Kaerophyllin
| Internal ID | 7a29c32d-e3a9-496a-a134-db7f90ebc3e3 |
| Taxonomy | Lignans, neolignans and related compounds > Furanoid lignans > Tetrahydrofuran lignans > 9,9-epoxylignans > Dibenzylbutyrolactone lignans |
| IUPAC Name | (3E,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methylidene]oxolan-2-one |
| SMILES (Canonical) | COC1=C(C=C(C=C1)C=C2C(COC2=O)CC3=CC4=C(C=C3)OCO4)OC |
| SMILES (Isomeric) | COC1=C(C=C(C=C1)/C=C/2\[C@H](COC2=O)CC3=CC4=C(C=C3)OCO4)OC |
| InChI | InChI=1S/C21H20O6/c1-23-17-5-3-14(9-19(17)24-2)8-16-15(11-25-21(16)22)7-13-4-6-18-20(10-13)27-12-26-18/h3-6,8-10,15H,7,11-12H2,1-2H3/b16-8+/t15-/m0/s1 |
| InChI Key | CSKOHFAJPKLSBP-MDNIKOHYSA-N |
| Popularity | 2 references in papers |
| Molecular Formula | C21H20O6 |
| Molecular Weight | 368.40 g/mol |
| Exact Mass | 368.12598835 g/mol |
| Topological Polar Surface Area (TPSA) | 63.20 Ų |
| XlogP | 3.70 |
| Atomic LogP (AlogP) | 3.23 |
| H-Bond Acceptor | 6 |
| H-Bond Donor | 0 |
| Rotatable Bonds | 5 |
| 75590-33-9 |
| (3E,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methylidene]oxolan-2-one |
| 2(3H)-Furanone, 4-(1,3-benzodioxol-5-ylmethyl)-3-((3,4-dimethoxyphenyl)methylene)dihydro-, (3E,4R)- |
| SCHEMBL14252987 |
| Chaerophyllin (6CI); (3E,4R)-4-(1,3-Benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methylene]dihydro-2(3H)-furanone |
| HY-N3429 |
| AKOS040761939 |
| CS-0024211 |
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9930 | 99.30% |
| Caco-2 | + | 0.7273 | 72.73% |
| Blood Brain Barrier | + | 0.6750 | 67.50% |
| Human oral bioavailability | + | 0.5286 | 52.86% |
| Subcellular localzation | Mitochondria | 0.7603 | 76.03% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.9332 | 93.32% |
| OATP1B3 inhibitior | + | 0.9630 | 96.30% |
| MATE1 inhibitior | - | 0.8400 | 84.00% |
| OCT2 inhibitior | - | 1.0000 | 100.00% |
| BSEP inhibitior | + | 0.9656 | 96.56% |
| P-glycoprotein inhibitior | + | 0.8479 | 84.79% |
| P-glycoprotein substrate | - | 0.7162 | 71.62% |
| CYP3A4 substrate | + | 0.5784 | 57.84% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.7972 | 79.72% |
| CYP3A4 inhibition | + | 0.9591 | 95.91% |
| CYP2C9 inhibition | + | 0.9399 | 93.99% |
| CYP2C19 inhibition | + | 0.9801 | 98.01% |
| CYP2D6 inhibition | + | 0.8096 | 80.96% |
| CYP1A2 inhibition | + | 0.6598 | 65.98% |
| CYP2C8 inhibition | + | 0.4521 | 45.21% |
| CYP inhibitory promiscuity | + | 0.9845 | 98.45% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.9400 | 94.00% |
| Carcinogenicity (trinary) | Non-required | 0.4437 | 44.37% |
| Eye corrosion | - | 0.9813 | 98.13% |
| Eye irritation | - | 0.9005 | 90.05% |
| Skin irritation | - | 0.7722 | 77.22% |
| Skin corrosion | - | 0.9554 | 95.54% |
| Ames mutagenesis | - | 0.5400 | 54.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.8112 | 81.12% |
| Micronuclear | + | 0.6874 | 68.74% |
| Hepatotoxicity | + | 0.6625 | 66.25% |
| skin sensitisation | + | 0.5463 | 54.63% |
| Respiratory toxicity | + | 0.5333 | 53.33% |
| Reproductive toxicity | + | 0.7444 | 74.44% |
| Mitochondrial toxicity | - | 0.5500 | 55.00% |
| Nephrotoxicity | - | 0.5894 | 58.94% |
| Acute Oral Toxicity (c) | III | 0.6175 | 61.75% |
| Estrogen receptor binding | + | 0.9069 | 90.69% |
| Androgen receptor binding | + | 0.6592 | 65.92% |
| Thyroid receptor binding | + | 0.6468 | 64.68% |
| Glucocorticoid receptor binding | + | 0.7358 | 73.58% |
| Aromatase binding | - | 0.5330 | 53.30% |
| PPAR gamma | + | 0.7080 | 70.80% |
| Honey bee toxicity | - | 0.7846 | 78.46% |
| Biodegradation | - | 0.7750 | 77.50% |
| Crustacea aquatic toxicity | + | 0.5600 | 56.00% |
| Fish aquatic toxicity | + | 0.9897 | 98.97% |
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 |
|---|---|---|---|---|
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 96.55% | 94.45% |
| CHEMBL2581 | P07339 | Cathepsin D | 95.74% | 98.95% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 95.33% | 86.33% |
| CHEMBL4481 | P35228 | Nitric oxide synthase, inducible | 94.90% | 94.80% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 94.78% | 95.56% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 93.51% | 91.11% |
| CHEMBL2373 | P21730 | C5a anaphylatoxin chemotactic receptor | 92.34% | 92.62% |
| CHEMBL1075094 | Q16236 | Nuclear factor erythroid 2-related factor 2 | 90.67% | 96.00% |
| CHEMBL4303 | P08238 | Heat shock protein HSP 90-beta | 89.04% | 96.77% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 88.93% | 97.09% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 88.69% | 96.09% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 88.23% | 95.89% |
| CHEMBL2535 | P11166 | Glucose transporter | 87.54% | 98.75% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 87.48% | 89.00% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 86.55% | 95.50% |
| CHEMBL4478 | Q00975 | Voltage-gated N-type calcium channel alpha-1B subunit | 85.17% | 97.14% |
| CHEMBL1907603 | Q05586 | Glutamate NMDA receptor; GRIN1/GRIN2B | 84.10% | 95.89% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 83.46% | 85.14% |
| CHEMBL3060 | Q9Y345 | Glycine transporter 2 | 82.69% | 99.17% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 80.77% | 94.00% |
| CHEMBL3807 | P17706 | T-cell protein-tyrosine phosphatase | 80.76% | 93.00% |
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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| PubChem | 6440534 |
| NPASS | NPC18333 |
| LOTUS | LTS0208550 |
| wikiData | Q104396258 |