beta-Tocotrienol

Details

• Internal ID: e4950e98-68c6-4f8d-a24c-c80802b11631
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Quinone and hydroquinone lipids > Vitamin E compounds > Tocotrienols
• IUPAC Name: (2R)-2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
• SMILES (Canonical): CC1=CC(=C(C2=C1OC(CC2)(C)CCC=C(C)CCC=C(C)CCC=C(C)C)C)O
• SMILES (Isomeric): CC1=CC(=C(C2=C1O[C@](CC2)(C)CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)C)O
• InChI: InChI=1S/C28H42O2/c1-20(2)11-8-12-21(3)13-9-14-22(4)15-10-17-28(7)18-16-25-24(6)26(29)19-23(5)27(25)30-28/h11,13,15,19,29H,8-10,12,14,16-18H2,1-7H3/b21-13+,22-15+/t28-/m1/s1
• InChI Key: FGYKUFVNYVMTAM-WAZJVIJMSA-N
• Popularity: 23 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₂O₂
• Molecular Weight: 410.60 g/mol
• Exact Mass: 410.318480578 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 8.90
• Atomic LogP (AlogP): 8.29
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• 490-23-3
• epsilon-Tocopherol
• Tocotrienol, beta
• a-tocotrienol
• D-beta-Tocotrienol
• .epsilon.-Tocopherol
• UNII-CHH810ZM8C
• CHH810ZM8C
• EINECS 207-708-0
• (2R)-2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
• 2,5,8-Trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
• (2R)-3,4-dihydro-2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-2H-1-benzopyran-6-ol
• 3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyl-trideca-3,7,11-trienyl)-2H-1-benzopyran-6-ol
• epsilon-Tokoferol
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-((3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl)-, (2R)-
• 2H-1-benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)-
• 2R,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol
• beta -Tocotrienol
• 2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,5,8-TRIMETHYL-2-(4,8,12-TRIMETHYL-3,7,11-TRIDECATRIENYL)-, (R-(E,E))-
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, [R-(E,E)]-
• D-beta- Tocotrienol
• .BETA.-TOCOTRIENOL
• .EPSILON.-TOKOFEROL
• Tocotrienol, 5,8-dimethyl
• BIDD:PXR0058
• SCHEMBL66599
• D-.BETA.-TOCOTRIENOL
• 2,5,8-trimethyl-2-(4,8,12-trimethyltrideca-3,7,11-trienyl)chroman-6-ol
• SCHEMBL16430159
• CHEBI:33275
• .BETA.-TOCOTRIENOL [MI]
• DTXSID50883401
• BETA-TOCOTRIENOL [WHO-DD]
• beta-Tocotrienol, analytical standard
• LMPR02020055
• AKOS040744870
• [R-(E,E)]-3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol
• J37.066E
• MS-27089
• HY-108693
• CS-0029986
• A934798
• Q171542
• 6-Chromanol,2,5,8-trimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)- (8CI)
• (2R)-2,5,8-Trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatr ien-1-yl]-6-chromanol
• (2R)-2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol
• (2R)-2beta,5,8-Trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-3,4-dihydro-2H-1-benzopyran-6-ol
• 2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,5,8-TRIMETHYL-2- ((3E,7E)-4,8,12-TRIMETHYL-3,7,11-TRIDECATRIEN-1-YL)-, (2R)-
• 2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,5,8-TRIMETHYL-2- ((3E,7E)-4,8,12-TRIMETHYL-3,7,11-TRIDECATRIENYL)-, (2R)-
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-((3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl)-, (2R)-
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9939	99.39%
Caco-2	+	0.7042	70.42%
Blood Brain Barrier	+	0.8000	80.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.6797	67.97%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.8853	88.53%
OATP1B3 inhibitior	+	0.9495	94.95%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.8942	89.42%
P-glycoprotein inhibitior	+	0.7399	73.99%
P-glycoprotein substrate	-	0.8179	81.79%
CYP3A4 substrate	+	0.6128	61.28%
CYP2C9 substrate	-	0.6075	60.75%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.6009	60.09%
CYP2C9 inhibition	-	0.8057	80.57%
CYP2C19 inhibition	-	0.5186	51.86%
CYP2D6 inhibition	-	0.8749	87.49%
CYP1A2 inhibition	-	0.5797	57.97%
CYP2C8 inhibition	+	0.5000	50.00%
CYP inhibitory promiscuity	+	0.5983	59.83%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8900	89.00%
Carcinogenicity (trinary)	Non-required	0.7218	72.18%
Eye corrosion	-	0.9919	99.19%
Eye irritation	-	0.8656	86.56%
Skin irritation	-	0.6906	69.06%
Skin corrosion	-	0.9423	94.23%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8933	89.33%
Micronuclear	-	0.9600	96.00%
Hepatotoxicity	-	0.6226	62.26%
skin sensitisation	-	0.6207	62.07%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.8250	82.50%
Nephrotoxicity	-	0.7595	75.95%
Acute Oral Toxicity (c)	III	0.7055	70.55%
Estrogen receptor binding	+	0.7430	74.30%
Androgen receptor binding	+	0.6304	63.04%
Thyroid receptor binding	+	0.7408	74.08%
Glucocorticoid receptor binding	+	0.6598	65.98%
Aromatase binding	+	0.7517	75.17%
PPAR gamma	+	0.8075	80.75%
Honey bee toxicity	-	0.8757	87.57%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9900	99.00%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.48%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	95.59%	93.40%
CHEMBL3401	O75469	Pregnane X receptor	93.34%	94.73%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	92.05%	92.08%
CHEMBL2581	P07339	Cathepsin D	90.26%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.52%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.48%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	85.42%	86.33%
CHEMBL4208	P20618	Proteasome component C5	84.45%	90.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.54%	89.00%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	81.47%	91.79%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	80.83%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	80.47%	93.10%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.22%	92.94%
CHEMBL233	P35372	Mu opioid receptor	80.01%	97.93%

Plants that contains it

• Amaranthus hypochondriacus
• Hippophae rhamnoides
• Oryza sativa

Cross-Links

• PubChem: 5282348
• NPASS: NPC129707
• LOTUS: LTS0181074
• wikiData: Q171542