(1R)-1alpha-(3-Hydroxy-4-methoxyphenyl)-4alpha-[3-methoxy-4-(beta-D-glucopyranosyloxy)phenyl]-3aalpha,4,6,6aalpha-tetrahydro-1H,3H-furo[3,4-c]furan

Details

• Internal ID: baf1cf35-d502-4a53-92a3-adaa824b3b08
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(3R,3aS,6R,6aS)-3-(3-hydroxy-4-methoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)O
• SMILES (Isomeric): COC1=C(C=C(C=C1)[C@H]2[C@@H]3CO[C@H]([C@@H]3CO2)C4=CC(=C(C=C4)O[C@H]5[C@@H]([C@H]([C@@H]([C@H](O5)CO)O)O)O)OC)O
• InChI: InChI=1S/C26H32O11/c1-32-17-5-3-12(7-16(17)28)24-14-10-35-25(15(14)11-34-24)13-4-6-18(19(8-13)33-2)36-26-23(31)22(30)21(29)20(9-27)37-26/h3-8,14-15,20-31H,9-11H2,1-2H3/t14-,15-,20-,21-,22+,23-,24+,25+,26-/m1/s1
• InChI Key: BZPIKZWNIVAFRW-JKUDBEEXSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₂₆H₃₂O₁₁
• Molecular Weight: 520.50 g/mol
• Exact Mass: 520.19446183 g/mol
• Topological Polar Surface Area (TPSA): 157.00 Ų
• XlogP: 0.50
• Atomic LogP (AlogP): 0.66
• H-Bond Acceptor: 11
• H-Bond Donor: 5
• Rotatable Bonds: 7

Synonyms

• (1R)-1alpha-(3-Hydroxy-4-methoxyphenyl)-4alpha-[3-methoxy-4-(beta-D-glucopyranosyloxy)phenyl]-3aalpha,4,6,6aalpha-tetrahydro-1H,3H-furo[3,4-c]furan

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5501	55.01%
Caco-2	-	0.8250	82.50%
Blood Brain Barrier	-	0.5500	55.00%
Human oral bioavailability	-	0.5857	58.57%
Subcellular localzation	Mitochondria	0.7266	72.66%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.8926	89.26%
OATP1B3 inhibitior	+	0.9691	96.91%
MATE1 inhibitior	-	0.9400	94.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.7545	75.45%
P-glycoprotein inhibitior	-	0.4875	48.75%
P-glycoprotein substrate	-	0.7870	78.70%
CYP3A4 substrate	+	0.5733	57.33%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7876	78.76%
CYP3A4 inhibition	-	0.8406	84.06%
CYP2C9 inhibition	-	0.8498	84.98%
CYP2C19 inhibition	-	0.7124	71.24%
CYP2D6 inhibition	-	0.8817	88.17%
CYP1A2 inhibition	-	0.8560	85.60%
CYP2C8 inhibition	+	0.5986	59.86%
CYP inhibitory promiscuity	-	0.5107	51.07%
UGT catelyzed	-	0.5000	50.00%
Carcinogenicity (binary)	-	0.9800	98.00%
Carcinogenicity (trinary)	Non-required	0.6086	60.86%
Eye corrosion	-	0.9909	99.09%
Eye irritation	-	0.9333	93.33%
Skin irritation	-	0.8431	84.31%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	-	0.5600	56.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.7914	79.14%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.8750	87.50%
skin sensitisation	-	0.8863	88.63%
Respiratory toxicity	+	0.5111	51.11%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.6625	66.25%
Nephrotoxicity	-	0.9292	92.92%
Acute Oral Toxicity (c)	III	0.6689	66.89%
Estrogen receptor binding	+	0.7313	73.13%
Androgen receptor binding	+	0.5891	58.91%
Thyroid receptor binding	+	0.6064	60.64%
Glucocorticoid receptor binding	+	0.6327	63.27%
Aromatase binding	-	0.5487	54.87%
PPAR gamma	+	0.6294	62.94%
Honey bee toxicity	-	0.8407	84.07%
Biodegradation	-	0.7750	77.50%
Crustacea aquatic toxicity	-	0.7400	74.00%
Fish aquatic toxicity	+	0.9086	90.86%

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	98.91%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.45%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.18%	97.09%
CHEMBL241	Q14432	Phosphodiesterase 3A	92.50%	92.94%
CHEMBL2581	P07339	Cathepsin D	91.69%	98.95%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	89.80%	94.00%
CHEMBL1951	P21397	Monoamine oxidase A	89.70%	91.49%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.92%	86.33%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	88.78%	85.14%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	88.01%	95.56%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.73%	99.17%
CHEMBL1806	P11388	DNA topoisomerase II alpha	86.29%	89.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.33%	89.62%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	85.04%	96.00%
CHEMBL4208	P20618	Proteasome component C5	83.54%	90.00%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.70%	86.92%
CHEMBL5608	Q16288	NT-3 growth factor receptor	81.37%	95.89%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	80.57%	92.62%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.32%	97.14%

Plants that contains it

• Symplocos setchuensis

Cross-Links

• PubChem: 44559931
• NPASS: NPC279298
• LOTUS: LTS0043353
• wikiData: Q104950612