(2R,3R,4S,5S,6R)-2-[(E)-3-[4-[(1S,2R)-1,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]prop-2-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: dfe4d7c5-c621-4b58-add6-6007b8dc053c
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(E)-3-[4-[(1S,2R)-1,3-dihydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-2-yl]oxy-3,5-dimethoxyphenyl]prop-2-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=CC(=CC(=C1OC(CO)C(C2=CC(=C(C(=C2)OC)O)OC)O)OC)C=CCOC3C(C(C(C(O3)CO)O)O)O
• SMILES (Isomeric): COC1=CC(=CC(=C1O[C@H](CO)[C@H](C2=CC(=C(C(=C2)OC)O)OC)O)OC)/C=C/CO[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
• InChI: InChI=1S/C28H38O14/c1-36-16-10-15(11-17(37-2)23(16)32)22(31)20(12-29)41-27-18(38-3)8-14(9-19(27)39-4)6-5-7-40-28-26(35)25(34)24(33)21(13-30)42-28/h5-6,8-11,20-22,24-26,28-35H,7,12-13H2,1-4H3/b6-5+/t20-,21-,22+,24-,25+,26-,28-/m1/s1
• InChI Key: KZYXZRKDCSEJTK-JGCKPSQKSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₈H₃₈O₁₄
• Molecular Weight: 598.60 g/mol
• Exact Mass: 598.22615588 g/mol
• Topological Polar Surface Area (TPSA): 206.00 Ų
• XlogP: -0.20
• Atomic LogP (AlogP): -0.27
• H-Bond Acceptor: 14
• H-Bond Donor: 7
• Rotatable Bonds: 14

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.7580	75.80%
Caco-2	-	0.8559	85.59%
Blood Brain Barrier	-	0.5750	57.50%
Human oral bioavailability	-	0.5714	57.14%
Subcellular localzation	Mitochondria	0.5634	56.34%
OATP2B1 inhibitior	-	0.7183	71.83%
OATP1B1 inhibitior	+	0.7979	79.79%
OATP1B3 inhibitior	+	0.9684	96.84%
MATE1 inhibitior	-	0.9600	96.00%
OCT2 inhibitior	-	0.8750	87.50%
BSEP inhibitior	+	0.6663	66.63%
P-glycoprotein inhibitior	+	0.6437	64.37%
P-glycoprotein substrate	-	0.6815	68.15%
CYP3A4 substrate	+	0.5896	58.96%
CYP2C9 substrate	-	0.6100	61.00%
CYP2D6 substrate	-	0.8073	80.73%
CYP3A4 inhibition	-	0.8482	84.82%
CYP2C9 inhibition	-	0.8685	86.85%
CYP2C19 inhibition	-	0.8260	82.60%
CYP2D6 inhibition	-	0.8821	88.21%
CYP1A2 inhibition	-	0.8638	86.38%
CYP2C8 inhibition	+	0.5697	56.97%
CYP inhibitory promiscuity	-	0.6072	60.72%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9600	96.00%
Carcinogenicity (trinary)	Non-required	0.6753	67.53%
Eye corrosion	-	0.9911	99.11%
Eye irritation	-	0.9144	91.44%
Skin irritation	-	0.8673	86.73%
Skin corrosion	-	0.9589	95.89%
Ames mutagenesis	-	0.6100	61.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.4017	40.17%
Micronuclear	+	0.5059	50.59%
Hepatotoxicity	-	0.7697	76.97%
skin sensitisation	-	0.8621	86.21%
Respiratory toxicity	-	0.5444	54.44%
Reproductive toxicity	+	0.5889	58.89%
Mitochondrial toxicity	-	0.6500	65.00%
Nephrotoxicity	-	0.9023	90.23%
Acute Oral Toxicity (c)	III	0.7436	74.36%
Estrogen receptor binding	+	0.7610	76.10%
Androgen receptor binding	+	0.5300	53.00%
Thyroid receptor binding	+	0.6105	61.05%
Glucocorticoid receptor binding	+	0.6680	66.80%
Aromatase binding	+	0.5574	55.74%
PPAR gamma	+	0.6327	63.27%
Honey bee toxicity	-	0.7883	78.83%
Biodegradation	-	0.8250	82.50%
Crustacea aquatic toxicity	-	0.7100	71.00%
Fish aquatic toxicity	+	0.7816	78.16%

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	98.01%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	97.59%	96.09%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	96.89%	96.00%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	94.90%	85.14%
CHEMBL215	P09917	Arachidonate 5-lipoxygenase	93.92%	92.68%
CHEMBL1806	P11388	DNA topoisomerase II alpha	92.51%	89.00%
CHEMBL3401	O75469	Pregnane X receptor	91.75%	94.73%
CHEMBL3060	Q9Y345	Glycine transporter 2	91.47%	99.17%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	88.69%	89.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.54%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	87.67%	86.33%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.22%	86.92%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	86.29%	95.89%
CHEMBL2581	P07339	Cathepsin D	85.28%	98.95%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.19%	96.61%
CHEMBL2288	Q13526	Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1	81.83%	91.71%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	80.56%	99.15%

Plants that contains it

• Erythrina fusca
• Lonchocarpus minimiflorus
• Lupinus luteus
• Syringa pubescens subsp. patula

Cross-Links

• PubChem: 122203703
• LOTUS: LTS0237483
• wikiData: Q105306081