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124753-97-5 | Hexanamide, N-[(1S,2R,3E)-2-hydroxy-1-(hydroxymethyl)-3-heptadecen-1-yl]-
CAS No: 124753-97-5 Catalog No: AG000MPO MDL No:MFCD00870174
Product Description
Catalog Number:
AG000MPO
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:
MFCD00870174
IUPAC Name:
N-[(E,2S,3R)-1,3-dihydroxyoctadec-4-en-2-yl]hexanamide
InChI:
InChI=1S/C24H47NO3/c1-3-5-7-8-9-10-11-12-13-14-15-16-18-19-23(27)22(21-26)25-24(28)20-17-6-4-2/h18-19,22-23,26-27H,3-17,20-21H2,1-2H3,(H,25,28)/b19-18+/t22-,23+/m0/s1
InChI Key:
NPRJSFWNFTXXQC-QFWQFVLDSA-N
SMILES:
CCCCCCCCCCCCC/C=C/[C@H]([C@@H](NC(=O)CCCCC)CO)O
UNII:
038753E78J
Properties
Complexity:
371
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
1
Exact Mass:
397.356g/mol
Formal Charge:
0
Heavy Atom Count:
28
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
397.644g/mol
Monoisotopic Mass:
397.356g/mol
Rotatable Bond Count:
20
Topological Polar Surface Area:
69.6A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
7.5
Literature
| Title | Journal |
|---|---|
| Ceramide modulates pre-mRNA splicing to restore the expression of wild-type tumor suppressor p53 in deletion-mutant cancer cells. | Biochimica et biophysica acta 20141101 |
| Exploration of natural compounds as sources of new bifunctional scaffolds targeting cholinesterases and beta amyloid aggregation: the case of chelerythrine. | Bioorganic & medicinal chemistry 20121115 |
| Sphingomyelinase-induced adhesion of eryptotic erythrocytes to endothelial cells. | American journal of physiology. Cell physiology 20121101 |
| A shift in sphingolipid composition from C24 to C16 increases susceptibility to apoptosis in HeLa cells. | Biochimica et biophysica acta 20120701 |
| C6-ceramide and targeted inhibition of acid ceramidase induce synergistic decreases in breast cancer cell growth. | Breast cancer research and treatment 20120601 |
| Increasing ceramides sensitizes genistein-induced melanoma cell apoptosis and growth inhibition. | Biochemical and biophysical research communications 20120511 |
| Relevance of the salvage pathway to N-hexanoylsphingosine metabolic downregulation in human neurotumor cells: implications for apoptosis. | Drug metabolism letters 20120301 |
| Regulation of alternative splicing within the supraspliceosome. | Journal of structural biology 20120101 |
| C(6)-ceramide enhances phagocytic activity of Kupffer cells through the production of endogenous ceramides. | Molecules and cells 20111031 |
| P-glycoprotein antagonists confer synergistic sensitivity to short-chain ceramide in human multidrug-resistant cancer cells. | Experimental cell research 20110715 |
| Ceramide inhibits Kv currents and contributes to TP-receptor-induced vasoconstriction in rat and human pulmonary arteries. | American journal of physiology. Cell physiology 20110701 |
| ABCB1 protects kidney proximal tubule cells against cadmium-induced apoptosis: roles of cadmium and ceramide transport. | Toxicological sciences : an official journal of the Society of Toxicology 20110601 |
| Nanoliposomal ceramide prevents in vivo growth of hepatocellular carcinoma. | Gut 20110501 |
| Mitochondrially targeted ceramides preferentially promote autophagy, retard cell growth, and induce apoptosis. | Journal of lipid research 20110201 |
| Lipid component quantitation by thin layer chromatography. | Methods in molecular biology (Clifton, N.J.) 20110101 |
| Coupling in vitro and in vivo paradigm reveals a dose dependent inhibition of angiogenesis followed by initiation of autophagy by C6-ceramide. | International journal of biological sciences 20110101 |
| Peripheral neuropathy in the Twitcher mouse involves the activation of axonal caspase 3. | ASN neuro 20110101 |
| C6 ceramide potentiates curcumin-induced cell death and apoptosis in melanoma cell lines in vitro. | Cancer chemotherapy and pharmacology 20101001 |
| Metabolism of short-chain ceramide by human cancer cells--implications for therapeutic approaches. | Biochemical pharmacology 20100801 |
| Ceramide modulates HERG potassium channel gating by translocation into lipid rafts. | American journal of physiology. Cell physiology 20100701 |
| Cell-permeable ceramides act as novel regulators of U937 cell-cell adhesion mediated by CD29, CD98, and CD147. | Immunobiology 20100401 |
| Phospholipase D modulation by ceramide in senescence. | Molecular and cellular biochemistry 20100401 |
| Liposomes for drug delivery to mitochondria. | Methods in molecular biology (Clifton, N.J.) 20100101 |
| Long-chain ceramide produced in response to N-hexanoylsphingosine does not induce apoptosis in CHP-100 cells. | Lipids 20091101 |
