bis[[(1S,3S,4R)-3-hydroxy-4-(hydroxymethyl)-4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]cyclohexyl]methyl] (2E)-2-[(3,4-dihydroxyphenyl)methylidene]-3-[(4-hydroxyphenyl)methylidene]butanedioate

Details

• Internal ID: f5d4046e-759f-4ad6-9a18-6b675500359c
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: bis[[(1S,3S,4R)-3-hydroxy-4-(hydroxymethyl)-4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]cyclohexyl]methyl] (2E)-2-[(3,4-dihydroxyphenyl)methylidene]-3-[(4-hydroxyphenyl)methylidene]butanedioate
• SMILES (Canonical): C1CC(C(CC1COC(=O)C(=CC2=CC=C(C=C2)O)C(=CC3=CC(=C(C=C3)O)O)C(=O)OCC4CCC(C(C4)O)(CCOC5C(C(C(C(O5)CO)O)O)O)CO)O)(CCOC6C(C(C(C(O6)CO)O)O)O)CO
• SMILES (Isomeric): C1C[C@@]([C@H](C[C@H]1COC(=O)C(=CC2=CC=C(C=C2)O)/C(=C\C3=CC(=C(C=C3)O)O)/C(=O)OC[C@H]4CC[C@@]([C@H](C4)O)(CCO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)CO)O)(CCO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)CO
• InChI: InChI=1S/C50H70O23/c51-20-35-39(60)41(62)43(64)47(72-35)68-13-11-49(24-53)9-7-28(18-37(49)58)22-70-45(66)31(15-26-1-4-30(55)5-2-26)32(16-27-3-6-33(56)34(57)17-27)46(67)71-23-29-8-10-50(25-54,38(59)19-29)12-14-69-48-44(65)42(63)40(61)36(21-52)73-48/h1-6,15-17,28-29,35-44,47-48,51-65H,7-14,18-25H2/b31-15?,32-16+/t28-,29-,35+,36+,37-,38-,39+,40+,41-,42-,43+,44+,47+,48+,49+,50+/m0/s1
• InChI Key: FNWONUVTZXJTAU-PEAKBTTGSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₇₀O₂₃
• Molecular Weight: 1039.10 g/mol
• Exact Mass: 1038.43078848 g/mol
• Topological Polar Surface Area (TPSA): 393.00 Ų
• XlogP: 0.20
• Atomic LogP (AlogP): -1.95
• H-Bond Acceptor: 23
• H-Bond Donor: 15
• Rotatable Bonds: 21

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6415	64.15%
Caco-2	-	0.8670	86.70%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8857	88.57%
Subcellular localzation	Mitochondria	0.7536	75.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8557	85.57%
OATP1B3 inhibitior	+	0.9246	92.46%
MATE1 inhibitior	-	0.8400	84.00%
OCT2 inhibitior	-	0.7096	70.96%
BSEP inhibitior	+	0.9527	95.27%
P-glycoprotein inhibitior	+	0.7352	73.52%
P-glycoprotein substrate	-	0.6239	62.39%
CYP3A4 substrate	+	0.6836	68.36%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8547	85.47%
CYP3A4 inhibition	-	0.8990	89.90%
CYP2C9 inhibition	-	0.8053	80.53%
CYP2C19 inhibition	-	0.7384	73.84%
CYP2D6 inhibition	-	0.8897	88.97%
CYP1A2 inhibition	-	0.8336	83.36%
CYP2C8 inhibition	+	0.8081	80.81%
CYP inhibitory promiscuity	-	0.9471	94.71%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6790	67.90%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8993	89.93%
Skin irritation	-	0.8103	81.03%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	-	0.5754	57.54%
Human Ether-a-go-go-Related Gene inhibition	+	0.7510	75.10%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.8300	83.00%
skin sensitisation	-	0.8204	82.04%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.7462	74.62%
Acute Oral Toxicity (c)	III	0.5833	58.33%
Estrogen receptor binding	+	0.7473	74.73%
Androgen receptor binding	+	0.7297	72.97%
Thyroid receptor binding	+	0.5712	57.12%
Glucocorticoid receptor binding	+	0.6571	65.71%
Aromatase binding	+	0.6285	62.85%
PPAR gamma	+	0.7781	77.81%
Honey bee toxicity	-	0.7296	72.96%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.6400	64.00%
Fish aquatic toxicity	+	0.9538	95.38%

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	99.83%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.94%	97.09%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.64%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	94.36%	94.62%
CHEMBL226	P30542	Adenosine A1 receptor	92.52%	95.93%
CHEMBL1806	P11388	DNA topoisomerase II alpha	91.43%	89.00%
CHEMBL3194	P02766	Transthyretin	90.48%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	90.11%	91.49%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	89.71%	94.45%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.22%	86.33%
CHEMBL3060	Q9Y345	Glycine transporter 2	88.48%	99.17%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	87.35%	90.24%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	85.15%	94.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	84.96%	97.33%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	83.96%	95.56%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	83.73%	96.95%
CHEMBL5608	Q16288	NT-3 growth factor receptor	82.92%	95.89%
CHEMBL1994	P08235	Mineralocorticoid receptor	82.42%	100.00%
CHEMBL5255	O00206	Toll-like receptor 4	81.72%	92.50%
CHEMBL241	Q14432	Phosphodiesterase 3A	81.50%	92.94%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	80.80%	96.21%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	80.67%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	80.34%	89.62%

Plants that contains it

• Cananga odorata

Cross-Links

• PubChem: 162819687
• LOTUS: LTS0222079
• wikiData: Q104998581