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).
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2D Structure
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Physico-chemical Properties
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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
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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-
1. Briscoe CP, Tadayyon M, Andrews JL, Benson WG, Chambers JK, Eilert MM, Ellis C, Elshourbagy NA, Goetz AS, Minnick DT et al.. (2003)
The orphan G protein-coupled receptor GPR40 is activated by medium and long chain fatty acids.
J Biol Chem, 278 (13): 11303-11. [PMID:12496284]
2. Desvergne B, Wahli W. (1999)
Peroxisome proliferator-activated receptors: nuclear control of metabolism.
Endocr Rev, 20 (5): 649-88. [PMID:10529898]
3. Hoffman DR, Hughbanks-Wheaton DK, Pearson NS, Fish GE, Spencer R, Takacs A, Klein M, Locke KG, Birch DG. (2014)
Four-year placebo-controlled trial of docosahexaenoic acid in X-linked retinitis pigmentosa (DHAX trial): a randomized clinical trial.
JAMA Ophthalmol, 132 (7): 866-73. [PMID:24805262]
4. Hossain S, Hashimoto M, Katakura M, Miwa K, Shimada T, Shido O. (2009)
Mechanism of docosahexaenoic acid-induced inhibition of in vitro Abeta1-42 fibrillation and Abeta1-42-induced toxicity in SH-S5Y5 cells.
J Neurochem, 111 (2): 568-79. [PMID:19686246]
5. Itoh Y, Kawamata Y, Harada M, Kobayashi M, Fujii R, Fukusumi S, Ogi K, Hosoya M, Tanaka Y, Uejima H et al.. (2003)
Free fatty acids regulate insulin secretion from pancreatic beta cells through GPR40.
Nature, 422 (6928): 173-6. [PMID:12629551]
6. Lampen A, Meyer S, Nau H. (2001)
Phytanic acid and docosahexaenoic acid increase the metabolism of all-trans-retinoic acid and CYP26 gene expression in intestinal cells.
Biochim Biophys Acta, 1521 (1-3): 97-106. [PMID:11690641]
7. Lesage F, Terrenoire C, Romey G, Lazdunski M. (2000)
Human TREK2, a 2P domain mechano-sensitive K+ channel with multiple regulations by polyunsaturated fatty acids, lysophospholipids, and Gs, Gi, and Gq protein-coupled receptors.
J Biol Chem, 275 (37): 28398-405. [PMID:10880510]
8. Motter AL, Ahern GP. (2012)
TRPA1 is a polyunsaturated fatty acid sensor in mammals.
PLoS ONE, 7 (6): e38439. [PMID:22723860]