Baicalein
| Internal ID | ed2c5ef7-f10a-4ed1-a08f-75f57572562e |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavones |
| IUPAC Name | 5,6,7-trihydroxy-2-phenylchromen-4-one |
| SMILES (Canonical) | C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O |
| SMILES (Isomeric) | C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O |
| InChI | InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H |
| InChI Key | FXNFHKRTJBSTCS-UHFFFAOYSA-N |
| Popularity | 3,305 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 | 1.70 |
| Atomic LogP (AlogP) | 2.58 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 1 |
| 491-67-8 |
| 5,6,7-Trihydroxyflavone |
| Noroxylin |
| 5,6,7-trihydroxy-2-phenyl-4H-chromen-4-one |
| Biacalein |
| BaiKalein |
| 5,6,7-trihydroxy-2-phenylchromen-4-one |
| Baicelein |
| 5,6,7-trihydroxy-2-phenyl-chromen-4-one |
| MFCD00017459 |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9071 | 90.71% |
| Caco-2 | - | 0.9372 | 93.72% |
| Blood Brain Barrier | - | 0.7750 | 77.50% |
| Human oral bioavailability | + | 0.6714 | 67.14% |
| Subcellular localzation | Mitochondria | 0.5892 | 58.92% |
| OATP2B1 inhibitior | - | 0.5665 | 56.65% |
| OATP1B1 inhibitior | + | 0.9505 | 95.05% |
| OATP1B3 inhibitior | + | 0.9480 | 94.80% |
| MATE1 inhibitior | + | 0.6600 | 66.00% |
| OCT2 inhibitior | - | 0.9750 | 97.50% |
| BSEP inhibitior | - | 0.8558 | 85.58% |
| P-glycoprotein inhibitior | - | 0.7133 | 71.33% |
| P-glycoprotein substrate | - | 0.9700 | 97.00% |
| CYP3A4 substrate | - | 0.5997 | 59.97% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8553 | 85.53% |
| CYP3A4 inhibition | + | 0.6951 | 69.51% |
| CYP2C9 inhibition | - | 0.5823 | 58.23% |
| CYP2C19 inhibition | - | 0.9025 | 90.25% |
| CYP2D6 inhibition | - | 0.9287 | 92.87% |
| CYP1A2 inhibition | + | 0.9106 | 91.06% |
| CYP2C8 inhibition | + | 0.5678 | 56.78% |
| CYP inhibitory promiscuity | + | 0.5822 | 58.22% |
| UGT catelyzed | + | 0.8000 | 80.00% |
| Carcinogenicity (binary) | - | 1.0000 | 100.00% |
| Carcinogenicity (trinary) | Non-required | 0.6750 | 67.50% |
| Eye corrosion | - | 0.9905 | 99.05% |
| Eye irritation | + | 0.9628 | 96.28% |
| Skin irritation | + | 0.5835 | 58.35% |
| Skin corrosion | - | 0.9397 | 93.97% |
| Ames mutagenesis | - | 0.6300 | 63.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.8465 | 84.65% |
| Micronuclear | + | 0.9300 | 93.00% |
| Hepatotoxicity | - | 0.6000 | 60.00% |
| skin sensitisation | - | 0.7447 | 74.47% |
| Respiratory toxicity | + | 0.6000 | 60.00% |
| Reproductive toxicity | + | 0.7667 | 76.67% |
| Mitochondrial toxicity | + | 0.5875 | 58.75% |
| Nephrotoxicity | - | 0.8449 | 84.49% |
| Acute Oral Toxicity (c) | II | 0.7348 | 73.48% |
| Estrogen receptor binding | + | 0.9162 | 91.62% |
| Androgen receptor binding | + | 0.8992 | 89.92% |
| Thyroid receptor binding | + | 0.6775 | 67.75% |
| Glucocorticoid receptor binding | + | 0.9336 | 93.36% |
| Aromatase binding | + | 0.8824 | 88.24% |
| PPAR gamma | + | 0.9086 | 90.86% |
| Honey bee toxicity | - | 0.8822 | 88.22% |
| Biodegradation | - | 0.9000 | 90.00% |
| Crustacea aquatic toxicity | - | 0.5300 | 53.00% |
| Fish aquatic toxicity | + | 0.9124 | 91.24% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] |
3162.3 nM 7943.3 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3577 | P00352 | Aldehyde dehydrogenase 1A1 |
14988.9 nM 11220.2 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL3687 | P18054 | Arachidonate 12-lipoxygenase |
860 nM |
IC50 |
PMID: 17869117
|
| CHEMBL2903 | P16050 | Arachidonate 15-lipoxygenase |
600 nM 9100 nM |
Ki IC50 |
via Super-PRED
PMID: 17869117 |
| CHEMBL1293236 | P46063 | ATP-dependent DNA helicase Q1 |
5011.9 nM 28183.8 nM 15848.9 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL1293237 | P54132 | Bloom syndrome protein |
15848.9 nM 6309.6 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL4096 | P04637 | Cellular tumor antigen p53 |
631 nM 3981.1 nM 631 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via Super-PRED |
