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

Details

• Internal ID: 24a15107-0c3d-4a65-b713-86ba1fa34f27
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 1-O-[[(1S,3S,4S)-4-formyl-3-hydroxy-4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethenyl]cyclohexyl]methyl] 4-O-[[(1S,3S,4S)-4-formyl-3-hydroxy-4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethyl]cyclohexyl]methyl] (3E)-3-[(3,4-dihydroxyphenyl)methylidene]-2-[(4-hydroxyphenyl)methylidene]butanedioate
• SMILES (Canonical): C1CC(C(CC1COC(=O)C(=CC2=CC(=C(C=C2)O)O)C(=CC3=CC=C(C=C3)O)C(=O)OCC4CCC(C(C4)O)(C=COC5C(C(C(C(O5)CO)O)O)O)C=O)O)(CCOC6C(C(C(C(O6)CO)O)O)O)C=O
• SMILES (Isomeric): C1C[C@@]([C@H](C[C@H]1COC(=O)/C(=C/C2=CC(=C(C=C2)O)O)/C(=CC3=CC=C(C=C3)O)C(=O)OC[C@H]4CC[C@@]([C@H](C4)O)(C=CO[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)C=O)O)(CCO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)C=O
• InChI: InChI=1S/C50H64O23/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/h1-6,11,13,15-17,24-25,28-29,35-44,47-48,51-52,55-65H,7-10,12,14,18-23H2/b13-11?,31-15?,32-16+/t28-,29-,35+,36+,37-,38-,39+,40+,41-,42-,43+,44+,47+,48+,49+,50+/m0/s1
• InChI Key: JLQIKEINPHHAHG-KTNMCLRUSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₅₀H₆₄O₂₃
• Molecular Weight: 1033.00 g/mol
• Exact Mass: 1032.38383828 g/mol
• Topological Polar Surface Area (TPSA): 387.00 Ų
• XlogP: 0.10
• Atomic LogP (AlogP): -1.41
• H-Bond Acceptor: 23
• H-Bond Donor: 13
• Rotatable Bonds: 20

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	-	0.8628	86.28%
Blood Brain Barrier	-	0.6250	62.50%
Human oral bioavailability	-	0.8143	81.43%
Subcellular localzation	Mitochondria	0.7536	75.36%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8500	85.00%
OATP1B3 inhibitior	+	0.9246	92.46%
MATE1 inhibitior	-	0.8200	82.00%
OCT2 inhibitior	-	0.7096	70.96%
BSEP inhibitior	+	0.9623	96.23%
P-glycoprotein inhibitior	+	0.7416	74.16%
P-glycoprotein substrate	+	0.5688	56.88%
CYP3A4 substrate	+	0.7091	70.91%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8539	85.39%
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	+	0.8410	84.10%
CYP inhibitory promiscuity	-	0.9471	94.71%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.6790	67.90%
Eye corrosion	-	0.9900	99.00%
Eye irritation	-	0.8995	89.95%
Skin irritation	-	0.8103	81.03%
Skin corrosion	-	0.9545	95.45%
Ames mutagenesis	-	0.5124	51.24%
Human Ether-a-go-go-Related Gene inhibition	+	0.7343	73.43%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.7425	74.25%
skin sensitisation	-	0.8204	82.04%
Respiratory toxicity	-	0.5111	51.11%
Reproductive toxicity	+	0.7778	77.78%
Mitochondrial toxicity	+	0.5125	51.25%
Nephrotoxicity	-	0.6594	65.94%
Acute Oral Toxicity (c)	III	0.5833	58.33%
Estrogen receptor binding	+	0.7285	72.85%
Androgen receptor binding	+	0.7540	75.40%
Thyroid receptor binding	+	0.6112	61.12%
Glucocorticoid receptor binding	+	0.7100	71.00%
Aromatase binding	+	0.5742	57.42%
PPAR gamma	+	0.7898	78.98%
Honey bee toxicity	-	0.6815	68.15%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.6200	62.00%
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	99.76%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.67%	96.09%
CHEMBL3137262	O60341	LSD1/CoREST complex	96.49%	97.09%
CHEMBL226	P30542	Adenosine A1 receptor	95.95%	95.93%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	95.44%	94.62%
CHEMBL216	P11229	Muscarinic acetylcholine receptor M1	94.20%	94.23%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	92.84%	97.33%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.01%	89.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	90.31%	86.33%
CHEMBL218	P21554	Cannabinoid CB1 receptor	89.47%	96.61%
CHEMBL3194	P02766	Transthyretin	88.31%	90.71%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.71%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.81%	89.62%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.75%	99.17%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	86.66%	90.71%
CHEMBL1951	P21397	Monoamine oxidase A	85.81%	91.49%
CHEMBL2781	P19634	Sodium/hydrogen exchanger 1	85.71%	90.24%
CHEMBL5608	Q16288	NT-3 growth factor receptor	85.36%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	84.60%	95.56%
CHEMBL3922	P50579	Methionine aminopeptidase 2	84.07%	97.28%
CHEMBL1994	P08235	Mineralocorticoid receptor	83.90%	100.00%
CHEMBL3891	P07384	Calpain 1	83.60%	93.04%
CHEMBL2243	O00519	Anandamide amidohydrolase	83.58%	97.53%
CHEMBL2563	Q9UQL6	Histone deacetylase 5	83.27%	89.67%
CHEMBL3401	O75469	Pregnane X receptor	82.63%	94.73%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	82.11%	95.89%
CHEMBL5852	Q96P65	Pyroglutamylated RFamide peptide receptor	82.11%	85.00%
CHEMBL245	P20309	Muscarinic acetylcholine receptor M3	81.53%	97.53%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	81.51%	96.00%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	81.40%	92.32%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	81.00%	91.03%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.39%	95.83%

Plants that contains it

• Cananga odorata

Cross-Links

• PubChem: 162819689
• LOTUS: LTS0071485
• wikiData: Q105131006