beta-Tocopherol

Details

• Internal ID: d9eb07e4-f762-40a9-9ccf-1c39c2c239f2
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Quinone and hydroquinone lipids > Vitamin E compounds > Tocopherols
• IUPAC Name: (2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
• SMILES (Canonical): CC1=CC(=C(C2=C1OC(CC2)(C)CCCC(C)CCCC(C)CCCC(C)C)C)O
• SMILES (Isomeric): CC1=CC(=C(C2=C1O[C@](CC2)(C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)C)O
• InChI: InChI=1S/C28H48O2/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/h19-22,29H,8-18H2,1-7H3/t21-,22-,28-/m1/s1
• InChI Key: WGVKWNUPNGFDFJ-DQCZWYHMSA-N
• Popularity: 98 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₄₈O₂
• Molecular Weight: 416.70 g/mol
• Exact Mass: 416.365430770 g/mol
• Topological Polar Surface Area (TPSA): 29.50 Ų
• XlogP: 10.30
• Atomic LogP (AlogP): 8.53
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 12

Synonyms

• 16698-35-4
• d-beta-Tocopherol
• 148-03-8
• Cumotocopherol
• beta Tocopherol
• p-Xylotocopherol
• (R)-2,5,8-Trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-ol
• .beta.-Tocopherol
• 5,8-Dimethyltocol
• beta-D-Tocopherol
• Neotocopherol
• UNII-8K9365K9PX
• (2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydrochromen-6-ol
• 8K9365K9PX
• UNII-9U6A490501
• EINECS 205-708-5
• EINECS 240-747-1
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-
• 9U6A490501
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-
• (+)-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-6-chromanol
• DL-beta-Tocopherol
• rel-(R)-2,5,8-Trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)chroman-6-ol
• 3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
• (2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-1-benzopyran-6-ol
• (2R)-3,4-dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-2H-1-benzopyran-6-ol
• [2R[2R*(4R*,8R*)]]-3,4-dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-((4R,8R)-4,8,12-trimethyltridecyl)-, (2R)-rel-
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-, (2R)-rel-
• C28H48O2
• (2R)-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)chroman-6-ol
• beta -Tocopherol
• D-b-Tocopherol
• -Tocopherol-d3
• Tocopherol, beta-
• (2R(2R*(4R*,8R*)))-3,4-Dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
• (2R)-3,4-DIHYDRO-2,5,8-TRIMETHYL-2-((4R,8R)-4,8,12-TRIMETHYLTRIDECYL)-2H-1-BENZOPYRAN-6-OL
• (+/-)-beta-Tocopherol
• DL-BETA TOCOPHEROL
• (R,R,R)-beta-Tocopherol
• D-.BETA.-TOCOPHEROL
• BIDD:PXR0140
• SCHEMBL39202
• DL-.BETA.-TOCOPHEROL
• 6-Chromanol, 2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-
• RRR-.BETA.-TOCOPHEROL
• rac- beta -Tocopherol solution
• .BETA.-TOCOPHEROL [MI]
• .BETA.-TOCOPHEROL, DL-
• CHEBI:47771
• BETA TOCOPHEROL [WHO-DD]
• DTXSID10873424
• DTXSID30884931
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl- 2-(4,8,12-trimethyltridecyl)-
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-
• 48223-98-9
• VITAMIN E (BETA TOCOTRIENOL)
• AKOS022171754
• AS-74577
• HY-133680
• J236.825K
• CS-0128997
• J1.282.204I
• J1.604.281A
• E76237
• Q155667
• J-010328
• RRR-.ALPHA.-TOCOPHEROL IMPURITY B [EP IMPURITY]
• FA7BA838-41F9-4B85-947D-F3A920942587
• (2R)-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltridecyl]-3,4-dihydro-2H-chromen-6-ol
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-, ()-
• (2R)-3,4-Dihydro-2,5,8-trimethyl-2-[(4R,8R)-4,8,12-trimethyltri-decyl]-2H-1-benzopyran-6-ol
• ?[2R[2R*(4R*,8R*)]]-3,4-dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-2H-benzopyran-6-ol
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl- 2-(4,8,12-trimethyltridecyl)-, [2R-[2R(4R,8R)]]-
• 2H-1-BENZOPYRAN-6-OL, 3,4-DIHYDRO-2,5,8-TRIMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL)-, (2R*(4R*,8R*))- 6-CHROMANOL, 2,5,8-TRIMETHYL-2-(4,8,12-TRIMETHYLTRIDECYL)-
• 2H-1-Benzopyran-6-ol, 3,4-dihydro-2,5,8-trimethyl-2-(4,8,12-trimethyltridecyl)-, [2R-[2R*(4R*,8R*)]]-
• RAC-(2R*)-3,4-DIHYDRO-2,5,8-TRIMETHYL-2-((4R*,8R*)-4,8,12-TRIMETHYLTRIDECYL)-2H-1-BENZOPYRAN-6-OL
• REL-(2R*)-2,5,8-TRIMETHYL-2-((4R*,8R*)-4,8,12-TRIMETHYLTRIDECYL)-3,4-DIHYDRO-2H-1-BENZOPYRAN-6-OL

