Identification

Name
Doconexent
Accession Number
DB03756
Description

A mixture of fish oil and primrose oil, doconexent is used as a high-docosahexaenoic acid (DHA) supplement. DHA is a 22 carbon chain with 6 cis double bonds with anti-inflammatory effects. It can be biosythesized from alpha-linolenic acid or commercially manufactured from microalgae. It is an omega-3 fatty acid and primary structural component of the human brain, cerebral cortex, skin, and retina thus plays an important role in their development and function. The amino-phospholipid DHA is found at a high concentration across several brain subcellular fractions, including nerve terminals, microsomes, synaptic vesicles, and synaptosomal plasma membranes 10.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 328.4883
Monoisotopic: 328.240230268
Chemical Formula
C22H32O2
Synonyms
  • (4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoic acid
  • 22:6-4, 7,10,13,16,19
  • 22:6(n-3)
  • 4,7,10,13,16,19-docosahexaenoic acid
  • all-cis-4,7,10,13,16,19-docosahexaenoic acid
  • all-cis-DHA
  • cervonic acid
  • DHA
  • Doconexent
  • docosa-4,7,10,13,16,19-hexaenoic acid
  • Docosahexaenoic acid

Pharmacology

Indication

Used as a high-docosahexaenoic acid (DHA) oral supplement.

Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

DHA in the central nervous system is found in the phospholipid bilayers where it modulates the physical environment and increase the free volume within the membrane bilayer. It influences the G-protein coupled receptor activity and affects transmembrane transport and cell interaction with the exterior world. It is also reported to promote apoptosis, neuronal differentiation and ion channel activity. Like other polyunsaturated fatty acids, DHA acts as a ligand at PPARs that plays an anti-inflammatory effect and regulate inflammatory gene expression and NFκB activation. DHA also gives rise to resolvins and related compounds (e.g., protectins) through pathways involving cyclooxygenase and lipoxygenase enzymes to resolve the inflammatory responses.

Mechanism of action

DHA and its conversion to other lipid signalling moleccules compete with the arachidonic acid cascade from endogenous phospholipids and shift the inflammatory state to being more anti-inflammatory. DHA inhibits endotoxin-stimulated production of IL-6 and IL-8 in human endothelial cells. Derivatives of DHA are anti-inflammatory lipid mediators. Lipid mediators resolvin D1 and protectin D1 all inhibit transendothelial migration of neutrophils, so preventing neutrophilic infiltration at sites of inflammation, resolvin D1 inhibits IL-1β production, and protectin D1 inhibits TNF and IL-1β production 1. Monoxydroxy derivative of DHA converted by LOX inhibit thromboxane-induced platelet aggregation. DHA supplementation has also shown to reduce the levels of serum C-reactive protein (CRP) and other circulating markers of inflammation such as neutrophils in hypertriglyceridemic men 12. DHA acts as a ligand at peroxisome proliferator-activated receptor (PPAR) gamma and alpha that regulate lipid signalling molecule-mediated transduction pathways and modulate inflammation. As a natural ligand, DHA induces a protective effect in retinal tissues by activating retinoid x receptors and subsequent ERK/MAPK signaling pathway in photoreceptors to promote their survival and differentiation, stimulating the expression of antiapoptotic proteins such as Bcl-2 and preserving mitochondrial membrane potential [A19453].

TargetActionsOrganism
APeroxisome proliferator-activated receptor alpha
ligand
Humans
APeroxisome proliferator-activated receptor gamma
ligand
Humans
ARetinoic acid receptor RXR-alpha
activator
Humans
ARetinoic acid receptor RXR-beta
activator
Humans
ARetinoic acid receptor RXR-gamma
activator
Humans
USterol regulatory element-binding protein 1
inhibitor
Humans
Absorption

Like other omega-3 fatty acids, DHA is hydrolyzed from the intestines and delivered through the lymphatic circulation. Plasma DHA concentrations increase in a dose-dependent and saturable manner.

Volume of distribution

DHA is the most abundant n−3 fatty acid in membranes and is present in all organs. It is also the most variable among organs and is particularly abundant in neural tissue, such as brain and retina, where it is several hundred-fold more abundant than EPA 13.

