sphingosine 1-phosphate   Click here for help

GtoPdb Ligand ID: 911

Abbreviated name: S1P
PDB Ligand
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
Natural/Endogenous Targets
Target
GPR12
GPR3
GPR63
GPR6
P2RY10
S1P1 receptor
S1P2 receptor
S1P3 receptor
S1P4 receptor
S1P5 receptor
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
5'(3')-nucleotidase
sphingosine kinase 1
sphingosine kinase 2
sphingosine-1-phosphate phosphatase 1
Mitochondrial 5'-nucleotidase
sphingosine-1-phosphate phosphatase 2
sphingosine-1-phosphate lyase 1
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
S1P5 receptor Ligand is endogenous in the given species Rn Agonist Agonist 8.7 pKd - 10
pKd 8.7 [10]
S1P1 receptor Hs Agonist Agonist 7.9 – 9.4 pKd - 5,12
pKd 7.9 – 9.4 (Kd 1.32x10-8 – 3.9x10-10 M) [5,12]
S1P3 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.6 – 9.6 pKd - 5,12,27
pKd 7.6 – 9.6 (Kd 2.62x10-8 – 2.3x10-10 M) [5,12,27]
S1P2 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.6 – 7.7 pKd - 12,27
pKd 7.6 – 7.7 (Kd 2.7x10-8 – 2.04x10-8 M) [12,27]
S1P3 receptor Ligand is endogenous in the given species Hs Agonist Agonist 8.4 – 9.8 pEC50 - 3,9,19
pEC50 8.4 – 9.8 [3,9,19]
S1P1 receptor Mm Agonist Agonist 8.9 pEC50 - 19,21
pEC50 8.9 (EC50 1.4x10-9 M) [19,21]
S1P2 receptor Ligand is endogenous in the given species Mm Agonist Agonist 8.7 pEC50 - 21
pEC50 8.7 (EC50 2x10-9 M) [21]
S1P3 receptor Ligand is endogenous in the given species Mm Agonist Agonist 8.6 pEC50 - 21
pEC50 8.6 (EC50 2.3x10-9 M) [21]
S1P1 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.1 – 9.5 pEC50 - 3,9,17,19,21-22
pEC50 9.5 (EC50 2.9x10-10 M) [22]
pEC50 7.1 – 9.4 (EC50 7.94x10-8 – 4x10-10 M) [3,9,17,19,21]
S1P2 receptor Ligand is endogenous in the given species Hs Agonist Agonist 8.1 – 8.5 pEC50 - 9,19
pEC50 8.1 – 8.5 [9,19]
S1P5 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.4 – 8.9 pEC50 - 3,9,19,21
pEC50 7.4 – 8.9 [3,9,19,21]
S1P5 receptor Ligand is endogenous in the given species Mm Agonist Agonist 7.8 – 7.9 pEC50 - 9,21
pEC50 7.8 – 7.9 (EC50 1.6x10-8 M) [9,21]
S1P4 receptor Ligand is endogenous in the given species Hs Agonist Agonist 7.2 – 8.1 pEC50 - 4,19,21
pEC50 7.2 – 8.1 (EC50 6.7x10-8 M) [4,19,21]
GPR6 Ligand is endogenous in the given species Mm Agonist Full agonist 7.3 – 7.7 pEC50 - 8,25
pEC50 7.3 – 7.7 (EC50 5.6x10-8 – 2.2x10-8 M) [8,25]
GPR3 Ligand is endogenous in the given species Hs Agonist Full agonist 7.1 – 7.7 pEC50 - 25
pEC50 7.1 – 7.7 [25]
P2RY10 Ligand is endogenous in the given species Hs Agonist Agonist 7.3 pEC50 - 15
pEC50 7.3 [15]
S1P4 receptor Ligand is endogenous in the given species Mm Agonist Agonist 7.1 pEC50 - 21
pEC50 7.1 (EC50 7.5x10-8 M) [21]
GPR12 Ligand is endogenous in the given species Hs Agonist Full agonist 5.5 – 7.0 pEC50 - 25
pEC50 5.5 – 7.0 (EC50 3.1x10-6 – 1.2x10-6 M) [25]
GPR63 Ligand is endogenous in the given species Hs Agonist Full agonist 6.1 – 6.2 pEC50 - 16
pEC50 6.1 – 6.2 (EC50 8x10-7 – 6.6x10-7 M) [16]
S1P4 receptor Ligand is endogenous in the given species Hs Agonist Agonist 6.1 – 7.0 pIC50 - 3-4
pIC50 6.1 – 7.0 [3-4]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
Targets where the ligand is described in the comment field
Target Comment
Ligand mentioned in the following text fields