1-O-[[(1S,3S,4R)-3-hydroxy-4-(hydroxymethyl)-4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethenyl]cyclohexyl]methyl] 4-O-[[(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)-3-[(3,4-dimethoxyphenyl)methylidene]-2-[(4-methoxyphenyl)methylidene]butanedioate

Details

• Internal ID: cec0c071-866b-48c3-ad5d-75fa69af0164
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: 1-O-[[(1S,3S,4R)-3-hydroxy-4-(hydroxymethyl)-4-[2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyethenyl]cyclohexyl]methyl] 4-O-[[(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)-3-[(3,4-dimethoxyphenyl)methylidene]-2-[(4-methoxyphenyl)methylidene]butanedioate
• SMILES (Canonical): COC1=CC=C(C=C1)C=C(C(=CC2=CC(=C(C=C2)OC)OC)C(=O)OCC3CCC(C(C3)O)(CCOC4C(C(C(C(O4)CO)O)O)O)CO)C(=O)OCC5CCC(C(C5)O)(CO)C=COC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): COC1=CC=C(C=C1)/C=C(\C(=CC2=CC(=C(C=C2)OC)OC)C(=O)OC[C@H]3CC[C@@]([C@H](C3)O)(CCO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)CO)/C(=O)OC[C@H]5CC[C@]([C@H](C5)O)(CO)C=CO[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C53H74O23/c1-68-33-7-4-29(5-8-33)18-34(48(66)73-25-31-10-12-52(27-56,40(58)21-31)14-16-71-50-46(64)44(62)42(60)38(23-54)75-50)35(19-30-6-9-36(69-2)37(20-30)70-3)49(67)74-26-32-11-13-53(28-57,41(59)22-32)15-17-72-51-47(65)45(63)43(61)39(24-55)76-51/h4-9,14,16,18-20,31-32,38-47,50-51,54-65H,10-13,15,17,21-28H2,1-3H3/b16-14?,34-18+,35-19?/t31-,32-,38+,39+,40-,41-,42+,43+,44-,45-,46+,47+,50+,51+,52+,53+/m0/s1
• InChI Key: YMCGPPQUNZRKAH-LJNGAUCSSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₅₃H₇₄O₂₃
• Molecular Weight: 1079.10 g/mol
• Exact Mass: 1078.46208860 g/mol
• Topological Polar Surface Area (TPSA): 360.00 Ų
• XlogP: 1.30
• Atomic LogP (AlogP): -0.92
• H-Bond Acceptor: 23
• H-Bond Donor: 12
• Rotatable Bonds: 23

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.5735	57.35%
Caco-2	-	0.8586	85.86%
Blood Brain Barrier	-	0.6500	65.00%
Human oral bioavailability	-	0.7857	78.57%
Subcellular localzation	Mitochondria	0.7352	73.52%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8434	84.34%
OATP1B3 inhibitior	+	0.9174	91.74%
MATE1 inhibitior	-	0.8800	88.00%
OCT2 inhibitior	-	0.7250	72.50%
BSEP inhibitior	+	0.9873	98.73%
P-glycoprotein inhibitior	+	0.7469	74.69%
P-glycoprotein substrate	+	0.6277	62.77%
CYP3A4 substrate	+	0.7239	72.39%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.8478	84.78%
CYP3A4 inhibition	-	0.9044	90.44%
CYP2C9 inhibition	-	0.8466	84.66%
CYP2C19 inhibition	-	0.8041	80.41%
CYP2D6 inhibition	-	0.9134	91.34%
CYP1A2 inhibition	-	0.8262	82.62%
CYP2C8 inhibition	+	0.8232	82.32%
CYP inhibitory promiscuity	-	0.9524	95.24%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6846	68.46%
Eye corrosion	-	0.9893	98.93%
Eye irritation	-	0.9004	90.04%
Skin irritation	-	0.8031	80.31%
Skin corrosion	-	0.9523	95.23%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7961	79.61%
Micronuclear	-	0.7100	71.00%
Hepatotoxicity	-	0.7050	70.50%
skin sensitisation	-	0.8492	84.92%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.8222	82.22%
Mitochondrial toxicity	+	0.5750	57.50%
Nephrotoxicity	-	0.7182	71.82%
Acute Oral Toxicity (c)	III	0.5571	55.71%
Estrogen receptor binding	+	0.7772	77.72%
Androgen receptor binding	+	0.7373	73.73%
Thyroid receptor binding	+	0.6447	64.47%
Glucocorticoid receptor binding	+	0.7474	74.74%
Aromatase binding	+	0.6256	62.56%
PPAR gamma	+	0.8073	80.73%
Honey bee toxicity	-	0.7401	74.01%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.5800	58.00%
Fish aquatic toxicity	+	0.9354	93.54%

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	99.21%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.76%	91.11%
CHEMBL240	Q12809	HERG	97.35%	89.76%
CHEMBL3137262	O60341	LSD1/CoREST complex	97.11%	97.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	94.47%	96.00%
CHEMBL1293249	Q13887	Kruppel-like factor 5	94.39%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	91.94%	92.94%
CHEMBL2243	O00519	Anandamide amidohydrolase	91.68%	97.53%
CHEMBL5608	Q16288	NT-3 growth factor receptor	91.50%	95.89%
CHEMBL3060	Q9Y345	Glycine transporter 2	90.76%	99.17%
CHEMBL2007	P16234	Platelet-derived growth factor receptor alpha	89.83%	91.07%
CHEMBL3714130	P46095	G-protein coupled receptor 6	89.10%	97.36%
CHEMBL1806	P11388	DNA topoisomerase II alpha	88.72%	89.00%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.64%	95.56%
CHEMBL4208	P20618	Proteasome component C5	88.52%	90.00%
CHEMBL3880	P07900	Heat shock protein HSP 90-alpha	88.26%	96.21%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	88.15%	92.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	87.68%	97.25%
CHEMBL4793	Q86TI2	Dipeptidyl peptidase IX	86.84%	96.95%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	86.68%	91.03%
CHEMBL221	P23219	Cyclooxygenase-1	85.68%	90.17%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.60%	95.89%
CHEMBL2072	P35499	Sodium channel protein type IV alpha subunit	84.53%	92.32%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	83.94%	89.62%
CHEMBL3713062	P10646	Tissue factor pathway inhibitor	83.77%	97.33%
CHEMBL3807	P17706	T-cell protein-tyrosine phosphatase	81.92%	93.00%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	81.15%	95.50%
CHEMBL226	P30542	Adenosine A1 receptor	80.27%	95.93%
CHEMBL2535	P11166	Glucose transporter	80.17%	98.75%

Plants that contains it

• Cananga odorata

Cross-Links

• PubChem: 163189479
• LOTUS: LTS0166556
• wikiData: Q105350454