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19794-97-9 | 1,3-Octadecanediol, 2-amino-, 1-(dihydrogen phosphate), (2S,3R)-
CAS No: 19794-97-9 Catalog No: AG002B6V MDL No:
Product Description
Catalog Number:
AG002B6V
Chemical Name:
1,3-Octadecanediol, 2-amino-, 1-(dihydrogen phosphate), (2S,3R)-
CAS Number:
19794-97-9
Molecular Formula:
C18H40NO5P
Molecular Weight:
381.4877
IUPAC Name:
[(2S,3R)-2-amino-3-hydroxyoctadecyl] dihydrogen phosphate
InChI:
InChI=1S/C18H40NO5P/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(20)17(19)16-24-25(21,22)23/h17-18,20H,2-16,19H2,1H3,(H2,21,22,23)/t17-,18+/m0/s1
InChI Key:
YHEDRJPUIRMZMP-ZWKOTPCHSA-N
SMILES:
CCCCCCCCCCCCCCCC(C(COP(=O)(O)O)N)O
Properties
Complexity:
337
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
2
Defined Bond Stereocenter Count:
0
Exact Mass:
381.264g/mol
Formal Charge:
0
Heavy Atom Count:
25
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
381.494g/mol
Monoisotopic Mass:
381.264g/mol
Rotatable Bond Count:
18
Topological Polar Surface Area:
113A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.4
Literature
| Title | Journal |
|---|---|
| A strategy for enrichment of the bioactive sphingoid base-1-phosphates produced by Hypericum perforatum L. in a balloon type airlift reactor. | Bioresource technology 20121101 |
| Myocardial infarction differentially alters sphingolipid levels in plasma, erythrocytes and platelets of the rat. | Basic research in cardiology 20121101 |
| Increased sphingoid base-1-phosphates and failure of neural tube closure after exposure to fumonisin or FTY720. | Birth defects research. Part A, Clinical and molecular teratology 20121001 |
| Inhibition of serine palmitoyltransferase delays the onset of radiation-induced pulmonary fibrosis through the negative regulation of sphingosine kinase-1 expression. | Journal of lipid research 20120801 |
| Distinct generation, pharmacology, and distribution of sphingosine 1-phosphate and dihydrosphingosine 1-phosphate in human neural progenitor cells. | Neuropharmacology 20120201 |
| Exercise increases plasma levels of sphingoid base-1 phosphates in humans. | Acta physiologica (Oxford, England) 20111101 |
| Targeted analysis of sphingoid precursors in human biofluids by solid-phase extraction with in situ derivatization prior to μ-LC-LIF determination. | Analytical and bioanalytical chemistry 20110501 |
| 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 |
| UPLC-MS/MS method for analysis of sphingosine 1-phosphate in biological samples. | Prostaglandins & other lipid mediators 20100901 |
| Sphinganine-1-phosphate protects kidney and liver after hepatic ischemia and reperfusion in mice through S1P1 receptor activation. | Laboratory investigation; a journal of technical methods and pathology 20100801 |
| Dihydrosphingosine 1-phosphate has a potent antifibrotic effect in scleroderma fibroblasts via normalization of phosphatase and tensin homolog levels. | Arthritis and rheumatism 20100701 |
| Plasma sphingosine-1-phosphate concentration is reduced in patients with myocardial infarction. | Medical science monitor : international medical journal of experimental and clinical research 20090901 |
| High-throughput analysis of sphingosine 1-phosphate, sphinganine 1-phosphate, and lysophosphatidic acid in plasma samples by liquid chromatography-tandem mass spectrometry. | Clinical chemistry 20090601 |
| FTY720 inhibits ceramide synthases and up-regulates dihydrosphingosine 1-phosphate formation in human lung endothelial cells. | The Journal of biological chemistry 20090227 |
| Sphingosine 1-phosphate modulates spinal nociceptive processing. | The Journal of biological chemistry 20081121 |
| Human cytomegalovirus regulates bioactive sphingolipids. | The Journal of biological chemistry 20080919 |
| Opposite effects of dihydrosphingosine 1-phosphate and sphingosine 1-phosphate on transforming growth factor-beta/Smad signaling are mediated through the PTEN/PPM1A-dependent pathway. | The Journal of biological chemistry 20080711 |
| Prostacyclin induction by high-density lipoprotein (HDL) in vascular smooth muscle cells depends on sphingosine 1-phosphate receptors: effect of simvastatin. | Thrombosis and haemostasis 20080701 |
| Involvement of sphingoid bases in mediating reactive oxygen intermediate production and programmed cell death in Arabidopsis. | Cell research 20071201 |
| Validation of fumonisin biomarkers in F344 rats. | Toxicology and applied pharmacology 20071115 |
| Elevation of sphingoid base 1-phosphate as a potential contributor to hepatotoxicity in fumonisin B1-exposed mice. | Archives of pharmacal research 20070801 |
| Sphingosine-1-phosphate and calcium signaling in cerebellar astrocytes and differentiated granule cells. | Neurochemical research 20070101 |
