(2S,3R,4S,5S,6R)-2-[4-[6-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: a340fe90-4d42-4b0a-8ae6-a36a4b0ffa89
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[6-[3,5-dimethoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC(=C1OC2C(C(C(C(O2)CO)O)O)O)OC)C3C4COC(C4CO3)C5=CC(=C(C=C5)OC6C(C(C(C(O6)CO)O)O)O)OC
• SMILES (Isomeric): COC1=CC(=CC(=C1O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)CO)O)O)O)OC)C3C4COC(C4CO3)C5=CC(=C(C=C5)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)OC
• InChI: InChI=1S/C33H44O17/c1-42-18-6-13(4-5-17(18)47-32-27(40)25(38)23(36)21(9-34)48-32)29-15-11-46-30(16(15)12-45-29)14-7-19(43-2)31(20(8-14)44-3)50-33-28(41)26(39)24(37)22(10-35)49-33/h4-8,15-16,21-30,32-41H,9-12H2,1-3H3/t15?,16?,21-,22-,23-,24-,25+,26+,27-,28-,29?,30?,32-,33+/m1/s1
• InChI Key: WENLQSBQPMFCOA-YWNVIYJKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₃H₄₄O₁₇
• Molecular Weight: 712.70 g/mol
• Exact Mass: 712.25784993 g/mol
• Topological Polar Surface Area (TPSA): 245.00 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): -1.85
• H-Bond Acceptor: 17
• H-Bond Donor: 8
• Rotatable Bonds: 11

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5448	54.48%
Caco-2	-	0.8601	86.01%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.7094	70.94%
OATP2B1 inhibitior	-	0.8614	86.14%
OATP1B1 inhibitior	+	0.8931	89.31%
OATP1B3 inhibitior	+	0.9657	96.57%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.6758	67.58%
P-glycoprotein inhibitior	+	0.6548	65.48%
P-glycoprotein substrate	-	0.7925	79.25%
CYP3A4 substrate	+	0.5849	58.49%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7831	78.31%
CYP3A4 inhibition	-	0.8850	88.50%
CYP2C9 inhibition	-	0.8524	85.24%
CYP2C19 inhibition	-	0.7622	76.22%
CYP2D6 inhibition	-	0.9085	90.85%
CYP1A2 inhibition	-	0.8720	87.20%
CYP2C8 inhibition	+	0.6034	60.34%
CYP inhibitory promiscuity	-	0.5471	54.71%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5993	59.93%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9066	90.66%
Skin irritation	-	0.8460	84.60%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	-	0.6200	62.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8303	83.03%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8954	89.54%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9337	93.37%
Acute Oral Toxicity (c)	III	0.6521	65.21%
Estrogen receptor binding	+	0.7719	77.19%
Androgen receptor binding	+	0.5990	59.90%
Thyroid receptor binding	+	0.5434	54.34%
Glucocorticoid receptor binding	+	0.6076	60.76%
Aromatase binding	-	0.5162	51.62%
PPAR gamma	+	0.6792	67.92%
Honey bee toxicity	-	0.8332	83.32%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9093	90.93%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	98.88%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.18%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.14%	97.09%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	92.91%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.99%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.96%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.13%	89.62%
CHEMBL2581	P07339	Cathepsin D	87.89%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.85%	94.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.82%	96.00%
CHEMBL4145	Q9UKV0	Histone deacetylase 9	86.57%	85.49%
CHEMBL220	P22303	Acetylcholinesterase	86.10%	94.45%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.60%	95.56%
CHEMBL241	Q14432	Phosphodiesterase 3A	85.09%	92.94%
CHEMBL1806	P11388	DNA topoisomerase II alpha	84.74%	89.00%
CHEMBL4208	P20618	Proteasome component C5	83.44%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.45%	97.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	82.42%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.70%	92.62%
CHEMBL2535	P11166	Glucose transporter	80.35%	98.75%

Plants that contains it

• Eucommia ulmoides
• Tripterygium wilfordii

Cross-Links

• PubChem: 5319325
• NPASS: NPC46616