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

Details

• Internal ID: 6f27883e-1a63-460d-82f3-4829220b2aea
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 4-(1,3-benzodioxol-5-yl)-9-[(2S,3R,4R)-3-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-7-hydroxy-6-methoxy-1H-benzo[f][2]benzofuran-3-one
• SMILES (Canonical): COC1=C(C=C2C(=C1)C(=C3C(=C2OC4C(C(CO4)(CO)O)OC5C(C(CO5)(CO)O)O)COC3=O)C6=CC7=C(C=C6)OCO7)O
• 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@](CO5)(CO)O)O)COC3=O)C6=CC7=C(C=C6)OCO7)O
• InChI: InChI=1S/C30H30O15/c1-38-19-6-14-15(5-17(19)33)23(16-7-39-26(35)22(16)21(14)13-2-3-18-20(4-13)43-12-42-18)44-28-25(30(37,9-32)11-41-28)45-27-24(34)29(36,8-31)10-40-27/h2-6,24-25,27-28,31-34,36-37H,7-12H2,1H3/t24-,25-,27-,28-,29+,30+/m0/s1
• InChI Key: HYFKLBPOZMDIJB-VBZFCZMHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₀H₃₀O₁₅
• Molecular Weight: 630.50 g/mol
• Exact Mass: 630.15847025 g/mol
• Topological Polar Surface Area (TPSA): 212.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -0.10
• H-Bond Acceptor: 15
• H-Bond Donor: 6
• Rotatable Bonds: 8

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8276	82.76%
Caco-2	-	0.8625	86.25%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.7143	71.43%
Subcellular localzation	Mitochondria	0.5858	58.58%
OATP2B1 inhibitior	-	0.8594	85.94%
OATP1B1 inhibitior	+	0.8914	89.14%
OATP1B3 inhibitior	+	0.9616	96.16%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.9000	90.00%
BSEP inhibitior	+	0.9535	95.35%
P-glycoprotein inhibitior	+	0.6380	63.80%
P-glycoprotein substrate	+	0.5091	50.91%
CYP3A4 substrate	+	0.6890	68.90%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8575	85.75%
CYP3A4 inhibition	-	0.5116	51.16%
CYP2C9 inhibition	-	0.8135	81.35%
CYP2C19 inhibition	-	0.7728	77.28%
CYP2D6 inhibition	-	0.8829	88.29%
CYP1A2 inhibition	-	0.8913	89.13%
CYP2C8 inhibition	+	0.7390	73.90%
CYP inhibitory promiscuity	-	0.6479	64.79%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.4924	49.24%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9254	92.54%
Skin irritation	-	0.7933	79.33%
Skin corrosion	-	0.9387	93.87%
Ames mutagenesis	+	0.6300	63.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7142	71.42%
Micronuclear	+	0.7133	71.33%
Hepatotoxicity	+	0.6302	63.02%
skin sensitisation	-	0.8541	85.41%
Respiratory toxicity	+	0.7444	74.44%
Reproductive toxicity	+	0.8667	86.67%
Mitochondrial toxicity	+	0.7250	72.50%
Nephrotoxicity	+	0.5361	53.61%
Acute Oral Toxicity (c)	III	0.6916	69.16%
Estrogen receptor binding	+	0.8377	83.77%
Androgen receptor binding	+	0.7135	71.35%
Thyroid receptor binding	+	0.5453	54.53%
Glucocorticoid receptor binding	+	0.7423	74.23%
Aromatase binding	+	0.6903	69.03%
PPAR gamma	+	0.7070	70.70%
Honey bee toxicity	-	0.7215	72.15%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.7756	77.56%

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	99.71%	91.11%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	99.20%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	98.08%	95.56%
CHEMBL4303	P08238	Heat shock protein HSP 90-beta	96.42%	96.77%
CHEMBL2581	P07339	Cathepsin D	96.32%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	96.16%	86.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	95.58%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	95.31%	92.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	94.40%	94.00%
CHEMBL4481	P35228	Nitric oxide synthase, inducible	93.89%	94.80%
CHEMBL3137262	O60341	LSD1/CoREST complex	91.88%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	91.63%	96.09%
CHEMBL2535	P11166	Glucose transporter	89.74%	98.75%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.67%	85.14%
CHEMBL4940	P07195	L-lactate dehydrogenase B chain	89.04%	95.53%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.61%	100.00%
CHEMBL3038477	P67870	Casein kinase II alpha/beta	87.78%	99.23%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.71%	99.15%
CHEMBL240	Q12809	HERG	86.40%	89.76%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	85.51%	97.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.42%	96.00%
CHEMBL1951	P21397	Monoamine oxidase A	85.37%	91.49%
CHEMBL4302	P08183	P-glycoprotein 1	85.18%	92.98%
CHEMBL1907	P15144	Aminopeptidase N	84.89%	93.31%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.48%	97.28%
CHEMBL5608	Q16288	NT-3 growth factor receptor	84.36%	95.89%
CHEMBL335	P18031	Protein-tyrosine phosphatase 1B	83.19%	95.17%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	82.77%	92.88%
CHEMBL5555	O00767	Acyl-CoA desaturase	82.59%	97.50%
CHEMBL226	P30542	Adenosine A1 receptor	81.97%	95.93%
CHEMBL5697	Q9GZT9	Egl nine homolog 1	80.30%	93.40%
CHEMBL4208	P20618	Proteasome component C5	80.24%	90.00%

Plants that contains it

• Justicia patentiflora

Cross-Links

• PubChem: 102177017
• LOTUS: LTS0155540
• wikiData: Q105035287