Home Other Building Blocks racFTY720 Phosphate

racFTY720 Phosphate

CAS No.:
402615-91-2
Catalog Number:
AG00C0WH
Molecular Formula:
C19H34NO5P
Molecular Weight:
387.4507
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Product Description
Catalog Number:
AG00C0WH
Chemical Name:
racFTY720 Phosphate
CAS Number:
402615-91-2
Molecular Formula:
C19H34NO5P
Molecular Weight:
387.4507
MDL Number:
MFCD18251416
IUPAC Name:
[2-amino-2-(hydroxymethyl)-4-(4-octylphenyl)butyl] dihydrogen phosphate
InChI:
InChI=1S/C19H34NO5P/c1-2-3-4-5-6-7-8-17-9-11-18(12-10-17)13-14-19(20,15-21)16-25-26(22,23)24/h9-12,21H,2-8,13-16,20H2,1H3,(H2,22,23,24)
InChI Key:
LRFKWQGGENFBFO-UHFFFAOYSA-N
SMILES:
CCCCCCCCc1ccc(cc1)CCC(COP(=O)(O)[O-])(CO)[NH3+]
Properties
Complexity:
409  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
387.217g/mol
Formal Charge:
0
Heavy Atom Count:
26  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
387.457g/mol
Monoisotopic Mass:
387.217g/mol
Rotatable Bond Count:
14  
Topological Polar Surface Area:
113A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
0.8  
Literature
Title Journal
Elevated Nuclear and Cytoplasmic FTY720-Phosphate in Mouse Embryonic Fibroblasts Suggests the Potential for Multiple Mechanisms in FTY720-Induced Neural Tube Defects. Toxicological sciences : an official journal of the Society of Toxicology 20160301
Discovery of A-971432, An Orally Bioavailable Selective Sphingosine-1-Phosphate Receptor 5 (S1P5) Agonist for the Potential Treatment of Neurodegenerative Disorders. Journal of medicinal chemistry 20151210
FTY720 Phosphate Activates Sphingosine-1-Phosphate Receptor 2 and Selectively Couples to Gα12/13/Rho/ROCK to Induce Myofibroblast Contraction. Molecular pharmacology 20150601
ASP4058, a novel agonist for sphingosine 1-phosphate receptors 1 and 5, ameliorates rodent experimental autoimmune encephalomyelitis with a favorable safety profile. PloS one 20140101
Sphingosine and FTY720 are potent inhibitors of the transient receptor potential melastatin 7 (TRPM7) channels. British journal of pharmacology 20130301
The sphingosine-1-phosphate receptor agonist FTY720 and its phosphorylated form affect the function of CD4+CD25+ T cells in vitro. International journal of molecular medicine 20120701
LC-MS/MS determination of FTY720 and FTY720-phosphate in murine intracellular compartments and human plasma. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20120301
Fast simultaneous quantitative analysis of FTY720 and its metabolite FTY720-P in human blood by on-line solid phase extraction coupled with liquid chromatography-tandem mass spectrometry. Journal of pharmaceutical and biomedical analysis 20120125
Kinetic analysis of autotaxin reveals substrate-specific catalytic pathways and a mechanism for lysophosphatidic acid distribution. The Journal of biological chemistry 20110826
Engagement of S1P₁-degradative mechanisms leads to vascular leak in mice. The Journal of clinical investigation 20110601
Plasma gelsolin modulates cellular response to sphingosine 1-phosphate. American journal of physiology. Cell physiology 20101201
(S)-FTY720-vinylphosphonate, an analogue of the immunosuppressive agent FTY720, is a pan-antagonist of sphingosine 1-phosphate GPCR signaling and inhibits autotaxin activity. Cellular signalling 20101001
Removal of sphingosine 1-phosphate receptor-3 (S1P(3)) agonism is essential, but inadequate to obtain immunomodulating 2-aminopropane-1,3-diol S1P(1) agonists with reduced effect on heart rate. Journal of medicinal chemistry 20100422
Phosphorylation of the immunomodulator FTY720 inhibits programmed cell death of fibroblasts via the S1P3 receptor subtype and Bcl-2 activation. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology 20100101
Utilization of the Tango beta-arrestin recruitment technology for cell-based EDG receptor assay development and interrogation. Journal of biomolecular screening 20091001
Different response patterns of several ligands at the sphingosine-1-phosphate receptor subtype 3 (S1P(3)). British journal of pharmacology 20090401
Accumulation of fingolimod (FTY720) in lymphoid tissues contributes to prolonged efficacy. The Journal of pharmacology and experimental therapeutics 20090301
Sphingosine 1-phosphate receptor agonism impairs skin dendritic cell migration and homing to secondary lymphoid tissue: association with prolonged allograft survival. Transplant immunology 20081101
Anticancer activity of FTY720: phosphorylated FTY720 inhibits autotaxin, a metastasis-enhancing and angiogenic lysophospholipase D. Cancer letters 20080808
Selective activation of G alpha i mediated signalling of S1P3 by FTY720-phosphate. Cellular signalling 20080601
A novel sphingosine 1-phosphate receptor agonist, 2-amino-2-propanediol hydrochloride (KRP-203), regulates chronic colitis in interleukin-10 gene-deficient mice. The Journal of pharmacology and experimental therapeutics 20080101
Functional consequences of S1P receptor modulation in rat oligodendroglial lineage cells. Glia 20071201
Neither intravenous nor intracerebroventricular administration of obestatin affects the secretion of GH, PRL, TSH and ACTH in rats. Regulatory peptides 20070201
Synthesis and biological evaluation of gamma-aminophosphonates as potent, subtype-selective sphingosine 1-phosphate receptor agonists and antagonists. Bioorganic & medicinal chemistry 20070115
A monoselective sphingosine-1-phosphate receptor-1 agonist prevents allograft rejection in a stringent rat heart transplantation model. Chemistry & biology 20061101
Novel immunomodulator FTY720 is phosphorylated in rats and humans to form a single stereoisomer. Identification, chemical proof, and biological characterization of the biologically active species and its enantiomer. Journal of medicinal chemistry 20050811
Synthesis of 4(5)-phenylimidazole-based analogues of sphingosine-1-phosphate and FTY720: discovery of potent S1P1 receptor agonists. Bioorganic & medicinal chemistry letters 20050801
A rational utilization of high-throughput screening affords selective, orally bioavailable 1-benzyl-3-carboxyazetidine sphingosine-1-phosphate-1 receptor agonists. Journal of medicinal chemistry 20041230
Potent S1P receptor agonists replicate the pharmacologic actions of the novel immune modulator FTY720. Bioorganic & medicinal chemistry letters 20040621
Immune cell regulation and cardiovascular effects of sphingosine 1-phosphate receptor agonists in rodents are mediated via distinct receptor subtypes. The Journal of pharmacology and experimental therapeutics 20040501
Sphingosine 1-phosphate (S1P) receptor subtypes S1P1 and S1P3, respectively, regulate lymphocyte recirculation and heart rate. The Journal of biological chemistry 20040402
The immune modulator FTY720 targets sphingosine 1-phosphate receptors. The Journal of biological chemistry 20020614
Alteration of lymphocyte trafficking by sphingosine-1-phosphate receptor agonists. Science (New York, N.Y.) 20020412
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