methyl 3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-6-yl]-3-(2,4,5-trihydroxyphenyl)propanoate

Details

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Internal ID 28497ea5-a5b9-4542-996a-5a68a0666ac2
Taxonomy Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins
IUPAC Name methyl 3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-6-yl]-3-(2,4,5-trihydroxyphenyl)propanoate
SMILES (Canonical) COC(=O)CC(C1=CC(=C(C=C1O)O)O)C2=C(C3=C(C=C2O)OC(C(C3)O)C4=CC(=C(C=C4)O)O)O
SMILES (Isomeric) COC(=O)CC(C1=CC(=C(C=C1O)O)O)C2=C(C3=C(C=C2O)OC(C(C3)O)C4=CC(=C(C=C4)O)O)O
InChI InChI=1S/C25H24O11/c1-35-22(33)7-12(11-5-17(29)18(30)8-15(11)27)23-19(31)9-21-13(24(23)34)6-20(32)25(36-21)10-2-3-14(26)16(28)4-10/h2-5,8-9,12,20,25-32,34H,6-7H2,1H3
InChI Key ZEIXYPCJVUBRJI-UHFFFAOYSA-N
Popularity 0 references in papers

Physical and Chemical Properties

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Molecular Formula C25H24O11
Molecular Weight 500.40 g/mol
Exact Mass 500.13186158 g/mol
Topological Polar Surface Area (TPSA) 197.00 Ų
XlogP 0.80
Atomic LogP (AlogP) 2.36
H-Bond Acceptor 11
H-Bond Donor 8
Rotatable Bonds 5

Synonyms

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There are no found synonyms.

2D Structure

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2D Structure of methyl 3-[2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-chromen-6-yl]-3-(2,4,5-trihydroxyphenyl)propanoate

3D Structure

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ADMET Properties (via admetSAR 2)

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Target Value Probability (raw) Probability (%)
Human Intestinal Absorption + 0.8109 81.09%
Caco-2 - 0.8733 87.33%
Blood Brain Barrier - 0.7750 77.50%
Human oral bioavailability - 0.8143 81.43%
Subcellular localzation Mitochondria 0.5064 50.64%
OATP2B1 inhibitior - 0.5642 56.42%
OATP1B1 inhibitior + 0.8811 88.11%
OATP1B3 inhibitior + 0.9061 90.61%
MATE1 inhibitior - 0.8000 80.00%
OCT2 inhibitior - 0.8250 82.50%
BSEP inhibitior + 0.9705 97.05%
P-glycoprotein inhibitior - 0.4483 44.83%
P-glycoprotein substrate - 0.6330 63.30%
CYP3A4 substrate + 0.6230 62.30%
CYP2C9 substrate - 0.6194 61.94%
CYP2D6 substrate - 0.7009 70.09%
CYP3A4 inhibition - 0.8673 86.73%
CYP2C9 inhibition - 0.9325 93.25%
CYP2C19 inhibition - 0.9018 90.18%
CYP2D6 inhibition - 0.8453 84.53%
CYP1A2 inhibition - 0.7782 77.82%
CYP2C8 inhibition + 0.5122 51.22%
CYP inhibitory promiscuity - 0.8262 82.62%
UGT catelyzed + 0.6000 60.00%
Carcinogenicity (binary) - 0.9900 99.00%
Carcinogenicity (trinary) Non-required 0.6374 63.74%
Eye corrosion - 0.9893 98.93%
Eye irritation - 0.8749 87.49%
Skin irritation - 0.7084 70.84%
Skin corrosion - 0.9365 93.65%
Ames mutagenesis - 0.6700 67.00%
Human Ether-a-go-go-Related Gene inhibition + 0.8648 86.48%
Micronuclear + 0.6518 65.18%
Hepatotoxicity - 0.6125 61.25%
skin sensitisation - 0.9199 91.99%
Respiratory toxicity + 0.7444 74.44%
Reproductive toxicity + 0.9444 94.44%
Mitochondrial toxicity + 0.8000 80.00%
Nephrotoxicity - 0.7502 75.02%
Acute Oral Toxicity (c) III 0.5489 54.89%
Estrogen receptor binding + 0.8375 83.75%
Androgen receptor binding + 0.7417 74.17%
Thyroid receptor binding + 0.6459 64.59%
Glucocorticoid receptor binding + 0.7984 79.84%
Aromatase binding - 0.4889 48.89%
PPAR gamma + 0.6475 64.75%
Honey bee toxicity - 0.8460 84.60%
Biodegradation - 0.9000 90.00%
Crustacea aquatic toxicity - 0.5800 58.00%
Fish aquatic toxicity + 0.8951 89.51%

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 99.76% 91.11%
CHEMBL3251 P19838 Nuclear factor NF-kappa-B p105 subunit 99.23% 96.09%
CHEMBL1951 P21397 Monoamine oxidase A 99.03% 91.49%
CHEMBL4261 Q16665 Hypoxia-inducible factor 1 alpha 97.23% 85.14%
CHEMBL2581 P07339 Cathepsin D 94.46% 98.95%
CHEMBL1806 P11388 DNA topoisomerase II alpha 88.96% 89.00%
CHEMBL3231 Q13464 Rho-associated protein kinase 1 88.79% 95.55%
CHEMBL4203 Q9HAZ1 Dual specificity protein kinase CLK4 88.61% 94.45%
CHEMBL1293249 Q13887 Kruppel-like factor 5 88.51% 86.33%
CHEMBL3401 O75469 Pregnane X receptor 88.19% 94.73%
CHEMBL3060 Q9Y345 Glycine transporter 2 86.26% 99.17%
CHEMBL3137262 O60341 LSD1/CoREST complex 85.53% 97.09%
CHEMBL5845 P23415 Glycine receptor subunit alpha-1 84.93% 90.71%
CHEMBL1860 P10827 Thyroid hormone receptor alpha 83.64% 99.15%
CHEMBL2535 P11166 Glucose transporter 81.30% 98.75%
CHEMBL3108638 O15164 Transcription intermediary factor 1-alpha 81.23% 95.56%

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.
Smilax china

Cross-Links

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PubChem 162901501
LOTUS LTS0200965
wikiData Q105373299