4-[2-(3,5-Dihydroxyphenyl)ethenyl]benzene-1,2-diol

Details

• Internal ID: ed523cce-1847-46f6-ba47-980154b268ac
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 4-[2-(3,5-dihydroxyphenyl)ethenyl]benzene-1,2-diol
• SMILES (Canonical): C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1C=CC2=CC(=CC(=C2)O)O)O)O
• InChI: InChI=1S/C14H12O4/c15-11-5-10(6-12(16)8-11)2-1-9-3-4-13(17)14(18)7-9/h1-8,15-18H
• InChI Key: CDRPUGZCRXZLFL-UHFFFAOYSA-N
• Popularity: 716 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₄
• Molecular Weight: 244.24 g/mol
• Exact Mass: 244.07355886 g/mol
• Topological Polar Surface Area (TPSA): 80.90 Ų
• XlogP: 2.90
• Atomic LogP (AlogP): 2.68
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

• Astringenin;trans-Piceatannol
• MLS003171221
• 3,3',4',5-tetrahydroxystilbene
• PICESTANNOL
• Kinome_2842
• KBioGR_000460
• KBioSS_000460
• CHEMBL1972346
• KBio2_000460
• KBio2_003028
• KBio2_005596
• KBio3_000859
• KBio3_000860
• DTXSID20860062
• CDRPUGZCRXZLFL-UHFFFAOYSA-N
• Bio2_000400
• Bio2_000880
• HMS3268E09
• HMS3372C20
• HMS3656L16
• AKOS030228081
• NCGC00094226-11
• NCI60_003368
• SMR001875127
• FT-0654837
• FT-0673895
• Q27164196

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9403	94.03%
Caco-2	+	0.7659	76.59%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.5195	51.95%
OATP2B1 inhibitior	-	0.6931	69.31%
OATP1B1 inhibitior	+	0.9789	97.89%
OATP1B3 inhibitior	+	0.9799	97.99%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9088	90.88%
BSEP inhibitior	-	0.6653	66.53%
P-glycoprotein inhibitior	-	0.9568	95.68%
P-glycoprotein substrate	-	0.9936	99.36%
CYP3A4 substrate	-	0.7238	72.38%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.7204	72.04%
CYP3A4 inhibition	+	0.5427	54.27%
CYP2C9 inhibition	+	0.6182	61.82%
CYP2C19 inhibition	-	0.9026	90.26%
CYP2D6 inhibition	-	0.9231	92.31%
CYP1A2 inhibition	+	0.9107	91.07%
CYP2C8 inhibition	-	0.6100	61.00%
CYP inhibitory promiscuity	+	0.7651	76.51%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.7723	77.23%
Carcinogenicity (trinary)	Non-required	0.5596	55.96%
Eye corrosion	-	0.9698	96.98%
Eye irritation	+	0.9970	99.70%
Skin irritation	+	0.6089	60.89%
Skin corrosion	-	0.5875	58.75%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7864	78.64%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	-	0.5964	59.64%
skin sensitisation	+	0.9376	93.76%
Respiratory toxicity	-	0.6667	66.67%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.5896	58.96%
Acute Oral Toxicity (c)	III	0.7909	79.09%
Estrogen receptor binding	+	0.9138	91.38%
Androgen receptor binding	+	0.8411	84.11%
Thyroid receptor binding	+	0.7823	78.23%
Glucocorticoid receptor binding	+	0.8424	84.24%
Aromatase binding	+	0.9377	93.77%
PPAR gamma	+	0.9167	91.67%
Honey bee toxicity	-	0.8277	82.77%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9851	98.51%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL5903	Q04771	Activin receptor type-1	501.19 nM	Ki	via CMAUP
CHEMBL4247	Q9UM73	ALK tyrosine kinase receptor	251.19 nM	Ki	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	794.3 nM	Potency	via Super-PRED
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	240 nM	IC50	via Super-PRED
CHEMBL2637	P53779	c-Jun N-terminal kinase 3	50.12 nM	Ki	via CMAUP
CHEMBL5073	Q8IU85	CaM kinase I delta	501.19 nM	Ki	via CMAUP
CHEMBL4147	Q9UQM7	CaM kinase II alpha	794.33 nM	Ki	via CMAUP
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	63.1 nM	Ki	via CMAUP
CHEMBL4101	P17612	cAMP-dependent protein kinase alpha-catalytic subunit	1584.89 nM	Ki	via CMAUP
CHEMBL2793	P48729	Casein kinase I alpha	316.23 nM	Ki	via CMAUP
CHEMBL5719	P49336	Cell division protein kinase 8	251.19 nM	Ki	via CMAUP
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	501.19 nM	Ki	via CMAUP
CHEMBL5543	Q9Y463	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	100 nM	Ki	via CMAUP
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	31.62 nM	Ki	via CMAUP
CHEMBL3650	P11362	Fibroblast growth factor receptor 1	630.96 nM	Ki	via CMAUP
CHEMBL2695	Q05397	Focal adhesion kinase 1	794.33 nM	Ki	via CMAUP
CHEMBL5678	P34947	G protein-coupled receptor kinase 5	501.19 nM	Ki	via CMAUP
CHEMBL2850	P49840	Glycogen synthase kinase-3 alpha	3162.28 nM	Ki	via CMAUP
CHEMBL262	P49841	Glycogen synthase kinase-3 beta	1000 nM	Ki	via CMAUP
CHEMBL2424	Q04760	Glyoxalase I	760 nM	IC50	via Super-PRED
CHEMBL3529	Q14164	Inhibitor of nuclear factor kappa B kinase epsilon subunit	398.11 nM	Ki	via CMAUP
CHEMBL1075104	Q5S007	Leucine-rich repeat serine/threonine-protein kinase 2	501.19 nM	Ki	via CMAUP
CHEMBL5627	P29376	Leukocyte tyrosine kinase receptor	316.23 nM	Ki	via CMAUP
CHEMBL5754	Q96L34	MAP/microtubule affinity-regulating kinase 4	50.12 nM	Ki	via CMAUP
CHEMBL4578	Q14680	Maternal embryonic leucine zipper kinase	79.43 nM	Ki	via CMAUP
CHEMBL2873	Q02779	Mitogen-activated protein kinase kinase kinase 10	100 nM	Ki	via CMAUP
CHEMBL6166	O95819	Mitogen-activated protein kinase kinase kinase kinase 4	501.19 nM	Ki	via CMAUP
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	1000 nM	Ki	via CMAUP
CHEMBL1293235	P02545	Prelamin-A/C	56.2 nM	Potency	via Super-PRED
CHEMBL3920	Q04759	Protein kinase C theta	794.33 nM	Ki	via CMAUP
CHEMBL5568	P08922	Proto-oncogene tyrosine-protein kinase ROS	794.33 nM	Ki	via CMAUP
CHEMBL3231	Q13464	Rho-associated protein kinase 1	2511.89 nM	Ki	via CMAUP
CHEMBL2973	O75116	Rho-associated protein kinase 2	125.89 nM	Ki	via CMAUP
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	1584.89 nM	Ki	via CMAUP
CHEMBL5600	P27448	Serine/threonine-protein kinase c-TAK1	251.19 nM	Ki	via CMAUP
CHEMBL4708	Q13188	Serine/threonine-protein kinase MST2	630.96 nM	Ki	via CMAUP
CHEMBL2147	P11309	Serine/threonine-protein kinase PIM1	2511.89 nM	Ki	via CMAUP
CHEMBL5818	P51817	Serine/threonine-protein kinase PRKX	630.96 nM	Ki	via CMAUP
CHEMBL5794	Q9HBY8	Serine/threonine-protein kinase Sgk2	316.23 nM	Ki	via CMAUP
CHEMBL5699	Q9H0K1	Serine/threonine-protein kinase SIK2	100 nM	Ki	via CMAUP
CHEMBL5261	Q7L7X3	Serine/threonine-protein kinase TAO1	1000 nM	Ki	via CMAUP
CHEMBL5408	Q9UHD2	Serine/threonine-protein kinase TBK1	630.96 nM	Ki	via CMAUP
CHEMBL4599	Q07912	Tyrosine kinase non-receptor protein 2	630.96 nM	Ki	via CMAUP
CHEMBL5251	Q06187	Tyrosine-protein kinase BTK	630.96 nM	Ki	via CMAUP
CHEMBL3234	P08631	Tyrosine-protein kinase HCK	398.11 nM	Ki	via CMAUP
CHEMBL2971	O60674	Tyrosine-protein kinase JAK2	794.33 nM	Ki	via CMAUP
CHEMBL2148	P52333	Tyrosine-protein kinase JAK3	1000 nM	Ki	via CMAUP
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	398.11 nM	Ki	via CMAUP
CHEMBL5314	Q06418	Tyrosine-protein kinase receptor TYRO3	79.43 nM	Ki	via CMAUP
CHEMBL1868	P17948	Vascular endothelial growth factor receptor 1	501.19 nM	Ki	via CMAUP

