1,3-Benzenediol, 5-(2-benzofuranyl)-

Details

• Internal ID: 889ff64a-b6fe-4912-a4f9-027f3d7f0a52
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-(1-benzofuran-2-yl)benzene-1,3-diol
• SMILES (Canonical): C1=CC=C2C(=C1)C=C(O2)C3=CC(=CC(=C3)O)O
• SMILES (Isomeric): C1=CC=C2C(=C1)C=C(O2)C3=CC(=CC(=C3)O)O
• InChI: InChI=1S/C14H10O3/c15-11-5-10(6-12(16)8-11)14-7-9-3-1-2-4-13(9)17-14/h1-8,15-16H
• InChI Key: ZZTDCNYCFAJAMX-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₄H₁₀O₃
• Molecular Weight: 226.23 g/mol
• Exact Mass: 226.062994177 g/mol
• Topological Polar Surface Area (TPSA): 53.60 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.51
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 439900-83-1
• 5-(Benzofuran-2-yl)benzene-1,3-diol
• STEMOFURAN A
• 5-(1-benzofuran-2-yl)benzene-1,3-diol
• CHEMBL464900
• DTXSID00348893
• InChI=1/C14H10O3/c15-11-5-10(6-12(16)8-11)14-7-9-3-1-2-4-13(9)17-14/h1-8,15-16

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9923	99.23%
Caco-2	+	0.5000	50.00%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.6429	64.29%
Subcellular localzation	Mitochondria	0.4914	49.14%
OATP2B1 inhibitior	-	0.7166	71.66%
OATP1B1 inhibitior	+	0.9431	94.31%
OATP1B3 inhibitior	+	0.9070	90.70%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.5363	53.63%
P-glycoprotein inhibitior	-	0.7893	78.93%
P-glycoprotein substrate	-	0.9676	96.76%
CYP3A4 substrate	-	0.6401	64.01%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.3539	35.39%
CYP3A4 inhibition	+	0.5879	58.79%
CYP2C9 inhibition	+	0.7406	74.06%
CYP2C19 inhibition	+	0.7806	78.06%
CYP2D6 inhibition	-	0.8169	81.69%
CYP1A2 inhibition	+	0.8977	89.77%
CYP2C8 inhibition	+	0.7106	71.06%
CYP inhibitory promiscuity	+	0.9068	90.68%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Warning	0.4178	41.78%
Eye corrosion	-	0.9794	97.94%
Eye irritation	+	0.9625	96.25%
Skin irritation	+	0.5504	55.04%
Skin corrosion	-	0.9501	95.01%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6955	69.55%
Micronuclear	+	0.6259	62.59%
Hepatotoxicity	+	0.7095	70.95%
skin sensitisation	-	0.7961	79.61%
Respiratory toxicity	-	0.7556	75.56%
Reproductive toxicity	-	0.5444	54.44%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.5703	57.03%
Acute Oral Toxicity (c)	III	0.7471	74.71%
Estrogen receptor binding	+	0.9473	94.73%
Androgen receptor binding	+	0.6981	69.81%
Thyroid receptor binding	+	0.7791	77.91%
Glucocorticoid receptor binding	+	0.8461	84.61%
Aromatase binding	+	0.9126	91.26%
PPAR gamma	+	0.9241	92.41%
Honey bee toxicity	-	0.9276	92.76%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.8817	88.17%

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	97.95%	91.11%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	83.55%	94.00%
CHEMBL2581	P07339	Cathepsin D	83.33%	98.95%
CHEMBL3401	O75469	Pregnane X receptor	83.31%	94.73%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	83.25%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.74%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	81.64%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	81.60%	95.56%

Plants that contains it

• Stemona collinsae

Cross-Links

• PubChem: 641363
• LOTUS: LTS0044403
• wikiData: Q82123871