4-(3,4-dimethoxyphenyl)-6-hydroxy-5-methoxy-3H-benzo[f][2]benzofuran-1-one

Details

• Internal ID: ad310336-f961-4391-9a3e-72053929b2ad
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 4-(3,4-dimethoxyphenyl)-6-hydroxy-5-methoxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C(C=C(C=C1)C2=C3C(=CC4=C2COC4=O)C=CC(=C3OC)O)OC
• SMILES (Isomeric): COC1=C(C=C(C=C1)C2=C3C(=CC4=C2COC4=O)C=CC(=C3OC)O)OC
• InChI: InChI=1S/C21H18O6/c1-24-16-7-5-12(9-17(16)25-2)18-14-10-27-21(23)13(14)8-11-4-6-15(22)20(26-3)19(11)18/h4-9,22H,10H2,1-3H3
• InChI Key: HVHABCOASJFMNA-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₈O₆
• Molecular Weight: 366.40 g/mol
• Exact Mass: 366.11033829 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 3.80
• Atomic LogP (AlogP): 3.91
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9916	99.16%
Caco-2	+	0.8424	84.24%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8177	81.77%
OATP2B1 inhibitior	-	0.8652	86.52%
OATP1B1 inhibitior	+	0.9451	94.51%
OATP1B3 inhibitior	+	0.8663	86.63%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8907	89.07%
P-glycoprotein inhibitior	-	0.5198	51.98%
P-glycoprotein substrate	-	0.8538	85.38%
CYP3A4 substrate	+	0.5777	57.77%
CYP2C9 substrate	-	0.8021	80.21%
CYP2D6 substrate	-	0.8050	80.50%
CYP3A4 inhibition	+	0.5433	54.33%
CYP2C9 inhibition	+	0.9447	94.47%
CYP2C19 inhibition	+	0.7121	71.21%
CYP2D6 inhibition	-	0.8951	89.51%
CYP1A2 inhibition	+	0.7185	71.85%
CYP2C8 inhibition	+	0.6915	69.15%
CYP inhibitory promiscuity	+	0.7577	75.77%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9510	95.10%
Carcinogenicity (trinary)	Non-required	0.4433	44.33%
Eye corrosion	-	0.9874	98.74%
Eye irritation	-	0.5734	57.34%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9832	98.32%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6856	68.56%
Micronuclear	+	0.7633	76.33%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8944	89.44%
Respiratory toxicity	+	0.6222	62.22%
Reproductive toxicity	+	0.6556	65.56%
Mitochondrial toxicity	-	0.5250	52.50%
Nephrotoxicity	+	0.5255	52.55%
Acute Oral Toxicity (c)	III	0.5277	52.77%
Estrogen receptor binding	+	0.8824	88.24%
Androgen receptor binding	+	0.7756	77.56%
Thyroid receptor binding	+	0.7143	71.43%
Glucocorticoid receptor binding	+	0.9089	90.89%
Aromatase binding	-	0.5222	52.22%
PPAR gamma	+	0.8602	86.02%
Honey bee toxicity	-	0.8812	88.12%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5100	51.00%
Fish aquatic toxicity	+	0.9755	97.55%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	96.33%	94.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.55%	86.33%
CHEMBL2085	P14174	Macrophage migration inhibitory factor	94.61%	80.78%
CHEMBL2581	P07339	Cathepsin D	94.42%	98.95%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.55%	99.15%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	92.43%	98.21%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.10%	95.56%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.88%	91.11%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	91.75%	96.21%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.94%	96.09%
CHEMBL2535	P11166	Glucose transporter	89.65%	98.75%
CHEMBL4302	P08183	P-glycoprotein 1	87.92%	92.98%
CHEMBL3060	Q9Y345	Glycine transporter 2	87.39%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.33%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	87.08%	89.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.04%	99.23%
CHEMBL4208	P20618	Proteasome component C5	85.92%	90.00%
CHEMBL2708	Q16584	Mitogen-activated protein kinase kinase kinase 11	85.67%	81.14%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	85.61%	95.53%
CHEMBL5747	Q92793	CREB-binding protein	85.08%	95.12%
CHEMBL1951	P21397	Monoamine oxidase A	84.02%	91.49%
CHEMBL1907	P15144	Aminopeptidase N	83.86%	93.31%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	83.65%	96.67%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	83.33%	92.38%
CHEMBL1937	Q92769	Histone deacetylase 2	81.62%	94.75%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	81.44%	96.95%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.75%	95.78%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	80.59%	94.45%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	80.24%	85.00%
CHEMBL1255126	O15151	Protein Mdm4	80.06%	90.20%

Plants that contains it

• Vitex rotundifolia

Cross-Links

• PubChem: 11079065
• NPASS: NPC20619
• LOTUS: LTS0102325
• wikiData: Q105034256