Doconexent

Identification

Summary

Doconexent is an omega 3 fatty acid used in a variety of nutritional supplements to support central nervous system and cardiovascular health.

Brand Names
Animi-3 With Vitamin D, Citranatal Harmony
Generic Name
Doconexent
DrugBank Accession Number
DB03756
Background

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
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
  • Docosahexanoic Acid

Pharmacology

Indication

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

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to treatFredrickson classification type iv hyperlipidemiaCombination Product in combination with: Icosapent ethyl (DB08887)•••••••••••••••••••••• •••••••• •• •••••••••••
Used as adjunct in combination to treatFredrickson type iib hyperlipidemiaCombination Product in combination with: Icosapent ethyl (DB08887)•••••••••••••••••••••• •••••••• •• ••••• •••••••••• •••••••••••• ••••••• •••• ••••••• ••••••••••••
Used as adjunct in combination to treatType iii hyperlipidaemiaCombination Product in combination with: Icosapent ethyl (DB08887)•••••••••••••••••••••• •••••••••••• ••••••• •••• ••••••• •••••• •••••••••• •••••••• •• •••••••••••
Associated Therapies
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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 14.

TargetActionsOrganism
APeroxisome proliferator-activated receptor alpha
activator
Humans
APeroxisome proliferator-activated receptor gamma
activator
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
UMyc proto-oncogene protein
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.

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Route of elimination

Not Available

Half-life

Approximately 20 hours 9.

Clearance

Not Available

Adverse Effects
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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.

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.
AbrocitinibThe metabolism of Abrocitinib can be decreased when combined with Doconexent.
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.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Doconexent sodium295P7EPT4C81926-93-4SNNDEWVSGZRIFE-FPYKSTABSA-M
Product Images
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
GESTAVIT DHADoconexent (350 mg) + Calcium carbonate (312.5 mg) + Cholecalciferol (0.4 mg) + Cyanocobalamin (2.2 mg) + Folic acid (0.6 mg) + Iron (150 mg) + Nicotinamide (17 mg) + Pyridoxine hydrochloride (4 mg) + Riboflavin (3.4 mg) + Sodium ascorbate (78.7333 mg) + Thiamine mononitrate (3 mg) + Vitamin A palmitate (1.5671 mg) + Vitamin E (10 mg) + Zinc oxide (18.671 mg)Capsule, delayed releaseOralPROCAPS S.A.2010-03-242015-07-02Colombia flag
HerbalifelineDoconexent (78 mg) + Icosapent (119 mg)CapsuleOralHerbalife International Of Luxembourg S À R L2004-07-192009-07-21Canada flag
Omegaven "Fresenius" - Emulsion zur InfusionDoconexent (2.265 g) + Choline (1.2 g) + Glycerin (2.5 g) + Icosapent (2.035 g) + Vitamin E (0.0223 g)EmulsionParenteralFresenius Kabi Austria Gmb H1998-05-18Not applicableAustria flag
OMEGOILDoconexent (380 MG) + Icosapent ethyl (460 mg)CapsuleOralIbsa Farmaceutici Italia S.R.L.2014-10-062022-01-12Italy flag
OMEGOILDoconexent (380 MG) + Icosapent ethyl (460 mg)CapsuleOralIbsa Farmaceutici Italia S.R.L.2014-10-062022-01-12Italy flag
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 flag
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 flag
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 flag
BP Vit 3Doconexent (350 mg/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) + beta-Sitosterol (200 mg/1)Capsule, coatedOralAcella Pharmaceuticals, LLC2009-04-17Not applicableUS flag
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 flag

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)
Affected organisms
Not Available

