Fisetin
| Internal ID | 84e3a0f2-ef81-4e3d-ad02-bc139c82d06a |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavones > Flavonols |
| IUPAC Name | 2-(3,4-dihydroxyphenyl)-3,7-dihydroxychromen-4-one |
| SMILES (Canonical) | C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O |
| SMILES (Isomeric) | C1=CC(=C(C=C1C2=C(C(=O)C3=C(O2)C=C(C=C3)O)O)O)O |
| InChI | InChI=1S/C15H10O6/c16-8-2-3-9-12(6-8)21-15(14(20)13(9)19)7-1-4-10(17)11(18)5-7/h1-6,16-18,20H |
| InChI Key | XHEFDIBZLJXQHF-UHFFFAOYSA-N |
| Popularity | 1,938 references in papers |
| Molecular Formula | C15H10O6 |
| Molecular Weight | 286.24 g/mol |
| Exact Mass | 286.04773803 g/mol |
| Topological Polar Surface Area (TPSA) | 107.00 Ų |
| XlogP | 2.00 |
| Atomic LogP (AlogP) | 2.28 |
| H-Bond Acceptor | 6 |
| H-Bond Donor | 4 |
| Rotatable Bonds | 1 |
| 528-48-3 |
| 5-Desoxyquercetin |
| 2-(3,4-Dihydroxyphenyl)-3,7-dihydroxy-4H-chromen-4-one |
| 3,3',4',7-Tetrahydroxyflavone |
| Cotinin |
| Fustel |
| Viset |
| Fisetholz |
| Superfustel |
| Fietin |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9569 | 95.69% |
| Caco-2 | - | 0.7654 | 76.54% |
| Blood Brain Barrier | - | 0.7750 | 77.50% |
| Human oral bioavailability | + | 0.5143 | 51.43% |
| Subcellular localzation | Mitochondria | 0.7742 | 77.42% |
| OATP2B1 inhibitior | + | 0.5182 | 51.82% |
| OATP1B1 inhibitior | + | 0.9445 | 94.45% |
| OATP1B3 inhibitior | + | 0.9902 | 99.02% |
| MATE1 inhibitior | - | 0.7400 | 74.00% |
| OCT2 inhibitior | - | 0.9500 | 95.00% |
| BSEP inhibitior | - | 0.6866 | 68.66% |
| P-glycoprotein inhibitior | - | 0.9166 | 91.66% |
| P-glycoprotein substrate | - | 0.7702 | 77.02% |
| CYP3A4 substrate | + | 0.5147 | 51.47% |
| CYP2C9 substrate | - | 0.8321 | 83.21% |
| CYP2D6 substrate | - | 0.8118 | 81.18% |
| CYP3A4 inhibition | - | 0.7054 | 70.54% |
| CYP2C9 inhibition | + | 0.8949 | 89.49% |
| CYP2C19 inhibition | - | 0.6965 | 69.65% |
| CYP2D6 inhibition | - | 0.9230 | 92.30% |
| CYP1A2 inhibition | + | 0.9249 | 92.49% |
| CYP2C8 inhibition | + | 0.8877 | 88.77% |
| CYP inhibitory promiscuity | - | 0.5409 | 54.09% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 1.0000 | 100.00% |
| Carcinogenicity (trinary) | Non-required | 0.5926 | 59.26% |
| Eye corrosion | - | 0.9890 | 98.90% |
| Eye irritation | + | 0.9624 | 96.24% |
| Skin irritation | + | 0.6100 | 61.00% |
| Skin corrosion | - | 0.9613 | 96.13% |
| Ames mutagenesis | - | 0.5300 | 53.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.9096 | 90.96% |
| Micronuclear | + | 0.9400 | 94.00% |
| Hepatotoxicity | + | 0.8500 | 85.00% |
| skin sensitisation | - | 0.8006 | 80.06% |
| Respiratory toxicity | + | 0.6667 | 66.67% |
| Reproductive toxicity | + | 0.7667 | 76.67% |
| Mitochondrial toxicity | + | 0.5875 | 58.75% |
| Nephrotoxicity | - | 0.8215 | 82.15% |
| Acute Oral Toxicity (c) | II | 0.7187 | 71.87% |
| Estrogen receptor binding | + | 0.8915 | 89.15% |
| Androgen receptor binding | + | 0.9143 | 91.43% |
| Thyroid receptor binding | + | 0.6157 | 61.57% |
| Glucocorticoid receptor binding | + | 0.8946 | 89.46% |
| Aromatase binding | + | 0.8665 | 86.65% |
| PPAR gamma | + | 0.8700 | 87.00% |
| Honey bee toxicity | - | 0.8661 | 86.61% |
| Biodegradation | - | 0.8000 | 80.00% |
| Crustacea aquatic toxicity | - | 0.5700 | 57.00% |
| Fish aquatic toxicity | + | 0.9311 | 93.11% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
8912.5 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL220 | P22303 | Acetylcholinesterase |
12 nM |
IC50 |
DOI: 10.1007/s00044-012-0353-y
