Biochanin A
| Internal ID | 92eae42f-9a36-48c3-824b-405b9a5b2d32 |
| Taxonomy | Phenylpropanoids and polyketides > Isoflavonoids > O-methylated isoflavonoids > 4-O-methylated isoflavonoids > 4-O-methylisoflavones |
| IUPAC Name | 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one |
| SMILES (Canonical) | COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O |
| SMILES (Isomeric) | COC1=CC=C(C=C1)C2=COC3=CC(=CC(=C3C2=O)O)O |
| InChI | InChI=1S/C16H12O5/c1-20-11-4-2-9(3-5-11)12-8-21-14-7-10(17)6-13(18)15(14)16(12)19/h2-8,17-18H,1H3 |
| InChI Key | WUADCCWRTIWANL-UHFFFAOYSA-N |
| Popularity | 1,412 references in papers |
| Molecular Formula | C16H12O5 |
| Molecular Weight | 284.26 g/mol |
| Exact Mass | 284.06847348 g/mol |
| Topological Polar Surface Area (TPSA) | 76.00 Ų |
| XlogP | 3.00 |
| Atomic LogP (AlogP) | 2.88 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 2 |
| 491-80-5 |
| Biochanin |
| 4'-Methylgenistein |
| 5,7-Dihydroxy-4'-methoxyisoflavone |
| 5,7-Dihydroxy-3-(4-methoxyphenyl)-4H-chromen-4-one |
| olmelin |
| Pratensol |
| Biochanine A |
| Genistein 4-methyl ether |
| 5,7-dihydroxy-3-(4-methoxyphenyl)chromen-4-one |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9694 | 96.94% |
| Caco-2 | + | 0.9155 | 91.55% |
| Blood Brain Barrier | - | 0.7750 | 77.50% |
| Human oral bioavailability | - | 0.5143 | 51.43% |
| Subcellular localzation | Mitochondria | 0.7877 | 78.77% |
| OATP2B1 inhibitior | - | 0.5742 | 57.42% |
| OATP1B1 inhibitior | + | 0.9495 | 94.95% |
| OATP1B3 inhibitior | + | 0.9480 | 94.80% |
| MATE1 inhibitior | + | 0.5400 | 54.00% |
| OCT2 inhibitior | - | 0.9250 | 92.50% |
| BSEP inhibitior | - | 0.6813 | 68.13% |
| P-glycoprotein inhibitior | - | 0.8249 | 82.49% |
| P-glycoprotein substrate | - | 0.9379 | 93.79% |
| CYP3A4 substrate | + | 0.5620 | 56.20% |
| CYP2C9 substrate | - | 0.6401 | 64.01% |
| CYP2D6 substrate | - | 0.8296 | 82.96% |
| CYP3A4 inhibition | + | 0.7746 | 77.46% |
| CYP2C9 inhibition | + | 0.8287 | 82.87% |
| CYP2C19 inhibition | + | 0.9470 | 94.70% |
| CYP2D6 inhibition | - | 0.6939 | 69.39% |
| CYP1A2 inhibition | + | 0.9540 | 95.40% |
| CYP2C8 inhibition | + | 0.6803 | 68.03% |
| CYP inhibitory promiscuity | + | 0.8845 | 88.45% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 0.9500 | 95.00% |
| Carcinogenicity (trinary) | Non-required | 0.6169 | 61.69% |
| Eye corrosion | - | 0.9796 | 97.96% |
| Eye irritation | + | 0.8341 | 83.41% |
| Skin irritation | - | 0.6033 | 60.33% |
| Skin corrosion | - | 0.9391 | 93.91% |
| Ames mutagenesis | - | 0.7600 | 76.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.6613 | 66.13% |
| Micronuclear | + | 0.9100 | 91.00% |
| Hepatotoxicity | + | 0.5250 | 52.50% |
| skin sensitisation | - | 0.9484 | 94.84% |
| Respiratory toxicity | - | 0.5444 | 54.44% |
| Reproductive toxicity | + | 0.8000 | 80.00% |
| Mitochondrial toxicity | + | 0.6375 | 63.75% |
| Nephrotoxicity | + | 0.6547 | 65.47% |
| Acute Oral Toxicity (c) | III | 0.7005 | 70.05% |
| Estrogen receptor binding | + | 0.9506 | 95.06% |
| Androgen receptor binding | + | 0.9500 | 95.00% |
| Thyroid receptor binding | + | 0.8461 | 84.61% |
| Glucocorticoid receptor binding | + | 0.8349 | 83.49% |
| Aromatase binding | + | 0.8881 | 88.81% |
| PPAR gamma | + | 0.7143 | 71.43% |
| Honey bee toxicity | - | 0.9188 | 91.88% |
| Biodegradation | - | 0.9750 | 97.50% |
| Crustacea aquatic toxicity | - | 0.5200 | 52.00% |
| Fish aquatic toxicity | + | 0.8717 | 87.17% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
35481.3 nM |
Potency |
via CMAUP
|
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
7079.5 nM |
Potency |
