[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

Details

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Internal ID eebcc91d-c039-45d4-bbb0-c391b2fe01f3
Taxonomy Phenylpropanoids and polyketides > Tannins > Hydrolyzable tannins
IUPAC Name [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate
SMILES (Canonical) COC1=CC(=CC(=C1OC)OC)OC2C(C(C(C(O2)COC(=O)C3=CC(=C(C=C3)O)OC)O)O)O
SMILES (Isomeric) COC1=CC(=CC(=C1OC)OC)O[C@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C3=CC(=C(C=C3)O)OC)O)O)O
InChI InChI=1S/C23H28O12/c1-29-14-7-11(5-6-13(14)24)22(28)33-10-17-18(25)19(26)20(27)23(35-17)34-12-8-15(30-2)21(32-4)16(9-12)31-3/h5-9,17-20,23-27H,10H2,1-4H3/t17-,18-,19+,20-,23-/m1/s1
InChI Key KDMAVPMMVXQQGH-DUXQTRJFSA-N
Popularity 2 references in papers

Physical and Chemical Properties

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Molecular Formula C23H28O12
Molecular Weight 496.50 g/mol
Exact Mass 496.15807632 g/mol
Topological Polar Surface Area (TPSA) 163.00 Ų
XlogP 1.00
Atomic LogP (AlogP) 0.47
H-Bond Acceptor 12
H-Bond Donor 4
Rotatable Bonds 9

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of [(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-(3,4,5-trimethoxyphenoxy)oxan-2-yl]methyl 4-hydroxy-3-methoxybenzoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption - 0.6886 68.86%
Caco-2 - 0.7578 75.78%
Blood Brain Barrier - 0.6750 67.50%
Human oral bioavailability - 0.5571 55.71%
Subcellular localzation Mitochondria 0.7123 71.23%
OATP2B1 inhibitior - 0.8596 85.96%
OATP1B1 inhibitior + 0.9133 91.33%
OATP1B3 inhibitior + 0.8713 87.13%
MATE1 inhibitior - 0.8400 84.00%
OCT2 inhibitior - 0.7250 72.50%
BSEP inhibitior + 0.6636 66.36%
P-glycoprotein inhibitior + 0.5870 58.70%
P-glycoprotein substrate - 0.8726 87.26%
CYP3A4 substrate + 0.5667 56.67%
CYP2C9 substrate - 1.0000 100.00%
CYP2D6 substrate - 0.8398 83.98%
CYP3A4 inhibition - 0.8469 84.69%
CYP2C9 inhibition - 0.8632 86.32%
CYP2C19 inhibition - 0.8752 87.52%
CYP2D6 inhibition - 0.8817 88.17%
CYP1A2 inhibition - 0.7911 79.11%
CYP2C8 inhibition + 0.7835 78.35%
CYP inhibitory promiscuity - 0.6920 69.20%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9700 97.00%
Carcinogenicity (trinary) Non-required 0.7306 73.06%
Eye corrosion - 0.9894 98.94%
Eye irritation - 0.8523 85.23%
Skin irritation - 0.8627 86.27%
Skin corrosion - 0.9678 96.78%
Ames mutagenesis - 0.7300 73.00%
Human Ether-a-go-go-Related Gene inhibition - 0.4476 44.76%
Micronuclear + 0.6366 63.66%
Hepatotoxicity - 0.8125 81.25%
skin sensitisation - 0.9208 92.08%
Respiratory toxicity - 0.6778 67.78%
Reproductive toxicity + 0.6222 62.22%
Mitochondrial toxicity - 0.6500 65.00%
Nephrotoxicity - 0.9109 91.09%
Acute Oral Toxicity (c) III 0.7836 78.36%
Estrogen receptor binding + 0.7793 77.93%
Androgen receptor binding - 0.5599 55.99%
Thyroid receptor binding + 0.6755 67.55%
Glucocorticoid receptor binding + 0.7887 78.87%
Aromatase binding + 0.5752 57.52%
PPAR gamma + 0.5872 58.72%
Honey bee toxicity - 0.8903 89.03%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.6449 64.49%
Fish aquatic toxicity + 0.8292 82.92%

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 97.51% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 96.67% 96.09%
CHEMBL3060 Q9Y345 Glycine transporter 2 94.41% 99.17%
CHEMBL4208 P20618 Proteasome component C5 92.01% 90.00%
CHEMBL2635 P51452 Dual specificity protein phosphatase 3 90.75% 94.00%
CHEMBL1293249 Q13887 Kruppel-like factor 5 90.47% 86.33%
CHEMBL1075094 Q16236 Nuclear factor erythroid 2-related factor 2 89.00% 96.00%
CHEMBL3194 P02766 Transthyretin 87.24% 90.71%
CHEMBL2535 P11166 Glucose transporter 85.52% 98.75%
CHEMBL3401 O75469 Pregnane X receptor 84.97% 94.73%
CHEMBL1806 P11388 DNA topoisomerase II alpha 84.28% 89.00%
CHEMBL225 P28335 Serotonin 2c (5-HT2c) receptor 84.06% 89.62%
CHEMBL5608 Q16288 NT-3 growth factor receptor 82.80% 95.89%
CHEMBL2373 P21730 C5a anaphylatoxin chemotactic receptor 81.63% 92.62%

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.
Betula pubescens
Tetracentron sinense

Cross-Links

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PubChem 11972477
LOTUS LTS0156714
wikiData Q105139225