GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

synaptamide   Click here for help

GtoPdb Ligand ID: 14141

Synonyms: N-docosahexaenoylethanolamine
Compound class: Synthetic organic
Comment: Synaptamide is an endocannabinoid-like derivative of docosahexaenoic acid (DHA) that is biosynthesised in the brain. It has cannabinoid-independent activities.

synaptamide is commercially available from our sponsors

2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 17
Topological polar surface area 49.33
Molecular weight 371.56
XLogP 7.91
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
Click here for help

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/)

✖
Canonical SMILES CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCO
Isomeric SMILES CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCO
InChI InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChI Key GEEHOLRSGZPBSM-KUBAVDMBSA-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/)

For advanced searching click here to open chemical structure editor

Similar Ligands Click here for help
N-docosatetra-7,10,13,16-enoylethanolamine
Click here for ligand page
N-homo-γ-linolenoylethanolamine
Click here for ligand page
MEA
Click here for ligand page
Targets
N-Acylethanolamine acid amidase
N-arachidonoylglycine
Click here for ligand page
Targets
GPR18; LPA5 receptor
N-palmitoylethanolamine
Click here for ligand page
Targets
GPR119; GPR55; N-Acylethanolamine acid amidase; Fatty acid amide hydrolase; Fatty acid amide hydrolase-2
SEA
Click here for ligand page
Targets
GPR119; N-Acylethanolamine acid amidase
N-oleoylethanolamide
Click here for ligand page
Targets
GPR119; GPR55; N-Acylethanolamine acid amidase; Fatty acid amide hydrolase; Fatty acid amide hydrolase-2; Peroxisome proliferator-activated receptor-α
anandamide
Click here for ligand page
Targets
GPR119; GPR18; GPR55; CB1 receptor; CB2 receptor; Cav3.2; Cav3.3; Glycine Receptor (All subtypes); Kv1.2; K2P3.1; K2P9.1; TRPM8; TRPV1; glycine receptor α1 subunit; monoacylglycerol lipase... click on ligand to see complete list
arachidonyl-2-chloroethylamide
Click here for ligand page
Targets
CB1 receptor