5-(6-Hydroxy-1-benzofuran-2-yl)-2-(5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-11-yl)benzene-1,3-diol

Details

• Internal ID: 03baba8e-af5e-4090-9fe9-5c7b3e327bc4
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: 5-(6-hydroxy-1-benzofuran-2-yl)-2-(5-hydroxy-9-methyl-8-oxatricyclo[7.3.1.02,7]trideca-2(7),3,5,10-tetraen-11-yl)benzene-1,3-diol
• InChI: InChI=1S/C27H22O6/c1-27-12-16(20-5-4-19(29)11-25(20)33-27)6-17(13-27)26-21(30)7-15(8-22(26)31)23-9-14-2-3-18(28)10-24(14)32-23/h2-5,7-11,13,16,28-31H,6,12H2,1H3
• InChI Key: ZVTKGVROAGDVCH-UHFFFAOYSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₂O₆
• Molecular Weight: 442.50 g/mol
• Exact Mass: 442.14163842 g/mol
• Topological Polar Surface Area (TPSA): 103.00 Ų
• XlogP: 4.80
• Atomic LogP (AlogP): 6.03
• H-Bond Acceptor: 6
• H-Bond Donor: 4
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9728	97.28%
Caco-2	-	0.7960	79.60%
Blood Brain Barrier	-	0.6129	61.29%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.6865	68.65%
OATP2B1 inhibitior	-	0.5707	57.07%
OATP1B1 inhibitior	+	0.8894	88.94%
OATP1B3 inhibitior	+	0.9583	95.83%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.8250	82.50%
BSEP inhibitior	+	0.8495	84.95%
P-glycoprotein inhibitior	+	0.7215	72.15%
P-glycoprotein substrate	+	0.7001	70.01%
CYP3A4 substrate	+	0.6542	65.42%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.6679	66.79%
CYP3A4 inhibition	+	0.5302	53.02%
CYP2C9 inhibition	+	0.7416	74.16%
CYP2C19 inhibition	+	0.6393	63.93%
CYP2D6 inhibition	-	0.8708	87.08%
CYP1A2 inhibition	+	0.5879	58.79%
CYP2C8 inhibition	+	0.8643	86.43%
CYP inhibitory promiscuity	+	0.8923	89.23%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Danger	0.4573	45.73%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.7562	75.62%
Skin irritation	-	0.7166	71.66%
Skin corrosion	-	0.9107	91.07%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8384	83.84%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	-	0.7287	72.87%
skin sensitisation	-	0.7930	79.30%
Respiratory toxicity	+	0.5556	55.56%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.6056	60.56%
Acute Oral Toxicity (c)	I	0.4172	41.72%
Estrogen receptor binding	+	0.8741	87.41%
Androgen receptor binding	+	0.8426	84.26%
Thyroid receptor binding	+	0.6269	62.69%
Glucocorticoid receptor binding	+	0.8827	88.27%
Aromatase binding	+	0.7018	70.18%
PPAR gamma	+	0.8273	82.73%
Honey bee toxicity	-	0.8460	84.60%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	+	0.6300	63.00%
Fish aquatic toxicity	+	0.9858	98.58%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	140 nM	IC50	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.35%	91.11%
CHEMBL2581	P07339	Cathepsin D	93.48%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.34%	99.15%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	92.28%	85.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	92.07%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.88%	96.09%
CHEMBL1914	P06276	Butyrylcholinesterase	91.16%	95.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	90.60%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.46%	89.00%
CHEMBL236	P41143	Delta opioid receptor	89.26%	99.35%
CHEMBL242	Q92731	Estrogen receptor beta	88.51%	98.35%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.21%	86.33%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	85.75%	99.23%
CHEMBL5408	Q9UHD2	Serine/threonine-protein kinase TBK1	84.96%	90.48%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	83.89%	92.50%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	83.45%	95.78%
CHEMBL217	P14416	Dopamine D2 receptor	83.23%	95.62%
CHEMBL284	P27487	Dipeptidyl peptidase IV	82.97%	95.69%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.59%	100.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	81.57%	94.00%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.85%	90.71%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.74%	96.21%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.66%	100.00%

Plants that contains it

• Morus alba
• Morus mongolica

Cross-Links

• PubChem: 21636209
• LOTUS: LTS0088402
• wikiData: Q105384633