5-(1-Benzofuran-2-yl)-2-methylbenzene-1,3-diol

Details

• Internal ID: b1f895e3-e970-4466-8803-b67366a362b3
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-(1-benzofuran-2-yl)-2-methylbenzene-1,3-diol
• SMILES (Canonical): CC1=C(C=C(C=C1O)C2=CC3=CC=CC=C3O2)O
• SMILES (Isomeric): CC1=C(C=C(C=C1O)C2=CC3=CC=CC=C3O2)O
• InChI: InChI=1S/C15H12O3/c1-9-12(16)6-11(7-13(9)17)15-8-10-4-2-3-5-14(10)18-15/h2-8,16-17H,1H3
• InChI Key: UJNBNDIUQWFUNM-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₁₂O₃
• Molecular Weight: 240.25 g/mol
• Exact Mass: 240.078644241 g/mol
• Topological Polar Surface Area (TPSA): 53.60 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.82
• H-Bond Acceptor: 3
• H-Bond Donor: 2
• Rotatable Bonds: 1

Synonyms

• 1,3-benzenediol, 5-(2-benzofuranyl)-2-methyl-
• 5-(1-benzofuran-2-yl)-2-methylbenzene-1,3-diol
• CHEMBL462853
• InChI=1/C15H12O3/c1-9-12(16)6-11(7-13(9)17)15-8-10-4-2-3-5-14(10)18-15/h2-8,16-17H,1H

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9943	99.43%
Caco-2	+	0.5948	59.48%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	+	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6968	69.68%
OATP2B1 inhibitior	-	0.5812	58.12%
OATP1B1 inhibitior	+	0.9445	94.45%
OATP1B3 inhibitior	+	0.8689	86.89%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.5576	55.76%
P-glycoprotein inhibitior	-	0.6525	65.25%
P-glycoprotein substrate	-	0.9595	95.95%
CYP3A4 substrate	-	0.5939	59.39%
CYP2C9 substrate	-	0.5929	59.29%
CYP2D6 substrate	-	0.6770	67.70%
CYP3A4 inhibition	-	0.6883	68.83%
CYP2C9 inhibition	+	0.9182	91.82%
CYP2C19 inhibition	+	0.8917	89.17%
CYP2D6 inhibition	-	0.8592	85.92%
CYP1A2 inhibition	+	0.9562	95.62%
CYP2C8 inhibition	+	0.5837	58.37%
CYP inhibitory promiscuity	+	0.9545	95.45%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.8600	86.00%
Carcinogenicity (trinary)	Non-required	0.3736	37.36%
Eye corrosion	-	0.9868	98.68%
Eye irritation	+	0.8834	88.34%
Skin irritation	+	0.4912	49.12%
Skin corrosion	-	0.8036	80.36%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5388	53.88%
Micronuclear	+	0.7300	73.00%
Hepatotoxicity	+	0.7160	71.60%
skin sensitisation	-	0.7530	75.30%
Respiratory toxicity	-	0.8667	86.67%
Reproductive toxicity	+	0.5556	55.56%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.6072	60.72%
Acute Oral Toxicity (c)	III	0.5681	56.81%
Estrogen receptor binding	+	0.9387	93.87%
Androgen receptor binding	+	0.7948	79.48%
Thyroid receptor binding	+	0.8124	81.24%
Glucocorticoid receptor binding	+	0.8964	89.64%
Aromatase binding	+	0.8551	85.51%
PPAR gamma	+	0.9304	93.04%
Honey bee toxicity	-	0.9650	96.50%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6200	62.00%
Fish aquatic toxicity	+	0.9513	95.13%

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	96.91%	91.11%
CHEMBL5409	Q8TDU6	G-protein coupled bile acid receptor 1	91.46%	93.65%
CHEMBL3401	O75469	Pregnane X receptor	89.52%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.30%	94.00%
CHEMBL2581	P07339	Cathepsin D	89.28%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.51%	99.15%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.08%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.55%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	83.79%	86.33%
CHEMBL3959	P16083	Quinone reductase 2	82.94%	89.49%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.04%	99.23%

Plants that contains it

• Ardisia sieboldii
• Stemona collinsae

Cross-Links

• PubChem: 641365
• LOTUS: LTS0188917
• wikiData: Q105365781