D-alpha-Tocopherol acetate

Identification

Summary

D-alpha-Tocopherol acetate is a form of vitamin E used to treat and prevent vitamin deficiencies.

Generic Name
D-alpha-Tocopherol acetate
DrugBank Accession Number
DB14002
Background

Alpha-tocopherol is the primary form of vitamin E that is preferentially used by the human body to meet appropriate dietary requirements. In particular, the RRR-alpha-tocopherol (or sometimes called the d-alpha-tocopherol stereoisomer) stereoisomer is considered the natural formation of alpha-tocopherol and generally exhibits the greatest bioavailability out of all of the alpha-tocopherol stereoisomers. Moreover, RRR-alpha-tocopherol acetate is a relatively stabilized form of vitamin E that is most commonly used as a food additive when needed 6.

Alpha-tocopherol acetate is subsequently most commonly indicated for dietary supplementation in individuals who may demonstrate a genuine deficiency in vitamin E. Vitamin E itself is naturally found in various foods, added to others, or used in commercially available products as a dietary supplement. The recommended dietary allowances (RDAs) for vitamin E alpha-tocopherol are: males = 4 mg (6 IU) females = 4 mg (6 IU) in ages 0-6 months, males = 5 mg (7.5 IU) females = 5 mg (7.5 IU) in ages 7-12 months, males = 6 mg (9 IU) females = 6 mg (9 IU) in ages 1-3 years, males = 7 mg (10.4 IU) females = 7 mg (10.4 IU) in ages 4-8 years, males = 11 mg (16.4 IU) females = 11 mg (16.4 IU) in ages 9-13 years, males = 15 mg (22.4 IU) females = 15 mg (22.4 IU) pregnancy = 15 mg (22.4 IU) lactation = 19 mg (28.4 IU) in ages 14+ years 11. Most individuals obtain adequate vitamin E intake from their diets; genuine vitamin E deficiency is considered to be rare.

Nevertheless, vitamin E is known to be a fat-soluble antioxidant that has the capability to neutralize endogenous free radicals. This biologic action of vitamin E consequently continues to generate ongoing interest and study in whether or not its antioxidant abilities may be used to help assist in preventing or treating a number of different conditions like cardiovascular disease, ocular conditions, diabetes, cancer and more. At the moment however, there exists a lack of formal data and evidence to support any such additional indications for vitamin E use.

Type
Small Molecule
Groups
Approved, Nutraceutical, Vet approved
Structure
Weight
Average: 472.7428
Monoisotopic: 472.39164553
Chemical Formula
C31H52O3
Synonyms
  • (+)-alfa-tocopherol acetate
  • alpha-tocopheryl acetate, D-
  • D-alpha tocoferil acetate
  • D-alpha tocopheryl acetate
  • D-alpha-Tocopheryl acetate
  • RRR-alpha-tocopheryl acetate
  • Vitamin E acetate, D-
External IDs
  • T-3376

Pharmacology

Indication

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

Vitamin E, known for its antioxidant activities, is protective against cardiovascular disease and some forms of cancer and has also demonstrated immune-enhancing effects. It may be of limited benefit in some with asthma and rheumatoid arthritis. It may be helpful in some neurological diseases including Alzheimer's, some eye disorders including cataracts, and diabetes and premenstrual syndrome. It may also help protect skin from ultraviolet irradiation although claims that it reverses skin aging, enhances male fertility and exercise performance are poorly supported. It may help relieve some muscle cramps.

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Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

Vitamin E has antioxidant activity. It may also have anti-atherogenic, antithrombotic, anticoagulant, neuroprotective, antiviral, immunomodulatory, cell membrane-stabilizing and antiproliferative actions. Vitamin E is a collective term used to describe eight separate forms, the best-known form being alpha-tocopherol. Vitamin E is a fat-soluble vitamin and is an important antioxidant. It acts to protect cells against the effects of free radicals, which are potentially damaging by-products of the body's metabolism. Vitamin E is often used in skin creams and lotions because it is believed to play a role in encouraging skin healing and reducing scarring after injuries such as burns. There are three specific situations when a vitamin E deficiency is likely to occur. It is seen in persons who cannot absorb dietary fat, has been found in premature, very low birth weight infants (birth weights less than 1500 grams, or 3½ pounds), and is seen in individuals with rare disorders of fat metabolism. A vitamin E deficiency is usually characterized by neurological problems due to poor nerve conduction. Symptoms may include infertility, neuromuscular impairment, menstrual problems, miscarriage and uterine degradation. Preliminary research has led to a widely held belief that vitamin E may help prevent or delay coronary heart disease. Antioxidants such as vitamin E help protect against the damaging effects of free radicals, which may contribute to the development of chronic diseases such as cancer. It also protects other fat-soluble vitamins (A and B group vitamins) from destruction by oxygen. Low levels of vitamin E have been linked to increased incidence of breast and colon cancer.

