Genistein

Details

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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 16,916 references in papers

Physical and Chemical Properties

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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

Synonyms

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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.

2D Structure

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2D Structure of Genistein

3D Structure

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ADMET Properties (via admetSAR 2)

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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%

Targets

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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%

Plants that contains it

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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.
Acacia baileyana
Acacia mearnsii
Acacia mollifolia
Achillea pseudopectinata
Achlys triphylla
Aglaia australiensis
Allagopappus viscosissimus
Amaranthus spinosus
Ammopiptanthus mongolicus
Andira inermis
Apios americana
Arachis hypogaea
Astragalus condensatus
Astragalus multiceps
Astragalus pterocephalus
Astragalus spinosus
Astragalus verrucosus
Atroxima liberica
Atuna excelsa subsp. racemosa
Baptisia bracteata
Baptisia lecontei
Berberis floribunda
Bergenia crassifolia
Bertya dimerostigma
Bolusanthus speciosus
Bonamia spectabilis
Brachypterum scandens
Butea monosperma
Cajanus cajan
Calicotome villosa
Camchaya loloana
Chamaecytisus supinus
Christisonia bicolor
Cicer arietinum
Cistanche salsa
Convallaria majalis
Corynanthe pachyceras
Crotalaria orixensis
Crotalaria pallida
Crotalaria retusa
Crotalaria thebaica
Cullen corylifolium
Cymodocea nodosa
Dalbergia frutescens
Dalbergia odorifera
Dalbergia oliveri
Dalbergia parviflora
Dalbergia sissoo
Deguelia scandens
Delphinium barbeyi
Dendrobium moniliforme
Dermatophyllum secundiflorum
Desmodium uncinatum
Diplacus longiflorus
Echinospartum horridum
Eriosema tuberosum
Erycibe expansa
Erysimum siliculosum
Erythrina burttii
Erythrina fusca
Erythrina variegata
Eschenbachia japonica
Euchresta formosana
Euphrasia stricta
Ficus cordata
Ficus glumosa
Ficus nervosa
Ficus nymphaeifolia
Ficus pumila
Ficus septica
Flemingia macrophylla
Flemingia paniculata
Fumaria densiflora
Garcinia oblongifolia
Genista burdurensis
Genista cadasonensis
Genista ephedroides
Genista morisii
Genista pichisermolliana
Genista sessilifolia
Genista tinctoria
Genista tricuspidata
Ginkgo biloba
Glycine max
Glycine tabacina
Glycyrrhiza glabra
Glycyrrhiza inflata
Glycyrrhiza uralensis
Glycyrrhiza uralensis
Grona styracifolia
Heliotropium hirsutissimum
Hibiscus schizopetalus
Hydrangea serrata
Hylodesmum podocarpum subsp. oxyphyllum
Hyoscyamus pusillus
Hypericum scabrum
Inulanthera calva
Ipomoea muricata
Iris domestica
Iris pseudacorus
Isoberlinia tomentosa
Isodon angustifolius
Jamesoniella colorata
Justicia adhatoda
Kaempferia rotunda
Lablab purpureus
Laburnum anagyroidis
Lawsonia inermis
Lepidosperma ustulatum
Lespedeza cyrtobotrya
Lespedeza floribunda
Licaria brasiliensis
Linum salsoloides
Lunularia cruciata
Lupinus albus
Lupinus angustifolius
Lupinus arboreus
Lupinus luteus
Lupinus polyphyllus
Lupinus pubescens
Lupinus sericeus
Lupinus texensis
Maackia amurensis
Macadamia ternifolia
Maclura cochinchinensis
Maclura tricuspidata
Medicago sativa
Mucuna membranacea
Murraya exotica
Murraya paniculata
Nicotiana raimondii
Ononis spinosa
Oreomecon alpina
Ormosia henryi
Ormosia monosperma
Palafoxia texana
Peltogyne paniculata subsp. pubescens
Pericopsis laxiflora
Petroselinum crispum
Phaseolus coccineus
Phaseolus lunatus
Phaseolus vulgaris
Pinus koraiensis
Piper dilatatum
Piper wightii
Piptanthus nepalensis
Piscidia piscipula
Portulaca oleracea
Prunus avium
Prunus cerasoides
Prunus cerasus
Pterocarpus angolensis
Pterocarpus indicus
Pterodon emarginatus
Pueraria montana var. lobata
Pulsatilla campanella
Punica granatum
Ranunculus peltatus
Rosa chinensis var. spontanea
Rosulabryum capillare
Salvia miltiorrhiza
Sanguisorba officinalis
Saracha nigribaccata
Saussurea japonica
Scolopia chinensis
Scutellaria sieberi
Smilax bracteata
Sophora alopecuroides
Sophora flavescens
Sophora koreensis
Sophora pachycarpa
Sophora tonkinensis
Sorbus cuspidata
Spartium junceum
Spatholobus suberectus
Spirotropis longifolia
Styphnolobium japonicum
Styrax agrestis
Sundacarpus amarus
Syzygium jambos
Syzygium nervosum
Tephrosia sinapou
Teucrium betonicum
Teucrium marum
Thermopsis alterniflora
Thermopsis montana
Thermopsis rhombifolia
Trifolium aureum
Trifolium campestre
Trifolium incarnatum
Trifolium pratense
Trifolium repens
Trifolium resupinatum
Trifolium rubens
Trifolium subterraneum
Trollius europaeus
Tynanthus panurensis
Ulex europaeus
Urceola laevigata
Vepris nobilis
Vigna mungo
Vigna radiata
Vitex negundo
Wisteria brachybotrys
Zea mays

Cross-Links

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PubChem 5280961
NPASS NPC39426
ChEMBL CHEMBL44
LOTUS LTS0106538
wikiData Q415957