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124753-97-5,MFCD00171385
Catalog No.:AA000MMW

124753-97-5 | Hexanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-

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1mg
≥98%
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$26.00   $18.00
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5mg
≥98%
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$105.00   $73.00
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10mg
≥98%
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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:
AA000MMW
Chemical Name:
Hexanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-
CAS Number:
124753-97-5
Molecular Formula:
C24H47NO3
Molecular Weight:
397.6349
MDL Number:
MFCD00171385
SMILES:
CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCC)CO)O
Properties
Computed Properties
 
Complexity:
371  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
2  
Defined Bond Stereocenter Count:
1  
Heavy Atom Count:
28  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
20  
XLogP3:
7.5  

Literature

Title: Ceramide modulates pre-mRNA splicing to restore the expression of wild-type tumor suppressor p53 in deletion-mutant cancer cells.

Journal: Biochimica et biophysica acta 20141101

Title: Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine.

Journal: Bioorganic & medicinal chemistry 20121115

Title: Sphingomyelinase-induced adhesion of eryptotic erythrocytes to endothelial cells.

Journal: American journal of physiology. Cell physiology 20121101

Title: A shift in sphingolipid composition from C24 to C16 increases susceptibility to apoptosis in HeLa cells.

Journal: Biochimica et biophysica acta 20120701

Title: C6-ceramide and targeted inhibition of acid ceramidase induce synergistic decreases in breast cancer cell growth.

Journal: Breast cancer research and treatment 20120601

Title: Increasing ceramides sensitizes genistein-induced melanoma cell apoptosis and growth inhibition.

Journal: Biochemical and biophysical research communications 20120511

Title: Relevance of the salvage pathway to N-hexanoylsphingosine metabolic downregulation in human neurotumor cells: implications for apoptosis.

Journal: Drug metabolism letters 20120301

Title: Regulation of alternative splicing within the supraspliceosome.

Journal: Journal of structural biology 20120101

Title: C(6)-ceramide enhances phagocytic activity of Kupffer cells through the production of endogenous ceramides.

Journal: Molecules and cells 20111031

Title: P-glycoprotein antagonists confer synergistic sensitivity to short-chain ceramide in human multidrug-resistant cancer cells.

Journal: Experimental cell research 20110715

Title: Ceramide inhibits Kv currents and contributes to TP-receptor-induced vasoconstriction in rat and human pulmonary arteries.

Journal: American journal of physiology. Cell physiology 20110701

Title: ABCB1 protects kidney proximal tubule cells against cadmium-induced apoptosis: roles of cadmium and ceramide transport.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20110601

Title: Nanoliposomal ceramide prevents in vivo growth of hepatocellular carcinoma.

Journal: Gut 20110501

Title: Mitochondrially targeted ceramides preferentially promote autophagy, retard cell growth, and induce apoptosis.

Journal: Journal of lipid research 20110201

Title: Lipid component quantitation by thin layer chromatography.

Journal: Methods in molecular biology (Clifton, N.J.) 20110101

Title: Coupling in vitro and in vivo paradigm reveals a dose dependent inhibition of angiogenesis followed by initiation of autophagy by C6-ceramide.

Journal: International journal of biological sciences 20110101

Title: Peripheral neuropathy in the Twitcher mouse involves the activation of axonal caspase 3.

Journal: ASN neuro 20110101

Title: C6 ceramide potentiates curcumin-induced cell death and apoptosis in melanoma cell lines in vitro.

Journal: Cancer chemotherapy and pharmacology 20101001

Title: Metabolism of short-chain ceramide by human cancer cells--implications for therapeutic approaches.

Journal: Biochemical pharmacology 20100801

Title: Ceramide modulates HERG potassium channel gating by translocation into lipid rafts.

Journal: American journal of physiology. Cell physiology 20100701

Title: Cell-permeable ceramides act as novel regulators of U937 cell-cell adhesion mediated by CD29, CD98, and CD147.

Journal: Immunobiology 20100401

Title: Phospholipase D modulation by ceramide in senescence.

Journal: Molecular and cellular biochemistry 20100401

Title: Liposomes for drug delivery to mitochondria.

Journal: Methods in molecular biology (Clifton, N.J.) 20100101

Title: Long-chain ceramide produced in response to N-hexanoylsphingosine does not induce apoptosis in CHP-100 cells.

Journal: Lipids 20091101

Title: Ceramides: branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency.

Journal: Bioorganic & medicinal chemistry 20090215

Title: A role for ceramide in driving cancer cell resistance to doxorubicin.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20080701

Title: Apoptotic effects of dietary and synthetic sphingolipids in androgen-independent (PC-3) prostate cancer cells.

Journal: Lipids 20080201

Title: C(6)-ceramide inhibited Na(+) currents by intracellular Ca(2+) release in rat myoblasts.