Mechanism of action

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

Although all forms of Vitamin E exhibit antioxidant activity, it is known that the antioxidant activity of vitamin E is not sufficient to explain the vitamin's biological activity.
Vitamin E's anti-atherogenic activity involves the inhibition of the oxidation of LDL and the accumulation of oxLDL in the arterial wall. It also appears to reduce oxLDL-induced apoptosis in human endothelial cells. Oxidation of LDL is a key early step in atherogenesis as it triggers a number of events which lead to the formation of atherosclerotic plaque. In addition, vitamin E inhibits protein kinase C (PKC) activity. PKC plays a role in smooth muscle cell proliferation, and, thus, the inhibition of PKC results in inhibition of smooth muscle cell proliferation, which is involved in atherogenesis.
Vitamin E's antithrombotic and anticoagulant activities involves the downregulation of the expression of intracellular cell adhesion molecule(ICAM)-1 and vascular cell adhesion molecule(VCAM)-1 which lowers the adhesion of blood components to the endothelium. In addition, vitamin E upregulates the expression of cytosolic phospholipase A2 and cyclooxygenase (COX)-1 which in turn enhances the release of prostacyclin. Prostacyclin is a vasodilating factor and inhibitor of platelet aggregation and platelet release. It is also known that platelet aggregation is mediated by a mechanism involving the binding of fibrinogen to the glycoprotein IIb/IIIa (GPIIb/IIIa) complex of platelets. GPIIb/IIIa is the major membrane receptor protein that is key to the role of the platelet aggregation response. GPIIb is the alpha-subunit of this platelet membrane protein. Alpha-tocopherol downregulates GPIIb promoter activity which results in reduction of GPIIb protein expression and decreased platelet aggregation. Vitamin E has also been found in culture to decrease plasma production of thrombin, a protein which binds to platelets and induces aggregation. A metabolite of vitamin E called vitamin E quinone or alpha-tocopheryl quinone (TQ) is a potent anticoagulant. This metabolite inhibits vitamin K-dependent carboxylase, which is a major enzyme in the coagulation cascade.
The neuroprotective effects of vitamin E are explained by its antioxidant effects. Many disorders of the nervous system are caused by oxidative stress. Vitamin E protects against this stress, thereby protecting the nervouse system.
The immunomodulatory effects of Vitamin E have been demonstrated in vitro, where alpha-tocopherol increases mitogenic response of T lymphocytes from aged mice. The mechanism of this response by vitamin E is not well understood, however it has been suggested that vitamin E itself may have mitogenic activity independent of its antioxidant activity.
Lastly, the mechanism of action of vitamin E's antiviral effects (primarily against HIV-1) involves its antioxidant activity. Vitamin E reduces oxidative stress, which is thought to contribute to HIV-1 pathogenesis, as well as to the pathogenesis of other viral infections. Vitamin E also affects membrane integrity and fluidity and, since HIV-1 is a membraned virus, altering membrane fluidity of HIV-1 may interfere with its ability to bind to cell-receptor sites, thus decreasing its infectivity.

TargetActionsOrganism
USEC14-like protein 3Not AvailableHumans
USEC14-like protein 2Not AvailableHumans
UNuclear receptor subfamily 1 group I member 2Not AvailableHumans
UProtein kinase C beta typeNot AvailableHumans
UArachidonate 5-lipoxygenaseNot AvailableHumans
UProtein kinase C alpha typeNot AvailableHumans
Absorption

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

50 to 80% absorbed from gastrointestinal tract.

Volume of distribution

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

Protein binding

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

Bound to beta-lipoproteins in blood.

Metabolism

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

Hepatic.

Hover over products below to view reaction partners

Route of elimination

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

Half-life

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

Clearance

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

Adverse Effects
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Toxicity

In addition to any following information, owing to d-alpha-Tocopherol acetate's closely related chemical nature with alpha-Tocopherol acetate, please also refer to the drug information page for alpha-Tocopherol acetate for further data.

