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24696-26-2,MFCD00871748
Catalog No.:AA00I4NK

24696-26-2 | Hexadecanamide,N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-

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1mg
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5mg
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$112.00   $78.00
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10mg
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25mg
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00I4NK
Chemical Name:
Hexadecanamide,N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-
CAS Number:
24696-26-2
Molecular Formula:
C34H67NO3
Molecular Weight:
537.9007
MDL Number:
MFCD00871748
SMILES:
CCCCCCCCCCCCCCCC(=O)NC(C(C=CCCCCCCCCCCCCC)O)CO
Properties
Computed Properties
 
Complexity:
508  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
38  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
30  
XLogP3:
12.9  

Literature

Title: Insights into myalgic encephalomyelitis/chronic fatigue syndrome phenotypes through comprehensive metabolomics.

Journal: Scientific reports 20180101

Title: An Intestinal Farnesoid X Receptor-Ceramide Signaling Axis Modulates Hepatic Gluconeogenesis in Mice.

Journal: Diabetes 20170301

Title: Inhibition of interleukin-1β-induced endothelial tissue factor expression by the synthetic cannabinoid WIN 55,212-2.

Journal: Oncotarget 20160920

Title: Lipidomic analyses of female mice lacking hepatic lipase and endothelial lipase indicate selective modulation of plasma lipid species.

Journal: Lipids 20140601

Title: Acid sphingomyelinase-ceramide system mediates effects of antidepressant drugs.

Journal: Nature medicine 20130701

Title: Activation of the unfolded protein response pathway causes ceramide accumulation in yeast and INS-1E insulinoma cells.

Journal: Journal of lipid research 20120301

Title: C16 ceramide is crucial for triacylglycerol-induced apoptosis in macrophages.

Journal: Cell death & disease 20120301

Title: The thermotropism and prototropism of ternary mixtures of ceramide C16, cholesterol and palmitic acid. An exploratory study.

Journal: Chemistry and physics of lipids 20111001

Title: Intracellular localization of organized lipid domains of C16-ceramide/cholesterol.

Journal: Journal of structural biology 20110701

Title: IRF8 regulates acid ceramidase expression to mediate apoptosis and suppresses myelogeneous leukemia.

Journal: Cancer research 20110415

Title: Ceramide-induced activation of cytosolic NADH/cytochrome c electron transport pathway: An additional source of energy for apoptosis.

Journal: Archives of biochemistry and biophysics 20101215

Title: Activation of ceramide synthase 6 by celecoxib leads to a selective induction of C16:0-ceramide.

Journal: Biochemical pharmacology 20101201

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Cholesterol displaces palmitoylceramide from its tight packing with palmitoylsphingomyelin in the absence of a liquid-disordered phase.

Journal: Biophysical journal 20100809

Title: Triggering role of acid sphingomyelinase in endothelial lysosome-membrane fusion and dysfunction in coronary arteries.

Journal: American journal of physiology. Heart and circulatory physiology 20100301

Title: Antiapoptotic roles of ceramide-synthase-6-generated C16-ceramide via selective regulation of the ATF6/CHOP arm of ER-stress-response pathways.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20100101

Title: Endothelial membrane remodeling is obligate for anti-angiogenic radiosensitization during tumor radiosurgery.

Journal: PloS one 20100101

Title: Coexistence of immiscible mixtures of palmitoylsphingomyelin and palmitoylceramide in monolayers and bilayers.

Journal: Biophysical journal 20091115

Title: The proapoptotic C16-ceramide-dependent pathway requires the death-promoting factor Btf in colon adenocarcinoma cells.

Journal: Journal of proteome research 20091001

Title: Ceramide-1-phosphate, in contrast to ceramide, is not segregated into lateral lipid domains in phosphatidylcholine bilayers.

Journal: Biophysical journal 20090318

Title: Ceramide synthase 6 modulates TRAIL sensitivity and nuclear translocation of active caspase-3 in colon cancer cells.