Journal: Journal of cellular physiology 20071001

Title: Mitochondrial protein phosphatase 2A regulates cell death induced by simulated ischemia in kidney NRK-52E cells.

Journal: Cell cycle (Georgetown, Tex.) 20071001

Title: Ceramide-induced cell death in lens epithelial cells.

Journal: Molecular vision 20070910

Title: Cadmium-induced ceramide formation triggers calpain-dependent apoptosis in cultured kidney proximal tubule cells.

Journal: American journal of physiology. Cell physiology 20070901

Title: Nuclear localization of endogenous RGK proteins and modulation of cell shape remodeling by regulated nuclear transport.

Journal: Traffic (Copenhagen, Denmark) 20070901

Title: The functional effects of acid ceramidase overexpression in prostate cancer progression and resistance to chemotherapy.

Journal: Cancer biology & therapy 20070901

Title: De novo ceramide biosynthesis is associated with resveratrol-induced inhibition of ornithine decarboxylase activity.

Journal: Biochemical pharmacology 20070715

Title: Ceramide recruits and activates protein kinase C zeta (PKC zeta) within structured membrane microdomains.

Journal: The Journal of biological chemistry 20070427

Title: Solid-phase synthesis of a combinatorial library of dihydroceramide analogues and its activity in human alveolar epithelial cells.

Journal: Bioorganic & medicinal chemistry 20070101

Title: Sphingosine 1-phosphate: a novel stimulator of aldosterone secretion.

Journal: Journal of lipid research 20060601

Title: Colocalization of oxidized low-density lipoprotein, caspase-3, cyclooxygenase-2, and macrophage migration inhibitory factor in arteriosclerotic human carotid arteries.

Journal: Cell and tissue research 20051201

Title: Ultraviolet A-induced signaling involves a ceramide-mediated autocrine loop leading to ceramide de novo synthesis.

Journal: The Journal of investigative dermatology 20050901

Title: Resistance to TRAIL is associated with defects in ceramide signaling that can be overcome by exogenous C6-ceramide without requiring down-regulation of cellular FLICE inhibitory protein.

Journal: Molecular cancer therapeutics 20050901

Title: Regulatory roles of cell surface sialylation in susceptibility to sphingomyelinase in human diffuse large B cell lymphoma.

Journal: International journal of oncology 20050701

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

Journal: Biochimica et biophysica acta 20050601

Title: Ceramide alters endothelial cell permeability by a nonapoptotic mechanism.

Journal: British journal of pharmacology 20050501

Title: Systemic delivery of liposomal short-chain ceramide limits solid tumor growth in murine models of breast adenocarcinoma.

Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20050501

Title: Activation of serine/threonine protein phosphatase-1 is required for ceramide-induced survival of sympathetic neurons.

Journal: The Biochemical journal 20050201

Title: Potentiation of ceramide-induced apoptosis by p27kip1 overexpression.

Journal: Archives of pharmacal research 20050101

Title: Differential expression of proteins in response to ceramide-mediated stress signal in colon cancer cells by 2-D gel electrophoresis and MALDI-TOF-MS.

Journal: Journal of proteome research 20050101

Title: TNFalpha reduces the expression of peroxisome proliferator-activated receptor gamma (PPARgamma) via the production of ceramide and activation of atypical PKC.

Journal: Diabetes research and clinical practice 20041201

Title: Involvement of growth differentiation factor-15/macrophage inhibitory cytokine-1 (GDF-15/MIC-1) in oxLDL-induced apoptosis of human macrophages in vitro and in arteriosclerotic lesions.

Journal: Cell and tissue research 20041101

Title: Synergistic effect of interleukin (IL)-1alpha and ceramide analogue on the production of IL-6, IL-8, and macrophage colony-stimulating factor by endometrial stromal cells.

Journal: Fertility and sterility 20041001

Title: Ceramide synthesis correlates with the posttranscriptional regulation of the sterol-regulatory element-binding protein.

Journal: Arteriosclerosis, thrombosis, and vascular biology 20040501

Title: Plasma membrane aquaporin activity can affect the rate of apoptosis but is inhibited after apoptotic volume decrease.

Journal: American journal of physiology. Cell physiology 20040401

Title: Sphingomyelin synthase as a potential target for D609-induced apoptosis in U937 human monocytic leukemia cells.

Journal: Experimental cell research 20040115

Title: Nicotine-induced neuroprotection against N-methyl-D-aspartic acid or beta-amyloid peptide occur through independent mechanisms distinguished by pro-inflammatory cytokines.

Journal: Journal of neurochemistry 20031201

Title: Mitochondrial cytochrome c release mediates ceramide-induced activator protein 2 activation and gene expression in keratinocytes.

Journal: The Journal of biological chemistry 20031128

Title: Liposomal delivery enhances short-chain ceramide-induced apoptosis of breast cancer cells.

