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

Details

• Internal ID: 6c2be8ac-765c-4f7b-8241-29d37fb8bef3
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-6,7-dimethoxy-4-[(2R,3S,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=C3C(=C2OC4C(C(C(CO4)O)O)O)COC3=O)C5=CC6=C(C=C5)OCO6)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=C3C(=C2O[C@@H]4[C@H]([C@@H]([C@@H](CO4)O)O)O)COC3=O)C5=CC6=C(C=C5)OCO6)OC
• InChI: InChI=1S/C26H24O11/c1-31-17-6-12-13(7-18(17)32-2)24(37-26-23(29)22(28)15(27)9-34-26)14-8-33-25(30)21(14)20(12)11-3-4-16-19(5-11)36-10-35-16/h3-7,15,22-23,26-29H,8-10H2,1-2H3/t15-,22-,23+,26-/m1/s1
• InChI Key: AVYGDWFATMFGNJ-UVGWKVBGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₄O₁₁
• Molecular Weight: 512.50 g/mol
• Exact Mass: 512.13186158 g/mol
• Topological Polar Surface Area (TPSA): 142.00 Ų
• XlogP: 1.90
• Atomic LogP (AlogP): 1.74
• H-Bond Acceptor: 11
• H-Bond Donor: 3
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7658	76.58%
Caco-2	-	0.7115	71.15%
Blood Brain Barrier	-	0.7750	77.50%
Human oral bioavailability	-	0.6143	61.43%
Subcellular localzation	Mitochondria	0.6121	61.21%
OATP2B1 inhibitior	-	0.8682	86.82%
OATP1B1 inhibitior	+	0.9254	92.54%
OATP1B3 inhibitior	+	0.9423	94.23%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9500	95.00%
BSEP inhibitior	+	0.9313	93.13%
P-glycoprotein inhibitior	+	0.6114	61.14%
P-glycoprotein substrate	-	0.6589	65.89%
CYP3A4 substrate	+	0.6505	65.05%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8500	85.00%
CYP3A4 inhibition	+	0.5767	57.67%
CYP2C9 inhibition	-	0.8227	82.27%
CYP2C19 inhibition	-	0.7324	73.24%
CYP2D6 inhibition	-	0.8123	81.23%
CYP1A2 inhibition	-	0.9102	91.02%
CYP2C8 inhibition	+	0.5887	58.87%
CYP inhibitory promiscuity	-	0.6349	63.49%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5462	54.62%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9224	92.24%
Skin irritation	-	0.8073	80.73%
Skin corrosion	-	0.9419	94.19%
Ames mutagenesis	+	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.6878	68.78%
Micronuclear	+	0.8133	81.33%
Hepatotoxicity	+	0.5052	50.52%
skin sensitisation	-	0.8663	86.63%
Respiratory toxicity	+	0.6333	63.33%
Reproductive toxicity	+	0.9667	96.67%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	-	0.8144	81.44%
Acute Oral Toxicity (c)	III	0.7807	78.07%
Estrogen receptor binding	+	0.8217	82.17%
Androgen receptor binding	+	0.6505	65.05%
Thyroid receptor binding	+	0.5293	52.93%
Glucocorticoid receptor binding	+	0.8147	81.47%
Aromatase binding	-	0.6048	60.48%
PPAR gamma	+	0.6211	62.11%
Honey bee toxicity	-	0.6777	67.77%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.5549	55.49%
Fish aquatic toxicity	+	0.8011	80.11%

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	98.95%	91.11%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.64%	96.77%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.57%	85.14%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	96.96%	94.45%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	95.27%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.01%	89.00%
CHEMBL2535	P11166	Glucose transporter	94.75%	98.75%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.60%	92.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	94.60%	95.56%
CHEMBL2581	P07339	Cathepsin D	94.42%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.96%	86.33%
CHEMBL1951	P21397	Monoamine oxidase A	93.82%	91.49%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.37%	96.09%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.07%	94.00%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.27%	100.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	85.71%	95.53%
CHEMBL3137262	O60341	LSD1/CoREST complex	85.54%	97.09%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	84.40%	80.96%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	83.43%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.74%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	82.59%	89.62%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	81.68%	95.78%
CHEMBL4208	P20618	Proteasome component C5	80.70%	90.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.34%	95.89%

Plants that contains it

• Phyllanthus oligospermus

Cross-Links

• PubChem: 16082066
• LOTUS: LTS0156453
• wikiData: Q104919907