| Ceramides: branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency. | Bioorganic & medicinal chemistry 20090215 |
| A role for ceramide in driving cancer cell resistance to doxorubicin. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20080701 |
| Apoptotic effects of dietary and synthetic sphingolipids in androgen-independent (PC-3) prostate cancer cells. | Lipids 20080201 |
| C(6)-ceramide inhibited Na(+) currents by intracellular Ca(2+) release in rat myoblasts. | Journal of cellular physiology 20071001 |
| Mitochondrial protein phosphatase 2A regulates cell death induced by simulated ischemia in kidney NRK-52E cells. | Cell cycle (Georgetown, Tex.) 20071001 |
| Ceramide-induced cell death in lens epithelial cells. | Molecular vision 20070910 |
| Cadmium-induced ceramide formation triggers calpain-dependent apoptosis in cultured kidney proximal tubule cells. | American journal of physiology. Cell physiology 20070901 |
| Nuclear localization of endogenous RGK proteins and modulation of cell shape remodeling by regulated nuclear transport. | Traffic (Copenhagen, Denmark) 20070901 |
| The functional effects of acid ceramidase overexpression in prostate cancer progression and resistance to chemotherapy. | Cancer biology & therapy 20070901 |
| De novo ceramide biosynthesis is associated with resveratrol-induced inhibition of ornithine decarboxylase activity. | Biochemical pharmacology 20070715 |
| Ceramide recruits and activates protein kinase C zeta (PKC zeta) within structured membrane microdomains. | The Journal of biological chemistry 20070427 |
| Solid-phase synthesis of a combinatorial library of dihydroceramide analogues and its activity in human alveolar epithelial cells. | Bioorganic & medicinal chemistry 20070101 |
| Sphingosine 1-phosphate: a novel stimulator of aldosterone secretion. | Journal of lipid research 20060601 |
| Colocalization of oxidized low-density lipoprotein, caspase-3, cyclooxygenase-2, and macrophage migration inhibitory factor in arteriosclerotic human carotid arteries. | Cell and tissue research 20051201 |
| Ultraviolet A-induced signaling involves a ceramide-mediated autocrine loop leading to ceramide de novo synthesis. | The Journal of investigative dermatology 20050901 |
| 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. | Molecular cancer therapeutics 20050901 |
| Regulatory roles of cell surface sialylation in susceptibility to sphingomyelinase in human diffuse large B cell lymphoma. | International journal of oncology 20050701 |
| Molecular associations and surface-active properties of short- and long-N-acyl chain ceramides. | Biochimica et biophysica acta 20050601 |
| Ceramide alters endothelial cell permeability by a nonapoptotic mechanism. | British journal of pharmacology 20050501 |
| Systemic delivery of liposomal short-chain ceramide limits solid tumor growth in murine models of breast adenocarcinoma. | Clinical cancer research : an official journal of the American Association for Cancer Research 20050501 |
| Activation of serine/threonine protein phosphatase-1 is required for ceramide-induced survival of sympathetic neurons. | The Biochemical journal 20050201 |
| Potentiation of ceramide-induced apoptosis by p27kip1 overexpression. | Archives of pharmacal research 20050101 |
| 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 of proteome research 20050101 |
| TNFalpha reduces the expression of peroxisome proliferator-activated receptor gamma (PPARgamma) via the production of ceramide and activation of atypical PKC. | Diabetes research and clinical practice 20041201 |
| 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. | Cell and tissue research 20041101 |
| 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. | Fertility and sterility 20041001 |
| Ceramide synthesis correlates with the posttranscriptional regulation of the sterol-regulatory element-binding protein. | Arteriosclerosis, thrombosis, and vascular biology 20040501 |
| Plasma membrane aquaporin activity can affect the rate of apoptosis but is inhibited after apoptotic volume decrease. | American journal of physiology. Cell physiology 20040401 |
| Sphingomyelin synthase as a potential target for D609-induced apoptosis in U937 human monocytic leukemia cells. | Experimental cell research 20040115 |
| Nicotine-induced neuroprotection against N-methyl-D-aspartic acid or beta-amyloid peptide occur through independent mechanisms distinguished by pro-inflammatory cytokines. | Journal of neurochemistry 20031201 |
| Mitochondrial cytochrome c release mediates ceramide-induced activator protein 2 activation and gene expression in keratinocytes. | The Journal of biological chemistry 20031128 |