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
OrlistatOrlistat can cause a decrease in the absorption of D-alpha-Tocopherol acetate resulting in a reduced serum concentration and potentially a decrease in efficacy.
Food Interactions
No interactions found.

Products

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Active Moieties
NameKindUNIICASInChI Key
Vitamin EprodrugN9PR3490H959-02-9GVJHHUAWPYXKBD-IEOSBIPESA-N
TocofersolanprodrugO03S90U1F29002-96-4Not applicable
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Aquasol E Capsules 100 I.U.Capsule100 unitOralColumbia Laboratories1996-07-302006-07-11Canada flag
Aquasol E Capsules 100unitCapsule100 unit / capOralRhone Poulenc Rorer1992-12-311997-08-13Canada flag
Clear Base E 800iu CapCapsule800 unit / capOralGahler Enterprises Ltd.1994-12-312008-07-17Canada flag
E Vitamin 200 I.U. (natural Source) - CapCapsule200 unit / capOralH.J. Sutton Industries Ltd.1996-10-251998-08-31Canada flag
E Vitamin 400 I.U. (natural Source)-capCapsule400 unit / capOralH.J. Sutton Industries Ltd.1996-10-251998-08-31Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Allbee C 800 TabD-alpha-Tocopherol acetate (45 unit) + Ascorbic acid (800 mg) + Cyanocobalamin (17 mcg) + Nicotinamide (100 mg) + Calcium pantothenate (33 mg) + Pyridoxine hydrochloride (30 mg) + Riboflavin (17 mg) + Thiamine mononitrate (15 mg)TabletOralWhitehall Robins Inc.1994-12-312003-08-01Canada flag
C.E.b12 Complex PwrD-alpha-Tocopherol acetate (6 unit / g) + Ascorbic acid (200 mg / g) + Cyanocobalamin (1.8 mcg / g)PowderOralPure Life International Prods Inc.1993-12-312002-07-04Canada flag
Cheon Shim Bo HwaD-alpha-Tocopherol acetate (1 mg/1) + Borage oil (311 mg/1)CapsuleOralSaimdang Cosmetics Co., Ltd2011-04-06Not applicableUS flag
Cheon Shim Bo YunD-alpha-Tocopherol acetate (3 mg/1) + N-Acetylglucosamine (263 mg/1) + Soy isoflavones (30 mg/1)CapsuleOralSaimdang Cosmetics Co., Ltd2010-11-08Not applicableUS flag
Childrens Chewab Vitamin W Chel MineralsD-alpha-Tocopherol acetate (25 unit) + Ascorbic acid (75 mg) + Biotin (50 mcg) + Cyanocobalamin (10 mcg) + Folic acid (10 mcg) + Iodine (1 mg) + Iron (5 mg) + Nicotinamide (10 mg) + Pantothenic acid (10 mg) + Pyridoxine (5 mg) + Riboflavin (5 mg) + Thiamine (5 mg) + Vitamin A (5000 unit) + Vitamin D (400 unit)TabletOralAnabolic Laboratories Inc.1981-12-311996-10-02Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Active OBD-alpha-Tocopherol acetate (30 [iU]/1) + Ascorbic acid (100 mg/1) + Cholecalciferol (400 [iU]/1) + Cupric sulfate pentahydrate (2 mg/1) + Cyanocobalamin (30 ug/1) + Doconexent (320 mg/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
Cheon Shim Bo HwaD-alpha-Tocopherol acetate (1 mg/1) + Borage oil (311 mg/1)CapsuleOralSaimdang Cosmetics Co., Ltd2011-04-06Not applicableUS flag
Cheon Shim Bo YunD-alpha-Tocopherol acetate (3 mg/1) + N-Acetylglucosamine (263 mg/1) + Soy isoflavones (30 mg/1)CapsuleOralSaimdang Cosmetics Co., Ltd2010-11-08Not applicableUS flag
Duet DHAD-alpha-Tocopherol acetate (3 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (2800 [iU]/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (820 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Folic acid (1 mg/1) + Iodine (220 ug/1) + Iron (25 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (430 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1)KitOralWh Nutritionals, Llc2011-09-092014-12-31US flag
Duet DHAD-alpha-Tocopherol acetate (3 mg/1) + Ascorbic acid (120 mg/1) + Beta carotene (2800 [iU]/1) + Calcium carbonate (200 mg/1) + Cholecalciferol (820 [iU]/1) + Cupric oxide (2 mg/1) + Cyanocobalamin (12 ug/1) + Folic acid (1 mg/1) + Iodine (220 ug/1) + Iron (25 mg/1) + Magnesium oxide (25 mg/1) + Nicotinamide (20 mg/1) + Omega-3 fatty acids (400 mg/1) + Pyridoxine hydrochloride (50 mg/1) + Riboflavin (4 mg/1) + Thiamine mononitrate (1.8 mg/1) + Zinc oxide (25 mg/1)KitOralWh Nutritionals, Llc2011-09-092014-12-31US flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
A7E6112E4N
CAS number
58-95-7
InChI Key
ZAKOWWREFLAJOT-CEFNRUSXSA-N
InChI
InChI=1S/C31H52O3/c1-21(2)13-10-14-22(3)15-11-16-23(4)17-12-19-31(9)20-18-28-26(7)29(33-27(8)32)24(5)25(6)30(28)34-31/h21-23H,10-20H2,1-9H3/t22-,23-,31-/m1/s1
IUPAC Name
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-yl acetate
SMILES
CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCC2=C(C)C(OC(C)=O)=C(C)C(C)=C2O1

