sphingosine   Click here for help

GtoPdb Ligand ID: 2452

Synonyms: cerebroside | D-erythrosphingosine | D-sphingosine
PDB Ligand
Compound class: Metabolite
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 3
Rotatable bonds 15
Topological polar surface area 66.48
Molecular weight 299.28
XLogP 6.02
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES CCCCCCCCCCCCCC=CC(C(CO)N)O
Isomeric SMILES CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO)N)O
InChI InChI=1S/C18H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)17(19)16-20/h14-15,17-18,20-21H,2-13,16,19H2,1H3/b15-14+/t17-,18+/m0/s1
InChI Key WWUZIQQURGPMPG-KRWOKUGFSA-N
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
ceramide synthase 6
alkaline ceramidase 1
ceramide synthase 3
Mitochondrial 5'-nucleotidase
sphingosine-1-phosphate phosphatase 1
ceramide synthase 2
sphingosine-1-phosphate phosphatase 2
ceramide synthase 4
sphingosine kinase 2
ceramide synthase 5
sphingosine kinase 1
N-acylsphingosine amidohydrolase 1
ceramide synthase 1
alkaline ceramidase 2
N-acylsphingosine amidohydrolase 2
5'(3')-nucleotidase
Selectivity at ion channels
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TRPM3 Ligand is endogenous in the given species Hs Activator Agonist 4.9 pEC50 - 1
pEC50 4.9 (EC50 1.259x10-5 M) [1]
Voltage: Physiological
TRPM7 Mm Channel blocker Inhibition 6.2 pIC50 - 2
pIC50 6.2 (IC50 5.9x10-7 M) [2]
Voltage: -100.0 – 100.0 mV