(E)-3,4,5-Trihydroxystilbene

Details

• Internal ID: c3ba8d22-46f2-4d4c-a3d2-6e5b66c4e105
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 5-[(E)-2-phenylethenyl]benzene-1,2,3-triol
• SMILES (Canonical): C1=CC=C(C=C1)C=CC2=CC(=C(C(=C2)O)O)O
• SMILES (Isomeric): C1=CC=C(C=C1)/C=C/C2=CC(=C(C(=C2)O)O)O
• InChI: InChI=1S/C14H12O3/c15-12-8-11(9-13(16)14(12)17)7-6-10-4-2-1-3-5-10/h1-9,15-17H/b7-6+
• InChI Key: IYWFOPPYQUEKHN-VOTSOKGWSA-N
• Popularity: 93 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₃
• Molecular Weight: 228.24 g/mol
• Exact Mass: 228.078644241 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 3.10
• Atomic LogP (AlogP): 2.97
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 2

Synonyms

• SCHEMBL41159
• (E)-Stilbene-3,4,5-triol
• CHEMBL455488
• (E)-3,4,5-Trihydroxystilbene
• 3,4,5-trihydroxy-transstilbene
• IYWFOPPYQUEKHN-VOTSOKGWSA-N

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9759	97.59%
Caco-2	-	0.5621	56.21%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5549	55.49%
OATP2B1 inhibitior	-	0.5809	58.09%
OATP1B1 inhibitior	+	0.9189	91.89%
OATP1B3 inhibitior	+	0.9770	97.70%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8838	88.38%
BSEP inhibitior	-	0.7154	71.54%
P-glycoprotein inhibitior	-	0.9406	94.06%
P-glycoprotein substrate	-	0.9917	99.17%
CYP3A4 substrate	-	0.7909	79.09%
CYP2C9 substrate	-	0.5963	59.63%
CYP2D6 substrate	-	0.7204	72.04%
CYP3A4 inhibition	-	0.6237	62.37%
CYP2C9 inhibition	+	0.6250	62.50%
CYP2C19 inhibition	-	0.7996	79.96%
CYP2D6 inhibition	-	0.9121	91.21%
CYP1A2 inhibition	+	0.8523	85.23%
CYP2C8 inhibition	-	0.5792	57.92%
CYP inhibitory promiscuity	+	0.8104	81.04%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7723	77.23%
Carcinogenicity (trinary)	Non-required	0.5207	52.07%
Eye corrosion	-	0.9394	93.94%
Eye irritation	+	0.9946	99.46%
Skin irritation	+	0.7183	71.83%
Skin corrosion	+	0.5771	57.71%
Ames mutagenesis	-	0.8000	80.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7610	76.10%
Micronuclear	+	0.6700	67.00%
Hepatotoxicity	+	0.6620	66.20%
skin sensitisation	+	0.9619	96.19%
Respiratory toxicity	-	0.6556	65.56%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.7875	78.75%
Nephrotoxicity	-	0.8245	82.45%
Acute Oral Toxicity (c)	III	0.7288	72.88%
Estrogen receptor binding	+	0.9380	93.80%
Androgen receptor binding	+	0.9295	92.95%
Thyroid receptor binding	+	0.8226	82.26%
Glucocorticoid receptor binding	+	0.8484	84.84%
Aromatase binding	+	0.8813	88.13%
PPAR gamma	+	0.9519	95.19%
Honey bee toxicity	-	0.9649	96.49%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	+	0.6100	61.00%
Fish aquatic toxicity	+	0.9808	98.08%

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	98.97%	91.11%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.75%	95.56%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	93.06%	94.62%
CHEMBL3194	P02766	Transthyretin	91.56%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	90.39%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.05%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	88.16%	91.49%
CHEMBL3192	Q9BY41	Histone deacetylase 8	85.80%	93.99%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.05%	94.08%
CHEMBL3401	O75469	Pregnane X receptor	83.77%	94.73%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	82.94%	91.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	81.00%	99.15%

Plants that contains it

• Reynoutria japonica

Cross-Links

• PubChem: 9964599
• NPASS: NPC176527