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	98.80%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.61%	91.11%
CHEMBL3194	P02766	Transthyretin	96.88%	90.71%
CHEMBL1929	P47989	Xanthine dehydrogenase	93.27%	96.12%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.51%	95.56%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.81%	96.00%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.53%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.72%	86.33%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	83.75%	80.78%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.78%	89.00%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.33%	91.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.93%	94.45%
CHEMBL3401	O75469	Pregnane X receptor	80.66%	94.73%
CHEMBL4208	P20618	Proteasome component C5	80.40%	90.00%

Plants that contains it

• Abies alba
• Abies spectabilis
• Aiphanes horrida
• Bombax ceiba
• Caragana tibetica
• Centrolobium robustum
• Centrolobium tomentosum
• Chamaecrista greggii
• Cyperus longus
• Dioscorea antaly
• Endiandra xanthocarpa
• Eucalyptus sideroxylon
• Fagopyrum megacarpum
• Helichrysum harveyanum
• Hemsleya graciliflora
• Maackia amurensis
• Melaleuca leucadendra
• Parthenocissus quinquefolia
• Parthenocissus tricuspidata
• Picea abies
• Picea engelmannii
• Picea glauca
• Picea jezoensis
• Picea mariana
• Picea rubens
• Picea sitchensis
• Reynoutria japonica
• Rheum rhabarbarum
• Schotia brachypetala
• Senna garrettiana
• Senna lindheimeriana
• Smilax bracteata
• Smilax corbularia
• Sophora yunnanensis
• Spirotropis longifolia
• Syagrus romanzoffiana
• Vitis amurensis
• Vitis vinifera

Cross-Links

• PubChem: 4813
• NPASS: NPC105727
• ChEMBL: CHEMBL1972346
• LOTUS: LTS0094372
• wikiData: Q27164196