Summary Vitamin E is an antioxidant vitamin used in many skin creams and multivitamin preparations. Show Mvc-fluoride, Vitafol-one Generic NameVitamin EDrugBank Accession NumberDB00163BackgroundIn 1922, vitamin E was demonstrated to be an essential nutrient12. Vitamin E is a term used to describe 8 different fat soluble tocopherols and tocotrienols, alpha-tocopherol being the most biologically active1. Vitamin E acts as an antioxidant, protecting cell membranes from oxidative damage1. The antioxidant effects are currently being researched for use in the treatment of diseases causing bone loss, cardiovascular diseases, diabetes mellitus and associated comorbidities, eye diseases, inflammatory diseases (including skin conditions), lipid disorders, neurological diseases, and radiation damage13. Though this research is so far inconclusive, vitamin E remains a popular supplement and is generally considered safe by the FDALabel. TypeSmall MoleculeGroupsApproved, Nutraceutical, Vet approvedStructure Monoisotopic: 430.381080844 Chemical FormulaC29H50O2Synonyms
Vitamin E supplementation is indicated for treatment of vitamin E deficiency which can occur in cystic fibrosis, cholestasis and severe liver disease, abetalipoproteinemia or simply poor diet1,15. Reduce drug development failure rates Build, train, & validate machine-learning models Build, train, & validate predictive machine-learning models with structured datasets. Associated Conditions
Avoid life-threatening adverse drug events Improve clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more. Avoid life-threatening adverse drug events & improve clinical decision support. PharmacodynamicsVitamin E is a collective term used to describe 8 separate fat soluble antioxidants, most commonly alpha-tocopherol1. Vitamin E acts to protect cells against the effects of free radicals, which are potentially damaging by-products of the body's metabolism. Vitamin E deficiency is seen in persons with abetalipoproteinemia, premature, very low birth weight infants (birth weights less than 1500 grams, or 3½ pounds), cystic fibrosis, and cholestasis and severe liver disease1. Preliminary research suggests vitamin E may help prevent or delay coronary heart disease and protect against the damaging effects of free radicals, which may contribute to the development of chronic diseases such as cancer2. It also protects other fat-soluble vitamins (A and B group vitamins) from destruction by oxygen3. Low levels of vitamin E have been linked to increased incidence of breast and colon cancer16. Mechanism of actionThe mechanism of action for most of vitamin E's effects are still unknown1,4. Vitamin E is an antioxidant, preventing free radical reactions with cell membranes10. Though in some cases vitamin E has been shown to have pro-oxidant activity10. One mechanism of vitamin E's antioxidant effect is in the termination of lipid peroxidation11. Vitamin E reacts with unstable lipid radicals, producing stable lipids and a relatively stable vitamin E radical11. The vitamin E radical is then reduced back to stable vitamin E by reaction with ascorbate or glutathione11.
10-33% of deuterium labelled vitamin E is absorbed in the small intestine5,15. Absorption of Vitamin E is dependant upon absorption of the fat in which it is dissolved15,1. For patients with poor fat absorption, a water soluble form of vitamin E may need to be substituted such as tocopheryl polyethylene glycol-1000 succinate15. In other studies the oral bioavailability of alpha-tocopherol was 36%, gamma-tocotrienol was 9%14. The time to maximum concentration was 9.7 hours for alpha-tocopherol and 2.4 hours for gamma-tocotrienol14. Volume of distribution0.41L/kg in premature neonates given a 20mg/kg intramuscular injection6. Protein bindingVitamin E is bound to lipoproteins in blood1,11. MetabolismAlpha and gamma tocopherol are undergo beta oxidation and a process mediated by cytochrome P450s such as CYP4F2, CYP3A4, and CYP3A57. These processes convert alpha and gamma tocopherol to alpha-CEHC (2,5,7,8-tetramethyl-2-(2’-carboxyethyl)-6-hydroxychroman) and gamma-CEHC (2,7,8-trimethyl-2-(2’-carboxyethyl)-6-hydroxychroman) respectively, however the full process is not known7. Hover over products below to view reaction partners Route of eliminationAlpha tocopherol is excreted in urine as well as bile in the feces mainly as a carboxyethyl-hydrochroman (CEHC) metabolite, but it can be excreted in it's natural form 8. Half-life44 hours in premature neonates given a 20mg/kg intramuscular injection6. 12 minutes in intravenous injection of intestinal lymph11. Clearance6.5mL/hr/kg in premature neonates given a 20mg/kg intramuscular injection6. Adverse EffectsImprove decision support & research outcomes With structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. Improve decision support & research outcomes with our structured adverse effects data. ToxicityThere is no data available for effects in pregnancy, breast feeding, hepatic impairment, or renal impairment. However, it appears that the process of vitamin E elimination is strict and self regulating enough that vitamin E toxicity is exceedingly rare8,9. Studies showing adverse effects from excess vitamin E generally involve people consuming more than 1000mg/day for weeks to months15. PathwaysNot AvailablePharmacogenomic Effects/ADRs Not AvailableDrug InteractionsThis 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.
