dihydrosphingosine 1-phosphate   Click here for help

GtoPdb Ligand ID: 2921

Synonyms: dihydroS1P | sphinganine 1-phosphate | sphinganine-phosphate
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 18
Topological polar surface area 122.82
Molecular weight 381.26
XLogP 5.04
No. Lipinski's rules broken 2
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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
1. Ancellin N, Hla T. (1999)
Differential pharmacological properties and signal transduction of the sphingosine 1-phosphate receptors EDG-1, EDG-3, and EDG-5.
J Biol Chem, 274 (27): 18997-9002. [PMID:10383399]
2. Candelore MR, Wright MJ, Tota LM, Milligan J, Shei GJ, Bergstrom JD, Mandala SM. (2002)
Phytosphingosine 1-phosphate: a high affinity ligand for the S1P(4)/Edg-6 receptor.
Biochem Biophys Res Commun, 297 (3): 600-6. [PMID:12270137]
3. Im DS, Heise CE, Ancellin N, O'Dowd BF, Shei GJ, Heavens RP, Rigby MR, Hla T, Mandala S, McAllister G et al.. (2000)
Characterization of a novel sphingosine 1-phosphate receptor, Edg-8.
J Biol Chem, 275 (19): 14281-6. [PMID:10799507]
4. Niedernberg A, Tunaru S, Blaukat A, Ardati A, Kostenis E. (2003)
Sphingosine 1-phosphate and dioleoylphosphatidic acid are low affinity agonists for the orphan receptor GPR63.
Cell Signal, 15 (4): 435-46. [PMID:12618218]
5. Okamoto H, Takuwa N, Gonda K, Okazaki H, Chang K, Yatomi Y, Shigematsu H, Takuwa Y. (1998)
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.
J Biol Chem, 273 (42): 27104-10. [PMID:9765227]
6. Van Brocklyn JR, Gräler MH, Bernhardt G, Hobson JP, Lipp M, Spiegel S. (2000)
Sphingosine-1-phosphate is a ligand for the G protein-coupled receptor EDG-6.
Blood, 95 (8): 2624-9. [PMID:10753843]