4-(1,3-benzodioxol-5-yl)-6-hydroxy-9-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one

Details

• Internal ID: aa3e3767-06a7-4e6e-86dd-a8fba8527a6f
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 4-(1,3-benzodioxol-5-yl)-6-hydroxy-9-methoxy-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C2C(=C(C3=C1C=CC(=C3OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC6=C(C=C5)OCO6)COC2=O
• SMILES (Isomeric): COC1=C2C(=C(C3=C1C=CC(=C3O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC6=C(C=C5)OCO6)COC2=O
• InChI: InChI=1S/C26H24O12/c1-33-23-11-3-4-13(28)24(38-26-22(31)21(30)20(29)16(7-27)37-26)18(11)17(12-8-34-25(32)19(12)23)10-2-5-14-15(6-10)36-9-35-14/h2-6,16,20-22,26-31H,7-9H2,1H3/t16-,20-,21+,22-,26+/m1/s1
• InChI Key: GTJWRKJAJFCZJJ-DMRYIZGCSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₂₄O₁₂
• Molecular Weight: 528.50 g/mol
• Exact Mass: 528.12677620 g/mol
• Topological Polar Surface Area (TPSA): 174.00 Ų
• XlogP: 1.50
• Atomic LogP (AlogP): 0.80
• H-Bond Acceptor: 12
• H-Bond Donor: 5
• Rotatable Bonds: 5

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6191	61.91%
Caco-2	-	0.8681	86.81%
Blood Brain Barrier	-	0.7250	72.50%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6374	63.74%
OATP2B1 inhibitior	-	0.8494	84.94%
OATP1B1 inhibitior	+	0.9026	90.26%
OATP1B3 inhibitior	+	0.9728	97.28%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7982	79.82%
P-glycoprotein inhibitior	-	0.5663	56.63%
P-glycoprotein substrate	-	0.6848	68.48%
CYP3A4 substrate	+	0.6550	65.50%
CYP2C9 substrate	-	0.8175	81.75%
CYP2D6 substrate	-	0.8558	85.58%
CYP3A4 inhibition	-	0.5836	58.36%
CYP2C9 inhibition	-	0.7784	77.84%
CYP2C19 inhibition	-	0.7015	70.15%
CYP2D6 inhibition	-	0.8616	86.16%
CYP1A2 inhibition	-	0.9048	90.48%
CYP2C8 inhibition	+	0.5854	58.54%
CYP inhibitory promiscuity	+	0.6208	62.08%
UGT catelyzed	-	0.7000	70.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5596	55.96%
Eye corrosion	-	0.9899	98.99%
Eye irritation	-	0.9200	92.00%
Skin irritation	-	0.8137	81.37%
Skin corrosion	-	0.9475	94.75%
Ames mutagenesis	+	0.6800	68.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.3939	39.39%
Micronuclear	+	0.7033	70.33%
Hepatotoxicity	-	0.5125	51.25%
skin sensitisation	-	0.8847	88.47%
Respiratory toxicity	+	0.6778	67.78%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7125	71.25%
Nephrotoxicity	-	0.6014	60.14%
Acute Oral Toxicity (c)	III	0.7562	75.62%
Estrogen receptor binding	+	0.7977	79.77%
Androgen receptor binding	+	0.6465	64.65%
Thyroid receptor binding	-	0.5233	52.33%
Glucocorticoid receptor binding	+	0.7038	70.38%
Aromatase binding	-	0.5456	54.56%
PPAR gamma	+	0.6690	66.90%
Honey bee toxicity	-	0.7322	73.22%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.7290	72.90%

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	99.95%	91.11%
CHEMBL2581	P07339	Cathepsin D	98.52%	98.95%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.03%	94.45%
CHEMBL1951	P21397	Monoamine oxidase A	97.99%	91.49%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.60%	85.14%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	97.40%	94.80%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.98%	89.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.05%	96.09%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	94.42%	96.77%
CHEMBL1293249	Q13887	Kruppel-like factor 5	93.37%	86.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.18%	95.56%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	92.20%	99.15%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	92.14%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	91.41%	94.00%
CHEMBL3137262	O60341	LSD1/CoREST complex	88.78%	97.09%
CHEMBL3401	O75469	Pregnane X receptor	86.23%	94.73%
CHEMBL1994	P08235	Mineralocorticoid receptor	86.16%	100.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	84.51%	99.17%
CHEMBL2535	P11166	Glucose transporter	83.94%	98.75%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	83.25%	96.21%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	82.35%	95.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.70%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	80.60%	99.23%

Plants that contains it

• Justicia hyssopifolia

Cross-Links

• PubChem: 162933115
• LOTUS: LTS0085260
• wikiData: Q105018918