References

General References
  1. Iuliano L, Micheletta F, Maranghi M, Frati G, Diczfalusy U, Violi F: Bioavailability of vitamin E as function of food intake in healthy subjects: effects on plasma peroxide-scavenging activity and cholesterol-oxidation products. Arterioscler Thromb Vasc Biol. 2001 Oct;21(10):E34-7. [Article]
  2. Miller ER 3rd, Pastor-Barriuso R, Dalal D, Riemersma RA, Appel LJ, Guallar E: Meta-analysis: high-dosage vitamin E supplementation may increase all-cause mortality. Ann Intern Med. 2005 Jan 4;142(1):37-46. Epub 2004 Nov 10. [Article]
  3. Horwitt MK, Elliott WH, Kanjananggulpan P, Fitch CD: Serum concentrations of alpha-tocopherol after ingestion of various vitamin E preparations. Am J Clin Nutr. 1984 Aug;40(2):240-5. [Article]
  4. Rumbold AR, Crowther CA, Haslam RR, Dekker GA, Robinson JS: Vitamins C and E and the risks of preeclampsia and perinatal complications. N Engl J Med. 2006 Apr 27;354(17):1796-806. [Article]
  5. Poston L, Briley AL, Seed PT, Kelly FJ, Shennan AH: Vitamin C and vitamin E in pregnant women at risk for pre-eclampsia (VIP trial): randomised placebo-controlled trial. Lancet. 2006 Apr 8;367(9517):1145-54. [Article]
  6. Schmolz L, Birringer M, Lorkowski S, Wallert M: Complexity of vitamin E metabolism. World J Biol Chem. 2016 Feb 26;7(1):14-43. doi: 10.4331/wjbc.v7.i1.14. [Article]
  7. Zondlo Fiume M: Final report on the safety assessment of Tocopherol, Tocopheryl Acetate, Tocopheryl Linoleate, Tocopheryl Linoleate/Oleate, Tocopheryl Nicotinate, Tocopheryl Succinate, Dioleyl Tocopheryl Methylsilanol, Potassium Ascorbyl Tocopheryl Phosphate, and Tocophersolan. Int J Toxicol. 2002;21 Suppl 3:51-116. doi: 10.1080/10915810290169819. [Article]
  8. Ricciarelli R, Tasinato A, Clement S, Ozer NK, Boscoboinik D, Azzi A: alpha-Tocopherol specifically inactivates cellular protein kinase C alpha by changing its phosphorylation state. Biochem J. 1998 Aug 15;334 ( Pt 1):243-9. doi: 10.1042/bj3340243. [Article]
  9. Institute of Medicine (US) Panel on Dietary Antioxidants and Related Compounds (2000). Dietary Reference Intakes for Vitamin C, Vitamin E, Selenium, and Carotenoids. National Academies Press (US). [ISBN:0309069491]
  10. Linus Pauling Institute Micronutrient Information Center: Vitamin E [Link]
  11. National Institute for Health [Link]
  12. Cosmetic Ingredient Review: Safety Assessment of Tocopherols and Tocotrienols as Used in Cosmetics [Link]
  13. Journal of Clinical & Experimental Cardiology: Pharmacokinetics and Bioavailability of Annatto δ-tocotrienol in Healthy Fed Subjects [Link]
KEGG Drug
D01735
KEGG Compound
C13202
ChemSpider
77987
RxNav
1441649
ChEBI
32321
ChEMBL
CHEMBL1047
ZINC
ZINC000004172337
Wikipedia
Tocopheryl_acetate
MSDS
Download (47.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedPreventionPre-Eclampsia1
2, 3CompletedBasic ScienceType 2 Diabetes Mellitus1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Capsule, liquid filledOral
PowderOral
CapsuleOral
CapsuleOral800 unit / cap
CapsuleOral
Capsule, gelatin coated; kit; tabletOral
Capsule, liquid filled; kit; tabletOral
KitOral
CapsuleOral600 unit / cap
LotionTopical
LiquidTopical
Tablet, chewableOral
Tablet, film coatedOral
Paste, dentifriceOral
Capsule, gelatin coatedOral
Suspension / dropsOral
TabletOral
LiquidOral
Tablet, coatedOral
TabletOral2.5 unit / tab
Tablet, extended releaseOral
TabletOral400 unit / cap
CapsuleOral100 unit
CapsuleOral100 unit / cap
CapsuleOral400 unit / cap
CapsuleOral200 unit / cap
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility2.93e-06 mg/mLALOGPS
logP9.19ALOGPS
logP10.42Chemaxon
logS-8.2ALOGPS