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InChI=1S/C29H50O2/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8)19-17-26-25(7)27(30)23(5)24(6)28(26)31-29/h20-22,30H,9-19H2,1-8H3/t21-,22-,29-/m1/s1 IUPAC Name(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol SMILESCC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(O1)C(C)=C(C)C(O)=C2C Synthesis ReferenceRalph E. Close, William Oroshnik, "Synthesis of dehydrophytol and Vitamin E." U.S. Patent US4039591, issued February, 1945. US4039591General References
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ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397) Mass Spec (NIST)Not AvailableSpectra
TargetsBuild, predict & validate machine-learning models Use our structured and evidence-based datasets to unlock new Use our structured and evidence-based datasets to unlock new insights and accelerate drug research. KindProteinOrganismHumansPharmacological action Unknown Also identified as TAP3, this protein binds to Vitamin E , though the exact bond conformation has not been studied.General FunctionTransporter activitySpecific FunctionProbable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids.Gene NameSEC14L4Uniprot IDQ9UDX3Uniprot NameSEC14-like protein 4Molecular Weight46643.385 Da References
KindProteinOrganismHumans Pharmacological action Unknown General FunctionTransporter activitySpecific FunctionProbable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids.Gene NameSEC14L3Uniprot IDQ9UDX4Uniprot NameSEC14-like protein 3Molecular Weight46047.835 Da References
KindProteinOrganismHumansPharmacological action Unknown General FunctionVitamin e bindingSpecific FunctionCarrier protein. Binds to some hydrophobic molecules and promotes their transfer between the different cellular sites. Binds with high affinity to alpha-tocopherol. Also binds with a weaker affinit...Gene NameSEC14L2Uniprot IDO76054Uniprot NameSEC14-like protein 2Molecular Weight46144.9 Da References
KindProteinOrganismHumansPharmacological action Unknown General FunctionZinc ion bindingSpecific FunctionNuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism an...Gene NameNR1I2Uniprot IDO75469Uniprot NameNuclear receptor subfamily 1 group I member 2Molecular Weight49761.245 Da References
KindProteinOrganismHumansPharmacological action Unknown General FunctionZinc ion bindingSpecific FunctionCalcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase involved in various cellular processes such as regulation of the B-cell receptor (BCR) signalosom...Gene NamePRKCBUniprot IDP05771Uniprot NameProtein kinase C beta typeMolecular Weight76868.45 Da References
KindProteinOrganismHumansPharmacological action Unknown General FunctionIron ion bindingSpecific FunctionCatalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.Gene NameALOX5Uniprot IDP09917Uniprot NameArachidonate 5-lipoxygenase Molecular Weight77982.595 Da References
KindProteinOrganismHumansPharmacological action Unknown General FunctionZinc ion bindingSpecific FunctionCalcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase that is involved in positive and negative regulation of cell proliferation, apoptosis, differenti...Gene NamePRKCAUniprot IDP17252Uniprot NameProtein kinase C alpha typeMolecular Weight76749.445 Da References
KindProteinOrganismHumansPharmacological action Unknown The studies referenced have shown that vitamin E (VtE) activates the DGKα isoform in vitro and in vivo in the mouse knockout model.General FunctionPhospholipid bindingSpecific FunctionUpon cell stimulation converts the second messenger diacylglycerol into phosphatidate, initiating the resynthesis of phosphatidylinositols and attenuating protein kinase C activity.Gene NameDGKAUniprot IDP23743Uniprot NameDiacylglycerol kinase alphaMolecular Weight82629.55 Da References
KindProteinOrganismHumansPharmacological action Unknown Vitamin E's effects and inhibition of PKC is linked to its activation of protein phosphatases and their subsequent downstream effects.General FunctionProtein serine/threonine phosphatase activitySpecific FunctionPP2A can modulate the activity of phosphorylase B kinase casein kinase 2, mitogen-stimulated S6 kinase, and MAP-2 kinase.Gene NamePPP2CBUniprot IDP62714Uniprot NameSerine/threonine-protein phosphatase 2A catalytic subunit beta isoformMolecular Weight35574.85 Da References
