CHEBI:18145 - (R,R,R)-α-tocopherol

ChEBI IDCHEBI:18145
ChEBI Name(R,R,R)-α-tocopherol
Stars
ASCII Name(R,R,R)-alpha-tocopherol
DefinitionAn α-tocopherol that has R,R,R configuration. The naturally occurring stereoisomer of α-tocopherol, it is found particularly in sunflower and olive oils.
Secondary ChEBI IDsCHEBI:10336, CHEBI:12343, CHEBI:46509
Last Modified3 January 2023
DownloadsMolfile
FormulaC29H50O2
Net Charge0
Average Mass430.717
Monoisotopic Mass430.38108
SMILESCc1c(C)c2c(c(C)c1O)CC[C@@](C)(CCC[C@H](C)CCC[C@H](C)CCCC(C)C)O2
InChIInChI=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
InChIKeyGVJHHUAWPYXKBD-IEOSBIPESA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Chlamydomonas reinhardtii (ncbitaxon:3055) - PubMed (25515814)
Homo sapiens (ncbitaxon:9606)
faeces (UBERON:0001988) PubMed (24029555)
saliva (UBERON:0001836) PubMed (17623524)
cerebrospinal fluid (UBERON:0001359) PubMed (8857741)
blood (UBERON:0000178) PubMed (7657478)
breast milk (ENVO:02000031) PubMed (2388136)
- DOI (10.1038/nbt.2488)
Mus musculus (ncbitaxon:10090) - MetaboLights (MTBLS345) From MetaboLights
Roles Classification
Chemical Roles:
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
food antioxidant  An antioxidant that used as a food additives to help guard against food deterioration.
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
antioxidant  A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:
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).
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.
immunomodulator  Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
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.
plant metabolite  Any eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
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.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
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.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
Applications:
anticoagulant  An agent that prevents blood clotting.
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.
immunomodulator  Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
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.
food antioxidant  An antioxidant that used as a food additives to help guard against food deterioration.
hypoglycemic agent  A drug which lowers the blood glucose level.
antirheumatic drug  A drug used to treat rheumatoid arthritis.
antiatherosclerotic agent  A cardiovascular drug that prevents atherosclerosis (a disease in which the inside of an artery narrows due to the build up of plaque). Compare with antiatherogenic agent.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
antiglaucoma drug  Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
antidote  Any protective agent counteracting or neutralizing the action of poisons.
renoprotective agent  Any compound that is able to prevent damage to the kidneys.
antipsoriatic  A drug used to treat psoriasis.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
antifibrotic agent  Any agent which acts to reduce fibrosis.
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
anti-anaemic agent  A compound which increases either the number of red cells or the amount of haemoglobin in the blood.
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
vulnerary  A drug used in treating and healing of wounds.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
anti-asthmatic agent  Any compound that has anti-asthmatic effects.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
ophthalmology drug  Any compound used for the treatment of eye conditions or eye diseases.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
hypoglycemic agent  A drug which lowers the blood glucose level.
antirheumatic drug  A drug used to treat rheumatoid arthritis.
antiatherosclerotic agent  A cardiovascular drug that prevents atherosclerosis (a disease in which the inside of an artery narrows due to the build up of plaque). Compare with antiatherogenic agent.
antidepressant  Antidepressants are mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions.
antiglaucoma drug  Any drug which can be used to prevent or alleviate glaucoma, a disease in which the optic nerve is damaged, resulting in progressive, irreversible loss of vision. It is often, though not always, associated with increased pressure of the fluid in the eye.
antidote  Any protective agent counteracting or neutralizing the action of poisons.
renoprotective agent  Any compound that is able to prevent damage to the kidneys.
antipsoriatic  A drug used to treat psoriasis.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
antipsychotic agent  Antipsychotic drugs are agents that control agitated psychotic behaviour, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect.
antifibrotic agent  Any agent which acts to reduce fibrosis.
antiparkinson drug  A drug used in the treatment of Parkinson's disease.
antiinfective agent  A substance used in the prophylaxis or therapy of infectious diseases.
anti-anaemic agent  A compound which increases either the number of red cells or the amount of haemoglobin in the blood.
hepatoprotective agent  Any compound that is able to prevent damage to the liver.
vulnerary  A drug used in treating and healing of wounds.
anti-inflammatory agent  Any compound that has anti-inflammatory effects.
anti-asthmatic agent  Any compound that has anti-asthmatic effects.
cardiovascular drug  A drug that affects the rate or intensity of cardiac contraction, blood vessel diameter or blood volume.
ophthalmology drug  Any compound used for the treatment of eye conditions or eye diseases.
analgesic  An agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
ChEBI Ontology
Outgoing Relation(s)
(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 Relation(s)
13-hydroxy-α-tocopherol (CHEBI:84962) has functional parent (R,R,R)-α-tocopherol (CHEBI:18145)
α-tocopheryloxyacetic acid (CHEBI:194185) 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  Source
(2R)-2,5,7,8-tetramethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-olIUPAC
(2R,4'R,8'R)-alpha-tocopherolChemIDplus
(2R,4'R,8'R)-α-tocopherolChemIDplus
(2R)-2,5,7,8-TETRAMETHYL-2-[(4R,8R)-4,8,12-TRIMETHYLTRIDECYL]CHROMAN-6-OLPDBeChem
5,7,8-trimethyltocolChemIDplus
(+)-alpha-tocopherolChemIDplus
UniProt Name  Source
(+)-α-tocopherolUniProt
Manual XrefsDatabases
14265ChemSpider
4280DrugCentral
Alpha-TocopherolWikipedia
ALPHA-TOCOPHEROLMetaCyc
C00007366KNApSAcK
C02477KEGG COMPOUND
DB00163DrugBank
FDB000565FooDB
HMDB0001893HMDB
LMPR02020001LIPID MAPS
VIVPDBeChem
Registry NumbersSources
Beilstein:5300493Beilstein
Reaxys:94012Reaxys
CAS:59-02-9KEGG COMPOUND
CAS:59-02-9ChemIDplus
CAS:59-02-9NIST Chemistry WebBook
Citations