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119567-63-4 | 4-Octadecene-1,3-diol, 2-(dimethylamino)-, (2S,3R,4E)-
CAS No: 119567-63-4 Catalog No: AG000IZ5 MDL No:MFCD00153960
Product Description
Catalog Number:
AG000IZ5
Chemical Name:
4-Octadecene-1,3-diol, 2-(dimethylamino)-, (2S,3R,4E)-
CAS Number:
119567-63-4
Molecular Formula:
C20H41NO2
Molecular Weight:
327.5450
MDL Number:
MFCD00153960
IUPAC Name:
(E,2S,3R)-2-(dimethylamino)octadec-4-ene-1,3-diol
InChI:
InChI=1S/C20H41NO2/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)19(18-22)21(2)3/h16-17,19-20,22-23H,4-15,18H2,1-3H3/b17-16+/t19-,20+/m0/s1
InChI Key:
YRXOQXUDKDCXME-YIVRLKKSSA-N
SMILES:
CCCCCCCCCCCCC/C=C/[C@H]([C@@H](N(C)C)CO)O
Properties
Complexity:
266
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
1
Exact Mass:
327.314g/mol
Formal Charge:
0
Heavy Atom Count:
23
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
327.553g/mol
Monoisotopic Mass:
327.314g/mol
Rotatable Bond Count:
16
Topological Polar Surface Area:
43.7A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.3
Literature
| Title | Journal |
|---|---|
| Sphingosine and FTY720 are potent inhibitors of the transient receptor potential melastatin 7 (TRPM7) channels. | British journal of pharmacology 20130301 |
| Pharmacologic recruitment of regulatory T cells as a therapy for ischemic acute kidney injury. | Kidney international 20120501 |
| Harnessing regulatory T cells for therapeutic purposes. | Kidney international 20120501 |
| Sphingosine kinase 1 knockdown reduces insulin synthesis and secretion in a rat insulinoma cell line. | Archives of biochemistry and biophysics 20120201 |
| [Antitumor effect of sphingosine kinase 1 inhibitor in combination with chemotherapy on SGC7901 gastric cancer cells in vitro]. | Zhonghua zhong liu za zhi [Chinese journal of oncology] 20120201 |
| Sphingosine kinase-1 pathway mediates high glucose-induced fibronectin expression in glomerular mesangial cells. | Molecular endocrinology (Baltimore, Md.) 20111201 |
| Pachastrissamine (jaspine B) and its stereoisomers inhibit sphingosine kinases and atypical protein kinase C. | Bioorganic & medicinal chemistry 20110915 |
| Endogenous sphingosine 1-phosphate regulates spontaneous glutamate release from mossy fiber terminals via S1P(3) receptors. | Life sciences 20110718 |
| Sphingolipid long chain base phosphates can regulate apoptotic-like programmed cell death in plants. | Biochemical and biophysical research communications 20110708 |
| [Effect of sphingosine kinase 1 on the apoptosis, migration and invasion of colon cancer HT-29 cells and its molecular mechanisms]. | Zhonghua zhong liu za zhi [Chinese journal of oncology] 20110301 |
| [Regulation of sphingosine kinase 1 in the TNF-α-induced expression of MUC5AC in airway epithelial cells]. | Zhonghua yi xue za zhi 20110215 |
| Bortezomib and sphingosine kinase inhibitor interact synergistically to induces apoptosis in BCR/ABl+ cells sensitive and resistant to STI571 through down-regulation Mcl-1. | Biochemical and biophysical research communications 20110204 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| Determination of sphingosine kinase activity in biological samples by liquid chromatography-tandem mass spectrometry. | Biomedical chromatography : BMC 20101001 |
| Sphingosine and FTY720 directly bind pro-survival 14-3-3 proteins to regulate their function. | Cellular signalling 20100901 |
| Sphingosine interaction with acidic leucine-rich nuclear phosphoprotein-32A (ANP32A) regulates PP2A activity and cyclooxygenase (COX)-2 expression in human endothelial cells. | The Journal of biological chemistry 20100827 |
| Sphingosine kinase inhibition alleviates endothelial permeability induced by thrombin and activated neutrophils. | Shock (Augusta, Ga.) 20100401 |
| Sphingosine kinase 1 regulates mucin production via ERK phosphorylation. | Pulmonary pharmacology & therapeutics 20100201 |
| The sphingosine kinase inhibitor N,N-dimethylsphingosine inhibits neointimal hyperplasia. | British journal of pharmacology 20100201 |
| Oxytocin stimulates in vitro angiogenesis via a Pyk-2/Src-dependent mechanism. | Experimental cell research 20091101 |
