transfer Protein CERT. Chemistry. 2016 May 4;22(19):6676-86. doi: 10.1002/chem.201505121. Epub 2016 Mar 31. PubMed PMID: 27031925. 7: Ueno M, Huang YY, Yamano A, Kobayashi S. Revised stereochemistry of ceramide-trafficking inhibitor HPA-12 by X-ray crystallography analysis. Org Lett. 2013 Jun 7;15(11):2869-71. doi: 10.1021/ol401101u. Epub 2013 May 23. PubMed PMID: 23701643. 8: Xiao ZF, Yao CZ, Kang YB. Ruthenium-catalyzed asymmetric N-demethylative rearrangement of isoxazolidines and its application in the asymmetric total syntheses of (-)-(1R,3S)-HPA-12 and (+)-(1S,3R)-HPA-12. Org Lett. 2014 Dec 19;16(24):6512-4. doi: 10.1021/ol503261h. Epub 2014 Nov 25. PubMed PMID: 25423582. 9: Kanojia SV, Chatterjee S, Chattopadhyay S, Goswami D. A chemoenzymatic synthesis of ceramide trafficking inhibitor HPA-12. Beilstein J Org Chem. 2019 Feb 18;15:490-496. doi: 10.3762/bjoc.15.42. eCollection 2019. PubMed PMID: 30873232; PubMed Central PMCID: PMC6404422. 10: Berkeš D, Daïch A, Santos C, Ballereau S, Génisson Y. Chemistry and Biology of HPAs: A Family of Ceramide Trafficking Inhibitors. Chemistry. 2016 Dec 5;22(49):17514-17525. doi: 10.1002/chem.201602947. Epub 2016 Sep 15. Review. PubMed PMID: 27628428. 11: Morita N, Kono R, Fukui K, Miyazawa A, Masu H, Azumaya I, Ban S, Hashimoto Y, Okamoto I, Tamura O. BF3-Mediated cis-Selective Cycloaddition of O-Silyloxime with Alkenes. J Org Chem. 2015 May 1;80(9):4797-802. doi: 10.1021/acs.joc.5b00426. Epub 2015 Apr 22. PubMed PMID: 25859817. 12: Ďuriš A, Wiesenganger T, Moravčíková D, Baran P, Kožíšek J, Daïch A, Berkeš D. Expedient and practical synthesis of CERT-dependent ceramide trafficking inhibitor HPA-12 and its analogues. Org Lett. 2011 Apr 1;13(7):1642-5. doi: 10.1021/ol2001057. Epub 2011 Feb 25. PubMed PMID: 21351771. 13: Yasuda S, Kitagawa H, Ueno M, Ishitani H, Fukasawa M, Nishijima M, Kobayashi S, Hanada K. A novel inhibitor of ceramide trafficking from the endoplasmic reticulum to the site of sphingomyelin synthesis. J Biol Chem. 2001 Nov 23;276(47):43994-4002. Epub 2001 Sep 6. Erratum in: J Biol Chem. 2013 Aug 16;288(33):24162. PubMed PMID: 11546801. 14: Yao CZ, Xiao ZF, Ning XS, Liu J, Zhang XW, Kang YB. Synthesis of syn-1,3-aminoalcohols via a Ru-catalyzed N-demethylative rearrangement of isoxazolidines and its application in a three-step total synthesis of HPA-12. Org Lett. 2014 Nov 7;16(21):5824-6. doi: 10.1021/ol502956j. Epub 2014 Oct 27. PubMed PMID: 25347750. 15: Koch-Edelmann S, Banhart S, Saied EM, Rose L, Aeberhard L, Laue M, Doellinger J, Arenz C, Heuer D. The cellular ceramide transport protein CERT promotes Chlamydia psittaci infection and controls bacterial sphingolipid uptake. Cell Microbiol. 2017 Oct;19(10). doi: 10.1111/cmi.12752. Epub 2017 Jun 15. PubMed PMID: 28544656. 16: Santos C, Stauffert F, Ballereau S, Dehoux C, Rodriguez F, Bodlenner A, Compain P, Génisson Y. Iminosugar-based ceramide mimicry for the design of new CERT START domain ligands. Bioorg Med Chem. 2017 Mar 15;25(6):1984-1989. doi: 10.1016/j.bmc.2017.02.026. Epub 2017 Feb 14. PubMed PMID: 28237558. 17: Zhao Y, Ishigami M, Nagao K, Hanada K, Kono N, Arai H, Matsuo M, Kioka N, Ueda K. ABCB4 exports phosphatidylcholine in a sphingomyelin-dependent manner. J Lipid Res. 2015 Mar;56(3):644-52. doi: 10.1194/jlr.M056622. Epub 2015 Jan 19. PubMed PMID: 25601960; PubMed Central PMCID: PMC4340311. 18: Nakamura Y, Matsubara R, Kitagawa H, Kobayashi S, Kumagai K, Yasuda S, Hanada K. Stereoselective synthesis and structure-activity relationship of novel ceramide trafficking inhibitors. (1R,3R)-N-(3-hydroxy-1-hydroxymethyl-3-phenylpropyl)dodecanamide and its analogues. J Med Chem. 2003 Aug 14;46(17):3688-95. PubMed PMID: 12904073. 19: Kobayashi S, Matsubara R, Kitagawa H. Catalytic, asymmetric Mannich-type reactions of N-acylimino esters for direct formation of N-acylated amino acid derivatives. Efficient synthesis of a novel inhibitor of ceramide trafficking, HPA-12. Org Lett. 2002 Jan 10;4(1):143-5. PubMed PMID: 11772111. 20: Hullin-Matsuda F, Tomishige N, Sakai S, Ishitsuka R, Ishii K, Makino A, Greimel P, Abe M, Laviad EL, Lagarde M, Vidal H, Saito T, Osada H, Hanada K, Futerman AH, Kobayashi T. Limonoid compounds inhibit sphingomyelin biosynthesis by preventing CERT protein-dependent extraction of ceramides from the endoplasmic reticulum. J Biol Chem. 2012 Jul 13;287(29):24397-411. doi: 10.1074/jbc.M112.356733. Epub 2012 May 17. PubMed PMID: 22605339; PubMed Central PMCID: PMC3397866.