9-(3,4-dimethoxyphenyl)-5-hydroxy-6H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one

Details

• Internal ID: f50ce642-f90b-410b-86a4-346c3822ffd1
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 9-(3,4-dimethoxyphenyl)-5-hydroxy-6H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=C3C(=C(C4=CC5=C(C=C42)OCO5)O)COC3=O)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=C3C(=C(C4=CC5=C(C=C42)OCO5)O)COC3=O)OC
• InChI: InChI=1S/C21H16O7/c1-24-14-4-3-10(5-15(14)25-2)18-11-6-16-17(28-9-27-16)7-12(11)20(22)13-8-26-21(23)19(13)18/h3-7,22H,8-9H2,1-2H3
• InChI Key: ZYUVOQCJYNAWNV-UHFFFAOYSA-N
• Popularity: 4 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₆O₇
• Molecular Weight: 380.30 g/mol
• Exact Mass: 380.08960285 g/mol
• Topological Polar Surface Area (TPSA): 83.40 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.63
• H-Bond Acceptor: 7
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 53965-06-3
• 9-(3,4-dimethoxyphenyl)-5-hydroxy-6H-[2]benzofuro[5,6-f][1,3]benzodioxol-8-one
• LIGNAN DERIV
• CHEMBL495476
• SCHEMBL4096679
• DTXSID90318383
• NSC329490
• NSC-329490
• 5-(3,4-Dimethoxy-phenyl)-9-hydroxy-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one
• 9-(3,4-dimethoxyphenyl)-5-hydroxy-6H-isobenzofuro[5,6-f][1,3]benzodioxol-8-one
• Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(8H)-one, 5-(3,4-dimethoxyphenyl)-9-hydroxy-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9886	98.86%
Caco-2	+	0.8086	80.86%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7932	79.32%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9313	93.13%
OATP1B3 inhibitior	+	0.9665	96.65%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.7986	79.86%
P-glycoprotein inhibitior	-	0.4298	42.98%
P-glycoprotein substrate	-	0.8460	84.60%
CYP3A4 substrate	+	0.5627	56.27%
CYP2C9 substrate	-	0.8012	80.12%
CYP2D6 substrate	-	0.8332	83.32%
CYP3A4 inhibition	+	0.8578	85.78%
CYP2C9 inhibition	+	0.9389	93.89%
CYP2C19 inhibition	+	0.9332	93.32%
CYP2D6 inhibition	-	0.7537	75.37%
CYP1A2 inhibition	-	0.8550	85.50%
CYP2C8 inhibition	+	0.6093	60.93%
CYP inhibitory promiscuity	+	0.7841	78.41%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4425	44.25%
Eye corrosion	-	0.9871	98.71%
Eye irritation	-	0.6089	60.89%
Skin irritation	-	0.7847	78.47%
Skin corrosion	-	0.9655	96.55%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.5686	56.86%
Micronuclear	+	0.8974	89.74%
Hepatotoxicity	+	0.6250	62.50%
skin sensitisation	-	0.7316	73.16%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6125	61.25%
Nephrotoxicity	-	0.5758	57.58%
Acute Oral Toxicity (c)	III	0.6180	61.80%
Estrogen receptor binding	+	0.8999	89.99%
Androgen receptor binding	+	0.7264	72.64%
Thyroid receptor binding	+	0.7366	73.66%
Glucocorticoid receptor binding	+	0.9173	91.73%
Aromatase binding	+	0.5597	55.97%
PPAR gamma	+	0.7751	77.51%
Honey bee toxicity	-	0.8771	87.71%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.9563	95.63%

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	98.27%	91.11%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	97.50%	98.21%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.61%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.88%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.40%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.46%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.73%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	92.39%	91.49%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	92.04%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.84%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	89.45%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.06%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	88.15%	96.09%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	86.87%	85.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	84.79%	96.21%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.65%	95.89%
CHEMBL3438	Q05513	Protein kinase C zeta	83.74%	88.48%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	83.27%	92.38%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.47%	96.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.40%	99.23%
CHEMBL2535	P11166	Glucose transporter	81.09%	98.75%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.54%	99.17%
CHEMBL4208	P20618	Proteasome component C5	80.08%	90.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	80.02%	94.80%

Plants that contains it

• Bupleurum scorzonerifolium
• Justicia procumbens
• Monechma ciliatum
• Polygala chinensis

Cross-Links

• PubChem: 332529
• NPASS: NPC116838
• ChEMBL: CHEMBL495476
• LOTUS: LTS0052024
• wikiData: Q82073936