sphingosine 1-phosphate   Click here for help

GtoPdb Ligand ID: 911

Abbreviated name: S1P
PDB Ligand
Compound class: Metabolite
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.
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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 17
Topological polar surface area 122.82
Molecular weight 379.25
XLogP 4.79
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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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
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InChI standard key Download

Molecular structure representations generated using Open Babel