Isoquercetin
| Internal ID | 48bd8d33-b70e-491b-bbc9-ff0d2ba8fd9c |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavonoid glycosides > Flavonoid O-glycosides > Flavonoid-3-O-glycosides |
| IUPAC Name | 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one |
| SMILES (Canonical) | C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)OC4C(C(C(C(O4)CO)O)O)O)O)O |
| SMILES (Isomeric) | C1=CC(=C(C=C1C2=C(C(=O)C3=C(C=C(C=C3O2)O)O)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O |
| InChI | InChI=1S/C21H20O12/c22-6-13-15(27)17(29)18(30)21(32-13)33-20-16(28)14-11(26)4-8(23)5-12(14)31-19(20)7-1-2-9(24)10(25)3-7/h1-5,13,15,17-18,21-27,29-30H,6H2/t13-,15-,17+,18-,21+/m1/s1 |
| InChI Key | OVSQVDMCBVZWGM-QSOFNFLRSA-N |
| Popularity | 2,445 references in papers |
| Molecular Formula | C21H20O12 |
| Molecular Weight | 464.40 g/mol |
| Exact Mass | 464.09547607 g/mol |
| Topological Polar Surface Area (TPSA) | 207.00 Ų |
| XlogP | 0.40 |
| Atomic LogP (AlogP) | -0.54 |
| H-Bond Acceptor | 12 |
| H-Bond Donor | 8 |
| Rotatable Bonds | 4 |
| Isoquercetin |
| 482-35-9 |
| Hirsutrin |
| 3-Glucosylquercetin |
| Quercetin 3-glucoside |
| Quercetin 3-o-glucopyranoside |
| Quercetin 3-D-glucoside |
| Quercetol 3-monoglucoside |
| Quercetin 3-O-glucoside |
| Quercetol 3-glucoside |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | - | 0.5116 | 51.16% |
| Caco-2 | - | 0.9010 | 90.10% |
| Blood Brain Barrier | - | 0.7750 | 77.50% |
| Human oral bioavailability | - | 0.7286 | 72.86% |
| Subcellular localzation | Mitochondria | 0.6068 | 60.68% |
| OATP2B1 inhibitior | + | 0.5930 | 59.30% |
| OATP1B1 inhibitior | + | 0.9271 | 92.71% |
| OATP1B3 inhibitior | + | 0.9265 | 92.65% |
| MATE1 inhibitior | - | 0.7800 | 78.00% |
| OCT2 inhibitior | - | 0.7750 | 77.50% |
| BSEP inhibitior | - | 0.6488 | 64.88% |
| P-glycoprotein inhibitior | - | 0.6240 | 62.40% |
| P-glycoprotein substrate | - | 0.8086 | 80.86% |
| CYP3A4 substrate | + | 0.6155 | 61.55% |
| CYP2C9 substrate | - | 0.6709 | 67.09% |
| CYP2D6 substrate | - | 0.8582 | 85.82% |
| 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 | + | 0.8882 | 88.82% |
| 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 | - | 0.7321 | 73.21% |
| Skin irritation | - | 0.8036 | 80.36% |
| Skin corrosion | - | 0.9691 | 96.91% |
| Ames mutagenesis | + | 0.7200 | 72.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5000 | 50.00% |
| Micronuclear | + | 0.6533 | 65.33% |
| Hepatotoxicity | - | 0.5196 | 51.96% |
| skin sensitisation | - | 0.9122 | 91.22% |
| Respiratory toxicity | + | 0.6222 | 62.22% |
| Reproductive toxicity | + | 0.7222 | 72.22% |
| Mitochondrial toxicity | + | 0.5125 | 51.25% |
| Nephrotoxicity | - | 0.7975 | 79.75% |
| Acute Oral Toxicity (c) | III | 0.4045 | 40.45% |
| Estrogen receptor binding | + | 0.7470 | 74.70% |
| Androgen receptor binding | + | 0.7633 | 76.33% |
| Thyroid receptor binding | - | 0.5202 | 52.02% |
| Glucocorticoid receptor binding | + | 0.7040 | 70.40% |
| Aromatase binding | + | 0.5913 | 59.13% |
| PPAR gamma | + | 0.7022 | 70.22% |
| Honey bee toxicity | - | 0.7417 | 74.17% |