pKa (Strongest Basic)-4.9Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area35.53 Å2Chemaxon
Rotatable Bond Count14Chemaxon
Refractivity144.53 m3·mol-1Chemaxon
Polarizability60.48 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MSGC-MSsplash10-0159-3910400000-2250f523f7b8e8106e4e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-3031900000-7f12936e1677f07e3ac1
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00b9-0000900000-fb1577f3e93415fffde4
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9000100000-068498bcc2744d5a75df
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0bti-4001900000-203db291537a6a7415d1
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-060r-9216300000-e84db64d7d376799e31c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0api-9340100000-dad501303885af430c99
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]-244.1563355
predicted
DarkChem Lite v0.1.0
[M-H]-243.0611355
predicted
DarkChem Lite v0.1.0
[M-H]-219.73743
predicted
DeepCCS 1.0 (2019)
[M+H]+245.0323355
predicted
DarkChem Lite v0.1.0
[M+H]+244.0306355
predicted
DarkChem Lite v0.1.0
[M+H]+222.133
predicted
DeepCCS 1.0 (2019)
[M+Na]+243.9073355
predicted
DarkChem Lite v0.1.0
[M+Na]+243.5128355
predicted
DarkChem Lite v0.1.0
[M+Na]+228.04553
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transporter activity
Specific Function
Probable hydrophobic ligand-binding protein; may play a role in the transport of hydrophobic ligands like tocopherol, squalene and phospholipids.
Gene Name
SEC14L3
Uniprot ID
Q9UDX4
Uniprot Name
SEC14-like protein 3
Molecular Weight
46047.835 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Ye X, Ji C, Yin G, Tang R, Zeng L, Gu S, Ying K, Xie Y, Zhao RC, Mao Y: Characterization of a human Sec14-like protein cDNA SEC14L3 highly homologous to human SPF/TAP. Mol Biol Rep. 2004 Mar;31(1):59-63. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Vitamin e binding
Specific Function
Carrier 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 Name
SEC14L2
Uniprot ID
O76054
Uniprot Name
SEC14-like protein 2
Molecular Weight
46144.9 Da
References
  1. Neuzil J, Dong LF, Wang XF, Zingg JM: Tocopherol-associated protein-1 accelerates apoptosis induced by alpha-tocopheryl succinate in mesothelioma cells. Biochem Biophys Res Commun. 2006 May 19;343(4):1113-7. Epub 2006 Mar 31. [Article]
  2. Ni J, Pang ST, Yeh S: Differential retention of alpha-vitamin E is correlated with its transporter gene expression and growth inhibition efficacy in prostate cancer cells. Prostate. 2007 Apr 1;67(5):463-71. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear 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 Name
NR1I2
Uniprot ID
O75469
Uniprot Name
Nuclear receptor subfamily 1 group I member 2
Molecular Weight
49761.245 Da
References
  1. Rabovsky A, Cuomo J, Eich N: Measurement of plasma antioxidant reserve after supplementation with various antioxidants in healthy subjects. Clin Chim Acta. 2006 Sep;371(1-2):55-60. Epub 2006 Mar 6. [Article]
  2. Meijerman I, Beijnen JH, Schellens JH: Herb-drug interactions in oncology: focus on mechanisms of induction. Oncologist. 2006 Jul-Aug;11(7):742-52. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Calcium-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 Name
PRKCB
Uniprot ID
P05771
Uniprot Name
Protein kinase C beta type
Molecular Weight
76868.45 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Wigg SJ, Tare M, Forbes J, Cooper ME, Thomas MC, Coleman HA, Parkington HC, O'Brien RC: Early vitamin E supplementation attenuates diabetes-associated vascular dysfunction and the rise in protein kinase C-beta in mesenteric artery and ameliorates wall stiffness in femoral artery of Wistar rats. Diabetologia. 2004 Jun;47(6):1038-46. Epub 2004 Jun 8. [Article]
