(2R,3R,4R,5R,6S)-2-[[(2R,3S)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy]-6-methyloxane-3,4,5-triol

Details

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Internal ID aba79519-ccff-4bf7-8bf7-0720936a364b
Taxonomy Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
IUPAC Name (2R,3R,4R,5R,6S)-2-[[(2R,3S)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy]-6-methyloxane-3,4,5-triol
SMILES (Canonical) CC1C(C(C(C(O1)OCC2C(OC3=C2C=C(C=C3OC)CCCO)C4=CC(=C(C(=C4)OC)O)OC)O)O)O
SMILES (Isomeric) C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC[C@H]2[C@@H](OC3=C2C=C(C=C3OC)CCCO)C4=CC(=C(C(=C4)OC)O)OC)O)O)O
InChI InChI=1S/C27H36O11/c1-13-21(29)23(31)24(32)27(37-13)36-12-17-16-8-14(6-5-7-28)9-20(35-4)26(16)38-25(17)15-10-18(33-2)22(30)19(11-15)34-3/h8-11,13,17,21,23-25,27-32H,5-7,12H2,1-4H3/t13-,17+,21-,23+,24+,25-,27+/m0/s1
InChI Key DAPCPLQFHONFRT-LTSUAKQISA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C27H36O11
Molecular Weight 536.60 g/mol
Exact Mass 536.22576196 g/mol
Topological Polar Surface Area (TPSA) 157.00 Ų
XlogP 1.00
Atomic LogP (AlogP) 1.40
H-Bond Acceptor 11
H-Bond Donor 5
Rotatable Bonds 10

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of (2R,3R,4R,5R,6S)-2-[[(2R,3S)-2-(4-hydroxy-3,5-dimethoxyphenyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-3-yl]methoxy]-6-methyloxane-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 + 0.5447 54.47%
Caco-2 - 0.7885 78.85%
Blood Brain Barrier - 0.7000 70.00%
Human oral bioavailability - 0.7429 74.29%
Subcellular localzation Mitochondria 0.6493 64.93%
OATP2B1 inhibitior - 1.0000 100.00%
OATP1B1 inhibitior + 0.7573 75.73%
OATP1B3 inhibitior + 0.9565 95.65%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.6236 62.36%
P-glycoprotein inhibitior - 0.5653 56.53%
P-glycoprotein substrate + 0.6152 61.52%
CYP3A4 substrate + 0.6528 65.28%
CYP2C9 substrate - 0.7915 79.15%
CYP2D6 substrate - 0.7682 76.82%
CYP3A4 inhibition - 0.9385 93.85%
CYP2C9 inhibition - 0.8482 84.82%
CYP2C19 inhibition - 0.8708 87.08%
CYP2D6 inhibition - 0.8984 89.84%
CYP1A2 inhibition - 0.8431 84.31%
CYP2C8 inhibition + 0.8043 80.43%
CYP inhibitory promiscuity - 0.7137 71.37%
UGT catelyzed + 0.7000 70.00%
Carcinogenicity (binary) - 0.9500 95.00%
Carcinogenicity (trinary) Non-required 0.5736 57.36%
Eye corrosion - 0.9906 99.06%
Eye irritation - 0.9322 93.22%
Skin irritation - 0.8226 82.26%
Skin corrosion - 0.9499 94.99%
Ames mutagenesis - 0.5800 58.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6877 68.77%
Micronuclear - 0.5341 53.41%
Hepatotoxicity - 0.7572 75.72%
skin sensitisation - 0.8981 89.81%
Respiratory toxicity + 0.5444 54.44%
Reproductive toxicity + 0.8556 85.56%
Mitochondrial toxicity + 0.6625 66.25%
Nephrotoxicity - 0.8800 88.00%
Acute Oral Toxicity (c) III 0.7076 70.76%
Estrogen receptor binding + 0.7699 76.99%
Androgen receptor binding + 0.5302 53.02%
Thyroid receptor binding + 0.6013 60.13%
Glucocorticoid receptor binding + 0.7456 74.56%
Aromatase binding + 0.5499 54.99%
PPAR gamma + 0.5294 52.94%
Honey bee toxicity - 0.8303 83.03%
Biodegradation - 0.7500 75.00%
Crustacea aquatic toxicity - 0.7800 78.00%
Fish aquatic toxicity - 0.4925 49.25%

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 99.02% 96.09%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 98.97% 91.11%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 98.34% 85.14%
CHEMBL3714130 P46095 G-protein coupled receptor 6 94.72% 97.36%
CHEMBL2581 P07339 Cathepsin D 94.54% 98.95%
CHEMBL1293249 Q13887 Kruppel-like factor 5 92.61% 86.33%
CHEMBL3060 Q9Y345 Glycine transporter 2 92.47% 99.17%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 89.94% 86.92%
CHEMBL3401 O75469 Pregnane X receptor 89.94% 94.73%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 89.44% 95.89%
CHEMBL1806 P11388 DNA topoisomerase II alpha 85.42% 89.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 84.44% 94.00%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 83.36% 95.56%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.77% 92.62%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 81.62% 96.00%
CHEMBL5608 Q16288 NT-3 growth factor receptor 80.01% 95.89%

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.
Chaenomeles sinensis

Cross-Links

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PubChem 122179011
LOTUS LTS0011428
wikiData Q104973803