Pinosylvin methyl ether

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	efaf16e7-1f79-4e8a-97e2-70a65a3020af
Taxonomy	Phenylpropanoids and polyketides > Stilbenes
IUPAC Name	3-methoxy-5-[(E)-2-phenylethenyl]phenol
SMILES (Canonical)	COC1=CC(=CC(=C1)O)C=CC2=CC=CC=C2
SMILES (Isomeric)	COC1=CC(=CC(=C1)O)/C=C/C2=CC=CC=C2
InChI	InChI=1S/C15H14O2/c1-17-15-10-13(9-14(16)11-15)8-7-12-5-3-2-4-6-12/h2-11,16H,1H3/b8-7+
InChI Key	JVIXPWIEOVZVJC-BQYQJAHWSA-N
Popularity	24 references in papers

Physical and Chemical Properties

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Molecular Formula	C₁₅H₁₄O₂
Molecular Weight	226.27 g/mol
Exact Mass	226.099379685 g/mol
Topological Polar Surface Area (TPSA)	29.50 Å²
XlogP	3.80
Atomic LogP (AlogP)	3.57
H-Bond Acceptor	2
H-Bond Donor	1
Rotatable Bonds	3

Synonyms

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PINOSYLVIN METHYL ETHER

Pinosylvin monomethyl ether

(E)-3-Methoxy-5-styrylphenol

(E)-3-Hydroxy-5-methoxystilbene

5-Methoxy-3-stilbenol

3-methoxy-5-[(E)-2-phenylethenyl]phenol

CHEBI:8227

PINOSYLVIN MONO METHYL ETHER

3-Stilbenol, 5-methoxy-

MLS002608527

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	+	1.0000	100.00%
Caco-2	+	0.8030	80.30%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7398	73.98%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9165	91.65%
OATP1B3 inhibitior	+	0.9840	98.40%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	-	0.5092	50.92%
P-glycoprotein inhibitior	-	0.8083	80.83%
P-glycoprotein substrate	-	0.9831	98.31%
CYP3A4 substrate	-	0.6689	66.89%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.6581	65.81%
CYP3A4 inhibition	-	0.8155	81.55%
CYP2C9 inhibition	-	0.8734	87.34%
CYP2C19 inhibition	+	0.8314	83.14%
CYP2D6 inhibition	-	0.9319	93.19%
CYP1A2 inhibition	+	0.9121	91.21%
CYP2C8 inhibition	+	0.5983	59.83%
CYP inhibitory promiscuity	+	0.6662	66.62%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.5757	57.57%
Carcinogenicity (trinary)	Non-required	0.4701	47.01%
Eye corrosion	-	0.9639	96.39%
Eye irritation	+	0.9701	97.01%
Skin irritation	-	0.6394	63.94%
Skin corrosion	-	0.9374	93.74%
Ames mutagenesis	-	0.7300	73.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4796	47.96%
Micronuclear	-	0.6000	60.00%
Hepatotoxicity	-	0.5425	54.25%
skin sensitisation	+	0.6904	69.04%
Respiratory toxicity	-	0.8000	80.00%
Reproductive toxicity	-	0.6111	61.11%
Mitochondrial toxicity	-	0.8625	86.25%
Nephrotoxicity	-	0.5722	57.22%
Acute Oral Toxicity (c)	III	0.5629	56.29%
Estrogen receptor binding	+	0.9087	90.87%
Androgen receptor binding	+	0.7892	78.92%
Thyroid receptor binding	+	0.6470	64.70%
Glucocorticoid receptor binding	-	0.5658	56.58%
Aromatase binding	+	0.8460	84.60%
PPAR gamma	+	0.8274	82.74%
Honey bee toxicity	-	0.9180	91.80%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.6700	67.00%
Fish aquatic toxicity	+	0.9012	90.12%

Targets

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Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL1293255	P15428	15-hydroxyprostaglandin dehydrogenase [NAD+]	28183.8 nM	Potency	via CMAUP
CHEMBL3577	P00352	Aldehyde dehydrogenase 1A1	39810.7 nM	Potency	via CMAUP
CHEMBL4096	P04637	Cellular tumor antigen p53	10000 nM 7943.3 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	31622.8 nM 31622.8 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	19952.6 nM	Potency	via CMAUP
CHEMBL1293226	B2RXH2	Lysine-specific demethylase 4D-like	25118.9 nM	Potency	via CMAUP
CHEMBL1293224	P10636	Microtubule-associated protein tau	28183.8 nM 19952.6 nM	Potency Potency	via CMAUP via CMAUP
CHEMBL1293232	Q16637	Survival motor neuron protein	25118.9 nM	Potency	via CMAUP
CHEMBL1293227	O75604	Ubiquitin carboxyl-terminal hydrolase 2	25118.9 nM	Potency	via CMAUP
CHEMBL4794	Q8NER1	Vanilloid receptor	23700 nM 30000 nM 15000 nM	IC50 IC50 IC50	PMID: 26750258 PMID: 26750258 PMID: 26750258

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	97.28%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	96.36%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.66%	86.33%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	92.90%	96.00%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	89.32%	94.08%
CHEMBL3192	Q9BY41	Histone deacetylase 8	88.37%	93.99%
CHEMBL2581	P07339	Cathepsin D	88.31%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	86.12%	94.73%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	85.80%	94.62%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	85.80%	91.71%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	83.43%	92.68%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.66%	96.09%
CHEMBL4208	P20618	Proteasome component C5	81.17%	90.00%
CHEMBL3194	P02766	Transthyretin	80.92%	90.71%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.87%	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.

Acacia simplicifolia

Alnus maximowiczii

Alnus sieboldiana

Amentotaxus argotaenia

Ammodendron karelinii

Anacyclus pyrethrum

Arachniodes carvifolia

Aristolochia triangularis

Aster tataricus

Bowdichia virgilioides

Brachylaena perrieri

Buglossoides arvensis