2-(4-Hydroxy-2-methoxyphenyl)-5-methoxy-1-benzofuran-6-ol

Details

• Internal ID: b0e561d0-dcda-4b11-8a3b-48fd6d7a821a
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 2-(4-hydroxy-2-methoxyphenyl)-5-methoxy-1-benzofuran-6-ol
• SMILES (Canonical): COC1=C(C=CC(=C1)O)C2=CC3=CC(=C(C=C3O2)O)OC
• SMILES (Isomeric): COC1=C(C=CC(=C1)O)C2=CC3=CC(=C(C=C3O2)O)OC
• InChI: InChI=1S/C16H14O5/c1-19-14-7-10(17)3-4-11(14)15-5-9-6-16(20-2)12(18)8-13(9)21-15/h3-8,17-18H,1-2H3
• InChI Key: DZCYWLFZZXXDTO-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₆H₁₄O₅
• Molecular Weight: 286.28 g/mol
• Exact Mass: 286.08412354 g/mol
• Topological Polar Surface Area (TPSA): 72.10 Ų
• XlogP: 3.20
• Atomic LogP (AlogP): 3.53
• H-Bond Acceptor: 5
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	+	0.7559	75.59%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7499	74.99%
OATP2B1 inhibitior	-	0.5810	58.10%
OATP1B1 inhibitior	+	0.8809	88.09%
OATP1B3 inhibitior	+	0.9378	93.78%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	-	0.6641	66.41%
P-glycoprotein inhibitior	-	0.5385	53.85%
P-glycoprotein substrate	-	0.5242	52.42%
CYP3A4 substrate	+	0.5083	50.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4038	40.38%
CYP3A4 inhibition	-	0.5808	58.08%
CYP2C9 inhibition	+	0.8944	89.44%
CYP2C19 inhibition	+	0.9181	91.81%
CYP2D6 inhibition	-	0.5954	59.54%
CYP1A2 inhibition	+	0.8881	88.81%
CYP2C8 inhibition	+	0.7796	77.96%
CYP inhibitory promiscuity	+	0.9368	93.68%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8708	87.08%
Carcinogenicity (trinary)	Warning	0.3621	36.21%
Eye corrosion	-	0.9874	98.74%
Eye irritation	+	0.6191	61.91%
Skin irritation	-	0.7313	73.13%
Skin corrosion	-	0.9530	95.30%
Ames mutagenesis	-	0.5300	53.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5895	58.95%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	-	0.6966	69.66%
skin sensitisation	-	0.8658	86.58%
Respiratory toxicity	-	0.6778	67.78%
Reproductive toxicity	+	0.7333	73.33%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6193	61.93%
Acute Oral Toxicity (c)	III	0.5903	59.03%
Estrogen receptor binding	+	0.9257	92.57%
Androgen receptor binding	+	0.8552	85.52%
Thyroid receptor binding	+	0.7935	79.35%
Glucocorticoid receptor binding	+	0.9275	92.75%
Aromatase binding	+	0.9125	91.25%
PPAR gamma	+	0.8020	80.20%
Honey bee toxicity	-	0.9189	91.89%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5551	55.51%
Fish aquatic toxicity	+	0.9408	94.08%

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	96.64%	91.11%
CHEMBL242	Q92731	Estrogen receptor beta	95.49%	98.35%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.00%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.52%	85.14%
CHEMBL2581	P07339	Cathepsin D	91.05%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.75%	86.33%
CHEMBL3194	P02766	Transthyretin	88.08%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	87.14%	89.62%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	86.63%	99.15%
CHEMBL4208	P20618	Proteasome component C5	86.56%	90.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.30%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.03%	95.56%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.37%	90.24%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.64%	96.09%
CHEMBL301	P24941	Cyclin-dependent kinase 2	82.02%	91.23%
CHEMBL2535	P11166	Glucose transporter	81.53%	98.75%

Plants that contains it

• Mucuna birdwoodiana

Cross-Links

• PubChem: 46177524
• LOTUS: LTS0173511
• wikiData: Q104991740