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9915	99.15%
Caco-2	+	0.6649	66.49%
Blood Brain Barrier	+	0.9500	95.00%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7187	71.87%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.9361	93.61%
OATP1B3 inhibitior	+	0.9480	94.80%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.8000	80.00%
BSEP inhibitior	+	0.6487	64.87%
P-glycoprotein inhibitior	-	0.7935	79.35%
P-glycoprotein substrate	-	0.6654	66.54%
CYP3A4 substrate	+	0.5872	58.72%
CYP2C9 substrate	-	0.5955	59.55%
CYP2D6 substrate	+	0.5342	53.42%
CYP3A4 inhibition	-	0.8309	83.09%
CYP2C9 inhibition	-	0.9071	90.71%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	-	0.8122	81.22%
CYP2C8 inhibition	-	0.5992	59.92%
CYP inhibitory promiscuity	-	0.7762	77.62%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.7474	74.74%
Eye corrosion	-	0.9814	98.14%
Eye irritation	-	0.9480	94.80%
Skin irritation	-	0.7350	73.50%
Skin corrosion	-	0.9249	92.49%
Ames mutagenesis	-	0.8500	85.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6941	69.41%
Micronuclear	-	0.9700	97.00%
Hepatotoxicity	-	0.6226	62.26%
skin sensitisation	-	0.7470	74.70%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6778	67.78%
Mitochondrial toxicity	+	0.8375	83.75%
Nephrotoxicity	-	0.9277	92.77%
Acute Oral Toxicity (c)	III	0.7164	71.64%
Estrogen receptor binding	+	0.7514	75.14%
Androgen receptor binding	+	0.6951	69.51%
Thyroid receptor binding	+	0.6565	65.65%
Glucocorticoid receptor binding	+	0.6442	64.42%
Aromatase binding	+	0.6788	67.88%
PPAR gamma	+	0.7253	72.53%
Honey bee toxicity	-	0.9443	94.43%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5000	50.00%
Fish aquatic toxicity	+	0.9671	96.71%

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	99.27%	91.11%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	96.79%	93.40%
CHEMBL2581	P07339	Cathepsin D	92.59%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.06%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	89.81%	94.73%
CHEMBL3902	P09211	Glutathione S-transferase Pi	89.08%	93.81%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	88.18%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.50%	95.56%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	86.17%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.47%	99.15%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.44%	93.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	82.95%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	81.91%	86.33%
CHEMBL1907	P15144	Aminopeptidase N	81.54%	93.31%
CHEMBL1951	P21397	Monoamine oxidase A	81.45%	91.49%
CHEMBL4208	P20618	Proteasome component C5	80.98%	90.00%

Plants that contains it

• Alsophila podophylla
• Campanula medium
• Capsicum annuum
• Caryodendron orinocense
• Crataegus monogyna
• Cupania latifolia
• Glycine max
• Juglans regia
• Origanum vulgare
• Oryza sativa
• Psophocarpus tetragonolobus
• Raphanus raphanistrum subsp. sativus
• Rosmarinus officinalis
• Schisandra chinensis
• Spinacia oleracea

Cross-Links

• PubChem: 6857447
• NPASS: NPC128410
• LOTUS: LTS0152412
• wikiData: Q155667