  4. Huang Y, Ishizuka T, Miura A, Kajita K, Ishizawa M, Kimura M, Yamamoto Y, Kawai Y, Morita H, Uno Y, Yasuda K: Effect of 1 alpha,25-dihydroxy vitamin D3 and vitamin E on insulin-induced glucose uptake in rat adipocytes. Diabetes Res Clin Pract. 2002 Mar;55(3):175-83. [Article]
  5. Ganz MB, Seftel A: Glucose-induced changes in protein kinase C and nitric oxide are prevented by vitamin E. Am J Physiol Endocrinol Metab. 2000 Jan;278(1):E146-52. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Iron ion binding
Specific Function
Catalyzes the first step in leukotriene biosynthesis, and thereby plays a role in inflammatory processes.
Gene Name
ALOX5
Uniprot ID
P09917
Uniprot Name
Arachidonate 5-lipoxygenase
Molecular Weight
77982.595 Da
References
  1. Taccone-Gallucci M, Manca-di-Villahermosa S, Battistini L, Stuffler RG, Tedesco M, Maccarrone M: N-3 PUFAs reduce oxidative stress in ESRD patients on maintenance HD by inhibiting 5-lipoxygenase activity. Kidney Int. 2006 Apr;69(8):1450-4. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Calcium-activated, phospholipid- and diacylglycerol (DAG)-dependent serine/threonine-protein kinase that is involved in positive and negative regulation of cell proliferation, apoptosis, differenti...
Gene Name
PRKCA
Uniprot ID
P17252
Uniprot Name
Protein kinase C alpha type
Molecular Weight
76749.445 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Azzi A, Boscoboinik D, Clement S, Marilley D, Ozer NK, Ricciarelli R, Tasinato A: Alpha-tocopherol as a modulator of smooth muscle cell proliferation. Prostaglandins Leukot Essent Fatty Acids. 1997 Oct;57(4-5):507-14. [Article]
  4. Sylvester PW, McIntyre BS, Gapor A, Briski KP: Vitamin E inhibition of normal mammary epithelial cell growth is associated with a reduction in protein kinase C(alpha) activation. Cell Prolif. 2001 Dec;34(6):347-57. [Article]
  5. Huang Y, Ishizuka T, Miura A, Kajita K, Ishizawa M, Kimura M, Yamamoto Y, Kawai Y, Morita H, Uno Y, Yasuda K: Effect of 1 alpha,25-dihydroxy vitamin D3 and vitamin E on insulin-induced glucose uptake in rat adipocytes. Diabetes Res Clin Pract. 2002 Mar;55(3):175-83. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Glutathione transferase activity
Specific Function
Conjugation of reduced glutathione to a wide number of exogenous and endogenous hydrophobic electrophiles.
Gene Name
GSTA2
Uniprot ID
P09210
Uniprot Name
Glutathione S-transferase A2
Molecular Weight
25663.675 Da
References
  1. Feng Z, Liu Z, Li X, Jia H, Sun L, Tian C, Jia L, Liu J: alpha-Tocopherol is an effective Phase II enzyme inducer: protective effects on acrolein-induced oxidative stress and mitochondrial dysfunction in human retinal pigment epithelial cells. J Nutr Biochem. 2010 Dec;21(12):1222-31. doi: 10.1016/j.jnutbio.2009.10.010. Epub 2010 Feb 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
S-nitrosoglutathione binding
Specific Function
Conjugation 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 Name
GSTP1
Uniprot ID
P09211
Uniprot Name
Glutathione S-transferase P
Molecular Weight
23355.625 Da
References
  1. Ralat LA, Colman RF: Identification of tyrosine 79 in the tocopherol binding site of glutathione S-transferase pi. Biochemistry. 2006 Oct 17;45(41):12491-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity
Specific Function
Exhibits glutathione-dependent thiol transferase and dehydroascorbate reductase activities. Has S-(phenacyl)glutathione reductase activity. Has also glutathione S-transferase activity. Participates...
