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



Classification

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
Pubmed ID: 20671299

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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