MiMeDB: Showing metabocard for alpha-Tocotrienol (MMDBc0000255)

Xenobiotic

Record Information

Version

2.0

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

Not Available

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

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Not Available

Spectra

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-23	418.4
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	41.5
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	990.4
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	1305.1
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	1386.0
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	842.1
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	3820.2
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	101.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	421.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1146.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (void)	2025-10-23	702.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	436.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	359.8
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (void)	2025-10-23	9.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	345.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	321.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	578.7
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	2101.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	2609.9

Retention Indices

Chromatography Type	Peak Label	SMILES	Stationary Phase	Deposition Date	Retention Index
Gas Chromatography	alpha-Tocotrienol_TMS_1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC[C@]1(C)CCC2=C(C)C(O[Si](C)(C)C)=C(C)C(C)=C2O1	standard non polar	2025-10-23	2068.61
Gas Chromatography	alpha-Tocotrienol_TMS_1	CC(C)=CCC/C(C)=C/CC/C(C)=C/CC[C@]1(C)CCC2=C(C)C(O[Si](C)(C)C)=C(C)C(C)=C2O1	standard polar	2025-10-23	1637.52

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

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/Eubacteria	Firmicutes	1	Human ; Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Bacteroidetes	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox

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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

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:0x00005624ca60f5c8>

3D MOL for #<Metabolite:0x00005624ca60f5c8>

3D SDF for #<Metabolite:0x00005624ca60f5c8>

3D-SDF for #<Metabolite:0x00005624ca60f5c8>

PDB for #<Metabolite:0x00005624ca60f5c8>

3D PDB for #<Metabolite:0x00005624ca60f5c8>

SMILES for #<Metabolite:0x00005624ca60f5c8>

INCHI for #<Metabolite:0x00005624ca60f5c8>

Structure for #<Metabolite:0x00005624ca60f5c8>

3D Structure for #<Metabolite:0x00005624ca60f5c8>