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
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).
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
SMILES / InChI / InChIKey
Click here for help
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
No information available.
Summary of Clinical Use Click here for help
This compound has been granted orphan drug designation by the FDA (2014) for the treatment of retinitis pigmentosa. High dose DHA supplementation has been assessed in a Phase II clinical trial in patients with X-linked retinitis pigmentosa. Results reported in [3] indicate that this treament did not slow retinal degeneration, although a longer and larger trial was suggested in order to increase the power of the study to identify significant differences between control and treatment groups.