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10140-30-4 | 4-Octadecene-1,3-diol, 2-amino-
CAS No: 10140-30-4 Catalog No: AG0004ES MDL No:
Product Description
Catalog Number:
AG0004ES
Chemical Name:
4-Octadecene-1,3-diol, 2-amino-
CAS Number:
10140-30-4
Molecular Formula:
C18H37NO2
Molecular Weight:
299.4919
IUPAC Name:
2-aminooctadec-4-ene-1,3-diol
InChI:
InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3
InChI Key:
WWUZIQQURGPMPG-UHFFFAOYSA-N
SMILES:
CCCCCCCCCCCCCC=CC(C(CO)N)O
EC Number:
204-651-3
Properties
Complexity:
231
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
299.282g/mol
Formal Charge:
0
Heavy Atom Count:
21
Hydrogen Bond Acceptor Count:
3
Hydrogen Bond Donor Count:
3
Isotope Atom Count:
0
Molecular Weight:
299.499g/mol
Monoisotopic Mass:
299.282g/mol
Rotatable Bond Count:
15
Topological Polar Surface Area:
66.5A^2
Undefined Atom Stereocenter Count:
2
Undefined Bond Stereocenter Count:
1
XLogP3:
5.3
Literature
| Title | Journal |
|---|---|
| Sphingosine-1-phosphate-induced airway hyper-reactivity in rodents is mediated by the sphingosine-1-phosphate type 3 receptor. | The Journal of pharmacology and experimental therapeutics 20120801 |
| Interplay between SAFE and RISK pathways in sphingosine-1-phosphate-induced cardioprotection. | Cardiovascular drugs and therapy 20120601 |
| Sphingosine-1-phosphate-induced release of TIMP-2 from vascular smooth muscle cells inhibits angiogenesis. | Journal of cell science 20120501 |
| S1P2 receptor mediates sphingosine-1-phosphate-induced fibronectin expression via MAPK signaling pathway in mesangial cells under high glucose condition. | Experimental cell research 20120501 |
| Regulation of metabolism and transport of sphingosine-1-phosphate in mammalian cells. | Molecular and cellular biochemistry 20120401 |
| ABCA1, ABCG1, and SR-BI: Transit of HDL-associated sphingosine-1-phosphate. | Clinica chimica acta; international journal of clinical chemistry 20120218 |
| Sphingosine kinase-signaling pathway: a possible therapeutic target for post-operative cognitive dysfunction. | Acta anaesthesiologica Scandinavica 20120201 |
| Health effects of dietary phospholipids. | Lipids in health and disease 20120101 |
| Macrophage-associated mesenchymal stem cells assume an activated, migratory, pro-inflammatory phenotype with increased IL-6 and CXCL10 secretion. | PloS one 20120101 |
| Detailed structural analysis of lipids directly on tissue specimens using a MALDI-SpiralTOF-Reflectron TOF mass spectrometer. | PloS one 20120101 |
| CD69 modulates sphingosine-1-phosphate-induced migration of skin dendritic cells. | The Journal of investigative dermatology 20110701 |
| Sphingosine-1-phosphate-induced inflammation involves receptor tyrosine kinase transactivation in vascular cells: upregulation in hypertension. | Hypertension (Dallas, Tex. : 1979) 20110401 |
| Role for peroxynitrite in sphingosine-1-phosphate-induced hyperalgesia in rats. | Pain 20110301 |
| Report on the 2nd scientific meeting of the 'Verein zur Förderung des Wissenschaftlichen Nachwuchses in der Neurologie' (NEUROWIND e.V.) held in Motzen, Germany, Oct. 29'th - Oct. 31'st, 2010. | Experimental & translational stroke medicine 20110101 |
| S1P, dihydro-S1P and C24:1-ceramide levels in the HDL-containing fraction of serum inversely correlate with occurrence of ischemic heart disease. | Lipids in health and disease 20110101 |
| Selectivity and specificity of sphingosine-1-phosphate receptor ligands: caveats and critical thinking in characterizing receptor-mediated effects. | Frontiers in pharmacology 20110101 |
| Modulation of immunoglobulin production by invariant Vα19-Jα33 TCR-bearing cells. | PloS one 20110101 |
| A concerted HIF-1α/MT1-MMP signalling axis regulates the expression of the 3BP2 adaptor protein in hypoxic mesenchymal stromal cells. | PloS one 20110101 |