Protein binding
Not Available
Metabolism

DHA can be metabolized into DHA-derived specialized pro-resolving mediators (SPMs), DHA epoxides, electrophilic oxo-derivatives (EFOX) of DHA, neuroprostanes, ethanolamines, acylglycerols, docosahexaenoyl amides of amino acids or neurotransmitters, and branched DHA esters of hydroxy fatty acids, among others. It is converted to 17-hydroperoxy-DHA derivatives via COX-2 and 15-LOX and 5-LOX activity. These derivatives are further converted into D-series resolvins and protectins with potent anti-inflammatory potential and potent neuroprotective effect 3. DHA may also be metabolized to 19,20-epoxydocosapentaenoic acids (EDPs) and isomers via CYP2C9 activity. Epoxy metabolites are reported to mediate anti-tumor activity by inhibiting angiogenesis, tumor growth, and metastasis.

Hover over products below to view reaction partners

Route of elimination
Not Available
Half-life

Approximately 20 hours 9.

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity

Oral LD50 value in rats is 7,060 mg/kg and 3,450 mg/kg in mouse. Adverse effects include anemia, cough, CNS depression, drowsiness, headache, heart damage, lassitude (weakness, exhaustion), liver damage, narcosis, reproductive effects and teratogenic effects.

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbataceptThe metabolism of Doconexent can be increased when combined with Abatacept.
AbirateroneThe metabolism of Doconexent can be decreased when combined with Abiraterone.
AcenocoumarolThe metabolism of Acenocoumarol can be decreased when combined with Doconexent.
AcetohexamideThe metabolism of Acetohexamide can be decreased when combined with Doconexent.
Acetyl sulfisoxazoleThe metabolism of Doconexent can be decreased when combined with Acetyl sulfisoxazole.
Acetylsalicylic acidThe metabolism of Acetylsalicylic acid can be decreased when combined with Doconexent.
AdalimumabThe metabolism of Doconexent can be increased when combined with Adalimumab.
AgomelatineThe metabolism of Doconexent can be decreased when combined with Agomelatine.
AlosetronThe metabolism of Alosetron can be decreased when combined with Doconexent.
AlpelisibThe serum concentration of Doconexent can be decreased when it is combined with Alpelisib.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

    Learn more
  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
No interactions found.

