2-[4-Hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]-1-benzofuran-6-ol

Details

• Internal ID: dcc4c8cf-7268-426e-b24d-021e93a8d75a
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 2-[4-hydroxy-2-methoxy-3-(3-methylbut-2-enyl)phenyl]-1-benzofuran-6-ol
• SMILES (Canonical): CC(=CCC1=C(C=CC(=C1OC)C2=CC3=C(O2)C=C(C=C3)O)O)C
• SMILES (Isomeric): CC(=CCC1=C(C=CC(=C1OC)C2=CC3=C(O2)C=C(C=C3)O)O)C
• InChI: InChI=1S/C20H20O4/c1-12(2)4-7-15-17(22)9-8-16(20(15)23-3)19-10-13-5-6-14(21)11-18(13)24-19/h4-6,8-11,21-22H,7H2,1-3H3
• InChI Key: LEQYRAKNFDFXHE-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₂₀O₄
• Molecular Weight: 324.40 g/mol
• Exact Mass: 324.13615911 g/mol
• Topological Polar Surface Area (TPSA): 62.80 Ų
• XlogP: 5.20
• Atomic LogP (AlogP): 5.03
• H-Bond Acceptor: 4
• H-Bond Donor: 2
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9964	99.64%
Caco-2	+	0.6594	65.94%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7260	72.60%
OATP2B1 inhibitior	+	0.5635	56.35%
OATP1B1 inhibitior	+	0.7935	79.35%
OATP1B3 inhibitior	+	0.8724	87.24%
MATE1 inhibitior	-	0.8600	86.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8707	87.07%
P-glycoprotein inhibitior	+	0.5817	58.17%
P-glycoprotein substrate	-	0.5218	52.18%
CYP3A4 substrate	+	0.5383	53.83%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.4182	41.82%
CYP3A4 inhibition	-	0.6225	62.25%
CYP2C9 inhibition	+	0.9000	90.00%
CYP2C19 inhibition	+	0.9021	90.21%
CYP2D6 inhibition	-	0.7016	70.16%
CYP1A2 inhibition	+	0.8626	86.26%
CYP2C8 inhibition	+	0.6330	63.30%
CYP inhibitory promiscuity	+	0.9761	97.61%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.4689	46.89%
Eye corrosion	-	0.9910	99.10%
Eye irritation	-	0.4799	47.99%
Skin irritation	-	0.8108	81.08%
Skin corrosion	-	0.9509	95.09%
Ames mutagenesis	+	0.5200	52.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7429	74.29%
Micronuclear	+	0.5300	53.00%
Hepatotoxicity	+	0.5375	53.75%
skin sensitisation	-	0.7831	78.31%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.7759	77.59%
Acute Oral Toxicity (c)	III	0.5833	58.33%
Estrogen receptor binding	+	0.9117	91.17%
Androgen receptor binding	+	0.8598	85.98%
Thyroid receptor binding	+	0.7724	77.24%
Glucocorticoid receptor binding	+	0.9292	92.92%
Aromatase binding	+	0.7746	77.46%
PPAR gamma	+	0.9434	94.34%
Honey bee toxicity	-	0.8721	87.21%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5700	57.00%
Fish aquatic toxicity	+	0.9961	99.61%

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	99.10%	91.11%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	95.01%	96.95%
CHEMBL2581	P07339	Cathepsin D	91.97%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	91.40%	99.15%
CHEMBL1293249	Q13887	Kruppel-like factor 5	91.23%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.19%	99.17%
CHEMBL242	Q92731	Estrogen receptor beta	90.16%	98.35%
CHEMBL3401	O75469	Pregnane X receptor	88.29%	94.73%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.86%	94.00%
CHEMBL4208	P20618	Proteasome component C5	85.90%	90.00%
CHEMBL3492	P49721	Proteasome Macropain subunit	85.69%	90.24%
CHEMBL4657	Q6V1X1	Dipeptidyl peptidase VIII	85.64%	97.21%
CHEMBL1951	P21397	Monoamine oxidase A	84.88%	91.49%
CHEMBL1163101	O75460	Serine/threonine-protein kinase/endoribonuclease IRE1	84.00%	98.11%
CHEMBL3194	P02766	Transthyretin	83.17%	90.71%

Plants that contains it

• Erythrina bidwillii
• Erythrina variegata

Cross-Links

• PubChem: 10019143
• LOTUS: LTS0267727
• wikiData: Q105150738