[(3aR,4R,5R,6S,6aS,9S,9aS,9bR)-5-acetyloxy-9-hydroperoxy-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] 2-methylpropanoate
| Internal ID | e74dc652-8472-48fa-9bf8-5bd5df2f118d |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives |
| IUPAC Name | [(3aR,4R,5R,6S,6aS,9S,9aS,9bR)-5-acetyloxy-9-hydroperoxy-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] 2-methylpropanoate |
| SMILES (Canonical) | CC(C)C(=O)OC1C2C(C3C(C=CC3(C)OO)C(C1OC(=O)C)(C)O)OC(=O)C2=C |
| SMILES (Isomeric) | CC(C)C(=O)O[C@@H]1[C@H]2[C@H]([C@@H]3[C@H](C=C[C@]3(C)OO)[C@]([C@@H]1OC(=O)C)(C)O)OC(=O)C2=C |
| InChI | InChI=1S/C21H28O9/c1-9(2)18(23)29-16-13-10(3)19(24)28-15(13)14-12(7-8-20(14,5)30-26)21(6,25)17(16)27-11(4)22/h7-9,12-17,25-26H,3H2,1-2,4-6H3/t12-,13+,14-,15+,16+,17+,20-,21-/m0/s1 |
| InChI Key | MFFDNJQADQPGPW-XSVYMCFTSA-N |
| Popularity | 1 reference in papers |
| Molecular Formula | C21H28O9 |
| Molecular Weight | 424.40 g/mol |
| Exact Mass | 424.17333247 g/mol |
| Topological Polar Surface Area (TPSA) | 129.00 Ų |
| XlogP | 1.20 |
| Atomic LogP (AlogP) | 1.40 |
| H-Bond Acceptor | 9 |
| H-Bond Donor | 2 |
| Rotatable Bonds | 4 |
| There are no found synonyms. |
![2D Structure of [(3aR,4R,5R,6S,6aS,9S,9aS,9bR)-5-acetyloxy-9-hydroperoxy-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] 2-methylpropanoate](https://plantaedb.com/storage/docs/compounds/2023/11/f0efee40-8699-11ee-a985-51284105365b.jpg "2D Structure of [(3aR,4R,5R,6S,6aS,9S,9aS,9bR)-5-acetyloxy-9-hydroperoxy-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-3a,4,5,6a,9a,9b-hexahydroazuleno[4,5-b]furan-4-yl] 2-methylpropanoate")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9395 | 93.95% |
| Caco-2 | - | 0.5811 | 58.11% |
| Blood Brain Barrier | + | 0.5500 | 55.00% |
| Human oral bioavailability | - | 0.5000 | 50.00% |
| Subcellular localzation | Mitochondria | 0.5988 | 59.88% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8127 | 81.27% |
| OATP1B3 inhibitior | + | 0.9023 | 90.23% |
| MATE1 inhibitior | - | 1.0000 | 100.00% |
| OCT2 inhibitior | - | 0.9500 | 95.00% |
| BSEP inhibitior | - | 0.7354 | 73.54% |
| P-glycoprotein inhibitior | + | 0.5953 | 59.53% |
| P-glycoprotein substrate | - | 0.6529 | 65.29% |
| CYP3A4 substrate | + | 0.6348 | 63.48% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8988 | 89.88% |
| CYP3A4 inhibition | - | 0.8307 | 83.07% |
| CYP2C9 inhibition | - | 0.8150 | 81.50% |
| CYP2C19 inhibition | - | 0.7788 | 77.88% |
| CYP2D6 inhibition | - | 0.9151 | 91.51% |
| CYP1A2 inhibition | - | 0.7723 | 77.23% |
| CYP2C8 inhibition | - | 0.6546 | 65.46% |
| CYP inhibitory promiscuity | - | 0.8212 | 82.12% |
| UGT catelyzed | - | 0.5000 | 50.00% |
| Carcinogenicity (binary) | - | 0.8543 | 85.43% |
| Carcinogenicity (trinary) | Non-required | 0.4478 | 44.78% |
| Eye corrosion | - | 0.9463 | 94.63% |
| Eye irritation | - | 0.8815 | 88.15% |
| Skin irritation | - | 0.6965 | 69.65% |
| Skin corrosion | - | 0.8997 | 89.97% |
| Ames mutagenesis | - | 0.5600 | 56.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5716 | 57.16% |
| Micronuclear | - | 0.5200 | 52.00% |
| Hepatotoxicity | + | 0.8158 | 81.58% |
| skin sensitisation | - | 0.6890 | 68.90% |
| Respiratory toxicity | + | 0.6444 | 64.44% |
| Reproductive toxicity | + | 0.5444 | 54.44% |
| Mitochondrial toxicity | + | 0.7000 | 70.00% |
| Nephrotoxicity | + | 0.6877 | 68.77% |
| Acute Oral Toxicity (c) | III | 0.4435 | 44.35% |
| Estrogen receptor binding | + | 0.7995 | 79.95% |
| Androgen receptor binding | + | 0.5859 | 58.59% |
| Thyroid receptor binding | + | 0.6080 | 60.80% |
| Glucocorticoid receptor binding | + | 0.6345 | 63.45% |
| Aromatase binding | + | 0.5699 | 56.99% |
| PPAR gamma | + | 0.7168 | 71.68% |
| Honey bee toxicity | - | 0.5764 | 57.64% |
| Biodegradation | - | 0.7000 | 70.00% |
| Crustacea aquatic toxicity | - | 0.6700 | 67.00% |
| Fish aquatic toxicity | + | 0.9716 | 97.16% |
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 | 98.58% | 91.11% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 94.80% | 94.45% |
| CHEMBL2581 | P07339 | Cathepsin D | 94.34% | 98.95% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 94.11% | 97.25% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 93.60% | 85.14% |
| CHEMBL2996 | Q05655 | Protein kinase C delta | 93.08% | 97.79% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 91.25% | 96.09% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 89.49% | 99.23% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 89.33% | 89.00% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 85.39% | 86.33% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 84.91% | 91.19% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 83.52% | 95.56% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 81.17% | 94.00% |
| CHEMBL1951 | P21397 | Monoamine oxidase A | 80.48% | 91.49% |
| PubChem | 163030883 |
| LOTUS | LTS0164727 |
| wikiData | Q105162618 |