9-(1,3-benzodioxol-5-yl)-4,7-dihydroxy-6-methoxy-3H-benzo[f][2]benzofuran-1-one

Details

• Internal ID: fff042da-6c88-4974-bb49-1d432a0dbd2c
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-4,7-dihydroxy-6-methoxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=C3COC(=O)C3=C2C4=CC5=C(C=C4)OCO5)O)O
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=C3COC(=O)C3=C2C4=CC5=C(C=C4)OCO5)O)O
• InChI: InChI=1S/C20H14O7/c1-24-15-6-11-10(5-13(15)21)17(18-12(19(11)22)7-25-20(18)23)9-2-3-14-16(4-9)27-8-26-14/h2-6,21-22H,7-8H2,1H3
• InChI Key: IFYIHGHEIRCOSQ-UHFFFAOYSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₀H₁₄O₇
• Molecular Weight: 366.30 g/mol
• Exact Mass: 366.07395278 g/mol
• Topological Polar Surface Area (TPSA): 94.40 Ų
• XlogP: 3.30
• Atomic LogP (AlogP): 3.33
• H-Bond Acceptor: 7
• H-Bond Donor: 2
• Rotatable Bonds: 2

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9846	98.46%
Caco-2	+	0.7198	71.98%
Blood Brain Barrier	-	0.7500	75.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.8078	80.78%
OATP2B1 inhibitior	-	0.7302	73.02%
OATP1B1 inhibitior	+	0.9178	91.78%
OATP1B3 inhibitior	+	0.9685	96.85%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.6790	67.90%
P-glycoprotein inhibitior	-	0.5378	53.78%
P-glycoprotein substrate	-	0.8633	86.33%
CYP3A4 substrate	+	0.5787	57.87%
CYP2C9 substrate	-	0.8012	80.12%
CYP2D6 substrate	-	0.8332	83.32%
CYP3A4 inhibition	+	0.6967	69.67%
CYP2C9 inhibition	+	0.9247	92.47%
CYP2C19 inhibition	+	0.9019	90.19%
CYP2D6 inhibition	-	0.7537	75.37%
CYP1A2 inhibition	-	0.7816	78.16%
CYP2C8 inhibition	+	0.5733	57.33%
CYP inhibitory promiscuity	+	0.7953	79.53%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9400	94.00%
Carcinogenicity (trinary)	Non-required	0.4149	41.49%
Eye corrosion	-	0.9876	98.76%
Eye irritation	+	0.6680	66.80%
Skin irritation	-	0.7687	76.87%
Skin corrosion	-	0.9554	95.54%
Ames mutagenesis	+	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6636	66.36%
Micronuclear	+	0.8874	88.74%
Hepatotoxicity	+	0.6000	60.00%
skin sensitisation	-	0.8055	80.55%
Respiratory toxicity	+	0.6889	68.89%
Reproductive toxicity	+	0.7556	75.56%
Mitochondrial toxicity	+	0.6875	68.75%
Nephrotoxicity	-	0.6314	63.14%
Acute Oral Toxicity (c)	III	0.7132	71.32%
Estrogen receptor binding	+	0.8972	89.72%
Androgen receptor binding	+	0.7291	72.91%
Thyroid receptor binding	+	0.6643	66.43%
Glucocorticoid receptor binding	+	0.8966	89.66%
Aromatase binding	+	0.5896	58.96%
PPAR gamma	+	0.8520	85.20%
Honey bee toxicity	-	0.8574	85.74%
Biodegradation	-	0.9000	90.00%
Crustacea aquatic toxicity	-	0.5749	57.49%
Fish aquatic toxicity	+	0.9493	94.93%

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	99.52%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.66%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	96.16%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.94%	86.33%
CHEMBL2581	P07339	Cathepsin D	95.88%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.87%	95.56%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.55%	85.14%
CHEMBL2002	P12268	Inosine-5'-monophosphate dehydrogenase 2	95.36%	98.21%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.00%	96.77%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.37%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.31%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.41%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	90.30%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.01%	96.09%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	88.77%	99.15%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	88.43%	80.96%
CHEMBL2292	Q13627	Dual-specificity tyrosine-phosphorylation regulated kinase 1A	86.85%	93.24%
CHEMBL1907	P15144	Aminopeptidase N	85.70%	93.31%
CHEMBL3438	Q05513	Protein kinase C zeta	85.32%	88.48%
CHEMBL2535	P11166	Glucose transporter	84.91%	98.75%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	83.46%	95.53%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.44%	99.23%
CHEMBL5608	Q16288	NT-3 growth factor receptor	83.04%	95.89%
CHEMBL2717	Q9HCR9	Phosphodiesterase 11A	81.88%	85.00%
CHEMBL4208	P20618	Proteasome component C5	81.31%	90.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	80.46%	82.67%
CHEMBL3060	Q9Y345	Glycine transporter 2	80.03%	99.17%

Plants that contains it

• Haplophyllum cappadocicum
• Haplophyllum myrtifolium
• Haplophyllum telephioides
• Phyllanthus oligospermus

Cross-Links

• PubChem: 101996845
• LOTUS: LTS0115320
• wikiData: Q104402670