Journal: Oncogene 20090226

Title: De novo N-palmitoylsphingosine synthesis is the major biochemical mechanism of ceramide accumulation following p53 up-regulation.

Journal: Prostaglandins & other lipid mediators 20080601

Title: De novo C16- and C24-ceramide generation contributes to spontaneous neutrophil apoptosis.

Journal: Journal of leukocyte biology 20070601

Title: Cationic long-chain ceramide LCL-30 induces cell death by mitochondrial targeting in SW403 cells.

Journal: Molecular cancer therapeutics 20060601

Title: Importance of C16 ceramide accumulation during apoptosis in prostate cancer cells.

Journal: International journal of urology : official journal of the Japanese Urological Association 20060201

Title: Rapid phase change of lipid microdomains in giant vesicles induced by conversion of sphingomyelin to ceramide.

Journal: Biochimica et biophysica acta 20060201

Title: Roles for C16-ceramide and sphingosine 1-phosphate in regulating hepatocyte apoptosis in response to tumor necrosis factor-alpha.

Journal: The Journal of biological chemistry 20050729

Title: Molecular associations and surface-active properties of short- and long-N-acyl chain ceramides.

Journal: Biochimica et biophysica acta 20050601

Title: A central role for ceramide in the age-related acceleration of apoptosis in the female germline.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20050501

Title: Sphingomyelinase causes endothelium-dependent vasorelaxation through endothelial nitric oxide production without cytosolic Ca(2+) elevation.

Journal: FEBS letters 20050117

Title: R(+)-methanandamide-induced cyclooxygenase-2 expression in H4 human neuroglioma cells: possible involvement of membrane lipid rafts.

Journal: Biochemical and biophysical research communications 20041112

Title: Cell surface ceramide generation precedes and controls FcgammaRII clustering and phosphorylation in rafts.

Journal: The Journal of biological chemistry 20040827

Title: Ceramide metabolite, not intact ceramide molecule, may be responsible for cellular toxicity.

Journal: The Biochemical journal 20040615

Title: C16 ceramide accumulates following androgen ablation in LNCaP prostate cancer cells.

Journal: The Prostate 20030915

Title: Ceramide inhibits the potassium channel Kv1.3 by the formation of membrane platforms.

Journal: Biochemical and biophysical research communications 20030613

Title: Elevation of de novo ceramide synthesis in tumor masses and the role of microsomal dihydroceramide synthase.

Journal: International journal of cancer 20030520

Title: Mechanisms involved in exogenous C2- and C6-ceramide-induced cancer cell toxicity.

Journal: Biochemical pharmacology 20030515

Title: BcR-induced apoptosis involves differential regulation of C16 and C24-ceramide formation and sphingolipid-dependent activation of the proteasome.

Journal: The Journal of biological chemistry 20030425

Title: Ceramide channels increase the permeability of the mitochondrial outer membrane to small proteins.

Journal: The Journal of biological chemistry 20020726

Title: The effect of ceramide on phosphatidylcholine membranes: a deuterium NMR study.

Journal: Biophysical journal 20020601

Title: Ceramide inhibition of mammalian phospholipase D1 and D2 activities is antagonized by phosphatidylinositol 4,5-bisphosphate.

Journal: Biochemistry 20010918

Title: Molecular mechanisms of ceramide-mediated CD95 clustering.

Journal: Biochemical and biophysical research communications 20010622

Title: The total syntheses of D-erythro-sphingosine, N-palmitoylsphingosine (ceramide), and glucosylceramide (cerebroside) via an azidosphingosine analog.

Journal: Chemistry and physics of lipids 20010601

Title: Induction of apoptosis through B-cell receptor cross-linking occurs via de novo generated C16-ceramide and involves mitochondria.

Journal: The Journal of biological chemistry 20010427

Title: Interfacial interactions of ceramide with dimyristoylphosphatidylcholine: impact of the N-acyl chain.

Journal: Biophysical journal 20010201

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Tags:24696-26-2 Molecular Formula|24696-26-2 MDL|24696-26-2 SMILES|24696-26-2 Hexadecanamide,N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecenyl]-