| Discovery of novel sphingosine kinase 1 inhibitors. | Bioorganic & medicinal chemistry letters 20091101 |
| Role of sphingosine-1-phosphate (S1P) and the S1P(2) receptor in allergen-induced, mast cell-dependent contraction of rat lung parenchymal strips. | Naunyn-Schmiedeberg's archives of pharmacology 20091001 |
| Development of an Alamar Blue viability assay in 384-well format for high throughput whole cell screening of Trypanosoma brucei brucei bloodstream form strain 427. | The American journal of tropical medicine and hygiene 20091001 |
| VEGF recruits lactosylceramide to induce endothelial cell adhesion molecule expression and angiogenesis in vitro and in vivo. | Glycoconjugate journal 20090701 |
| Iodophenyl tagged sphingosine derivatives: synthesis and preliminary biological evaluation. | Bioorganic & medicinal chemistry letters 20090701 |
| Synthesis and evaluation of sphingosine analogues as inhibitors of sphingosine kinases. | Journal of medicinal chemistry 20090625 |
| The importance of negative superhelicity in inducing the formation of G-quadruplex and i-motif structures in the c-Myc promoter: implications for drug targeting and control of gene expression. | Journal of medicinal chemistry 20090514 |
| Galpha(q)-mediated plasma membrane translocation of sphingosine kinase-1 and cross-activation of S1P receptors. | Biochimica et biophysica acta 20090501 |
| N,N-Dimethylsphingosine conjugates of poly-L-glutamic acid: synthesis, characterization, and initial biological evaluation. | Bioorganic & medicinal chemistry letters 20090201 |
| Small molecule activators of SIRT1 replicate signaling pathways triggered by calorie restriction in vivo. | BMC systems biology 20090101 |
| Anti-inflammatory effects of sphingosine kinase modulation in inflammatory arthritis. | Journal of immunology (Baltimore, Md. : 1950) 20081201 |
| A sphingosine kinase activity assay using direct infusion electrospray ionization tandem mass spectrometry. | Analytical biochemistry 20080901 |
| N-(4-Hydroxyphenyl)retinamide increases dihydroceramide and synergizes with dimethylsphingosine to enhance cancer cell killing. | Molecular cancer therapeutics 20080901 |
| Apoptosis induces expression of sphingosine kinase 1 to release sphingosine-1-phosphate as a 'come-and-get-me' signal. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20080801 |
| Brain-derived neurotrophic factor enhances the excitability of rat sensory neurons through activation of the p75 neurotrophin receptor and the sphingomyelin pathway. | The Journal of physiology 20080701 |
| N,N-Dimethyl-D-erythro-sphingosine inhibits store-operated Ca2+ entry in U937 monocytes. | Journal of pharmacological sciences 20080701 |
| Characterization of N,N,-dimethyl-D-erythro-sphingosine-induced apoptosis and signaling in U937 cells: independence of sphingosine kinase inhibition. | Prostaglandins & other lipid mediators 20080601 |
| Inhalation of sphingosine kinase inhibitor attenuates airway inflammation in asthmatic mouse model. | American journal of physiology. Lung cellular and molecular physiology 20080601 |
| Differential signaling of sphingosine derivatives in U937 human monocytes depends on the degree of N-methylation. | Prostaglandins & other lipid mediators 20080601 |
| Effects of phosphorylation of immunomodulatory agent FTY720 (fingolimod) on antiproliferative activity against breast and colon cancer cells. | Biological & pharmaceutical bulletin 20080601 |
| The role of sphingosine kinase in a murine model of allergic asthma. | Journal of immunology (Baltimore, Md. : 1950) 20080315 |
| Sphingolipid metabolites selectively elicit increases in nuclear calcium concentration in cell suspension cultures and in isolated nuclei of tobacco. | Cell calcium 20080101 |
| Trophic action of sphingosine 1-phosphate in denervated rat soleus muscle. | American journal of physiology. Cell physiology 20080101 |
| N, N-dimethyl-D-erythro-sphingosine increases intracellular Ca2+ concentration via Na+-Ca2+-exchanger in HCT116 human colon cancer cells. | Archives of pharmacal research 20080101 |
