[(3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-4-propanoyloxy-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-3-yl] (Z)-2-methylbut-2-enoate
| Internal ID | 6f058b69-e6e1-4021-b9c0-f2bec065ab53 |
| Taxonomy | Organic acids and derivatives > Carboxylic acids and derivatives > Tricarboxylic acids and derivatives |
| IUPAC Name | [(3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-4-propanoyloxy-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-3-yl] (Z)-2-methylbut-2-enoate |
| SMILES (Canonical) | CCC(=O)OC1CC(=C2C(C3C1C(C(=O)O3)(C)OC(=O)C(=CC)C)C(=CC2=O)C)C |
| SMILES (Isomeric) | CCC(=O)O[C@H]1CC(=C2[C@H]([C@H]3[C@@H]1[C@](C(=O)O3)(C)OC(=O)/C(=C\C)/C)C(=CC2=O)C)C |
| InChI | InChI=1S/C23H28O7/c1-7-11(3)21(26)30-23(6)19-15(28-16(25)8-2)10-13(5)17-14(24)9-12(4)18(17)20(19)29-22(23)27/h7,9,15,18-20H,8,10H2,1-6H3/b11-7-/t15-,18+,19+,20-,23-/m0/s1 |
| InChI Key | AYWUJPCNTAUFOA-DFCGMIGISA-N |
| Popularity | 1 reference in papers |
| Molecular Formula | C23H28O7 |
| Molecular Weight | 416.50 g/mol |
| Exact Mass | 416.18350323 g/mol |
| Topological Polar Surface Area (TPSA) | 96.00 Ų |
| XlogP | 2.50 |
| Atomic LogP (AlogP) | 2.98 |
| H-Bond Acceptor | 7 |
| H-Bond Donor | 0 |
| Rotatable Bonds | 4 |
| There are no found synonyms. |
![2D Structure of [(3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-4-propanoyloxy-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-3-yl] (Z)-2-methylbut-2-enoate](https://plantaedb.com/storage/docs/compounds/2023/11/daucoguaianolactone-c.jpg "2D Structure of [(3S,3aR,4S,9aR,9bS)-3,6,9-trimethyl-2,7-dioxo-4-propanoyloxy-4,5,9a,9b-tetrahydro-3aH-azuleno[4,5-b]furan-3-yl] (Z)-2-methylbut-2-enoate")
| Target | Value | Probability (raw) | Probability (%) |
|---|---|---|---|
| Human Intestinal Absorption | + | 0.9922 | 99.22% |
| Caco-2 | + | 0.5901 | 59.01% |
| Blood Brain Barrier | + | 0.7000 | 70.00% |
| Human oral bioavailability | - | 0.5714 | 57.14% |
| Subcellular localzation | Mitochondria | 0.5665 | 56.65% |
| OATP2B1 inhibitior | - | 1.0000 | 100.00% |
| OATP1B1 inhibitior | + | 0.8453 | 84.53% |
| OATP1B3 inhibitior | + | 0.8954 | 89.54% |
| MATE1 inhibitior | - | 0.7200 | 72.00% |
| OCT2 inhibitior | - | 0.8500 | 85.00% |
| BSEP inhibitior | + | 0.8898 | 88.98% |
| P-glycoprotein inhibitior | + | 0.8365 | 83.65% |
| P-glycoprotein substrate | + | 0.5434 | 54.34% |
| CYP3A4 substrate | + | 0.6672 | 66.72% |
| CYP2C9 substrate | - | 1.0000 | 100.00% |
| CYP2D6 substrate | - | 0.9027 | 90.27% |
| CYP3A4 inhibition | - | 0.6304 | 63.04% |
| CYP2C9 inhibition | - | 0.7475 | 74.75% |
| CYP2C19 inhibition | - | 0.6491 | 64.91% |
| CYP2D6 inhibition | - | 0.9531 | 95.31% |
| CYP1A2 inhibition | - | 0.6209 | 62.09% |
