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

Details

• Internal ID: 3feb071d-4cf7-4af9-bb25-ee449ff44295
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-4-[(2R,3R,4R)-3-[(2S,3R,4R,5S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,4-dihydroxyoxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6,7-dimethoxy-3H-benzo[f][2]benzofuran-1-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=C3C(=C2OC4C(C(CO4)(CO)O)OC5C(C(C(CO5)OC6C(C(CO6)(CO)O)O)O)O)COC3=O)C7=CC8=C(C=C7)OCO8)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=C3C(=C2O[C@@H]4[C@@H]([C@](CO4)(CO)O)O[C@H]5[C@@H]([C@H]([C@H](CO5)O[C@H]6[C@@H]([C@](CO6)(CO)O)O)O)O)COC3=O)C7=CC8=C(C=C7)OCO8)OC
• InChI: InChI=1S/C36H40O19/c1-45-20-6-16-17(7-21(20)46-2)28(18-8-47-31(42)25(18)24(16)15-3-4-19-22(5-15)52-14-51-19)54-34-30(36(44,11-38)13-50-34)55-32-27(40)26(39)23(9-48-32)53-33-29(41)35(43,10-37)12-49-33/h3-7,23,26-27,29-30,32-34,37-41,43-44H,8-14H2,1-2H3/t23-,26-,27+,29-,30-,32-,33-,34+,35+,36+/m0/s1
• InChI Key: FSCCKDWQFMYRMK-HKZAYDJQSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₆H₄₀O₁₉
• Molecular Weight: 776.70 g/mol
• Exact Mass: 776.21637904 g/mol
• Topological Polar Surface Area (TPSA): 260.00 Ų
• XlogP: -1.10
• Atomic LogP (AlogP): -1.33
• H-Bond Acceptor: 19
• H-Bond Donor: 7
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.6797	67.97%
Caco-2	-	0.8697	86.97%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.7000	70.00%
Subcellular localzation	Mitochondria	0.5810	58.10%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8845	88.45%
OATP1B3 inhibitior	+	0.9593	95.93%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9536	95.36%
P-glycoprotein inhibitior	+	0.7187	71.87%
P-glycoprotein substrate	+	0.5977	59.77%
CYP3A4 substrate	+	0.7092	70.92%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8579	85.79%
CYP3A4 inhibition	-	0.5271	52.71%
CYP2C9 inhibition	-	0.8892	88.92%
CYP2C19 inhibition	-	0.8349	83.49%
CYP2D6 inhibition	-	0.8837	88.37%
CYP1A2 inhibition	-	0.9059	90.59%
CYP2C8 inhibition	+	0.7580	75.80%
CYP inhibitory promiscuity	-	0.6678	66.78%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9900	99.00%
Carcinogenicity (trinary)	Non-required	0.5603	56.03%
Eye corrosion	-	0.9903	99.03%
Eye irritation	-	0.9176	91.76%
Skin irritation	-	0.8046	80.46%
Skin corrosion	-	0.9397	93.97%
Ames mutagenesis	+	0.6000	60.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7276	72.76%
Micronuclear	+	0.7033	70.33%
Hepatotoxicity	+	0.6302	63.02%
skin sensitisation	-	0.8697	86.97%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.7000	70.00%
Nephrotoxicity	+	0.5104	51.04%
Acute Oral Toxicity (c)	III	0.7163	71.63%
Estrogen receptor binding	+	0.8257	82.57%
Androgen receptor binding	+	0.6854	68.54%
Thyroid receptor binding	+	0.5349	53.49%
Glucocorticoid receptor binding	+	0.6979	69.79%
Aromatase binding	+	0.6111	61.11%
PPAR gamma	+	0.7338	73.38%
Honey bee toxicity	-	0.6613	66.13%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	+	0.6967	69.67%

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	99.50%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.80%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	97.95%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.35%	95.56%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	97.22%	94.80%
CHEMBL2581	P07339	Cathepsin D	96.81%	98.95%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.77%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.66%	86.33%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	95.18%	92.62%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	94.27%	95.17%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.17%	94.00%
CHEMBL2535	P11166	Glucose transporter	93.90%	98.75%
CHEMBL4302	P08183	P-glycoprotein 1	93.12%	92.98%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.39%	97.09%
CHEMBL1994	P08235	Mineralocorticoid receptor	89.91%	100.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.22%	96.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	87.97%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	87.83%	95.89%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.65%	99.23%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	86.63%	95.53%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	86.50%	97.14%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.60%	97.28%
CHEMBL2378	P30307	Dual specificity phosphatase Cdc25C	84.07%	96.67%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	84.06%	82.50%
CHEMBL221	P23219	Cyclooxygenase-1	83.92%	90.17%
CHEMBL240	Q12809	HERG	83.22%	89.76%
CHEMBL1951	P21397	Monoamine oxidase A	82.67%	91.49%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	81.19%	94.33%
CHEMBL4208	P20618	Proteasome component C5	81.07%	90.00%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.05%	97.50%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	80.86%	85.14%

Plants that contains it

• Haplophyllum patavinum

Cross-Links

• PubChem: 162965945
• LOTUS: LTS0021526
• wikiData: Q105000567