Products

Product Ingredients
IngredientUNIICASInChI Key
Doconexent sodium295P7EPT4C81926-93-4SNNDEWVSGZRIFE-FPYKSTABSA-M
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
HerbalifelineDoconexent (78 mg) + Icosapent (119 mg)CapsuleOralHerbalife International Of Luxembourg S À R L2004-07-192009-07-21Canada
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Active OBDoconexent (320 mg/1) + Ascorbic acid (100 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric sulfate pentahydrate (2 mg/1) + Cyanocobalamin (30 ug/1) + D-alpha-Tocopherol acetate (30 [iU]/1) + Folic acid (1 mg/1) + Iron (20 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (2 mg/1) + Zinc oxide (30 mg/1)Capsule, liquid filledOralGm Pharmaceuticals2013-10-282017-03-31Us
Animi-3Doconexent (250 mg/1) + Cholecalciferol (1000 [iU]/1) + Cyanocobalamin (500 ug/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)CapsuleOralPbm Pharmaceuticals Inc.2011-06-01Not applicableUs
Animi-3 with Vitamin DDoconexent (250 mg/1) + Cholecalciferol (1000 [iU]/1) + Cyanocobalamin (500 ug/1) + Folic acid (1 mg/1) + Icosapent (35 mg/1) + Omega-3 fatty acids (500 mg/1) + Pyridoxine hydrochloride (12.5 mg/1) + Soy sterol (200 mg/1)CapsuleOralPbm Pharmaceuticals Inc.2011-06-01Not applicableUs
Cavan Folate DHADoconexent (250 mg/1) + Doconexent (250 mg/1) + Ascorbic acid (70 mg/1) + Ascorbic acid (70 mg/1) + Beta carotene (2700 [iU]/1) + Beta carotene (2700 [iU]/1) + Calcium carbonate (100 mg/1) + Calcium carbonate (100 mg/1) + Cholecalciferol (400 [iU]/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Cyanocobalamin (12 ug/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + Ferrous fumarate (65 mg/1) + Ferrous fumarate (65 mg/1) + Folic acid (1 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (25 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (18 mg/1) + Nicotinamide (18 mg/1) + Pyridoxine hydrochloride (2.5 mg/1) + Pyridoxine hydrochloride (2.5 mg/1) + Riboflavin (1.8 mg/1) + Riboflavin (1.8 mg/1) + Thiamine mononitrate (1.6 mg/1) + Thiamine mononitrate (1.6 mg/1) + Zinc oxide (25 mg/1) + Zinc oxide (25 mg/1)KitOralSeton Pharmaceuticals2010-06-042012-03-31Us
Cavan Folate DHADoconexent (250 mg/1) + Doconexent (250 mg/1) + Ascorbic acid (70 mg/1) + Ascorbic acid (70 mg/1) + Beta carotene (2700 [iU]/1) + Beta carotene (2700 [iU]/1) + Calcium carbonate (100 mg/1) + Calcium carbonate (100 mg/1) + Cholecalciferol (400 [iU]/1) + Cholecalciferol (400 [iU]/1) + Cupric oxide (2 mg/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Cyanocobalamin (12 ug/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + Ferrous fumarate (65 mg/1) + Ferrous fumarate (65 mg/1) + Folic