8-(1,3-benzodioxol-5-yl)-5-hydroxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one

Details

• Internal ID: 646a2816-6142-4151-a5d0-135563a9094f
• Taxonomy: Organoheterocyclic compounds > Naphthofurans
• IUPAC Name: 8-(1,3-benzodioxol-5-yl)-5-hydroxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C(C2=C(C=C3COC(=O)C3=C2)C(=C1OC)O)C4=CC5=C(C=C4)OCO5
• SMILES (Isomeric): COC1=C(C2=C(C=C3COC(=O)C3=C2)C(=C1OC)O)C4=CC5=C(C=C4)OCO5
• InChI: InChI=1S/C21H16O7/c1-24-19-17(10-3-4-15-16(6-10)28-9-27-15)13-7-12-11(8-26-21(12)23)5-14(13)18(22)20(19)25-2/h3-7,22H,8-9H2,1-2H3
• InChI Key: OJFWWEKUZOACPB-UHFFFAOYSA-N
• Popularity: 0 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

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9865	98.65%
Caco-2	+	0.7066	70.66%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5143	51.43%
Subcellular localzation	Mitochondria	0.7876	78.76%
OATP2B1 inhibitior	-	0.8682	86.82%
OATP1B1 inhibitior	+	0.8903	89.03%
OATP1B3 inhibitior	+	0.9539	95.39%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8877	88.77%
P-glycoprotein inhibitior	+	0.5934	59.34%
P-glycoprotein substrate	-	0.8245	82.45%
CYP3A4 substrate	+	0.6216	62.16%
CYP2C9 substrate	-	0.8012	80.12%
CYP2D6 substrate	-	0.8332	83.32%
CYP3A4 inhibition	+	0.8608	86.08%
CYP2C9 inhibition	+	0.9479	94.79%
CYP2C19 inhibition	+	0.9331	93.31%
CYP2D6 inhibition	+	0.5000	50.00%
CYP1A2 inhibition	-	0.8380	83.80%
CYP2C8 inhibition	+	0.5106	51.06%
CYP inhibitory promiscuity	+	0.8569	85.69%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9300	93.00%
Carcinogenicity (trinary)	Non-required	0.4107	41.07%
Eye corrosion	-	0.9868	98.68%
Eye irritation	-	0.6382	63.82%
Skin irritation	-	0.7831	78.31%
Skin corrosion	-	0.9685	96.85%
Ames mutagenesis	+	0.5900	59.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6471	64.71%
Micronuclear	+	0.8874	88.74%
Hepatotoxicity	+	0.6698	66.98%
skin sensitisation	-	0.6947	69.47%
Respiratory toxicity	+	0.7333	73.33%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.6000	60.00%
Nephrotoxicity	-	0.6206	62.06%
Acute Oral Toxicity (c)	III	0.6221	62.21%
Estrogen receptor binding	+	0.9251	92.51%
Androgen receptor binding	+	0.6387	63.87%
Thyroid receptor binding	+	0.6639	66.39%
Glucocorticoid receptor binding	+	0.8807	88.07%
Aromatase binding	+	0.8111	81.11%
PPAR gamma	+	0.8161	81.61%
Honey bee toxicity	-	0.8757	87.57%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.9535	95.35%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL1951	P21397	Monoamine oxidase A	99.29%	91.49%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	99.06%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.10%	98.95%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.51%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.51%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.15%	95.56%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	94.72%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.11%	89.00%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.45%	94.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	90.78%	85.14%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	90.72%	92.62%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.36%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	88.66%	94.80%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	88.52%	98.21%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	88.11%	80.96%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.56%	99.23%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	85.90%	93.24%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	85.49%	99.15%
CHEMBL3438	Q05513	Protein kinase C zeta	84.89%	88.48%
CHEMBL1929	P47989	Xanthine dehydrogenase	84.66%	96.12%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.68%	96.21%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.18%	96.00%
CHEMBL2535	P11166	Glucose transporter	83.09%	98.75%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.55%	95.89%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	81.58%	95.53%
CHEMBL1994	P08235	Mineralocorticoid receptor	80.93%	100.00%
CHEMBL2056	P21728	Dopamine D1 receptor	80.81%	91.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.49%	82.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.39%	99.17%

Plants that contains it

• Haplophyllum tuberculatum

Cross-Links

• PubChem: 162997063
• LOTUS: LTS0125326
• wikiData: Q105193063