Pterostilbene

Details

Physical and Chemical Properties

Synonyms

2D Structure

3D Structure

ADMET Properties

Targets (proven and/or predicted)

Plants that contains it

Cross-Links

Details

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Internal ID	1066b6b4-96ce-479c-add2-f4afde2237d4
Taxonomy	Phenylpropanoids and polyketides > Stilbenes
IUPAC Name	4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol
SMILES (Canonical)	COC1=CC(=CC(=C1)C=CC2=CC=C(C=C2)O)OC
SMILES (Isomeric)	COC1=CC(=CC(=C1)/C=C/C2=CC=C(C=C2)O)OC
InChI	InChI=1S/C16H16O3/c1-18-15-9-13(10-16(11-15)19-2)4-3-12-5-7-14(17)8-6-12/h3-11,17H,1-2H3/b4-3+
InChI Key	VLEUZFDZJKSGMX-ONEGZZNKSA-N
Popularity	1,113 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₆H₁₆O₃
Molecular Weight	256.30 g/mol
Exact Mass	256.109944368 g/mol
Topological Polar Surface Area (TPSA)	38.70 Å²
XlogP	3.80
Atomic LogP (AlogP)	3.58
H-Bond Acceptor	3
H-Bond Donor	1
Rotatable Bonds	4

Synonyms

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537-42-8

trans-pterostilbene

4-(3,5-Dimethoxystyryl)phenol

(E)-4-(3,5-dimethoxystyryl)phenol

4-[(E)-2-(3,5-dimethoxyphenyl)ethenyl]phenol

3',5'-Dimethoxy-4-stilbenol

18259-15-9

pterostilbene, (E)-

4-[(E)-2-(3,5-dimethoxyphenyl)vinyl]phenol

3,5-Dimethoxy-4'-hydroxy-trans-stilbene

There are more than 10 synonyms. If you wish to see them all click here.

2D Structure

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3D Structure

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ADMET Properties (via admetSAR 2)

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Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9965	99.65%
Caco-2	+	0.7473	74.73%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.6571	65.71%
Subcellular localzation	Mitochondria	0.8298	82.98%
OATP2B1 inhibitior	-	0.8570	85.70%
OATP1B1 inhibitior	+	0.9056	90.56%
OATP1B3 inhibitior	+	0.9791	97.91%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	-	0.5715	57.15%
P-glycoprotein inhibitior	-	0.7975	79.75%
P-glycoprotein substrate	-	0.9728	97.28%
CYP3A4 substrate	-	0.6573	65.73%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.6581	65.81%
CYP3A4 inhibition	-	0.5979	59.79%
CYP2C9 inhibition	-	0.9304	93.04%
CYP2C19 inhibition	+	0.7583	75.83%
CYP2D6 inhibition	-	0.9249	92.49%
CYP1A2 inhibition	+	0.8736	87.36%
CYP2C8 inhibition	+	0.4775	47.75%
CYP inhibitory promiscuity	+	0.6700	67.00%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.5979	59.79%
Carcinogenicity (trinary)	Non-required	0.5992	59.92%
Eye corrosion	-	0.9657	96.57%
Eye irritation	+	0.9623	96.23%
Skin irritation	-	0.6780	67.80%
Skin corrosion	-	0.9724	97.24%
Ames mutagenesis	-	0.7400	74.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6932	69.32%
Micronuclear	-	0.5500	55.00%
Hepatotoxicity	-	0.6343	63.43%
skin sensitisation	-	0.6031	60.31%
Respiratory toxicity	-	0.9000	90.00%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	-	0.8125	81.25%
Nephrotoxicity	+	0.4634	46.34%
Acute Oral Toxicity (c)	III	0.6558	65.58%
Estrogen receptor binding	+	0.8745	87.45%
Androgen receptor binding	+	0.8175	81.75%
Thyroid receptor binding	+	0.7715	77.15%
Glucocorticoid receptor binding	+	0.7489	74.89%
Aromatase binding	+	0.9173	91.73%
PPAR gamma	+	0.8325	83.25%
Honey bee toxicity	-	0.9277	92.77%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9483	94.83%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	530 nM	IC50	via Super-PRED
CHEMBL2096618	P11274	Bcr/Abl fusion protein	10000 nM	IC50	PMID: 16686543
CHEMBL221	P23219	Cyclooxygenase-1	700 nM	IC50	PMID: 18487053
CHEMBL230	P35354	Cyclooxygenase-2	820 nM	IC50	PMID: 18487053
CHEMBL2231	P04798	Cytochrome P450 1A1	570 nM	Ki	DOI: 10.1039/C0MD00242A
CHEMBL4878	Q16678	Cytochrome P450 1B1	900 nM 1400 nM	Ki IC50	via Super-PRED DOI: 10.1039/C3MD00317E
CHEMBL1741189	P55789	FAD-linked sulfhydryl oxidase ALR	778 nM	AC50	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM	Potency	via CMAUP
CHEMBL2608	P10253	Lysosomal alpha-glucosidase	11220.2 nM	Potency	via CMAUP
CHEMBL4040	P28482	MAP kinase ERK2	39810.7 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	11220.2 nM 15848.9 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293277	O15118	Niemann-Pick C1 protein	2511.9 nM	Potency	via CMAUP
CHEMBL4302	P08183	P-glycoprotein 1	42000 nM	IC50	PMID: 16686543
CHEMBL3959	P16083	Quinone reductase 2	5100 nM	IC50	PMID: 23953689
CHEMBL1293294	P51151	Ras-related protein Rab-9A	3162.3 nM	Potency	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	95.53%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.87%	95.56%
CHEMBL242	Q92731	Estrogen receptor beta	92.73%	98.35%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	91.94%	96.00%
CHEMBL3194	P02766	Transthyretin	88.63%	90.71%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.41%	86.33%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	85.86%	96.09%
CHEMBL4208	P20618	Proteasome component C5	85.56%	90.00%
CHEMBL2487	P05067	Beta amyloid A4 protein	85.17%	96.74%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.00%	93.99%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.89%	91.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.51%	99.15%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.49%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	81.28%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.03%	99.17%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.

Artemisia pedemontana subsp. assoana

Astragalus sempervirens

Calamus draco

Calostephane divaricata