acid (1 mg/1) + Folic acid (1 mg/1) + Magnesium oxide (25 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (18 mg/1) + Nicotinamide (18 mg/1) + Pyridoxine hydrochloride (2.5 mg/1) + Pyridoxine hydrochloride (2.5 mg/1) + Riboflavin (1.8 mg/1) + Riboflavin (1.8 mg/1) + Thiamine mononitrate (1.6 mg/1) + Thiamine mononitrate (1.6 mg/1) + Zinc oxide (25 mg/1) + Zinc oxide (25 mg/1)KitOralSeton Pharmaceuticals2010-06-042012-03-31Us
Cavan OneDoconexent (260 mg/1) + Calcium (150 mg/1) + Calcium ascorbate dihydrate (25 mg/1) + Cholecalciferol (170 [iU]/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + Ferrous asparto glycinate (7 mg/1) + Folic acid (1 mg/1) + Icosapent (40 mg/1) + Iron (20 mg/1) + Linoleic acid (30 mg/1) + Pyridoxine hydrochloride (25 mg/1) + alpha-Linolenic acid (30 mg/1)Capsule, gelatin coatedOralSeton Pharmaceuticals2009-10-302011-11-27Us
Choice OB DHADoconexent (250 mg/1) + Ascorbic acid (60 mg/1) + Beta carotene (1700 [iU]/1) + Cholecalciferol (400 [iU]/1) + Cyanocobalamin (5 ug/1) + DL-alpha tocopheryl acetate (30 [iU]/1) + Folic acid (1 mg/1) + Iron sucrose (29 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (15 ug/1) + Pyridoxine hydrochloride (2.5 mg/1) + Riboflavin (1.8 mg/1) + Thiamine mononitrate (1.6 mg/1) + Zinc oxide (15 mg/1)KitOralAcella Pharmaceuticals, LLC2013-05-172015-07-31Us
CitraNatal AssureDoconexent (300 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (124 mg/1) + Cholecalciferol (400 [iU]/1) + Copper (2 mg/1) + Docusate sodium (50 mg/1) + Folic acid (1 mg/1) + Icosapent (0.75 mg/1) + Iodine (150 ug/1) + Iron (35 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc (25 mg/1)OralMission Pharmacal Company2014-04-30Not applicableUs
CitraNatal AssureDoconexent (300 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (125 mg/1) + Cholecalciferol (400 [iU]/1) + Copper (2 mg/1) + Docusate sodium (50 mg/1) + Folic acid (1 mg/1) + Icosapent (0.75 mg/1) + Iodine (150 ug/1) + Iron (35 mg/1) + Nicotinamide (20 mg/1) + Pyridoxine hydrochloride (25 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin E (30 [iU]/1) + Zinc (25 mg/1)KitOralMission Pharmacal2008-11-19Not applicableUs
CitraNatal DHADoconexent (250 mg/1) + Ascorbic acid (120 mg/1) + Calcium citrate tetrahydrate (124 mg/1) + Cupric oxide (2 mg/1) + Docusate sodium (50 mg/1) + Folic acid (1 mg/1) + Icosapent (0.625 mg/1) + Iron (27 mg/1) + Nicotinamide (20 mg/1) + Potassium Iodide (150 mg/1) + Pyridoxine hydrochloride (20 mg/1) + Riboflavin (3.4 mg/1) + Thiamine chloride (3 mg/1) + Vitamin D (400 [iU]/1) + Zinc oxide (25 mg/1) + alpha-Tocopherol acetate (30 [iU]/1)KitOralMission Pharmacal Company2014-05-22Not applicableUs

