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

Details

• Internal ID: 1fde5bcc-3175-4f64-bc17-c964886f408c
• Taxonomy: Lignans, neolignans and related compounds > Arylnaphthalene lignans
• IUPAC Name: (3S)-9-(1,3-benzodioxol-5-yl)-4-hydroxy-3,6,7-trimethoxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1C2=C(C3=CC(=C(C=C3C(=C2C(=O)O1)C4=CC5=C(C=C4)OCO5)OC)OC)O
• SMILES (Isomeric): CO[C@@H]1C2=C(C3=CC(=C(C=C3C(=C2C(=O)O1)C4=CC5=C(C=C4)OCO5)OC)OC)O
• InChI: InChI=1S/C22H18O8/c1-25-14-7-11-12(8-15(14)26-2)20(23)19-18(21(24)30-22(19)27-3)17(11)10-4-5-13-16(6-10)29-9-28-13/h4-8,22-23H,9H2,1-3H3/t22-/m0/s1
• InChI Key: XURLTFUKDPZAPN-QFIPXVFZSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₂H₁₈O₈
• Molecular Weight: 410.40 g/mol
• Exact Mass: 410.10016753 g/mol
• Topological Polar Surface Area (TPSA): 92.70 Ų
• XlogP: 3.60
• Atomic LogP (AlogP): 3.77
• H-Bond Acceptor: 8
• H-Bond Donor: 1
• Rotatable Bonds: 4

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9884	98.84%
Caco-2	+	0.7399	73.99%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5429	54.29%
Subcellular localzation	Mitochondria	0.7882	78.82%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9046	90.46%
OATP1B3 inhibitior	+	0.8922	89.22%
MATE1 inhibitior	-	0.7800	78.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	+	0.8504	85.04%
P-glycoprotein inhibitior	+	0.6944	69.44%
P-glycoprotein substrate	-	0.8083	80.83%
CYP3A4 substrate	+	0.6059	60.59%
CYP2C9 substrate	-	0.8008	80.08%
CYP2D6 substrate	-	0.8397	83.97%
CYP3A4 inhibition	+	0.7920	79.20%
CYP2C9 inhibition	+	0.8924	89.24%
CYP2C19 inhibition	+	0.8377	83.77%
CYP2D6 inhibition	-	0.6838	68.38%
CYP1A2 inhibition	-	0.7973	79.73%
CYP2C8 inhibition	+	0.5701	57.01%
CYP inhibitory promiscuity	+	0.8157	81.57%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.4071	40.71%
Eye corrosion	-	0.9883	98.83%
Eye irritation	-	0.7297	72.97%
Skin irritation	-	0.7923	79.23%
Skin corrosion	-	0.9764	97.64%
Ames mutagenesis	-	0.5100	51.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4481	44.81%
Micronuclear	+	0.8374	83.74%
Hepatotoxicity	+	0.5500	55.00%
skin sensitisation	-	0.8026	80.26%
Respiratory toxicity	+	0.6444	64.44%
Reproductive toxicity	+	0.6889	68.89%
Mitochondrial toxicity	+	0.5500	55.00%
Nephrotoxicity	-	0.6332	63.32%
Acute Oral Toxicity (c)	III	0.5047	50.47%
Estrogen receptor binding	+	0.9436	94.36%
Androgen receptor binding	+	0.6802	68.02%
Thyroid receptor binding	+	0.7879	78.79%
Glucocorticoid receptor binding	+	0.9272	92.72%
Aromatase binding	+	0.6149	61.49%
PPAR gamma	+	0.8190	81.90%
Honey bee toxicity	-	0.7931	79.31%
Biodegradation	-	0.9250	92.50%
Crustacea aquatic toxicity	+	0.5351	53.51%
Fish aquatic toxicity	+	0.9623	96.23%

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	98.89%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	95.52%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	95.18%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	94.65%	89.00%
CHEMBL1951	P21397	Monoamine oxidase A	94.44%	91.49%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	94.32%	92.62%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.31%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.82%	85.14%
CHEMBL2581	P07339	Cathepsin D	92.70%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	89.74%	96.09%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	89.54%	94.80%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.18%	94.00%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	87.91%	96.77%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.17%	99.23%
CHEMBL1937	Q92769	Histone deacetylase 2	85.62%	94.75%
CHEMBL3438	Q05513	Protein kinase C zeta	85.50%	88.48%
CHEMBL5311	P37023	Serine/threonine-protein kinase receptor R3	85.49%	82.67%
CHEMBL241	Q14432	Phosphodiesterase 3A	84.06%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.40%	97.09%
CHEMBL2094127	P06493	Cyclin-dependent kinase 1/cyclin B	83.39%	96.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.89%	95.89%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.05%	96.00%
CHEMBL3192	Q9BY41	Histone deacetylase 8	81.00%	93.99%
CHEMBL5925	P22413	Ectonucleotide pyrophosphatase/phosphodiesterase family member 1	80.96%	92.38%
CHEMBL4225	P49760	Dual specificity protein kinase CLK2	80.44%	80.96%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.36%	97.14%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.17%	99.15%
CHEMBL5339	Q5NUL3	G-protein coupled receptor 120	80.08%	95.78%

Plants that contains it

• Cleistanthus collinus

Cross-Links

• PubChem: 154496353
• LOTUS: LTS0095436
• wikiData: Q105342541