Genistein
Internal ID | 6d2d8b1b-b7af-490b-9c4b-16817e8737d5 |
Taxonomy | Phenylpropanoids and polyketides > Isoflavonoids > Isoflav-2-enes > Isoflavones |
IUPAC Name | 5,7-dihydroxy-3-(4-hydroxyphenyl)chromen-4-one |
SMILES (Canonical) | C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O |
SMILES (Isomeric) | C1=CC(=CC=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O |
InChI | InChI=1S/C15H10O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-7,16-18H |
InChI Key | TZBJGXHYKVUXJN-UHFFFAOYSA-N |
Popularity | 17,768 references in papers |
Molecular Formula | C15H10O5 |
Molecular Weight | 270.24 g/mol |
Exact Mass | 270.05282342 g/mol |
Topological Polar Surface Area (TPSA) | 87.00 Ų |
XlogP | 2.70 |
Atomic LogP (AlogP) | 2.58 |
H-Bond Acceptor | 5 |
H-Bond Donor | 3 |
Rotatable Bonds | 1 |
446-72-0 |
Prunetol |
4',5,7-Trihydroxyisoflavone |
Genisterin |
Genisteol |
Sophoricol |
5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one |
5,7,4'-Trihydroxyisoflavone |
Bonistein |
Genestein |
There are more than 10 synonyms. If you wish to see them all click here. |

Target | Value | Probability (raw) | Probability (%) |
---|---|---|---|
Human Intestinal Absorption | + | 0.9677 | 96.77% |
Caco-2 | + | 0.9525 | 95.25% |
Blood Brain Barrier | - | 0.8000 | 80.00% |
Human oral bioavailability | - | 0.6000 | 60.00% |
Subcellular localzation | Mitochondria | 0.7606 | 76.06% |
OATP2B1 inhibitior | + | 0.5567 | 55.67% |
OATP1B1 inhibitior | + | 0.9414 | 94.14% |
OATP1B3 inhibitior | - | 0.5698 | 56.98% |
MATE1 inhibitior | + | 0.6600 | 66.00% |
OCT2 inhibitior | - | 0.9750 | 97.50% |
BSEP inhibitior | - | 0.6782 | 67.82% |
P-glycoprotein inhibitior | - | 0.9165 | 91.65% |
P-glycoprotein substrate | - | 0.9446 | 94.46% |
CYP3A4 substrate | - | 0.5176 | 51.76% |
CYP2C9 substrate | - | 0.6443 | 64.43% |
CYP2D6 substrate | - | 0.8503 | 85.03% |
CYP3A4 inhibition | + | 0.7960 | 79.60% |
CYP2C9 inhibition | + | 0.8949 | 89.49% |
CYP2C19 inhibition | + | 0.8881 | 88.81% |
CYP2D6 inhibition | - | 0.9232 | 92.32% |
CYP1A2 inhibition | + | 0.9254 | 92.54% |
CYP2C8 inhibition | + | 0.7161 | 71.61% |
CYP inhibitory promiscuity | + | 0.8009 | 80.09% |
UGT catelyzed | + | 0.8000 | 80.00% |
Carcinogenicity (binary) | - | 0.9700 | 97.00% |
Carcinogenicity (trinary) | Non-required | 0.7003 | 70.03% |
Eye corrosion | - | 0.9917 | 99.17% |
Eye irritation | + | 0.9759 | 97.59% |
Skin irritation | + | 0.6236 | 62.36% |
Skin corrosion | - | 0.9718 | 97.18% |
Ames mutagenesis | - | 0.6300 | 63.00% |
Human Ether-a-go-go-Related Gene inhibition | - | 0.8575 | 85.75% |
Micronuclear | + | 0.9500 | 95.00% |
Hepatotoxicity | + | 0.6179 | 61.79% |
skin sensitisation | - | 0.8396 | 83.96% |
Respiratory toxicity | - | 0.5000 | 50.00% |
Reproductive toxicity | + | 0.7556 | 75.56% |
Mitochondrial toxicity | + | 0.5250 | 52.50% |
Nephrotoxicity | + | 0.6869 | 68.69% |
Acute Oral Toxicity (c) | II | 0.5830 | 58.30% |
Estrogen receptor binding | + | 0.8920 | 89.20% |
Androgen receptor binding | + | 0.9456 | 94.56% |
Thyroid receptor binding | + | 0.8257 | 82.57% |
Glucocorticoid receptor binding | + | 0.9275 | 92.75% |
Aromatase binding | + | 0.8685 | 86.85% |
PPAR gamma | + | 0.8951 | 89.51% |
Honey bee toxicity | - | 0.9091 | 90.91% |
Biodegradation | - | 0.9250 | 92.50% |
Crustacea aquatic toxicity | - | 0.5400 | 54.00% |
Fish aquatic toxicity | + | 0.9214 | 92.14% |
Proven Targets:
CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
---|---|---|---|---|---|
CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
11220.2 nM 19952.6 nM 19952.6 nM 25118.9 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
CHEMBL226 | P30542 | Adenosine A1 receptor |
19904 nM |
IC50 |
via CMAUP
|
CHEMBL251 | P29274 | Adenosine A2a receptor |
17442 nM |
IC50 |
via CMAUP
|
CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
39810.7 nM 35481.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL3257 | Q06278 | Aldehyde oxidase |
340 nM |
IC50 |
PMID: 20853847
|
CHEMBL1900 | P15121 | Aldose reductase |
20000 nM |
IC50 |
PMID: 22261024
|
CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
31622.8 nM 19952.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL5393 | Q9UNQ0 | ATP-binding cassette sub-family G member 2 |
6900 nM 8800 nM |
IC50 IC50 |
PMID: 21354800
PMID: 21354800 |
CHEMBL1293237 | P54132 | Bloom syndrome protein |
0.2 nM 0.2 nM 0.2 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via Super-PRED |
CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
10000 nM 10000 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL3356 | P05177 | Cytochrome P450 1A2 |
5011.87 nM |
AC50 |
via CMAUP
|
CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
10000 nM 19952.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
1000 nM |
Potency |
via CMAUP
|
CHEMBL340 | P08684 | Cytochrome P450 3A4 |
7943.3 nM 12589.3 nM 7943.3 nM 12589.3 nM |
Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP |
CHEMBL284 | P27487 | Dipeptidyl peptidase IV |
480 nM |
IC50 |
via Super-PRED
|
CHEMBL1993 | P26358 | DNA (cytosine-5)-methyltransferase 1 |
30000 nM |
IC50 |
PMID: 25406944
|
CHEMBL238 | Q01959 | Dopamine transporter |
16918 nM |
IC50 |
via CMAUP
|
CHEMBL203 | P00533 | Epidermal growth factor receptor erbB1 |
1000 nM 1000 nM 1000 nM |
IC50 IC50 IC50 |
PMID: 7608909
PMID: 8151612 PMID: 10090785 |
CHEMBL3181 | P14061 | Estradiol 17-beta-dehydrogenase 1 |
2210 nM |
IC50 |
PMID: 18533708
|
CHEMBL2789 | P37059 | Estradiol 17-beta-dehydrogenase 2 |
16500 nM |
IC50 |
PMID: 18533708
|
CHEMBL206 | P03372 | Estrogen receptor alpha |
1300 nM 300 nM 395 nM 92 nM 395 nM 395 nM 395 nM 395 nM 29.4 nM 9.7 nM 1145 nM 395 nM 580 nM 135 nM 9.7 nM |
IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 |
PMID: 11459643
PMID: 12502307 PMID: 12824043 PMID: 15006374 PMID: 15341953 PMID: 15456246 PMID: 15943471 PMID: 16098741 PMID: 16219463 PMID: 17049855 PMID: 17149865 PMID: 17188490 PMID: 17574424 via CMAUP via Super-PRED |
CHEMBL242 | Q92731 | Estrogen receptor beta |
18 nM 10 nM 4 nM 10 nM 10 nM 9.7 nM 10 nM 1.3 nM 25 nM 9.7 nM 6.8 nM 2.88 nM |
IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 IC50 |
PMID: 12502307
PMID: 12824043 PMID: 15006374 PMID: 15341953 PMID: 15456246 PMID: 15943471 PMID: 16098741 PMID: 16219463 PMID: 17149865 PMID: 17188490 PMID: 17574424 via CMAUP |
CHEMBL3429 | P11474 | Estrogen-related receptor alpha |
10 nM 10 nM |
IC50 IC50 |
PMID: 17482813
via Super-PRED |
CHEMBL3751 | O95718 | Estrogen-related receptor beta |
395 nM 395 nM |
IC50 IC50 |
PMID: 17482813
via Super-PRED |
CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha |
5011.9 nM 5011.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL2808 | Q13133 | LXR-alpha |
31000 nM |
IC50 |
PMID: 18343126
|
CHEMBL4093 | P55055 | LXR-beta |
22000 nM |
IC50 |
PMID: 18343126
|