| Sphingosine but not sphingosine-1-phosphate stimulates suicidal erythrocyte death. | Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20110101 |
| The impact of bioactive lipids on cardiovascular development. | Stem cells international 20110101 |
| A sphingosine kinase form 2 knockout sensitizes mouse myocardium to ischemia/reoxygenation injury and diminishes responsiveness to ischemic preconditioning. | Oxidative medicine and cellular longevity 20110101 |
| The primary cilium as a biomarker in the hypoxic adaptation of bone marrow-derived mesenchymal stromal cells: a role for the secreted frizzled-related proteins. | Biomarker insights 20110101 |
| Identification of specific inhibitors for a trypanosomatid RNA editing reaction. | RNA (New York, N.Y.) 20101201 |
| Sphingolipids mediate formation of mRNA processing bodies during the heat-stress response of Saccharomyces cerevisiae. | The Biochemical journal 20101001 |
| Effects of motilin on intracellular free calcium in cultured smooth muscle cells from the antrum of neonatal rats. | Acta physiologica (Oxford, England) 20100501 |
| Enhanced Ca2+ storage in sphingosine-1-phosphate lyase-deficient fibroblasts. | Cellular signalling 20100301 |
| The lectin concanavalin-A signals MT1-MMP catalytic independent induction of COX-2 through an IKKgamma/NF-kappaB-dependent pathway. | Journal of cell communication and signaling 20100301 |
| Marginal zone precursor B cells as cellular agents for type I IFN-promoted antigen transport in autoimmunity. | Journal of immunology (Baltimore, Md. : 1950) 20100101 |
| PI3Kp110-, Src-, FAK-dependent and DOCK2-independent migration and invasion of CXCL13-stimulated prostate cancer cells. | Molecular cancer 20100101 |
| Sphingosine kinase-1 (SphK-1) regulates Mycobacterium smegmatis infection in macrophages. | PloS one 20100101 |
| Deoxysphingoid bases as plasma markers in diabetes mellitus. | Lipids in health and disease 20100101 |
| Overexpression of sphingosine kinase 1 is associated with salivary gland carcinoma progression and might be a novel predictive marker for adjuvant therapy. | BMC cancer 20100101 |
| Ectopic and eutopic stromal endometriotic cells have a damaged ceramide signaling pathway to apoptosis. | Fertility and sterility 20091201 |
| Ceramides: branched alkyl chains in the sphingolipid siblings of diacylglycerol improve biological potency. | Bioorganic & medicinal chemistry 20090215 |
| Role of sphingosine kinases and lipid phosphate phosphatases in regulating spatial sphingosine 1-phosphate signalling in health and disease. | Cellular signalling 20090101 |
| Mechanisms of sphingosine-1-phosphate-induced akt-dependent smooth muscle cell migration. | Surgery 20090101 |
| Mechanisms of the noxious inflammatory cycle in cystic fibrosis. | Respiratory research 20090101 |
| Ste20-related proline/alanine-rich kinase (SPAK) regulated transcriptionally by hyperosmolarity is involved in intestinal barrier function. | PloS one 20090101 |
| Elevated serum levels of arachidonoyl-lysophosphatidic acid and sphingosine 1-phosphate in systemic sclerosis. | International journal of medical sciences 20090101 |
| Sphingosine protects aging hearts from ischemia/reperfusion injury: Superiority to sphingosine 1-phosphate and ischemic pre- and post-conditioning. | Oxidative medicine and cellular longevity 20090101 |
| Use of a decoy peptide to purify p21 activated kinase-1 in cardiac muscle and identification of ceramide-related activation. | Biologics : targets & therapy 20081201 |
| Rap1b regulates B cell development, homing, and T cell-dependent humoral immunity. | Journal of immunology (Baltimore, Md. : 1950) 20080901 |
| Dysregulated angiogenesis in B-chronic lymphocytic leukemia: morphologic, immunohistochemical, and flow cytometric evidence. | Diagnostic pathology 20080101 |
