Structure Database (LMSD)
Common Name
Sphingosine-1-phosphate
Systematic Name
Sphing-4-enine-1-phosphate
Synonyms
LM ID
LMSP01050001
Formula
Exact Mass
Calculate m/z
379.248762
Sum Composition
Status
Curated
3D model of Sphingosine-1-phosphate
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Biological Context
Sphingosine-1-phosphate (S1P) is the product of phosphorylation of sphingosine by sphingosine kinase that is secreted from cells and acts as an agonist at S1P receptors.1,2 It increases intracellular calcium levels in TAg-Jurkat cells expressing S1P1 and Gqi5, which allows for phospholipase C stimulation by Gi proteins, when used at a concentration of 200 nM, as well as in TAg-Jurkat cells expressing S1P2 and S1P3 receptors (EC50s = 8 and 11 nM, respectively).3 Intra- and extracellular levels of S1P vary spatially allowing it to function as an autocrine or paracrine factor, respectively, and dysregulation of S1P levels are associated with various disease states, such as inflammation and autoimmunity.4 S1P has a wide variety of effects, including an involvement in cell growth, angiogenesis, immunity, and neuroprotection.
This information has been provided by Cayman Chemical
References
1. van Koppen, C.J., zu Heringdorf, D.M., Laser, K.T., et al. Activation of a high affinity Gi protein-coupled plasma membrane receptor by sphingosine-1-phosphate. The Journal of Biological Chemisty 271(4), 2082-2087 (1996).
3. An, S., Bleu, T., and Zheng, Y. Transduction of intracellular calcium signals through G protein-mediated activation of phospholipase C by recombinant sphingosine 1-phosphate receptors. Mol. Pharmacol. 55(5), 787-794 (1999).
4. Cartier, A., and Hla, T. Sphingosine 1-phosphate: Lipid signaling in pathology and therapy. Science 366(6463), (2019).
Reactions
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References
Taxonomy Information
Curated from
NCBI taxonomy class
Reference
Homo sapiens
(#9606)
Mammalia
(#40674)
Lipidomics reveals a remarkable diversity of lipids in human plasma,
J Lipid Res, 2010
J Lipid Res, 2010
Pubmed ID:
20671299
DOI:
10.1194/jlr.M009449
String Representations
InChiKey (Click to copy)
DUYSYHSSBDVJSM-KRWOKUGFSA-N
InChi (Click to copy)
InChI=1S/C18H38NO5P/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/h14-15,17-18,20H,2-13,16,19H2,1H3,(H2,21,22,23)/b15-14+/t17-,18+/m0/s1
SMILES (Click to copy)
OP(OC[C@]([H])(N)[C@]([H])(O)/C=C/CCCCCCCCCCCCC)(=O)O
Other Databases
Wikipedia
KEGG ID
HMDB ID
CHEBI ID
PubChem CID
SwissLipids ID
Cayman ID
PDB ID
GuidePharm ID
Calculated Physicochemical Properties
Heavy Atoms
25
Rings
0
Aromatic Rings
0
Rotatable Bonds
17
Van der Waals Molecular Volume
392.10
Topological Polar Surface Area
113.01
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
5
logP
5.24
Molar Refractivity
103.44
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Updated at
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