8aH-Benzo[3,4][2]benzopyrano[1,8-bc][1]benzopyran-4,11-diol, 8a-(2,4-dihydroxyphenyl)-6-(6-hydroxy-2-benzofuranyl)-2-methyl-, (8aR)-

Details

• Internal ID: 1d2d3561-d308-4914-a1c1-3efe0639d23c
• Taxonomy: Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
• IUPAC Name: (1R)-1-(2,4-dihydroxyphenyl)-17-(6-hydroxy-1-benzofuran-2-yl)-11-methyl-2,20-dioxapentacyclo[11.7.1.03,8.09,21.014,19]henicosa-3(8),4,6,9(21),10,12,14,16,18-nonaene-5,15-diol
• InChI: InChI=1S/C34H22O8/c1-16-8-23-22-6-4-21(37)15-30(22)41-34(25-7-5-19(35)13-26(25)38)33(23)24(9-16)32-27(39)10-18(12-31(32)42-34)28-11-17-2-3-20(36)14-29(17)40-28/h2-15,35-39H,1H3/t34-/m0/s1
• InChI Key: SMHBZVSVLIBGGO-UMSFTDKQSA-N
• Popularity: 2 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₂₂O₈
• Molecular Weight: 558.50 g/mol
• Exact Mass: 558.13146766 g/mol
• Topological Polar Surface Area (TPSA): 133.00 Ų
• XlogP: 6.70
• Atomic LogP (AlogP): 7.26
• H-Bond Acceptor: 8
• H-Bond Donor: 5
• Rotatable Bonds: 2

Synonyms

• (R)-8A-(2,4-dihydroxyphenyl)-6-(6-hydroxybenzofuran-2-yl)-2-methyl-8aH-benzo[3,4]isochromeno[1,8-bc]chromene-4,11-diol

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9208	92.08%
Caco-2	-	0.8097	80.97%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.5000	50.00%
Subcellular localzation	Mitochondria	0.7473	74.73%
OATP2B1 inhibitior	+	0.5745	57.45%
OATP1B1 inhibitior	+	0.8163	81.63%
OATP1B3 inhibitior	+	0.8151	81.51%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	+	0.8559	85.59%
P-glycoprotein inhibitior	+	0.8010	80.10%
P-glycoprotein substrate	+	0.6999	69.99%
CYP3A4 substrate	+	0.6468	64.68%
CYP2C9 substrate	-	0.6000	60.00%
CYP2D6 substrate	-	0.7508	75.08%
CYP3A4 inhibition	+	0.6225	62.25%
CYP2C9 inhibition	+	0.8590	85.90%
CYP2C19 inhibition	+	0.5830	58.30%
CYP2D6 inhibition	-	0.8796	87.96%
CYP1A2 inhibition	-	0.5548	55.48%
CYP2C8 inhibition	+	0.9040	90.40%
CYP inhibitory promiscuity	+	0.7368	73.68%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.3927	39.27%
Eye corrosion	-	0.9896	98.96%
Eye irritation	-	0.5765	57.65%
Skin irritation	-	0.6057	60.57%
Skin corrosion	-	0.9062	90.62%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7617	76.17%
Micronuclear	+	0.8300	83.00%
Hepatotoxicity	+	0.5167	51.67%
skin sensitisation	-	0.8771	87.71%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.6333	63.33%
Mitochondrial toxicity	+	0.5250	52.50%
Nephrotoxicity	+	0.4868	48.68%
Acute Oral Toxicity (c)	III	0.4473	44.73%
Estrogen receptor binding	+	0.9276	92.76%
Androgen receptor binding	+	0.8629	86.29%
Thyroid receptor binding	+	0.6815	68.15%
Glucocorticoid receptor binding	+	0.8901	89.01%
Aromatase binding	+	0.6829	68.29%
PPAR gamma	+	0.8477	84.77%
Honey bee toxicity	-	0.8152	81.52%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	+	0.5900	59.00%
Fish aquatic toxicity	+	0.9443	94.43%

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	98.84%	91.11%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.26%	89.00%
CHEMBL2581	P07339	Cathepsin D	93.24%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	93.11%	99.15%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.09%	94.00%
CHEMBL242	Q92731	Estrogen receptor beta	92.95%	98.35%
CHEMBL344	Q99705	Melanin-concentrating hormone receptor 1	90.72%	92.50%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	90.23%	99.23%
CHEMBL4208	P20618	Proteasome component C5	89.96%	90.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.14%	86.33%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	87.03%	95.78%
CHEMBL1966	Q02127	Dihydroorotate dehydrogenase	86.03%	96.09%
CHEMBL2041	P07949	Tyrosine-protein kinase receptor RET	86.02%	91.79%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.00%	95.56%
CHEMBL5966	P55899	IgG receptor FcRn large subunit p51	85.68%	90.93%
CHEMBL2337	P48067	Glycine transporter 1	85.09%	95.45%
CHEMBL1914	P06276	Butyrylcholinesterase	84.94%	95.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.61%	96.21%
CHEMBL2345	P51812	Ribosomal protein S6 kinase alpha 3	84.59%	95.64%
CHEMBL3492	P49721	Proteasome Macropain subunit	84.51%	90.24%
CHEMBL1811	P34995	Prostanoid EP1 receptor	83.76%	95.71%
CHEMBL3401	O75469	Pregnane X receptor	83.53%	94.73%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	83.43%	90.71%
CHEMBL3085	P43003	Excitatory amino acid transporter 1	83.21%	94.67%
CHEMBL2553	Q15418	Ribosomal protein S6 kinase alpha 1	82.61%	85.11%
CHEMBL2146302	O94925	Glutaminase kidney isoform, mitochondrial	81.20%	100.00%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	80.27%	96.67%
CHEMBL240	Q12809	HERG	80.18%	89.76%

Plants that contains it

• Morus alba

Cross-Links

• PubChem: 102384791
• LOTUS: LTS0169674
• wikiData: Q105255923