| Modified Ca(v)1.4 expression in the Cacna1f(nob2) mouse due to alternative splicing of an ETn inserted in exon 2. | PloS one 20080101 |
| Stereoselective synthesis of (2S,3S,4Z)-4-fluoro-1,3-dihydroxy-2-(octadecanoylamino)octadec-4-ene, [(Z)-4-fluoroceramide], and its phase behavior at the air/water interface. | Beilstein journal of organic chemistry 20080101 |
| Sphingosine-1-phosphate-induced oxygen free radical generation in smooth muscle cell migration requires Galpha12/13 protein-mediated phospholipase C activation. | Journal of vascular surgery 20071201 |
| Edaravone mimics sphingosine-1-phosphate-induced endothelial barrier enhancement in human microvascular endothelial cells. | American journal of physiology. Cell physiology 20071101 |
| Src-dependent phosphorylation of membrane type I matrix metalloproteinase on cytoplasmic tyrosine 573: role in endothelial and tumor cell migration. | The Journal of biological chemistry 20070525 |
| Sphingosine 1-phosphate triggers apoptotic signal for B16 melanoma cells via ERK and caspase activation. | Journal of Korean medical science 20070401 |
| Targeting sphingosine-1-phosphate for cancer therapy. | British journal of cancer 20061106 |
| Cooperation of matrix metalloproteinases with the RhoA/Rho kinase and mitogen-activated protein kinase kinase-1/extracellular signal-regulated kinase signaling pathways is required for the sphingosine-1-phosphate-induced mobilization of marrow-derived stromal cells. | Stem cells (Dayton, Ohio) 20061101 |
| [Evidence for the presence of motilin receptor and a study on the mechanism of motilin induced Ca2+ signaling in rat myenteric neurons]. | Sichuan da xue xue bao. Yi xue ban = Journal of Sichuan University. Medical science edition 20060901 |
| The Rap GTPases mediate CXCL13- and sphingosine1-phosphate-induced chemotaxis, adhesion, and Pyk2 tyrosine phosphorylation in B lymphocytes. | European journal of immunology 20060801 |
| The involvement of protein kinases in signalling of opioid agonist FK 33-824 in porcine granulosa cells. | Animal reproduction science 20060101 |
| The chemopreventive properties of chlorogenic acid reveal a potential new role for the microsomal glucose-6-phosphate translocase in brain tumor progression. | Cancer cell international 20060101 |
| Activation of the sphingosine kinase-signaling pathway by high glucose mediates the proinflammatory phenotype of endothelial cells. | Circulation research 20051028 |
| Porcine, mouse and human galactose 3-O-sulphotransferase-2 enzymes have different substrate specificities; the porcine enzyme requires basic compounds for its catalytic activity. | The Biochemical journal 20051001 |
| Apical uptake and transepithelial transport of sphingosine monomers through intact human intestinal epithelial cells: physicochemical and molecular modeling studies. | Archives of biochemistry and biophysics 20050801 |
| Acid and neutral sphingomyelinase, ceramide synthase, and acid ceramidase activities in cutaneous aging. | Experimental dermatology 20050801 |
| Vascular function and sphingosine-1-phosphate regulate development of the dorsal pancreatic mesenchyme. | Development (Cambridge, England) 20050301 |
| A rapid radioassay for sphingosine kinase. | Analytical biochemistry 20050201 |
| [The effect of protein kinase C alpha on expression of developmental genes during differentiation of mouse embryonic stem cells into neuron-like cells in vitro]. | [Zhonghua yan ke za zhi] Chinese journal of ophthalmology 20050201 |
| Sphingosine-1-phosphate-induced smooth muscle cell migration involves the mammalian target of rapamycin. | Journal of vascular surgery 20050101 |
| The diversity of bacterial pathogenicity mechanisms. | Genome biology 20050101 |
| Sphingosine-1-phosphate-induced intracellular Ca2+ mobilization in human endothelial cells. | Endothelium : journal of endothelial cell research 20050101 |