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as very long-chain fatty acids. These are fatty acids with an aliphatic tail that contains at least 22 carbon atoms.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Fatty Acyls
Sub Class
Fatty acids and conjugates
Direct Parent
Very long-chain fatty acids
Alternative Parents
Unsaturated fatty acids / Straight chain fatty acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds
Substituents
Aliphatic acyclic compound / Carbonyl group / Carboxylic acid / Carboxylic acid derivative / Hydrocarbon derivative / Monocarboxylic acid or derivatives / Organic oxide / Organic oxygen compound / Organooxygen compound / Straight chain fatty acid
Molecular Framework
Aliphatic acyclic compounds
External Descriptors
omega-3 fatty acid, docosahexaenoic acid (CHEBI:28125) / Unsaturated fatty acids, Docosanoids, Polyunsaturated fatty acids (C06429) / Unsaturated fatty acids (LMFA01030185)

Chemical Identifiers

UNII
ZAD9OKH9JC
CAS number
6217-54-5
InChI Key
MBMBGCFOFBJSGT-KUBAVDMBSA-N
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-
IUPAC Name
(4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid
SMILES
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(O)=O

References

General References
  1. Calder PC: Omega-3 fatty acids and inflammatory processes. Nutrients. 2010 Mar;2(3):355-74. doi: 10.3390/nu2030355. Epub 2010 Mar 18. [PubMed:22254027]
  2. Kim HY: Novel metabolism of docosahexaenoic acid in neural cells. J Biol Chem. 2007 Jun 29;282(26):18661-5. Epub 2007 May 8. [PubMed:17488715]
  3. Picq M, Chen P, Perez M, Michaud M, Vericel E, Guichardant M, Lagarde M: DHA metabolism: targeting the brain and lipoxygenation. Mol Neurobiol. 2010 Aug;42(1):48-51. doi: 10.1007/s12035-010-8131-7. Epub 2010 Apr 28. [PubMed:20422316]
  4. Butovich IA, Lukyanova SM, Bachmann C: Dihydroxydocosahexaenoic acids of the neuroprotectin D family: synthesis, structure, and inhibition of human 5-lipoxygenase. J Lipid Res. 2006 Nov;47(11):2462-74. Epub 2006 Aug 9. [PubMed:16899822]
  5. Serhan CN, Gotlinger K, Hong S, Lu Y, Siegelman J, Baer T, Yang R, Colgan SP, Petasis NA: Anti-inflammatory actions of neuroprotectin D1/protectin D1 and its natural stereoisomers: assignments of dihydroxy-containing docosatrienes. J Immunol. 2006 Feb 1;176(3):1848-59. [PubMed:16424216]
  6. Mas E, Croft KD, Zahra P, Barden A, Mori TA: Resolvins D1, D2, and other mediators of self-limited resolution of inflammation in human blood following n-3 fatty acid supplementation. Clin Chem. 2012 Oct;58(10):1476-84. Epub 2012 Aug 21. [PubMed:22912397]
  7. Chen CT, Kitson AP, Hopperton KE, Domenichiello AF, Trepanier MO, Lin LE, Ermini L, Post M, Thies F, Bazinet RP: Plasma non-esterified docosahexaenoic acid is the major pool supplying the brain. Sci Rep. 2015 Oct 29;5:15791. doi: 10.1038/srep15791. [PubMed:26511533]
  8. Pawlosky RJ, Hibbeln JR, Novotny JA, Salem N Jr: Physiological compartmental analysis of alpha-linolenic acid metabolism in adult humans. J Lipid Res. 2001 Aug;42(8):1257-65. [PubMed:11483627]
  9. Pawlosky RJ, Hibbeln JR, Salem N Jr: Compartmental analyses of plasma n-3 essential fatty acids among male and female smokers and nonsmokers. J Lipid Res. 2007 Apr;48(4):935-43. Epub 2007 Jan 17. [PubMed:17234605]
  10. Cederholm T, Salem N Jr, Palmblad J: omega-3 fatty acids in the prevention of cognitive decline in humans. Adv Nutr. 2013 Nov 6;4(6):672-6. doi: 10.3945/an.113.004556. eCollection 2013 Nov. [PubMed:24228198]
  11. Guesnet P, Alessandri JM: Docosahexaenoic acid (DHA) and the developing central nervous system (CNS) - Implications for dietary recommendations. Biochimie. 2011 Jan;93(1):7-12. doi: 10.1016/j.biochi.2010.05.005. Epub 2010 May 15. [PubMed:20478353]
