(2S)-Isoxanthohumol
| Internal ID | 3aa7cd71-9fb6-44fe-a87b-d559425e0203 |
| Taxonomy | Phenylpropanoids and polyketides > Flavonoids > Flavans > 8-prenylated flavans > 8-prenylated flavanones |
| IUPAC Name | (2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one |
| SMILES (Canonical) | CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)CC(O2)C3=CC=C(C=C3)O)C |
| SMILES (Isomeric) | CC(=CCC1=C2C(=C(C=C1O)OC)C(=O)C[C@H](O2)C3=CC=C(C=C3)O)C |
| InChI | InChI=1S/C21H22O5/c1-12(2)4-9-15-16(23)10-19(25-3)20-17(24)11-18(26-21(15)20)13-5-7-14(22)8-6-13/h4-8,10,18,22-23H,9,11H2,1-3H3/t18-/m0/s1 |
| InChI Key | YKGCBLWILMDSAV-SFHVURJKSA-N |
| Popularity | 5 references in papers |
| Molecular Formula | C21H22O5 |
| Molecular Weight | 354.40 g/mol |
| Exact Mass | 354.14672380 g/mol |
| Topological Polar Surface Area (TPSA) | 76.00 Ų |
| XlogP | 4.10 |
| Atomic LogP (AlogP) | 4.32 |
| H-Bond Acceptor | 5 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 4 |
| (2S)-Isoxanthohumol |
| (-)-Isoxanthohumol |
| (S)-7-Hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-en-1-yl)chroman-4-one |
| (2S)-7-hydroxy-2-(4-hydroxyphenyl)-5-methoxy-8-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one |
| Isoxanthohumol, (-)- |
| Isoxanthohumol (sophora) |
| X4YHZ98N7Q |
| CHEMBL4160626 |
| SCHEMBL14092988 |
| YKGCBLWILMDSAV-SFHVURJKSA-N |
| There are more than 10 synonyms. If you wish to see them all click here. |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9948 | 99.48% |
| Caco-2 | + | 0.8888 | 88.88% |
| Blood Brain Barrier | - | 0.5500 | 55.00% |
| Human oral bioavailability | - | 0.6286 | 62.86% |
| Subcellular localzation | Mitochondria | 0.8193 | 81.93% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8759 | 87.59% |
| OATP1B3 inhibitior | + | 0.8676 | 86.76% |
| MATE1 inhibitior | - | 0.9800 | 98.00% |
| OCT2 inhibitior | - | 0.9000 | 90.00% |
| BSEP inhibitior | + | 0.7040 | 70.40% |
| P-glycoprotein inhibitior | + | 0.6152 | 61.52% |
| P-glycoprotein substrate | - | 0.7641 | 76.41% |
| CYP3A4 substrate | + | 0.5904 | 59.04% |
| CYP2C9 substrate | - | 0.8006 | 80.06% |
| CYP2D6 substrate | - | 0.7235 | 72.35% |
| CYP3A4 inhibition | - | 0.8156 | 81.56% |
| CYP2C9 inhibition | + | 0.8217 | 82.17% |
| CYP2C19 inhibition | + | 0.9318 | 93.18% |
| CYP2D6 inhibition | - | 0.6465 | 64.65% |
| CYP1A2 inhibition | + | 0.7807 | 78.07% |
| CYP2C8 inhibition | + | 0.5533 | 55.33% |
| CYP inhibitory promiscuity | + | 0.8924 | 89.24% |
| UGT catelyzed | + | 0.7000 | 70.00% |
| Carcinogenicity (binary) | - | 0.9613 | 96.13% |
| Carcinogenicity (trinary) | Non-required | 0.6868 | 68.68% |
| Eye corrosion | - | 0.9900 | 99.00% |
| Eye irritation | - | 0.6660 | 66.60% |
| Skin irritation | - | 0.8018 | 80.18% |
| Skin corrosion | - | 0.9638 | 96.38% |
| Ames mutagenesis | - | 0.5254 | 52.54% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4230 | 42.30% |
| Micronuclear | + | 0.5059 | 50.59% |
| Hepatotoxicity | + | 0.5552 | 55.52% |
| skin sensitisation | - | 0.8307 | 83.07% |
| Respiratory toxicity | + | 0.5111 | 51.11% |
| Reproductive toxicity | + | 0.8333 | 83.33% |
| Mitochondrial toxicity | + | 0.7625 | 76.25% |
| Nephrotoxicity | + | 0.5311 | 53.11% |
| Acute Oral Toxicity (c) | III | 0.6532 | 65.32% |
| Estrogen receptor binding | + | 0.8560 | 85.60% |
| Androgen receptor binding | + | 0.7107 | 71.07% |
| Thyroid receptor binding | + | 0.6662 | 66.62% |
| Glucocorticoid receptor binding | + | 0.7632 | 76.32% |
| Aromatase binding | - | 0.5486 | 54.86% |
| PPAR gamma | + | 0.7939 | 79.39% |
| Honey bee toxicity | - | 0.7510 | 75.10% |
| Biodegradation | - | 0.8250 | 82.50% |
| Crustacea aquatic toxicity | - | 0.6000 | 60.00% |
| Fish aquatic toxicity | + | 0.9846 | 98.46% |
Proven Targets:
| CHEMBL ID | UniProt ID | Name | Min activity | Assay type | Source |
|---|---|---|---|---|---|
| No proven targets yet! | |||||
Predicted Targets (via Super-PRED):
| CHEMBL ID | UniProt ID | Name | Probability | Model accuracy |
|---|---|---|---|---|
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 98.97% | 91.11% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 97.44% | 85.14% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 95.54% | 94.45% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 93.57% | 96.09% |
| CHEMBL2581 | P07339 | Cathepsin D | 93.22% | 98.95% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 91.67% | 86.33% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 91.49% | 95.56% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 90.41% | 99.17% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 90.25% | 97.09% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 88.23% | 94.73% |
| CHEMBL2535 | P11166 | Glucose transporter | 86.13% | 98.75% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 85.87% | 94.00% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 85.57% | 95.89% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 85.12% | 89.00% |
| CHEMBL4208 | P20618 | Proteasome component C5 | 83.52% | 90.00% |
| CHEMBL4793 | Q86TI2 | Dipeptidyl peptidase IX | 81.16% | 96.95% |
| CHEMBL1907603 | Q05586 | Glutamate NMDA receptor; GRIN1/GRIN2B | 80.68% | 95.89% |
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.
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