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Natural Product (NP) Details

General Information of the NP (ID: NP0140)
Name
Vitamin E
Synonyms
alpha-Tocopherol; VITAMIN E; D-alpha-Tocopherol; 59-02-9; 5,7,8-Trimethyltocol; (+)-alpha-Tocopherol; alpha-Vitamin E; Aquasol E; (R,R,R)-alpha-Tocopherol; Phytogermine; Eprolin; (2R,4'R,8'R)-alpha-Tocopherol; dl-a-Tocopherol; Denamone; Viteolin; Esorb; a-Tocopherol; Tocopherol alpha; alpha Tocopherol; 2074-53-5; (2R)-2,5,7,8-TETRAMETHYL-2-[(4R,8R)-4,8,12-TRIMETHYLTRIDECYL]CHROMAN-6-OL; Vitamin Ea; Mixed tocopherols; D-alpha tocopherol; Syntopherol; (R)-2,5,7,8-Tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-ol; Tocopherol (R,S); UNII-N9PR3490H9; CHEBI:18145; (+/-)-alpha-Tocopherol; 2,5,7,8-Tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol; Evitaminum; Profecundin; Waynecomycin; Almefrol; Emipherol; Epsilan; Etamican; Tokopharm; Vascuals; Vitayonon; Etavit; Ilitia; Evion; 1406-18-4; (2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol; BPBio1_000362; Vitaplex E; Eprolin S; Spavit E; ido-E; Endo E; N9PR3490H9; Vita E; Lan-E; Med-E; Antisterility vitamin; MFCD00072045; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-; Vi-E; E307; DSSTox_CID_6339; DSSTox_RID_78103; DSSTox_GSID_26339; alpha-Tocopherol, D-; Viprimol; alpha-Tokoferol; Vitamin E alpha; Viterra E; E Prolin; (2R)-2-((4R,8R)-4,8,12-trimethyltridecyl)-2,5,7,8-tetramethylchroman-6-ol; CAS-59-02-9; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, (2R-(2R*(4R*,8R*)))-; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-; SMR000471844; VIV; (+/-)-alpha-Tocopherol, 95%, synthetic; alpha-Tocopherol acid; Tenox GT 1; Rhenogran Ronotec 50; Covitol F 1000; 3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol; E 307 (tocopherol); (all-R)-alpha-Tocopherol; Phytogermin; Palmvtee; alpha-Tocoferol; (+-)-Med-E; E-Oil 1000; Vitamin Ealpha; CCRIS 3588; MFCD00072051; a-D-Tocopherol; HSDB 2556; Pheryl-E; Vita plus E; d-..-Tocopherol; NCGC00016688-02; Vitamin E, liquid; (+)--tocopherol; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-; Prestwick_653; EINECS 200-412-2; EINECS 215-798-8; EINECS 218-197-9; .alpha.-Vitamin E; (+)-a-Tocopherol; NSC 20812; NSC 82623; RRR-alpha-tocopherol; RRR-alpha-tocopheryl; Vitamin E (liquid); Vitamin E [USP]; ()-alpha-Tocopherol; delta-alpha-tocopherol; alpha-delta-Tocopherol; Vitamin E (D-form); CHEMBL47; (R,R,R)-a-Tocopherol; Prestwick3_000404; E 307; (+)-.alpha.-Tocopherol; all-rac-alpha-Tocopherolum; bmse000600; EC 200-412-2; SCHEMBL3097; DL-all-rac-alpha-Tocopherol; UNII-H4N855PNZ1; BIDD:PXR0174; D-alpha-Tocopherol, 97+%; BSPBio_000328; MLS001066396; MLS001335981; MLS001335982; BIDD:ER0562; T1539_SIGMA; H4N855PNZ1; DTXSID0026339; (2R,4'R,8'R)-a-Tocopherol; HMS2096A10; HMS2231G08; C29H50O2 (D-alpha-tocopherol); HY-N0683; ZINC4095858; Tox21_110563; Tox21_113208; Tox21_202081; BDBM50458513; LMPR02020001; MFCD00006848; AKOS004910417; CS-8161; DB00163; MCULE-3684036705; NCGC00142625-01; NCGC00142625-04; NCGC00142625-05; NCGC00142625-06; NCGC00142625-07; NCGC00142625-10; NCGC00259630-01; (2R*(4R*,8R*))-(1)-3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol; 18920-62-2; AS-13990; M349; P500; ST073358; (+/-)-alpha-Tocopherol (Vitamin E) solution; C02477; d-alpha, d-beta, d-gamma & d-delta tocopherols; Q158348; Q-201932; W-107596; W-109164; 07AA93F0-3339-4EEC-B50B-ADB70F657087; UNII-7QWA1RIO01 component GVJHHUAWPYXKBD-IEOSBIPESA-N; UNII-N53I4V2IA6 component GVJHHUAWPYXKBD-IEOSBIPESA-N; UNII-R0ZB2556P8 component GVJHHUAWPYXKBD-IEOSBIPESA-N; (+)-alpha-Tocopherol, from vegetable oil, Type V, ~1000 IU/g; (2R,4'R,8'R)-2,5,7,8-Tetramethyl-2-(4',8',12'-trimethyltridecyl)-6-chromanol; 3,4-Dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-2H-1- -benzopyran-6-ol; (+)-alpha-Tocopherol, Type VI, from vegetable oil, neat (liquid, >=0.88M based on potency, density and molecular wt.), BioReagent, suitable for insect cell culture, >=1000 IU/g; (2R)-3,4-Dihydro-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol; (R)-2,5,7,8-tetramethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-3,4-dihydro-2H-chromen-6-ol; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, 2R- 2R*(4R*,8R*) -; 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,7,8-tetramethyl-2-(4,8,12-trimethyltridecyl)-, (2R*(4R*,8R*))-(+-)- (9CI)
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Species Origin Salmo salar ...     Click to Show/Hide
