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docosahexaenoic acid   Click here for help

GtoPdb Ligand ID: 1051

Abbreviated name: DHA
Synonyms: all-cis-DHA | all-cis-docosa-4,7,10,13,16,19-hexaenoic acid | doconexent | Omega 3 fatty acid | Omega-3 marine triglycerides | Retriacyl® (proposed trade name)
PDB Ligand
Compound class: Metabolite
Comment: Docosahexaenoic acid is an endogenous omega-3 fatty acid, activating all 3 retinoid X receptor isoforms. It has no activity at retinoic acid receptors (RARs), the thyroid hormone receptor or the vitamin D receptor (VDR).
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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

docosahexaenoic acid is commercially available from our sponsors

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 2
Hydrogen bond donors 1
Rotatable bonds 14
Topological polar surface area 37.3
Molecular weight 328.24
XLogP 8.83
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 CCC=CCC=CCC=CCC=CCC=CCC=CCCC(=O)O
Isomeric SMILES CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)O
InChI InChI=1S/C22H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22(23)24/h3-4,6-7,9-10,12-13,15-16,18-19H,2,5,8,11,14,17,20-21H2,1H3,(H,23,24)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-
InChI Key MBMBGCFOFBJSGT-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/)
Classification Click here for help
Compound class Metabolite
IUPAC Name Click here for help
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
International Nonproprietary Names Click here for help
INN number INN
6428 doconexent
Synonyms Click here for help
all-cis-DHA | all-cis-docosa-4,7,10,13,16,19-hexaenoic acid | doconexent | Omega 3 fatty acid | Omega-3 marine triglycerides | Retriacyl® (proposed trade name)
Database Links Click here for help
Specialist databases
GPCRdb Ligand docosahexaenoic acid
Other databases
CAS Registry No. 6217-54-5 (source: Scifinder)
ChEBI CHEBI:28125
ChEMBL Ligand CHEMBL367149
DrugCentral Ligand 4289
GtoPdb PubChem SID 135651477
LIPID MAPS LMFA01030185
PubChem CID 445580
RCSB PDB Ligand HXA
Search Google for chemical match using the InChIKey MBMBGCFOFBJSGT-KUBAVDMBSA-N
Search Google for chemicals with the same backbone MBMBGCFOFBJSGT
Search PubMed clinical trials doconexent
Search PubMed titles doconexent
Search PubMed titles/abstracts doconexent
UniChem Compound Search for chemical match using the InChIKey MBMBGCFOFBJSGT-KUBAVDMBSA-N
UniChem Connectivity Search for chemical match using the InChIKey MBMBGCFOFBJSGT-KUBAVDMBSA-N
Wikipedia Docosahexaenoic_acid

Product suppliers

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Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

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MedChemExpress
Docosahexaenoic acid (links to external site)
Cat. No. HY-B2167
(Same CID)