4-(1,3-benzodioxol-5-yl)-7-hydroxy-6-methoxy-1H-benzo[f][2]benzofuran-3-one

Details

• Internal ID: e0cdf0be-0924-4291-825d-f69fa0555363
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 4-(1,3-benzodioxol-5-yl)-7-hydroxy-6-methoxy-1H-benzo[f][2]benzofuran-3-one
• SMILES (Canonical): COC1=CC2=C(C3=C(COC3=O)C=C2C=C1O)C4=CC5=C(C=C4)OCO5
• SMILES (Isomeric): COC1=CC2=C(C3=C(COC3=O)C=C2C=C1O)C4=CC5=C(C=C4)OCO5
• InChI: InChI=1S/C20H14O6/c1-23-16-7-13-11(5-14(16)21)4-12-8-24-20(22)19(12)18(13)10-2-3-15-17(6-10)26-9-25-15/h2-7,21H,8-9H2,1H3
• InChI Key: QGNYAXUXBZUMPS-UHFFFAOYSA-N
• Popularity: 5 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₄O₆
• Molecular Weight: 350.30 g/mol
• Exact Mass: 350.07903816 g/mol
• Topological Polar Surface Area (TPSA): 74.20 Ų
• XlogP: 3.70
• Atomic LogP (AlogP): 3.62
• H-Bond Acceptor: 6
• H-Bond Donor: 1
• Rotatable Bonds: 2

Synonyms

• AKOS004110705

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9905	99.05%
Caco-2	+	0.7377	73.77%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	+	0.5143	51.43%
Subcellular localzation	Mitochondria	0.8228	82.28%
OATP2B1 inhibitior	-	0.8659	86.59%
OATP1B1 inhibitior	+	0.9291	92.91%
OATP1B3 inhibitior	+	0.9727	97.27%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8630	86.30%
P-glycoprotein inhibitior	-	0.6204	62.04%
P-glycoprotein substrate	-	0.8622	86.22%
CYP3A4 substrate	+	0.5573	55.73%
CYP2C9 substrate	-	0.8012	80.12%
CYP2D6 substrate	-	0.8332	83.32%
CYP3A4 inhibition	+	0.8291	82.91%
CYP2C9 inhibition	+	0.9545	95.45%
CYP2C19 inhibition	+	0.9104	91.04%
CYP2D6 inhibition	+	0.5133	51.33%
CYP1A2 inhibition	-	0.5481	54.81%
CYP2C8 inhibition	+	0.4805	48.05%
CYP inhibitory promiscuity	+	0.8458	84.58%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9200	92.00%
Carcinogenicity (trinary)	Warning	0.4194	41.94%
Eye corrosion	-	0.9848	98.48%
Eye irritation	-	0.5123	51.23%
Skin irritation	-	0.7410	74.10%
Skin corrosion	-	0.9602	96.02%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7480	74.80%
Micronuclear	+	0.8474	84.74%
Hepatotoxicity	+	0.5823	58.23%
skin sensitisation	-	0.7705	77.05%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5970	59.70%
Acute Oral Toxicity (c)	III	0.7061	70.61%
Estrogen receptor binding	+	0.9401	94.01%
Androgen receptor binding	+	0.7934	79.34%
Thyroid receptor binding	+	0.6165	61.65%
Glucocorticoid receptor binding	+	0.9013	90.13%
Aromatase binding	+	0.6906	69.06%
PPAR gamma	+	0.7752	77.52%
Honey bee toxicity	-	0.8497	84.97%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5649	56.49%
Fish aquatic toxicity	+	0.9500	95.00%

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	99.35%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	98.54%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	97.55%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	96.81%	91.49%
CHEMBL2581	P07339	Cathepsin D	95.82%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.46%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.31%	95.56%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.58%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	92.86%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	89.33%	96.77%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.51%	99.15%
CHEMBL2535	P11166	Glucose transporter	88.27%	98.75%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.67%	99.23%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.10%	96.09%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.75%	89.00%
CHEMBL240	Q12809	HERG	84.62%	89.76%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	83.52%	98.21%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.43%	82.67%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	83.29%	95.53%
CHEMBL1937	Q92769	Histone deacetylase 2	82.89%	94.75%
CHEMBL3401	O75469	Pregnane X receptor	82.70%	94.73%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	82.59%	95.50%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	82.26%	96.00%
CHEMBL1907	P15144	Aminopeptidase N	82.13%	93.31%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	81.91%	94.80%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.44%	99.17%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	81.29%	92.38%
CHEMBL5543	Q9Y463	Dual specificity tyrosine-phosphorylation-regulated kinase 1B	80.52%	94.70%

Plants that contains it

• Haplophyllum cappadocicum
• Haplophyllum dauricum

Cross-Links

• PubChem: 14704582
• LOTUS: LTS0193389
• wikiData: Q104394587