  12. Kelley DS, Siegel D, Fedor DM, Adkins Y, Mackey BE: DHA supplementation decreases serum C-reactive protein and other markers of inflammation in hypertriglyceridemic men. J Nutr. 2009 Mar;139(3):495-501. doi: 10.3945/jn.108.100354. Epub 2009 Jan 21. [PubMed:19158225]
  13. Arterburn LM, Hall EB, Oken H: Distribution, interconversion, and dose response of n-3 fatty acids in humans. Am J Clin Nutr. 2006 Jun;83(6 Suppl):1467S-1476S. [PubMed:16841856]
Human Metabolome Database
HMDB0002183
KEGG Compound
C06429
PubChem Compound
445580
PubChem Substance
46506213
ChemSpider
393183
BindingDB
50210259
RxNav
1006469
ChEBI
28125
ChEMBL
CHEMBL367149
ZINC
ZINC000004474564
PDBe Ligand
HXA
Wikipedia
Docosahexaenoic_acid
PDB Entries
1fdq / 1mv9 / 2byo / 2g7z / 2vv0 / 3hs7 / 5j0z / 5y5c
MSDS
Download (28.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedOtherBioavailability1
4CompletedTreatmentChild's Development / Premature Births1
4CompletedTreatmentObesity, Morbid1
4CompletedTreatmentOcular Surface Disease1
4RecruitingTreatmentObesity, Childhood1
3CompletedPreventionImprove Healthy Ageing in Seniors; Prevent Disease at Older Age1
3CompletedTreatmentAge-Related Macular Degeneration (ARMD) / Cataracts1
3CompletedTreatmentAlzheimer's Disease (AD)1
3CompletedTreatmentAttention Deficit Hyperactivity Disorder (ADHD)1
3CompletedTreatmentBMI >30 kg/m2 / Fatty Liver / Fibrosis, Liver / Metabolic Syndromes / Nonalcoholic Fatty Liver Disease1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleOral
Tablet, coatedOral
Capsule, delayed releaseOral0.6 mg
Tablet, film coatedOral
Capsule, delayed releaseOral150 mg
Capsule, liquid filledOral
Capsule, gelatin coatedOral
TabletOral
Capsule, coatedOral
Capsule, liquid filledOral1 mg
Capsule, liquid filledOral25 mg
Tablet, chewableOral
KitOral
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000186 mg/mLALOGPS
logP6.83ALOGPS
logP6.75ChemAxon
logS-6.2ALOGPS
pKa (Strongest Acidic)4.89ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count14ChemAxon
Refractivity111.39 m3·mol-1ChemAxon
Polarizability38.63 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9944
Blood Brain Barrier+0.9277
Caco-2 permeable+0.7696
P-glycoprotein substrateNon-substrate0.7069
P-glycoprotein inhibitor INon-inhibitor0.9369
P-glycoprotein inhibitor IINon-inhibitor0.9152
Renal organic cation transporterNon-inhibitor0.9399
CYP450 2C9 substrateNon-substrate0.8035
CYP450 2D6 substrateNon-substrate0.9101
CYP450 3A4 substrateNon-substrate0.7197
CYP450 1A2 substrateInhibitor0.6216
CYP450 2C9 inhibitorNon-inhibitor0.9094
CYP450 2D6 inhibitorNon-inhibitor0.964
CYP450 2C19 inhibitorNon-inhibitor0.9717
CYP450 3A4 inhibitorNon-inhibitor0.944
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9588
Ames testNon AMES toxic0.8998
CarcinogenicityNon-carcinogens0.627
BiodegradationReady biodegradable0.8443
Rat acute toxicity1.4856 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.873
hERG inhibition (predictor II)Non-inhibitor0.9343
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-004l-9800000000-86f34228f9e92b6da2c6
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-9800000000-86f34228f9e92b6da2c6
Mass Spectrum (Electron Ionization)MSsplash10-002f-9400000000-60bd7bfd4de9015476c7
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-IT , negativeLC-MS/MSsplash10-001i-0190000000-e6566b5aff7cefa4ae5d
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-004i-0069000000-c76c91e0abd1895adb8b
LC-MS/MS Spectrum - LC-ESI-QQ , negativeLC-MS/MSsplash10-001r-0069000000-a25e6a700612620a1217

