5-[5-(3-Hydroxy-3-methylbutyl)-6-methoxy-1-benzofuran-2-yl]benzene-1,3-diol

Details

• Internal ID: d9f9b1e2-0176-4627-a7d3-e6fe780fe8d3
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-[5-(3-hydroxy-3-methylbutyl)-6-methoxy-1-benzofuran-2-yl]benzene-1,3-diol
• SMILES (Canonical): CC(C)(CCC1=C(C=C2C(=C1)C=C(O2)C3=CC(=CC(=C3)O)O)OC)O
• SMILES (Isomeric): CC(C)(CCC1=C(C=C2C(=C1)C=C(O2)C3=CC(=CC(=C3)O)O)OC)O
• InChI: InChI=1S/C20H22O5/c1-20(2,23)5-4-12-6-13-9-18(25-19(13)11-17(12)24-3)14-7-15(21)10-16(22)8-14/h6-11,21-23H,4-5H2,1-3H3
• InChI Key: VYAUAPDLFZUPJK-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₂O₅
• Molecular Weight: 342.40 g/mol
• Exact Mass: 342.14672380 g/mol
• Topological Polar Surface Area (TPSA): 83.10 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 4.22
• H-Bond Acceptor: 5
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9906	99.06%
Caco-2	+	0.7388	73.88%
Blood Brain Barrier	+	0.5500	55.00%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6759	67.59%
OATP2B1 inhibitior	-	0.7124	71.24%
OATP1B1 inhibitior	+	0.8750	87.50%
OATP1B3 inhibitior	+	0.8901	89.01%
MATE1 inhibitior	-	0.9000	90.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.8713	87.13%
P-glycoprotein inhibitior	-	0.5591	55.91%
P-glycoprotein substrate	-	0.5409	54.09%
CYP3A4 substrate	+	0.5458	54.58%
CYP2C9 substrate	-	0.5960	59.60%
CYP2D6 substrate	+	0.3973	39.73%
CYP3A4 inhibition	-	0.5353	53.53%
CYP2C9 inhibition	-	0.6223	62.23%
CYP2C19 inhibition	-	0.7516	75.16%
CYP2D6 inhibition	-	0.8732	87.32%
CYP1A2 inhibition	-	0.5495	54.95%
CYP2C8 inhibition	+	0.7959	79.59%
CYP inhibitory promiscuity	+	0.5790	57.90%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.8800	88.00%
Carcinogenicity (trinary)	Non-required	0.5619	56.19%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.6901	69.01%
Skin irritation	-	0.7798	77.98%
Skin corrosion	-	0.9277	92.77%
Ames mutagenesis	-	0.6770	67.70%
Human Ether-a-go-go-Related Gene inhibition	+	0.9346	93.46%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.6174	61.74%
skin sensitisation	-	0.8604	86.04%
Respiratory toxicity	-	0.6000	60.00%
Reproductive toxicity	+	0.8111	81.11%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	-	0.6166	61.66%
Acute Oral Toxicity (c)	III	0.4222	42.22%
Estrogen receptor binding	+	0.9350	93.50%
Androgen receptor binding	+	0.6155	61.55%
Thyroid receptor binding	+	0.7089	70.89%
Glucocorticoid receptor binding	+	0.8018	80.18%
Aromatase binding	+	0.7794	77.94%
PPAR gamma	+	0.8806	88.06%
Honey bee toxicity	-	0.8377	83.77%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.5451	54.51%
Fish aquatic toxicity	+	0.9587	95.87%

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	98.49%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.65%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.85%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.30%	99.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.09%	96.09%
CHEMBL2581	P07339	Cathepsin D	87.53%	98.95%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	87.19%	96.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	86.72%	85.14%
CHEMBL3401	O75469	Pregnane X receptor	84.31%	94.73%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	83.23%	92.62%

Plants that contains it

• Bagassa guianensis

Cross-Links

• PubChem: 102048879
• LOTUS: LTS0014702
• wikiData: Q105298866