| Biodegradation | - | 0.7000 | 70.00% |
| Crustacea aquatic toxicity | - | 0.6250 | 62.50% |
| Fish aquatic toxicity | + | 0.8218 | 82.18% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1900 | P15121 | Aldose reductase |
4500 nM |
IC50 |
PMID: 22261024
|
| CHEMBL5979 | P05186 | Alkaline phosphatase, tissue-nonspecific isozyme |
14000 nM |
IC50 |
via CMAUP
|
| CHEMBL205 | P00918 | Carbonic anhydrase II |
410 nM 6211.2 nM 410 nM |
Ki Ki Ki |
via Super-PRED
PMID: 26498393 PMID: 26498393 |
| CHEMBL3729 | P22748 | Carbonic anhydrase IV |
75.7 nM 75.7 nM |
Ki Ki |
via Super-PRED
PMID: 26498393 |
| CHEMBL2326 | P43166 | Carbonic anhydrase VII |
3.8 nM 3.8 nM |
Ki Ki |
PMID: 26498393
via Super-PRED |
| CHEMBL3242 | O43570 | Carbonic anhydrase XII |
170 nM 52.1 nM 52.1 nM |
Ki Ki Ki |
PMID: 26498393
PMID: 26498393 via Super-PRED |
| CHEMBL2392 | P06746 | DNA polymerase beta |
1778.3 nM |
Potency |
via CMAUP
|
| CHEMBL2409 | P34913 | Epoxide hydratase |
28430 nM |
IC50 |
PMID: 24679441
|
| CHEMBL5573 | P09923 | Intestinal alkaline phosphatase |
8960 nM 5250 nM |
IC50 IC50 |
via CMAUP
via CMAUP |
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
12589.3 nM |
Potency |
via CMAUP
|
| CHEMBL6136 | O60341 | Lysine-specific histone demethylase 1 |
950 nM |
IC50 |
via Super-PRED
|
| CHEMBL2608 | P10253 | Lysosomal alpha-glucosidase |
3548.1 nM |
Potency |
via CMAUP
|
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
15848.9 nM |
Potency |
via CMAUP
|
| CHEMBL1293232 | Q16637 | Survival motor neuron protein |
446.7 nM |
Potency |
via Super-PRED
|
| CHEMBL1929 | P47989 | Xanthine dehydrogenase |
26310 nM |
IC50 |
PMID: 12444671
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 99.54% | 91.11% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 96.43% | 89.00% |
| CHEMBL2581 | P07339 | Cathepsin D | 95.28% | 98.95% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 92.96% | 99.15% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 92.68% | 91.49% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 91.26% | 94.00% |
| CHEMBL2345 | P51812 | Ribosomal protein S6 kinase alpha 3 | 90.17% | 95.64% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 89.84% | 94.73% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 89.58% | 99.17% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 89.11% | 86.33% |
| CHEMBL3194 | P02766 | Transthyretin | 88.77% | 90.71% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 86.32% | 94.45% |
| CHEMBL4016 | P42262 | Glutamate receptor ionotropic, AMPA 2 | 85.77% | 86.92% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 85.50% | 96.09% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 84.84% | 95.56% |
| CHEMBL5339 | Q5NUL3 | G-protein coupled receptor 120 | 84.25% | 95.78% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 82.96% | 97.09% |
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.
To see more specific details click the taxa you are interested in.
| PubChem | 5280804 |
| NPASS | NPC179950 |
| ChEMBL | CHEMBL250450 |
| LOTUS | LTS0254337 |
| wikiData | Q6086296 |