[(1R)-3aalpha,4,6,6aalpha-Tetrahydro-1H,3H-furo[3,4-c]furan-1alpha,4alpha-diyl]bis(2-methoxy-4,1-phenylene)bis(beta-D-glucopyranoside)

Details

• Internal ID: 1462fde1-8b6f-4e33-b7a8-8ba4174b1f6b
• Taxonomy: Lignans, neolignans and related compounds > Lignan glycosides
• IUPAC Name: (2S,3R,4S,5S,6R)-2-[4-[(3R,3aS,6R,6aS)-6-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-3-yl]-2-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• SMILES (Canonical): COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)OC6C(C(C(C(O6)CO)O)O)O
• SMILES (Isomeric): COC1=C(C=CC(=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[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O
• InChI: InChI=1S/C32H42O16/c1-41-19-7-13(3-5-17(19)45-31-27(39)25(37)23(35)21(9-33)47-31)29-15-11-44-30(16(15)12-43-29)14-4-6-18(20(8-14)42-2)46-32-28(40)26(38)24(36)22(10-34)48-32/h3-8,15-16,21-40H,9-12H2,1-2H3/t15-,16-,21-,22-,23-,24-,25+,26+,27-,28-,29+,30+,31-,32-/m1/s1
• InChI Key: ZJSJQWDXAYNLNS-PETZUENDSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₃₂H₄₂O₁₆
• Molecular Weight: 682.70 g/mol
• Exact Mass: 682.24728525 g/mol
• Topological Polar Surface Area (TPSA): 236.00 Ų
• XlogP: -1.30
• Atomic LogP (AlogP): -1.86
• H-Bond Acceptor: 16
• H-Bond Donor: 8
• Rotatable Bonds: 10

Synonyms

• [(1R)-3aalpha,4,6,6aalpha-Tetrahydro-1H,3H-furo[3,4-c]furan-1alpha,4alpha-diyl]bis(2-methoxy-4,1-phenylene)bis(beta-D-glucopyranoside)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.5501	55.01%
Caco-2	-	0.8602	86.02%
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	+	0.8948	89.48%
OATP1B3 inhibitior	+	0.9691	96.91%
MATE1 inhibitior	-	0.9200	92.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	+	0.6772	67.72%
P-glycoprotein inhibitior	+	0.6562	65.62%
P-glycoprotein substrate	-	0.8401	84.01%
CYP3A4 substrate	+	0.5453	54.53%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	-	0.7831	78.31%
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	+	0.4724	47.24%
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	-	0.9078	90.78%
Skin irritation	-	0.8431	84.31%
Skin corrosion	-	0.9576	95.76%
Ames mutagenesis	-	0.5500	55.00%
Human Ether-a-go-go-Related Gene inhibition	+	0.8379	83.79%
Micronuclear	+	0.5900	59.00%
Hepatotoxicity	-	0.8875	88.75%
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	-	0.9182	91.82%
Acute Oral Toxicity (c)	III	0.6689	66.89%
Estrogen receptor binding	+	0.7755	77.55%
Androgen receptor binding	+	0.6225	62.25%
Thyroid receptor binding	+	0.5376	53.76%
Glucocorticoid receptor binding	+	0.5758	57.58%
Aromatase binding	-	0.5137	51.37%
PPAR gamma	+	0.6783	67.83%
Honey bee toxicity	-	0.8590	85.90%
Biodegradation	-	0.8000	80.00%
Crustacea aquatic toxicity	-	0.7600	76.00%
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	98.85%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	96.15%	91.11%
CHEMBL3137262	O60341	LSD1/CoREST complex	93.18%	97.09%
CHEMBL2581	P07339	Cathepsin D	89.90%	98.95%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	89.14%	85.14%
CHEMBL1293249	Q13887	Kruppel-like factor 5	89.12%	86.33%
CHEMBL241	Q14432	Phosphodiesterase 3A	88.90%	92.94%
CHEMBL1075094	Q16236	Nuclear factor erythroid 2-related factor 2	87.60%	96.00%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	86.51%	89.62%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	86.31%	94.00%
CHEMBL3060	Q9Y345	Glycine transporter 2	86.07%	99.17%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	85.60%	95.56%
CHEMBL220	P22303	Acetylcholinesterase	84.16%	94.45%
CHEMBL1806	P11388	DNA topoisomerase II alpha	83.39%	89.00%
CHEMBL4208	P20618	Proteasome component C5	83.13%	90.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	82.45%	97.14%
CHEMBL4016	P42262	Glutamate receptor ionotropic, AMPA 2	81.77%	86.92%
CHEMBL2373	P21730	C5a anaphylatoxin chemotactic receptor	81.70%	92.62%
CHEMBL5608	Q16288	NT-3 growth factor receptor	80.21%	95.89%

Plants that contains it

• Achlys triphylla
• Albizia procera
• Artemisia giraldii
• Balanophora japonica
• Bulbophyllum protractum
• Calystegia pubescens
• Cypripedium calceolus
• Daphne feddei
• Diospyros japonica
• Hortonia floribunda
• Lactuca sativa
• Lampranthus sociorum
• Perymenium mendezii
• Picea glauca
• Pongamia pinnata
• Protium tonkinense
• Sedum sarmentosum
• Seriphidium porrectum
• Solanum aculeatissimum
• Tarchonanthus camphoratus
• Uncaria rhynchophylla

Cross-Links

• PubChem: 45482330
• NPASS: NPC205796
• LOTUS: LTS0035529
• wikiData: Q105378123