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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.
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 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
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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 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/)
Selectivity at GPCRs
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
ADGRF1 Ligand is endogenous in the given species Hs Agonist Agonist - - - 5
⤷ [5]
Targets where the ligand is described in the comment field
Target Comment
ADGRF1 Coupling with all major G protein families is reported [4], including Gs and Gq [3,12], and Gαs and Gαq/11 [15]. N-Docosahexaenoylethanolamine (synaptamide) is an agonist at ADGRF1 supporting neurogenesis [6]. The cryo-EM structure of the 7-helix transmembrane domain with its intramolecular agonist has been determined [10,15]. Furthermore, the domain structure of the N terminus (SEA, HormR, GAIN) has been solved by X-ray crystallography [13]. The structural basis for G protein-coupling has also been reported [4]. Expressed in kidney and prostate [8,11], spleen, liver, and adrenal gland [9]. ADGRF1 may be a prognositic marker for uterine corpus endometrial cancer [7]. Tumour-promoting function in HER2-positive breast cancer has been reported [1-2], as has a role in non-alcoholic fatty liver disease progression [14].