5-[(1E)-2-(3,4-dihydroxyphenyl)vinyl]-benzene1,2,3-triol

Details

• Internal ID: 61666545-0f0e-4fc1-8b74-ddaba65a4584
• Taxonomy: Phenylpropanoids and polyketides > Stilbenes
• IUPAC Name: 5-[(E)-2-(3,4-dihydroxyphenyl)ethenyl]benzene-1,2,3-triol
• SMILES (Canonical): C1=CC(=C(C=C1C=CC2=CC(=C(C(=C2)O)O)O)O)O
• SMILES (Isomeric): C1=CC(=C(C=C1/C=C/C2=CC(=C(C(=C2)O)O)O)O)O
• InChI: InChI=1S/C14H12O5/c15-10-4-3-8(5-11(10)16)1-2-9-6-12(17)14(19)13(18)7-9/h1-7,15-19H/b2-1+
• InChI Key: NHDCJIRSEKZXEL-OWOJBTEDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₂O₅
• Molecular Weight: 260.24 g/mol
• Exact Mass: 260.06847348 g/mol
• Topological Polar Surface Area (TPSA): 101.00 Ų
• XlogP: 2.40
• Atomic LogP (AlogP): 2.39
• H-Bond Acceptor: 5
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• CHEMBL2260732
• NHDCJIRSEKZXEL-OWOJBTEDSA-N
• 5-[(1E)-2-(3,4-dihydroxyphenyl)vinyl]-benzene1,2,3-triol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9403	94.03%
Caco-2	+	0.6750	67.50%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	+	0.6000	60.00%
Subcellular localzation	Mitochondria	0.5195	51.95%
OATP2B1 inhibitior	-	0.5589	55.89%
OATP1B1 inhibitior	+	0.9603	96.03%
OATP1B3 inhibitior	+	0.9799	97.99%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9088	90.88%
BSEP inhibitior	-	0.5701	57.01%
P-glycoprotein inhibitior	-	0.9660	96.60%
P-glycoprotein substrate	-	0.9920	99.20%
CYP3A4 substrate	-	0.7659	76.59%
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	-	0.7735	77.35%
CYP inhibitory promiscuity	+	0.7651	76.51%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.7723	77.23%
Carcinogenicity (trinary)	Non-required	0.5596	55.96%
Eye corrosion	-	0.9698	96.98%
Eye irritation	+	0.9837	98.37%
Skin irritation	+	0.6089	60.89%
Skin corrosion	-	0.5875	58.75%
Ames mutagenesis	-	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7566	75.66%
Micronuclear	+	0.7400	74.00%
Hepatotoxicity	+	0.5024	50.24%
skin sensitisation	+	0.9376	93.76%
Respiratory toxicity	-	0.5667	56.67%
Reproductive toxicity	+	0.5222	52.22%
Mitochondrial toxicity	-	0.7250	72.50%
Nephrotoxicity	-	0.8491	84.91%
Acute Oral Toxicity (c)	III	0.7909	79.09%
Estrogen receptor binding	+	0.8771	87.71%
Androgen receptor binding	+	0.9453	94.53%
Thyroid receptor binding	+	0.8337	83.37%
Glucocorticoid receptor binding	+	0.8842	88.42%
Aromatase binding	+	0.8683	86.83%
PPAR gamma	+	0.9092	90.92%
Honey bee toxicity	-	0.9241	92.41%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9851	98.51%

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	99.37%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	98.57%	91.49%
CHEMBL3194	P02766	Transthyretin	95.95%	90.71%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.30%	96.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.13%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.16%	99.15%
CHEMBL3788	O00444	Serine/threonine-protein kinase PLK4	87.08%	83.65%
CHEMBL1929	P47989	Xanthine dehydrogenase	85.48%	96.12%
CHEMBL1293249	Q13887	Kruppel-like factor 5	84.47%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.63%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	82.58%	94.73%

Plants that contains it

• Vouacapoua americana

Cross-Links

• PubChem: 11777365
• LOTUS: LTS0051600
• wikiData: Q76422033