(2R,3S)-2-(3-Methoxy-4-hydroxyphenyl)-5-methoxy-8-[(E)-3-phenylpropenoyl]-3,4-dihydro-2H-1-benzopyran-3,7-diol
| Internal ID | 1384d486-4212-460d-86dc-8d9a49ab838c |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavans > Catechins |
| IUPAC Name | (E)-1-[(2R,3S)-3,7-dihydroxy-2-(4-hydroxy-3-methoxyphenyl)-5-methoxy-3,4-dihydro-2H-chromen-8-yl]-3-phenylprop-2-en-1-one |
| SMILES (Canonical) | COC1=C(C=CC(=C1)C2C(CC3=C(C=C(C(=C3O2)C(=O)C=CC4=CC=CC=C4)O)OC)O)O |
| SMILES (Isomeric) | COC1=C(C=CC(=C1)[C@@H]2[C@H](CC3=C(C=C(C(=C3O2)C(=O)/C=C/C4=CC=CC=C4)O)OC)O)O |
| InChI | InChI=1S/C26H24O7/c1-31-22-14-20(29)24(19(28)10-8-15-6-4-3-5-7-15)26-17(22)13-21(30)25(33-26)16-9-11-18(27)23(12-16)32-2/h3-12,14,21,25,27,29-30H,13H2,1-2H3/b10-8+/t21-,25+/m0/s1 |
| InChI Key | DOVZXLLTBZQJDB-SKDKGQFXSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C26H24O7 |
| Molecular Weight | 448.50 g/mol |
| Exact Mass | 448.15220310 g/mol |
| Topological Polar Surface Area (TPSA) | 105.00 Ų |
| XlogP | 4.40 |
| Atomic LogP (AlogP) | 4.05 |
| H-Bond Acceptor | 7 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 6 |
| There are no found synonyms. |
![2D Structure of (2R,3S)-2-(3-Methoxy-4-hydroxyphenyl)-5-methoxy-8-[(E)-3-phenylpropenoyl]-3,4-dihydro-2H-1-benzopyran-3,7-diol](https://plantaedb.com/storage/docs/compounds/2023/07/3aa9d220-24cd-11ee-84b2-c1c79f9db50b.jpg "2D Structure of (2R,3S)-2-(3-Methoxy-4-hydroxyphenyl)-5-methoxy-8-[(E)-3-phenylpropenoyl]-3,4-dihydro-2H-1-benzopyran-3,7-diol")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9845 | 98.45% |
| Caco-2 | - | 0.6417 | 64.17% |
| Blood Brain Barrier | - | 0.7000 | 70.00% |
| Human oral bioavailability | - | 0.7286 | 72.86% |
| Subcellular localzation | Mitochondria | 0.6754 | 67.54% |
| OATP2B1 inhibitior | - | 0.8531 | 85.31% |
| OATP1B1 inhibitior | + | 0.9024 | 90.24% |
| OATP1B3 inhibitior | + | 0.9621 | 96.21% |
| MATE1 inhibitior | - | 0.9400 | 94.00% |
| OCT2 inhibitior | - | 0.9500 | 95.00% |
| BSEP inhibitior | + | 0.9266 | 92.66% |
| P-glycoprotein inhibitior | + | 0.8975 | 89.75% |
| P-glycoprotein substrate | - | 0.7498 | 74.98% |
| CYP3A4 substrate | + | 0.5856 | 58.56% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8017 | 80.17% |
| CYP3A4 inhibition | + | 0.5255 | 52.55% |
| CYP2C9 inhibition | - | 0.5052 | 50.52% |
| CYP2C19 inhibition | + | 0.6531 | 65.31% |
| CYP2D6 inhibition | - | 0.7480 | 74.80% |
| CYP1A2 inhibition | + | 0.5938 | 59.38% |
| CYP2C8 inhibition | + | 0.7611 | 76.11% |
| CYP inhibitory promiscuity | + | 0.6687 | 66.87% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.9900 | 99.00% |
| Carcinogenicity (trinary) | Non-required | 0.5213 | 52.13% |
| Eye corrosion | - | 0.9880 | 98.80% |
| Eye irritation | - | 0.7462 | 74.62% |
| Skin irritation | - | 0.7257 | 72.57% |
| Skin corrosion | - | 0.9565 | 95.65% |
| Ames mutagenesis | - | 0.6654 | 66.54% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.7211 | 72.11% |
| Micronuclear | + | 0.8100 | 81.00% |
| Hepatotoxicity | - | 0.7592 | 75.92% |
| skin sensitisation | - | 0.8558 | 85.58% |
| Respiratory toxicity | + | 0.6667 | 66.67% |
| Reproductive toxicity | + | 0.8778 | 87.78% |
| Mitochondrial toxicity | + | 0.6375 | 63.75% |
| Nephrotoxicity | - | 0.7034 | 70.34% |
| Acute Oral Toxicity (c) | III | 0.4694 | 46.94% |
| Estrogen receptor binding | + | 0.8391 | 83.91% |
| Androgen receptor binding | + | 0.7813 | 78.13% |
| Thyroid receptor binding | + | 0.6570 | 65.70% |
| Glucocorticoid receptor binding | + | 0.7542 | 75.42% |
| Aromatase binding | - | 0.5220 | 52.20% |
| PPAR gamma | + | 0.7435 | 74.35% |
| Honey bee toxicity | - | 0.8522 | 85.22% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | - | 0.5900 | 59.00% |
| Fish aquatic toxicity | + | 0.8788 | 87.88% |
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 | 99.47% | 91.11% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 97.65% | 96.09% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 96.48% | 95.56% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 95.69% | 86.33% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 93.96% | 85.14% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 93.33% | 89.00% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 91.86% | 96.00% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 88.77% | 97.09% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 88.53% | 95.50% |
| CHEMBL3194 | P02766 | Transthyretin | 87.64% | 90.71% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 86.75% | 99.17% |
| CHEMBL2002 | P12268 | Inosine-5'-monophosphate dehydrogenase 2 | 85.81% | 98.21% |
| CHEMBL2535 | P11166 | Glucose transporter | 85.64% | 98.75% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 85.22% | 94.73% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 85.06% | 99.23% |
| CHEMBL5028 | O14672 | ADAM10 | 82.37% | 97.50% |
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