2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
| Internal ID | 70a35bf0-7ff7-4471-b661-f4c2c1626ccc |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid C-glycosides > Flavonoid 8-C-glycosides |
| IUPAC Name | 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one |
| SMILES (Canonical) | C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O)O)O |
| SMILES (Isomeric) | C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)[C@H]4[C@@H](C([C@@H](C(O4)CO)O)O)O)O)O |
| InChI | InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14?,17-,18?,19-,21+/m1/s1 |
| InChI Key | PLAPMLGJVGLZOV-ASUBHRBBSA-N |
| Popularity | 128 references in papers |
| Molecular Formula | C21H20O11 |
| Molecular Weight | 448.40 g/mol |
| Exact Mass | 448.10056145 g/mol |
| Topological Polar Surface Area (TPSA) | 197.00 Ų |
| XlogP | -0.20 |
| Atomic LogP (AlogP) | -0.20 |
| H-Bond Acceptor | 11 |
| H-Bond Donor | 8 |
| Rotatable Bonds | 3 |
| 8-beta-D-Glucopyranosyl-3',4',5,7-tetrahydroxyflavone |
| LMPK12110470 |
![2D Structure of 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one](https://plantaedb.com/storage/docs/compounds/2023/07/f04ddca0-248c-11ee-bc58-2d03095c1434.jpg "2D Structure of 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.6665 | 66.65% |
| Caco-2 | - | 0.8974 | 89.74% |
| Blood Brain Barrier | - | 0.7000 | 70.00% |
| Human oral bioavailability | - | 0.6571 | 65.71% |
| Subcellular localzation | Mitochondria | 0.5728 | 57.28% |
| OATP2B1 inhibitior | + | 0.5939 | 59.39% |
| OATP1B1 inhibitior | + | 0.8854 | 88.54% |
| OATP1B3 inhibitior | + | 0.9709 | 97.09% |
| MATE1 inhibitior | - | 0.7400 | 74.00% |
| OCT2 inhibitior | - | 0.8000 | 80.00% |
| BSEP inhibitior | - | 0.5421 | 54.21% |
| P-glycoprotein inhibitior | - | 0.6960 | 69.60% |
| P-glycoprotein substrate | - | 0.8345 | 83.45% |
| CYP3A4 substrate | + | 0.5432 | 54.32% |
| CYP2C9 substrate | - | 0.6301 | 63.01% |
| CYP2D6 substrate | - | 0.8452 | 84.52% |
| CYP3A4 inhibition | - | 0.8310 | 83.10% |
| CYP2C9 inhibition | - | 0.9071 | 90.71% |
| CYP2C19 inhibition | - | 0.9240 | 92.40% |
| CYP2D6 inhibition | - | 0.9476 | 94.76% |
| CYP1A2 inhibition | - | 0.8355 | 83.55% |
| CYP2C8 inhibition | + | 0.5644 | 56.44% |
| CYP inhibitory promiscuity | - | 0.7806 | 78.06% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 1.0000 | 100.00% |
| Carcinogenicity (trinary) | Non-required | 0.7252 | 72.52% |
| Eye corrosion | - | 0.9936 | 99.36% |
| Eye irritation | - | 0.7383 | 73.83% |
| Skin irritation | - | 0.7691 | 76.91% |
| Skin corrosion | - | 0.9606 | 96.06% |
| Ames mutagenesis | + | 0.6365 | 63.65% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5000 | 50.00% |
| Micronuclear | + | 0.6559 | 65.59% |
| Hepatotoxicity | - | 0.7696 | 76.96% |
| skin sensitisation | - | 0.8683 | 86.83% |
| Respiratory toxicity | + | 0.7333 | 73.33% |
| Reproductive toxicity | + | 0.7556 | 75.56% |
| Mitochondrial toxicity | + | 0.6250 | 62.50% |
| Nephrotoxicity | - | 0.7370 | 73.70% |
| Acute Oral Toxicity (c) | IV | 0.3746 | 37.46% |
| Estrogen receptor binding | + | 0.6995 | 69.95% |
| Androgen receptor binding | + | 0.7634 | 76.34% |
| Thyroid receptor binding | - | 0.5000 | 50.00% |
| Glucocorticoid receptor binding | + | 0.7147 | 71.47% |
| Aromatase binding | - | 0.4850 | 48.50% |
| PPAR gamma | + | 0.6676 | 66.76% |
| Honey bee toxicity | - | 0.7498 | 74.98% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | - | 0.6500 | 65.00% |
| Fish aquatic toxicity | + | 0.6921 | 69.21% |
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 | 99.43% | 91.11% |
| CHEMBL2581 | P07339 | Cathepsin D | 96.30% | 98.95% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 94.07% | 89.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 92.37% | 99.15% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 90.04% | 91.49% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 89.22% | 94.00% |
| CHEMBL308 | P06493 | Cyclin-dependent kinase 1 | 88.99% | 91.73% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 88.87% | 94.73% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 88.50% | 95.56% |
| CHEMBL5284 | Q96RR4 | CaM-kinase kinase beta | 87.50% | 89.23% |
| CHEMBL4016 | P42262 | Glutamate receptor ionotropic, AMPA 2 | 86.04% | 86.92% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 84.76% | 86.33% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 82.79% | 97.09% |
| CHEMBL3880 | P07900 | Heat shock protein HSP 90-alpha | 80.61% | 96.21% |
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