(2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-6-[3,5-dimethoxy-4-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol

Details

• Internal ID: 268813fc-a6de-49d9-954b-b7b4cb9f4836
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(3S,3aR,6S,6aR)-6-[3,5-dimethoxy-4-[(2R,3R,4S,5S,6S)-3,4,5-trihydroxy-6-methoxyoxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2,6-dimethoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1C(C(C(C(O1)OC2=C(C=C(C=C2OC)C3C4COC(C4CO3)C5=CC(=C(C(=C5)OC)OC6C(C(C(C(O6)CO)O)O)O)OC)OC)O)O)O
• SMILES (Isomeric): CO[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC2=C(C=C(C=C2OC)[C@@H]3[C@H]4CO[C@@H]([C@H]4CO3)C5=CC(=C(C(=C5)OC)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O)OC)OC)O)O)O
• InChI: InChI=1S/C34H46O18/c1-42-17-6-13(7-18(43-2)30(17)50-33-26(40)23(37)22(36)21(10-35)49-33)28-15-11-48-29(16(15)12-47-28)14-8-19(44-3)31(20(9-14)45-4)51-34-27(41)24(38)25(39)32(46-5)52-34/h6-9,15-16,21-29,32-41H,10-12H2,1-5H3/t15-,16-,21+,22+,23-,24-,25-,26+,27+,28+,29+,32-,33-,34+/m0/s1
• InChI Key: MCEPJYNQDQHWLS-PLANBKPHSA-N
• Popularity: 0 references in papers

Physical and Chemical Properties

• Molecular Formula: C₃₄H₄₆O₁₈
• Molecular Weight: 742.70 g/mol
• Exact Mass: 742.26841461 g/mol
• Topological Polar Surface Area (TPSA): 243.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.23
• H-Bond Acceptor: 18
• H-Bond Donor: 7
• Rotatable Bonds: 12

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5448	54.48%
Caco-2	-	0.8550	85.50%
Blood Brain Barrier	-	0.6000	60.00%
Human oral bioavailability	-	0.6000	60.00%
Subcellular localzation	Mitochondria	0.7094	70.94%
OATP2B1 inhibitior	-	0.8609	86.09%
OATP1B1 inhibitior	+	0.9042	90.42%
OATP1B3 inhibitior	+	0.9657	96.57%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7500	75.00%
BSEP inhibitior	+	0.7541	75.41%
P-glycoprotein inhibitior	+	0.6887	68.87%
P-glycoprotein substrate	-	0.8284	82.84%
CYP3A4 substrate	+	0.5794	57.94%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7831	78.31%
CYP3A4 inhibition	-	0.8850	88.50%
CYP2C9 inhibition	-	0.8524	85.24%
CYP2C19 inhibition	-	0.7622	76.22%
CYP2D6 inhibition	-	0.9085	90.85%
CYP1A2 inhibition	-	0.8720	87.20%
CYP2C8 inhibition	+	0.4846	48.46%
CYP inhibitory promiscuity	-	0.5471	54.71%
UGT catelyzed	-	0.6000	60.00%
Carcinogenicity (binary)	-	0.9700	97.00%
Carcinogenicity (trinary)	Non-required	0.5993	59.93%
Eye corrosion	-	0.9906	99.06%
Eye irritation	-	0.9053	90.53%
Skin irritation	-	0.8460	84.60%
Skin corrosion	-	0.9592	95.92%
Ames mutagenesis	-	0.6678	66.78%
Human Ether-a-go-go-Related Gene inhibition	+	0.8544	85.44%
Micronuclear	+	0.5700	57.00%
Hepatotoxicity	-	0.8500	85.00%
skin sensitisation	-	0.8954	89.54%
Respiratory toxicity	+	0.5333	53.33%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9341	93.41%
Acute Oral Toxicity (c)	III	0.6521	65.21%
Estrogen receptor binding	+	0.7890	78.90%
Androgen receptor binding	+	0.6430	64.30%
Thyroid receptor binding	+	0.5615	56.15%
Glucocorticoid receptor binding	+	0.6732	67.32%
Aromatase binding	+	0.5455	54.55%
PPAR gamma	+	0.6850	68.50%
Honey bee toxicity	-	0.8257	82.57%
Biodegradation	-	0.7250	72.50%
Crustacea aquatic toxicity	-	0.7600	76.00%
Fish aquatic toxicity	+	0.9093	90.93%

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	98.69%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.27%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	91.42%	85.14%
CHEMBL3137262	O60341	LSD1/CoREST complex	90.99%	97.09%
CHEMBL3060	Q9Y345	Glycine transporter 2	89.49%	99.17%
CHEMBL241	Q14432	Phosphodiesterase 3A	87.78%	92.94%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.97%	95.56%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.48%	89.62%
CHEMBL2581	P07339	Cathepsin D	86.40%	98.95%
CHEMBL1293249	Q13887	Kruppel-like factor 5	86.40%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	85.90%	94.00%
CHEMBL1907603	Q05586	Glutamate NMDA receptor; GRIN1/GRIN2B	84.22%	95.89%
CHEMBL218	P21554	Cannabinoid CB1 receptor	83.76%	96.61%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.55%	89.00%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	82.95%	92.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	82.68%	96.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.64%	86.92%

Plants that contains it

• Eucommia ulmoides

Cross-Links

• PubChem: 162848406
• LOTUS: LTS0204921
• wikiData: Q105161151