| Sphingolipids and the sphingosine kinase inhibitor, SKI II, induce BCL-2-independent apoptosis in human prostatic adenocarcinoma cells. | The Prostate 20071101 |
| Suppression of osteoclastogenesis by N,N-dimethyl-D-erythro-sphingosine: a sphingosine kinase inhibition-independent action. | Molecular pharmacology 20070801 |
| MAO-A-induced mitogenic signaling is mediated by reactive oxygen species, MMP-2, and the sphingolipid pathway. | Free radical biology & medicine 20070701 |
| The role of sphingosine 1-phosphate in the TNF-alpha induction of IL-8 gene expression in lung epithelial cells. | Gene 20070415 |
| Multiple actions of dimethylsphingosine in 1321N1 astrocytes. | Molecules and cells 20070227 |
| N,N-dimethylsphingosine-coumarin: synthesis, chemical characterization, and biological evaluation. | Bioconjugate chemistry 20070101 |
| Dimethylsphingosine and FTY720 inhibit the SK1 form but activate the SK2 form of sphingosine kinase from rat heart. | Journal of biochemical and molecular toxicology 20070101 |
| Pharmacologic manipulation of sphingosine kinase in retinal endothelial cells: implications for angiogenic ocular diseases. | Investigative ophthalmology & visual science 20061101 |
| Sphingosine kinase assay system with fluorescent detection in high performance liquid chromatography. | Archives of pharmacal research 20061101 |
| Characterization of Ca2+ influx induced by dimethylphytosphingosine and lysophosphatidylcholine in U937 monocytes. | Biochemical and biophysical research communications 20060929 |
| Low dose N, N-dimethylsphingosine is cardioprotective and activates cytosolic sphingosine kinase by a PKCepsilon dependent mechanism. | Cardiovascular research 20060901 |
| Intracellular sphingosine 1-phosphate mediates the increased excitability produced by nerve growth factor in rat sensory neurons. | The Journal of physiology 20060815 |
| Structure-activity relationships of dimethylsphingosine (DMS) derivatives and their effects on intracellular pH and Ca2+ in the U937 monocyte cell line. | Archives of pharmacal research 20060801 |
| Dimethylsphingosine regulates intracellular pH and Ca(2+) in human monocytes. | Journal of pharmacological sciences 20060401 |
| Novel role of sphingosine kinase 1 as a mediator of neurotrophin-3 action in oligodendrocyte progenitors. | Journal of neurochemistry 20051201 |
| Basal and induced sphingosine kinase 1 activity in A549 carcinoma cells: function in cell survival and IL-1beta and TNF-alpha induced production of inflammatory mediators. | Cellular signalling 20051001 |
| Sphingosine kinase regulates the sensitivity of Dictyostelium discoideum cells to the anticancer drug cisplatin. | Eukaryotic cell 20050101 |
| The intracellular action of sphingosine 1-phosphate in GPVI-mediated Ca2+ mobilization in platelets. | Thrombosis research 20050101 |
| Sphingosine 1-phosphate protects bovine oocytes from heat shock during maturation. | Biology of reproduction 20041201 |
| Enhancement of radiosensitivity by combined ceramide and dimethylsphingosine treatment in lung cancer cells. | Experimental & molecular medicine 20041031 |
| Anaphylatoxin signaling in human neutrophils. A key role for sphingosine kinase. | The Journal of biological chemistry 20041022 |
| Sphingosine kinase activation mediates ischemic preconditioning in murine heart. | Circulation 20041005 |
| mitochondrial ceramidase overexpression up-regulates Bcl-2 protein level in K562 cells, probably through its metabolite sphingosine-1-phosphate. | Zhongguo shi yan xue ye xue za zhi 20041001 |
| Genetic, biochemical, and transcriptional responses of Saccharomyces cerevisiae to the novel immunomodulator FTY720 largely mimic those of the natural sphingolipid phytosphingosine. | The Journal of biological chemistry 20040827 |
| Sphingosine kinase activation regulates hepatocyte growth factor induced migration of endothelial cells. | Experimental cell research 20040815 |
| Sphingosine kinase activity is required for sphingosine-mediated phospholipase D activation in C2C12 myoblasts. | The Biochemical journal 20040801 |
| The immune modulator FTY720 targets sphingosine-kinase-dependent migration of human monocytes in response to amyloid beta-protein and its precursor. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20040801 |
