2-[4-[(2R,3S)-3-(Hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydrobenzofuran-2-yl]-2,6-dimethoxy-phenoxy]propane-1,3-diol

Details

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Internal ID 29a6c3bd-4942-4b47-b244-7ca845f6feb5
Taxonomy Phenylpropanoids and polyketides > 2-arylbenzofuran flavonoids
IUPAC Name 2-[4-[(2R,3S)-3-(hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydro-1-benzofuran-2-yl]-2,6-dimethoxyphenoxy]propane-1,3-diol
SMILES (Canonical) COC1=CC(=CC2=C1OC(C2CO)C3=CC(=C(C(=C3)OC)OC(CO)CO)OC)CCCO
SMILES (Isomeric) COC1=CC(=CC2=C1O[C@H]([C@@H]2CO)C3=CC(=C(C(=C3)OC)OC(CO)CO)OC)CCCO
InChI InChI=1S/C24H32O9/c1-29-19-8-14(5-4-6-25)7-17-18(13-28)22(33-23(17)19)15-9-20(30-2)24(21(10-15)31-3)32-16(11-26)12-27/h7-10,16,18,22,25-28H,4-6,11-13H2,1-3H3/t18-,22+/m1/s1
InChI Key UDNVBKBWANAIGZ-GCJKJVERSA-N
Popularity 1 reference in papers

Physical and Chemical Properties

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Molecular Formula C24H32O9
Molecular Weight 464.50 g/mol
Exact Mass 464.20463259 g/mol
Topological Polar Surface Area (TPSA) 127.00 Ų
XlogP 1.10
Atomic LogP (AlogP) 1.58
H-Bond Acceptor 9
H-Bond Donor 4
Rotatable Bonds 12

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of 2-[4-[(2R,3S)-3-(Hydroxymethyl)-5-(3-hydroxypropyl)-7-methoxy-2,3-dihydrobenzofuran-2-yl]-2,6-dimethoxy-phenoxy]propane-1,3-diol

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.9670 96.70%
Caco-2 + 0.5074 50.74%
Blood Brain Barrier + 0.5500 55.00%
Human oral bioavailability - 0.6429 64.29%
Subcellular localzation Mitochondria 0.6611 66.11%
OATP2B1 inhibitior - 0.8622 86.22%
OATP1B1 inhibitior + 0.8259 82.59%
OATP1B3 inhibitior + 0.9213 92.13%
MATE1 inhibitior - 0.9800 98.00%
OCT2 inhibitior - 0.8750 87.50%
BSEP inhibitior + 0.8400 84.00%
P-glycoprotein inhibitior + 0.7062 70.62%
P-glycoprotein substrate + 0.5061 50.61%
CYP3A4 substrate + 0.6304 63.04%
CYP2C9 substrate - 0.8037 80.37%
CYP2D6 substrate + 0.5414 54.14%
CYP3A4 inhibition - 0.6855 68.55%
CYP2C9 inhibition - 0.6288 62.88%
CYP2C19 inhibition - 0.6808 68.08%
CYP2D6 inhibition - 0.9026 90.26%
CYP1A2 inhibition - 0.5790 57.90%
CYP2C8 inhibition + 0.7274 72.74%
CYP inhibitory promiscuity + 0.6492 64.92%
UGT catelyzed - 0.6000 60.00%
Carcinogenicity (binary) - 0.9200 92.00%
Carcinogenicity (trinary) Non-required 0.5921 59.21%
Eye corrosion - 0.9902 99.02%
Eye irritation - 0.9053 90.53%
Skin irritation - 0.8201 82.01%
Skin corrosion - 0.9502 95.02%
Ames mutagenesis - 0.6000 60.00%
Human Ether-a-go-go-Related Gene inhibition + 0.6696 66.96%
Micronuclear - 0.5441 54.41%
Hepatotoxicity - 0.6322 63.22%
skin sensitisation - 0.8479 84.79%
Respiratory toxicity + 0.6556 65.56%
Reproductive toxicity + 0.8222 82.22%
Mitochondrial toxicity + 0.6750 67.50%
Nephrotoxicity - 0.5790 57.90%
Acute Oral Toxicity (c) III 0.6715 67.15%
Estrogen receptor binding + 0.8636 86.36%
Androgen receptor binding + 0.6287 62.87%
Thyroid receptor binding + 0.7701 77.01%
Glucocorticoid receptor binding + 0.7923 79.23%
Aromatase binding + 0.5984 59.84%
PPAR gamma + 0.5784 57.84%
Honey bee toxicity - 0.8225 82.25%
Biodegradation - 0.8000 80.00%
Crustacea aquatic toxicity - 0.7155 71.55%
Fish aquatic toxicity - 0.5000 50.00%

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 98.84% 96.09%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 96.29% 85.14%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.72% 99.17%
CHEMBL4016 P42262 Glutamate receptor ionotropic, AMPA 2 91.98% 86.92%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.89% 86.33%
CHEMBL2581 P07339 Cathepsin D 90.47% 98.95%
CHEMBL1907603 Q05586 Glutamate NMDA receptor; GRIN1/GRIN2B 88.46% 95.89%
CHEMBL5619 P27695 DNA-(apurinic or apyrimidinic site) lyase 87.42% 91.11%
CHEMBL1966 Q02127 Dihydroorotate dehydrogenase 86.44% 96.09%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 85.52% 95.56%
CHEMBL4302 P08183 P-glycoprotein 1 84.11% 92.98%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 83.94% 92.62%
CHEMBL3401 O75469 Pregnane X receptor 83.52% 94.73%
CHEMBL4478 Q00975 Voltage-gated N-type calcium channel alpha-1B subunit 83.02% 97.14%

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.
Epimedium wushanense
Illicium difengpi
Rosa chinensis var. spontanea

Cross-Links

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PubChem 71591634
NPASS NPC185378
LOTUS LTS0240731
wikiData Q104402218