delta-Tocotrienol

Details

• Internal ID: 5b75cf7b-918b-4b6f-9802-ab7e7b9c068e
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Quinone and hydroquinone lipids > Vitamin E compounds > Tocotrienols
• IUPAC Name: (2R)-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
• SMILES (Canonical): CC1=CC(=CC2=C1OC(CC2)(C)CCC=C(C)CCC=C(C)CCC=C(C)C)O
• SMILES (Isomeric): CC1=CC(=CC2=C1O[C@](CC2)(C)CC/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)O
• InChI: InChI=1S/C27H40O2/c1-20(2)10-7-11-21(3)12-8-13-22(4)14-9-16-27(6)17-15-24-19-25(28)18-23(5)26(24)29-27/h10,12,14,18-19,28H,7-9,11,13,15-17H2,1-6H3/b21-12+,22-14+/t27-/m1/s1
• InChI Key: ODADKLYLWWCHNB-LDYBVBFYSA-N
• Popularity: 502 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₄₀O₂
• Molecular Weight: 396.60 g/mol
• Exact Mass: 396.302830514 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 8.60
• Atomic LogP (AlogP): 7.98
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 9

Synonyms

• 25612-59-3
• Tocotrienol, delta
• 8-Methyltocotrienol
• .delta.-Tocotrienol
• (R)-delta-Tocotrienol
• UNII-1SRB74OWSI
• 1SRB74OWSI
• (R)-.delta.-Tocotrienol
• D-DELTA-TOCOTRIENOL
• (2R)-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trienyl]-3,4-dihydrochromen-6-ol
• CHEBI:33276
• (R)-2,8-Dimethyl-2-((3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl)chroman-6-ol
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, (R-(E,E))-
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-, [R-(E,E)]-
• 2H-1-benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)-
• 2R,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol
• Delta-tocotrienols
• delta -Tocotrienol
• 2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,8-DIMETHYL-2-((3E,7E)-4,8,12-TRIMETHYL-3,7,11-TRIDECATRIEN-1-YL)-, (2R)-
• 2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,8-DIMETHYL-2-((3E,7E)-4,8,12-TRIMETHYL-3,7,11-TRIDECATRIENYL)-, (2R)-
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrien-1-yl]-, (2R)-
• R-delta-tocotrienol
• BIDD:PXR0041
• CHEMBL121305
• SCHEMBL8408117
• SCHEMBL16430161
• DTXSID30180288
• HMS3650C18
• DELTA TOCOTRIENOL [WHO-DD]
• LMPR02020056
• delta-Tocotrienol, analytical standard
• AKOS040760094
• NCGC00253541-03
• AS-82630
• J17.358D
• HY-122778
• CS-0089253
• SR-01000946270
• SR-01000946270-1
• Q27104272
• 2,8-Dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-6-chromanol
• 6-Chromanol, 2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-
• 6-Chromanol, 2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)- (7CI,8CI)
• (2R)-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyltrideca-3,7,11-trien-1-yl]-3,4-dihydro-2H-chromen-6-ol
• (R-(E,E))-3,4-Dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,8-dimethyl-2-[(3E,7E)-4,8,12-trimethyl-3,7,11-tridecatrienyl]-, (2R)- (9CI)
• 3,4-Dihydro-2,8-dimethyl-2-(4,8,12-trimethyl-3,7,11-tridecatrienyl)-2H-1-benzopyran-6-ol, 9CI

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9941	99.41%
Caco-2	+	0.7554	75.54%
Blood Brain Barrier	+	0.8250	82.50%
Human oral bioavailability	-	0.6857	68.57%
Subcellular localzation	Mitochondria	0.6431	64.31%
OATP2B1 inhibitior	-	0.8598	85.98%
OATP1B1 inhibitior	+	0.8632	86.32%
OATP1B3 inhibitior	+	0.9514	95.14%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9120	91.20%
P-glycoprotein inhibitior	+	0.7996	79.96%
P-glycoprotein substrate	-	0.7605	76.05%
CYP3A4 substrate	+	0.6401	64.01%
CYP2C9 substrate	-	0.6075	60.75%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.6690	66.90%
CYP2C9 inhibition	-	0.7438	74.38%
CYP2C19 inhibition	+	0.5768	57.68%
CYP2D6 inhibition	-	0.8376	83.76%
CYP1A2 inhibition	-	0.5830	58.30%
CYP2C8 inhibition	+	0.5952	59.52%
CYP inhibitory promiscuity	+	0.5493	54.93%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.7240	72.40%
Eye corrosion	-	0.9898	98.98%
Eye irritation	-	0.8994	89.94%
Skin irritation	-	0.7133	71.33%
Skin corrosion	-	0.9432	94.32%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.9481	94.81%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.5476	54.76%
skin sensitisation	-	0.5819	58.19%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.8125	81.25%
Nephrotoxicity	-	0.7030	70.30%
Acute Oral Toxicity (c)	III	0.7658	76.58%
Estrogen receptor binding	+	0.7768	77.68%
Androgen receptor binding	+	0.5481	54.81%
Thyroid receptor binding	+	0.7219	72.19%
Glucocorticoid receptor binding	+	0.5670	56.70%
Aromatase binding	+	0.6589	65.89%
PPAR gamma	+	0.8189	81.89%
Honey bee toxicity	-	0.8555	85.55%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	+	0.7200	72.00%
Fish aquatic toxicity	+	0.9824	98.24%

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	99.12%	91.11%
CHEMBL3401	O75469	Pregnane X receptor	96.76%	94.73%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.34%	94.45%
CHEMBL4769	O95749	Geranylgeranyl pyrophosphate synthetase	91.18%	92.08%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.18%	86.33%
CHEMBL233	P35372	Mu opioid receptor	89.75%	97.93%
CHEMBL2581	P07339	Cathepsin D	88.93%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.72%	96.09%
CHEMBL2107	P61073	C-X-C chemokine receptor type 4	86.31%	93.10%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.78%	95.56%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	81.86%	85.00%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	81.12%	93.40%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.01%	100.00%

Plants that contains it

• Amaranthus cruentus
• Bixa orellana
• Cinnamosma fragrans
• Cinnamosma macrocarpa
• Cinnamosma madagascariensis
• Cratoxylum cochinchinense
• Cratoxylum sumatranum
• Garcinia kola
• Garcinia multiflora
• Garcinia virgata
• Kielmeyera coriacea
• Kielmeyera lathrophyton
• Kielmeyera reticulata
• Oryza sativa
• Pleodendron costaricense
• Sesamum indicum

Cross-Links

• PubChem: 5282350
• NPASS: NPC69539
• ChEMBL: CHEMBL121305
• LOTUS: LTS0255585
• wikiData: Q27104272