5-[(2S,3S)-4-[(E)-2-(2-hydroxyphenyl)ethenyl]-6-methoxy-3-phenyl-2,3-dihydro-1-benzofuran-2-yl]-3-methoxybenzene-1,2-diol

Details

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Internal ID a1f3224e-c83a-49ef-aed1-0e6f7f2ac7e4
Taxonomy Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
IUPAC Name 5-[(2S,3S)-4-[(E)-2-(2-hydroxyphenyl)ethenyl]-6-methoxy-3-phenyl-2,3-dihydro-1-benzofuran-2-yl]-3-methoxybenzene-1,2-diol
SMILES (Canonical) COC1=CC(=C2C(C(OC2=C1)C3=CC(=C(C(=C3)OC)O)O)C4=CC=CC=C4)C=CC5=CC=CC=C5O
SMILES (Isomeric) COC1=CC(=C2[C@@H]([C@H](OC2=C1)C3=CC(=C(C(=C3)OC)O)O)C4=CC=CC=C4)/C=C/C5=CC=CC=C5O
InChI InChI=1S/C30H26O6/c1-34-22-14-20(13-12-18-8-6-7-11-23(18)31)27-25(17-22)36-30(28(27)19-9-4-3-5-10-19)21-15-24(32)29(33)26(16-21)35-2/h3-17,28,30-33H,1-2H3/b13-12+/t28-,30+/m0/s1
InChI Key DHSYWCGWVLXVOY-DNTBLHPTSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C30H26O6
Molecular Weight 482.50 g/mol
Exact Mass 482.17293854 g/mol
Topological Polar Surface Area (TPSA) 88.40 Ų
XlogP 6.10
Atomic LogP (AlogP) 6.26
H-Bond Acceptor 6
H-Bond Donor 3
Rotatable Bonds 6

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 5-[(2S,3S)-4-[(E)-2-(2-hydroxyphenyl)ethenyl]-6-methoxy-3-phenyl-2,3-dihydro-1-benzofuran-2-yl]-3-methoxybenzene-1,2-diol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9856 98.56%
Caco-2 - 0.6587 65.87%
Blood Brain Barrier - 0.5500 55.00%
Human oral bioavailability - 0.7571 75.71%
Subcellular localzation Mitochondria 0.6404 64.04%
OATP2B1 inhibitior - 0.7173 71.73%
OATP1B1 inhibitior + 0.8524 85.24%
OATP1B3 inhibitior + 0.9759 97.59%
MATE1 inhibitior - 0.9200 92.00%
OCT2 inhibitior - 0.9250 92.50%
BSEP inhibitior + 0.8925 89.25%
P-glycoprotein inhibitior + 0.8402 84.02%
P-glycoprotein substrate - 0.7675 76.75%
CYP3A4 substrate + 0.5434 54.34%
CYP2C9 substrate + 0.6176 61.76%
CYP2D6 substrate - 0.6658 66.58%
CYP3A4 inhibition + 0.5000 50.00%
CYP2C9 inhibition + 0.7750 77.50%
CYP2C19 inhibition + 0.8265 82.65%
CYP2D6 inhibition - 0.7276 72.76%
CYP1A2 inhibition + 0.8192 81.92%
CYP2C8 inhibition + 0.8229 82.29%
CYP inhibitory promiscuity + 0.9323 93.23%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9008 90.08%
Carcinogenicity (trinary) Danger 0.4292 42.92%
Eye corrosion - 0.9877 98.77%
Eye irritation - 0.7179 71.79%
Skin irritation - 0.7279 72.79%
Skin corrosion - 0.9315 93.15%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8463 84.63%
Micronuclear + 0.8500 85.00%
Hepatotoxicity - 0.6091 60.91%
skin sensitisation - 0.7766 77.66%
Respiratory toxicity + 0.5222 52.22%
Reproductive toxicity + 0.7000 70.00%
Mitochondrial toxicity + 0.6500 65.00%
Nephrotoxicity - 0.7773 77.73%
Acute Oral Toxicity (c) III 0.4862 48.62%
Estrogen receptor binding + 0.8117 81.17%
Androgen receptor binding + 0.7845 78.45%
Thyroid receptor binding + 0.7844 78.44%
Glucocorticoid receptor binding + 0.8296 82.96%
Aromatase binding + 0.5533 55.33%
PPAR gamma + 0.7415 74.15%
Honey bee toxicity - 0.8764 87.64%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5900 59.00%
Fish aquatic toxicity + 0.9797 97.97%

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
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 99.52% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.99% 85.14%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 95.14% 95.56%
CHEMBL3194 P02766 Transthyretin 92.31% 90.71%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 92.30% 96.09%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 91.72% 99.15%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 91.42% 96.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.37% 86.33%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 86.80% 92.62%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.11% 94.00%
CHEMBL3401 O75469 Pregnane X receptor 83.53% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 83.32% 89.00%
CHEMBL4208 P20618 Proteasome component C5 82.00% 90.00%
CHEMBL3192 Q9BY41 Histone deacetylase 8 80.44% 93.99%
CHEMBL3060 Q9Y345 Glycine transporter 2 80.24% 99.17%
CHEMBL2716 Q8WUI4 Histone deacetylase 7 80.17% 89.44%

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.
Phragmipedium longifolium

Cross-Links

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PubChem 16736257
LOTUS LTS0011266
wikiData Q104980822