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

Details

• Internal ID: e4b766d3-c1df-45ec-be5e-e28c2859494e
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 9-(1,3-benzodioxol-5-yl)-4-[(2S,3R,4S)-3-[(2S,3R,4S,5S)-4-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-3,5-dihydroxyoxan-2-yl]oxy-4-hydroxy-4-[[(2S,3R,4R,5R)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]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)(COC5C(C(C(CO5)O)O)O)O)OC6C(C(C(CO6)O)OC7C(C(CO7)(CO)O)O)O)COC3=O)C8=CC9=C(C=C8)OCO9)OC
• SMILES (Isomeric): COC1=C(C=C2C(=C1)C(=C3C(=C2O[C@H]4[C@@H]([C@@](CO4)(CO[C@H]5[C@@H]([C@@H]([C@@H](CO5)O)O)O)O)O[C@H]6[C@@H]([C@H]([C@H](CO6)O)O[C@H]7[C@@H]([C@](CO7)(CO)O)O)O)COC3=O)C8=CC9=C(C=C8)OCO9)OC
• InChI: InChI=1S/C41H48O23/c1-52-23-6-17-18(7-24(23)53-2)31(19-8-54-35(49)27(19)26(17)16-3-4-22-25(5-16)61-15-60-22)62-39-34(41(51,14-59-39)13-57-36-29(46)28(45)20(43)9-55-36)64-37-30(47)32(21(44)10-56-37)63-38-33(48)40(50,11-42)12-58-38/h3-7,20-21,28-30,32-34,36-39,42-48,50-51H,8-15H2,1-2H3/t20-,21+,28-,29-,30-,32+,33+,34+,36+,37+,38+,39+,40-,41+/m1/s1
• InChI Key: WXAISWUHCSJJHM-FIAALHANSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₄₁H₄₈O₂₃
• Molecular Weight: 908.80 g/mol
• Exact Mass: 908.25863777 g/mol
• Topological Polar Surface Area (TPSA): 319.00 Ų
• XlogP: -2.60
• Atomic LogP (AlogP): -2.87
• H-Bond Acceptor: 23
• H-Bond Donor: 9
• Rotatable Bonds: 13

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.7034	70.34%
Caco-2	-	0.8725	87.25%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7286	72.86%
Subcellular localzation	Mitochondria	0.6318	63.18%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8740	87.40%
OATP1B3 inhibitior	+	0.9571	95.71%
MATE1 inhibitior	-	0.8000	80.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9232	92.32%
P-glycoprotein inhibitior	+	0.7302	73.02%
P-glycoprotein substrate	+	0.6693	66.93%
CYP3A4 substrate	+	0.7188	71.88%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8579	85.79%
CYP3A4 inhibition	-	0.5777	57.77%
CYP2C9 inhibition	-	0.8919	89.19%
CYP2C19 inhibition	-	0.8219	82.19%
CYP2D6 inhibition	-	0.8842	88.42%
CYP1A2 inhibition	-	0.9079	90.79%
CYP2C8 inhibition	+	0.7798	77.98%
CYP inhibitory promiscuity	-	0.7397	73.97%
UGT catelyzed	+	0.9000	90.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.5926	59.26%
Eye corrosion	-	0.9904	99.04%
Eye irritation	-	0.9098	90.98%
Skin irritation	-	0.8085	80.85%
Skin corrosion	-	0.9448	94.48%
Ames mutagenesis	+	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7973	79.73%
Micronuclear	+	0.6074	60.74%
Hepatotoxicity	+	0.5927	59.27%
skin sensitisation	-	0.8667	86.67%
Respiratory toxicity	+	0.7111	71.11%
Reproductive toxicity	+	0.9333	93.33%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.6861	68.61%
Acute Oral Toxicity (c)	III	0.6425	64.25%
Estrogen receptor binding	+	0.8399	83.99%
Androgen receptor binding	+	0.6872	68.72%
Thyroid receptor binding	+	0.5342	53.42%
Glucocorticoid receptor binding	+	0.6669	66.69%
Aromatase binding	+	0.6217	62.17%
PPAR gamma	+	0.7583	75.83%
Honey bee toxicity	-	0.6653	66.53%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.5500	55.00%
Fish aquatic toxicity	+	0.7998	79.98%

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	99.45%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	98.68%	94.45%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	98.26%	96.77%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	97.56%	95.56%
CHEMBL2581	P07339	Cathepsin D	96.83%	98.95%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	96.24%	94.80%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	96.00%	92.62%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.83%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	95.69%	86.33%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	95.55%	95.17%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	93.94%	85.14%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	93.37%	94.00%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	93.10%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.69%	97.09%
CHEMBL2535	P11166	Glucose transporter	90.03%	98.75%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.99%	96.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	89.52%	97.14%
CHEMBL4302	P08183	P-glycoprotein 1	89.11%	92.98%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.22%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.14%	100.00%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	87.97%	95.53%
CHEMBL1907	P15144	Aminopeptidase N	84.24%	93.31%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	83.74%	99.23%
CHEMBL226	P30542	Adenosine A1 receptor	83.47%	95.93%
CHEMBL2111367	P27986	PI3-kinase p110-alpha/p85-alpha	83.38%	94.33%
CHEMBL3922	P50579	Methionine aminopeptidase 2	82.38%	97.28%
CHEMBL1937	Q92769	Histone deacetylase 2	82.31%	94.75%
CHEMBL5555	O00767	Acyl-CoA desaturase	81.19%	97.50%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	80.42%	92.88%
CHEMBL2803	P43403	Tyrosine-protein kinase ZAP-70	80.30%	82.50%

Plants that contains it

• Justicia procumbens

Cross-Links

• PubChem: 163024776
• LOTUS: LTS0047363
• wikiData: Q105314466