[(3aS,4R,5R,6S,6aS,7R,9aS,9bR)-4,5-diacetyloxy-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-7-yl] acetate
| Internal ID | 1ce333bf-b373-4473-bca3-3056968bd3e6 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives |
| IUPAC Name | [(3aS,4R,5R,6S,6aS,7R,9aS,9bR)-4,5-diacetyloxy-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-7-yl] acetate |
| SMILES (Canonical) | CC1=CC(C2C1C3C(C(C(C2(C)O)OC(=O)C)OC(=O)C)C(=C)C(=O)O3)OC(=O)C |
| SMILES (Isomeric) | CC1=C[C@H]([C@@H]2[C@@H]1[C@@H]3[C@@H]([C@H]([C@H]([C@@]2(C)O)OC(=O)C)OC(=O)C)C(=C)C(=O)O3)OC(=O)C |
| InChI | InChI=1S/C21H26O9/c1-8-7-13(27-10(3)22)16-14(8)17-15(9(2)20(25)30-17)18(28-11(4)23)19(21(16,6)26)29-12(5)24/h7,13-19,26H,2H2,1,3-6H3/t13-,14-,15+,16-,17-,18-,19-,21+/m1/s1 |
| InChI Key | NKABGRCMUYRLLO-WZUGRFOZSA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C21H26O9 |
| Molecular Weight | 422.40 g/mol |
| Exact Mass | 422.15768240 g/mol |
| Topological Polar Surface Area (TPSA) | 125.00 Ų |
| XlogP | 0.40 |
| Atomic LogP (AlogP) | 0.84 |
| H-Bond Acceptor | 9 |
| H-Bond Donor | 1 |
| Rotatable Bonds | 3 |
| There are no found synonyms. |
![2D Structure of [(3aS,4R,5R,6S,6aS,7R,9aS,9bR)-4,5-diacetyloxy-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-7-yl] acetate](https://plantaedb.com/storage/docs/compounds/2023/11/dc0b4390-8569-11ee-81db-a51b167d7753.jpg "2D Structure of [(3aS,4R,5R,6S,6aS,7R,9aS,9bR)-4,5-diacetyloxy-6-hydroxy-6,9-dimethyl-3-methylidene-2-oxo-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan-7-yl] acetate")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9737 | 97.37% |
| Caco-2 | - | 0.6945 | 69.45% |
| Blood Brain Barrier | + | 0.6000 | 60.00% |
| Human oral bioavailability | - | 0.5714 | 57.14% |
| Subcellular localzation | Mitochondria | 0.5760 | 57.60% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8530 | 85.30% |
| OATP1B3 inhibitior | + | 0.8949 | 89.49% |
| MATE1 inhibitior | - | 0.9000 | 90.00% |
| OCT2 inhibitior | - | 0.9500 | 95.00% |
| BSEP inhibitior | - | 0.6962 | 69.62% |
| P-glycoprotein inhibitior | + | 0.6933 | 69.33% |
| P-glycoprotein substrate | - | 0.7499 | 74.99% |
| CYP3A4 substrate | + | 0.6160 | 61.60% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.9029 | 90.29% |
| CYP3A4 inhibition | - | 0.6605 | 66.05% |
| CYP2C9 inhibition | - | 0.9325 | 93.25% |
| CYP2C19 inhibition | - | 0.8761 | 87.61% |
| CYP2D6 inhibition | - | 0.9566 | 95.66% |
| CYP1A2 inhibition | - | 0.8013 | 80.13% |
| CYP2C8 inhibition | - | 0.7193 | 71.93% |
| CYP inhibitory promiscuity | - | 0.8939 | 89.39% |
| UGT catelyzed | + | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.9243 | 92.43% |
| Carcinogenicity (trinary) | Non-required | 0.4079 | 40.79% |
| Eye corrosion | - | 0.9371 | 93.71% |
| Eye irritation | - | 0.7943 | 79.43% |
| Skin irritation | - | 0.6194 | 61.94% |
| Skin corrosion | - | 0.9176 | 91.76% |
| Ames mutagenesis | - | 0.5300 | 53.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.5928 | 59.28% |
| Micronuclear | + | 0.5200 | 52.00% |
| Hepatotoxicity | + | 0.8034 | 80.34% |
| skin sensitisation | - | 0.6377 | 63.77% |
| Respiratory toxicity | + | 0.5778 | 57.78% |
| Reproductive toxicity | - | 0.5111 | 51.11% |
| Mitochondrial toxicity | + | 0.7250 | 72.50% |
| Nephrotoxicity | + | 0.7200 | 72.00% |
| Acute Oral Toxicity (c) | II | 0.3288 | 32.88% |
| Estrogen receptor binding | + | 0.7816 | 78.16% |
| Androgen receptor binding | - | 0.4912 | 49.12% |
| Thyroid receptor binding | + | 0.5573 | 55.73% |
| Glucocorticoid receptor binding | + | 0.5549 | 55.49% |
| Aromatase binding | - | 0.5490 | 54.90% |
| PPAR gamma | + | 0.6820 | 68.20% |
| Honey bee toxicity | - | 0.5289 | 52.89% |
| Biodegradation | - | 0.7500 | 75.00% |
| Crustacea aquatic toxicity | - | 0.5750 | 57.50% |
| Fish aquatic toxicity | + | 0.9481 | 94.81% |
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 | 93.86% | 91.11% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 92.80% | 94.45% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 89.34% | 86.33% |
| CHEMBL2581 | P07339 | Cathepsin D | 89.01% | 98.95% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 88.72% | 99.23% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 88.28% | 95.56% |
| CHEMBL2996 | Q05655 | Protein kinase C delta | 86.91% | 97.79% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 86.03% | 94.00% |
| CHEMBL3091268 | Q92753 | Nuclear receptor ROR-beta | 85.97% | 95.50% |
| CHEMBL4261 | Q16665 | Hypoxia-inducible factor 1 alpha | 84.68% | 85.14% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 84.43% | 89.00% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 83.61% | 91.19% |
| CHEMBL3401 | O75469 | Pregnane X receptor | 82.30% | 94.73% |
| PubChem | 162983680 |
| LOTUS | LTS0145449 |
| wikiData | Q103786498 |