(2R,3S,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[4-[(2R,3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-3,4-bis(hydroxymethyl)oxolan-2-yl]-2-methoxyphenoxy]-2-(hydroxymethyl)oxane-3,4-diol

Details

• Internal ID: 71d6d797-9a61-428b-ba07-b77feeaf9c6f
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2R,3S,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-6-[4-[(2R,3S,4S,5R)-5-(4-hydroxy-3-methoxyphenyl)-3,4-bis(hydroxymethyl)oxolan-2-yl]-2-methoxyphenoxy]-2-(hydroxymethyl)oxane-3,4-diol
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C(C(C(O2)C3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)OC5C(C(CO5)(CO)O)O)OC)CO)CO)O
• SMILES (Isomeric): COC1=C(C=CC(=C1)[C@H]2[C@@H]([C@H]([C@@H](O2)C3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O[C@H]5[C@@H]([C@](CO5)(CO)O)O)OC)CO)CO)O
• InChI: InChI=1S/C31H42O16/c1-41-20-7-14(3-5-18(20)36)25-16(9-32)17(10-33)26(46-25)15-4-6-19(21(8-15)42-2)44-29-27(24(38)23(37)22(11-34)45-29)47-30-28(39)31(40,12-35)13-43-30/h3-8,16-17,22-30,32-40H,9-13H2,1-2H3/t16-,17-,22-,23-,24+,25+,26+,27-,28+,29-,30+,31-/m1/s1
• InChI Key: GKSZOVHKODBYMX-ZGSXILORSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₁H₄₂O₁₆
• Molecular Weight: 670.70 g/mol
• Exact Mass: 670.24728525 g/mol
• Topological Polar Surface Area (TPSA): 247.00 Ų
• XlogP: -1.70
• Atomic LogP (AlogP): -1.92
• H-Bond Acceptor: 16
• H-Bond Donor: 9
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	-	0.6533	65.33%
Caco-2	-	0.8903	89.03%
Blood Brain Barrier	+	0.5250	52.50%
Human oral bioavailability	-	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7241	72.41%
OATP2B1 inhibitior	-	0.8654	86.54%
OATP1B1 inhibitior	+	0.8747	87.47%
OATP1B3 inhibitior	+	0.9588	95.88%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.8500	85.00%
BSEP inhibitior	+	0.7625	76.25%
P-glycoprotein inhibitior	+	0.5948	59.48%
P-glycoprotein substrate	-	0.6663	66.63%
CYP3A4 substrate	+	0.6547	65.47%
CYP2C9 substrate	-	0.8015	80.15%
CYP2D6 substrate	-	0.8184	81.84%
CYP3A4 inhibition	-	0.8346	83.46%
CYP2C9 inhibition	-	0.8729	87.29%
CYP2C19 inhibition	-	0.8375	83.75%
CYP2D6 inhibition	-	0.9071	90.71%
CYP1A2 inhibition	-	0.8763	87.63%
CYP2C8 inhibition	+	0.6158	61.58%
CYP inhibitory promiscuity	-	0.6945	69.45%
UGT catelyzed	+	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5546	55.46%
Eye corrosion	-	0.9913	99.13%
Eye irritation	-	0.9280	92.80%
Skin irritation	-	0.8332	83.32%
Skin corrosion	-	0.9459	94.59%
Ames mutagenesis	-	0.5700	57.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7612	76.12%
Micronuclear	+	0.5559	55.59%
Hepatotoxicity	-	0.6750	67.50%
skin sensitisation	-	0.8671	86.71%
Respiratory toxicity	+	0.5444	54.44%
Reproductive toxicity	+	0.7000	70.00%
Mitochondrial toxicity	-	0.5000	50.00%
Nephrotoxicity	-	0.8629	86.29%
Acute Oral Toxicity (c)	III	0.7005	70.05%
Estrogen receptor binding	+	0.7671	76.71%
Androgen receptor binding	+	0.6642	66.42%
Thyroid receptor binding	+	0.5637	56.37%
Glucocorticoid receptor binding	+	0.5903	59.03%
Aromatase binding	+	0.5654	56.54%
PPAR gamma	+	0.6801	68.01%
Honey bee toxicity	-	0.7740	77.40%
Biodegradation	-	0.8500	85.00%
Crustacea aquatic toxicity	-	0.6600	66.00%
Fish aquatic toxicity	+	0.7597	75.97%

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	99.60%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	96.30%	96.09%
CHEMBL1951	P21397	Monoamine oxidase A	95.78%	91.49%
CHEMBL241	Q14432	Phosphodiesterase 3A	94.56%	92.94%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.70%	97.09%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	92.66%	95.56%
CHEMBL1806	P11388	DNA topoisomerase II alpha	90.73%	89.00%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	89.70%	96.00%
CHEMBL4208	P20618	Proteasome component C5	88.86%	90.00%
CHEMBL226	P30542	Adenosine A1 receptor	88.81%	95.93%
CHEMBL5608	Q16288	NT-3 growth factor receptor	88.80%	95.89%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.63%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	88.39%	94.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	87.95%	86.92%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	86.29%	94.45%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	84.23%	97.14%
CHEMBL3714130	P46095	G-protein coupled receptor 6	81.36%	97.36%
CHEMBL2581	P07339	Cathepsin D	81.34%	98.95%
CHEMBL1907605	P24864	Cyclin-dependent kinase 2/cyclin E1	81.33%	92.88%
CHEMBL3060	Q9Y345	Glycine transporter 2	81.24%	99.17%
CHEMBL3476	O15111	Inhibitor of nuclear factor kappa B kinase alpha subunit	80.50%	95.83%

Plants that contains it

• Astragalus pycnocephalus

Cross-Links

• PubChem: 11767553
• LOTUS: LTS0026013
• wikiData: Q105010263