CHEBI:18145 - (R,R,R)-α-tocopherol

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ChEBI Name (R,R,R)-α-tocopherol
ChEBI ID CHEBI:18145
ChEBI ASCII Name (R,R,R)-alpha-tocopherol
Definition An α-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of α-tocopherol, it is found particularly in sunflower and olive oils.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:46509, CHEBI:10336, CHEBI:12343
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Formula C29H50O2
Net Charge 0
Average Mass 430.70610
Monoisotopic Mass 430.38108
InChI 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
SMILES CC(C)CCC[C@@H](C)CCC[C@@H](C)CCC[C@]1(C)CCc2c(C)c(O)c(C)c(C)c2O1
Metabolite of Species Details
Mus musculus (NCBI:txid10090) From MetaboLights See: MetaboLights Study
Chlamydomonas reinhardtii (NCBI:txid3055) See: PubMed
Homo sapiens (NCBI:txid9606) See: DOI
Homo sapiens (NCBI:txid9606) Found in faeces (UBERON:0001988). See: PubMed
Homo sapiens (NCBI:txid9606) Found in saliva (UBERON:0001836). See: PubMed
Homo sapiens (NCBI:txid9606) Found in cerebrospinal fluid (UBERON:0001359). See: PubMed
Homo sapiens (NCBI:txid9606) Found in blood (UBERON:0000178). See: PubMed
Homo sapiens (NCBI:txid9606) Found in breast milk (ENVO:02000031). See: PubMed
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
(via tocol )
(via vitamin E )
food antioxidant
An antioxidant that used as a food additives to help guard against food deterioration.
(via alpha-tocopherol )
Biological Role(s): EC 2.7.11.13 (protein kinase C) inhibitor
An EC 2.7.11.* (protein-serine/threonine kinase) inhibitor that interferes with the action of protein kinase C (EC 2.7.11.13).
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
antiviral agent
A substance that destroys or inhibits replication of viruses.
micronutrient
Any nutrient required in small quantities by organisms throughout their life in order to orchestrate a range of physiological functions.
plant metabolite
Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
(via alpha-tocopherol )
algal metabolite
Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae.
food antioxidant
An antioxidant that used as a food additives to help guard against food deterioration.
(via alpha-tocopherol )
fat-soluble vitamin (role)
Any vitamin that dissolves in fats and are stored in body tissues. Unlike the water-soluble vitamins, they are stored in the body for long periods of time and generally pose a greater risk for toxicity when consumed in excess.
(via vitamin E )
Application(s): nutraceutical
A product in capsule, tablet or liquid form that provide essential nutrients, such as a vitamin, an essential mineral, a protein, an herb, or similar nutritional substance.
antiatherogenic agent
A cardiovascular drug that prevents atherogenesis, the accumulation of lipid-containing plaques on the innermost layers of the arteries. Compare with antiatherosclerotic agent.
anticoagulant
An agent that prevents blood clotting.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
food antioxidant
An antioxidant that used as a food additives to help guard against food deterioration.
(via alpha-tocopherol )
View more via ChEBI Ontology
ChEBI Ontology
Outgoing (R,R,R)-α-tocopherol (CHEBI:18145) has role algal metabolite (CHEBI:84735)
(R,R,R)-α-tocopherol (CHEBI:18145) has role antiatherogenic agent (CHEBI:50855)
(R,R,R)-α-tocopherol (CHEBI:18145) has role anticoagulant (CHEBI:50249)
(R,R,R)-α-tocopherol (CHEBI:18145) has role antioxidant (CHEBI:22586)
(R,R,R)-α-tocopherol (CHEBI:18145) has role antiviral agent (CHEBI:22587)
(R,R,R)-α-tocopherol (CHEBI:18145) has role EC 2.7.11.13 (protein kinase C) inhibitor (CHEBI:37700)
(R,R,R)-α-tocopherol (CHEBI:18145) has role immunomodulator (CHEBI:50846)
(R,R,R)-α-tocopherol (CHEBI:18145) has role micronutrient (CHEBI:27027)
(R,R,R)-α-tocopherol (CHEBI:18145) has role nutraceutical (CHEBI:50733)
(R,R,R)-α-tocopherol (CHEBI:18145) has role plant metabolite (CHEBI:76924)
(R,R,R)-α-tocopherol (CHEBI:18145) is a α-tocopherol (CHEBI:22470)
(R,R,R)-α-tocopherol (CHEBI:18145) is enantiomer of (S,S,S)-α-tocopherol (CHEBI:46430)
Incoming 13-hydroxy-α-tocopherol (CHEBI:84962) has functional parent (R,R,R)-α-tocopherol (CHEBI:18145)
(S,S,S)-α-tocopherol (CHEBI:46430) is enantiomer of (R,R,R)-α-tocopherol (CHEBI:18145)
IUPAC Name
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol
Synonyms Sources
(+)-α-tocopherol UniProt
(+)-alpha-tocopherol ChemIDplus
(+)-α-tocopherol ChemIDplus
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol IUPAC
(2R)-2,5,7,8-TETRAMETHYL-2-[(4R,8R)-4,8,12-TRIMETHYLTRIDECYL]CHROMAN-6-OL PDBeChem
(2R,4'R,8'R)-alpha-tocopherol ChemIDplus
(2R,4'R,8'R)-α-tocopherol ChemIDplus
(all-R)-α-tocopherol ChemIDplus
(R,R,R)-α-tocopherol ChemIDplus
5,7,8-trimethyltocol ChemIDplus
alpha-Tocopherol KEGG COMPOUND
d-α-tocopherol ChemIDplus
RRR-α-tocopherol ChEBI
Vitamin E KEGG COMPOUND
Manual Xrefs Databases
14265 ChemSpider
4280 DrugCentral
Alpha-Tocopherol Wikipedia
ALPHA-TOCOPHEROL MetaCyc
C00007366 KNApSAcK
C02477 KEGG COMPOUND
DB00163 DrugBank
FDB000565 FooDB
HMDB0001893 HMDB
LMPR02020001 LIPID MAPS
VIV PDBeChem
View more database links
Registry Numbers Types Sources
5300493 Beilstein Registry Number Beilstein
59-02-9 CAS Registry Number KEGG COMPOUND
59-02-9 CAS Registry Number NIST Chemistry WebBook
59-02-9 CAS Registry Number ChemIDplus
94012 Beilstein Registry Number Beilstein
94012 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11427352 PubMed citation Europe PMC
12899840 PubMed citation Europe PMC
14657365 PubMed citation Europe PMC
16512933 PubMed citation Europe PMC
17031012 PubMed citation Europe PMC
17310859 PubMed citation Europe PMC
19389964 PubMed citation Europe PMC
19663978 PubMed citation Europe PMC
20209471 PubMed citation Europe PMC
21591326 PubMed citation Europe PMC
23599266 PubMed citation Europe PMC
28694484 PubMed citation Europe PMC
31013594 PubMed citation Europe PMC
33197771 PubMed citation Europe PMC
Last Modified
04 August 2021