5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
| Internal ID | 2b7586a3-96a2-4c07-9f66-86deb9c0044f |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides |
| IUPAC Name | 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one |
| SMILES (Canonical) | C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O |
| SMILES (Isomeric) | C1=CC(=CC=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4C(C([C@H]([C@H](O4)CO)O)O)O)O |
| InChI | InChI=1S/C21H20O11/c22-7-13-15(26)17(28)18(29)21(31-13)32-20-16(27)14-11(25)5-10(24)6-12(14)30-19(20)8-1-3-9(23)4-2-8/h1-6,13,15,17-18,21-26,28-29H,7H2/t13-,15+,17?,18?,21+/m1/s1 |
| InChI Key | JPUKWEQWGBDDQB-WVTKYERHSA-N |
| Popularity | 14 references in papers |
| Molecular Formula | C21H20O11 |
| Molecular Weight | 448.40 g/mol |
| Exact Mass | 448.10056145 g/mol |
| Topological Polar Surface Area (TPSA) | 186.00 Ų |
| XlogP | 0.70 |
| Atomic LogP (AlogP) | -0.24 |
| H-Bond Acceptor | 11 |
| H-Bond Donor | 7 |
| Rotatable Bonds | 4 |
| There are no found synonyms. |
![2D Structure of 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one](https://plantaedb.com/storage/docs/compounds/2023/07/e7776ab0-2384-11ee-aa6f-0f69b05210e2.jpg "2D Structure of 5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | - | 0.5116 | 51.16% |
| Caco-2 | - | 0.9102 | 91.02% |
| Blood Brain Barrier | - | 0.7750 | 77.50% |
| Human oral bioavailability | - | 0.7714 | 77.14% |
| Subcellular localzation | Mitochondria | 0.6068 | 60.68% |
| OATP2B1 inhibitior | + | 0.5869 | 58.69% |
| OATP1B1 inhibitior | + | 0.8875 | 88.75% |
| OATP1B3 inhibitior | + | 0.9265 | 92.65% |
| MATE1 inhibitior | - | 0.8400 | 84.00% |
| OCT2 inhibitior | - | 0.7750 | 77.50% |
| BSEP inhibitior | - | 0.5444 | 54.44% |
| P-glycoprotein inhibitior | - | 0.6120 | 61.20% |
| P-glycoprotein substrate | - | 0.7828 | 78.28% |
| CYP3A4 substrate | + | 0.6012 | 60.12% |
| CYP2C9 substrate | - | 0.6762 | 67.62% |
| CYP2D6 substrate | - | 0.8575 | 85.75% |
| CYP3A4 inhibition | - | 0.9193 | 91.93% |
| CYP2C9 inhibition | - | 0.9296 | 92.96% |
| CYP2C19 inhibition | - | 0.9289 | 92.89% |
| CYP2D6 inhibition | - | 0.9513 | 95.13% |
| CYP1A2 inhibition | - | 0.9084 | 90.84% |
| CYP2C8 inhibition | + | 0.8532 | 85.32% |
| CYP inhibitory promiscuity | - | 0.7728 | 77.28% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 1.0000 | 100.00% |
| Carcinogenicity (trinary) | Non-required | 0.7144 | 71.44% |
| Eye corrosion | - | 0.9930 | 99.30% |
| Eye irritation | - | 0.7324 | 73.24% |
| Skin irritation | - | 0.8036 | 80.36% |
| Skin corrosion | - | 0.9691 | 96.91% |
| Ames mutagenesis | + | 0.7000 | 70.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5892 | 58.92% |
| Micronuclear | + | 0.6533 | 65.33% |
| Hepatotoxicity | - | 0.6071 | 60.71% |
| skin sensitisation | - | 0.9122 | 91.22% |
| Respiratory toxicity | + | 0.5667 | 56.67% |
| Reproductive toxicity | + | 0.7222 | 72.22% |
| Mitochondrial toxicity | + | 0.5125 | 51.25% |
| Nephrotoxicity | - | 0.7272 | 72.72% |
| Acute Oral Toxicity (c) | III | 0.4045 | 40.45% |
| Estrogen receptor binding | + | 0.7820 | 78.20% |
| Androgen receptor binding | + | 0.7749 | 77.49% |
| Thyroid receptor binding | - | 0.5057 | 50.57% |
| Glucocorticoid receptor binding | + | 0.7121 | 71.21% |
| Aromatase binding | + | 0.6263 | 62.63% |
| PPAR gamma | + | 0.7114 | 71.14% |
| Honey bee toxicity | - | 0.7722 | 77.22% |
| Biodegradation | - | 0.6750 | 67.50% |
| Crustacea aquatic toxicity | - | 0.6350 | 63.50% |
| Fish aquatic toxicity | + | 0.8218 | 82.18% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL220 | P22303 | Acetylcholinesterase |
12 nM |
IC50 |
via Super-PRED
|
| CHEMBL205 | P00918 | Carbonic anhydrase II |
168 nM |
Ki |
via Super-PRED
|
| CHEMBL2326 | P43166 | Carbonic anhydrase VII |
423.7 nM |
Ki |
via Super-PRED
|
| CHEMBL3242 | O43570 | Carbonic anhydrase XII |
4.9 nM |
Ki |
via Super-PRED
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 99.21% | 91.11% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 96.19% | 89.00% |
| CHEMBL2581 | P07339 | Cathepsin D | 95.98% | 98.95% |
| CHEMBL2345 | P51812 | Ribosomal protein S6 kinase alpha 3 | 95.81% | 95.64% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 93.62% | 94.00% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 89.84% | 94.73% |
| CHEMBL3194 | P02766 | Transthyretin | 89.10% | 90.71% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 88.84% | 99.17% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 88.33% | 99.15% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 87.75% | 86.33% |
| CHEMBL4016 | P42262 | Glutamate receptor ionotropic, AMPA 2 | 87.13% | 86.92% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 86.56% | 94.45% |
| CHEMBL5339 | Q5NUL3 | G-protein coupled receptor 120 | 85.93% | 95.78% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 84.78% | 96.09% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 84.46% | 95.56% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 81.71% | 97.09% |
| CHEMBL242 | Q92731 | Estrogen receptor beta | 81.06% | 98.35% |
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