9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-3H-benzo[f][2]benzofuran-1-one

Details

• Internal ID: eafa80ad-9f1e-4e45-a5a2-95a964e5372a
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-(3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): CC1C(C(C(C(O1)OC2=C3COC(=O)C3=C(C4=CC(=C(C=C42)OC)OC)C5=CC6=C(C=C5)OCO6)O)O)O
• SMILES (Isomeric): CC1C(C(C(C(O1)OC2=C3COC(=O)C3=C(C4=CC(=C(C=C42)OC)OC)C5=CC6=C(C=C5)OCO6)O)O)O
• InChI: InChI=1S/C27H26O11/c1-11-22(28)23(29)24(30)27(37-11)38-25-14-8-18(33-3)17(32-2)7-13(14)20(21-15(25)9-34-26(21)31)12-4-5-16-19(6-12)36-10-35-16/h4-8,11,22-24,27-30H,9-10H2,1-3H3
• InChI Key: NLWUWPJUIJTHAN-UHFFFAOYSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₇H₂₆O₁₁
• Molecular Weight: 526.50 g/mol
• Exact Mass: 526.14751164 g/mol
• Topological Polar Surface Area (TPSA): 142.00 Ų
• XlogP: 2.30
• Atomic LogP (AlogP): 2.13
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

• SCHEMBL23060067

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8229	82.29%
Caco-2	-	0.7106	71.06%
Blood Brain Barrier	-	0.8750	87.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6747	67.47%
OATP2B1 inhibitior	-	0.8684	86.84%
OATP1B1 inhibitior	+	0.9247	92.47%
OATP1B3 inhibitior	+	0.9290	92.90%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.9176	91.76%
P-glycoprotein inhibitior	+	0.5841	58.41%
P-glycoprotein substrate	-	0.6963	69.63%
CYP3A4 substrate	+	0.6365	63.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8613	86.13%
CYP3A4 inhibition	+	0.6518	65.18%
CYP2C9 inhibition	-	0.6308	63.08%
CYP2C19 inhibition	+	0.5227	52.27%
CYP2D6 inhibition	-	0.8361	83.61%
CYP1A2 inhibition	-	0.8886	88.86%
CYP2C8 inhibition	+	0.5892	58.92%
CYP inhibitory promiscuity	+	0.7716	77.16%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5333	53.33%
Eye corrosion	-	0.9877	98.77%
Eye irritation	-	0.9270	92.70%
Skin irritation	-	0.8054	80.54%
Skin corrosion	-	0.9497	94.97%
Ames mutagenesis	+	0.6363	63.63%
Human Ether-a-go-go-Related Gene inhibition	-	0.4203	42.03%
Micronuclear	+	0.8474	84.74%
Hepatotoxicity	-	0.5750	57.50%
skin sensitisation	-	0.8397	83.97%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.7444	74.44%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6923	69.23%
Acute Oral Toxicity (c)	III	0.7285	72.85%
Estrogen receptor binding	+	0.8278	82.78%
Androgen receptor binding	+	0.5775	57.75%
Thyroid receptor binding	+	0.5710	57.10%
Glucocorticoid receptor binding	+	0.7646	76.46%
Aromatase binding	-	0.5637	56.37%
PPAR gamma	+	0.6443	64.43%
Honey bee toxicity	-	0.7417	74.17%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5049	50.49%
Fish aquatic toxicity	+	0.9143	91.43%

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	98.99%	91.11%
CHEMBL1951	P21397	Monoamine oxidase A	97.58%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	97.03%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	96.78%	89.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	95.98%	96.77%
CHEMBL2581	P07339	Cathepsin D	95.72%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.21%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.69%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	94.35%	94.80%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.05%	96.09%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	93.72%	94.45%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	93.46%	92.62%
CHEMBL2535	P11166	Glucose transporter	93.16%	98.75%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	90.81%	94.00%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.85%	97.36%
CHEMBL1994	P08235	Mineralocorticoid receptor	85.27%	100.00%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	84.90%	82.67%
CHEMBL3137262	O60341	LSD1/CoREST complex	84.16%	97.09%
CHEMBL4208	P20618	Proteasome component C5	83.00%	90.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.69%	95.53%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.67%	96.00%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	82.43%	92.38%
CHEMBL3060	Q9Y345	Glycine transporter 2	82.09%	99.17%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.87%	95.78%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.71%	97.14%
CHEMBL241	Q14432	Phosphodiesterase 3A	80.46%	92.94%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.31%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.00%	99.23%

Plants that contains it

• Justicia patentiflora

Cross-Links

• PubChem: 72976956
• LOTUS: LTS0276378
• wikiData: Q105181615