| CHEMBL5587 | P16220 | Cyclic AMP-responsive element-binding protein 1 |
13500 nM |
AC50 |
PMID: 18722769
|
| CHEMBL308 | P06493 | Cyclin-dependent kinase 1 |
6530 nM |
IC50 |
PMID: 18639462
|
| CHEMBL2231 | P04798 | Cytochrome P450 1A1 |
1220 nM |
Ki |
PMID: 21482471
|
| CHEMBL3356 | P05177 | Cytochrome P450 1A2 |
501.19 nM |
AC50 |
via CMAUP
|
| CHEMBL4878 | Q16678 | Cytochrome P450 1B1 |
260 nM |
Ki |
PMID: 21482471
|
| CHEMBL3622 | P33261 | Cytochrome P450 2C19 |
5011.9 nM |
Potency |
via CMAUP
|
| CHEMBL3397 | P11712 | Cytochrome P450 2C9 |
5011.9 nM |
Potency |
via CMAUP
|
| CHEMBL289 | P10635 | Cytochrome P450 2D6 |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL340 | P08684 | Cytochrome P450 3A4 |
31622.8 nM 31622.8 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase |
631 nM 631 nM |
Potency Potency |
via Super-PRED
via CMAUP |
| CHEMBL4159 | Q99714 | Endoplasmic reticulum-associated amyloid beta-peptide-binding protein |
1995.3 nM 3981.1 nM 2511.9 nM |
Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP |
| CHEMBL6144 | P43250 | G protein-coupled receptor kinase 6 |
8700 nM |
IC50 |
via CMAUP
|
| CHEMBL1293267 | Q9HC97 | G-protein coupled receptor 35 |
28200 nM |
IC50 |
PMID: 24900447
|
| CHEMBL2424 | Q04760 | Glyoxalase I |
11000 nM |
IC50 |
PMID: 18258440
|
| CHEMBL4331 | P68871 | Hemoglobin beta chain |
31622.8 nM |
Potency |
via CMAUP
|
| CHEMBL1287622 | Q9Y468 | Lethal(3)malignant brain tumor-like protein 1 |
15848.9 nM |
Potency |
via CMAUP
|
| CHEMBL1293226 | B2RXH2 | Lysine-specific demethylase 4D-like |
3000 nM 891.3 nM 3000 nM |
IC50 Potency IC50 |
DOI: 10.1039/C1MD00199J
via Super-PRED PMID: 21596573 |
| CHEMBL1293224 | P10636 | Microtubule-associated protein tau |
10000 nM 19952.6 nM 28183.8 nM 19952.6 nM 25118.9 nM 7943.3 nM 10000 nM 17782.8 nM 15848.9 nM |
Potency Potency Potency Potency Potency Potency Potency Potency Potency |
via CMAUP
via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP via CMAUP |
| CHEMBL4302 | P08183 | P-glycoprotein 1 |
41000 nM |
IC50 |
PMID: 15481991
|
| CHEMBL3202 | P48147 | Prolyl endopeptidase |
36000 nM |
IC50 |
PMID: 18650094
|
| CHEMBL2396508 | Q13332 | Receptor-type tyrosine-protein phosphatase S |
10300 nM |
IC50 |
PMID: 26602279
|
| CHEMBL2748 | P14410 | Sucrase-isomaltase |
52000 nM 35000 nM |
IC50 IC50 |
PMID: 18255289
PMID: 9834167 |
| CHEMBL1293232 | Q16637 | Survival motor neuron protein |
12589.3 nM |
Potency |
via CMAUP
|
| CHEMBL1947 | P10828 | Thyroid hormone receptor beta-1 |
44668.4 nM 44668.4 nM |
Potency Potency |
via CMAUP
via CMAUP |
| CHEMBL1293227 | O75604 | Ubiquitin carboxyl-terminal hydrolase 2 |
631 nM 631 nM |
Potency Potency |
via Super-PRED
via CMAUP |
| CHEMBL1287617 | P22309 | UDP-glucuronosyltransferase 1-1 |
7000 nM 4400 nM |
IC50 IC50 |
PMID: 21030469
PMID: 21030469 |
| CHEMBL1929 | P47989 | Xanthine dehydrogenase |
2790 nM |
IC50 |
PMID: 9461655
|
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL2581 | P07339 | Cathepsin D | 95.41% | 98.95% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 93.39% | 95.56% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 91.20% | 85.14% |
| CHEMBL1860 | P10827 | Thyroid hormone receptor alpha | 90.84% | 99.15% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 90.79% | 94.00% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 89.21% | 89.00% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 87.96% | 95.50% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 87.83% | 86.33% |
| CHEMBL3194 | P02766 | Transthyretin | 83.92% | 90.71% |
| CHEMBL1293255 | P15428 | 15-hydroxyprostaglandin dehydrogenase [NAD+] | 83.31% | 83.57% |
| CHEMBL2035 | P08912 | Muscarinic acetylcholine receptor M5 | 82.31% | 94.62% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 81.77% | 94.73% |
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 | 5281605 |
| NPASS | NPC239312 |
| ChEMBL | CHEMBL8260 |
| LOTUS | LTS0214160 |
| wikiData | Q2879363 |