Gene Name
GSTO1
Uniprot ID
P78417
Uniprot Name
Glutathione S-transferase omega-1
Molecular Weight
27565.6 Da
References
  1. Sampayo-Reyes A, Zakharyan RA: Tocopherol esters inhibit human glutathione S-transferase omega. Acta Biochim Pol. 2006;53(3):547-52. Epub 2006 Oct 1. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Protein homodimerization activity
Specific Function
Conjugation 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 Name
GSTM3
Uniprot ID
P21266
Uniprot Name
Glutathione S-transferase Mu 3
Molecular Weight
26559.32 Da
References
  1. Mustacich DJ, Gohil K, Bruno RS, Yan M, Leonard SW, Ho E, Cross CE, Traber MG: Alpha-tocopherol modulates genes involved in hepatic xenobiotic pathways in mice. J Nutr Biochem. 2009 Jun;20(6):469-76. doi: 10.1016/j.jnutbio.2008.05.007. Epub 2008 Sep 11. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Magnesium ion binding
Specific Function
Not Available
Gene Name
GCLC
Uniprot ID
P48506
Uniprot Name
Glutamate--cysteine ligase catalytic subunit
Molecular Weight
72765.14 Da
References
  1. Feng Z, Liu Z, Li X, Jia H, Sun L, Tian C, Jia L, Liu J: alpha-Tocopherol is an effective Phase II enzyme inducer: protective effects on acrolein-induced oxidative stress and mitochondrial dysfunction in human retinal pigment epithelial cells. J Nutr Biochem. 2010 Dec;21(12):1222-31. doi: 10.1016/j.jnutbio.2009.10.010. Epub 2010 Feb 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Superoxide dismutase activity
Specific Function
The 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 Name
NQO1
Uniprot ID
P15559
Uniprot Name
NAD(P)H dehydrogenase [quinone] 1
Molecular Weight
30867.405 Da
References
  1. Feng Z, Liu Z, Li X, Jia H, Sun L, Tian C, Jia L, Liu J: alpha-Tocopherol is an effective Phase II enzyme inducer: protective effects on acrolein-induced oxidative stress and mitochondrial dysfunction in human retinal pigment epithelial cells. J Nutr Biochem. 2010 Dec;21(12):1222-31. doi: 10.1016/j.jnutbio.2009.10.010. Epub 2010 Feb 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Signal transducer activity
Specific Function
Heme 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 Name
HMOX1
Uniprot ID
P09601
Uniprot Name
Heme oxygenase 1
Molecular Weight
32818.345 Da
References
  1. Feng Z, Liu Z, Li X, Jia H, Sun L, Tian C, Jia L, Liu J: alpha-Tocopherol is an effective Phase II enzyme inducer: protective effects on acrolein-induced oxidative stress and mitochondrial dysfunction in human retinal pigment epithelial cells. J Nutr Biochem. 2010 Dec;21(12):1222-31. doi: 10.1016/j.jnutbio.2009.10.010. Epub 2010 Feb 12. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Zinc ion binding
Specific Function
Destroys radicals which are normally produced within the cells and which are toxic to biological systems.
Gene Name
SOD1
Uniprot ID
P00441
Uniprot Name
Superoxide dismutase [Cu-Zn]
Molecular Weight
15935.685 Da
References
  1. Feng Z, Liu Z, Li X, Jia H, Sun L, Tian C, Jia L, Liu J: alpha-Tocopherol is an effective Phase II enzyme inducer: protective effects on acrolein-induced oxidative stress and mitochondrial dysfunction in human retinal pigment epithelial cells. J Nutr Biochem. 2010 Dec;21(12):1222-31. doi: 10.1016/j.jnutbio.2009.10.010. Epub 2010 Feb 12. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Vitamin e binding
Specific Function
Binds 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 Name
TTPA
Uniprot ID
P49638
Uniprot Name
Alpha-tocopherol transfer protein
Molecular Weight
31749.305 Da

Drug created at March 25, 2018 19:28 / Updated at June 12, 2020 16:53