Salmo salar
Kingdom: Metazoa
Phylum: Chordata
Class: Actinopteri
Order: Salmoniformes
Family: Salmonidae
Genus: Salmo
Species: Salmo salar
Disease Cardiovascular disease [ICD-11: BA00-BE2Z] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C29H50O2
PubChem CID
14985
Canonical SMILES
CC1=C(C2=C(CCC(O2)(C)CCCC(C)CCCC(C)CCCC(C)C)C(=C1O)C)C
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
InChIKey
GVJHHUAWPYXKBD-IEOSBIPESA-N
CAS Number
CAS 59-02-9
ChEBI ID
CHEBI:18145
Herb ID
HBIN048051
SymMap ID
SMIT01672
TCMSP ID
MOL007180
TTD Drug ID
D02TQO
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Drug(s) Whose Efficacy can be Enhanced by This NP
          Gefitinib      Lung cancer     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
                    In-vitro Model NRK-49F CVCL_2144 Healthy Rattus norvegicus
                    Experimental
                    Result(s)
A combined treatment with low-dose gefitinib and vitamin E has synergistic effects that reduce TGF Beta1 induced fibroblast proliferation, cell-cycle arrest and the ERK phosphorylation pathway.
          Aspirin      Pain     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
                    In-vitro Model J774.1A Mouse reticulum cell sarcoma Mus musculus
                    Experimental
                    Result(s)
Anti-inflammatory therapy might be successful with lower aspirin doses when combined with vitamin E, thereby possibly avoiding the side effects of the usually required high dose aspirin treatment.
          FTY720      Psychoactive substances use disorder     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression HMOX1  Molecule Info 
Pathway MAP
Up-regulation Expression SOD Cu-Zn  Molecule Info 
Pathway MAP
                    In-vivo Model Sprague-Dawley rats were used in this study.
                    Experimental
                    Result(s)
Pre treatment with FTY720 combined with vitamin E exerts synergistic neuroprotective effects in the simulated cerebral ischemia in vitro.
          Celecoxib      Rheumatoid arthritis     Click to Show/Hide the Molecular Data of This Drug
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Phosphorylation AKT1  Molecule Info 
Pathway MAP
Down-regulation Expression COX-2  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation p105  Molecule Info 
Pathway MAP
                    In-vitro Model +SA mammary epithelial cells' Healthy Homo sapiens
                    Experimental
                    Result(s)
Combination therapy with these agents may provide enhanced therapeutic response in breast cancer patients, while avoiding the toxicity associated with high-dose COX-2 inhibitor monotherapy.
    β. A List of Drug(s) Whose Adverse Effect can be Decreased by This NP
          S-adenosylmethionine      Hepatic fibrosis/cirrhosis     Click to Show/Hide the Molecular Data of This Drug
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Male C57BL/6 mice between 8-10 weeks were injected with DMSO, 15 mg/kg doxorubicin, or doxorubicin plus 25 mg/kg visnagin or 10 mg/kg diphenylurea intraperitoneally (n=4-5 each).
                    Experimental
                    Result(s)
There are synergistic antioxidative effects among the antioxidants, SAMe and vitamins C and E, that protect the liver from TAA-induced HDIR, suggesting that antioxidant treatment may best be done using a balanced "cocktail.".
References
Reference 1 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
Reference 2 Combined treatment with vitamin E and gefitinib has synergistic effects to inhibit TGF-Beta1-induced renal fibroblast proliferation. Mol Med Rep. 2016 Jun;13(6):5372-8.
Reference 3 Synergistic inhibition of cyclooxygenase-2 expression by vitamin E and aspirin. Free Radic Biol Med. 2000 Dec;29(11):1135-42.
Reference 4 Synergistic protective effect of FTY720 and vitamin E against simulated cerebral ischemia in vitro. Mol Med Rep. 2017 Jul;16(1):396-402.
Reference 5 Synergistic anticancer effects of combined gamma-tocotrienol and celecoxib treatment are associated with suppression in Akt and NFkappaB signaling. Biomed Pharmacother. 2010 May;64(5):327-32.
Reference 6 Synergistic protection by S-adenosylmethionine with vitamins C and E on liver injury induced by thioacetamide in rats. Free Radic Biol Med. 2006 Feb 15;40(4):617-24.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China