sphingosine   Click here for help

GtoPdb Ligand ID: 2452

Synonyms: cerebroside | D-erythrosphingosine | D-sphingosine
PDB Ligand
Compound class: Metabolite
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
ceramide synthase 6 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
alkaline ceramidase 1 3.5.1.23 ceramide -> sphingosine + a fatty acid
ceramide synthase 3 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
Mitochondrial 5'-nucleotidase 3.1.3.- Sphingosine 1-phosphate -> sphingosine + inorganic phosphate
dihydrosphingosine 1-phosphate -> dihydrosphingosine + inorganic phosphate
sphingosine-1-phosphate phosphatase 1 3.1.3.- Sphingosine 1-phosphate -> sphingosine + inorganic phosphate
dihydrosphingosine 1-phosphate -> dihydrosphingosine + inorganic phosphate
ceramide synthase 2 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
sphingosine-1-phosphate phosphatase 2 3.1.3.- Sphingosine 1-phosphate -> sphingosine + inorganic phosphate
dihydrosphingosine 1-phosphate -> dihydrosphingosine + inorganic phosphate
ceramide synthase 4 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
sphingosine kinase 2 2.7.1.91 Sphingosine + ATP = sphingosine 1-phosphate + ADP
dihydrosphingosine + ATP = dihydrosphingosine 1-phosphate + ADP
ceramide synthase 5 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
sphingosine kinase 1 2.7.1.91 Sphingosine + ATP = sphingosine 1-phosphate + ADP
dihydrosphingosine + ATP = dihydrosphingosine 1-phosphate + ADP
N-acylsphingosine amidohydrolase 1 3.5.1.23 ceramide -> sphingosine + a fatty acid
ceramide synthase 1 2.3.1.24 acylCoA + dihydrosphingosine -> dihydroceramide + coenzyme A
sphingosine + acylCoA -> ceramide + coenzyme A
alkaline ceramidase 2 3.5.1.23 ceramide -> sphingosine + a fatty acid
N-acylsphingosine amidohydrolase 2 3.5.1.23 ceramide -> sphingosine + a fatty acid
5'(3')-nucleotidase 3.1.3.- Sphingosine 1-phosphate -> sphingosine + inorganic phosphate
dihydrosphingosine 1-phosphate -> dihydrosphingosine + inorganic phosphate
Selectivity at ion channels
Key to terms and symbols Click column headers to sort
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