KindProteinOrganism HumansPharmacological action Unknown Vitamin E's effects and inhibition of PKC is linked to its activation of protein phosphatases and their subsequent downstream effects.General FunctionPP2A is the major phosphatase for microtubule-associated proteins (MAPs). PP2A can modulate the activity of phosphorylase B kinase casein kinase 2, mitogen-stimulated S6 kinase, and MAP-2 kinase. Cooperates with SGO2 to protect centromeric cohesin from separase-mediated cleavage in oocytes specifically during meiosis I (By similarity). Can dephosphorylate SV40 large T antigen and p53/TP53. Activates RAF1 by dephosphorylating it at 'Ser-259'.Specific FunctionGaba receptor bindingGene NamePPP2CAUniprot IDP67775Uniprot NameSerine/threonine-protein phosphatase 2A catalytic subunit alpha isoformMolecular Weight35593.93 Da References
EnzymesKindProteinOrganismHumansPharmacological action Unknown ActionsInhibitor General FunctionS-nitrosoglutathione bindingSpecific FunctionConjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. Regulates negatively CDK5 activity via p25/p35 translocation to prevent neurodegeneration.Gene NameGSTP1Uniprot IDP09211Uniprot NameGlutathione S-transferase PMolecular Weight23355.625 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsInhibitor General FunctionOxidoreductase activitySpecific FunctionExhibits glutathione-dependent thiol transferase and dehydroascorbate reductase activities. Has S-(phenacyl)glutathione reductase activity. Has also glutathione S-transferase activity. Participates...Gene NameGSTO1Uniprot IDP78417Uniprot NameGlutathione S-transferase omega-1Molecular Weight27565.6 Da References
KindProteinOrganismHumans Pharmacological action Unknown ActionsInducer General FunctionProtein homodimerization activitySpecific FunctionConjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles. May govern uptake and detoxification of both endogenous compounds and xenobiotics at the t... Gene NameGSTM3Uniprot IDP21266Uniprot NameGlutathione S-transferase Mu 3Molecular Weight26559.32 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsInducer General FunctionMagnesium ion bindingSpecific FunctionNot AvailableGene NameGCLCUniprot IDP48506Uniprot NameGlutamate--cysteine ligase catalytic subunitMolecular Weight72765.14 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsInducer General FunctionSuperoxide dismutase activitySpecific FunctionThe enzyme apparently serves as a quinone reductase in connection with conjugation reactions of hydroquinons involved in detoxification pathways as well as in biosynthetic processes such as the vit...Gene NameNQO1Uniprot IDP15559Uniprot NameNAD(P)H dehydrogenase [quinone] 1Molecular Weight30867.405 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsInducer General FunctionSignal transducer activitySpecific FunctionHeme oxygenase cleaves the heme ring at the alpha methene bridge to form biliverdin. Biliverdin is subsequently converted to bilirubin by biliverdin reductase. Under physiological conditions, the a...Gene NameHMOX1Uniprot IDP09601Uniprot NameHeme oxygenase 1Molecular Weight32818.345 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsInducer General FunctionZinc ion bindingSpecific FunctionDestroys radicals which are normally produced within the cells and which are toxic to biological systems.Gene NameSOD1Uniprot IDP00441Uniprot NameSuperoxide dismutase [Cu-Zn]Molecular Weight15935.685 Da References
KindProtein OrganismHumansPharmacological action Unknown ActionsSubstrate Inducer Cytochrome P450 3A4 performs omega-hydroxylation on vitamin E in the first step of vitamin E's metabolism.General FunctionVitamin d3 25-hydroxylase activitySpecific FunctionCytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...Gene NameCYP3A4Uniprot IDP08684Uniprot NameCytochrome P450 3A4Molecular Weight57342.67 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsInducer General FunctionGlutathione transferase activitySpecific FunctionConjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.Gene NameGSTA2Uniprot IDP09210Uniprot NameGlutathione S-transferase A2Molecular Weight25663.675 Da References
