(2S,3R,4S,5R,6R)-6-[(2R)-3-[(E)-3-[4-[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]prop-2-enoyl]oxy-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid

Details

• Internal ID: f7db4c83-a507-4ae9-b962-f457da3ae9c4
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5R,6R)-6-[(2R)-3-[(E)-3-[4-[(1R,2S)-1,3-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-2-yl]oxy-3-methoxyphenyl]prop-2-enoyl]oxy-2-hydroxypropoxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
• SMILES (Canonical): COC1=C(C=CC(=C1)C=CC(=O)OCC(COC2C(C(C(C(O2)C(=O)O)O)O)O)O)OC(CO)C(C3=CC(=C(C=C3)O)OC)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)/C=C/C(=O)OC[C@@H](CO[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)C(=O)O)O)O)O)O)O[C@@H](CO)[C@@H](C3=CC(=C(C=C3)O)OC)O
• InChI: InChI=1S/C29H36O16/c1-40-19-10-15(5-6-17(19)32)23(34)21(11-30)44-18-7-3-14(9-20(18)41-2)4-8-22(33)42-12-16(31)13-43-29-26(37)24(35)25(36)27(45-29)28(38)39/h3-10,16,21,23-27,29-32,34-37H,11-13H2,1-2H3,(H,38,39)/b8-4+/t16-,21-,23+,24-,25+,26+,27-,29+/m0/s1
• InChI Key: KAPAGFZZBVGHML-LBUUIVEHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₂₉H₃₆O₁₆
• Molecular Weight: 640.60 g/mol
• Exact Mass: 640.20033506 g/mol
• Topological Polar Surface Area (TPSA): 251.00 Ų
• XlogP: -0.70
• Atomic LogP (AlogP): -1.29
• H-Bond Acceptor: 15
• H-Bond Donor: 8
• Rotatable Bonds: 15

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6959	69.59%
Caco-2	-	0.8691	86.91%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.6286	62.86%
Subcellular localzation	Mitochondria	0.5043	50.43%
OATP2B1 inhibitior	-	0.5746	57.46%
OATP1B1 inhibitior	+	0.8826	88.26%
OATP1B3 inhibitior	+	0.9631	96.31%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.9391	93.91%
P-glycoprotein inhibitior	+	0.6962	69.62%
P-glycoprotein substrate	+	0.5000	50.00%
CYP3A4 substrate	+	0.6254	62.54%
CYP2C9 substrate	-	0.8035	80.35%
CYP2D6 substrate	-	0.8642	86.42%
CYP3A4 inhibition	-	0.7980	79.80%
CYP2C9 inhibition	-	0.9001	90.01%
CYP2C19 inhibition	-	0.9169	91.69%
CYP2D6 inhibition	-	0.9036	90.36%
CYP1A2 inhibition	-	0.8838	88.38%
CYP2C8 inhibition	+	0.7371	73.71%
CYP inhibitory promiscuity	-	0.8861	88.61%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.9500	95.00%
Carcinogenicity (trinary)	Non-required	0.7593	75.93%
Eye corrosion	-	0.9917	99.17%
Eye irritation	-	0.9180	91.80%
Skin irritation	-	0.8574	85.74%
Skin corrosion	-	0.9521	95.21%
Ames mutagenesis	-	0.7700	77.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7582	75.82%
Micronuclear	+	0.5433	54.33%
Hepatotoxicity	-	0.6196	61.96%
skin sensitisation	-	0.8574	85.74%
Respiratory toxicity	+	0.6000	60.00%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	+	0.5375	53.75%
Nephrotoxicity	-	0.9511	95.11%
Acute Oral Toxicity (c)	III	0.7564	75.64%
Estrogen receptor binding	+	0.7416	74.16%
Androgen receptor binding	+	0.6090	60.90%
Thyroid receptor binding	+	0.5623	56.23%
Glucocorticoid receptor binding	+	0.6941	69.41%
Aromatase binding	-	0.4949	49.49%
PPAR gamma	+	0.6207	62.07%
Honey bee toxicity	-	0.8105	81.05%
Biodegradation	-	0.8750	87.50%
Crustacea aquatic toxicity	-	0.6300	63.00%
Fish aquatic toxicity	+	0.8338	83.38%

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	98.96%	96.09%
CHEMBL1293249	Q13887	Kruppel-like factor 5	98.02%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	97.53%	85.14%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	97.52%	96.00%
CHEMBL1806	P11388	DNA topoisomerase II alpha	93.79%	89.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	93.77%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	93.66%	95.56%
CHEMBL3194	P02766	Transthyretin	91.82%	90.71%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	91.69%	89.62%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.40%	91.11%
CHEMBL2581	P07339	Cathepsin D	90.47%	98.95%
CHEMBL2413	P32246	C-C chemokine receptor type 1	88.99%	89.50%
CHEMBL4040	P28482	MAP kinase ERK2	86.62%	83.82%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	84.49%	99.15%
CHEMBL1951	P21397	Monoamine oxidase A	83.30%	91.49%
CHEMBL4208	P20618	Proteasome component C5	82.22%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	81.59%	94.45%
CHEMBL5845	P23415	Glycine receptor subunit alpha-1	81.37%	90.71%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.57%	95.89%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	80.03%	95.89%

Plants that contains it

• Medicago truncatula

Cross-Links

• PubChem: 163188221
• LOTUS: LTS0219128
• wikiData: Q105137938