sphingosine 1-phosphate   

GtoPdb Ligand ID: 911

Abbreviated name: S1P
Comment: Sphingosine 1-phosphate (S1P) is a zwitterionic lyso-phospholipid product of the sphingosine biosynthetic pathway. It is a result of the phosphorylation of sphingosine by two well characterised kinases, SPHK1 and SPHK2 (sphingosine kinase 1 and 2). SPHK1 is predominately extracellular and SPHK1 intracellular. Sphingosine itself is produced by the N-deacylation of ceramide by the enzyme ceramidase.
2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 17
Topological polar surface area 122.82
Molecular weight 379.25
XLogP 4.79
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES CCCCCCCCCCCCCC=CC(C(COP(=O)(O)O)N)O
Isomeric SMILES CCCCCCCCCCCCC/C=C/[C@H]([C@H](COP(=O)(O)O)N)O
InChI 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
InChI Key DUYSYHSSBDVJSM-KRWOKUGFSA-N
Classification
Compound class Metabolite or derivative
IUPAC Name
[(2S,3R)-2-amino-3-hydroxyoctadec-4-enyl] dihydrogen phosphate
Database Links
BindingDB Ligand 50158348
CAS Registry No. 26993-30-6 (source: Scifinder)
ChEBI CHEBI:37550
ChEMBL Ligand CHEMBL225155
GtoPdb PubChem SID 135651563
PubChem CID 5283560
RCSB PDB Ligand S1P
Search Google for chemical match using the InChIKey DUYSYHSSBDVJSM-KRWOKUGFSA-N
Search Google for chemicals with the same backbone DUYSYHSSBDVJSM
Search UniChem for chemical match using the InChIKey DUYSYHSSBDVJSM-KRWOKUGFSA-N
Search UniChem for chemicals with the same backbone DUYSYHSSBDVJSM
Wikipedia Sphingosine-1-phosphate

Product suppliers

View disclaimer

Tocris
Sphingosine-1-phosphate
Cat. No. 1370