via CMAUP
|
| CHEMBL5983 | O60218 | Aldo-keto reductase family 1 member B10 |
36100 nM |
IC50 |
PMID: 26529431
|
| CHEMBL3687 | P18054 | Arachidonate 12-lipoxygenase |
15848.9 nM |
Potency |
via CMAUP
|
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
1258.9 nM |
Potency |
via CMAUP
|
| CHEMBL3729 | P22748 | Carbonic anhydrase IV |
7078.5 nM |
Ki |
PMID: 26498393
|
| CHEMBL2326 | P43166 | Carbonic anhydrase VII |
371.5 nM 371.5 nM |
Ki Ki |
PMID: 26498393
via Super-PRED |
| CHEMBL3242 | O43570 | Carbonic anhydrase XII |
52.5 nM 52.5 nM |
Ki Ki |
PMID: 26498393
via Super-PRED |
| CHEMBL5586 | P16152 | Carbonyl reductase [NADPH] 1 |
12710 nM |
IC50 |
PMID: 19097799
|
| CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
12589.3 nM 10000 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1978 | P11511 | Cytochrome P450 19A1 |
34000 nM 34000 nM 10.2 nM 113000 nM 113000 nM |
IC50 IC50 IC50 IC50 IC50 |
PMID: 15911319
PMID: 15267241 PMID: 20413308 PMID: 22444875 PMID: 26301554 |
| CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
7943.3 nM |
Potency |
via CMAUP
|
| CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
25.1 nM |
Potency |
via CMAUP
|
| CHEMBL289 | P10635 | Cytochrome P450 2D6 |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
19952.6 nM 19952.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL2789 | P37059 | Estradiol 17-beta-dehydrogenase 2 |
9900 nM |
IC50 |
PMID: 18533708
|
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha |
10000 nM 10000 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
35481.3 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4040 | P28482 | MAP kinase ERK2 |
15848.9 nM |
Potency |
via CMAUP
|
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
2238.7 nM 28183.8 nM 31622.8 nM 10000 nM 2818.4 nM 14125.4 nM 39810.7 nM 17782.8 nM |
Potency Potency Potency Potency Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP |
| CHEMBL1293277 | O15118 | Niemann-Pick C1 protein |
2238.7 nM |
Potency |
via CMAUP
|
| CHEMBL1293235 | P02545 | Prelamin-A/C |
28183.8 nM |
Potency |
via CMAUP
|
| CHEMBL1293294 | P51151 | Ras-related protein Rab-9A |
2818.4 nM |
Potency |
via CMAUP
|
| CHEMBL1293232 | Q16637 | Survival motor neuron protein |
17782.8 nM 19952.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.05% | 91.11% |
| CHEMBL1929 | P47989 | Xanthine dehydrogenase | 97.73% | 96.12% |
| CHEMBL2581 | P07339 | Cathepsin D | 95.63% | 98.95% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 94.60% | 94.00% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 94.44% | 95.56% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 94.41% | 99.15% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 92.28% | 86.33% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 89.90% | 90.00% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 89.38% | 89.00% |
| CHEMBL4016 | P42262 | Glutamate receptor ionotropic, AMPA 2 | 89.06% | 86.92% |
| CHEMBL1907 | P15144 | Aminopeptidase N | 88.45% | 93.31% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 87.94% | 99.17% |
| CHEMBL5409 | Q8TDU6 | G-protein coupled bile acid receptor 1 | 85.40% | 93.65% |
| CHEMBL3194 | P02766 | Transthyretin | 84.58% | 90.71% |
| CHEMBL3192 | Q9BY41 | Histone deacetylase 8 | 84.23% | 93.99% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 82.10% | 96.09% |
| CHEMBL4940 | P07195 | L-lactate dehydrogenase B chain | 81.53% | 95.53% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 81.33% | 99.23% |
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 | 5280373 |
| NPASS | NPC294409 |
| ChEMBL | CHEMBL131921 |
| LOTUS | LTS0111539 |
| wikiData | Q864222 |