2-(3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione

Details

• Internal ID: c910ff41-9b36-431d-8a21-ef997cebe670
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Diterpenoids
• IUPAC Name: 2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
• SMILES (Canonical): CC1=C(C(=O)C(=C(C1=O)C)CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)O)C
• SMILES (Isomeric): CC1=C(C(=O)C(=C(C1=O)C)CCC(C)(CCCC(C)CCCC(C)CCCC(C)C)O)C
• InChI: InChI=1S/C29H50O3/c1-20(2)12-9-13-21(3)14-10-15-22(4)16-11-18-29(8,32)19-17-26-25(7)27(30)23(5)24(6)28(26)31/h20-22,32H,9-19H2,1-8H3
• InChI Key: LTVDFSLWFKLJDQ-UHFFFAOYSA-N
• Popularity: 150 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₅₀O₃
• Molecular Weight: 446.70 g/mol
• Exact Mass: 446.37599545 g/mol
• Topological Polar Surface Area (TPSA): 54.40 Ų
• XlogP: 8.80
• Atomic LogP (AlogP): 7.76
• H-Bond Acceptor: 3
• H-Bond Donor: 1
• Rotatable Bonds: 15

Synonyms

• Eutrophyl
• alpha-tocopherolquinone
• alpha-tocopheryl quinone
• alpha-Tocopheroquinone
• alpha-Tocopherol quinone
• 2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethylcyclohexa-2,5-diene-1,4-dione
• Tocopherylquinone, d-alpha
• Tensiopress
• Vitapressina
• Ipotensil
• Metorena
• Trimina
• a-Tocoquinone
• tocopherolquinone
• EINECS 231-450-8
• a-Tocopherolquinone
• a-Tocopheryl quinone
• AI3-51910
• D--Tocopherol Quinone
• A-0001
• d-.alpha.-Tocoquinone
• .alpha.-Tocopherolquinone
• TOCOQUINONE, ALPHA
• (+)-.alpha.-Tocoquinone
• SCHEMBL1186492
• CHEMBL1254448
• DTXSID30864091
• 2-(3-Hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethyl-p-benzoquinone
• LTVDFSLWFKLJDQ-UHFFFAOYSA-N
• p-Benzoquinone, 2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethyl-
• 2,5-Cyclohexadiene-1,4-dione, 2-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-3,5,6-trimethyl-, (3R-(3R*,7R*,11R*))-
• ATQ
• NSC20810
• NSC-20810
• AKOS025293924
• LS-40363
• LS-40364
• 3-Chloro-2-hydroxypropyltrimethylammoniumchloride
• 2 (3-hydroxy-3,7,11,15-tetramethylhexadecyl)- 3,5,6-trimethyl-1,4-benzoquinone
• 2,5,6-Trimethyl-3-(3-hydroxy-3,7,11,15-tetramethylhexadecyl)-1,4-benzoquinone
• 2-(3-Hydroxy-3,11,15-tetramethyl-hexadecyl)- 3,5,6-trimethyl-[1,4]benzoquinone
• 2-(3-hydroxy-3,7,11,15-tetramethyl-hexadecyl)-3,5,6-trimethyl-2,5 cyclo-hexadiene-1,4-dione

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9952	99.52%
Caco-2	-	0.5319	53.19%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.6857	68.57%
Subcellular localzation	Mitochondria	0.8848	88.48%
OATP2B1 inhibitior	-	0.7173	71.73%
OATP1B1 inhibitior	+	0.9342	93.42%
OATP1B3 inhibitior	+	0.9591	95.91%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.5250	52.50%
BSEP inhibitior	+	0.7946	79.46%
P-glycoprotein inhibitior	-	0.5730	57.30%
P-glycoprotein substrate	-	0.7332	73.32%
CYP3A4 substrate	+	0.5251	52.51%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8639	86.39%
CYP3A4 inhibition	-	0.6646	66.46%
CYP2C9 inhibition	-	0.8274	82.74%
CYP2C19 inhibition	-	0.8476	84.76%
CYP2D6 inhibition	-	0.9099	90.99%
CYP1A2 inhibition	-	0.9417	94.17%
CYP2C8 inhibition	-	0.9298	92.98%
CYP inhibitory promiscuity	-	0.9100	91.00%
UGT catelyzed	-	0.8000	80.00%
Carcinogenicity (binary)	-	0.9028	90.28%
Carcinogenicity (trinary)	Non-required	0.6392	63.92%
Eye corrosion	-	0.9854	98.54%
Eye irritation	-	0.8289	82.89%
Skin irritation	+	0.5744	57.44%
Skin corrosion	-	0.9725	97.25%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7477	74.77%
Micronuclear	-	0.9300	93.00%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	+	0.6901	69.01%
Respiratory toxicity	+	0.6667	66.67%
Reproductive toxicity	+	0.6111	61.11%
Mitochondrial toxicity	-	0.5125	51.25%
Nephrotoxicity	-	0.7160	71.60%
Acute Oral Toxicity (c)	III	0.5897	58.97%
Estrogen receptor binding	+	0.7027	70.27%
Androgen receptor binding	+	0.7162	71.62%
Thyroid receptor binding	+	0.5277	52.77%
Glucocorticoid receptor binding	+	0.6054	60.54%
Aromatase binding	-	0.4844	48.44%
PPAR gamma	+	0.5540	55.40%
Honey bee toxicity	-	0.9570	95.70%
Biodegradation	-	0.7000	70.00%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.9873	98.73%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.81%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	92.10%	94.73%
CHEMBL1907	P15144	Aminopeptidase N	91.80%	93.31%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	89.62%	90.71%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.03%	95.56%
CHEMBL3359	P21462	Formyl peptide receptor 1	87.79%	93.56%
CHEMBL3130	O00329	PI3-kinase p110-delta subunit	87.79%	96.47%
CHEMBL253	P34972	Cannabinoid CB2 receptor	86.30%	97.25%
CHEMBL2265	P23141	Acyl coenzyme A:cholesterol acyltransferase	85.98%	85.94%
CHEMBL1907591	P30926	Neuronal acetylcholine receptor; alpha4/beta4	83.69%	100.00%
CHEMBL1293267	Q9HC97	G-protein coupled receptor 35	83.19%	89.34%
CHEMBL4581	P52732	Kinesin-like protein 1	81.20%	93.18%
CHEMBL2274	Q9H228	Sphingosine 1-phosphate receptor Edg-8	80.70%	100.00%
CHEMBL5163	Q9NY46	Sodium channel protein type III alpha subunit	80.10%	96.90%

Plants that contains it

• Beilschmiedia erithrophloia
• Beilschmiedia tsangii
• Bidens pilosa
• Cryptocarya chinensis
• Cullen plicatum
• Fatoua villosa
• Garcinia linii
• Garcinia multiflora
• Garcinia paucinervis
• Himalaiella deltoidea
• Ixora coccinea
• Litsea acutivena
• Muntingia calabura
• Myriactis humilis
• Nepeta tuberosa
• Parentucellia latifolia
• Photinia lucida
• Selaginella delicatula
• Swertia angustifolia
• Synsepalum dulcificum
• Vitex negundo var. cannabifolia
• Zanthoxylum beecheyanum

Cross-Links

• PubChem: 24205
• NPASS: NPC67301
• LOTUS: LTS0107241
• wikiData: Q105157204