| Effects of synthetic sphingosine-1-phosphate analogs on arachidonic acid metabolism and cell death. | Biochemical pharmacology 20041201 |
| Differential regulation of ERK1/2 and p38(MAPK) by components of the Rho signaling pathway during sphingosine-1-phosphate-induced smooth muscle cell migration. | The Journal of surgical research 20041201 |
| The response of phospholipase C/protein kinase C and adenylyl cyclase/protein kinase A pathways in porcine theca interna cells to opioid agonist FK 33-824. | Domestic animal endocrinology 20041101 |
| Subcellular compartmentalization of ceramide metabolism: MAM (mitochondria-associated membrane) and/or mitochondria? | The Biochemical journal 20040901 |
| Sphingolipids in the chemoprevention of colon cancer. | Frontiers in bioscience : a journal and virtual library 20040901 |
| Interaction of cortactin and Arp2/3 complex is required for sphingosine-1-phosphate-induced endothelial cell remodeling. | Experimental cell research 20040801 |
| Isoform-selectivity of PKC inhibitors acting at the regulatory and catalytic domain of mammalian PKC-alpha, -betaI, -delta, -eta and -zeta. | Journal of enzyme inhibition and medicinal chemistry 20031201 |
| Comparative analysis of functional assays for characterization of agonist ligands at G protein-coupled receptors. | Journal of biomolecular screening 20031001 |
| Sphingosine-1-phosphate-induced ERK activation protects human melanocytes from UVB-induced apoptosis. | Archives of pharmacal research 20030901 |
| Ras/Raf1-dependent signal in sphingosine-1-phosphate-induced tube formation in human coronary artery endothelial cells. | Biochemical and biophysical research communications 20030711 |
| Matrix metalloproteinase regulation of sphingosine-1-phosphate-induced angiogenic properties of bone marrow stromal cells. | Experimental hematology 20030701 |
| Highly effective non-viral gene transfer into vascular smooth muscle cells of cultured resistance arteries demonstrated by genetic inhibition of sphingosine-1-phosphate-induced vasoconstriction. | Journal of vascular research 20030101 |
| Tumor necrosis factor-alpha-associated lysosomal permeabilization is cathepsin B dependent. | American journal of physiology. Gastrointestinal and liver physiology 20021001 |
| Antifungal activity of bifunctional sphingolipids. Intramolecular synergism within long-chain alpha,omega-bis-aminoalcohols. | Bioorganic & medicinal chemistry letters 20020819 |
| Distinct signals via Rho GTPases and Src drive shape changes by thrombin and sphingosine-1-phosphate in endothelial cells. | Journal of cell science 20020615 |
| Choline phosphate potentiates sphingosine-1-phosphate-induced Raf-1 kinase activation dependent of Ras--phosphatidylinositol-3-kinase pathway. | Cellular signalling 20020401 |
| [Regulation of Rho family G proteins and cell motility by the Edg family of sphingosin 1-phosphate receptors]. | Tanpakushitsu kakusan koso. Protein, nucleic acid, enzyme 20020301 |
| Involvement of endothelial nitric oxide in sphingosine-1-phosphate-induced angiogenesis. | Arteriosclerosis, thrombosis, and vascular biology 20020101 |
| Scale-up of a myoblast culture process. | Journal of biotechnology 20010913 |
| Sphingolipid metabolic changes during chiral C2-ceramides induced apoptosis in human leukemia cells. | Archives of pharmacal research 20010401 |
| Mutant NG108-15 cells (NG-CR72) deficient in GM1 synthase respond aberrantly to axonogenic stimuli and are vulnerable to calcium-induced apoptosis: they are rescued with LIGA-20. | Journal of neurochemistry 20010201 |
| Extracellular mechanism through the Edg family of receptors might be responsible for sphingosine-1-phosphate-induced regulation of DNA synthesis and migration of rat aortic smooth-muscle cells. | The Biochemical journal 20010101 |
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