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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  14. 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. [Article]
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 / 7wkb / 8eit
show 5 more
MSDS
Download (28.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentBarrett's Esophagus / Obesity1
4CompletedTreatmentDevelopment, Child / Premature Births1
4CompletedTreatmentObesity, Morbid1
4CompletedTreatmentOcular Surface Disease1
4Unknown StatusTreatmentArrhythmia / Coronary Artery Disease (CAD)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
CapsuleOral
Tablet, chewableOral
Tablet, coatedOral
Capsule, liquid filled; kit; tabletOral
GelOral
Capsule, delayed releaseOral
Capsule, liquid filledOral
EmulsionOral
Tablet, film coatedOral
Capsule, coatedOral
Capsule, gelatin coated; kit; tabletOral
TabletOral300 mg
Capsule, liquid filled; kit; tablet, film coatedOral
EmulsionParenteral
Injection, emulsionIntravenous
Capsule, liquid filledOral
Capsule, gelatin coatedOral
TabletOral
Capsule; kit; tablet, coatedOral
Capsule, coatedOral
Capsule; kit; tablet, film coatedOral
Capsule, liquid filled; kitOral
EmulsionOral
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
Polarizability38.47 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-MSsplash10-0690-5590000000-145821d84e425eec8f98
GC-MS Spectrum - GC-MSGC-MSsplash10-004l-9800000000-86f34228f9e92b6da2c6
Mass Spectrum (Electron Ionization)MSsplash10-002f-9400000000-60bd7bfd4de9015476c7
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-3889000000-f8fb12ea348d43452c25
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-c9a23bbdb1f6741615a7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0429000000-fc115d3f21d4ee12bb66
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-7591000000-ba0f6d4c9b7dbf89ad38
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0apv-3491000000-ed4fb9cbe25f7364ebf9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00o3-9740000000-109d5deef4d29d32034a
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-01t9-3889000000-f8fb12ea348d43452c25
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0009000000-c9a23bbdb1f6741615a7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0429000000-fc115d3f21d4ee12bb66
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-7591000000-ba0f6d4c9b7dbf89ad38
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0apv-3491000000-ed4fb9cbe25f7364ebf9
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00o3-9740000000-109d5deef4d29d32034a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-238.0743914
predicted
DarkChem Lite v0.1.0
[M-H]-238.1231914
predicted
DarkChem Lite v0.1.0
[M-H]-238.0391914
predicted
DarkChem Lite v0.1.0
[M-H]-238.8162914
predicted
DarkChem Lite v0.1.0
[M-H]-191.85579
predicted
DeepCCS 1.0 (2019)
[M-H]-238.0743914
predicted
DarkChem Lite v0.1.0
[M-H]-238.1231914
predicted
DarkChem Lite v0.1.0
[M-H]-238.0391914
predicted
DarkChem Lite v0.1.0
[M-H]-238.8162914
predicted
DarkChem Lite v0.1.0
[M-H]-191.85579
predicted
DeepCCS 1.0 (2019)
[M+H]+194.21379
predicted
DeepCCS 1.0 (2019)
[M+H]+194.21379
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.32823
predicted
DeepCCS 1.0 (2019)
[M+Na]+201.32823
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
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. [Article]
  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. [Article]
  3. Ji HG, Piao JY, Kim SJ, Kim DH, Lee HN, Na HK, Surh YJ: Docosahexaenoic acid inhibits Helicobacter pylori-induced STAT3 phosphorylation through activation of PPARgamma. Mol Nutr Food Res. 2016 Jun;60(6):1448-57. doi: 10.1002/mnfr.201600009. Epub 2016 May 9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Activator
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. [Article]
  2. Edwards IJ, O'Flaherty JT: Omega-3 Fatty Acids and PPARgamma in Cancer. PPAR Res. 2008;2008:358052. doi: 10.1155/2008/358052. [Article]
  3. Ji HG, Piao JY, Kim SJ, Kim DH, Lee HN, Na HK, Surh YJ: Docosahexaenoic acid inhibits Helicobacter pylori-induced STAT3 phosphorylation through activation of PPARgamma. Mol Nutr Food Res. 2016 Jun;60(6):1448-57. doi: 10.1002/mnfr.201600009. Epub 2016 May 9. [Article]
  4. Li H, Ruan XZ, Powis SH, Fernando R, Mon WY, Wheeler DC, Moorhead JF, Varghese Z: EPA and DHA reduce LPS-induced inflammation responses in HK-2 cells: evidence for a PPAR-gamma-dependent mechanism. Kidney Int. 2005 Mar;67(3):867-74. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
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. [Article]
  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. [Article]
  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. [Article]
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. [Article]
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
Transcription factor that binds DNA in a non-specific manner, yet also specifically recognizes the core sequence 5'-CAC[GA]TG-3'. Activates the transcription of growth-related genes.
Gene Name
MYC
Uniprot ID
P01106
Uniprot Name
Myc proto-oncogene protein
Molecular Weight
48803.55 Da
References
  1. Ji HG, Piao JY, Kim SJ, Kim DH, Lee HN, Na HK, Surh YJ: Docosahexaenoic acid inhibits Helicobacter pylori-induced STAT3 phosphorylation through activation of PPARgamma. Mol Nutr Food Res. 2016 Jun;60(6):1448-57. doi: 10.1002/mnfr.201600009. Epub 2016 May 9. [Article]

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. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 03, 2022 09:37