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
General Function
Zinc ion binding
Specific Function
Ligand-activated transcription factor. Key regulator of lipid metabolism. Activated by the endogenous ligand 1-palmitoyl-2-oleoyl-sn-glycerol-3-phosphocholine (16:0/18:1-GPC). Activated by oleyleth...
Gene Name
PPARA
Uniprot ID
Q07869
Uniprot Name
Peroxisome proliferator-activated receptor alpha
Molecular Weight
52224.595 Da
References
  1. Liu M, Montgomery MK, Fiveash CE, Osborne B, Cooney GJ, Bell-Anderson K, Turner N: PPARalpha-independent actions of omega-3 PUFAs contribute to their beneficial effects on adiposity and glucose homeostasis. Sci Rep. 2014 Jul 2;4:5538. doi: 10.1038/srep05538. [PubMed:24986106]
  2. Rudkowska I, Garenc C, Couture P, Vohl MC: Omega-3 fatty acids regulate gene expression levels differently in subjects carrying the PPARalpha L162V polymorphism. Genes Nutr. 2009 Sep;4(3):199-205. doi: 10.1007/s12263-009-0129-2. Epub 2009 Jul 8. [PubMed:19585164]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Ligand
General Function
Zinc ion binding
Specific Function
Nuclear receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the nuclear receptor binds to DNA specific PPAR response elements (PPRE...
Gene Name
PPARG
Uniprot ID
P37231
Uniprot Name
Peroxisome proliferator-activated receptor gamma
Molecular Weight
57619.58 Da
References
  1. Varga T, Czimmerer Z, Nagy L: PPARs are a unique set of fatty acid regulated transcription factors controlling both lipid metabolism and inflammation. Biochim Biophys Acta. 2011 Aug;1812(8):1007-22. doi: 10.1016/j.bbadis.2011.02.014. Epub 2011 Mar 5. [PubMed:21382489]
  2. Edwards IJ, O'Flaherty JT: Omega-3 Fatty Acids and PPARgamma in Cancer. PPAR Res. 2008;2008:358052. doi: 10.1155/2008/358052. [PubMed:18769551]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRA
Uniprot ID
P19793
Uniprot Name
Retinoic acid receptor RXR-alpha
Molecular Weight
50810.835 Da
References
  1. German OL, Monaco S, Agnolazza DL, Rotstein NP, Politi LE: Retinoid X receptor activation is essential for docosahexaenoic acid protection of retina photoreceptors. J Lipid Res. 2013 Aug;54(8):2236-46. doi: 10.1194/jlr.M039040. Epub 2013 May 30. [PubMed:23723389]
  2. de Urquiza AM, Liu S, Sjoberg M, Zetterstrom RH, Griffiths W, Sjovall J, Perlmann T: Docosahexaenoic acid, a ligand for the retinoid X receptor in mouse brain. Science. 2000 Dec 15;290(5499):2140-4. [PubMed:11118147]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRB
Uniprot ID
P28702
Uniprot Name
Retinoic acid receptor RXR-beta
Molecular Weight
56921.38 Da
References
  1. German OL, Monaco S, Agnolazza DL, Rotstein NP, Politi LE: Retinoid X receptor activation is essential for docosahexaenoic acid protection of retina photoreceptors. J Lipid Res. 2013 Aug;54(8):2236-46. doi: 10.1194/jlr.M039040. Epub 2013 May 30. [PubMed:23723389]
  2. de Urquiza AM, Liu S, Sjoberg M, Zetterstrom RH, Griffiths W, Sjovall J, Perlmann T: Docosahexaenoic acid, a ligand for the retinoid X receptor in mouse brain. Science. 2000 Dec 15;290(5499):2140-4. [PubMed:11118147]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
General Function
Zinc ion binding
Specific Function
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expressi...
Gene Name
RXRG
Uniprot ID
P48443
Uniprot Name
Retinoic acid receptor RXR-gamma
Molecular Weight
50870.72 Da
References
  1. German OL, Monaco S, Agnolazza DL, Rotstein NP, Politi LE: Retinoid X receptor activation is essential for docosahexaenoic acid protection of retina photoreceptors. J Lipid Res. 2013 Aug;54(8):2236-46. doi: 10.1194/jlr.M039040. Epub 2013 May 30. [PubMed:23723389]
  2. de Urquiza AM, Liu S, Sjoberg M, Zetterstrom RH, Griffiths W, Sjovall J, Perlmann T: Docosahexaenoic acid, a ligand for the retinoid X receptor in mouse brain. Science. 2000 Dec 15;290(5499):2140-4. [PubMed:11118147]
  3. Wietrzych-Schindler M, Szyszka-Niagolov M, Ohta K, Endo Y, Perez E, de Lera AR, Chambon P, Krezel W: Retinoid x receptor gamma is implicated in docosahexaenoic acid modulation of despair behaviors and working memory in mice. Biol Psychiatry. 2011 Apr 15;69(8):788-94. doi: 10.1016/j.biopsych.2010.12.017. Epub 2011 Feb 21. [PubMed:21334601]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transcriptional activator activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
Transcriptional activator required for lipid homeostasis. Regulates transcription of the LDL receptor gene as well as the fatty acid and to a lesser degree the cholesterol synthesis pathway (By sim...
Gene Name
SREBF1
Uniprot ID
P36956
Uniprot Name
Sterol regulatory element-binding protein 1
Molecular Weight
121673.6 Da
References
  1. Patterson E, Wall R, Fitzgerald GF, Ross RP, Stanton C: Health implications of high dietary omega-6 polyunsaturated Fatty acids. J Nutr Metab. 2012;2012:539426. doi: 10.1155/2012/539426. Epub 2012 Apr 5. [PubMed:22570770]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Yao HT, Chang YW, Lan SJ, Chen CT, Hsu JT, Yeh TK: The inhibitory effect of polyunsaturated fatty acids on human CYP enzymes. Life Sci. 2006 Nov 25;79(26):2432-40. Epub 2006 Aug 23. [PubMed:16978661]
  2. Westphal C, Konkel A, Schunck WH: CYP-eicosanoids--a new link between omega-3 fatty acids and cardiac disease? Prostaglandins Other Lipid Mediat. 2011 Nov;96(1-4):99-108. doi: 10.1016/j.prostaglandins.2011.09.001. Epub 2011 Sep 16. [PubMed:21945326]

Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:52

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