| CYP2C8 inhibition | + | 0.5116 | 51.16% |
| CYP inhibitory promiscuity | - | 0.7463 | 74.63% |
| UGT catelyzed | - | 0.0000 | 0.00% |
| Carcinogenicity (binary) | - | 0.9143 | 91.43% |
| Carcinogenicity (trinary) | Non-required | 0.4746 | 47.46% |
| Eye corrosion | - | 0.9693 | 96.93% |
| Eye irritation | - | 0.8941 | 89.41% |
| Skin irritation | - | 0.6200 | 62.00% |
| Skin corrosion | - | 0.9274 | 92.74% |
| Ames mutagenesis | - | 0.5200 | 52.00% |
| Human Ether-a-go-go-Related Gene inhibition | + | 0.7059 | 70.59% |
| Micronuclear | - | 0.5500 | 55.00% |
| Hepatotoxicity | + | 0.6053 | 60.53% |
| skin sensitisation | - | 0.6823 | 68.23% |
| Respiratory toxicity | + | 0.6222 | 62.22% |
| Reproductive toxicity | + | 0.6667 | 66.67% |
| Mitochondrial toxicity | + | 0.6625 | 66.25% |
| Nephrotoxicity | + | 0.7109 | 71.09% |
| Acute Oral Toxicity (c) | III | 0.5084 | 50.84% |
| Estrogen receptor binding | + | 0.7476 | 74.76% |
| Androgen receptor binding | + | 0.6092 | 60.92% |
| Thyroid receptor binding | + | 0.5179 | 51.79% |
| Glucocorticoid receptor binding | + | 0.7652 | 76.52% |
| Aromatase binding | - | 0.5419 | 54.19% |
| PPAR gamma | + | 0.7506 | 75.06% |
| Honey bee toxicity | - | 0.7289 | 72.89% |
| Biodegradation | - | 0.8500 | 85.00% |
| Crustacea aquatic toxicity | + | 0.5100 | 51.00% |
| Fish aquatic toxicity | + | 0.9740 | 97.40% |
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 |
|---|---|---|---|---|
| CHEMBL221 | P23219 | Cyclooxygenase-1 | 98.76% | 90.17% |
| CHEMBL4203 | Q9HAZ1 | Dual specificity protein kinase CLK4 | 95.76% | 94.45% |
| CHEMBL3251 | P19838 | Nuclear factor NF-kappa-B p105 subunit | 94.12% | 96.09% |
| CHEMBL5619 | P27695 | DNA-(apurinic or apyrimidinic site) lyase | 93.23% | 91.11% |
| CHEMBL241 | Q14432 | Phosphodiesterase 3A | 88.96% | 92.94% |
| CHEMBL1806 | P11388 | DNA topoisomerase II alpha | 88.11% | 89.00% |
| CHEMBL2581 | P07339 | Cathepsin D | 87.90% | 98.95% |
| CHEMBL4793 | Q86TI2 | Dipeptidyl peptidase IX | 86.57% | 96.95% |
| CHEMBL3038477 | P67870 | Casein kinase II alpha/beta | 84.43% | 99.23% |
| CHEMBL3108638 | O15164 | Transcription intermediary factor 1-alpha | 84.10% | 95.56% |
| CHEMBL1994 | P08235 | Mineralocorticoid receptor | 82.69% | 100.00% |
| CHEMBL4657 | Q6V1X1 | Dipeptidyl peptidase VIII | 82.27% | 97.21% |
| CHEMBL1293249 | Q13887 | Kruppel-like factor 5 | 81.93% | 86.33% |
| CHEMBL253 | P34972 | Cannabinoid CB2 receptor | 81.32% | 97.25% |
| CHEMBL255 | P29275 | Adenosine A2b receptor | 80.97% | 98.59% |
| CHEMBL3137262 | O60341 | LSD1/CoREST complex | 80.46% | 97.09% |
| CHEMBL5608 | Q16288 | NT-3 growth factor receptor | 80.41% | 95.89% |
| PubChem | 102165830 |
| LOTUS | LTS0028253 |
| wikiData | Q104921446 |