| Liposomal delivery enhances short-chain ceramide-induced apoptosis of breast cancer cells. | The Journal of pharmacology and experimental therapeutics 20031101 |
| Ceramide accumulation precedes caspase-3 activation during apoptosis of A549 human lung adenocarcinoma cells. | American journal of physiology. Lung cellular and molecular physiology 20030601 |
| Mechanisms involved in exogenous C2- and C6-ceramide-induced cancer cell toxicity. | Biochemical pharmacology 20030515 |
| Modulation of transforming growth factor-beta (TGF-beta) signaling by endogenous sphingolipid mediators. | The Journal of biological chemistry 20030314 |
| Differential roles of 2, 6, and 8 carbon ceramides on the modulation of gap junctional communication and apoptosis during carcinogenesis. | Cancer letters 20030227 |
| Anti-apoptotic role of phospholipase D isozymes in the glutamate-induced cell death. | Experimental & molecular medicine 20030227 |
| Activation of the Drosophila MLK by ceramide reveals TNF-alpha and ceramide as agonists of mammalian MLK3. | Molecular cell 20021201 |
| Modulation of CYP3A4 expression by ceramide in human colon carcinoma HT-29 cells. | Biochemical and biophysical research communications 20021115 |
| Synthetic ceramides induce growth arrest or apoptosis by altering cellular redox status. | Archives of biochemistry and biophysics 20021101 |
| Dual effect of ceramide on human endothelial cells: induction of oxidative stress and transcriptional upregulation of endothelial nitric oxide synthase. | Circulation 20021022 |
| Influence of ceramide metabolism on P-glycoprotein function in immature acute myeloid leukemia KG1a cells. | Molecular pharmacology 20020801 |
| Telomerase positive human diploid fibroblasts are resistant to replicative senescence but not premature senescence induced by chemical reagents. | Biogerontology 20020101 |
| Ceramide-mediated apoptosis in lung epithelial cells is regulated by glutathione. | American journal of respiratory cell and molecular biology 20011201 |
| Synergistic effect of interleukin-1alpha and ceramide analogue on production of prostaglandin E2 and F2alpha by endometrial stromal cells. | American journal of reproductive immunology (New York, N.Y. : 1989) 20011201 |
| [Rapid induction of senescence-like changes in human umbilic vein endothelial cells(HUVECs) by C6 ceramide]. | Shi yan sheng wu xue bao 20011201 |
| Ceramide accelerates dephosphorylation of extracellular signal-regulated kinase 1/2 to decrease prostaglandin D(2) production in RBL-2H3 cells. | Archives of biochemistry and biophysics 20011115 |
| Ceramide modulates nicotinic receptor-dependent Ca(2+) signaling in rat chromaffin cells. | Journal of neuroscience research 20011115 |
| Ceramide inhibits the outward potassium current in rat pinealocytes. | Journal of neurochemistry 20011001 |
| Ceramide inhibits axonal growth and nerve growth factor uptake without compromising the viability of sympathetic neurons. | The Journal of biological chemistry 20010928 |
| Bax-dependent apoptosis induced by ceramide in HL-60 cells. | FEBS letters 20010914 |
| Molecular mechanisms of ceramide-mediated telomerase inhibition in the A549 human lung adenocarcinoma cell line. | The Journal of biological chemistry 20010831 |
| Role of ceramide in mediating the inhibition of telomerase activity in A549 human lung adenocarcinoma cells. | The Journal of biological chemistry 20010706 |
| Fumonisin-induced tumor necrosis factor-alpha expression in a porcine kidney cell line is independent of sphingoid base accumulation induced by ceramide synthase inhibition. | Toxicology and applied pharmacology 20010701 |
| Inhibitory actions of ceramide upon PKC-epsilon/ERK interactions. | American journal of physiology. Cell physiology 20010601 |
| Psychosine is as potent an inducer of cell death as C6-ceramide in cultured fibroblasts and in MOCH-1 cells. | Neurochemical research 20010601 |
| Induction of apoptotic cell death and prevention of tumor growth by ceramide analogues in metastatic human colon cancer. | Cancer research 20010201 |
| Nitric oxide inhibits apoptosis via AP-1-dependent CD95L transactivation. | Cancer research 20000501 |
| Induction of the manganese superoxide dismutase gene by sphingomyelinase and ceramide. | Journal of neurochemistry 19990801 |
| Ceramide-induced apoptosis is mediated by caspase activation independently from retinoblastoma protein post-translational modification. | Biochemical and biophysical research communications 19980224 |
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