[(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate
| Internal ID | 5e75c063-7e47-4823-9ab1-cecefd017ad8 |
| Taxonomy | Lipids and lipid-like molecules > Prenol lipids > Terpene lactones > Sesquiterpene lactones > Guaianolides and derivatives |
| IUPAC Name | [(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate |
| SMILES (Canonical) | CC(CCl)(C(=O)OC1CC(=C)C2CC(C(C2C3C1C(=C)C(=O)O3)(CCl)O)O)OCCC4=CC=C(C=C4)O |
| SMILES (Isomeric) | C[C@@](CCl)(C(=O)O[C@H]1CC(=C)[C@@H]2C[C@@H]([C@@]([C@@H]2[C@@H]3[C@@H]1C(=C)C(=O)O3)(CCl)O)O)OCCC4=CC=C(C=C4)O |
| InChI | InChI=1S/C27H32Cl2O8/c1-14-10-19(36-25(33)26(3,12-28)35-9-8-16-4-6-17(30)7-5-16)21-15(2)24(32)37-23(21)22-18(14)11-20(31)27(22,34)13-29/h4-7,18-23,30-31,34H,1-2,8-13H2,3H3/t18-,19-,20-,21+,22-,23-,26+,27+/m0/s1 |
| InChI Key | VLUKWHIZVPGABG-LSEJKCCISA-N |
| Popularity | 0 references in papers |
| Molecular Formula | C27H32Cl2O8 |
| Molecular Weight | 555.40 g/mol |
| Exact Mass | 554.1474234 g/mol |
| Topological Polar Surface Area (TPSA) | 123.00 Ų |
| XlogP | 3.00 |
| Atomic LogP (AlogP) | 2.89 |
| H-Bond Acceptor | 8 |
| H-Bond Donor | 3 |
| Rotatable Bonds | 8 |
| There are no found synonyms. |
![2D Structure of [(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate](https://plantaedb.com/storage/docs/compounds/2023/11/94d3bb10-85d9-11ee-a28f-9fc41b398d2a.jpg "2D Structure of [(3aR,4S,6aR,8S,9S,9aS,9bS)-9-(chloromethyl)-8,9-dihydroxy-3,6-dimethylidene-2-oxo-3a,4,5,6a,7,8,9a,9b-octahydroazuleno[4,5-b]furan-4-yl] (2S)-3-chloro-2-[2-(4-hydroxyphenyl)ethoxy]-2-methylpropanoate")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9761 | 97.61% |
| Caco-2 | - | 0.8537 | 85.37% |
| Blood Brain Barrier | - | 0.5250 | 52.50% |
| Human oral bioavailability | - | 0.7000 | 70.00% |
| Subcellular localzation | Mitochondria | 0.7943 | 79.43% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.7906 | 79.06% |
| OATP1B3 inhibitior | + | 0.9272 | 92.72% |
| MATE1 inhibitior | - | 0.9400 | 94.00% |
| OCT2 inhibitior | - | 0.7750 | 77.50% |
| BSEP inhibitior | + | 0.8529 | 85.29% |
| P-glycoprotein inhibitior | + | 0.6231 | 62.31% |
| P-glycoprotein substrate | + | 0.6817 | 68.17% |
| CYP3A4 substrate | + | 0.7350 | 73.50% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.8387 | 83.87% |
| CYP3A4 inhibition | - | 0.6811 | 68.11% |
| CYP2C9 inhibition | - | 0.6582 | 65.82% |
| CYP2C19 inhibition | - | 0.5831 | 58.31% |
| CYP2D6 inhibition | - | 0.8922 | 89.22% |
| CYP1A2 inhibition | - | 0.5561 | 55.61% |
| CYP2C8 inhibition | + | 0.8158 | 81.58% |
| CYP inhibitory promiscuity | - | 0.9084 | 90.84% |
| UGT catelyzed | + | 0.6000 | 60.00% |
| Carcinogenicity (binary) | - | 0.8344 | 83.44% |
| Carcinogenicity (trinary) | Non-required | 0.4871 | 48.71% |
| Eye corrosion | - | 0.9870 | 98.70% |
| Eye irritation | - | 0.9368 | 93.68% |
| Skin irritation | - | 0.6521 | 65.21% |
| Skin corrosion | - | 0.9191 | 91.91% |
| Ames mutagenesis | - | 0.6800 | 68.00% |
| Human Ether-a-go-go-Related Gene inhibition | - | 0.4698 | 46.98% |
| Micronuclear | - | 0.7900 | 79.00% |
| Hepatotoxicity | + | 0.6052 | 60.52% |
| skin sensitisation | - | 0.8388 | 83.88% |
| Respiratory toxicity | + | 0.7444 | 74.44% |
| Reproductive toxicity | + | 0.8778 | 87.78% |
| Mitochondrial toxicity | + | 0.8500 | 85.00% |
| Nephrotoxicity | + | 0.8140 | 81.40% |
| Acute Oral Toxicity (c) | III | 0.4270 | 42.70% |
| Estrogen receptor binding | + | 0.7775 | 77.75% |
| Androgen receptor binding | + | 0.7507 | 75.07% |
| Thyroid receptor binding | + | 0.5891 | 58.91% |
| Glucocorticoid receptor binding | + | 0.7819 | 78.19% |
| Aromatase binding | + | 0.7097 | 70.97% |
| PPAR gamma | + | 0.6531 | 65.31% |
| Honey bee toxicity | - | 0.5966 | 59.66% |
| Biodegradation | - | 0.7500 | 75.00% |
| Crustacea aquatic toxicity | - | 0.5353 | 53.53% |
| Fish aquatic toxicity | + | 1.0000 | 100.00% |
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 | 98.83% | 91.11% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 97.90% | 97.25% |
| CHEMBL2996 | Q05655 | Protein kinase C delta | 97.09% | 97.79% |
| CHEMBL2581 | P07339 | Cathepsin D | 96.81% | 98.95% |
| CHEMBL2035 | P08912 | Muscarinic acetylcholine receptor M5 | 96.14% | 94.62% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 95.91% | 86.33% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 95.12% | 94.45% |
| CHEMBL211 | P08172 | Muscarinic acetylcholine receptor M2 | 95.00% | 94.97% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 94.24% | 96.09% |
| CHEMBL5966 | P55899 | IgG receptor FcRn large subunit p51 | 91.63% | 90.93% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 91.33% | 97.09% |
| CHEMBL3713062 | P10646 | Tissue factor pathway inhibitor | 90.00% | 97.33% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 87.10% | 95.89% |
| CHEMBL3004 | P33527 | Multidrug resistance-associated protein 1 | 86.47% | 96.37% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 85.03% | 95.56% |
| CHEMBL2635 | P51452 | Dual specificity protein phosphatase 3 | 82.26% | 94.00% |
| CHEMBL340 | P08684 | Cytochrome P450 3A4 | 80.71% | 91.19% |
| CHEMBL1902 | P62942 | FK506-binding protein 1A | 80.71% | 97.05% |
| CHEMBL5163 | Q9NY46 | Sodium channel protein type III alpha subunit | 80.64% | 96.90% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 80.15% | 89.00% |
| CHEMBL1907603 | Q05586 | Glutamate NMDA receptor; GRIN1/GRIN2B | 80.12% | 95.89% |
| PubChem | 21593843 |
| LOTUS | LTS0080785 |
| wikiData | Q105288714 |