Journal: The Journal of pharmacology and experimental therapeutics 20031101

Title: Ceramide accumulation precedes caspase-3 activation during apoptosis of A549 human lung adenocarcinoma cells.

Journal: American journal of physiology. Lung cellular and molecular physiology 20030601

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

Journal: Biochemical pharmacology 20030515

Title: Modulation of transforming growth factor-beta (TGF-beta) signaling by endogenous sphingolipid mediators.

Journal: The Journal of biological chemistry 20030314

Title: Differential roles of 2, 6, and 8 carbon ceramides on the modulation of gap junctional communication and apoptosis during carcinogenesis.

Journal: Cancer letters 20030227

Title: Anti-apoptotic role of phospholipase D isozymes in the glutamate-induced cell death.

Journal: Experimental & molecular medicine 20030227

Title: Activation of the Drosophila MLK by ceramide reveals TNF-alpha and ceramide as agonists of mammalian MLK3.

Journal: Molecular cell 20021201

Title: Modulation of CYP3A4 expression by ceramide in human colon carcinoma HT-29 cells.

Journal: Biochemical and biophysical research communications 20021115

Title: Synthetic ceramides induce growth arrest or apoptosis by altering cellular redox status.

Journal: Archives of biochemistry and biophysics 20021101

Title: Dual effect of ceramide on human endothelial cells: induction of oxidative stress and transcriptional upregulation of endothelial nitric oxide synthase.

Journal: Circulation 20021022

Title: Influence of ceramide metabolism on P-glycoprotein function in immature acute myeloid leukemia KG1a cells.

Journal: Molecular pharmacology 20020801

Title: Telomerase positive human diploid fibroblasts are resistant to replicative senescence but not premature senescence induced by chemical reagents.

Journal: Biogerontology 20020101

Title: Ceramide-mediated apoptosis in lung epithelial cells is regulated by glutathione.

Journal: American journal of respiratory cell and molecular biology 20011201

Title: Synergistic effect of interleukin-1alpha and ceramide analogue on production of prostaglandin E2 and F2alpha by endometrial stromal cells.

Journal: American journal of reproductive immunology (New York, N.Y. : 1989) 20011201

Title: [Rapid induction of senescence-like changes in human umbilic vein endothelial cells(HUVECs) by C6 ceramide].

Journal: Shi yan sheng wu xue bao 20011201

Title: Ceramide accelerates dephosphorylation of extracellular signal-regulated kinase 1/2 to decrease prostaglandin D(2) production in RBL-2H3 cells.

Journal: Archives of biochemistry and biophysics 20011115

Title: Ceramide modulates nicotinic receptor-dependent Ca(2+) signaling in rat chromaffin cells.

Journal: Journal of neuroscience research 20011115

Title: Ceramide inhibits the outward potassium current in rat pinealocytes.

Journal: Journal of neurochemistry 20011001

Title: Ceramide inhibits axonal growth and nerve growth factor uptake without compromising the viability of sympathetic neurons.

Journal: The Journal of biological chemistry 20010928

Title: Bax-dependent apoptosis induced by ceramide in HL-60 cells.

Journal: FEBS letters 20010914

Title: Molecular mechanisms of ceramide-mediated telomerase inhibition in the A549 human lung adenocarcinoma cell line.

Journal: The Journal of biological chemistry 20010831

Title: Role of ceramide in mediating the inhibition of telomerase activity in A549 human lung adenocarcinoma cells.

Journal: The Journal of biological chemistry 20010706

Title: Fumonisin-induced tumor necrosis factor-alpha expression in a porcine kidney cell line is independent of sphingoid base accumulation induced by ceramide synthase inhibition.

Journal: Toxicology and applied pharmacology 20010701

Title: Inhibitory actions of ceramide upon PKC-epsilon/ERK interactions.

Journal: American journal of physiology. Cell physiology 20010601

Title: Psychosine is as potent an inducer of cell death as C6-ceramide in cultured fibroblasts and in MOCH-1 cells.

Journal: Neurochemical research 20010601

Title: Induction of apoptotic cell death and prevention of tumor growth by ceramide analogues in metastatic human colon cancer.

Journal: Cancer research 20010201

Title: Nitric oxide inhibits apoptosis via AP-1-dependent CD95L transactivation.

Journal: Cancer research 20000501

Title: Induction of the manganese superoxide dismutase gene by sphingomyelinase and ceramide.

Journal: Journal of neurochemistry 19990801

Title: Ceramide-induced apoptosis is mediated by caspase activation independently from retinoblastoma protein post-translational modification.

Journal: Biochemical and biophysical research communications 19980224

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SDS
Tags:124753-97-5 Molecular Formula|124753-97-5 MDL|124753-97-5 SMILES|124753-97-5 Hexanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]- |Organic_Building_Blocks