7-(alpha-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one
| Internal ID | c3691a82-ef36-4b77-8763-110f53a33ab0 |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-7-O-glycosides |
| IUPAC Name | 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one |
| SMILES (Canonical) | C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)OC4C(C(C(C(O4)CO)O)O)O)O)O |
| SMILES (Isomeric) | C1=CC(=CC=C1C2=CC(=O)C3=C(C=C(C=C3O2)O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O |
| InChI | InChI=1S/C21H20O10/c22-8-16-18(26)19(27)20(28)21(31-16)29-11-5-12(24)17-13(25)7-14(30-15(17)6-11)9-1-3-10(23)4-2-9/h1-7,16,18-24,26-28H,8H2/t16-,18-,19+,20-,21+/m1/s1 |
| InChI Key | KMOUJOKENFFTPU-RQXATKFSSA-N |
| Popularity | 322 references in papers |
| Molecular Formula | C21H20O10 |
| Molecular Weight | 432.40 g/mol |
| Exact Mass | 432.10564683 g/mol |
| Topological Polar Surface Area (TPSA) | 166.00 Ų |
| XlogP | -0.10 |
| Atomic LogP (AlogP) | 0.05 |
| H-Bond Acceptor | 10 |
| H-Bond Donor | 6 |
| Rotatable Bonds | 4 |
| 7-(alpha-D-Glucopyranosyloxy)-5-hydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one |
| EINECS 303-212-4 |
| Apigenin-7-O-glucoside |
| DTXSID20240865 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | - | 0.5548 | 55.48% |
| Caco-2 | - | 0.9236 | 92.36% |
| Blood Brain Barrier | - | 0.7000 | 70.00% |
| Human oral bioavailability | - | 0.8286 | 82.86% |
| Subcellular localzation | Mitochondria | 0.6433 | 64.33% |
| OATP2B1 inhibitior | - | 0.5298 | 52.98% |
| OATP1B1 inhibitior | + | 0.9514 | 95.14% |
| OATP1B3 inhibitior | + | 0.9480 | 94.80% |
| MATE1 inhibitior | - | 0.8400 | 84.00% |
| OCT2 inhibitior | - | 0.8500 | 85.00% |
| BSEP inhibitior | - | 0.4704 | 47.04% |
| P-glycoprotein inhibitior | - | 0.8532 | 85.32% |
| P-glycoprotein substrate | - | 0.8587 | 85.87% |
| CYP3A4 substrate | + | 0.5537 | 55.37% |
| CYP2C9 substrate | - | 0.6762 | 67.62% |
| CYP2D6 substrate | - | 0.8575 | 85.75% |
| CYP3A4 inhibition | - | 0.9192 | 91.92% |
| CYP2C9 inhibition | - | 0.9435 | 94.35% |
| CYP2C19 inhibition | - | 0.9426 | 94.26% |
| CYP2D6 inhibition | - | 0.9501 | 95.01% |
| CYP1A2 inhibition | - | 0.9203 | 92.03% |
| CYP2C8 inhibition | + | 0.6928 | 69.28% |
| CYP inhibitory promiscuity | - | 0.7833 | 78.33% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 1.0000 | 100.00% |
| Carcinogenicity (trinary) | Non-required | 0.6688 | 66.88% |
| Eye corrosion | - | 0.9926 | 99.26% |
| Eye irritation | - | 0.8716 | 87.16% |
| Skin irritation | - | 0.8111 | 81.11% |
| Skin corrosion | - | 0.9715 | 97.15% |
| Ames mutagenesis | + | 0.5200 | 52.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5745 | 57.45% |
| Micronuclear | + | 0.6133 | 61.33% |
| Hepatotoxicity | - | 0.8696 | 86.96% |
| skin sensitisation | - | 0.9256 | 92.56% |
| Respiratory toxicity | - | 0.5111 | 51.11% |
| Reproductive toxicity | + | 0.6667 | 66.67% |
| Mitochondrial toxicity | - | 0.5125 | 51.25% |
| Nephrotoxicity | - | 0.7945 | 79.45% |
| Acute Oral Toxicity (c) | III | 0.4522 | 45.22% |
| Estrogen receptor binding | + | 0.6847 | 68.47% |
| Androgen receptor binding | + | 0.7434 | 74.34% |
| Thyroid receptor binding | + | 0.5224 | 52.24% |
| Glucocorticoid receptor binding | + | 0.5840 | 58.40% |
| Aromatase binding | + | 0.6524 | 65.24% |
| PPAR gamma | + | 0.8225 | 82.25% |
| Honey bee toxicity | - | 0.6936 | 69.36% |
| Biodegradation | - | 0.8500 | 85.00% |
| Crustacea aquatic toxicity | - | 0.6450 | 64.50% |
| Fish aquatic toxicity | + | 0.7773 | 77.73% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1825 | P01375 | TNF-alpha |
200 nM |
Kd |
via Super-PRED
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 99.32% | 91.11% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 95.74% | 94.00% |
| CHEMBL2581 | P07339 | Cathepsin D | 95.39% | 98.95% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 94.51% | 89.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 93.74% | 99.15% |
| CHEMBL4016 | P42262 | Glutamate receptor ionotropic, AMPA 2 | 91.90% | 86.92% |
| CHEMBL3194 | P02766 | Transthyretin | 91.80% | 90.71% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 89.31% | 91.49% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 88.73% | 97.09% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 88.56% | 94.73% |
| CHEMBL242 | Q92731 | Estrogen receptor beta | 87.75% | 98.35% |
| CHEMBL5339 | Q5NUL3 | G-protein coupled receptor 120 | 87.54% | 95.78% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 86.44% | 94.45% |
| CHEMBL3880 | P07900 | Heat shock protein HSP 90-alpha | 86.10% | 96.21% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 85.28% | 86.33% |
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] | 84.61% | 83.57% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 83.41% | 95.56% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 82.50% | 95.89% |
| CHEMBL2288 | Q13526 | Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | 82.44% | 91.71% |
| CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 81.74% | 90.71% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 81.42% | 99.17% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 81.32% | 85.14% |
| CHEMBL1907603 | Q05586 | Glutamate NMDA receptor; GRIN1/GRIN2B | 80.77% | 95.89% |
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.
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| PubChem | 12304095 |
| NPASS | NPC256006 |
| LOTUS | LTS0164885 |
| wikiData | Q83123988 |