| Distribution and dynamic changes of sphingolipids in blood in response to platelet activation. | Journal of thrombosis and haemostasis : JTH 20061201 |
| Elevation of sphinganine 1-phosphate as a predictive biomarker for fumonisin exposure and toxicity in mice. | Journal of toxicology and environmental health. Part A 20061201 |
| LC-MS/MS-analysis of sphingosine-1-phosphate and related compounds in plasma samples. | Prostaglandins & other lipid mediators 20061201 |
| De novo biosynthesis of dihydrosphingosine-1-phosphate by sphingosine kinase 1 in mammalian cells. | Cellular signalling 20061001 |
| Characterization and direct quantitation of sphingoid base-1-phosphates from lipid extracts: a shotgun lipidomics approach. | Journal of lipid research 20060801 |
| Effects of fumonisins on liver and kidney sphinganine and the sphinganine to sphingosine ratio during chronic exposure in ducks. | Chemico-biological interactions 20060310 |
| Dihydrosphingosine 1-phosphate stimulates MMP1 gene expression via activation of ERK1/2-Ets1 pathway in human fibroblasts. | FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20060101 |
| Novel role of sphingosine kinase 1 as a mediator of neurotrophin-3 action in oligodendrocyte progenitors. | Journal of neurochemistry 20051201 |
| Sphingosine 1-phosphate analogue recognition and selectivity at S1P4 within the endothelial differentiation gene family of receptors. | The Biochemical journal 20050701 |
| Quantitative analysis of sphingoid base-1-phosphates as bisacetylated derivatives by liquid chromatography-tandem mass spectrometry. | Analytical biochemistry 20050401 |
| Pharmacological characterization of human S1P4 using a novel radioligand, [4,5-3H]-dihydrosphingosine-1-phosphate. | British journal of pharmacology 20040701 |
| Sphingosine-1-phosphate inhibits C-type natriuretic peptide activation of guanylyl cyclase B (GC-B/NPR-B). | Hypertension (Dallas, Tex. : 1979) 20040501 |
| Comparative analysis of functional assays for characterization of agonist ligands at G protein-coupled receptors. | Journal of biomolecular screening 20031001 |
| Role of human sphingosine-1-phosphate phosphatase 1 in the regulation of intra- and extracellular sphingosine-1-phosphate levels and cell viability. | The Journal of biological chemistry 20030905 |
| Ligand-dependent inhibition of B16 melanoma cell migration and invasion via endogenous S1P2 G protein-coupled receptor. Requirement of inhibition of cellular RAC activity. | The Journal of biological chemistry 20030829 |
| Metabolomic profiling of sphingolipids in human glioma cell lines by liquid chromatography tandem mass spectrometry. | Cellular and molecular biology (Noisy-le-Grand, France) 20030701 |
| Transmembrane topology of sphingoid long-chain base-1-phosphate phosphatase, Lcb3p. | Genes to cells : devoted to molecular & cellular mechanisms 20030601 |
| Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63. | Cellular signalling 20030401 |
| Syntheses of sphingosine-1-phosphate stereoisomers and analogues and their interaction with EDG receptors. | Bioorganic & medicinal chemistry letters 20030120 |
| Signalling mechanisms in sphingosine 1-phosphate-promoted mesangial cell proliferation. | Genes to cells : devoted to molecular & cellular mechanisms 20021201 |
| Sphingosine 1-phosphate is a ligand of the human gpr3, gpr6 and gpr12 family of constitutively active G protein-coupled receptors. | Cellular signalling 20021101 |
| Phytosphingosine 1-phosphate: a high affinity ligand for the S1P(4)/Edg-6 receptor. | Biochemical and biophysical research communications 20020927 |
| Sphingosine 1-phosphate, present in serum-derived lipoproteins, activates matriptase. | The Journal of biological chemistry 20020322 |
| [Biologically effective sphingolipids devoid of 4-trans-double bond in the sphingoid hydrocarbon chain]. | Bioorganicheskaia khimiia 20020101 |
| 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 |
| Characterization of a novel sphingosine 1-phosphate receptor, Edg-8. | The Journal of biological chemistry 20000512 |
| Sphingosine-1-phosphate is a ligand for the G protein-coupled receptor EDG-6. | Blood 20000415 |
| Differential pharmacological properties and signal transduction of the sphingosine 1-phosphate receptors EDG-1, EDG-3, and EDG-5. | The Journal of biological chemistry 19990702 |
| EDG1 is a functional sphingosine-1-phosphate receptor that is linked via a Gi/o to multiple signaling pathways, including phospholipase C activation, Ca2+ mobilization, Ras-mitogen-activated protein kinase activation, and adenylate cyclase inhibition. | The Journal of biological chemistry 19981016 |
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