CHEMBL2074 | O43451 | Maltase-glucoamylase |
10400 nM 2610 nM |
IC50 IC50 |
PMID: 15125965
PMID: 15125965 |
CHEMBL4040 | P28482 | MAP kinase ERK2 |
1995.3 nM 3162.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
446.7 nM 501.2 nM 15848.9 nM 22387.2 nM 11220.2 nM 15848.9 nM 501.2 nM |
Potency Potency Potency Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via Super-PRED |
CHEMBL1951 | P21397 | Monoamine oxidase A |
2520 nM |
IC50 |
via CMAUP
|
CHEMBL1293277 | O15118 | Niemann-Pick C1 protein |
4466.8 nM 5804.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL1869 | P11926 | Ornithine decarboxylase |
26000 nM |
IC50 |
PMID: 10075742
|
CHEMBL1293298 | Q01453 | Peripheral myelin protein 22 |
16944.1 nM |
Potency |
via CMAUP
|
CHEMBL1293235 | P02545 | Prelamin-A/C |
15848.9 nM 15848.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL1075189 | P14618 | Pyruvate kinase isozymes M1/M2 |
25118.9 nM 25118.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL1293294 | P51151 | Ras-related protein Rab-9A |
12589.3 nM 3981.1 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL224 | P28223 | Serotonin 2a (5-HT2a) receptor |
10469 nM |
IC50 |
via CMAUP
|
CHEMBL225 | P28335 | Serotonin 2c (5-HT2c) receptor |
14910 nM |
IC50 |
via CMAUP
|
CHEMBL1697668 | Q9Y6L6 | Solute carrier organic anion transporter family member 1B1 |
9120.11 nM |
IC50 |
PMID: 23571415
|
CHEMBL1743121 | Q9NPD5 | Solute carrier organic anion transporter family member 1B3 |
3890.45 nM |
IC50 |
PMID: 23571415
|
CHEMBL1293232 | Q16637 | Survival motor neuron protein |
28183.8 nM 22387.2 nM 25118.9 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
CHEMBL1293256 | P40225 | Thrombopoietin |
1584.9 nM 1584.9 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL1835 | P24557 | Thromboxane-A synthase |
7720 nM |
IC50 |
via CMAUP
|
CHEMBL1963 | P16473 | Thyroid stimulating hormone receptor |
1000 nM 1000 nM |
Potency Potency |
via CMAUP
via CMAUP |
CHEMBL1862 | P00519 | Tyrosine-protein kinase ABL |
10000 nM |
IC50 |
PMID: 7608909
|
CHEMBL2599 | P43405 | Tyrosine-protein kinase SYK |
39000 nM |
IC50 |
PMID: 19254842
|
CHEMBL1075138 | Q9NUW8 | Tyrosyl-DNA phosphodiesterase 1 |
8912.5 nM |
Potency |
via CMAUP
|
Predicted Targets (via Super-PRED):
CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
---|---|---|---|---|
CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 96.78% | 91.11% |
CHEMBL2581 | P07339 | Cathepsin D | 95.31% | 98.95% |
CHEMBL242 | Q92731 | Estrogen receptor beta | 95.14% | 98.35% |
CHEMBL1929 | P47989 | Xanthine dehydrogenase | 95.06% | 96.12% |
CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 94.01% | 89.00% |
CHEMBL3194 | P02766 | Transthyretin | 91.31% | 90.71% |
CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 88.16% | 99.15% |
CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 87.81% | 95.56% |
CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 87.71% | 86.33% |
CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 86.71% | 94.00% |
CHEMBL2345 | P51812 | Ribosomal protein S6 kinase alpha 3 | 85.99% | 95.64% |
CHEMBL3038469 | P24941 | CDK2/Cyclin A | 83.32% | 91.38% |
CHEMBL5845 | P23415 | Glycine receptor subunit alpha-1 | 82.81% | 90.71% |
CHEMBL1937 | Q92769 | Histone deacetylase 2 | 81.52% | 94.75% |
CHEMBL2288 | Q13526 | Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 | 81.30% | 91.71% |
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