CarriersKindProteinOrganismHumansPharmacological action Unknown ActionsBinder SEC14-like protein 2 may be involved in intracellular transport of alpha tocopherol to the mitochondria.General FunctionVitamin e bindingSpecific FunctionCarrier protein. Binds to some hydrophobic molecules and promotes their transfer between the different cellular sites. Binds with high affinity to alpha-tocopherol. Also binds with a weaker affinit...Gene NameSEC14L2Uniprot IDO76054Uniprot NameSEC14-like protein 2Molecular Weight46144.9 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsBinder SEC14-like protein 3 may be involved in intracellular transport of alpha tocopherol to the mitochondria.General FunctionTransporter activitySpecific FunctionProbable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids.Gene NameSEC14L3Uniprot IDQ9UDX4Uniprot NameSEC14-like protein 3Molecular Weight46047.835 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsBinder General Function Facilitates the transfer of a spectrum of different lipid molecules, including diacylglycerol, phosphatidic acid, sphingomyelin, phosphatidylcholine, phosphatidylglycerol, cerebroside and phosphatidyl ethanolamine. Essential for the transfer of excess surface lipids from triglyceride-rich lipoproteins to HDL, thereby facilitating the formation of smaller lipoprotein remnants, contributing to the formation of LDL, and assisting in the maturation of HDL particles. PLTP also plays a key role in the uptake of cholesterol from peripheral cells and tissues that is subsequently transported to the liver for degradation and excretion. Two distinct forms of PLTP exist in plasma: an active form that can transfer PC from phospholipid vesicles to high-density lipoproteins (HDL), and an inactive form that lacks this capability.Specific FunctionCeramide bindingGene NamePLTPUniprot IDP55058Uniprot NamePhospholipid transfer proteinMolecular Weight54738.85 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsBinder General FunctionVitamin e bindingSpecific FunctionBinds alpha-tocopherol, enhances its transfer between separate membranes, and stimulates its release from liver cells (PubMed:7887897). Binds both phosphatidylinol 3,4-bisphosphate and phosphatidyl...Gene NameTTPAUniprot IDP49638Uniprot NameAlpha-tocopherol transfer proteinMolecular Weight31749.305 Da TransportersKindProteinOrganismHumansPharmacological action Unknown ActionsSubstrate SR-BI transporters mediate tocopherol uptake across the brush border membrane in intestinal Caco-2 cells and mouse modelsGeneral FunctionVirus receptor activitySpecific FunctionReceptor for different ligands such as phospholipids, cholesterol ester, lipoproteins, phosphatidylserine and apoptotic cells. Probable receptor for HDL, located in particular region of the plasma ...Gene NameSCARB1Uniprot ID Q8WTV0Uniprot NameScavenger receptor class B member 1Molecular Weight60877.385 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsSubstrate This transporter is involved in the intestinal absorption of alpha and gamma tocopherolGeneral FunctionSyntaxin bindingSpecific FunctioncAMP-dependent and sulfonylurea-sensitive anion transporter. Key gatekeeper influencing intracellular cholesterol transport.Gene NameABCA1Uniprot IDO95477Uniprot NameATP-binding cassette sub-family A member 1Molecular Weight254299.89 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsSubstrate This transporter is involved in intestinal alpha tocopherol absorptionGeneral FunctionRab gtpase bindingSpecific FunctionPlays a major role in cholesterol homeostasis. Is critical for the uptake of cholesterol across the plasma membrane of the intestinal enterocyte. Is the direct molecular target of ezetimibe, a drug...Gene NameNPC1L1Uniprot IDQ9UHC9Uniprot NameNiemann-Pick C1-like protein 1Molecular Weight148726.52 Da References
KindProteinOrganismHumansPharmacological action Unknown ActionsSubstrate General FunctionToxin transporter activitySpecific FunctionTransporter involved in macrophage lipid homeostasis. Is an active component of the macrophage lipid export complex. Could also be involved in intracellular lipid transport processes. The role in c...Gene NameABCG1Uniprot IDP45844Uniprot NameATP-binding cassette sub-family G member 1Molecular Weight75591.275 Da References
Drug created at June 13, 2005 13:24 / Updated at September 27, 2022 08:31 |
Chewable vitamin e antioxidant protection for cellular health
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