2-{4-[4-(3,4-Dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-3-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

Details

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Internal ID b9288f7f-5ef5-4aa6-ac4a-9df9a0d79700
Taxonomy Lignans, neolignans and related compounds > Lignan glycosides
IUPAC Name 2-[4-[3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-3-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES (Canonical) COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=C(C=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)OC
SMILES (Isomeric) COC1=C(C=C(C=C1)C2C3COC(C3CO2)C4=C(C=C(C=C4)OC5C(C(C(C(O5)CO)O)O)O)OC)OC
InChI InChI=1S/C27H34O11/c1-32-18-7-4-13(8-20(18)34-3)25-16-11-36-26(17(16)12-35-25)15-6-5-14(9-19(15)33-2)37-27-24(31)23(30)22(29)21(10-28)38-27/h4-9,16-17,21-31H,10-12H2,1-3H3
InChI Key ZTIZEXUIEBLYBL-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C27H34O11
Molecular Weight 534.60 g/mol
Exact Mass 534.21011190 g/mol
Topological Polar Surface Area (TPSA) 146.00 Ų
XlogP 0.80
Atomic LogP (AlogP) 0.97
H-Bond Acceptor 11
H-Bond Donor 4
Rotatable Bonds 8

Synonyms

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PD056285
A827597
(2S,3R,4S,5S,6R)-2-[4-[(3R,3aR,6S,6aR)-3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-3-methoxyphenoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
2-[4-[3-(3,4-dimethoxyphenyl)-1,3,3a,4,6,6a-hexahydrofuro[3,4-c]furan-6-yl]-3-methoxy-phenoxy]-6-(hydroxymethyl)tetrahydropyran-3,4,5-triol;Phillyrin

2D Structure

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2D Structure of 2-{4-[4-(3,4-Dimethoxyphenyl)-hexahydrofuro[3,4-c]furan-1-yl]-3-methoxyphenoxy}-6-(hydroxymethyl)oxane-3,4,5-triol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.5448 54.48%
Caco-2 - 0.8032 80.32%
Blood Brain Barrier - 0.6000 60.00%
Human oral bioavailability - 0.5857 58.57%
Subcellular localzation Mitochondria 0.7094 70.94%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.9106 91.06%
OATP1B3 inhibitior + 0.9657 96.57%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.7500 75.00%
BSEP inhibitior + 0.6433 64.33%
P-glycoprotein inhibitior + 0.6408 64.08%
P-glycoprotein substrate - 0.6910 69.10%
CYP3A4 substrate + 0.6423 64.23%
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 + 0.6386 63.86%
CYP inhibitory promiscuity - 0.5471 54.71%
UGT catelyzed - 0.5000 50.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.5993 59.93%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9403 94.03%
Skin irritation - 0.8460 84.60%
Skin corrosion - 0.9592 95.92%
Ames mutagenesis - 0.5300 53.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8725 87.25%
Micronuclear + 0.5700 57.00%
Hepatotoxicity - 0.9000 90.00%
skin sensitisation - 0.8954 89.54%
Respiratory toxicity + 0.5667 56.67%
Reproductive toxicity + 0.8000 80.00%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity - 0.8667 86.67%
Acute Oral Toxicity (c) III 0.6521 65.21%
Estrogen receptor binding + 0.7363 73.63%
Androgen receptor binding + 0.6000 60.00%
Thyroid receptor binding + 0.6120 61.20%
Glucocorticoid receptor binding + 0.6589 65.89%
Aromatase binding - 0.5593 55.93%
PPAR gamma + 0.5498 54.98%
Honey bee toxicity - 0.8343 83.43%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.7200 72.00%
Fish aquatic toxicity + 0.9093 90.93%

Targets

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Proven Targets:

CHEMBL ID UniProt ID Name Min activity Assay type Source
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 99.05% 96.09%
CHEMBL3137262 O60341 LSD1/CoREST complex 96.92% 97.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 96.62% 91.11%
CHEMBL1293249 Q13887 Kruppel-like factor 5 93.83% 86.33%
CHEMBL220 P22303 Acetylcholinesterase 91.89% 94.45%
CHEMBL2581 P07339 Cathepsin D 91.79% 98.95%
CHEMBL241 Q14432 Phosphodiesterase 3A 90.96% 92.94%
CHEMBL5608 Q16288 NT-3 growth factor receptor 90.89% 95.89%
CHEMBL3060 Q9Y345 Glycine transporter 2 90.70% 99.17%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 87.87% 96.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 87.39% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 86.78% 95.56%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 85.32% 86.92%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 85.03% 95.89%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 84.75% 85.14%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 84.46% 92.62%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 83.59% 89.62%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.34% 89.00%
CHEMBL4208 P20618 Proteasome component C5 83.14% 90.00%
CHEMBL2535 P11166 Glucose transporter 82.37% 98.75%
CHEMBL3880 P07900 Heat shock protein HSP 90-alpha 81.05% 96.21%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 80.61% 97.14%
CHEMBL2335 P42785 Lysosomal Pro-X carboxypeptidase 80.15% 100.00%

Plants that contains it

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Below are displayed all the plants proven (via scientific papers) to contain this compound!
To see more specific details click the taxa you are interested in.
Forsythia suspensa

Cross-Links

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PubChem 53395135
NPASS NPC165256