| Overexpression of sphingosine-1-phosphate lyase or inhibition of sphingosine kinase in Dictyostelium discoideum results in a selective increase in sensitivity to platinum-based chemotherapy drugs. | Eukaryotic cell 20040601 |
| Ceramide synthesis correlates with the posttranscriptional regulation of the sterol-regulatory element-binding protein. | Arteriosclerosis, thrombosis, and vascular biology 20040501 |
| Heparan sulfate proteoglycans are involved in opiate receptor-mediated cell migration. | Biochemistry 20040113 |
| Leukocyte motility in response to neuropeptides is heparan sulfate proteoglycan dependent. | Peptides 20030501 |
| Beta 1,4-galactosyltransferase (beta 4GalT)-IV is specific for GlcNAc 6-O-sulfate. Beta 4GalT-IV acts on keratan sulfate-related glycans and a precursor glycan of 6-sulfosialyl-Lewis X. | The Journal of biological chemistry 20030314 |
| Dimethylsphingosine increases cytosolic calcium and intracellular pH in human T lymphocytes. | Biochemical pharmacology 20030201 |
| Sphingosine kinase: a point of convergence in the action of diverse neutrophil priming agents. | Journal of immunology (Baltimore, Md. : 1950) 20021201 |
| D-erythro-N,N-dimethylsphingosine inhibits bFGF-induced proliferation of cerebral, aortic and coronary smooth muscle cells. | Atherosclerosis 20021001 |
| Expression of sphingosine kinase gene in the interactions between human gastric carcinoma cell and vascular endothelial cell. | World journal of gastroenterology 20020815 |
| Sphingosine kinase inhibitors in the apoptosis of leukaemia cells. | Leukemia research 20020401 |
| Sphingosine 1-phosphate stimulates rat mesangial cell proliferation from outside the cells. | Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association 20020401 |
| Effective cytotoxicity against human leukemias and chemotherapy-resistant leukemia cell lines by N-N-dimethylsphingosine. | Leukemia research 20020301 |
| Signalling pathways involved in the direct effects of IGFBP-5 on breast epithelial cell attachment and survival. | Journal of cellular biochemistry 20020101 |
| Depolarisation induces rapid and transient formation of intracellular sphingosine-1-phosphate. | FEBS letters 20011207 |
| Prolactin induces calcium influx and release from intracellular pools in human T lymphocytes by activation of tyrosine kinases. | Cellular signalling 20011101 |
| Sphingosine 1-phosphate antagonizes apoptosis of human leukemia cells by inhibiting release of cytochrome c and Smac/DIABLO from mitochondria. | Blood 20011101 |
| 1Alpha,25-dihydroxyvitamin D3 protects human keratinocytes from apoptosis by the formation of sphingosine-1-phosphate. | The Journal of investigative dermatology 20011101 |
| The lysophospholipids sphingosine-1-phosphate and lysophosphatidic acid enhance survival during hypoxia in neonatal rat cardiac myocytes. | Journal of molecular and cellular cardiology 20010901 |
| Sphingosine kinase regulates hepatoma cell differentiation: roles of hepatocyte nuclear factor and retinoid receptor. | Biochemical and biophysical research communications 20010831 |
| TNF-alpha-induced sphingosine 1-phosphate inhibits apoptosis through a phosphatidylinositol 3-kinase/Akt pathway in human hepatocytes. | Journal of immunology (Baltimore, Md. : 1950) 20010701 |
| Role of the sphingosine-1-phosphate receptor EDG-1 in PDGF-induced cell motility. | Science (New York, N.Y.) 20010302 |
| Sphingosine kinase expression regulates apoptosis and caspase activation in PC12 cells. | Journal of neurochemistry 20010301 |
| Activation of Gadd34 by diverse apoptotic signals and suppression of its growth inhibitory effects by apoptotic inhibitors. | International journal of cancer 20010220 |
| Differential regulation of protein tyrosine kinase on free radical production, granule enzyme release, and cytokine synthesis by activated murine peritoneal macrophages. | Biochemical pharmacology 20010101 |
| Involvement of sphingosine in mitochondria-dependent Fas-induced apoptosis of type II Jurkat T cells. | The Journal of biological chemistry 20000526 |
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