|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
12589.3 nM |
Potency |
via CMAUP
|
| CHEMBL3687 | P18054 | Arachidonate 12-lipoxygenase |
950 nM |
IC50 |
PMID: 17869117
|
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
1400 nM |
IC50 |
PMID: 17869117
|
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
3162.3 nM |
Potency |
via CMAUP
|
| CHEMBL3629 | P68400 | Casein kinase II alpha |
350 nM |
Ki |
via Super-PRED
|
| CHEMBL4801 | P29466 | Caspase-1 |
25118.9 nM 15848.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3468 | P55210 | Caspase-7 |
19952.6 nM 15848.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
19952.6 nM 1995.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL5747 | Q92793 | CREB-binding protein |
25118.9 nM 25118.9 nM 7943.3 nM 10000 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL301 | P24941 | Cyclin-dependent kinase 2 |
5000 nM |
IC50 |
PMID: 17178224
|
| CHEMBL2508 | Q00534 | Cyclin-dependent kinase 6 |
850 nM 850 nM 850 nM |
IC50 IC50 IC50 |
via Super-PRED
PMID: 15689157 DOI: 10.1007/s00044-009-9233-5 |
| CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
19952.6 nM 25118.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
39810.7 nM 25118.9 nM 25118.9 nM 39810.7 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase |
891.3 nM 891.3 nM |
Potency Potency |
via CMAUP
via Super-PRED |
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
2511.9 nM 31622.8 nM 31622.8 nM 1258.9 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL4331 | P68871 | Hemoglobin beta chain |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
14125.4 nM |
Potency |
via CMAUP
|
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
12589.3 nM 7943.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
11220.2 nM 7943.3 nM 5011.9 nM 14125.4 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
| CHEMBL1293235 | P02545 | Prelamin-A/C |
22387.2 nM |
Potency |
via CMAUP
|
| CHEMBL2478 | P04745 | Salivary alpha-amylase |
19600 nM |
IC50 |
PMID: 18507367
|
| CHEMBL2599 | P43405 | Tyrosine-protein kinase SYK |
15000 nM |
IC50 |
PMID: 22257213
|
| CHEMBL1929 | P47989 | Xanthine dehydrogenase |
4330 nM |
IC50 |
PMID: 9461655
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL1951 | P21397 | Monoamine oxidase A | 96.49% | 91.49% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 95.77% | 89.00% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 95.15% | 99.15% |
| CHEMBL2581 | P07339 | Cathepsin D | 92.05% | 98.95% |
| CHEMBL242 | Q92731 | Estrogen receptor beta | 89.80% | 98.35% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 88.59% | 94.00% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 88.58% | 95.56% |
| CHEMBL3194 | P02766 | Transthyretin | 88.54% | 90.71% |
| CHEMBL1163101 | O75460 | Serine/threonine-protein kinase/endoribonuclease IRE1 | 87.40% | 98.11% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 87.38% | 94.45% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 86.18% | 99.23% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 85.25% | 86.33% |
| CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 84.99% | 90.71% |
| CHEMBL2085 | P14174 | Macrophage migration inhibitory factor | 84.97% | 80.78% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 83.34% | 94.73% |
| CHEMBL4940 | P07195 | L-lactate dehydrogenase B chain | 80.72% | 95.53% |
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 | 5281614 |
| NPASS | NPC51443 |
| ChEMBL | CHEMBL31574 |
| LOTUS | LTS0179244 |
| wikiData | Q418384 |