4-(1,3-Benzodioxol-5-yl)-6,7-dimethoxybenzo[f][1]benzofuran-3-one

Details

• Internal ID: 20ce6806-79c1-41f5-8e2c-49e2e29d3cde
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 4-(1,3-benzodioxol-5-yl)-6,7-dimethoxybenzo[f][1]benzofuran-3-one
• SMILES (Canonical): COC1=CC2=CC3=C(C(=O)CO3)C(=C2C=C1OC)C4=CC5=C(C=C4)OCO5
• SMILES (Isomeric): COC1=CC2=CC3=C(C(=O)CO3)C(=C2C=C1OC)C4=CC5=C(C=C4)OCO5
• InChI: InChI=1S/C21H16O6/c1-23-16-6-12-7-19-21(14(22)9-25-19)20(13(12)8-17(16)24-2)11-3-4-15-18(5-11)27-10-26-15/h3-8H,9-10H2,1-2H3
• InChI Key: VKHANCMHYATJMZ-UHFFFAOYSA-N
• Popularity: 6 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₁H₁₆O₆
• Molecular Weight: 364.30 g/mol
• Exact Mass: 364.09468823 g/mol
• Topological Polar Surface Area (TPSA): 63.20 Ų
• XlogP: 4.10
• Atomic LogP (AlogP): 3.83
• H-Bond Acceptor: 6
• H-Bond Donor: 0
• Rotatable Bonds: 3

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9922	99.22%
Caco-2	+	0.8573	85.73%
Blood Brain Barrier	+	0.6500	65.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7509	75.09%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9368	93.68%
OATP1B3 inhibitior	+	0.9573	95.73%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8754	87.54%
P-glycoprotein inhibitior	+	0.7675	76.75%
P-glycoprotein substrate	-	0.8493	84.93%
CYP3A4 substrate	+	0.5195	51.95%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7804	78.04%
CYP3A4 inhibition	+	0.9004	90.04%
CYP2C9 inhibition	+	0.9227	92.27%
CYP2C19 inhibition	+	0.9586	95.86%
CYP2D6 inhibition	+	0.5144	51.44%
CYP1A2 inhibition	-	0.7148	71.48%
CYP2C8 inhibition	-	0.5595	55.95%
CYP inhibitory promiscuity	+	0.9236	92.36%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4083	40.83%
Eye corrosion	-	0.9840	98.40%
Eye irritation	-	0.6576	65.76%
Skin irritation	-	0.8303	83.03%
Skin corrosion	-	0.9670	96.70%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6594	65.94%
Micronuclear	+	0.7833	78.33%
Hepatotoxicity	+	0.6375	63.75%
skin sensitisation	-	0.5436	54.36%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	+	0.5768	57.68%
Acute Oral Toxicity (c)	III	0.6978	69.78%
Estrogen receptor binding	+	0.8724	87.24%
Androgen receptor binding	+	0.7268	72.68%
Thyroid receptor binding	+	0.6898	68.98%
Glucocorticoid receptor binding	+	0.9110	91.10%
Aromatase binding	+	0.5996	59.96%
PPAR gamma	+	0.7121	71.21%
Honey bee toxicity	-	0.7747	77.47%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	+	0.5500	55.00%
Fish aquatic toxicity	+	0.9369	93.69%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.16%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.09%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.43%	94.45%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.36%	91.11%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.70%	86.33%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.66%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.12%	92.62%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	91.22%	92.38%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.96%	94.00%
CHEMBL2581	P07339	Cathepsin D	90.30%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.29%	95.56%
CHEMBL1937	Q92769	Histone deacetylase 2	88.78%	94.75%
CHEMBL1907	P15144	Aminopeptidase N	87.86%	93.31%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	87.31%	96.00%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	86.28%	80.96%
CHEMBL2535	P11166	Glucose transporter	84.63%	98.75%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	84.41%	85.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.15%	89.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	83.28%	95.53%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	83.07%	82.67%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.80%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	82.53%	96.09%
CHEMBL4224	P49759	Dual specificty protein kinase CLK1	82.31%	85.30%
CHEMBL4040	P28482	MAP kinase ERK2	81.72%	83.82%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.27%	95.78%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	81.21%	99.23%

Plants that contains it

• Boenninghausenia albiflora
• Hypoestes purpurea
• Justicia procumbens

Cross-Links

• PubChem: 44365806
• NPASS: NPC65784
• ChEMBL: CHEMBL149056
• LOTUS: LTS0132005
• wikiData: Q105287742