MiMeDB: Showing metabocard for alpha-Tocotrienol (MMDBc0000255)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-10-27 23:41:31 UTC

Update Date

2024-10-06 22:32:41 UTC

Metabolite ID

MMDBc0000255

Metabolite Identification

Common Name

alpha-Tocotrienol

Description

alpha-Tocotrienol (CAS: 1721-51-3), also known as 5,7,8-trimethyltocotrienol, belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. They differ from tocopherols that contain a saturated trimethyltridecyl chain. Thus, alpha-tocotrienol is considered to be a quinone lipid molecule. alpha-Tocotrienol is found in the blood plasma and all lipoprotein subfractions. Compared to tocopherols, alpha-tocotrienols are poorly studied. Its presence in the blood plasma at nanomolar concentrations is thought to help to prevent stroke-related neurodegeneration (PMID: 16771695 ). alpha-Tocotrienol has been found to have vitamin E activity.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(2R)-2,5,7,8-Tetramethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-1-benzopyran-6-ol	ChEBI
zeta1-Tocopherol	ChEBI
Ζ1-tocopherol	Generator
a-Tocotrienol	Generator
Α-tocotrienol	Generator
(2R,3'e,7'e)-alpha-Tocotrienol	HMDB
(R)-alpha-Tocotrienol	HMDB
Tocotrienol, alpha	HMDB
(2R,3'e,7'e)-Α-tocotrienol	HMDB
(2R,3’E,7’e)-α-tocotrienol	HMDB
(R)-Α-tocotrienol	HMDB
5,7,8-Trimethyltocotrienol	HMDB
alpha-Tocotrienol	HMDB

Molecular Formula

C₂₉H₄₄O₂

Average Mass

424.6585

Monoisotopic Mass

424.334130652

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

58864-81-6

SMILES

Not Available

InChI Identifier

InChI=1S/C29H44O2/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/h12,14,16,30H,9-11,13,15,17-19H2,1-8H3/b21-14+,22-16+/t29-/m1/s1

InChI Key

RZFHLOLGZPDCHJ-XZXLULOTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tocotrienols. These are vitamin E derivatives containing an unsaturated trimethyltrideca-3,7,11-trien-1-yl chain attached to the carbon C6 atom of a benzopyran ring system. The differ from tocopherols that contain a saturated trimethyltridecyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Quinone and hydroquinone lipids

Direct Parent

Tocotrienols

Alternative Parents

Substituents

Tocotrienol
Diterpenoid
1-benzopyran
Benzopyran
Chromane
Alkyl aryl ether
Benzenoid
Oxacycle
Organoheterocyclic compound
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tocotrienol (CHEBI:33270 )
vitamin E (CHEBI:33270 )
vitamin E (C14153 )
Vitamin E (LMPR02020054 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0004385	Ascorbic acid	alpha-Tocotrienol	Not Available	VMH	11160563
MMDBr0004825	alpha-Tocotrienol	13'-Hydroxy-alpha-tocotrienol	Not Available	VMH	10191290 11997390 12368403
MMDBr0004826	alpha-Tocotrienol	13'-Hydroxy-alpha-tocotrienol	cytochrome P450, family 4, subfamily F, polypeptide 2	VMH	10191290 11997390 12368403

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Firmicutes	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Bacteroidetes	1	Human feces; Human stool	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	4.23	0.7	uM	Adult (>18 years old)	Both	Normal	HMDB	12739983
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0006327

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

METLIN ID

Not Available

PubChem Compound

5282347

PDB ID

Not Available

ChEBI ID

33270

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Khosla P, Patel V, Whinter JM, Khanna S, Rakhkovskaya M, Roy S, Sen CK: Postprandial levels of the natural vitamin E tocotrienol in human circulation. Antioxid Redox Signal. 2006 May-Jun;8(5-6):1059-68. doi: 10.1089/ars.2006.8.1059. [PubMed:16771695 ]

Showing metabocard for alpha-Tocotrienol (MMDBc0000255)

MOL for #<Metabolite:0x0000559d05128750>

3D MOL for #<Metabolite:0x0000559d05128750>

3D SDF for #<Metabolite:0x0000559d05128750>

3D-SDF for #<Metabolite:0x0000559d05128750>

PDB for #<Metabolite:0x0000559d05128750>

3D PDB for #<Metabolite:0x0000559d05128750>

SMILES for #<Metabolite:0x0000559d05128750>

INCHI for #<Metabolite:0x0000559d05128750>

Structure for #<Metabolite:0x0000559d05128750>

3D Structure for #<Metabolite:0x0000559d05128750>